More Torment From Kylie [forced bi] [chastity] [humiliation]

A follow up to my previous story. This time my ex-girlfriend Kylie wants to see me suck cock in order to earn release, but only after I find myself in an uncomfortable situation at a bachelor party. This story is part of my latest collection, available on Kindle. The final part of my adventures with Kylie will be posted in a week or so.

I didn’t hear from Kylie for almost two weeks and when she did it was just a quick check in. I asked her about a new task to be unlocked again and she just said ‘not yet’ and stopped replying.

A week or so after that, it was a friend’s twenty-first birthday and he had a big day planned. I hadn’t had a chance to think about it between work and my predicament. Being caged with little contact and no idea when I would be unlocked was a new level of intensity for me - it had stopped feeling like a game and started taking over my whole being. It made me constantly horny and submissive, craving any stimulation whatsoever. I wore panties everyday and used my largest dildo on myself in my free evenings, not because I had been told to but because I craved it.

When the birthday night out came around, I was little more than a quivering wreck. I’d managed a caged orgasm from anal play a few days before but it had made things worse, rather than better. I almost cancelled, but instead decided I would power on through. I showered, groomed and put on a decent outfit, including wearing boxers for the first time in weeks and headed out to meet the others.

We had a few drinks and some food and moved onto a small nightclub. There was a lot of laughter and banter and I got quite tipsy, which helped me forget about the cage. We headed on from the club, but I’d missed the conversation to decide where we were going and just followed along with everyone else until we stood outside the blackedout front of a strip club. I was hesitant, but everyone else was keen so I piled in with them, paid at the door and grabbed a drink from the bar.

I tried to keep myself to myself as the girls were moving around trying to encourage men to buy private dances. Their skimpy outfits were divine and I could feel myself leaking non stop in my cage, especially whenever any of them came to speak to me.

I turned down offers to buy dances a couple of times, but there was one girl that I couldn’t take my eyes off. Slim and pale with jet black hair, with a dyed red streak; she wore fishnets stockings, garters, some black laced panties and a very sexy black and red corset. She had some tattoos and piercings and was very much the type of girl I liked. I watched her from a distance as she spoke with various patrons, including Dan, one of my closest friends.

 Shortly after speaking with him, she meandered her way across the bar towards me with a sultry smile on her face. She didn’t say anything, she just took me by the hand and smiled, leading me towards the private area.
‘Umm, I’m not buying a dance,’ I stammered.

‘It’s okay,’ she replied. ‘It’s paid for.’ Her voice was incredibly sexy and I felt the hairs on the back of my neck stand on end. If she’d not been holding my hand, I would have been shaking. ‘Your friend said it’s a thank you for all the times you’ve been his wingman.’

I tried to protest, but she put her fingers to my lips and led me through a curtain into a private booth, where she sat me down and set some music.

She danced in front of me, swaying her perfect hips, bending over seductively and giving me sultry looks while I just sat leaking in my cage, wave after wave of precum was trickling into my boxers in a torrent, turning them into a sticky mess.

She climbed on top of me, straddling me and thrust her perfect body backwards and forwards. She slowly unclipped the corset and pressed her incredible breasts into my face as she swayed to the rock-metal anthem in the background. She ran her hands down my jean clad thighs as she stood back up and moved seductively around the small floor area in the booth. I trembled and gasped, she hooked her thumbs into her panties, lowered them slightly and raised them. She turned the other way, bent over in a dramatic fashion, the perfect curves of her ass adding to both my delight and discomfort. She stood and slowly lowered her black lace knickers to the floor, flicking them up onto my lap with a skillful kick.

She turned around and climbed back on top of me, her perfectly trimmed pussy inches from me - her gorgeous body pressed gently against me. She put her hands on the wall behind me and swayed backwards and forwards and side to side. The heady smells of her pussy, her perfume and her perspiration filled my head and I felt like I was going to faint.

She picked up the panties from my lap and gently pressed them into my face, stuffing them into my open mouth with a smile before giving me a kiss on the cheek and standing up.
‘You can keep them,’ she said with a wink before she scooped up her corset and disappeared through the curtain and presumably into the backstage area.

I sat there for a long moment recouperating, pressed the panties into my pocket and headed back to the bar, bracing myself for the inevitable banter that would be coming my way.

*        *        *

I called Kylie the next day and told her all about it. She laughed incessantly.
‘Imagine if she had known!’ she said, ‘Imagine if she had known about your little cock in your little cage.’

I asked for release, she denied me.
‘This is too funny!’ she said. ‘I can’t wait to tell Cat and Becky.’
‘What do I need to do for a release?’ I asked.
‘Oh, this one is easy,’ she said. ‘You just need to take some pictures.’
'I breathed a sigh of relief. ‘What of?’ I asked.
‘Well, you know how much I like big dicks? I want a picture of you with a big dick in your mouth. Then I want a picture of you with cum on your face. Only then will I unlock you.’

*        *        *

Kylie thought she was issuing me with a difficult challenge, but I was well aware of how I could achieve this task. Before she took control of me again, I’d hooked up with this guy a couple of times to give him blowjobs. He was seriously packing and had always been keen to get sucked off - so I dropped him a message that evening about hanging out and he told me he was free the following night after work and I could go round for a smoke and blow him.

The problem was, this guy was a bit of a dick and really got off on humiliation. I knew that the flat cage and telling him about being locked up by my ex would really get him going and it certainly did. We smoked a joint together while I told him my latest adventures. He insisted on seeing the cage and laughed and called me a ‘sissy bitch’ and ‘pathetic’ a few times before getting his cock out.

He sat back on the chair and had me kneel before his legs. I gave him my phone so he could take some pictures and videos for Kylie. I went to take hold of his cock but he pushed me away.
‘Beg for it,’ he said, holding up the camera.
‘Please let me suck your big cock,’ I pleaded.
‘You can do better than that.’
‘Please daddy! Please, I need to suck it, please!’
He laughed and gave me a nod.

I wrapped a hand around his huge shaft and began licking the head. I heard the click as he took a photo, I took him in my mouth and sucked on the head, taking as much in as I could, massaging with my tongue. He let out a soft, long moan as I hit the right spot and I felt him grow even harder inside my mouth.

‘Who is Kylie?’ he interrupted after a couple of minutes.
I removed his cock from my mouth, ‘My ex,’ I told him before turning my attention to his balls, which I licked and sucked on.
‘She’s sending you a video call.’
‘Mmmm?’

‘Hi, who is this?’ I heard Kylie’s voice out of my phone speaker.
‘I’m Ben,’ he replied. ‘I’ve got your ex licking my balls right now.’
Kylie laughed.

I glanced up and saw Ben pointing the camera right at me, I smiled, ran my tongue up his shaft and took his head in my mouth, stroking slowly with my big hand, getting him as sloppy as I could.
‘Wow,’ Kylie said, ‘Looks like he is doing a good job.’
Ben chuckled, ‘Yeah, he’s a good little bitch.’
‘Oh I know.’

Although I could feel the precum oozing from me,  I concentrated all of my attention on Ben’s cock, I worked it good, letting him slide down my throat as much as I could, using my tongue on his glans, licking his head while I stroked, feeling his precum mix with my saliva - all with Kylie watching on video.

Ben and Kylie exchanged comments from time to time, it was clear Kylie was masturbating while watching and Ben seemed to be enjoying that, though I had no idea how much she showed him.
‘I’m going to cum soon,’ he told her after a while. ‘Where do you want me to do it?’
Kylie made a thoughtful sound, ‘I think he deserves a facial, and then you can make him walk home with your cum all over him.’

Ben laughed, stood up over me while I knelt beneath him with my tongue out.
He stroked himself past the edge and sprayed me with his thick, hot cum. His first squirt hit me on the forehead and on my glasses, the second on my cheek and lips, the third and fourth straight into my mouth and the final dribble landed on my t-shirt.

He let Kylie get a good look at me, still kneeling and covered in cum. They both laughed, he sat back down and handed me my phone.
‘Off you go,’ he said, ‘I’ll call you next time I need target practice.’
I stood to my feet, cum dripping onto my lips, down my chin and onto my already messy top.
‘I want to see you do your cum walk,’ Kylie said, still on the video call.

I walked out of Ben’s flat, down the corridor and stairs and onto the street, Kylie chuckling and cheering to herself, my face sticky and my top now covered in the cum that was dripping onto it. I walked past a group of students outside a shop, who gasped and laughed, much to Kylie’s enjoyment.

‘Good boy,’ she told me. ‘You did well and I will come over tomorrow for your release,’ before she left me to complete my walk of shame alone.

 *        *        *

Kylie’s visit was delayed by a couple of days, which only added to my woes. When she came over, she was dressed up ready for a night out.
‘I’ve not got long, I’m supposed to be on my way to meet the girls.’

I stripped, let her unlock me and knelt in front of her, expecting to cum on her feet again.
‘Oh no,’ she said. ‘I want to see you get another facial.’
She made me lay down on the floor, with my back against the sofa and my legs in the air - so that my cock was over my face.
‘Off you go,’ she said.

It took me a while to get hard enough to jerk effectively, due to the effects of the cage and my humiliating position, but before long I was in a nice rhythm, with Kylie offering words of encouragement.
She glanced at her watch. ‘I’ve got to go in a minute, if you can’t cum soon I’ll have to lock you back up.’
I sped up and within a few seconds began spraying cum into my hair, face and chest.

Kylie laughed and clapped her hands, as I collapsed to one side.
‘Well, that will get my night off to a good start,’ she said as she locked me back up.
I looked up at her sheepishly. ‘When will I get unlocked again?’
‘I’m not sure. I’ll have to think of your next task. I might ask Becky and Cat if they have any ideas.

reddit.com
u/Afraid-Flan4278 — 2 days ago

More Torment From my ex Kylie [forced bi] [chastity] [humiliation]

A follow up to my previous story. This time my ex-girlfriend Kylie wants to see me suck cock in order to earn release, but only after I find myself in an uncomfortable situation at a bachelor party. This story is part of my latest collection. The final part of my adventures with Kylie will be posted in a week or so.

I didn’t hear from Kylie for almost two weeks and when she did it was just a quick check in. I asked her about a new task to be unlocked again and she just said ‘not yet’ and stopped replying.

A week or so after that, it was a friend’s twenty-first birthday and he had a big day planned. I hadn’t had a chance to think about it between work and my predicament. Being caged with little contact and no idea when I would be unlocked was a new level of intensity for me - it had stopped feeling like a game and started taking over my whole being. It made me constantly horny and submissive, craving any stimulation whatsoever. I wore panties everyday and used my largest dildo on myself in my free evenings, not because I had been told to but because I craved it.

When the birthday night out came around, I was little more than a quivering wreck. I’d managed a caged orgasm from anal play a few days before but it had made things worse, rather than better. I almost cancelled, but instead decided I would power on through. I showered, groomed and put on a decent outfit, including wearing boxers for the first time in weeks and headed out to meet the others.

We had a few drinks and some food and moved onto a small nightclub. There was a lot of laughter and banter and I got quite tipsy, which helped me forget about the cage. We headed on from the club, but I’d missed the conversation to decide where we were going and just followed along with everyone else until we stood outside the blackedout front of a strip club. I was hesitant, but everyone else was keen so I piled in with them, paid at the door and grabbed a drink from the bar.

I tried to keep myself to myself as the girls were moving around trying to encourage men to buy private dances. Their skimpy outfits were divine and I could feel myself leaking non stop in my cage, especially whenever any of them came to speak to me.

I turned down offers to buy dances a couple of times, but there was one girl that I couldn’t take my eyes off. Slim and pale with jet black hair, with a dyed red streak; she wore fishnets stockings, garters, some black laced panties and a very sexy black and red corset. She had some tattoos and piercings and was very much the type of girl I liked. I watched her from a distance as she spoke with various patrons, including Dan, one of my closest friends.

 Shortly after speaking with him, she meandered her way across the bar towards me with a sultry smile on her face. She didn’t say anything, she just took me by the hand and smiled, leading me towards the private area.
‘Umm, I’m not buying a dance,’ I stammered.

‘It’s okay,’ she replied. ‘It’s paid for.’ Her voice was incredibly sexy and I felt the hairs on the back of my neck stand on end. If she’d not been holding my hand, I would have been shaking. ‘Your friend said it’s a thank you for all the times you’ve been his wingman.’

I tried to protest, but she put her fingers to my lips and led me through a curtain into a private booth, where she sat me down and set some music.

She danced in front of me, swaying her perfect hips, bending over seductively and giving me sultry looks while I just sat leaking in my cage, wave after wave of precum was trickling into my boxers in a torrent, turning them into a sticky mess.

She climbed on top of me, straddling me and thrust her perfect body backwards and forwards. She slowly unclipped the corset and pressed her incredible breasts into my face as she swayed to the rock-metal anthem in the background. She ran her hands down my jean clad thighs as she stood back up and moved seductively around the small floor area in the booth. I trembled and gasped, she hooked her thumbs into her panties, lowered them slightly and raised them. She turned the other way, bent over in a dramatic fashion, the perfect curves of her ass adding to both my delight and discomfort. She stood and slowly lowered her black lace knickers to the floor, flicking them up onto my lap with a skillful kick.

She turned around and climbed back on top of me, her perfectly trimmed pussy inches from me - her gorgeous body pressed gently against me. She put her hands on the wall behind me and swayed backwards and forwards and side to side. The heady smells of her pussy, her perfume and her perspiration filled my head and I felt like I was going to faint.

She picked up the panties from my lap and gently pressed them into my face, stuffing them into my open mouth with a smile before giving me a kiss on the cheek and standing up.
‘You can keep them,’ she said with a wink before she scooped up her corset and disappeared through the curtain and presumably into the backstage area.

I sat there for a long moment recouperating, pressed the panties into my pocket and headed back to the bar, bracing myself for the inevitable banter that would be coming my way.

*        *        *

I called Kylie the next day and told her all about it. She laughed incessantly.
‘Imagine if she had known!’ she said, ‘Imagine if she had known about your little cock in your little cage.’

I asked for release, she denied me.
‘This is too funny!’ she said. ‘I can’t wait to tell Cat and Becky.’
‘What do I need to do for a release?’ I asked.
‘Oh, this one is easy,’ she said. ‘You just need to take some pictures.’
'I breathed a sigh of relief. ‘What of?’ I asked.
‘Well, you know how much I like big dicks? I want a picture of you with a big dick in your mouth. Then I want a picture of you with cum on your face. Only then will I unlock you.’

*        *        *

Kylie thought she was issuing me with a difficult challenge, but I was well aware of how I could achieve this task. Before she took control of me again, I’d hooked up with this guy a couple of times to give him blowjobs. He was seriously packing and had always been keen to get sucked off - so I dropped him a message that evening about hanging out and he told me he was free the following night after work and I could go round for a smoke and blow him.

The problem was, this guy was a bit of a dick and really got off on humiliation. I knew that the flat cage and telling him about being locked up by my ex would really get him going and it certainly did. We smoked a joint together while I told him my latest adventures. He insisted on seeing the cage and laughed and called me a ‘sissy bitch’ and ‘pathetic’ a few times before getting his cock out.

He sat back on the chair and had me kneel before his legs. I gave him my phone so he could take some pictures and videos for Kylie. I went to take hold of his cock but he pushed me away.
‘Beg for it,’ he said, holding up the camera.
‘Please let me suck your big cock,’ I pleaded.
‘You can do better than that.’
‘Please daddy! Please, I need to suck it, please!’
He laughed and gave me a nod.

I wrapped a hand around his huge shaft and began licking the head. I heard the click as he took a photo, I took him in my mouth and sucked on the head, taking as much in as I could, massaging with my tongue. He let out a soft, long moan as I hit the right spot and I felt him grow even harder inside my mouth.

‘Who is Kylie?’ he interrupted after a couple of minutes.
I removed his cock from my mouth, ‘My ex,’ I told him before turning my attention to his balls, which I licked and sucked on.
‘She’s sending you a video call.’
‘Mmmm?’

‘Hi, who is this?’ I heard Kylie’s voice out of my phone speaker.
‘I’m Ben,’ he replied. ‘I’ve got your ex licking my balls right now.’
Kylie laughed.

I glanced up and saw Ben pointing the camera right at me, I smiled, ran my tongue up his shaft and took his head in my mouth, stroking slowly with my big hand, getting him as sloppy as I could.
‘Wow,’ Kylie said, ‘Looks like he is doing a good job.’
Ben chuckled, ‘Yeah, he’s a good little bitch.’
‘Oh I know.’

Although I could feel the precum oozing from me,  I concentrated all of my attention on Ben’s cock, I worked it good, letting him slide down my throat as much as I could, using my tongue on his glans, licking his head while I stroked, feeling his precum mix with my saliva - all with Kylie watching on video.

Ben and Kylie exchanged comments from time to time, it was clear Kylie was masturbating while watching and Ben seemed to be enjoying that, though I had no idea how much she showed him.
‘I’m going to cum soon,’ he told her after a while. ‘Where do you want me to do it?’
Kylie made a thoughtful sound, ‘I think he deserves a facial, and then you can make him walk home with your cum all over him.’

Ben laughed, stood up over me while I knelt beneath him with my tongue out.
He stroked himself past the edge and sprayed me with his thick, hot cum. His first squirt hit me on the forehead and on my glasses, the second on my cheek and lips, the third and fourth straight into my mouth and the final dribble landed on my t-shirt.

He let Kylie get a good look at me, still kneeling and covered in cum. They both laughed, he sat back down and handed me my phone.
‘Off you go,’ he said, ‘I’ll call you next time I need target practice.’
I stood to my feet, cum dripping onto my lips, down my chin and onto my already messy top.
‘I want to see you do your cum walk,’ Kylie said, still on the video call.

I walked out of Ben’s flat, down the corridor and stairs and onto the street, Kylie chuckling and cheering to herself, my face sticky and my top now covered in the cum that was dripping onto it. I walked past a group of students outside a shop, who gasped and laughed, much to Kylie’s enjoyment.

‘Good boy,’ she told me. ‘You did well and I will come over tomorrow for your release,’ before she left me to complete my walk of shame alone.

 *        *        *

Kylie’s visit was delayed by a couple of days, which only added to my woes. When she came over, she was dressed up ready for a night out.
‘I’ve not got long, I’m supposed to be on my way to meet the girls.’

I stripped, let her unlock me and knelt in front of her, expecting to cum on her feet again.
‘Oh no,’ she said. ‘I want to see you get another facial.’
She made me lay down on the floor, with my back against the sofa and my legs in the air - so that my cock was over my face.
‘Off you go,’ she said.

It took me a while to get hard enough to jerk effectively, due to the effects of the cage and my humiliating position, but before long I was in a nice rhythm, with Kylie offering words of encouragement.
She glanced at her watch. ‘I’ve got to go in a minute, if you can’t cum soon I’ll have to lock you back up.’
I sped up and within a few seconds began spraying cum into my hair, face and chest.

Kylie laughed and clapped her hands, as I collapsed to one side.
‘Well, that will get my night off to a good start,’ she said as she locked me back up.
I looked up at her sheepishly. ‘When will I get unlocked again?’
‘I’m not sure. I’ll have to think of your next task. I might ask Becky and Cat if they have any ideas.

reddit.com
u/Afraid-Flan4278 — 2 days ago

Kylie orders me to suck cock [forced bi] [chastity] [humiliation]

A follow up to my previous story. This time my ex-girlfriend Kylie wants to see me suck cock in order to earn release, but only after I find myself in an uncomfortable situation at a bachelor party. This story is part of my latest collection, available on Kindle. The final part of my adventures with Kylie will be posted in a week or so.

I didn’t hear from Kylie for almost two weeks and when she did it was just a quick check in. I asked her about a new task to be unlocked again and she just said ‘not yet’ and stopped replying.

A week or so after that, it was a friend’s twenty-first birthday and he had a big day planned. I hadn’t had a chance to think about it between work and my predicament. Being caged with little contact and no idea when I would be unlocked was a new level of intensity for me - it had stopped feeling like a game and started taking over my whole being. It made me constantly horny and submissive, craving any stimulation whatsoever. I wore panties everyday and used my largest dildo on myself in my free evenings, not because I had been told to but because I craved it.

When the birthday night out came around, I was little more than a quivering wreck. I’d managed a caged orgasm from anal play a few days before but it had made things worse, rather than better. I almost cancelled, but instead decided I would power on through. I showered, groomed and put on a decent outfit, including wearing boxers for the first time in weeks and headed out to meet the others.

We had a few drinks and some food and moved onto a small nightclub. There was a lot of laughter and banter and I got quite tipsy, which helped me forget about the cage. We headed on from the club, but I’d missed the conversation to decide where we were going and just followed along with everyone else until we stood outside the blackedout front of a strip club. I was hesitant, but everyone else was keen so I piled in with them, paid at the door and grabbed a drink from the bar.

I tried to keep myself to myself as the girls were moving around trying to encourage men to buy private dances. Their skimpy outfits were divine and I could feel myself leaking non stop in my cage, especially whenever any of them came to speak to me.

I turned down offers to buy dances a couple of times, but there was one girl that I couldn’t take my eyes off. Slim and pale with jet black hair, with a dyed red streak; she wore fishnets stockings, garters, some black laced panties and a very sexy black and red corset. She had some tattoos and piercings and was very much the type of girl I liked. I watched her from a distance as she spoke with various patrons, including Dan, one of my closest friends.

 Shortly after speaking with him, she meandered her way across the bar towards me with a sultry smile on her face. She didn’t say anything, she just took me by the hand and smiled, leading me towards the private area.
‘Umm, I’m not buying a dance,’ I stammered.

‘It’s okay,’ she replied. ‘It’s paid for.’ Her voice was incredibly sexy and I felt the hairs on the back of my neck stand on end. If she’d not been holding my hand, I would have been shaking. ‘Your friend said it’s a thank you for all the times you’ve been his wingman.’

I tried to protest, but she put her fingers to my lips and led me through a curtain into a private booth, where she sat me down and set some music.

She danced in front of me, swaying her perfect hips, bending over seductively and giving me sultry looks while I just sat leaking in my cage, wave after wave of precum was trickling into my boxers in a torrent, turning them into a sticky mess.

She climbed on top of me, straddling me and thrust her perfect body backwards and forwards. She slowly unclipped the corset and pressed her incredible breasts into my face as she swayed to the rock-metal anthem in the background. She ran her hands down my jean clad thighs as she stood back up and moved seductively around the small floor area in the booth. I trembled and gasped, she hooked her thumbs into her panties, lowered them slightly and raised them. She turned the other way, bent over in a dramatic fashion, the perfect curves of her ass adding to both my delight and discomfort. She stood and slowly lowered her black lace knickers to the floor, flicking them up onto my lap with a skillful kick.

She turned around and climbed back on top of me, her perfectly trimmed pussy inches from me - her gorgeous body pressed gently against me. She put her hands on the wall behind me and swayed backwards and forwards and side to side. The heady smells of her pussy, her perfume and her perspiration filled my head and I felt like I was going to faint.

She picked up the panties from my lap and gently pressed them into my face, stuffing them into my open mouth with a smile before giving me a kiss on the cheek and standing up.
‘You can keep them,’ she said with a wink before she scooped up her corset and disappeared through the curtain and presumably into the backstage area.

I sat there for a long moment recouperating, pressed the panties into my pocket and headed back to the bar, bracing myself for the inevitable banter that would be coming my way.

*        *        *

I called Kylie the next day and told her all about it. She laughed incessantly.
‘Imagine if she had known!’ she said, ‘Imagine if she had known about your little cock in your little cage.’

I asked for release, she denied me.
‘This is too funny!’ she said. ‘I can’t wait to tell Cat and Becky.’
‘What do I need to do for a release?’ I asked.
‘Oh, this one is easy,’ she said. ‘You just need to take some pictures.’
'I breathed a sigh of relief. ‘What of?’ I asked.
‘Well, you know how much I like big dicks? I want a picture of you with a big dick in your mouth. Then I want a picture of you with cum on your face. Only then will I unlock you.’

*        *        *

Kylie thought she was issuing me with a difficult challenge, but I was well aware of how I could achieve this task. Before she took control of me again, I’d hooked up with this guy a couple of times to give him blowjobs. He was seriously packing and had always been keen to get sucked off - so I dropped him a message that evening about hanging out and he told me he was free the following night after work and I could go round for a smoke and blow him.

The problem was, this guy was a bit of a dick and really got off on humiliation. I knew that the flat cage and telling him about being locked up by my ex would really get him going and it certainly did. We smoked a joint together while I told him my latest adventures. He insisted on seeing the cage and laughed and called me a ‘sissy bitch’ and ‘pathetic’ a few times before getting his cock out.

He sat back on the chair and had me kneel before his legs. I gave him my phone so he could take some pictures and videos for Kylie. I went to take hold of his cock but he pushed me away.
‘Beg for it,’ he said, holding up the camera.
‘Please let me suck your big cock,’ I pleaded.
‘You can do better than that.’
‘Please daddy! Please, I need to suck it, please!’
He laughed and gave me a nod.

I wrapped a hand around his huge shaft and began licking the head. I heard the click as he took a photo, I took him in my mouth and sucked on the head, taking as much in as I could, massaging with my tongue. He let out a soft, long moan as I hit the right spot and I felt him grow even harder inside my mouth.

‘Who is Kylie?’ he interrupted after a couple of minutes.
I removed his cock from my mouth, ‘My ex,’ I told him before turning my attention to his balls, which I licked and sucked on.
‘She’s sending you a video call.’
‘Mmmm?’

‘Hi, who is this?’ I heard Kylie’s voice out of my phone speaker.
‘I’m Ben,’ he replied. ‘I’ve got your ex licking my balls right now.’
Kylie laughed.

I glanced up and saw Ben pointing the camera right at me, I smiled, ran my tongue up his shaft and took his head in my mouth, stroking slowly with my big hand, getting him as sloppy as I could.
‘Wow,’ Kylie said, ‘Looks like he is doing a good job.’
Ben chuckled, ‘Yeah, he’s a good little bitch.’
‘Oh I know.’

Although I could feel the precum oozing from me,  I concentrated all of my attention on Ben’s cock, I worked it good, letting him slide down my throat as much as I could, using my tongue on his glans, licking his head while I stroked, feeling his precum mix with my saliva - all with Kylie watching on video.

Ben and Kylie exchanged comments from time to time, it was clear Kylie was masturbating while watching and Ben seemed to be enjoying that, though I had no idea how much she showed him.
‘I’m going to cum soon,’ he told her after a while. ‘Where do you want me to do it?’
Kylie made a thoughtful sound, ‘I think he deserves a facial, and then you can make him walk home with your cum all over him.’

Ben laughed, stood up over me while I knelt beneath him with my tongue out.
He stroked himself past the edge and sprayed me with his thick, hot cum. His first squirt hit me on the forehead and on my glasses, the second on my cheek and lips, the third and fourth straight into my mouth and the final dribble landed on my t-shirt.

He let Kylie get a good look at me, still kneeling and covered in cum. They both laughed, he sat back down and handed me my phone.
‘Off you go,’ he said, ‘I’ll call you next time I need target practice.’
I stood to my feet, cum dripping onto my lips, down my chin and onto my already messy top.
‘I want to see you do your cum walk,’ Kylie said, still on the video call.

I walked out of Ben’s flat, down the corridor and stairs and onto the street, Kylie chuckling and cheering to herself, my face sticky and my top now covered in the cum that was dripping onto it. I walked past a group of students outside a shop, who gasped and laughed, much to Kylie’s enjoyment.

‘Good boy,’ she told me. ‘You did well and I will come over tomorrow for your release,’ before she left me to complete my walk of shame alone.

 *        *        *

Kylie’s visit was delayed by a couple of days, which only added to my woes. When she came over, she was dressed up ready for a night out.
‘I’ve not got long, I’m supposed to be on my way to meet the girls.’

I stripped, let her unlock me and knelt in front of her, expecting to cum on her feet again.
‘Oh no,’ she said. ‘I want to see you get another facial.’
She made me lay down on the floor, with my back against the sofa and my legs in the air - so that my cock was over my face.
‘Off you go,’ she said.

It took me a while to get hard enough to jerk effectively, due to the effects of the cage and my humiliating position, but before long I was in a nice rhythm, with Kylie offering words of encouragement.
She glanced at her watch. ‘I’ve got to go in a minute, if you can’t cum soon I’ll have to lock you back up.’
I sped up and within a few seconds began spraying cum into my hair, face and chest.

Kylie laughed and clapped her hands, as I collapsed to one side.
‘Well, that will get my night off to a good start,’ she said as she locked me back up.
I looked up at her sheepishly. ‘When will I get unlocked again?’
‘I’m not sure. I’ll have to think of your next task. I might ask Becky and Cat if they have any ideas.

reddit.com
u/Afraid-Flan4278 — 2 days ago

Another Reunion: Back in a cage for Kylie

The next instalment of my adventures with Kylie. We'd broken up, I'd had an encounter with her friend and now I find myself back in chastity for her. You can find the previous installments on my profile. This is all part of my second collection, based on true stories, and available on Kindle.

The months went by, I hooked up with a girl on a night out, and met a guy online who I fooled around with a couple of times. I made friends and caught up with old ones, I was enjoying my job and my flat and life was ticking by nicely. I’d get my toys out for a play sometimes and occasionally lock myself in chastity for a while, but only ever for a few days at a time. I got into self-bondage and bought a timer lock, which provided me with a lot of fun during my evenings in. An hour in a hogtie with a vibrating buttplug is a good way to defeat boredom.

Then, one afternoon at work, I had a text from my ex girlfriend/mistress Kylie, asking if I wanted to go for a coffee at the weekend. I left it for a few hours before replying that it would be nice to catch up and we made plans to meet at a coffee shop in the centre of town.

Saturday rolled around and after giving my flat a good clean and tidy, which I did every Saturday morning, I showered, groomed and chose an outfit that I thought I looked good in, hesitating before putting my underwear on. I looked at the relatively new cotton boxer shorts in my hand, shook my head and put them back in the drawer and instead put on a lacey black thong, remembering Kylie’s preference for seeing me in female underwear. I finished getting dressed, checked myself in the mirror and walked into town, giving myself plenty of time to arrive at the chosen coffee shop early.

Kylie was there only a few minutes after me, I bought her a coffee and we sat in a quiet corner and caught up. She was doing well in her final year at uni and had started looking at options for after she graduated. I told her about my job and flat and we swapped a few stories about our friends.

I bought us each another coffee and when I returned to the table with them, she smiled softly and asked me if I knew why she asked to meet up.
‘I assumed you just wanted to catch up,’ I replied.
‘Well, with your birthday coming up next week, I wanted to give you something,’ she explained. ‘Last year I took you to that dungeon, the year before I gave you that first chastity cage. I didn’t want to let this year pass without a gift.’

She placed a small box on the table, wrapped with silver wrapping paper and a red ribbon.
‘You really didn’t have to,’ I told her.
‘I wanted to,’ she insisted. ‘Open it.’

I undid the bow and unfolded the neatly wrapped paper, with a feeling that I knew what would be inside. I opened the box and, sure enough, there was a new chastity cage. It was a small, flat style and looked pretty intense. I took a deep breath and looked at Kylie with a furrowed brow.

‘Is this your way of saying you want to get back together,’ I asked her.
‘No, not at all. I have no interest in fucking you or even particularly spending long periods of time together. I just think you should be in a cage and I should have the key.’
Stunned, I stared at her speechless for a moment.
‘And you know it too,’ she said, leaning in close. ‘I saw your panties when you got up a minute ago, you know what you are.’

The whole situation was incredibly arousing and my hands were trembling slightly.
‘How long for?’ I asked.
‘As long as I feel like it. I’ll send you tasks to do, maybe have you come over and worship me occasionally. You will get release every now and then, maybe. You won’t get to fuck me though, those days are long over.’
‘What if I get a girlfriend?’
‘Then you can send her to me and she can beg for it.’
‘What if if I -’
‘No more what ifs,’ she interrupted. ‘When a decision needs to be made, I will make it. Now go to the toilet, put on the cage and give me the key like a good boy.’
I swallowed my fear and took a deep breath: ‘Yes mistress.’

It took me a few minutes in the toilet to get the flat cage on, I’d never worn one before and I was pretty aroused, which made the task difficult. When I returned to the cage, Kylie was on her phone, she looked up at me and smiled as she put her phone back in her bag.
‘Is it on?’ she asked as I sat down.
‘Yes,’ I said, handing the key to her.
She took it from me, looked at it and smiled before putting it in her bra.

‘Good boy,’ she said, standing up. ‘I guess I will see you around.’
‘Umm,’ I stammered, rising from my chair. ‘You’re going?’
‘Yeah,’ she replied. ‘We’re done here. I’ll call you soon.’
She kissed me softly on the cheek, shot me a wicked grin and walked out of the coffee shop.
I sat back down in my chair, stared at the bottom of my mug and tried to process what had just happened.

*        *        *

I sent Kylie a text a few days later, trying to sound her out but appearing casual. It took her three days to reply.

‘Sorry, been busy. I’ll call you soon x.’ was all it said.

 A week later, on my birthday, she called me up and asked how I was getting on with the cage.
‘Umm, yeah, I’m getting used to it.’ I told her. ‘I’m just horny all the time.’
‘Good, that will help you focus on your tasks.’
‘What are they?’ I asked.
‘You will find out soon.’

I tried to play it cool and avoided texting her for a week or so and I was just about to crack when she sent me my first task, which involved wearing panties and a buttplug on a night out - just as she had made me do before. I fulfilled it with ease and sent her the pictures to prove it.

Christmas passed and so did New Years Eve (where once again, I was made to go out in panties and a larger plug). The weeks went by and sometimes I wouldn’t hear from her for days, weeks at a time. I learnt to be patient, wait for her instructions and fulfil them. I abandoned any notion of dating and leant into my role - even sending her flowers and chocolates occasionally, which seemed to keep her sweet.

About two months after my initial lock up, after fulfilling a plethora of minor humiliations, I got a message that explained that I had an opportunity to earn release: ‘Go out and buy yourself a girly outfit. A skirt, stockings, crop top and some shoes. I want a picture of you wearing them.’

It took me about two hours to walk into town, make the purchases, walk home and put them on. I sent her the pictures.
‘Good boy. That was quick. I’ve sent you a parcel, let me know when it arrives.’

Two days later a parcel arrived, a blonde wig, make up, a collar and a bra. I called her straight away.
‘Good,’ she said. ‘I want you to make yourself look as feminine as possible and send me a picture of you all dressed up in a public place.’

The thought terrified me and I tried to protest. She explained that this was an opportunity for release and she had no idea when the next one would be, so I complied with her orders. I shaved, did the make up as best I could and put on some panties, stockings, bra and crop top underneath jeans and a hoody. The rest of the items I placed in my bag and headed out late at night.

I walked to a city park, found a secluded spot, removed my boy clothes and put on the rest of the outfit. I set my camera to a timer, placed it on a bench and stepped back to take a picture underneath a street light. I tried some different poses and then, hearing voices, ran into some nearby bushes, hastily changing back into my boy clothes before walking home.

Kylie laughed when I told her about it and sent her the pictures.
‘Good job,’ she said. ‘I will come over yours tomorrow evening.’

She arrived about half an hour later, which I imagined was to keep me on edge. I answered the door wearing nothing but my cage, just as she had ordered and made her a drink. She sat on the sofa and had me kiss her tight clad feet and legs for several long minutes before she removed her tights, lifted her skirt and let me lick her to orgasm.

‘Good boy,’ she said, producing the key necklace I had purchased her so long ago from her cleavage, she opened it, pulled out the key and waved it around in a teasing manner while I knelt in front of her.

She ordered me to stand and put my hands behind my back. She unlocked the cage, removed the front part but left the ring and the strap in place.
‘Now kneel,’ she said.
I knelt back down in front of her with my hands still behind my back and my cock struggling to rise.
Kylie leaned back, rubbed her foot against my shaft and ran her big toe from base to tip. ‘Don’t think I’m touching it with my hands,’ she laughed playfully.

She gave my balls a gentle kick. ‘Is this what Cat did?’ she chuckled.
‘You know about that?’ I said, shocked.
‘Of course, it’s one of the reasons I locked you up again. I can’t have you going around fucking beautiful women like her.’ She kicked me again slightly harder but still playful.
‘Were you cross at her?’ I asked.
‘A little,’ she said, ‘But I made sure she made it up to me.’
‘How?’
She kicked me again, harder this time. ‘That doesn’t concern you. Now, I’m going to give you one minute to make yourself cum on my feet, then you are going to lick it up and that cage goes back on. Understand?’
‘Yes mistress.’
‘Go.’

I masturbated fast and hard and within about thirty seconds shot a huge load across Kylie’s feet, which she held under my cock. Kylie laughed and lowered her feet carefully to the floor. I looked up at her but she didn’t say anything, she just watched me and waited.

I bent down low, took a deep breath and began licking my cum from her feet, drop by drop until it was all gone and I had swallowed it all. After I was finished, she ordered me to my feet and put the cage back on and the key back into the necklace.

She stood up and went to the bathroom to wash her feet and put her tights back on while I sat waiting on the floor. When she returned, she gave me a playful headrub and told me she would be in contact again soon. I went to stand up, but she playfully put a hand on my shoulder to stop me and instead bent over to kiss my forehead.

‘Goodbye little puppy,’ she whispered.

reddit.com
u/Afraid-Flan4278 — 6 days ago

Another Reunion: Back in a cage for Kylie [chastity] [cei] [long term]

The next instalment of my adventures with Kylie. We'd broken up, I'd had an encounter with her friend and now I find myself back in chastity for her. You can find the previous instalments on my profile.

The months went by, I hooked up with a girl on a night out, and met a guy online who I fooled around with a couple of times. I made friends and caught up with old ones, I was enjoying my job and my flat and life was ticking by nicely. I’d get my toys out for a play sometimes and occasionally lock myself in chastity for a while, but only ever for a few days at a time. I got into self-bondage and bought a timer lock, which provided me with a lot of fun during my evenings in. An hour in a hogtie with a vibrating buttplug is a good way to defeat boredom.

Then, one afternoon at work, I had a text from my ex girlfriend/mistress Kylie, asking if I wanted to go for a coffee at the weekend. I left it for a few hours before replying that it would be nice to catch up and we made plans to meet at a coffee shop in the centre of town.

Saturday rolled around and after giving my flat a good clean and tidy, which I did every Saturday morning, I showered, groomed and chose an outfit that I thought I looked good in, hesitating before putting my underwear on. I looked at the relatively new cotton boxer shorts in my hand, shook my head and put them back in the drawer and instead put on a lacey black thong, remembering Kylie’s preference for seeing me in female underwear. I finished getting dressed, checked myself in the mirror and walked into town, giving myself plenty of time to arrive at the chosen coffee shop early.

Kylie was there only a few minutes after me, I bought her a coffee and we sat in a quiet corner and caught up. She was doing well in her final year at uni and had started looking at options for after she graduated. I told her about my job and flat and we swapped a few stories about our friends.

I bought us each another coffee and when I returned to the table with them, she smiled softly and asked me if I knew why she asked to meet up.
‘I assumed you just wanted to catch up,’ I replied.
‘Well, with your birthday coming up next week, I wanted to give you something,’ she explained. ‘Last year I took you to that dungeon, the year before I gave you that first chastity cage. I didn’t want to let this year pass without a gift.’

She placed a small box on the table, wrapped with silver wrapping paper and a red ribbon.
‘You really didn’t have to,’ I told her.
‘I wanted to,’ she insisted. ‘Open it.’

I undid the bow and unfolded the neatly wrapped paper, with a feeling that I knew what would be inside. I opened the box and, sure enough, there was a new chastity cage. It was a small, flat style and looked pretty intense. I took a deep breath and looked at Kylie with a furrowed brow.

‘Is this your way of saying you want to get back together,’ I asked her.
‘No, not at all. I have no interest in fucking you or even particularly spending long periods of time together. I just think you should be in a cage and I should have the key.’
Stunned, I stared at her speechless for a moment.
‘And you know it too,’ she said, leaning in close. ‘I saw your panties when you got up a minute ago, you know what you are.’

The whole situation was incredibly arousing and my hands were trembling slightly.
‘How long for?’ I asked.
‘As long as I feel like it. I’ll send you tasks to do, maybe have you come over and worship me occasionally. You will get release every now and then, maybe. You won’t get to fuck me though, those days are long over.’
‘What if I get a girlfriend?’
‘Then you can send her to me and she can beg for it.’
‘What if if I -’
‘No more what ifs,’ she interrupted. ‘When a decision needs to be made, I will make it. Now go to the toilet, put on the cage and give me the key like a good boy.’
I swallowed my fear and took a deep breath: ‘Yes mistress.’

It took me a few minutes in the toilet to get the flat cage on, I’d never worn one before and I was pretty aroused, which made the task difficult. When I returned to the cage, Kylie was on her phone, she looked up at me and smiled as she put her phone back in her bag.
‘Is it on?’ she asked as I sat down.
‘Yes,’ I said, handing the key to her.
She took it from me, looked at it and smiled before putting it in her bra.

‘Good boy,’ she said, standing up. ‘I guess I will see you around.’
‘Umm,’ I stammered, rising from my chair. ‘You’re going?’
‘Yeah,’ she replied. ‘We’re done here. I’ll call you soon.’
She kissed me softly on the cheek, shot me a wicked grin and walked out of the coffee shop.
I sat back down in my chair, stared at the bottom of my mug and tried to process what had just happened.

*        *        *

I sent Kylie a text a few days later, trying to sound her out but appearing casual. It took her three days to reply.

‘Sorry, been busy. I’ll call you soon x.’ was all it said.

 A week later, on my birthday, she called me up and asked how I was getting on with the cage.
‘Umm, yeah, I’m getting used to it.’ I told her. ‘I’m just horny all the time.’
‘Good, that will help you focus on your tasks.’
‘What are they?’ I asked.
‘You will find out soon.’

I tried to play it cool and avoided texting her for a week or so and I was just about to crack when she sent me my first task, which involved wearing panties and a buttplug on a night out - just as she had made me do before. I fulfilled it with ease and sent her the pictures to prove it.

Christmas passed and so did New Years Eve (where once again, I was made to go out in panties and a larger plug). The weeks went by and sometimes I wouldn’t hear from her for days, weeks at a time. I learnt to be patient, wait for her instructions and fulfil them. I abandoned any notion of dating and leant into my role - even sending her flowers and chocolates occasionally, which seemed to keep her sweet.

About two months after my initial lock up, after fulfilling a plethora of minor humiliations, I got a message that explained that I had an opportunity to earn release: ‘Go out and buy yourself a girly outfit. A skirt, stockings, crop top and some shoes. I want a picture of you wearing them.’

It took me about two hours to walk into town, make the purchases, walk home and put them on. I sent her the pictures.
‘Good boy. That was quick. I’ve sent you a parcel, let me know when it arrives.’

Two days later a parcel arrived, a blonde wig, make up, a collar and a bra. I called her straight away.
‘Good,’ she said. ‘I want you to make yourself look as feminine as possible and send me a picture of you all dressed up in a public place.’

The thought terrified me and I tried to protest. She explained that this was an opportunity for release and she had no idea when the next one would be, so I complied with her orders. I shaved, did the make up as best I could and put on some panties, stockings, bra and crop top underneath jeans and a hoody. The rest of the items I placed in my bag and headed out late at night.

I walked to a city park, found a secluded spot, removed my boy clothes and put on the rest of the outfit. I set my camera to a timer, placed it on a bench and stepped back to take a picture underneath a street light. I tried some different poses and then, hearing voices, ran into some nearby bushes, hastily changing back into my boy clothes before walking home.

Kylie laughed when I told her about it and sent her the pictures.
‘Good job,’ she said. ‘I will come over yours tomorrow evening.’

She arrived about half an hour later, which I imagined was to keep me on edge. I answered the door wearing nothing but my cage, just as she had ordered and made her a drink. She sat on the sofa and had me kiss her tight clad feet and legs for several long minutes before she removed her tights, lifted her skirt and let me lick her to orgasm.

‘Good boy,’ she said, producing the key necklace I had purchased her so long ago from her cleavage, she opened it, pulled out the key and waved it around in a teasing manner while I knelt in front of her.

She ordered me to stand and put my hands behind my back. She unlocked the cage, removed the front part but left the ring and the strap in place.
‘Now kneel,’ she said.
I knelt back down in front of her with my hands still behind my back and my cock struggling to rise.
Kylie leaned back, rubbed her foot against my shaft and ran her big toe from base to tip. ‘Don’t think I’m touching it with my hands,’ she laughed playfully.

She gave my balls a gentle kick. ‘Is this what Cat did?’ she chuckled.
‘You know about that?’ I said, shocked.
‘Of course, it’s one of the reasons I locked you up again. I can’t have you going around fucking beautiful women like her.’ She kicked me again slightly harder but still playful.
‘Were you cross at her?’ I asked.
‘A little,’ she said, ‘But I made sure she made it up to me.’
‘How?’
She kicked me again, harder this time. ‘That doesn’t concern you. Now, I’m going to give you one minute to make yourself cum on my feet, then you are going to lick it up and that cage goes back on. Understand?’
‘Yes mistress.’
‘Go.’

I masturbated fast and hard and within about thirty seconds shot a huge load across Kylie’s feet, which she held under my cock. Kylie laughed and lowered her feet carefully to the floor. I looked up at her but she didn’t say anything, she just watched me and waited.

I bent down low, took a deep breath and began licking my cum from her feet, drop by drop until it was all gone and I had swallowed it all. After I was finished, she ordered me to my feet and put the cage back on and the key back into the necklace.

She stood up and went to the bathroom to wash her feet and put her tights back on while I sat waiting on the floor. When she returned, she gave me a playful headrub and told me she would be in contact again soon. I went to stand up, but she playfully put a hand on my shoulder to stop me and instead bent over to kiss my forehead.

‘Goodbye little puppy,’ she whispered.

reddit.com
u/Afraid-Flan4278 — 6 days ago

Running into my ex's friend.

Another true story from my collection - you can view past stories on my profile.

My girlfriend/mistress and I broke up and I find myself running into one of her friends on a night out. Little did I know how that would transpire and that it would ruin my chances with a girl I really liked. More coming soon.

Towards the end of my final year at uni, Kylie and I broke up. We had started bickering quite a lot and put the kinky side of our relationship on hold. When that happened, we found we didn’t really have anything else in common and just seemed to get on each others’ nerves all the time.

I was devastated when she finally called it a day, but threw myself into the last big push at university and got through those difficult first couple of months apart. I started to grow very close to a friend of mine, a woman named Lisa. She’d had relationship troubles of her own and was also coming out of a long-term relationship. Lisa was beautiful, a raven-haired rock chick with long legs, perfect curves and a smile that made my heart flutter. It seemed inevitable that something would happen between us but we were both taking it slow, not wanting to rush into anything new without being ready.

This all happened around the time I was finishing university and I ended up moving back to my hometown very suddenly to take up a lucrative job offer. Undeterred, Lisa and I were still texting every day and speaking regularly. I really liked her and sometimes I thought she really liked me too, though at other times I was uncertain – crippled by some self-esteem issues and a conviction that a woman as beautiful as that would never be interested in me, especially when I knew there were plenty of other guys interested in her. The signs that she was interested were all there, it was just a case of building up the courage, taking the chance and hoping for the best.

We made plans to hang out and I took a week off, scheduled for about two months after I’d moved. I booked the time off and began excitedly counting down the days. Then, something happened that ruined everything.

A couple of nights before I was due to get the train to see Lisa, on a night out with some of my old school friends, disaster struck in the form of my ex’s best friend Cat. Cat and I had never got on well when Kylie and I were together and she had taken great pleasure in seeing Kylie humiliate me on New Year’s Eve. Cat was a pocket rocket, short, slightly on the thick side with short wavy brown hair and cutting blue eyes. She rarely smiled and when she did it was usually in a bitchy, sarcastic way. I’d not seen her in at least six months and running into her on a night out was a shock. My friend had been trying to chat up one of her friends and more or less dragged the group onto the dance floor to join their group.

As soon as I saw Cat was in the group, I looked around with a panicked expression on my face. She clearly saw, because she lent over to me and whispered, ‘Don’t worry – I’m with work friends. Kylie isn’t here.’

I breathed a sigh of relief and, to my surprise, Cat didn’t move away, she stayed close to me while she danced, casually looking around the room and sucking the last of her drink through a straw.

‘Would you like another drink?’ I asked her.
‘Old habits die hard,’ she smiled, handing me her glass.
I bought her a drink and we wandered back to the dance floor. One of my friends, who had no idea who she was, flashed me a grin.

We continued dancing close to each other, every now and then catching each other’s eye awkwardly. In a lull between songs, she leaned in close and whispered, ‘Are you wearing a cage tonight?’. A reminder that she knew all about Kylie’s role as my mistress.
‘No,’ I replied.
‘Shame.’

We danced together for a while and I bought her a couple more drinks. She made a couple of jokes about my friends and hers and I actually found them funny. As the night was going on, I was starting to find this girl I’d previously only ever found to be annoying and bitchy, to actually be quite fun and kind of hot. One of my friends left with one of hers and the rest of the guys were mostly interested in other groups of girls by this point, but Cat and I carried on dancing, drinking and laughing together. She made a few references to my kinky escapades, asking if I still had my toys and if I’d found a new mistress. I answered yes and no, respectively.

As we became more intoxicated, we started dancing closer and closer. At first it seemed like a joke, until all of a sudden, with our bodies pressed against each other during a particularly sexy song, our eyes met and, with our faces mere inches apart we started to lean in for a kiss, when all of a sudden, we both got shoved unceremoniously aside as two men started fighting on the dance floor. I protectively put my arm across her, guiding her away from the sudden violence. We moved quickly and carefully away from the dance floor, while the security staff manhandled the offenders outside.

We chuckled together, ‘That was close,’ I said. But then she asked me where I was staying tonight, so I told her, ‘I moved back to town a few weeks ago. I’ve got a flat about 10 minutes from here.’
She smiled, ‘Let’s go then. I want to see your toy collection.’

We finished our drinks and left the club, just after midnight. We chatted quite generally during the walk to my place, she asked about my friend that had gone off with her friend. I told her that he was alright. She asked about my new job and I asked about hers. Neither of us mentioned Kylie and neither of us mentioned anything kinky. We just chatted and laughed and joked until we were on the landing outside my flat, where she grabbed me and kissed me forcefully. I offered no resistance, enjoying her tongue pressing against mine and her hand on my neck.

She broke away and nodded towards the door. I pulled out the key, opened the door and held it open for her. She crossed the room confidently and sat herself down on the sofa, kicking her heels off and leaning back playfully. I closed the door behind me, kicked off my own shoes and began crossing the room, when I was about to join her on the sofa, she held up her hand to stop me and said, ‘Get me a drink,’ her demanding tone reminiscent of Kylie’s and unlocking the submissive in me.

I crossed to the kitchen area and poured a gin and tonic for both of us and returned to the sofa. I put my drink down and made moves to kiss her again but she stopped me and pointed towards her feet.
‘You know what to do,’ she told me. 

I knelt on the floor as she put her feet up on the sofa and began kissing them while I caressed her calves, she watched me carefully as she sipped her drink, an evil grin on her face. I worked my way up her legs, convinced that I wouldn’t have much trouble slipping off her panties from under her dress and that I wouldn’t need to play the submissive for long. I was horny and the idea of getting to fuck my ex’s bitchy friend was fun, but just as my hands slipped under her dress, my fingers barely touching the straps of her underwear, she gently pushed me off her. ‘I think it’s time to show me your toys,’ she told me.

I hesitated, but it was clear there was still some fun to be had, so I took her by the hand, pulled her up from the sofa and led her into my bedroom.

My flat was on the top floor of an old building that had been converted, the bedroom had a sloped ceiling and a beautiful wooden beam. The décor was simple, just a student bookshelf, an armchair, a dresser and a built-in wardrobe. The room was surprisingly large and I’d moved the metal-framed, double bed against one wall, to create extra floor space.

I led Cat over to the wardrobe, opened it up and pulled out a large, black chest. I took the key out from the dresser drawer and opened my kinky repository. I stepped back as Cat crouched down and began looking through the box. I let my eyes wander down her back, across her ass and bare legs and down to her feet.

‘What am I doing?’ I asked myself, ‘I’m supposed to be getting together with Lisa and I’m fooling around with my ex’s bitchy friend.’ Logic and reason had been totally unwound by horniness and submission; a situation cemented by the look on her face when she turned around with a pair of handcuffs in her hand.

‘Let’s try these,’ she told me, with a wicked smile reminiscent of my ex-mistress.
‘Okay,’ I replied,
‘Where do you want me?’
‘Top off and under the beam.’
I complied, removing my t-shirt and allowing her to cuff me to the ceiling beam. I figured I would get some light teasing, maybe a blowjob, but that with so little experience of BDSM she would quickly release me and I would get to give her a good fucking.

Once I was secured, however, she quickly returned to the box and produced a simple device I had built myself – a short wooden plank with two metal eyes at either end.
‘What’s this for?’ she asked innocently.
‘It’s a spreader bar. You can attach ankle cuffs and force someone’s legs apart.’
‘That sounds fun,’ she replied, picking out the ankle cuffs and walking back towards me.

She undid my jeans and pulled them off of me roughly, followed by my boxers. My unleashed cock stood to attention but she barely seemed to pay any attention to it, even when she knelt in front of me, her face mere inches away. Instead, she focussed on placing the cuffs around my ankles and attaching the spreader bar, forcing me to stand with feet little over shoulder width apart.
‘Much better,’ she smiled as she stood up, ‘What else can we find?’

The next item she produced was a ball-gag, which she forced into my mouth with ease. I was beginning to have my doubts when she followed it up with some nipple clamps. The questions had stopped, she suddenly seemed to know exactly what everything was and what to do with it. My fears were confirmed when she pulled some rope at the box and began tying my cock and balls up in a tight and complex arrangement that left them painful, exposed and purple. She pulled over a chair and sat across from me, with a riding crop in her hand and a smile on her face.

‘Confession time,’ she began, ‘when Kylie showed us the kind of things you two were into at her house, I was intrigued. In fact, I became obsessed and started researching for myself.’
She paused to strike my hard, bound cock with the crop.
‘I asked Kylie every question I could think of and started watching all these porn videos of women torturing men.’
She struck again, my gasp of pain muffled by the gag.
‘And I loved it. It turned me on so much.’
She stood up and walked around the back of me.
‘Kylie got off on control and humiliation and I know you got off on that too.’
She struck my arse hard with the crop – harder than Kylie had ever whipped me. The initial sting was soon surpassed by a throbbing sensation that wouldn’t subside.
‘But that’s not what I wanted. It was pain I wanted to inflict.’
She struck again, harder than before.
‘I watched hours of videos, read every book and article I could find,’ she walked back around the front of me, her hips swaying seductively, ‘and I loved it.’
She pressed her body close to mine, I was trembling with fear, excitement and pain. She moved away from me, whipping my cock once more with a smile on her face.
‘I wanted to find a guy I could try all these things on, a guy I could hurt,’ she continued, ‘But there was no one. I would fantasise about it, I would masturbate thinking about having a slave of my own – just like Kylie had you, a slave I could torture. I tried websites, but every guy wanted something else or they would just talk and talk. I didn’t want to talk, I didn’t want a boyfriend, I didn’t want to fuck.’ She looked me dead in the eye, ‘I just wanted to hurt someone.’

She walked around behind me again, whipping my arse and thighs several times with harsh, stinging strikes. When she came back around the front, she walked past me and placed the whip on the chair before turning to face me. She unzipped her dress and let it sink slowly to the floor, her matching black underwear a sexy contrast to her pale skin.
‘And then tonight, I saw you.’ She smiled, ‘And I thought, ‘perfect – he’s submissive, he’s got the toys, all I’ve got to do is convince him to take me to his and I can do whatever I like.’
With that, she gave me a swift kick to the balls. I gasped in pain, my groans muffled by the gag.
‘So, here’s the deal,’ she explained, picking up a paddle from the chest, ‘If you let me do whatever I like to you, when I’m finished – you can fuck me.

I stared at her with disbelief, the precum dripping from my cock matched by the drool dripping from the gag. ‘You can fuck me however you want. I’ll suck your dick and call it ice-cream, if you like. And that’s it. You let me hurt you, I’ll let you do whatever you want with me.’
She walked behind me again and struck each of my ass cheeks three or four times with the paddle, making me whimper as each strike made the welts from the crop throb once more.
‘Of course, you could say no and there’s nothing really to stop me carrying on anyway,’ she said, as she moved back in front of me, her hand gently running over my bound cock. ‘But that’s a risk you’ll have to take.’ She squeezed my bound package hard and I tried to lurch forward but the restraints held me in place.
‘So, what do you say?’ I nodded my approval, tears in my eyes from the squeezing.

She let go, took a step back and kicked me again between the legs. I groaned and she smiled her evil smile. She kept me tied to the beam for around two hours of whipping, spanking and attacks on my genitals with various objects and body parts. She had mercy on me a few times, giving me a break from the gag and some water to drink every twenty minutes or so. When she let me down, I thought it was over, but she dragged me to the bed, tied me down and dripped hot candle wax over me, covering my chest, my cock and my balls. She then decided that a riding crop was the best implement to remove it.

After that, she found some clothes pegs, which she tied together with string and clipped onto my ballsack. She laughed when I winced as she pulled them off. It was around half four in the morning when she untied me for the last time, I was covered in scratches, bruises and welts. My genitals were sore and whatever position I lay in was uncomfortable.

We slept for a few hours and in the morning, I made good on her promise to let me do what I wanted with her. I was so sore that it made fucking her every way I could imagine difficult and she seemed to enjoy my pain more than I was enjoying the sex. She had several short, snakelike orgasms before, after fucking her tight body from behind, I was finally able to manhandle her to her knees and finish off in her mouth.

She showered and left me to clear up the mess. I slept for a while in the afternoon, and it was only in the evening that I remembered that the next day was my trip to visit Lisa. I was distraught when I realised the predicament I was now in. My body was covered in the physical evidence of my encounter with Cat – scratches and bruises were all over my back, arse, legs and chest. There was no chance of allowing anything to happen with Lisa without very awkward conversations, probably one that would prevent anything happening anyway.

That weekend, I hung out with Lisa and our mutual friends and I played it as safe as I could. I was friendly and fun, I flirted back when she flirted with me but on the two or three occasions she made a move, I played dumb and didn’t let anything happen. I figured I could go back in a couple of weeks, when the marks had faded and make my move then. Unfortunately, that wasn’t to be.

Around a week after my visit, I found out that Lisa had started seeing someone else. A mutual friend told me that she thought I wasn’t interested and met someone at a gig and that was that. My chances of landing an incredibly sexy girl that I really liked were ruined because I fell into the trap of my ex’s sadistic friend.

reddit.com
u/Afraid-Flan4278 — 18 days ago

Running Into My Ex's Friend [ballbusting] [femdom] [bondage]

Another true story from my collection - you can view past stories on my profile.

My girlfriend/mistress and I broke up and I find myself running into one of her friends on a night out. Little did I know how that would transpire and that it would ruin my chances with a girl I really liked. More coming soon.

Towards the end of my final year at uni, Kylie and I broke up. We had started bickering quite a lot and put the kinky side of our relationship on hold. When that happened, we found we didn’t really have anything else in common and just seemed to get on each others’ nerves all the time.

I was devastated when she finally called it a day, but threw myself into the last big push at university and got through those difficult first couple of months apart. I started to grow very close to a friend of mine, a woman named Lisa. She’d had relationship troubles of her own and was also coming out of a long-term relationship. Lisa was beautiful, a raven-haired rock chick with long legs, perfect curves and a smile that made my heart flutter. It seemed inevitable that something would happen between us but we were both taking it slow, not wanting to rush into anything new without being ready.

This all happened around the time I was finishing university and I ended up moving back to my hometown very suddenly to take up a lucrative job offer. Undeterred, Lisa and I were still texting every day and speaking regularly. I really liked her and sometimes I thought she really liked me too, though at other times I was uncertain – crippled by some self-esteem issues and a conviction that a woman as beautiful as that would never be interested in me, especially when I knew there were plenty of other guys interested in her. The signs that she was interested were all there, it was just a case of building up the courage, taking the chance and hoping for the best.

We made plans to hang out and I took a week off, scheduled for about two months after I’d moved. I booked the time off and began excitedly counting down the days. Then, something happened that ruined everything.

A couple of nights before I was due to get the train to see Lisa, on a night out with some of my old school friends, disaster struck in the form of my ex’s best friend Cat. Cat and I had never got on well when Kylie and I were together and she had taken great pleasure in seeing Kylie humiliate me on New Year’s Eve. Cat was a pocket rocket, short, slightly on the thick side with short wavy brown hair and cutting blue eyes. She rarely smiled and when she did it was usually in a bitchy, sarcastic way. I’d not seen her in at least six months and running into her on a night out was a shock. My friend had been trying to chat up one of her friends and more or less dragged the group onto the dance floor to join their group.

As soon as I saw Cat was in the group, I looked around with a panicked expression on my face. She clearly saw, because she lent over to me and whispered, ‘Don’t worry – I’m with work friends. Kylie isn’t here.’

I breathed a sigh of relief and, to my surprise, Cat didn’t move away, she stayed close to me while she danced, casually looking around the room and sucking the last of her drink through a straw.

‘Would you like another drink?’ I asked her.
‘Old habits die hard,’ she smiled, handing me her glass.
I bought her a drink and we wandered back to the dance floor. One of my friends, who had no idea who she was, flashed me a grin.

We continued dancing close to each other, every now and then catching each other’s eye awkwardly. In a lull between songs, she leaned in close and whispered, ‘Are you wearing a cage tonight?’. A reminder that she knew all about Kylie’s role as my mistress.
‘No,’ I replied.
‘Shame.’

We danced together for a while and I bought her a couple more drinks. She made a couple of jokes about my friends and hers and I actually found them funny. As the night was going on, I was starting to find this girl I’d previously only ever found to be annoying and bitchy, to actually be quite fun and kind of hot. One of my friends left with one of hers and the rest of the guys were mostly interested in other groups of girls by this point, but Cat and I carried on dancing, drinking and laughing together. She made a few references to my kinky escapades, asking if I still had my toys and if I’d found a new mistress. I answered yes and no, respectively.

As we became more intoxicated, we started dancing closer and closer. At first it seemed like a joke, until all of a sudden, with our bodies pressed against each other during a particularly sexy song, our eyes met and, with our faces mere inches apart we started to lean in for a kiss, when all of a sudden, we both got shoved unceremoniously aside as two men started fighting on the dance floor. I protectively put my arm across her, guiding her away from the sudden violence. We moved quickly and carefully away from the dance floor, while the security staff manhandled the offenders outside.

We chuckled together, ‘That was close,’ I said. But then she asked me where I was staying tonight, so I told her, ‘I moved back to town a few weeks ago. I’ve got a flat about 10 minutes from here.’
She smiled, ‘Let’s go then. I want to see your toy collection.’

We finished our drinks and left the club, just after midnight. We chatted quite generally during the walk to my place, she asked about my friend that had gone off with her friend. I told her that he was alright. She asked about my new job and I asked about hers. Neither of us mentioned Kylie and neither of us mentioned anything kinky. We just chatted and laughed and joked until we were on the landing outside my flat, where she grabbed me and kissed me forcefully. I offered no resistance, enjoying her tongue pressing against mine and her hand on my neck.

She broke away and nodded towards the door. I pulled out the key, opened the door and held it open for her. She crossed the room confidently and sat herself down on the sofa, kicking her heels off and leaning back playfully. I closed the door behind me, kicked off my own shoes and began crossing the room, when I was about to join her on the sofa, she held up her hand to stop me and said, ‘Get me a drink,’ her demanding tone reminiscent of Kylie’s and unlocking the submissive in me.

I crossed to the kitchen area and poured a gin and tonic for both of us and returned to the sofa. I put my drink down and made moves to kiss her again but she stopped me and pointed towards her feet.
‘You know what to do,’ she told me. 

I knelt on the floor as she put her feet up on the sofa and began kissing them while I caressed her calves, she watched me carefully as she sipped her drink, an evil grin on her face. I worked my way up her legs, convinced that I wouldn’t have much trouble slipping off her panties from under her dress and that I wouldn’t need to play the submissive for long. I was horny and the idea of getting to fuck my ex’s bitchy friend was fun, but just as my hands slipped under her dress, my fingers barely touching the straps of her underwear, she gently pushed me off her. ‘I think it’s time to show me your toys,’ she told me.

I hesitated, but it was clear there was still some fun to be had, so I took her by the hand, pulled her up from the sofa and led her into my bedroom.

My flat was on the top floor of an old building that had been converted, the bedroom had a sloped ceiling and a beautiful wooden beam. The décor was simple, just a student bookshelf, an armchair, a dresser and a built-in wardrobe. The room was surprisingly large and I’d moved the metal-framed, double bed against one wall, to create extra floor space.

I led Cat over to the wardrobe, opened it up and pulled out a large, black chest. I took the key out from the dresser drawer and opened my kinky repository. I stepped back as Cat crouched down and began looking through the box. I let my eyes wander down her back, across her ass and bare legs and down to her feet.

‘What am I doing?’ I asked myself, ‘I’m supposed to be getting together with Lisa and I’m fooling around with my ex’s bitchy friend.’ Logic and reason had been totally unwound by horniness and submission; a situation cemented by the look on her face when she turned around with a pair of handcuffs in her hand.

‘Let’s try these,’ she told me, with a wicked smile reminiscent of my ex-mistress.
‘Okay,’ I replied,
‘Where do you want me?’
‘Top off and under the beam.’
I complied, removing my t-shirt and allowing her to cuff me to the ceiling beam. I figured I would get some light teasing, maybe a blowjob, but that with so little experience of BDSM she would quickly release me and I would get to give her a good fucking.

Once I was secured, however, she quickly returned to the box and produced a simple device I had built myself – a short wooden plank with two metal eyes at either end.
‘What’s this for?’ she asked innocently.
‘It’s a spreader bar. You can attach ankle cuffs and force someone’s legs apart.’
‘That sounds fun,’ she replied, picking out the ankle cuffs and walking back towards me.

She undid my jeans and pulled them off of me roughly, followed by my boxers. My unleashed cock stood to attention but she barely seemed to pay any attention to it, even when she knelt in front of me, her face mere inches away. Instead, she focussed on placing the cuffs around my ankles and attaching the spreader bar, forcing me to stand with feet little over shoulder width apart.
‘Much better,’ she smiled as she stood up, ‘What else can we find?’

The next item she produced was a ball-gag, which she forced into my mouth with ease. I was beginning to have my doubts when she followed it up with some nipple clamps. The questions had stopped, she suddenly seemed to know exactly what everything was and what to do with it. My fears were confirmed when she pulled some rope at the box and began tying my cock and balls up in a tight and complex arrangement that left them painful, exposed and purple. She pulled over a chair and sat across from me, with a riding crop in her hand and a smile on her face.

‘Confession time,’ she began, ‘when Kylie showed us the kind of things you two were into at her house, I was intrigued. In fact, I became obsessed and started researching for myself.’
She paused to strike my hard, bound cock with the crop.
‘I asked Kylie every question I could think of and started watching all these porn videos of women torturing men.’
She struck again, my gasp of pain muffled by the gag.
‘And I loved it. It turned me on so much.’
She stood up and walked around the back of me.
‘Kylie got off on control and humiliation and I know you got off on that too.’
She struck my arse hard with the crop – harder than Kylie had ever whipped me. The initial sting was soon surpassed by a throbbing sensation that wouldn’t subside.
‘But that’s not what I wanted. It was pain I wanted to inflict.’
She struck again, harder than before.
‘I watched hours of videos, read every book and article I could find,’ she walked back around the front of me, her hips swaying seductively, ‘and I loved it.’
She pressed her body close to mine, I was trembling with fear, excitement and pain. She moved away from me, whipping my cock once more with a smile on her face.
‘I wanted to find a guy I could try all these things on, a guy I could hurt,’ she continued, ‘But there was no one. I would fantasise about it, I would masturbate thinking about having a slave of my own – just like Kylie had you, a slave I could torture. I tried websites, but every guy wanted something else or they would just talk and talk. I didn’t want to talk, I didn’t want a boyfriend, I didn’t want to fuck.’ She looked me dead in the eye, ‘I just wanted to hurt someone.’

She walked around behind me again, whipping my arse and thighs several times with harsh, stinging strikes. When she came back around the front, she walked past me and placed the whip on the chair before turning to face me. She unzipped her dress and let it sink slowly to the floor, her matching black underwear a sexy contrast to her pale skin.
‘And then tonight, I saw you.’ She smiled, ‘And I thought, ‘perfect – he’s submissive, he’s got the toys, all I’ve got to do is convince him to take me to his and I can do whatever I like.’
With that, she gave me a swift kick to the balls. I gasped in pain, my groans muffled by the gag.
‘So, here’s the deal,’ she explained, picking up a paddle from the chest, ‘If you let me do whatever I like to you, when I’m finished – you can fuck me.

I stared at her with disbelief, the precum dripping from my cock matched by the drool dripping from the gag. ‘You can fuck me however you want. I’ll suck your dick and call it ice-cream, if you like. And that’s it. You let me hurt you, I’ll let you do whatever you want with me.’
She walked behind me again and struck each of my ass cheeks three or four times with the paddle, making me whimper as each strike made the welts from the crop throb once more.
‘Of course, you could say no and there’s nothing really to stop me carrying on anyway,’ she said, as she moved back in front of me, her hand gently running over my bound cock. ‘But that’s a risk you’ll have to take.’ She squeezed my bound package hard and I tried to lurch forward but the restraints held me in place.
‘So, what do you say?’ I nodded my approval, tears in my eyes from the squeezing.

She let go, took a step back and kicked me again between the legs. I groaned and she smiled her evil smile. She kept me tied to the beam for around two hours of whipping, spanking and attacks on my genitals with various objects and body parts. She had mercy on me a few times, giving me a break from the gag and some water to drink every twenty minutes or so. When she let me down, I thought it was over, but she dragged me to the bed, tied me down and dripped hot candle wax over me, covering my chest, my cock and my balls. She then decided that a riding crop was the best implement to remove it.

After that, she found some clothes pegs, which she tied together with string and clipped onto my ballsack. She laughed when I winced as she pulled them off. It was around half four in the morning when she untied me for the last time, I was covered in scratches, bruises and welts. My genitals were sore and whatever position I lay in was uncomfortable.

We slept for a few hours and in the morning, I made good on her promise to let me do what I wanted with her. I was so sore that it made fucking her every way I could imagine difficult and she seemed to enjoy my pain more than I was enjoying the sex. She had several short, snakelike orgasms before, after fucking her tight body from behind, I was finally able to manhandle her to her knees and finish off in her mouth.

She showered and left me to clear up the mess. I slept for a while in the afternoon, and it was only in the evening that I remembered that the next day was my trip to visit Lisa. I was distraught when I realised the predicament I was now in. My body was covered in the physical evidence of my encounter with Cat – scratches and bruises were all over my back, arse, legs and chest. There was no chance of allowing anything to happen with Lisa without very awkward conversations, probably one that would prevent anything happening anyway.

That weekend, I hung out with Lisa and our mutual friends and I played it as safe as I could. I was friendly and fun, I flirted back when she flirted with me but on the two or three occasions she made a move, I played dumb and didn’t let anything happen. I figured I could go back in a couple of weeks, when the marks had faded and make my move then. Unfortunately, that wasn’t to be.

Around a week after my visit, I found out that Lisa had started seeing someone else. A mutual friend told me that she thought I wasn’t interested and met someone at a gig and that was that. My chances of landing an incredibly sexy girl that I really liked were ruined because I fell into the trap of my ex’s sadistic friend.

reddit.com
u/Afraid-Flan4278 — 18 days ago

A Trip to the Dungeon

Another story from my collection. This is the story of Kylie taking me to a dungeon for the first-time and her first time using a strap-on on me - something that became a regular feature in the final months of our relationship. I will be posting more soon.

After rewarding me for entertaining her friends at the sleepover, Kylie locked me back up in chastity. I went back to university a few days later for the start of my final year, with no idea when I would be unlocked again. She visited me two weeks later but I was only unlocked for a little while, whilst tied up and it ended in denial and being locked back up. Around mid-October I went to see her, we had a night out that ended in her letting me cum on her feet and lick them clean, before she locked me back up and kept me that way until my birthday at the end of November.

A week or so before my birthday, I went out with some friends of mine. The girls were all dressed to impress and the pain it caused me watching them dance was deeply frustrating. I opted to go home early that night, before I turned into a drooling mess.

Kylie told me that she had booked a bed and breakfast for a night over the weekend after my birthday. I was looking forward to it for multiple reasons, I had not seen her in a few weeks, I was excited about a night away and I was hoping that she would unlock me and let me cum. I worked really hard in the week leading up to the trip to make sure that I kept on her good side and had everything needed for a pleasant night away. I had simply no idea what Kylie had planned.

The bed and breakfast was an unassuming house down a country lane with a converted garage and no sign out front. We were shown into the annex on top of the garage, where there was a large bedroom, tastefully decorated with a four-poster bed and a bathroom with an extremely large shower. Everything seemed perfect and I placed my overnight bag on the armchair and sat on the edge of the bed as Kylie spoke quietly to the owner in the hallway. I looked around the room and smiled to myself, thinking this was surely going to be my lucky night.

Once we were alone, Kylie instructed me to take my clothes off and put my collar on, while she took her bag into the bathroom and closed the door behind her. I obeyed and sat myself on the edge of the bed, waiting for her, my cock straining against my cage in anticipation.

I gasped in astonishment as she walked out of the bathroom. She stood in the doorway wearing a tight black corset that bunched her ample breasts up high under her chin, a pair of black lace panties and some thigh high boots. In one hand she held her faithful riding crop and in the other hand she held a lead. The chain around her neck disappeared beneath her corset and I hoped it had my key on the end. She smiled her wicked smile and told me to follow her, stopping only to attach the lead to my collar.

I followed, gazing at her plump lace-covered buttocks shaking as she walked, with no idea where she was taking me. She led me along the corridor, down the stairs and through a door into a darkened room that had once been a garage. I could hear the hum of an electric heating system but it was only when Kylie flicked the light switch that I realised what the garage had been converted into.

It was a bondage dungeon, containing various pieces of furniture and equipment that I’d only seen in pornography. I gasped in astonishment again and she turned to me, kissed me passionately on the lips and said, ‘Happy birthday!’.

She was like a kid in the candy store at first, she seemed totally unsure of what to use first. She ordered me to kneel as she walked around inspecting every piece of kit. Eventually, she returned and led me over to some restraints attached to the cold brick wall. She pulled me up from the floor, lifted my arms and placed them in the cuffs above my head. She then spread my legs and locked them in place. She stood back, shook her head and muttered, ‘Something is missing’. She walked over to a box in the corner, pulled out a ball gag and forced it into my mouth, strapping it in place behind my head.
‘Much better,’ she smiled, ‘I don’t want to hear you complaining.’

She pulled her phone out of her corset, took a picture of me, caged, naked and chained to the wall. ‘Becky and Cat made me promise to send them a pic, I hope you don’t mind.’

I tried to protest but the gag muffled my reply, as she put her phone to one side and pulled the chain out from under her top, revealing the small key on the end. I instantly grew excited and strained even harder against the cage, groaning through the gag. She stepped towards me slowly, lent over and with a click, unlocked me and slowly removed the complex arrangement of plastic and metal.

My cock sprung to attention and Kylie moved her face close to mine, pressing her breasts against my chest. ‘Don’t get too excited now,’ she said as she slowly raised her knee between my legs and against my swollen balls.

I yelped slightly and she backed away, reaching for a paddle that was resting on top of a nearby cage. She stood to one side of me, lifted the paddle to head height and swung it down onto the top of my hard cock with force. She laughed at my muffled cry of pain and repeated the action again and again, spraying precum across the floor each time she hit me. She turned her attention to my balls and began striking them with the paddle from below, watching me react with her usual evil smile. A few times she pretended to hit, just to watch me wince.

After I was suitably tender, she produced a device I’d never seen before. A leather disc with a hole in the middle and chains attached. She wrapped it around my balls and closed some poppers to keep it in place, with the short chains dangling between my legs. She attached the chain to a piece of rope that ran through a pulley on the floor and tightened it so that it tugged slightly on my balls. She then clipped some clamps to my nipples and, with a short length of chain, attached them to a hook on the ceiling, so that they tugged gently on me too.

The wicked grin returned, as she began reeling in the rope attached to my balls. I instinctively tried to lower my hips, which was difficult when tied, to lessen the pain, but in doing so pulled on the clamps, which tightened around my sensitive nipples. I hissed in pain but Kylie just laughed.
‘Here’s a fun game,’ she said, ‘I’m going to ask you questions and if I like your answer, I’ll give you a little stroke,’ she demonstrated my running her hands gently along my twitching, dripping cock.
‘But if I don’t,’ she continued, ‘then I will do this.’ Kylie pulled the rope through the pulley, which simultaneously tugged on my balls and my nipples.
I nodded my understanding, as she stood up to gently take the gag out of my mouth.

‘Question 1. Have you been using the new butt-plugs I gave you?'
‘Yes mistress,’ I replied, as she gently stroked.
‘Every day?’
‘Yes mistress.’

‘Good,’ she pulled her hand away. ‘Question 2. Do you like your birthday treat?’
‘Yes mistress,’ I replied, enjoying the feel of her hand running over my free cock as she scooped up some precum and used it as lubricant for her gently strokes.

‘Question 3. How long should I keep you in chastity for this time?’
I hesitated, not sure what answer to give. ‘Umm. A month?’ I suggested.
She released my cock and instantly pulled on the rope, ‘That is too short. You’ve been in for six weeks this time, so it definitely has to be longer than that.’
‘Two months,’ I replied, only to feel the tug on my balls and nipples worse. My knees were bent as much as the restraints would allow and the pain shot through me.
‘The correct answer,’ she grinned, ‘is as long as I want.’
‘Yes mistress,’ I replied as she slackened the rope ever so slightly.

‘Question 4. Who would you rather fuck, Becky or Cat?’
I thought about Kylie’s two closest friends. Becky was the more attractive and a much nicer person too. Cat, whilst still pretty in her own way, could be a bit of a bitch and we’d never really get on.
‘Becky,’ I replied, honestly.
The pain returned, the pull on my balls was stronger this time and I strained against the clamps, my eyes watering from the sting. A swift whack to my cock from the paddle took my mind off my nipples and I groaned loudly.
‘No, no, no.’ Kylie replied, ‘The correct answer is whichever one I want you to fuck. You don’t get a choice.’
I nodded my understanding.
‘Don’t worry. I wouldn’t inflict your pathetic cock on either of them.’ She paused slightly, ‘I’m bored of this game now - let’s try something else.’

Kylie untied me and led me over to a cushioned bench in another part of the room and strapped me face down to it. It was clearly designed for someone to be fucked doggystyle in it and was surprisingly comfortable once in position. Once in place, she stood in front of me, turned away, lowered her black lace pants and pushed her plump butt towards my face. I lifted my head and instantly started kissing her jiggling cheeks. She then spread them and pushed herself back towards me. I took the hint and started licking her hole as best I could from my position. I heard her moan slightly as she pushed herself back into my face further. I did my best to please her but it was painful to lift my neck whilst tied to the bench and I found my tongue tiring very quickly.

She pulled away, leaving her knickers on the floor and moving around behind me. I heard a practice swing of a flogger as it struck the air and braced myself. During our nine-month relationship, Kylie had become extremely effective with floggers, crops and paddles and it was clearly one of her favourite things to do. I had become used to the sting of leather on flesh and the soreness I felt in the aftermath. The more I got used to it, the more skilled she seemed to become and she demonstrated this to excellent effect. The first blow from the flogger made me wince, the second made me gasp and the third made me scream softly. She switched then from flogger to paddle, the duller sensation making me groan each time she struck me, alternating from cheek to cheek and occasionally giving my balls a soft whack too. The crop was last and by far the most painful, the sting of it would leave marks on me for several days after each of her visits. The crop seemed to dance through the air, striking me again and again, I groaned and cried out. She was pushing my limit and I think she knew it, just as I was reaching the point where I didn’t think I could take any more, she stopped. She always knew exactly how much punishment I could take.

She knelt in front of me and wiped the tears from my cheeks and kissed me gently, before disappearing behind me again. I heard some objects being moved around but was unable to turn and find out what was in store for me, so I waited patiently. The next thing I felt was Kylie’s soft hand gently caressing my balls. She reached round and tenderly stroked my semi-hard cock back into life, her lubricated hand gliding gently across me. She ran her hand backs across my balls and between my cheeks, letting her lubed finger slide around my hole. She slipped it in and out gently. I had been playing with plugs and dildos for some time and the sensation of her finger inside me was pleasant. She paused, adding more lube and a second finger, letting them slip in and out gently. I rocked my hips back as much as I could, unable to help myself, wanting more sensation and more penetration.

She stopped and stood up, I heard her walking around me and as she came into view, I saw the large black strap on dildo attached to her by a tight harness. My eyes grew wide; it was bigger than anything I had taken before and I gasped slightly but Kylie ignored me. Instead, she approached me so that the tip of the dildo was touching my nose and whispered, ‘Kiss it.’
I complied, gently kissing the tip of the dildo.
‘Good boy,’ she said before disappearing behind me.

A moment or so later, I felt her between my legs, she ran a hand down my back and onto my hip. A squirt of cold lube ran between my cheeks and she rubbed it into my hole gently. I held my breath. The tip pressed against my hole gently and I relaxed as best I could, to open up for it and let it slide inside. There was little pain but I was well prepared and moaned softly as she slipped it out again.

She pressed it into me again, this time a little more and a little harder before pulling out. The third time she slid more in and instead of pulling out, started thrusting backwards and forwards gently. The sensation of being filled up by a moving object was incredibly pleasurable for me and I let out a soft groan of delight.

Kylie took the cue and began moving faster, thrusting harder. I rocked my hips backwards and forwards, as she picked up the tempo more and more. She slapped my stinging ass as she fucked me harder. ‘Do you like that?’ she said, slapping again.
‘Yes mistress,’ I replied eagerly and she thrust even faster.

With one hand she held my hip as she rocked backwards and forwards, the entire length of the dildo moving in and out of me now, her belly slapping rhythmically against my cheeks. I was groaning as she reached around and began to tug gently on my rock-hard cock. She picked up the pace and the sensation became too much for me, I let out a loud sound unlike any I’d ever made before, almost a roar, as I shot my load onto the bench beneath me.

She gently pulled the dildo out, let the harness drop to the floor and untied me. I sat up, my body sore and aching as she walked over and sat on a nearby thronelike chair. I looked over at her and we both smiled.

‘Come on then,’ she said, pointing between her legs, ‘It’s my turn.’
I dutifully walked over, dropped to my knees and complied.

reddit.com
u/Afraid-Flan4278 — 23 days ago

Kylie takes me to the dungeon [pegging] [bondage] [cbt]

Another story from my collection*. This is the story of Kylie taking me to a dungeon for the first-time and her first time using a strap-on on me - something that became a regular feature in the final months of our relationship. I will be posting more soon.*

After rewarding me for entertaining her friends at the sleepover, Kylie locked me back up in chastity. I went back to university a few days later for the start of my final year, with no idea when I would be unlocked again. She visited me two weeks later but I was only unlocked for a little while, whilst tied up and it ended in denial and being locked back up. Around mid-October I went to see her, we had a night out that ended in her letting me cum on her feet and lick them clean, before she locked me back up and kept me that way until my birthday at the end of November.

A week or so before my birthday, I went out with some friends of mine. The girls were all dressed to impress and the pain it caused me watching them dance was deeply frustrating. I opted to go home early that night, before I turned into a drooling mess.

Kylie told me that she had booked a bed and breakfast for a night over the weekend after my birthday. I was looking forward to it for multiple reasons, I had not seen her in a few weeks, I was excited about a night away and I was hoping that she would unlock me and let me cum. I worked really hard in the week leading up to the trip to make sure that I kept on her good side and had everything needed for a pleasant night away. I had simply no idea what Kylie had planned.

The bed and breakfast was an unassuming house down a country lane with a converted garage and no sign out front. We were shown into the annex on top of the garage, where there was a large bedroom, tastefully decorated with a four-poster bed and a bathroom with an extremely large shower. Everything seemed perfect and I placed my overnight bag on the armchair and sat on the edge of the bed as Kylie spoke quietly to the owner in the hallway. I looked around the room and smiled to myself, thinking this was surely going to be my lucky night.

Once we were alone, Kylie instructed me to take my clothes off and put my collar on, while she took her bag into the bathroom and closed the door behind her. I obeyed and sat myself on the edge of the bed, waiting for her, my cock straining against my cage in anticipation.

I gasped in astonishment as she walked out of the bathroom. She stood in the doorway wearing a tight black corset that bunched her ample breasts up high under her chin, a pair of black lace panties and some thigh high boots. In one hand she held her faithful riding crop and in the other hand she held a lead. The chain around her neck disappeared beneath her corset and I hoped it had my key on the end. She smiled her wicked smile and told me to follow her, stopping only to attach the lead to my collar.

I followed, gazing at her plump lace-covered buttocks shaking as she walked, with no idea where she was taking me. She led me along the corridor, down the stairs and through a door into a darkened room that had once been a garage. I could hear the hum of an electric heating system but it was only when Kylie flicked the light switch that I realised what the garage had been converted into.

It was a bondage dungeon, containing various pieces of furniture and equipment that I’d only seen in pornography. I gasped in astonishment again and she turned to me, kissed me passionately on the lips and said, ‘Happy birthday!’.

She was like a kid in the candy store at first, she seemed totally unsure of what to use first. She ordered me to kneel as she walked around inspecting every piece of kit. Eventually, she returned and led me over to some restraints attached to the cold brick wall. She pulled me up from the floor, lifted my arms and placed them in the cuffs above my head. She then spread my legs and locked them in place. She stood back, shook her head and muttered, ‘Something is missing’. She walked over to a box in the corner, pulled out a ball gag and forced it into my mouth, strapping it in place behind my head.
‘Much better,’ she smiled, ‘I don’t want to hear you complaining.’

She pulled her phone out of her corset, took a picture of me, caged, naked and chained to the wall. ‘Becky and Cat made me promise to send them a pic, I hope you don’t mind.’

I tried to protest but the gag muffled my reply, as she put her phone to one side and pulled the chain out from under her top, revealing the small key on the end. I instantly grew excited and strained even harder against the cage, groaning through the gag. She stepped towards me slowly, lent over and with a click, unlocked me and slowly removed the complex arrangement of plastic and metal.

My cock sprung to attention and Kylie moved her face close to mine, pressing her breasts against my chest. ‘Don’t get too excited now,’ she said as she slowly raised her knee between my legs and against my swollen balls.

I yelped slightly and she backed away, reaching for a paddle that was resting on top of a nearby cage. She stood to one side of me, lifted the paddle to head height and swung it down onto the top of my hard cock with force. She laughed at my muffled cry of pain and repeated the action again and again, spraying precum across the floor each time she hit me. She turned her attention to my balls and began striking them with the paddle from below, watching me react with her usual evil smile. A few times she pretended to hit, just to watch me wince.

After I was suitably tender, she produced a device I’d never seen before. A leather disc with a hole in the middle and chains attached. She wrapped it around my balls and closed some poppers to keep it in place, with the short chains dangling between my legs. She attached the chain to a piece of rope that ran through a pulley on the floor and tightened it so that it tugged slightly on my balls. She then clipped some clamps to my nipples and, with a short length of chain, attached them to a hook on the ceiling, so that they tugged gently on me too.

The wicked grin returned, as she began reeling in the rope attached to my balls. I instinctively tried to lower my hips, which was difficult when tied, to lessen the pain, but in doing so pulled on the clamps, which tightened around my sensitive nipples. I hissed in pain but Kylie just laughed.
‘Here’s a fun game,’ she said, ‘I’m going to ask you questions and if I like your answer, I’ll give you a little stroke,’ she demonstrated my running her hands gently along my twitching, dripping cock.
‘But if I don’t,’ she continued, ‘then I will do this.’ Kylie pulled the rope through the pulley, which simultaneously tugged on my balls and my nipples.
I nodded my understanding, as she stood up to gently take the gag out of my mouth.

‘Question 1. Have you been using the new butt-plugs I gave you?'
‘Yes mistress,’ I replied, as she gently stroked.
‘Every day?’
‘Yes mistress.’

‘Good,’ she pulled her hand away. ‘Question 2. Do you like your birthday treat?’
‘Yes mistress,’ I replied, enjoying the feel of her hand running over my free cock as she scooped up some precum and used it as lubricant for her gently strokes.

‘Question 3. How long should I keep you in chastity for this time?’
I hesitated, not sure what answer to give. ‘Umm. A month?’ I suggested.
She released my cock and instantly pulled on the rope, ‘That is too short. You’ve been in for six weeks this time, so it definitely has to be longer than that.’
‘Two months,’ I replied, only to feel the tug on my balls and nipples worse. My knees were bent as much as the restraints would allow and the pain shot through me.
‘The correct answer,’ she grinned, ‘is as long as I want.’
‘Yes mistress,’ I replied as she slackened the rope ever so slightly.

‘Question 4. Who would you rather fuck, Becky or Cat?’
I thought about Kylie’s two closest friends. Becky was the more attractive and a much nicer person too. Cat, whilst still pretty in her own way, could be a bit of a bitch and we’d never really get on.
‘Becky,’ I replied, honestly.
The pain returned, the pull on my balls was stronger this time and I strained against the clamps, my eyes watering from the sting. A swift whack to my cock from the paddle took my mind off my nipples and I groaned loudly.
‘No, no, no.’ Kylie replied, ‘The correct answer is whichever one I want you to fuck. You don’t get a choice.’
I nodded my understanding.
‘Don’t worry. I wouldn’t inflict your pathetic cock on either of them.’ She paused slightly, ‘I’m bored of this game now - let’s try something else.’

Kylie untied me and led me over to a cushioned bench in another part of the room and strapped me face down to it. It was clearly designed for someone to be fucked doggystyle in it and was surprisingly comfortable once in position. Once in place, she stood in front of me, turned away, lowered her black lace pants and pushed her plump butt towards my face. I lifted my head and instantly started kissing her jiggling cheeks. She then spread them and pushed herself back towards me. I took the hint and started licking her hole as best I could from my position. I heard her moan slightly as she pushed herself back into my face further. I did my best to please her but it was painful to lift my neck whilst tied to the bench and I found my tongue tiring very quickly.

She pulled away, leaving her knickers on the floor and moving around behind me. I heard a practice swing of a flogger as it struck the air and braced myself. During our nine-month relationship, Kylie had become extremely effective with floggers, crops and paddles and it was clearly one of her favourite things to do. I had become used to the sting of leather on flesh and the soreness I felt in the aftermath. The more I got used to it, the more skilled she seemed to become and she demonstrated this to excellent effect. The first blow from the flogger made me wince, the second made me gasp and the third made me scream softly. She switched then from flogger to paddle, the duller sensation making me groan each time she struck me, alternating from cheek to cheek and occasionally giving my balls a soft whack too. The crop was last and by far the most painful, the sting of it would leave marks on me for several days after each of her visits. The crop seemed to dance through the air, striking me again and again, I groaned and cried out. She was pushing my limit and I think she knew it, just as I was reaching the point where I didn’t think I could take any more, she stopped. She always knew exactly how much punishment I could take.

She knelt in front of me and wiped the tears from my cheeks and kissed me gently, before disappearing behind me again. I heard some objects being moved around but was unable to turn and find out what was in store for me, so I waited patiently. The next thing I felt was Kylie’s soft hand gently caressing my balls. She reached round and tenderly stroked my semi-hard cock back into life, her lubricated hand gliding gently across me. She ran her hand backs across my balls and between my cheeks, letting her lubed finger slide around my hole. She slipped it in and out gently. I had been playing with plugs and dildos for some time and the sensation of her finger inside me was pleasant. She paused, adding more lube and a second finger, letting them slip in and out gently. I rocked my hips back as much as I could, unable to help myself, wanting more sensation and more penetration.

She stopped and stood up, I heard her walking around me and as she came into view, I saw the large black strap on dildo attached to her by a tight harness. My eyes grew wide; it was bigger than anything I had taken before and I gasped slightly but Kylie ignored me. Instead, she approached me so that the tip of the dildo was touching my nose and whispered, ‘Kiss it.’
I complied, gently kissing the tip of the dildo.
‘Good boy,’ she said before disappearing behind me.

A moment or so later, I felt her between my legs, she ran a hand down my back and onto my hip. A squirt of cold lube ran between my cheeks and she rubbed it into my hole gently. I held my breath. The tip pressed against my hole gently and I relaxed as best I could, to open up for it and let it slide inside. There was little pain but I was well prepared and moaned softly as she slipped it out again.

She pressed it into me again, this time a little more and a little harder before pulling out. The third time she slid more in and instead of pulling out, started thrusting backwards and forwards gently. The sensation of being filled up by a moving object was incredibly pleasurable for me and I let out a soft groan of delight.

Kylie took the cue and began moving faster, thrusting harder. I rocked my hips backwards and forwards, as she picked up the tempo more and more. She slapped my stinging ass as she fucked me harder. ‘Do you like that?’ she said, slapping again.
‘Yes mistress,’ I replied eagerly and she thrust even faster.

With one hand she held my hip as she rocked backwards and forwards, the entire length of the dildo moving in and out of me now, her belly slapping rhythmically against my cheeks. I was groaning as she reached around and began to tug gently on my rock-hard cock. She picked up the pace and the sensation became too much for me, I let out a loud sound unlike any I’d ever made before, almost a roar, as I shot my load onto the bench beneath me.

She gently pulled the dildo out, let the harness drop to the floor and untied me. I sat up, my body sore and aching as she walked over and sat on a nearby thronelike chair. I looked over at her and we both smiled.

‘Come on then,’ she said, pointing between her legs, ‘It’s my turn.’
I dutifully walked over, dropped to my knees and complied.

reddit.com
u/Afraid-Flan4278 — 23 days ago

Serving at Kylie's Sleepover [chastity] [humiliation] [group service]

Another true story from my collection, available on Kindle. Kylie forces me to serve her and her friends at a sleepover and reveals my situation to them as we approach one year together. You can find my previous instalment here and all the others on my profile.

The patterns of tease, denial and humiliation continued for the next few months, gradually building towards longer periods locked up and more humiliation and servitude. During the summer break before my last year at uni, Kylie decided to throw a small party while her Dad was away, with her closest friends and their boyfriends.

Gradually the plan changed though, there was a break up in the run up to Christmas, a bit of a falling out and in the end, she decided that it would just be her, her two best friends and me. I offered to leave them to it and let them have a girls’ night in but she decided that I could spend the night fetching drinks and serving them instead.

I went round a couple of hours early to help prepare and was lucky enough to be allowed to spend a little bit of time worshipping her body before I was put to work cooking and cleaning. She made it very clear that if I was well behaved tonight then I would be allowed to fuck her later on. I was eager to comply, it is amazing how quickly chastity breaks any last vestiges of resistance against female domination and I had become the epitome of the submissive boyfriend.

I made Kylie and her friends cocktails when they arrived. She invited two of her oldest school friends, Becky and Cat, who she was still extremely close to. Becky was the traditional beauty, slim with blonde hair and a tight body. She had done a little modelling but wasn’t looking to pursue it as a career. To look at her, you would expect her to be a bit of a bitch but she was a genuinely nice person and we had always got along. She had a boyfriend who was in the army and wasn’t around often but he was a lot of fun and I’d always enjoyed hanging out with him and Becky.

Cat, on the other hand, was not someone I enjoyed spending time with, though I will admit that she was hot but in a very different way to Becky. She was shorter, with dark hair and piercing eyes. She was curvy and on the rare occasion that she smiled looked genuinely pretty. It was her personality I found unattractive, she could be mean spirited and always seemed to be bitter about something. Her and her boyfriend had broken up recently and I knew that she would be on fine form tonight. However, much as I didn’t like her, I decided to make as much effort as I could to be nice to her in the hope of winning Kylie’s favour.

After I made them drinks, I brought out some party food and set to work clearing up the kitchen, leaving the girls to catch up in the living room. I checked in regularly to be sure their glasses were always full and, after a little while, overheard Cat ask Kylie, ‘What’s going on with him?’.
‘Oh,’ Kylie replied, ‘He’s just being a good little bitch.’

The three girls laughed and carried on chatting. After the kitchen was thoroughly cleared and everyone had their drinks topped up, I went and sat on the floor at Kylie’s feet. The girls were a little tipsy by now and I was on the way too, having had a few beers whilst cleaning. I kept quiet and let them chat, laugh and drink away, occasionally getting up to refill glasses. Becky and Cat had both got very used to me serving them by now and would wave their glasses at me whenever they wanted more. Kylie gave me a nudge with her foot and I looked up at her, ‘I think we need more snacks,’ she said.
‘Yes mistress,’ I replied instinctively.
Becky and Cat burst out laughing, ‘Mistress?’ they asked.
‘I told you he was my little bitch,’ Kylie replied as I left the room to fetch some food.

The three girls, one by one, all disappeared to change into their pyjamas. Kylie deliberately chose a set that showed plenty of skin to torment me. Becky had short shorts on and Cat wore a low top to hers, all of which served to remind me of my unsatisfied horniness and caged cock. ‘Why isn’t he wearing pyjamas?’ Becky asked, not long after they had all changed.
‘I don’t really have any,’ I replied, hesitantly, ‘I normally just sleep in my underwear.’
‘That will do,’ Cat laughed. I looked up at Kylie, a nervous look on my face.
‘You heard them’ she said firmly,
‘We’re all in our pyjamas, so you’d better be in yours too.’

I stood up hesitantly, took off my t-shirt and socks and slowly unbutton my jeans.
‘Off, off, off,’ Cat began chanting jokingly.
‘Off, off, off,’ Becky joined in while Kylie just watched me, that familiar wicked smile on her lips. I pulled my jeans to the floor to reveal my tight purple thong stretched over the clearly visible outline of the bulging cock cage.
The girls laughed again. ‘What is it?’ Cat asked.
‘It’s why he’s been doing what he’s told all night,’ Kylie explained.
‘Wow!’ Becky added, ‘I knew you guys were kinky but that is something else!’
‘I think you’d better show them,’ Kylie said, leaning forward on the edge of the sofa and looking up at me.

I hesitated but complied with her orders and pulled my panties to the floor, revealing my confined cock, trapped inside its plastic and metal hell. Becky and Cat both moved forward on their seats for a closer look.
‘I’ve heard of them,’ Becky said, ‘But I didn’t think they were really a thing.’

As the girls talked, a small drop of precum began leaking out of the cage. Becky spotted it first, ‘Look at that,’ she said, ‘he likes it’.
And the girls burst into a fit of hysterics. ‘How long has he been wearing it?’ Cat asked, once she had recovered.
‘He’s had it on for about six months, though I let him out for a ruined orgasm from time to time.’
‘What’s a ruined orgasm?’ Cat asked.
Becky explained before Kylie had a chance.
Cat chuckled wickedly when she heard what it was and poured the remainder of her drink into her mouth and waved her glass at me, ‘Go on then, little bitch boy,’ she said, ‘Get me another drink.’
‘Me too,’ Becky added with Kylie also handing me an empty glass.

I took the glasses and walked out of the room, completely naked but for the cage, to the laughter of the three girls behind me. ‘What else can we make him do?’ I heard Becky ask as I returned with the fresh drinks.

After taking her glass, Kylie looked up at me, smiled and said, ‘Go get my riding crop and a paddle. Oh, and while you’re there, put your new toy in – the one I got you for Christmas. Get your collar and lead too.’
‘Yes mistress,’ I replied.

Again, Cat and Becky laughed at this, which made Kylie laugh too. The site of three attractive girls, in their pyjamas, laughing at me only served to add to my already considerable horniness and the stream of precum dripping from me. I left the room quickly and as I did so I heard Cat say, ‘You were right though, he does have a nice butt.’

I returned with the spanking implements and my new toy in place. For Christmas, Kylie had bought me a vibrating, inflatable butt plug. It started off small and I was able to fit it in easily, though walking with the wire to the remote and the tube to the pump swinging between my legs was a little clumsy. Kylie had that grin on her face again when I came back and gave her the spanking implements, whilst Becky, once again, explained to Cat what the new toy was. ‘You know a lot about this,’ Kylie asked Becky, ‘Anything you want to share?’
‘I watch a lot of porn,’ she admitted,
‘Shaun likes to tie me up and fuck me rough. It’s fun.’

The thought of the beautiful Becky being bound and fucked hard caught my attention and if I’d not been restrained, would have caused my cock to twitch. Instead, it just made the cage feel tighter around my desperation.
‘I tried that with him for his birthday,’ Kylie replied, ‘But it was pathetic. I could do with a good hard fuck every now and then but since we started doing this, he can’t last long enough.’
The girls laughed.
‘Well, maybe when Shaun is back, he can fuck us both and this little bitch can watch,’ Becky replied.
‘What about me?’ Cat interjected.
Becky smiled, ‘Sure, you can join in too.’

This conversation had me positively oozing precum but I kept quiet and waited for whatever Kylie had in mind to transpire. ‘Hands and knees,’ she ordered and I instantly obeyed. She stood over me and gave me a moderate whack with the crop. I grunted in pain and Becky and Cat laughed.

‘We’re going to play a game,’ Kylie explained, handing Becky the crop, ‘Becky is going to spank you and every time you make a noise, I’m going to pump this.’ She squeezed the pump and I felt the plug grow inside me, it was a strange sensation, the extra tightness made my cock strain in its cage and it took my breath away for a moment. Kylie hit the valve and released the extra pressure. ‘Got it?’
‘Yes mistress.’
‘What about me?’ Cat asked again. ‘While we’re doing this, he’s going to worship you,’ Kylie added, ‘Starting with your feet.’

She dragged me towards where Cat was seated, until I was kneeling in front of her and handed her the lead attached to my collar. Without saying anything, I bent down and started kissing her bare feet. She giggled and I looked up at her just as Becky whacked me on the arse hard with the paddle. I cried out in pain and instantly felt the plug grow again inside me, but this time there was no release of the valve.

‘Keep worshipping,’ Kylie reminded me and I instantly returned my attention to Cat’s feet. Another whack but this time I suppressed my cry and kept kissing.
‘What now?’ Cat asked Kylie.
‘Whatever you want,’ she replied, as another smack from Becky took me surprised and made me yelp.

The plug grew once more inside me and the internal pressure was a delightful torment. I looked up at Cat again, she laughed at me. I knew she didn’t like me and there must be something incredibly empowering about having someone you hate totally humiliated before you and kissing your feet.

‘Can I have the crop?’ she asked, standing up. I gulped, knowing this was going to be bad, as she moved behind me and Becky took her place and sat on the armchair in front of me with her bare legs. I lowered my head and began kissing her feet, waiting for the first blow from Cat.

When it came, it came with force and stung like hell. She did not hold back and I screamed and lurched forward until my head was hovering in Becky’s lap. I could hear Cat laughing with glee as my arse throbbed from the sting. The pump grew once again and I moaned slightly as it pressed against my prostate.
‘Was that more noise?’ Kylie asked, pumping again, this time I suppressed any noise. I knew I would only be able to take one or two more pumps.

Becky put her hand on the back of my head and spread her legs slightly, pulling me between her thighs. She wrapped her legs around me and held me in place, my face inches away from her pussy. I almost thought that I could smell it and I couldn’t help but wonder what she tasted like.

My thoughts were interrupted by another whack, I cried out once again and Kylie pumped once more. Becky held me in place as Cat whacked me again, I barely managed to stop myself but the next blow with the crop came so quickly afterwards that I had no chance and felt the buttplug grow inside me. I felt incredibly full, like my insides were being pushed from every direction. I heard Kylie and Cat speaking, but couldn’t work out what they were saying, my head throbbing in time with my racing heartbeat as Becky lowered me back to all fours on the floor.

Kylie flicked on the vibrating switch for the plug and I instantly began to shake and moan, she dialled it up and the huge plug inside me danced and made me feel like my whole body was vibrating. I looked down between my legs at the huge trail of precum leaking out of me as I shook with delight and torment. My whole world became vibrations and laughter for several long minutes before, with no warning, the vibrations stop and the valve was released. I gasped loudly and practically collapsed in a puddle.

‘It’s late,’ Kylie said, ‘go make us one last drink and clean up.’ It took me a moment to make sense of her words. As I rose to my feet, she stepped over to me, gave me a gentle kiss on the lips and whispered, ‘Well done, you will be rewarded.’

reddit.com
u/Afraid-Flan4278 — 29 days ago

Serving at Kylie's Sleepover

Another true story from my collection, available on Kindle. Kylie forces me to serve her and her friends at a sleepover and reveals my situation to them as we approach one year together. You can find my previous instalment here and all the others on my profile.

The patterns of tease, denial and humiliation continued for the next few months, gradually building towards longer periods locked up and more humiliation and servitude. During the summer break before my last year at uni, Kylie decided to throw a small party while her Dad was away, with her closest friends and their boyfriends.

Gradually the plan changed though, there was a break up in the run up to Christmas, a bit of a falling out and in the end, she decided that it would just be her, her two best friends and me. I offered to leave them to it and let them have a girls’ night in but she decided that I could spend the night fetching drinks and serving them instead.

I went round a couple of hours early to help prepare and was lucky enough to be allowed to spend a little bit of time worshipping her body before I was put to work cooking and cleaning. She made it very clear that if I was well behaved tonight then I would be allowed to fuck her later on. I was eager to comply, it is amazing how quickly chastity breaks any last vestiges of resistance against female domination and I had become the epitome of the submissive boyfriend.

I made Kylie and her friends cocktails when they arrived. She invited two of her oldest school friends, Becky and Cat, who she was still extremely close to. Becky was the traditional beauty, slim with blonde hair and a tight body. She had done a little modelling but wasn’t looking to pursue it as a career. To look at her, you would expect her to be a bit of a bitch but she was a genuinely nice person and we had always got along. She had a boyfriend who was in the army and wasn’t around often but he was a lot of fun and I’d always enjoyed hanging out with him and Becky.

Cat, on the other hand, was not someone I enjoyed spending time with, though I will admit that she was hot but in a very different way to Becky. She was shorter, with dark hair and piercing eyes. She was curvy and on the rare occasion that she smiled looked genuinely pretty. It was her personality I found unattractive, she could be mean spirited and always seemed to be bitter about something. Her and her boyfriend had broken up recently and I knew that she would be on fine form tonight. However, much as I didn’t like her, I decided to make as much effort as I could to be nice to her in the hope of winning Kylie’s favour.

After I made them drinks, I brought out some party food and set to work clearing up the kitchen, leaving the girls to catch up in the living room. I checked in regularly to be sure their glasses were always full and, after a little while, overheard Cat ask Kylie, ‘What’s going on with him?’.
‘Oh,’ Kylie replied, ‘He’s just being a good little bitch.’

The three girls laughed and carried on chatting. After the kitchen was thoroughly cleared and everyone had their drinks topped up, I went and sat on the floor at Kylie’s feet. The girls were a little tipsy by now and I was on the way too, having had a few beers whilst cleaning. I kept quiet and let them chat, laugh and drink away, occasionally getting up to refill glasses. Becky and Cat had both got very used to me serving them by now and would wave their glasses at me whenever they wanted more. Kylie gave me a nudge with her foot and I looked up at her, ‘I think we need more snacks,’ she said.
‘Yes mistress,’ I replied instinctively.
Becky and Cat burst out laughing, ‘Mistress?’ they asked.
‘I told you he was my little bitch,’ Kylie replied as I left the room to fetch some food.

The three girls, one by one, all disappeared to change into their pyjamas. Kylie deliberately chose a set that showed plenty of skin to torment me. Becky had short shorts on and Cat wore a low top to hers, all of which served to remind me of my unsatisfied horniness and caged cock. ‘Why isn’t he wearing pyjamas?’ Becky asked, not long after they had all changed.
‘I don’t really have any,’ I replied, hesitantly, ‘I normally just sleep in my underwear.’
‘That will do,’ Cat laughed. I looked up at Kylie, a nervous look on my face.
‘You heard them’ she said firmly,
‘We’re all in our pyjamas, so you’d better be in yours too.’

I stood up hesitantly, took off my t-shirt and socks and slowly unbutton my jeans.
‘Off, off, off,’ Cat began chanting jokingly.
‘Off, off, off,’ Becky joined in while Kylie just watched me, that familiar wicked smile on her lips. I pulled my jeans to the floor to reveal my tight purple thong stretched over the clearly visible outline of the bulging cock cage.
The girls laughed again. ‘What is it?’ Cat asked.
‘It’s why he’s been doing what he’s told all night,’ Kylie explained.
‘Wow!’ Becky added, ‘I knew you guys were kinky but that is something else!’
‘I think you’d better show them,’ Kylie said, leaning forward on the edge of the sofa and looking up at me.

I hesitated but complied with her orders and pulled my panties to the floor, revealing my confined cock, trapped inside its plastic and metal hell. Becky and Cat both moved forward on their seats for a closer look.
‘I’ve heard of them,’ Becky said, ‘But I didn’t think they were really a thing.’

As the girls talked, a small drop of precum began leaking out of the cage. Becky spotted it first, ‘Look at that,’ she said, ‘he likes it’.
And the girls burst into a fit of hysterics. ‘How long has he been wearing it?’ Cat asked, once she had recovered.
‘He’s had it on for about six months, though I let him out for a ruined orgasm from time to time.’
‘What’s a ruined orgasm?’ Cat asked.
Becky explained before Kylie had a chance.
Cat chuckled wickedly when she heard what it was and poured the remainder of her drink into her mouth and waved her glass at me, ‘Go on then, little bitch boy,’ she said, ‘Get me another drink.’
‘Me too,’ Becky added with Kylie also handing me an empty glass.

I took the glasses and walked out of the room, completely naked but for the cage, to the laughter of the three girls behind me. ‘What else can we make him do?’ I heard Becky ask as I returned with the fresh drinks.

After taking her glass, Kylie looked up at me, smiled and said, ‘Go get my riding crop and a paddle. Oh, and while you’re there, put your new toy in – the one I got you for Christmas. Get your collar and lead too.’
‘Yes mistress,’ I replied.

Again, Cat and Becky laughed at this, which made Kylie laugh too. The site of three attractive girls, in their pyjamas, laughing at me only served to add to my already considerable horniness and the stream of precum dripping from me. I left the room quickly and as I did so I heard Cat say, ‘You were right though, he does have a nice butt.’

I returned with the spanking implements and my new toy in place. For Christmas, Kylie had bought me a vibrating, inflatable butt plug. It started off small and I was able to fit it in easily, though walking with the wire to the remote and the tube to the pump swinging between my legs was a little clumsy. Kylie had that grin on her face again when I came back and gave her the spanking implements, whilst Becky, once again, explained to Cat what the new toy was. ‘You know a lot about this,’ Kylie asked Becky, ‘Anything you want to share?’
‘I watch a lot of porn,’ she admitted,
‘Shaun likes to tie me up and fuck me rough. It’s fun.’

The thought of the beautiful Becky being bound and fucked hard caught my attention and if I’d not been restrained, would have caused my cock to twitch. Instead, it just made the cage feel tighter around my desperation.
‘I tried that with him for his birthday,’ Kylie replied, ‘But it was pathetic. I could do with a good hard fuck every now and then but since we started doing this, he can’t last long enough.’
The girls laughed.
‘Well, maybe when Shaun is back, he can fuck us both and this little bitch can watch,’ Becky replied.
‘What about me?’ Cat interjected.
Becky smiled, ‘Sure, you can join in too.’

This conversation had me positively oozing precum but I kept quiet and waited for whatever Kylie had in mind to transpire. ‘Hands and knees,’ she ordered and I instantly obeyed. She stood over me and gave me a moderate whack with the crop. I grunted in pain and Becky and Cat laughed.

‘We’re going to play a game,’ Kylie explained, handing Becky the crop, ‘Becky is going to spank you and every time you make a noise, I’m going to pump this.’ She squeezed the pump and I felt the plug grow inside me, it was a strange sensation, the extra tightness made my cock strain in its cage and it took my breath away for a moment. Kylie hit the valve and released the extra pressure. ‘Got it?’
‘Yes mistress.’
‘What about me?’ Cat asked again. ‘While we’re doing this, he’s going to worship you,’ Kylie added, ‘Starting with your feet.’

She dragged me towards where Cat was seated, until I was kneeling in front of her and handed her the lead attached to my collar. Without saying anything, I bent down and started kissing her bare feet. She giggled and I looked up at her just as Becky whacked me on the arse hard with the paddle. I cried out in pain and instantly felt the plug grow again inside me, but this time there was no release of the valve.

‘Keep worshipping,’ Kylie reminded me and I instantly returned my attention to Cat’s feet. Another whack but this time I suppressed my cry and kept kissing.
‘What now?’ Cat asked Kylie.
‘Whatever you want,’ she replied, as another smack from Becky took me surprised and made me yelp.

The plug grew once more inside me and the internal pressure was a delightful torment. I looked up at Cat again, she laughed at me. I knew she didn’t like me and there must be something incredibly empowering about having someone you hate totally humiliated before you and kissing your feet.

‘Can I have the crop?’ she asked, standing up. I gulped, knowing this was going to be bad, as she moved behind me and Becky took her place and sat on the armchair in front of me with her bare legs. I lowered my head and began kissing her feet, waiting for the first blow from Cat.

When it came, it came with force and stung like hell. She did not hold back and I screamed and lurched forward until my head was hovering in Becky’s lap. I could hear Cat laughing with glee as my arse throbbed from the sting. The pump grew once again and I moaned slightly as it pressed against my prostate.
‘Was that more noise?’ Kylie asked, pumping again, this time I suppressed any noise. I knew I would only be able to take one or two more pumps.

Becky put her hand on the back of my head and spread her legs slightly, pulling me between her thighs. She wrapped her legs around me and held me in place, my face inches away from her pussy. I almost thought that I could smell it and I couldn’t help but wonder what she tasted like.

My thoughts were interrupted by another whack, I cried out once again and Kylie pumped once more. Becky held me in place as Cat whacked me again, I barely managed to stop myself but the next blow with the crop came so quickly afterwards that I had no chance and felt the buttplug grow inside me. I felt incredibly full, like my insides were being pushed from every direction. I heard Kylie and Cat speaking, but couldn’t work out what they were saying, my head throbbing in time with my racing heartbeat as Becky lowered me back to all fours on the floor.

Kylie flicked on the vibrating switch for the plug and I instantly began to shake and moan, she dialled it up and the huge plug inside me danced and made me feel like my whole body was vibrating. I looked down between my legs at the huge trail of precum leaking out of me as I shook with delight and torment. My whole world became vibrations and laughter for several long minutes before, with no warning, the vibrations stop and the valve was released. I gasped loudly and practically collapsed in a puddle.

‘It’s late,’ Kylie said, ‘go make us one last drink and clean up.’ It took me a moment to make sense of her words. As I rose to my feet, she stepped over to me, gave me a gentle kiss on the lips and whispered, ‘Well done, you will be rewarded.’

reddit.com
u/Afraid-Flan4278 — 29 days ago

Kylie's Tasks [chastity] [prejac training] [panties]

The next instalment from my collection (available in full on Kindle), about my long-distance uni girlfriend who become my mistress and the fun we had. My chastity sentences have begun to get longer with greater challenges on the rare occasions we see each other. The previous instalment is here.

After being locked back in my chastity cage on New Year’s Day, I went back to uni a couple of days later with no fixed plans to see Kylie again soon, or any knowledge of when I would next be unlocked. We had discussed Valentine's Day in passing, but had not confirmed anything.

We had the usual chats online a few times a week, sometimes casual and sometimes spicy. I had become quite accustomed to the cage already and although it was tight and uncomfortable when I was turned on, it was mostly a pleasant feeling. Sometimes, when my mind wandered, I found myself leaking large amounts of precum, which felt very strange at first but was something I began to really enjoy. Kylie got off on it too, when I would tell her about it or send her pictures.

I’d become increasingly submissive, not just to Kylie, but in general. Yet it felt empowering, and I found that I had more motivation towards uni work, my fitness, keeping my flat clean and towards my hobbies. Something about the limitations it imposed on me, about the constant little reminders, sharpened me and gave me a new drive.

One wet Saturday morning, right at the end of January, I was at home having just got back from a trip to the grocery store, when the doorbell rang. I headed down the stairs and opened the door, which was on the side of the corner shop below me, to reveal Kylie standing there in a raincoat. I let her in and we headed upstairs where I made her a cup of tea to warm her up.

‘My plans got cancelled, so I thought I would surprise you,’ she explained.
‘It’s a good surprise.’

We drank the tea and chatted for a little while, gossiping and joking about various topics. We made out for a little while on my sofa and I could feel precum leaking from me continuously. She reached down and undid my jeans, pulling down the zip and grabbing the waistband and revealing my boxers.

‘What’s this?’ she demanded.
I gave her a curious look.
‘I told you that you were only allowed to wear panties when we’re together.’
‘I know,’ I said, defending myself. ‘But I didn’t know you were coming.’
‘That is not an excuse - let’s get you changed now,’ her tone was serious and she marched me into the bedroom and made me take off the boxers and replace them with a pink and gold g-string with the word ‘angel’ emblazoned across the crotch.

‘Much better,’ she said as she made me give her a twirl before putting my jeans back on. ‘We need to make sure this doesn’t happen again.’
She opened up my underwear drawer and took out all the boxershorts, leaving behind only my collection of women’s underwear - about a dozen pairs. She placed the boxers in a grocery bag that was on the kitchen side and told me to get ready to go out.
‘Let’s get rid of these for good.’

We headed out for lunch at a cafe in town and Kylie made me deposit the bag of underwear in a public bin on the way.
‘No more boy pants for you,’ she declared with a vicious smile.

After lunch we went to the cinema; I struggled to concentrate on the movie because Kylie’s hand was caressing my leg or feeling my cage through my jeans the whole time. I was unfathomably horny.

We walked back to my flat and I cooked us dinner, which we ate with a bottle of wine whilst watching some half-baked comedy programme.

When the show finished, she led me to the bedroom, undressed and lay on the bed. She beckoned me over and I climbed on top of her, missionary style. She grabbed me and kissed me and held me against her, my cage pressed against her naked thigh. I kissed her neck and her breasts, groaning softly all the time. She pushed me further down and I kissed her stomach, her thighs and eventually plunged my face between her legs and began licking, kissing and sucking her clit.

I looked up at her and saw her fondling the key and the chain between her fingers. I redoubled my efforts and worked as hard as I could to make her cum as hard as possible, which she did, over and over again. Each time I would look up, to see if she was satisfied enough to unlock me, but each time she would just push my head back down for more.

After what felt like hours and both of us soaked in sweat and cum, Kylie stopped me and told me she was going for a shower. I lay there in the bed, jaw and tongue aching, dripping gallons of precum through the holes in the cock-cage. When Kylie returned, wrapped in a towel, she sent me to take a shower too, ‘better make it a cold one,’ she added with a grin. When I returned, Kylie was in bed, naked but with the covers wrapped around her and the lights off. I took the hint and climbed in next to her, spooning her gently as we fell asleep.

*        *        *

Kylie had to go early the next morning, but she invited me to visit her at uni for Valentine's weekend, a little over two weeks away. She said there was a big party on campus and that she had already got me a present. It sounded fun and I spent the next fortnight looking for something perfect for her. Eventually I found a necklace that would discretely fit the key to my cage inside and figured that I would also do the traditional roses and chocolates thing too.

Kylie met me from the train station on Friday night, where I handed over the flowers. She smiled sweetly, kissed me and drove me back to the house she was sharing with some university friends.

We picked up a takeaway and ate it in the lounge with some of her other friends, before going up to her room to watch a movie. I gave her the chocolates and the necklace and she was delighted. She told me she had something special for me too, but would give it to me later in the weekend.

After the movie, she made me strip down to nothing but the cage. She took her clothes off too and proceeded to sit on top of me and made me lick her while she teased me through the cage. I eagerly obeyed and soon found my face soaked with her delicious juices.

I couldn’t see anything, but felt the cage suddenly loosen and come off, followed by the ring and strap. I gasped at the feeling of freedom as Kylie gently rubbed lube into my cock, which was struggling to erect itself after so many weeks locked up. I dived deeper into her, licking her pussy and ass with everything I could muster, as she stroked me to attention and began slowly bringing me towards an edge. She held back and kept me from cumming while I brought her to another orgasm.

My world was suddenly flooded with light as she climbed off of me, turned around and straddled my thighs, holding my cock gently and lifting herself on top of me. She lowered herself onto me, my cock suddenly flooded with the sensation of her warm, wet pussy. I gasped with pleasure, squirmed with delight and groaned softly as she moved expertly backwards and forwards, watching my face, moaning gently and occasionally closing her eyes and letting out a gasp.

Within only a few minutes, I was gushing cum into her with a series of grunts and groans. She gasped and moaned too and I felt a wave of pleasure unlike any I had experienced in months. As soon as I had finished cumming, she lifted herself and climbed up the bed, so that her pussy was directly over my face.
‘You know what to do,’ she said.
I put my hands on her ass, strained my neck and licked as my cum slowly poured out of her, into my mouth and onto my face.
‘Mmmm,’ she moaned. ‘That’s nice.’

We showered together afterwards, making out and fucking again, before going to bed. I woke early the next morning, so I got dressed and made some breakfast. We spent the morning in bed, frolicking and chatting and watching rubbish television.

She said as I had behaved so well and let her throw my boxers away, I could have the day off from the cage. It felt weird not being in the cage and it made wearing panties awkward and uncomfortable - instead of a snug fit around it. I became so conscious of my cock and balls as we went about the day, that I found it hard to enjoy myself and feel normal.

When we were getting ready for the night out, Kylie tried on a variety of sexy dresses, while I watched her, rock hard inside my jeans. Once she had settled on an outfit, she did her hair and make-up while I watched some TV. About ten minutes before we were due to leave, she suddenly declared it was time to give me her Valentine’s Day present.

‘But we’re about to go out,’ I said puzzled.
‘You’ll need it,’ she told me, handing me over a small neatly wrapped box.
I opened it with a smile and revealed a chastity cage, similar to the one I had been wearing, only significantly smaller, a ‘nub’ style device only a few centimetres long.
‘It’s tiny,’ I said.
‘Well, it’s not like you fill up the other one,’ she chuckled. ‘Come on, let’s try it on.’

I lowered my jeans and panties and managed to put the device on with surprising ease. It was snug but comfortable and it felt better than being loose all day.
‘Perfect,’ she said with a smile, putting the key inside her necklace, which she made me help her put on. ‘There’s one other thing,’ she added.
She handed me a small metal buttplug with a blue jewel in the base and a bottle of lube. ‘You’ll need this.’
‘Really?’
‘Yeah,’ she said, lifting her up skirt and pulling her panties aside slightly to reveal the buttplug she had put in whilst in the bathroom, this one with a pink jewel. ‘We can match.’

We danced and drank that night with her friends and the cage was surprisingly comfortable for the most part, apart from when she rubbed herself against me while dancing. The buttplug was more or less constantly on my mind, though I was fairly accustomed to wearing them. By the end of the night, I had soaked my panties and Kylie had soaked hers too - in fact, at one point she took them off and handed them to me to stuff into my pocket. This turned me on considerably and when we were in the taxi back to hers she made me finger her to show me how turned on she was too.

I was convinced she would let me out to fuck her when we got back, but instead she lay back and made me use a variety of dildos and toys on her until she had had several orgasms.

The next morning, I asked her how long she would keep me caged for this time. Once again, her reply was ambiguous. ‘We will see.’

 *        *        *

The next few weeks were filled with tasks and teasing until her next planned visit to mine was coming up. We had taken to sometimes playing little games on the messenger platform we used, backgammon, uno and go, while we chatted.

The smaller cage had taken some getting used to, it was much more limiting in terms of erections and made aiming a little challenging when going to the toilet - a problem that was easily eliminated with a minor adjustment and only sitting down to pee. Kylie loved it, would talk often about how much better the smaller cage suited me and praised me consistently for wearing it. With every ‘good boy’ and ‘well done’, I found myself becoming more and more compliant with her wishes, melting into a newly found praise fetish.

About a week before her next visit, 4 or 5 weeks after Valentine's, we were playing games online when I brought up the subject of being unlocked.
‘Will you unlock me when you visit next week?’ I asked.
‘I haven't decided yet, maybe.’
‘Will I get to fuck you?’
‘I doubt it.’

I must have annoyed her with my questions, because she went quiet for a few minutes before coming back with a proposal. ‘I was thinking you would get a blowjob, after getting me off a few times, but now that you've kept asking I've decided it will be a hand- no, a footjob, which I may ruin and you will have to lick up.

‘But I will give you a chance to redeem yourself. You can either accept these terms or gamble them. If you choose to gamble we will play some games and if you win I'll upgrade you to a blowjob, which I will swallow, but if you lose you will stay locked. What will it be?’
‘I'll take the gamble,’ I said without hesitation.
‘Okay,’ she said. ‘So we will keep score all week of who wins the most games and on Friday, you will know your fate.’

I would love to say it was a close contest, but that would be lying: she thrashed me. Over the course of the week I just seemed to mount up more and more losses and eventually it was clear that my efforts were hopeless. I tried to negotiate but she wouldn't have any of it.

Her visit was torment; she spent most of the weekend naked or in her underwear, demanding I lick her, finger her or bring her to orgasm with a dildo anytime she pleased. She wouldn’t let me wear clothes unless we ventured out, which as the weather was terrible, was only a couple of brief trips to the shop downstairs and a cafe around the corner.

She gave me long lingering blowjobs through the cage, straddled me for make out sessions, rubbed her ass and her tits against my constantly leaking package. It was non-stop agony, but I loved every second of it. I worshipped every inch of her body. She spanked me just because she ‘felt like it’ and tied me down to the bed for long teasing sessions. I was a quivering mess by the time she left.

While she was over, we also planned a trip away together, a few days in a cabin out in a beautiful part of the countryside, with waterfalls and lakes close by. We booked it in for a month’s time, when we both had some time off of uni, and made our travel plans.

I tried to resist the urge to ask, but before she left, I couldn’t help but ask her. ‘Will I get unlocked when we go away?’
She gave me a wicked smile. ‘Oh yes, I have something special planned.’
‘Will I get to cum?’
‘You’ll have the opportunity, it will depend on you.’
She gave me one last, lingering kiss before leaving and reminded me to be a good boy for her between now and our little holiday.

*        *        *

It was a long drive up to the cabin and Kylie was cross at me because I had kept falling asleep while she was driving. When we arrived, she made me carry everything into the cabin from the car while she took a quick shower. She followed this up with some spanking and then sent me in for a shower while she prepared us some food.

We ate dinner, opened a bottle of wine and sat on the veranda talking for a while until it was too cold and the wine was finished. When we headed into the bedroom, Kylie ordered me to strip down and lay on the bed. She tied my hands and ankles to the four posts and blindfolded me. I waited quietly in the darkness while she shuffled around the room.

When she removed the blindfold, she was on all fours above me, wearing a gorgeous lingerie set, a sheer red nighty with matching lace panties. I looked her up and down and whispered, ‘wow!’
She smiled, stood up and gave me a twirl and danced seductively to the soft music before climbing back onto the bed and kneeling between my legs.
‘Here’s the deal,’ she explained. ‘We’re here for four nights and every night, before bed, you will get unlocked and have a chance to cum.’
I nodded my understanding, ‘Yes mistress, thank you mistress.’
‘I am going to unlock you and give you a handjob. If you can cum within three minutes, I will let you, but if you can’t, I will stop and lock you back up.’

Kylie unlocked and removed the cage and watched my cock spring into life. She set a timer on her phone and placed it on my belly so that we both could see it. She hit the start button and started stroking, slowly. She gradually picked up the pace, getting faster and faster until, just before the two and a half minute mark, I erupted with a deep groan. She continued stroking and allowed me to enjoy the full orgasm as squirt over squirt sprayed over her hands, my belly and chest and a few drops falling onto her cleavage.

The timer beeped, she let go, grabbed some tissues and began mopping up the mess and, true to her word, locked me straight back up, almost forcing the cage onto my still quivering cock.

On the second day of our holiday, we lounged around the cabin in the morning and took a long walk around the lake, stopping for lunch at a pub on the opposite shore before completing the loop. We were both fairly exhausted when we made it back and took a long shower together, my cock still caged while I washed Kylie’s back and legs.

We ate a simple meal and sat in front of the fire playing cards, before retiring to the bedroom, where once again she ordered me naked and tied me down. There was no lingerie tonight, just a baggy t-shirt and her ‘mistress’ thong.

‘We’re going to do the same thing as last night,’ she explained. ‘Only this time, you only have one minute.’

She set the timer, placed it on my belly, unlocked and gave me a few seconds to adjust to the freedom before beginning. She stroked quickly but by the time her phone beeped, I was barely on edge and she released and let me quiver.
‘Time’s up,’ she declared. ‘We will have to try again tomorrow.’
She took some ice from the freezer and used it to soften me enough to fit back in the cage. She untied me and we cuddled up and drifted to sleep.

On day three we drove to a famous waterfall and then headed into a historic town and visited their church and castle and perused a good sized antiques market. We ate dinner in an Italian restaurant and drove back to the cabin for the evening routine.

This time, Kylie got naked for the brief unlock and after a day of lots of teasing little touches, looks and whispers, I felt more prepared. I came after 48 seconds and Kylie laughed.
‘I am going to ruin your resistance,’ she chuckled. ‘Tomorrow, we will aim for thirty.’

We had a lazier day the following day, not going too far and enjoying the space around the cabin. We drove out to a supermarket to pick up something for the dinner Kylie ordered me to cook for her. I complied and we drank a bottle of wine for dinner and enjoyed the fire before moving into the bedroom for our final night in the cabin.

Once again, she tied me up, stripped off and unlocked me. She set the timer and set to fast stroking from the start. I was desperately horny and reached the edge after eighteen seconds, it took a little longer to make me cum but at the 22 second mark I spurted, still mid orgasm when the timer beeped and Kylie let go. I twitched for another thirty seconds or so.
‘That was impressive. Nice and quick!’ Kylie said. ‘I’m glad you managed that.’

She cleaned me up and put the cage back on before untying me. We both slept soundly and in the morning she made me worship her ass and pussy for a long time before we got up, packed out things and headed on our way.

It was a crazy few days and set the tone for the next period of our relationship, lengthy lock ups with brief unlocks and opportunities to cum in humiliating ways, if I completed the tasks Kylie set for me. It was an exciting pattern, but that summer things would take a turn...

reddit.com
u/Afraid-Flan4278 — 1 month ago

Kylie's Tasks

The next instalment from my collection (available in full on Kindle), about my long-distance uni girlfriend who become my mistress and the fun we had. My chastity sentences have begun to get longer with greater challenges on the rare occasions we see each other. The previous instalment is here.

After being locked back in my chastity cage on New Year’s Day, I went back to uni a couple of days later with no fixed plans to see Kylie again soon, or any knowledge of when I would next be unlocked. We had discussed Valentine's Day in passing, but had not confirmed anything.

We had the usual chats online a few times a week, sometimes casual and sometimes spicy. I had become quite accustomed to the cage already and although it was tight and uncomfortable when I was turned on, it was mostly a pleasant feeling. Sometimes, when my mind wandered, I found myself leaking large amounts of precum, which felt very strange at first but was something I began to really enjoy. Kylie got off on it too, when I would tell her about it or send her pictures.

I’d become increasingly submissive, not just to Kylie, but in general. Yet it felt empowering, and I found that I had more motivation towards uni work, my fitness, keeping my flat clean and towards my hobbies. Something about the limitations it imposed on me, about the constant little reminders, sharpened me and gave me a new drive.

One wet Saturday morning, right at the end of January, I was at home having just got back from a trip to the grocery store, when the doorbell rang. I headed down the stairs and opened the door, which was on the side of the corner shop below me, to reveal Kylie standing there in a raincoat. I let her in and we headed upstairs where I made her a cup of tea to warm her up.

‘My plans got cancelled, so I thought I would surprise you,’ she explained.
‘It’s a good surprise.’

We drank the tea and chatted for a little while, gossiping and joking about various topics. We made out for a little while on my sofa and I could feel precum leaking from me continuously. She reached down and undid my jeans, pulling down the zip and grabbing the waistband and revealing my boxers.

‘What’s this?’ she demanded.
I gave her a curious look.
‘I told you that you were only allowed to wear panties when we’re together.’
‘I know,’ I said, defending myself. ‘But I didn’t know you were coming.’
‘That is not an excuse - let’s get you changed now,’ her tone was serious and she marched me into the bedroom and made me take off the boxers and replace them with a pink and gold g-string with the word ‘angel’ emblazoned across the crotch.

‘Much better,’ she said as she made me give her a twirl before putting my jeans back on. ‘We need to make sure this doesn’t happen again.’
She opened up my underwear drawer and took out all the boxershorts, leaving behind only my collection of women’s underwear - about a dozen pairs. She placed the boxers in a grocery bag that was on the kitchen side and told me to get ready to go out.
‘Let’s get rid of these for good.’

We headed out for lunch at a cafe in town and Kylie made me deposit the bag of underwear in a public bin on the way.
‘No more boy pants for you,’ she declared with a vicious smile.

After lunch we went to the cinema; I struggled to concentrate on the movie because Kylie’s hand was caressing my leg or feeling my cage through my jeans the whole time. I was unfathomably horny.

We walked back to my flat and I cooked us dinner, which we ate with a bottle of wine whilst watching some half-baked comedy programme.

When the show finished, she led me to the bedroom, undressed and lay on the bed. She beckoned me over and I climbed on top of her, missionary style. She grabbed me and kissed me and held me against her, my cage pressed against her naked thigh. I kissed her neck and her breasts, groaning softly all the time. She pushed me further down and I kissed her stomach, her thighs and eventually plunged my face between her legs and began licking, kissing and sucking her clit.

I looked up at her and saw her fondling the key and the chain between her fingers. I redoubled my efforts and worked as hard as I could to make her cum as hard as possible, which she did, over and over again. Each time I would look up, to see if she was satisfied enough to unlock me, but each time she would just push my head back down for more.

After what felt like hours and both of us soaked in sweat and cum, Kylie stopped me and told me she was going for a shower. I lay there in the bed, jaw and tongue aching, dripping gallons of precum through the holes in the cock-cage. When Kylie returned, wrapped in a towel, she sent me to take a shower too, ‘better make it a cold one,’ she added with a grin. When I returned, Kylie was in bed, naked but with the covers wrapped around her and the lights off. I took the hint and climbed in next to her, spooning her gently as we fell asleep.

*        *        *

Kylie had to go early the next morning, but she invited me to visit her at uni for Valentine's weekend, a little over two weeks away. She said there was a big party on campus and that she had already got me a present. It sounded fun and I spent the next fortnight looking for something perfect for her. Eventually I found a necklace that would discretely fit the key to my cage inside and figured that I would also do the traditional roses and chocolates thing too.

Kylie met me from the train station on Friday night, where I handed over the flowers. She smiled sweetly, kissed me and drove me back to the house she was sharing with some university friends.

We picked up a takeaway and ate it in the lounge with some of her other friends, before going up to her room to watch a movie. I gave her the chocolates and the necklace and she was delighted. She told me she had something special for me too, but would give it to me later in the weekend.

After the movie, she made me strip down to nothing but the cage. She took her clothes off too and proceeded to sit on top of me and made me lick her while she teased me through the cage. I eagerly obeyed and soon found my face soaked with her delicious juices.

I couldn’t see anything, but felt the cage suddenly loosen and come off, followed by the ring and strap. I gasped at the feeling of freedom as Kylie gently rubbed lube into my cock, which was struggling to erect itself after so many weeks locked up. I dived deeper into her, licking her pussy and ass with everything I could muster, as she stroked me to attention and began slowly bringing me towards an edge. She held back and kept me from cumming while I brought her to another orgasm.

My world was suddenly flooded with light as she climbed off of me, turned around and straddled my thighs, holding my cock gently and lifting herself on top of me. She lowered herself onto me, my cock suddenly flooded with the sensation of her warm, wet pussy. I gasped with pleasure, squirmed with delight and groaned softly as she moved expertly backwards and forwards, watching my face, moaning gently and occasionally closing her eyes and letting out a gasp.

Within only a few minutes, I was gushing cum into her with a series of grunts and groans. She gasped and moaned too and I felt a wave of pleasure unlike any I had experienced in months. As soon as I had finished cumming, she lifted herself and climbed up the bed, so that her pussy was directly over my face.
‘You know what to do,’ she said.
I put my hands on her ass, strained my neck and licked as my cum slowly poured out of her, into my mouth and onto my face.
‘Mmmm,’ she moaned. ‘That’s nice.’

We showered together afterwards, making out and fucking again, before going to bed. I woke early the next morning, so I got dressed and made some breakfast. We spent the morning in bed, frolicking and chatting and watching rubbish television.

She said as I had behaved so well and let her throw my boxers away, I could have the day off from the cage. It felt weird not being in the cage and it made wearing panties awkward and uncomfortable - instead of a snug fit around it. I became so conscious of my cock and balls as we went about the day, that I found it hard to enjoy myself and feel normal.

When we were getting ready for the night out, Kylie tried on a variety of sexy dresses, while I watched her, rock hard inside my jeans. Once she had settled on an outfit, she did her hair and make-up while I watched some TV. About ten minutes before we were due to leave, she suddenly declared it was time to give me her Valentine’s Day present.

‘But we’re about to go out,’ I said puzzled.
‘You’ll need it,’ she told me, handing me over a small neatly wrapped box.
I opened it with a smile and revealed a chastity cage, similar to the one I had been wearing, only significantly smaller, a ‘nub’ style device only a few centimetres long.
‘It’s tiny,’ I said.
‘Well, it’s not like you fill up the other one,’ she chuckled. ‘Come on, let’s try it on.’

I lowered my jeans and panties and managed to put the device on with surprising ease. It was snug but comfortable and it felt better than being loose all day.
‘Perfect,’ she said with a smile, putting the key inside her necklace, which she made me help her put on. ‘There’s one other thing,’ she added.
She handed me a small metal buttplug with a blue jewel in the base and a bottle of lube. ‘You’ll need this.’
‘Really?’
‘Yeah,’ she said, lifting her up skirt and pulling her panties aside slightly to reveal the buttplug she had put in whilst in the bathroom, this one with a pink jewel. ‘We can match.’

We danced and drank that night with her friends and the cage was surprisingly comfortable for the most part, apart from when she rubbed herself against me while dancing. The buttplug was more or less constantly on my mind, though I was fairly accustomed to wearing them. By the end of the night, I had soaked my panties and Kylie had soaked hers too - in fact, at one point she took them off and handed them to me to stuff into my pocket. This turned me on considerably and when we were in the taxi back to hers she made me finger her to show me how turned on she was too.

I was convinced she would let me out to fuck her when we got back, but instead she lay back and made me use a variety of dildos and toys on her until she had had several orgasms.

The next morning, I asked her how long she would keep me caged for this time. Once again, her reply was ambiguous. ‘We will see.’

 *        *        *

The next few weeks were filled with tasks and teasing until her next planned visit to mine was coming up. We had taken to sometimes playing little games on the messenger platform we used, backgammon, uno and go, while we chatted.

The smaller cage had taken some getting used to, it was much more limiting in terms of erections and made aiming a little challenging when going to the toilet - a problem that was easily eliminated with a minor adjustment and only sitting down to pee. Kylie loved it, would talk often about how much better the smaller cage suited me and praised me consistently for wearing it. With every ‘good boy’ and ‘well done’, I found myself becoming more and more compliant with her wishes, melting into a newly found praise fetish.

About a week before her next visit, 4 or 5 weeks after Valentine's, we were playing games online when I brought up the subject of being unlocked.
‘Will you unlock me when you visit next week?’ I asked.
‘I haven't decided yet, maybe.’
‘Will I get to fuck you?’
‘I doubt it.’

I must have annoyed her with my questions, because she went quiet for a few minutes before coming back with a proposal. ‘I was thinking you would get a blowjob, after getting me off a few times, but now that you've kept asking I've decided it will be a hand- no, a footjob, which I may ruin and you will have to lick up.

‘But I will give you a chance to redeem yourself. You can either accept these terms or gamble them. If you choose to gamble we will play some games and if you win I'll upgrade you to a blowjob, which I will swallow, but if you lose you will stay locked. What will it be?’
‘I'll take the gamble,’ I said without hesitation.
‘Okay,’ she said. ‘So we will keep score all week of who wins the most games and on Friday, you will know your fate.’

I would love to say it was a close contest, but that would be lying: she thrashed me. Over the course of the week I just seemed to mount up more and more losses and eventually it was clear that my efforts were hopeless. I tried to negotiate but she wouldn't have any of it.

Her visit was torment; she spent most of the weekend naked or in her underwear, demanding I lick her, finger her or bring her to orgasm with a dildo anytime she pleased. She wouldn’t let me wear clothes unless we ventured out, which as the weather was terrible, was only a couple of brief trips to the shop downstairs and a cafe around the corner.

She gave me long lingering blowjobs through the cage, straddled me for make out sessions, rubbed her ass and her tits against my constantly leaking package. It was non-stop agony, but I loved every second of it. I worshipped every inch of her body. She spanked me just because she ‘felt like it’ and tied me down to the bed for long teasing sessions. I was a quivering mess by the time she left.

While she was over, we also planned a trip away together, a few days in a cabin out in a beautiful part of the countryside, with waterfalls and lakes close by. We booked it in for a month’s time, when we both had some time off of uni, and made our travel plans.

I tried to resist the urge to ask, but before she left, I couldn’t help but ask her. ‘Will I get unlocked when we go away?’
She gave me a wicked smile. ‘Oh yes, I have something special planned.’
‘Will I get to cum?’
‘You’ll have the opportunity, it will depend on you.’
She gave me one last, lingering kiss before leaving and reminded me to be a good boy for her between now and our little holiday.

*        *        *

It was a long drive up to the cabin and Kylie was cross at me because I had kept falling asleep while she was driving. When we arrived, she made me carry everything into the cabin from the car while she took a quick shower. She followed this up with some spanking and then sent me in for a shower while she prepared us some food.

We ate dinner, opened a bottle of wine and sat on the veranda talking for a while until it was too cold and the wine was finished. When we headed into the bedroom, Kylie ordered me to strip down and lay on the bed. She tied my hands and ankles to the four posts and blindfolded me. I waited quietly in the darkness while she shuffled around the room.

When she removed the blindfold, she was on all fours above me, wearing a gorgeous lingerie set, a sheer red nighty with matching lace panties. I looked her up and down and whispered, ‘wow!’
She smiled, stood up and gave me a twirl and danced seductively to the soft music before climbing back onto the bed and kneeling between my legs.
‘Here’s the deal,’ she explained. ‘We’re here for four nights and every night, before bed, you will get unlocked and have a chance to cum.’
I nodded my understanding, ‘Yes mistress, thank you mistress.’
‘I am going to unlock you and give you a handjob. If you can cum within three minutes, I will let you, but if you can’t, I will stop and lock you back up.’

Kylie unlocked and removed the cage and watched my cock spring into life. She set a timer on her phone and placed it on my belly so that we both could see it. She hit the start button and started stroking, slowly. She gradually picked up the pace, getting faster and faster until, just before the two and a half minute mark, I erupted with a deep groan. She continued stroking and allowed me to enjoy the full orgasm as squirt over squirt sprayed over her hands, my belly and chest and a few drops falling onto her cleavage.

The timer beeped, she let go, grabbed some tissues and began mopping up the mess and, true to her word, locked me straight back up, almost forcing the cage onto my still quivering cock.

On the second day of our holiday, we lounged around the cabin in the morning and took a long walk around the lake, stopping for lunch at a pub on the opposite shore before completing the loop. We were both fairly exhausted when we made it back and took a long shower together, my cock still caged while I washed Kylie’s back and legs.

We ate a simple meal and sat in front of the fire playing cards, before retiring to the bedroom, where once again she ordered me naked and tied me down. There was no lingerie tonight, just a baggy t-shirt and her ‘mistress’ thong.

‘We’re going to do the same thing as last night,’ she explained. ‘Only this time, you only have one minute.’

She set the timer, placed it on my belly, unlocked and gave me a few seconds to adjust to the freedom before beginning. She stroked quickly but by the time her phone beeped, I was barely on edge and she released and let me quiver.
‘Time’s up,’ she declared. ‘We will have to try again tomorrow.’
She took some ice from the freezer and used it to soften me enough to fit back in the cage. She untied me and we cuddled up and drifted to sleep.

On day three we drove to a famous waterfall and then headed into a historic town and visited their church and castle and perused a good sized antiques market. We ate dinner in an Italian restaurant and drove back to the cabin for the evening routine.

This time, Kylie got naked for the brief unlock and after a day of lots of teasing little touches, looks and whispers, I felt more prepared. I came after 48 seconds and Kylie laughed.
‘I am going to ruin your resistance,’ she chuckled. ‘Tomorrow, we will aim for thirty.’

We had a lazier day the following day, not going too far and enjoying the space around the cabin. We drove out to a supermarket to pick up something for the dinner Kylie ordered me to cook for her. I complied and we drank a bottle of wine for dinner and enjoyed the fire before moving into the bedroom for our final night in the cabin.

Once again, she tied me up, stripped off and unlocked me. She set the timer and set to fast stroking from the start. I was desperately horny and reached the edge after eighteen seconds, it took a little longer to make me cum but at the 22 second mark I spurted, still mid orgasm when the timer beeped and Kylie let go. I twitched for another thirty seconds or so.
‘That was impressive. Nice and quick!’ Kylie said. ‘I’m glad you managed that.’

She cleaned me up and put the cage back on before untying me. We both slept soundly and in the morning she made me worship her ass and pussy for a long time before we got up, packed out things and headed on our way.

It was a crazy few days and set the tone for the next period of our relationship, lengthy lock ups with brief unlocks and opportunities to cum in humiliating ways, if I completed the tasks Kylie set for me. It was an exciting pattern, but that summer things would take a turn...

reddit.com
u/Afraid-Flan4278 — 1 month ago

New Years Eve Party - based on a true story

Another story from my latest collection, which is available in full on Kindle. These stories are all based on true events with my long-distance girlfriend during my university years, who locked me in chastity and became my Mistress. I will gradually post them all on here. You can find the previous stories on my reddit page.

One of Kylie’s friends was hosting a New Year’s Eve party and we were invited. They lived about an hour away and Kylie had arranged for us to stay in their summer house with her another friend and her boyfriend.

She picked me up early in the evening and when I climbed into the car she initiated a ‘pantie inspection’, as she liked to call it. I unzipped my jeans and folded them back to reveal a pale blue cotton thong that barely covered my chastity cage, one of the ones she had bought me for Christmas.
‘Very nice,’ she said. ‘Let’s just hope we don’t end up playing strip beer pong again.’
A panicked look crossed my face.
‘Don’t worry,’ she laughed. ‘Beth isn’t the sort, she thinks herself far too classy.’

The drive was almost an hour and we stopped at a supermarket on the way to pick up some alcohol. Kylie picked up a bottle of tequila, one of her favourites, and a box of blue raspberry flavoured alcopops. I went to grab a case of beer but Kylie was quick to stop me.
‘No, no,’ she said. ‘You’re having these too,’ she nodded towards the blue drinks.
‘What? But they’re girly and blue!’
‘They match your underwear then,’ she said with a smirk. ‘Now grab another box.’
I did as I was told and followed her to the till, where we paid and took everything out to the car to resume our journey.

Beth’s house was big, with a huge garden. The ‘summer house’ was far from what I imagined, it had two bedrooms, a living space and its own bathroom. Becky and Shaun had already arrived and claimed one of the rooms, so we put our stuff in the other one and headed into the main house.

The party was just getting underway and other people were starting to arrive. It ended up being quite a large affair, with Beth’s brother DJing the in living room, where they had moved furniture to create a dancefloor. Kylie and I danced for a little while and then headed into the kitchen where most of her main friends were.

One of her closest friends, Cat, who had been at Kylie’s party back in the summer came over to us.
‘Hi Frank,’ she said to me. ‘Nice to see you’ve kept your clothes on at this party.’
I blushed a little and Kylie and some of the others laughed.
‘Grab another couple of our drinks from the fridge,’ Kylie told me.

I smiled and silently walked across the kitchen to the giant refrigerator that was full of partygoers’ cans and bottles. I pulled out two blue drinks, opened them with a nearby bottle opener and took them over.
‘Thanks girlpants,’ she said, the nickname slipping out by accident.
‘Girlpants?’ Becky asked while the rest of the group laughed.
‘Yeah,’ replied with a cocky grin. ‘I call him girlpants because he’s so soppy.’
I blushed and they all laughed again. Although I was embarrassed, I was grateful Kylie didn’t tell them the real reason.

Kylie was simultaneously demanding and playful all through the party and we laughed and danced and chatted together and with her friends as the hours rolled by. When midnight came everyone gathered for the countdown and we all cheered, hugged and kissed before the dancing and drinking continued.

It was very late when we finally made our way to the bedroom in the summerhouse, with most of Beth’s friends living closer and heading home by foot or taxi. Becky and Shaun were already in their room with the door closed and we slipped into the next room and onto the bed where we began fiercely making out.

I slipped my hand under her dress and up her thigh as we were kissing, slipping my fingers past the ‘mistress’ panties I’d bought her and inside her already wet pussy. She grabbed my caged cock through my jeans and squeezed while I kissed and fingered her as we both moaned gently.

‘Shh!’ she interrupted. ‘Listen a second.’
I froze, fingers still inside her and kept quiet. A rhythmic dull thud and soft groans were seeping through the walls from the room next door.
‘Keep going,’ she said. ‘I want to listen.’
I got into a comfortable position and carried on fingering her while Becky's moans increased in volume and pace. Kylie closed her eyes and breathed deeply as she began softly moaning too.

I manoeuvred myself between her legs, slipped off her panties and began licking her while I fingered, rubbing her g-spot with a soft rhythm and letting my tongue dance over her sensitive clit. She tasted sweet, it had become a familiar and comforting duty. I had always been good with my tongue and Kylie ensured a practice regularly to improve further. My cock, meanwhile, strained uselessly in its cage.

Kylie’s hand gripped the back of my head and she wrapped a leg around the small of my back, holding me firmly in place as I plunged deeper and harder, using my mouth and fingers as she groaned and grew wetter and wetter. The sounds from next door grew louder too, the repeated thuds grew faster and Becky’s moans higher in pitch. I wondered if this had suddenly become a competition.

Becky’s moans reached a crescendo, followed by an almost bark-like grunt from Shaun and an instant later Kylie let out a long shivering sigh-like groan, followed by an intense shaking orgasm. She released her grip and I manoeuvred myself away, kissed her thighs delicately and lay down beside her.

She sat up momentarily, removed her crumpled dress and lay back down, putting an arm around me.
‘That was fun!’ she smiled, as I cuddled up to her, placing my head on her chest.
I glanced down at my caged cock. ‘Fun enough to unlock me?’
She chuckled and rolled slightly to one side, ‘Maybe in the morning.’

*        *        *

We both stripped naked in the night and when I woke up, I was spooning Kylie and my penis was attempting to get hard inside the cage. It was not painful, just uncomfortable and I rolled onto my back and lay still, concentrating on my breathing to try to get my attempted erection to subside.

I drifted back to sleep for a while and when I woke up, it was the same uncomfortable sensation of my body trying to rouse my dick into action. I opened my eyes and saw Kylie, naked, straddling my legs, with the chastity cage in her mouth. She looked up at me with sexy bedroom eyes and let her tongue flick through the gaps.

My eyes rolled into the back of my head, she caressed my balls and squeezed them gently.
‘Do you like that?’ she asked.
I nodded eagerly, ‘Yes.’
‘Yes what?’ she smiled saucily.
‘Yes mistress.’
‘That’s better,’ she said before resuming teasing me with her mouth.

After a long minute, she lifted her head, precum following her as she moved away. She walked over to her bag and returned with a vibrator, which she flicked on and pressed against the cage.

I gasped and groaned and squirmed but she held it close as my cock swelled even more. Kylie chuckled as she passed it over my balls and watched my eyes roll back again.

She put the vibrator aside and held her hand towards me, the key dangling from her fingers. I smiled and nodded eagerly.
‘Please unlock me,’ I gasped. ‘Please!’
She slowly put the key in the lock and removed the front half of the cage, before carefully slipping off the ring and strap, giving my dick as little contact as possible.

I sighed with relief and we both watched as it twitched into life, fully erect within only a few seconds.

‘Did you enjoy last night?’ she asked as she gently caressed it with her fingertips.
‘Yeah, it was fun.’
‘Mhm. I enjoyed you getting me off while I listened to them fucking next door.’
I smiled as she wrapped a hand around and began slowly stroking.
‘It is very different to what happened last year,’ she told me.
‘What happened last year?’ I said between deep breaths as she teased my cock.

She leant forward, her lips inches away from my leaking tip and blew gently, smiling as I twitched and strained for more. She ran her fingers lightly over the precum and spat gently onto the head of my cock, using the combined fluids as lube and began stroking again, still agonisingly slowly.

‘Becky and Shaun had a big argument in the garden,’ she explained. ‘They were pretty drunk. She went inside with the girls and Shaun stormed off into the woods at the back of the house.’
‘Mhm,’ I replied, barely listening, just enjoying the teasing sensation of Kylie’s skilled hands.
‘So I followed Shaun into the woods and we talked about it for a little while.’ She had picked up the pace slightly and I could feel myself moving towards an edge, Kylie sensed it too and released her grip slightly, letting me squirm for a moment before resuming, slowly.
‘What happened then?’ I asked.
‘We talked for a while,’ she continued. ‘He told me about the argument and that they had been having a rough few weeks. He was pretty down about it all, so I decided to cheer him up.’
My eyes opened wide, ‘What did you do?’ I gasped.
‘I gave him a blowjob,’ she said with a smile.
‘Really?’
‘Yeah, out in the woods. Becky had always bragged about how big he was and I wanted to see for myself.’
‘Was he?’
‘Yeah, big and thick. I would have let him fuck but he came before I had the chance to offer.’

She was stroking me faster now and I could feel the edge building.
‘Where did he come?’ I asked, intrigued and incredibly aroused.
‘In my mouth of course,’ she replied with a smile.
‘Did you swallow?’
‘Absolutely, a nice big thick load.’

I gasped and groaned as I came towards the edge.
‘I’m going to cum,’ I told her.
She instantly let go of my cock and let it twitch and throb as the cum dribbled out of me in a series of pathetic squirts - my orgasm ruined. I groaned in frustration.

As soon as I had stopped cumming, Kylie bent her head down and began licking the cum off of my cock, balls and thighs gently, sucking up every drop and swallowing it.
‘Just like that,’ she said with a smile.

I took a quick shower in the shared bathroom of the summer house, Becky and Shaun were still asleep. When I returned to our room, Kylie was dressed and had laid out my clothes, including a pair of panties and the chastity cage on the bed. She watched as I locked back up, dressed and handed her the key.
‘Good boy’ she said with a grin.
‘How long are you going to keep me locked up this time?’
‘I’m not sure yet. You’re not in a rush are you?’
I shook my head.
She kissed me softly and whispered in my ear, ‘There’s plenty of fun to come.’

reddit.com
u/Afraid-Flan4278 — 1 month ago

New Years Eve Party [chastity] [voyeurism] [femdom] [ruined orgasms]

Another story from my latest collection. These stories are all based on true events with my long-distance girlfriend during my university years, who locked me in chastity and became my Mistress. I will gradually post them all on here. You can find the previous stories on my reddit page.

One of Kylie’s friends was hosting a New Year’s Eve party and we were invited. They lived about an hour away and Kylie had arranged for us to stay in their summer house with her another friend and her boyfriend.

She picked me up early in the evening and when I climbed into the car she initiated a ‘pantie inspection’, as she liked to call it. I unzipped my jeans and folded them back to reveal a pale blue cotton thong that barely covered my chastity cage, one of the ones she had bought me for Christmas.
‘Very nice,’ she said. ‘Let’s just hope we don’t end up playing strip beer pong again.’
A panicked look crossed my face.
‘Don’t worry,’ she laughed. ‘Beth isn’t the sort, she thinks herself far too classy.’

The drive was almost an hour and we stopped at a supermarket on the way to pick up some alcohol. Kylie picked up a bottle of tequila, one of her favourites, and a box of blue raspberry flavoured alcopops. I went to grab a case of beer but Kylie was quick to stop me.
‘No, no,’ she said. ‘You’re having these too,’ she nodded towards the blue drinks.
‘What? But they’re girly and blue!’
‘They match your underwear then,’ she said with a smirk. ‘Now grab another box.’
I did as I was told and followed her to the till, where we paid and took everything out to the car to resume our journey.

Beth’s house was big, with a huge garden. The ‘summer house’ was far from what I imagined, it had two bedrooms, a living space and its own bathroom. Becky and Shaun had already arrived and claimed one of the rooms, so we put our stuff in the other one and headed into the main house.

The party was just getting underway and other people were starting to arrive. It ended up being quite a large affair, with Beth’s brother DJing the in living room, where they had moved furniture to create a dancefloor. Kylie and I danced for a little while and then headed into the kitchen where most of her main friends were.

One of her closest friends, Cat, who had been at Kylie’s party back in the summer came over to us.
‘Hi Frank,’ she said to me. ‘Nice to see you’ve kept your clothes on at this party.’
I blushed a little and Kylie and some of the others laughed.
‘Grab another couple of our drinks from the fridge,’ Kylie told me.

I smiled and silently walked across the kitchen to the giant refrigerator that was full of partygoers’ cans and bottles. I pulled out two blue drinks, opened them with a nearby bottle opener and took them over.
‘Thanks girlpants,’ she said, the nickname slipping out by accident.
‘Girlpants?’ Becky asked while the rest of the group laughed.
‘Yeah,’ replied with a cocky grin. ‘I call him girlpants because he’s so soppy.’
I blushed and they all laughed again. Although I was embarrassed, I was grateful Kylie didn’t tell them the real reason.

Kylie was simultaneously demanding and playful all through the party and we laughed and danced and chatted together and with her friends as the hours rolled by. When midnight came everyone gathered for the countdown and we all cheered, hugged and kissed before the dancing and drinking continued.

It was very late when we finally made our way to the bedroom in the summerhouse, with most of Beth’s friends living closer and heading home by foot or taxi. Becky and Shaun were already in their room with the door closed and we slipped into the next room and onto the bed where we began fiercely making out.

I slipped my hand under her dress and up her thigh as we were kissing, slipping my fingers past the ‘mistress’ panties I’d bought her and inside her already wet pussy. She grabbed my caged cock through my jeans and squeezed while I kissed and fingered her as we both moaned gently.

‘Shh!’ she interrupted. ‘Listen a second.’
I froze, fingers still inside her and kept quiet. A rhythmic dull thud and soft groans were seeping through the walls from the room next door.
‘Keep going,’ she said. ‘I want to listen.’
I got into a comfortable position and carried on fingering her while Becky's moans increased in volume and pace. Kylie closed her eyes and breathed deeply as she began softly moaning too.

I manoeuvred myself between her legs, slipped off her panties and began licking her while I fingered, rubbing her g-spot with a soft rhythm and letting my tongue dance over her sensitive clit. She tasted sweet, it had become a familiar and comforting duty. I had always been good with my tongue and Kylie ensured a practice regularly to improve further. My cock, meanwhile, strained uselessly in its cage.

Kylie’s hand gripped the back of my head and she wrapped a leg around the small of my back, holding me firmly in place as I plunged deeper and harder, using my mouth and fingers as she groaned and grew wetter and wetter. The sounds from next door grew louder too, the repeated thuds grew faster and Becky’s moans higher in pitch. I wondered if this had suddenly become a competition.

Becky’s moans reached a crescendo, followed by an almost bark-like grunt from Shaun and an instant later Kylie let out a long shivering sigh-like groan, followed by an intense shaking orgasm. She released her grip and I manoeuvred myself away, kissed her thighs delicately and lay down beside her.

She sat up momentarily, removed her crumpled dress and lay back down, putting an arm around me.
‘That was fun!’ she smiled, as I cuddled up to her, placing my head on her chest.
I glanced down at my caged cock. ‘Fun enough to unlock me?’
She chuckled and rolled slightly to one side, ‘Maybe in the morning.’

*        *        *

We both stripped naked in the night and when I woke up, I was spooning Kylie and my penis was attempting to get hard inside the cage. It was not painful, just uncomfortable and I rolled onto my back and lay still, concentrating on my breathing to try to get my attempted erection to subside.

I drifted back to sleep for a while and when I woke up, it was the same uncomfortable sensation of my body trying to rouse my dick into action. I opened my eyes and saw Kylie, naked, straddling my legs, with the chastity cage in her mouth. She looked up at me with sexy bedroom eyes and let her tongue flick through the gaps.

My eyes rolled into the back of my head, she caressed my balls and squeezed them gently.
‘Do you like that?’ she asked.
I nodded eagerly, ‘Yes.’
‘Yes what?’ she smiled saucily.
‘Yes mistress.’
‘That’s better,’ she said before resuming teasing me with her mouth.

After a long minute, she lifted her head, precum following her as she moved away. She walked over to her bag and returned with a vibrator, which she flicked on and pressed against the cage.

I gasped and groaned and squirmed but she held it close as my cock swelled even more. Kylie chuckled as she passed it over my balls and watched my eyes roll back again.

She put the vibrator aside and held her hand towards me, the key dangling from her fingers. I smiled and nodded eagerly.
‘Please unlock me,’ I gasped. ‘Please!’
She slowly put the key in the lock and removed the front half of the cage, before carefully slipping off the ring and strap, giving my dick as little contact as possible.

I sighed with relief and we both watched as it twitched into life, fully erect within only a few seconds.

‘Did you enjoy last night?’ she asked as she gently caressed it with her fingertips.
‘Yeah, it was fun.’
‘Mhm. I enjoyed you getting me off while I listened to them fucking next door.’
I smiled as she wrapped a hand around and began slowly stroking.
‘It is very different to what happened last year,’ she told me.
‘What happened last year?’ I said between deep breaths as she teased my cock.

She leant forward, her lips inches away from my leaking tip and blew gently, smiling as I twitched and strained for more. She ran her fingers lightly over the precum and spat gently onto the head of my cock, using the combined fluids as lube and began stroking again, still agonisingly slowly.

‘Becky and Shaun had a big argument in the garden,’ she explained. ‘They were pretty drunk. She went inside with the girls and Shaun stormed off into the woods at the back of the house.’
‘Mhm,’ I replied, barely listening, just enjoying the teasing sensation of Kylie’s skilled hands.
‘So I followed Shaun into the woods and we talked about it for a little while.’ She had picked up the pace slightly and I could feel myself moving towards an edge, Kylie sensed it too and released her grip slightly, letting me squirm for a moment before resuming, slowly.
‘What happened then?’ I asked.
‘We talked for a while,’ she continued. ‘He told me about the argument and that they had been having a rough few weeks. He was pretty down about it all, so I decided to cheer him up.’
My eyes opened wide, ‘What did you do?’ I gasped.
‘I gave him a blowjob,’ she said with a smile.
‘Really?’
‘Yeah, out in the woods. Becky had always bragged about how big he was and I wanted to see for myself.’
‘Was he?’
‘Yeah, big and thick. I would have let him fuck but he came before I had the chance to offer.’

She was stroking me faster now and I could feel the edge building.
‘Where did he come?’ I asked, intrigued and incredibly aroused.
‘In my mouth of course,’ she replied with a smile.
‘Did you swallow?’
‘Absolutely, a nice big thick load.’

I gasped and groaned as I came towards the edge.
‘I’m going to cum,’ I told her.
She instantly let go of my cock and let it twitch and throb as the cum dribbled out of me in a series of pathetic squirts - my orgasm ruined. I groaned in frustration.

As soon as I had stopped cumming, Kylie bent her head down and began licking the cum off of my cock, balls and thighs gently, sucking up every drop and swallowing it.
‘Just like that,’ she said with a smile.

I took a quick shower in the shared bathroom of the summer house, Becky and Shaun were still asleep. When I returned to our room, Kylie was dressed and had laid out my clothes, including a pair of panties and the chastity cage on the bed. She watched as I locked back up, dressed and handed her the key.
‘Good boy’ she said with a grin.
‘How long are you going to keep me locked up this time?’
‘I’m not sure yet. You’re not in a rush are you?’
I shook my head.
She kissed me softly and whispered in my ear, ‘There’s plenty of fun to come.’

reddit.com
u/Afraid-Flan4278 — 1 month ago

Christmas Presents [chastity] [femdom] [humiliation] [cbt]

A continuation from my previous story. All these are from my latest collection, which is available on Kindle.

I was free for about a week - enjoying daily masturbation over porn or webcam sessions with Kylie, until about two weeks before Christmas while we were on a video call, Kylie told me it was time to lock up again.

She watched me lock myself up and laughed when I struggled to get the cage on due to my erection. Once I had finished, she made me show her close up - she seemed to be really enjoying herself.
‘What shall I do with the key?’ I asked her.
‘Put it in an envelope, seal it up tight and post it to me,’ she said. ‘I want a picture of you putting it in the postbox. I will unlock you at Christmas.’

I followed her instructions and walked straight to the nearest postbox, snapping a picture of me pushing the envelope through the slot, which I sent to her.
‘Good boy,’ she replied. ‘Don’t get too horny over the next couple of weeks.’

She endeavoured to make it difficult for me, teasing me on cam, sending raunchy text messages and pictures and making me watch porn videos every night. After about five days it felt like I was constantly leaking precum and getting turned on at the slightest evocation, whether that was a message from Kylie, talking to an attractive woman in a low cut top at work or uni, or Nicky calling me her ‘thong twin’ when we met up to play pool - even though I showed her I was wearing red boxers that day. She was wearing red boxers too, and that made the ‘twin’ thing even worse.
‘Maybe we should message each other to make sure our underwear matches every morning,’ she joked.

I told Kylie about Nicky’s jokes the next day. She found the fact that she’d seen the thong amusing.
‘If I didn’t know she was a lesbian, I’d think you two were flirting,’ she told me.
'Does it bother you?’ I asked.
‘Not really. But I might have to punish you for it anyway - I’ll think about it.’

The twentieth was my last day of work before Christmas and it was a busy day at the coffee shop with shoppers in and out constantly. It was made worse by the fact that Kylie ordered me to wear a buttplug for as long as I could manage - which ended up being most of my shift. When I got home, I had to change my pants because I had leaked so much precum.

After work and a quick shower, I got the train back to my parents’ for Christmas, getting picked up from the station around 8pm. I had a takeaway with my family and caught up with them before heading to bed exhausted but excited about seeing Kylie the next day.

The next morning, I walked across the village to Kylie’s dad’s house and arrived just after eleven. Her Dad was at work and I walked through the rain with a spring in my step, excited that I would finally be unlocked after twelve long days.

Kylie answered the door wearing a long grey bathrobe with pink trim and immaculate make up. She smiled sweetly and invited me inside. I followed her up the stairs and into her childhood bedroom, which still had a slight teenage feel to the decor.

As soon as we were in the room, she kissed me with a fiery passion, breaking it off momentarily to speak in an enthused tone, ‘God I’ve missed you!’

She kissed me again before I could respond and grabbed me tight. I kissed her back, wrapping my arms around her and letting my horny hands wander her body through the thick material of the bathrobe.

After a long moment, she broke off the kiss and took a step backwards towards the bed. I watched her with a heady mix of lust and curiosity as she undid the bathrobe and let it fall to the floor

Underneath she wore an incredible lacey blue lingerie set that looked glorious over her pale skin, her blonde hair hanging loosely onto her shoulders and her blue eyes beaming at the stunned look on my face.
‘What do you think?’ she said, giving me a twirl.
I stammered, barely able to speak. ‘You look stunning,’ I told her.
‘And look,’ she said, ‘I’ve even got your key right here.’ She pulled at the thin chain around her neck and revealed the small key that was nestled between her breasts.

I stammered again, dazed by how the lingerie seemed to accentuate every curve and how the key hung deep in her cleavage.
She took a step towards me and put her hand onto my crotch, feeling me swelling inside the black plastic of the cage.
‘Let’s see how you’re getting on, shall we?’

She knelt down in front of me, undid my jeans and pulled them down, revealing the lacey purple panties I had chosen out for the occasion.
She glanced up at me with a smile, ‘good choice.’
I removed my hoody and t-shirt while she ran her hands over the lace and commented on the heavy spot of precum leaking through.

She hooked her fingers into the waistband of my girly knickers and slowly pulled them down and let them fall to the ground where I gently kicked them aside. I was straining something fierce inside the cage as she inspected me carefully, her hands resting gently on the side of my thighs.

Kylie’s hands gently caressed my balls, squeezing slightly before running over the hard plastic that engulfed my shaft. She looked up at me with bedroom eyes and smiled. I gasped when she kissed the cage whilst holding gently holding my balls with one hand while the other travelled up the thigh and onto my ass.

She licked the precum off of the tip before taking the cage in her mouth, sucking gently. I felt nothing but the soft squeezing of my balls and the feel of her tongue occasionally running over the gaps. I groaned with frustration and she squeezed my ass while taking the whole cage in her mouth before withdrawing it completely and turning her attention to my balls, which she kissed and sucked on gently. A huge drop of precum leaked onto her cheek, which she wiped off with a finger, which she held up for me to lick clean. I eagerly complied and she sucked me hard while I did so.

After several long minutes, she suddenly stopped, standing up and stepping away. She produced a collar from under the bed, a leather strap with a ring on the front and gestured for me to come towards her and kneel down. I did as I was bid and she put the collar around me and attached a lead.
‘Start kissing,’ she said, pointing at her feet. ‘Every inch of my body, little by little until I decide otherwise.’
I bent low and began planting light kisses on her feet. I have never had a foot fetish as such, but enjoyed the humiliation and soon the kisses became more eager and I caressed them as I let each one linger on her delicate skin.

A tug of the lead indicated it was time for me to move up and I kissed her calves and shins readily, working my way towards her knees and her creamy thighs. I eagerly kissed, licked and nibbled on the warm skin and revelled in the softness and the gently fragrance of her wet pussy hiding behind the pink lace thong. I was fiercely dripping precum onto the carpet, excited that I would soon my licking her and hoping that a good job would see me released and fucking her soon.

A tug of the lead awoke me from my fantasies as she pulled me away and stood up, turning around so that her ass was in front of my face. She didn’t speak, she just waited, so I took the initiative and started kissing her round, peachy cheeks. She passed the lead between her legs and pulled slightly, forcing me closer. I responded by kissing with more passion and putting my hands on her hips as I did so.

She slipped her panties to the floor and tugged at the lead again. I kissed her harder and she pulled my face into her ass. I eagerly used my tongue to lick her hole and listened to her gasp with delight. She pulled me harder and I licked harder and faster, playing my tongue up, down and around in random motions. I manoeuvred my hand between her legs and felt the warmth and wetness of her pussy. I pushed two fingers inside easily as she spread her legs and bent forwards, leaning on the bed. I licked her ass hungrily and fingered her quickly as she gasped and moaned her way to a staggering orgasm that caused her to slump forward onto the bed breathless for a long moment, her grip on the collar loosening and allowing me a moment’s respite.

I made as if to climb onto the bed, but she stopped me.
‘Stay there,’ she said and I waited on my knees at the foot of the bed while she grabbed some items from a bedside drawer and brought them over to me.

First was a pair of bondage cuffs chained together, which she attached to my wrists. She followed this with ankle cuffs, similar chained, which she put on me with a wicked grin.
‘Open your mouth,’ she told me.

I did as I was told and opened my mouth wide as she sat on the edge of the bed. She inserted a gag with a dildo attachment and strapped it in place behind my head. The short end was a couple of inches, the long end was six or seven and a piece of fake leather separated them like the crossguard of a sword. She did it up tight with the short end in my mouth and lay back on the bed, her feet on the floor and her legs spread.

Kylie gave the lead a tug and I manoeuvred myself towards her clumsily on all fours. She spread her pussy open with the fingers of one hand and tugged with the other. I put my cuffed hands up on the bed between her legs and pushed the dildo inside her. She gave a satisfied sigh and tugged on the lead again, pulling me deeper.

I moved my head backwards and forwards in a thrusting motion, gradually getting deeper, harder and faster until my nose was rubbing against her clit. She pulled the lead tight and I pushed backwards and forwards as much as I was able, revelling in the smell of her sweet pussy and the sound of her moans. I could feel the precum dripping from my cage, my cock straining against the unforgiving plastic, but it only drove me to faster and harder thrusts. Her moans rose in volume and then fell quieter again and she released the tension in the lead and pushed my head away gently before half sitting up on the bed.

She patted the bed with her hand and gave a gentle tug on the lead, so I climbed onto the bed, my hands and ankles still cuffed and drool falling from my gagged mouth.
‘Lay down,’ she told me.

I lay on my back, she lifted my hands above my head and climbed on top of me, facing my feet with her ass and pussy poised above me. She took the dildo in one hand and gently lowered herself onto it, her ass cheeks hitting me in the face softly. She began gently bouncing up and down on me, the dildo moving in and out of her and her cum dripping down onto me. She picked up the pace and found a rhythm she enjoyed, her ass being poked with my nose each time she lowered herself, her legs holding me in place. Eventually she gasped loudly and groaned, her wetness covering me in a sticky mess as she lifted herself off the dildo and slumped forward, her hand grabbing my throbbing caged cock forcefully.

‘Ahhh, that was good,’ she said.
I tried to speak through the gag but couldn’t.
She laughed and climbed off of me and the bed.
‘Sit up. I think it’s time for your fun.’ I climbed into a sitting position, still cuffed and gagged and let her pull me to my feet by the lead as she led me across the room and towards the built-in wardrobe opposite the bed.

She opened the double doors and guided me so that I was standing in the frame, facing out into the room. She took a hold of the chain between the handcuffs and clipped them into something above my head. She unclipped the lead and removed the gag, I gasped breathlessly once it was removed, saliva dripping down onto my chest and the floor. She cast them aside and ran her hands over my chest, thighs, ass and finally my balls and aching cock.

She produced the small key from her bra and undid the chastity cage, pulling it off softly, precum almost gushing out once the cage was off. She removed the ring and the strap and put them on the dresser before stepping back and surveying me as my cock twitched eagerly, gradually getting hard for the first time in almost two weeks.

She stepped forward and touched the tip of her finger, it throbbed violently at the slight stimulation and she giggled.
‘Better be careful,’ she said. ‘We don’t want it to go off yet, do we?’
I shook my head wordlessly and watched her as she moved around the room sexily, picking up some soft rope from her dresser and a metal water flask from beside her bed.

She returned to the wardrobe and carefully tied the rope around my cock and balls in a complex arrangement, moving slowly and pausing every time I twitched. Eventually, with my genitals tied up and about 30 centimeters of excess rope dangling between my legs, she stepped back and put a small stall just in front of me. On top of the stall she placed the water bottle, which she tied to the end of the rope.

I looked at her with desperation, shook my head and began to protest.
‘Don’t say a word,’ she told me. ‘Don’t say a word or I will pull the stall away!’
I nodded my comprehension.
‘I mean, I’m going to pull it away anyway, but if you stay quiet you’ll get a nice countdown. Are you ready?’
I shook my head.
‘Ten… nine… eight,’ she counted slowly and my eyes grew wide with fear and anticipation.
‘Seven… six… five.’
I shook my head again but it had no effect.
‘Four… three.’ She kicked the stall away and I yelped loudly at the sudden hard tug on my balls. My breath shot out of my lungs and my knees buckled slightly, my sides felt like I had a terrible stitch and the bottle swayed between my legs like a pendulum, still pulling my balls down. Somehow, my cock was still hard and it swayed with the motion of the bottle.
‘I got bored of waiting,’ she laughed, before grabbing the bottle and picking it up.

‘Again?’ she asked.
‘No, please,’ I said breathlessly.
She let go and the bottle swung down between my legs again pulling my balls. I yelped, my eyes watering and my breath ripped out of me again.
‘I told you not to say a word.’
I nodded, helplessly.

Kyle looked at me with a mischievous grin. ‘This is your own fault for sending me those videos of girls messing with guys’ balls - it gave me the idea.’
I stayed quiet.
‘Do you think you can handle another one?’
I shook my head vigorously, while she put the stall back in front of me and placed the bottle on it.

‘You’ve got a choice. In a minute, I am going to allow you to speak and you are going to beg me for one of two things. You can either beg me to pull the stall away one more time. If you do that, after the bottle has stopped swinging, I will give you a handjob and let you cum. Or, you can beg me to put the chastity cage back on you until Christmas Eve, which is three days away. There’s no guarantee I’ll unlock you then though, I might change my mind. What’s it to be?’

I hesitated, looked at the bottle and looked at Kylie. ‘Please put me back in chastity,’ I said softly.
‘I said beg me.’
‘Please Kylie. Please, please, please put me back in chastity and keep me in until Christmas Eve. Please!’
She smiled, picked up the cage and carefully wrestled it back onto my cock, with my erection now faded from the pain. Once I was caged again and the key safely squirreled away, she untied me from the wardrobe and invited me onto the bed.

‘Did you enjoy that?’ she asked.
‘Yeah,’ I told her. ‘Painful but fun.’
‘Good,’ she smiled and held me close. 

We watched a couple of movies that afternoon and got a take out. The rest of the day was fairly normal. I went down on her for a while that evening when we went to bed and gave her several shuddering orgasms and again first thing in the morning, before I headed back to the family home.

*        *        *

The next couple of days were filled with visits to extended family, walks with my parents and a trip to the pub with some friends. I also found plenty of time for myself, reading, playing music and relaxing. I was consistently horny and watching porn locked up or thinking about the fun I’d been having with Kylie had me leaking precum, which I’d got into the habit of scooping up with my finger and tasting.

Kylie was busy too, she went on a night out with friends, sending me a couple of pictures of her lowcut, short dress and seductive smile. I spent the entire time she was out with her friends leaking into my panties.

I went around Kylie’s house at about 2pm on Christmas eve, her dad had gone out with her uncles and was not due back until the morning. When I arrived, she was dressed casually in jeans and a hoody, with her hair tied back and preparing some lunch for us in the kitchen. We opened a bottle of wine, ate some food and joked around together; she told me about her night out and I told her about a couple of funny things that happened in the pub. There was a lot of laughter, while we half watched a Christmas movie, and I looked at her warmly.

‘What’s the matter girlpants?’ she said - a private nickname she had started using whenever I was being soppy.
‘Honestly?’ I asked her.
‘Yeah.’
‘I’m in love with you.’ This was the first time I had told her and she smiled and blushed slightly.
‘I’m in love with you too,’ she said and then, laughing, ‘Now, where are my presents?’

I produced three packages from my bag and handed them over to her.
‘I was only joking,’ she said.
‘I know, but it seems like a good time. Happy Christmas,’ I said, handing the first small parcel.

She unwrapped it carefully, revealing the small, flat jewellery box. She opened it, revealing the black, obsidian heart on a silver chain.
‘Oh wow! It’s beautiful.’
She turned her back to me and let me help her put it on, giving me a kiss on the cheek.

She also produced three parcels and handed me the first. I could tell it was a book from the weight and the shape. It was a special edition from my favourite author - my eyes grew wide with shock and when I opened it I saw that it was signed. ‘Whoa,’ I said. ‘This is amazing!’

I gave her the second parcel, which she opened carefully to reveal a black thong with lace trim and the word ‘mistress’ embossed on it in small metal studs. She smiled, complimented them and kissed me again. ‘I’ll wear it tonight,’ she told me.

Kylie’s second gift for me was a t-shirt of one of my favourite bands, which I was pleased with, and rolled up inside was an assortment of female underwear, thongs, g-strings, french knickers, fullbacks and booty shorts. I laughed.

‘These are nice,’ I said.
‘Yeah, much nicer than some of the ones you have. Now that you have to wear them every time we are together, I figured you’d best have some good pairs.’

I thanked her and handed her my final present, which I was a little nervous about. A few weeks ago, when I was between chastity sessions, I’d used a kit to take a mould of my penis and make a dildo from it - I thought it would be a fun and sexy gift. She carefully tore off the paper to uncover the black, fabric storage bag. The expression on her face said that she had worked out what it was. She undid the drawstring and pulled out the dildo replica of my cock. She pulled a strange look. ‘It’s a dildo,’ she chuckled. ‘A very small dildo.’

‘Um, it’s my dick,’ I told her. ‘A copy of it.’
‘Oh,’ she chuckled again. ‘I see.’
‘Don’t you like it?’ I asked her, a little hurt.
‘It’s a really nice idea and I’m sure you thought it would be sexy,’ she explained. ‘It’s just, well, I’m used to bigger.’

I was simultaneously disappointed and aroused by her comments, but with my cock currently occupying a two inch cage, I was hardly in a position to disagree.

‘My ex,’ Kylie continued, ‘was pretty big. He didn’t really know what to do with it and was too stoned most of the time, so you are definitely an improvement. Plus, you are so good with your tongue and fingers, especially when you are in that thing.’ She playfully tapped my crotch, her finger clicking on the plastic through my jeans. ‘Which is really fun, by the way.’
I nodded my understanding, feeling reassured.
‘The other thing is, well, come with me.’

She took me by the hand and led me upstairs to her room. I sat on the bed while she fished something out of her suitcase. She turned around, took two steps towards the bed and handed me a long purple vibrator.
‘This is the one I use most often,’ she explained, as I took it from her.

It was about nine or ten inches long and well over two inches at its thickest point and was quite an intimidating object.
‘It’s not even my biggest,’ she said. ‘So, the one you’ve made me, as sweet as it is, probably won’t get used much. I’ll definitely keep it though, something to remember your cock by, as we probably aren’t going to be seeing much of it, are we?’
I nodded slowly.
‘I mean, this chastity thing is good fun. It has brought out a dominant side of me and I absolutely love having you so hungry and horny and desperate to get me off all time. Don’t you?’
‘Yeah, I do.’
‘And, your cock, as lovely as it is, doesn’t do nearly as good a job as your tongue, your fingers or this,’ she took the dildo from me.
‘But I can still fuck you sometimes?’ I asked.
‘Sometimes,’ she replied. 'When you earn it.'

She placed a hand around my neck and kissed me hard. I returned the kiss and within a few minutes we had pulled each other clothes off and were passionately making out on her bed - she was naked and I was wearing nothing but the chastity cage, out of which I was already leaking precum.

She picked the dildo up from the pillow and handed it to me.
‘Let’s do an experiment,’ she said. ‘Fuck me with this.’

I positioned myself between her legs, as she lay back on the bed, and gently began working it inside her already dripping wet pussy. The tip went in easily and I worked it in and out, thrusting slowly and moving deeper and deeper each thrust. She began moaning instantly, and grew wetter and wetter with each push. I fucked her with it for a good few minutes, gradually working deeper and faster until she was taking almost all of it. She came hard, biting her lip until she couldn’t contain the noise and let out a yell. I carried on fucking her with it until she motioned for me to pull it out. She rolled over onto all fours and lowered her head, her ass pointing at me and her legs spread. I worked it into her again in a doggy position and brought her to another dripping orgasm.

‘It’s your turn,’ she said, glancing over her shoulder after she caught her breath.
I gave her a puzzled look.
‘The key is in the suitcase, in a little red pot. Unlock yourself and fuck me, quickly.’

I leapt off the bed and across the room, throbbing in my leaky cage. Sure enough, resting inside her suitcase was a small plastic pot. I opened it and took the silver key out, placing it in the lock and removing the outer part of the cage. My dick looked strange at first, a stunted semi that was going to impress nobody. I removed the strap and the ring, placing all the parts and the key onto the nearby dresser. I gave myself a few gentle strokes and began to grow fully hard.

‘Hurry up,’ Kylie demanded from the bed, lying on her stomach now.
I turned around and climbed onto the bed behind her. She rose up onto her knees and stuck her butt out into the air. I got into position and guided myself inside her gaping, wet hole.

It was an incredible feeling, wetter and more open than any pussy I’d ever felt before. It made me feel small and that turned me on more than I thought it could. I began thrusting hard and fast, Kylie groaned softly once but apart from some slightly heavy breathing was fairly quiet. I redoubled my efforts, pushing as deep as possible and hard as possible, but it was clear she could barely feel me after so much fucking with the purple monster. She felt amazing though, wet and hot and sloppy, her cunt hungrily consuming everything I had and looking for more.

She lowered her head onto the pillow and pushed herself back onto me. I gave her everything I could and she gave a few soft moans, but that was all.

‘Do you see the problem?’ she said. ‘There’s nothing wrong with your cock, I’ve just been ruined by big dicks and big toys.’

I couldn’t hold back anymore, I’d only been fucking her for a few minutes but that comment tipped me over the edge and I came hard inside her with a loud groan. She giggled and wriggled while I twitched inside her before pulling out.

‘See,’ she told me, turning around and lying on her back. ‘You’ll still get to fuck me sometimes.’
I nodded away the headrush and let out a few deep breaths.

‘The only condition is this,’ she said as she put a hand on the back of my neck and guided my face towards her soaking wet pussy. ‘You have to lick up afterwards.’ I ran my tongue over her lips and her delicate pink pussy, tasting my cum and feeling it drip out of her and onto my tongue. I scooped it into my mouth and continued licking as more emerged. I flicked my tongue over her clit a few times, listening to her gasps and moans, then back to the last few drops of cum pouring out of her, which I swallowed on her instructions.

‘Be a good boy for me,’ she whispered. ‘Stay locked up and do as I tell you - and when you’ve earnt it, you’ll get this.’

I looked up at her with a dopey smile. ‘Yes mistress,’ I said.

reddit.com
u/Afraid-Flan4278 — 1 month ago

Christmas Presents [chastity] [femdom] [humiliation] [cbt]

A continuation from my previous story.

I was free for about a week - enjoying daily masturbation over porn or webcam sessions with Kylie, until about two weeks before Christmas while we were on a video call, Kylie told me it was time to lock up again.

She watched me lock myself up and laughed when I struggled to get the cage on due to my erection. Once I had finished, she made me show her close up - she seemed to be really enjoying herself.
‘What shall I do with the key?’ I asked her.
‘Put it in an envelope, seal it up tight and post it to me,’ she said. ‘I want a picture of you putting it in the postbox. I will unlock you at Christmas.’

I followed her instructions and walked straight to the nearest postbox, snapping a picture of me pushing the envelope through the slot, which I sent to her.
‘Good boy,’ she replied. ‘Don’t get too horny over the next couple of weeks.’

She endeavoured to make it difficult for me, teasing me on cam, sending raunchy text messages and pictures and making me watch porn videos every night. After about five days it felt like I was constantly leaking precum and getting turned on at the slightest evocation, whether that was a message from Kylie, talking to an attractive woman in a low cut top at work or uni, or Nicky calling me her ‘thong twin’ when we met up to play pool - even though I showed her I was wearing red boxers that day. She was wearing red boxers too, and that made the ‘twin’ thing even worse.
‘Maybe we should message each other to make sure our underwear matches every morning,’ she joked.

I told Kylie about Nicky’s jokes the next day. She found the fact that she’d seen the thong amusing.
‘If I didn’t know she was a lesbian, I’d think you two were flirting,’ she told me.
'Does it bother you?’ I asked.
‘Not really. But I might have to punish you for it anyway - I’ll think about it.’

The twentieth was my last day of work before Christmas and it was a busy day at the coffee shop with shoppers in and out constantly. It was made worse by the fact that Kylie ordered me to wear a buttplug for as long as I could manage - which ended up being most of my shift. When I got home, I had to change my pants because I had leaked so much precum.

After work and a quick shower, I got the train back to my parents’ for Christmas, getting picked up from the station around 8pm. I had a takeaway with my family and caught up with them before heading to bed exhausted but excited about seeing Kylie the next day.

The next morning, I walked across the village to Kylie’s dad’s house and arrived just after eleven. Her Dad was at work and I walked through the rain with a spring in my step, excited that I would finally be unlocked after twelve long days.

Kylie answered the door wearing a long grey bathrobe with pink trim and immaculate make up. She smiled sweetly and invited me inside. I followed her up the stairs and into her childhood bedroom, which still had a slight teenage feel to the decor.

As soon as we were in the room, she kissed me with a fiery passion, breaking it off momentarily to speak in an enthused tone, ‘God I’ve missed you!’

She kissed me again before I could respond and grabbed me tight. I kissed her back, wrapping my arms around her and letting my horny hands wander her body through the thick material of the bathrobe.

After a long moment, she broke off the kiss and took a step backwards towards the bed. I watched her with a heady mix of lust and curiosity as she undid the bathrobe and let it fall to the floor

Underneath she wore an incredible lacey blue lingerie set that looked glorious over her pale skin, her blonde hair hanging loosely onto her shoulders and her blue eyes beaming at the stunned look on my face.
‘What do you think?’ she said, giving me a twirl.
I stammered, barely able to speak. ‘You look stunning,’ I told her.
‘And look,’ she said, ‘I’ve even got your key right here.’ She pulled at the thin chain around her neck and revealed the small key that was nestled between her breasts.

I stammered again, dazed by how the lingerie seemed to accentuate every curve and how the key hung deep in her cleavage.
She took a step towards me and put her hand onto my crotch, feeling me swelling inside the black plastic of the cage.
‘Let’s see how you’re getting on, shall we?’

She knelt down in front of me, undid my jeans and pulled them down, revealing the lacey purple panties I had chosen out for the occasion.
She glanced up at me with a smile, ‘good choice.’
I removed my hoody and t-shirt while she ran her hands over the lace and commented on the heavy spot of precum leaking through.

She hooked her fingers into the waistband of my girly knickers and slowly pulled them down and let them fall to the ground where I gently kicked them aside. I was straining something fierce inside the cage as she inspected me carefully, her hands resting gently on the side of my thighs.

Kylie’s hands gently caressed my balls, squeezing slightly before running over the hard plastic that engulfed my shaft. She looked up at me with bedroom eyes and smiled. I gasped when she kissed the cage whilst holding gently holding my balls with one hand while the other travelled up the thigh and onto my ass.

She licked the precum off of the tip before taking the cage in her mouth, sucking gently. I felt nothing but the soft squeezing of my balls and the feel of her tongue occasionally running over the gaps. I groaned with frustration and she squeezed my ass while taking the whole cage in her mouth before withdrawing it completely and turning her attention to my balls, which she kissed and sucked on gently. A huge drop of precum leaked onto her cheek, which she wiped off with a finger, which she held up for me to lick clean. I eagerly complied and she sucked me hard while I did so.

After several long minutes, she suddenly stopped, standing up and stepping away. She produced a collar from under the bed, a leather strap with a ring on the front and gestured for me to come towards her and kneel down. I did as I was bid and she put the collar around me and attached a lead.
‘Start kissing,’ she said, pointing at her feet. ‘Every inch of my body, little by little until I decide otherwise.’
I bent low and began planting light kisses on her feet. I have never had a foot fetish as such, but enjoyed the humiliation and soon the kisses became more eager and I caressed them as I let each one linger on her delicate skin.

A tug of the lead indicated it was time for me to move up and I kissed her calves and shins readily, working my way towards her knees and her creamy thighs. I eagerly kissed, licked and nibbled on the warm skin and revelled in the softness and the gently fragrance of her wet pussy hiding behind the pink lace thong. I was fiercely dripping precum onto the carpet, excited that I would soon my licking her and hoping that a good job would see me released and fucking her soon.

A tug of the lead awoke me from my fantasies as she pulled me away and stood up, turning around so that her ass was in front of my face. She didn’t speak, she just waited, so I took the initiative and started kissing her round, peachy cheeks. She passed the lead between her legs and pulled slightly, forcing me closer. I responded by kissing with more passion and putting my hands on her hips as I did so.

She slipped her panties to the floor and tugged at the lead again. I kissed her harder and she pulled my face into her ass. I eagerly used my tongue to lick her hole and listened to her gasp with delight. She pulled me harder and I licked harder and faster, playing my tongue up, down and around in random motions. I manoeuvred my hand between her legs and felt the warmth and wetness of her pussy. I pushed two fingers inside easily as she spread her legs and bent forwards, leaning on the bed. I licked her ass hungrily and fingered her quickly as she gasped and moaned her way to a staggering orgasm that caused her to slump forward onto the bed breathless for a long moment, her grip on the collar loosening and allowing me a moment’s respite.

I made as if to climb onto the bed, but she stopped me.
‘Stay there,’ she said and I waited on my knees at the foot of the bed while she grabbed some items from a bedside drawer and brought them over to me.

First was a pair of bondage cuffs chained together, which she attached to my wrists. She followed this with ankle cuffs, similar chained, which she put on me with a wicked grin.
‘Open your mouth,’ she told me.

I did as I was told and opened my mouth wide as she sat on the edge of the bed. She inserted a gag with a dildo attachment and strapped it in place behind my head. The short end was a couple of inches, the long end was six or seven and a piece of fake leather separated them like the crossguard of a sword. She did it up tight with the short end in my mouth and lay back on the bed, her feet on the floor and her legs spread.

Kylie gave the lead a tug and I manoeuvred myself towards her clumsily on all fours. She spread her pussy open with the fingers of one hand and tugged with the other. I put my cuffed hands up on the bed between her legs and pushed the dildo inside her. She gave a satisfied sigh and tugged on the lead again, pulling me deeper.

I moved my head backwards and forwards in a thrusting motion, gradually getting deeper, harder and faster until my nose was rubbing against her clit. She pulled the lead tight and I pushed backwards and forwards as much as I was able, revelling in the smell of her sweet pussy and the sound of her moans. I could feel the precum dripping from my cage, my cock straining against the unforgiving plastic, but it only drove me to faster and harder thrusts. Her moans rose in volume and then fell quieter again and she released the tension in the lead and pushed my head away gently before half sitting up on the bed.

She patted the bed with her hand and gave a gentle tug on the lead, so I climbed onto the bed, my hands and ankles still cuffed and drool falling from my gagged mouth.
‘Lay down,’ she told me.

I lay on my back, she lifted my hands above my head and climbed on top of me, facing my feet with her ass and pussy poised above me. She took the dildo in one hand and gently lowered herself onto it, her ass cheeks hitting me in the face softly. She began gently bouncing up and down on me, the dildo moving in and out of her and her cum dripping down onto me. She picked up the pace and found a rhythm she enjoyed, her ass being poked with my nose each time she lowered herself, her legs holding me in place. Eventually she gasped loudly and groaned, her wetness covering me in a sticky mess as she lifted herself off the dildo and slumped forward, her hand grabbing my throbbing caged cock forcefully.

‘Ahhh, that was good,’ she said.
I tried to speak through the gag but couldn’t.
She laughed and climbed off of me and the bed.
‘Sit up. I think it’s time for your fun.’ I climbed into a sitting position, still cuffed and gagged and let her pull me to my feet by the lead as she led me across the room and towards the built-in wardrobe opposite the bed.

She opened the double doors and guided me so that I was standing in the frame, facing out into the room. She took a hold of the chain between the handcuffs and clipped them into something above my head. She unclipped the lead and removed the gag, I gasped breathlessly once it was removed, saliva dripping down onto my chest and the floor. She cast them aside and ran her hands over my chest, thighs, ass and finally my balls and aching cock.

She produced the small key from her bra and undid the chastity cage, pulling it off softly, precum almost gushing out once the cage was off. She removed the ring and the strap and put them on the dresser before stepping back and surveying me as my cock twitched eagerly, gradually getting hard for the first time in almost two weeks.

She stepped forward and touched the tip of her finger, it throbbed violently at the slight stimulation and she giggled.
‘Better be careful,’ she said. ‘We don’t want it to go off yet, do we?’
I shook my head wordlessly and watched her as she moved around the room sexily, picking up some soft rope from her dresser and a metal water flask from beside her bed.

She returned to the wardrobe and carefully tied the rope around my cock and balls in a complex arrangement, moving slowly and pausing every time I twitched. Eventually, with my genitals tied up and about 30 centimeters of excess rope dangling between my legs, she stepped back and put a small stall just in front of me. On top of the stall she placed the water bottle, which she tied to the end of the rope.

I looked at her with desperation, shook my head and began to protest.
‘Don’t say a word,’ she told me. ‘Don’t say a word or I will pull the stall away!’
I nodded my comprehension.
‘I mean, I’m going to pull it away anyway, but if you stay quiet you’ll get a nice countdown. Are you ready?’
I shook my head.
‘Ten… nine… eight,’ she counted slowly and my eyes grew wide with fear and anticipation.
‘Seven… six… five.’
I shook my head again but it had no effect.
‘Four… three.’ She kicked the stall away and I yelped loudly at the sudden hard tug on my balls. My breath shot out of my lungs and my knees buckled slightly, my sides felt like I had a terrible stitch and the bottle swayed between my legs like a pendulum, still pulling my balls down. Somehow, my cock was still hard and it swayed with the motion of the bottle.
‘I got bored of waiting,’ she laughed, before grabbing the bottle and picking it up.

‘Again?’ she asked.
‘No, please,’ I said breathlessly.
She let go and the bottle swung down between my legs again pulling my balls. I yelped, my eyes watering and my breath ripped out of me again.
‘I told you not to say a word.’
I nodded, helplessly.

Kyle looked at me with a mischievous grin. ‘This is your own fault for sending me those videos of girls messing with guys’ balls - it gave me the idea.’
I stayed quiet.
‘Do you think you can handle another one?’
I shook my head vigorously, while she put the stall back in front of me and placed the bottle on it.

‘You’ve got a choice. In a minute, I am going to allow you to speak and you are going to beg me for one of two things. You can either beg me to pull the stall away one more time. If you do that, after the bottle has stopped swinging, I will give you a handjob and let you cum. Or, you can beg me to put the chastity cage back on you until Christmas Eve, which is three days away. There’s no guarantee I’ll unlock you then though, I might change my mind. What’s it to be?’

I hesitated, looked at the bottle and looked at Kylie. ‘Please put me back in chastity,’ I said softly.
‘I said beg me.’
‘Please Kylie. Please, please, please put me back in chastity and keep me in until Christmas Eve. Please!’
She smiled, picked up the cage and carefully wrestled it back onto my cock, with my erection now faded from the pain. Once I was caged again and the key safely squirreled away, she untied me from the wardrobe and invited me onto the bed.

‘Did you enjoy that?’ she asked.
‘Yeah,’ I told her. ‘Painful but fun.’
‘Good,’ she smiled and held me close. 

We watched a couple of movies that afternoon and got a take out. The rest of the day was fairly normal. I went down on her for a while that evening when we went to bed and gave her several shuddering orgasms and again first thing in the morning, before I headed back to the family home.

*        *        *

The next couple of days were filled with visits to extended family, walks with my parents and a trip to the pub with some friends. I also found plenty of time for myself, reading, playing music and relaxing. I was consistently horny and watching porn locked up or thinking about the fun I’d been having with Kylie had me leaking precum, which I’d got into the habit of scooping up with my finger and tasting.

Kylie was busy too, she went on a night out with friends, sending me a couple of pictures of her lowcut, short dress and seductive smile. I spent the entire time she was out with her friends leaking into my panties.

I went around Kylie’s house at about 2pm on Christmas eve, her dad had gone out with her uncles and was not due back until the morning. When I arrived, she was dressed casually in jeans and a hoody, with her hair tied back and preparing some lunch for us in the kitchen. We opened a bottle of wine, ate some food and joked around together; she told me about her night out and I told her about a couple of funny things that happened in the pub. There was a lot of laughter, while we half watched a Christmas movie, and I looked at her warmly.

‘What’s the matter girlpants?’ she said - a private nickname she had started using whenever I was being soppy.
‘Honestly?’ I asked her.
‘Yeah.’
‘I’m in love with you.’ This was the first time I had told her and she smiled and blushed slightly.
‘I’m in love with you too,’ she said and then, laughing, ‘Now, where are my presents?’

I produced three packages from my bag and handed them over to her.
‘I was only joking,’ she said.
‘I know, but it seems like a good time. Happy Christmas,’ I said, handing the first small parcel.

She unwrapped it carefully, revealing the small, flat jewellery box. She opened it, revealing the black, obsidian heart on a silver chain.
‘Oh wow! It’s beautiful.’
She turned her back to me and let me help her put it on, giving me a kiss on the cheek.

She also produced three parcels and handed me the first. I could tell it was a book from the weight and the shape. It was a special edition from my favourite author - my eyes grew wide with shock and when I opened it I saw that it was signed. ‘Whoa,’ I said. ‘This is amazing!’

I gave her the second parcel, which she opened carefully to reveal a black thong with lace trim and the word ‘mistress’ embossed on it in small metal studs. She smiled, complimented them and kissed me again. ‘I’ll wear it tonight,’ she told me.

Kylie’s second gift for me was a t-shirt of one of my favourite bands, which I was pleased with, and rolled up inside was an assortment of female underwear, thongs, g-strings, french knickers, fullbacks and booty shorts. I laughed.

‘These are nice,’ I said.
‘Yeah, much nicer than some of the ones you have. Now that you have to wear them every time we are together, I figured you’d best have some good pairs.’

I thanked her and handed her my final present, which I was a little nervous about. A few weeks ago, when I was between chastity sessions, I’d used a kit to take a mould of my penis and make a dildo from it - I thought it would be a fun and sexy gift. She carefully tore off the paper to uncover the black, fabric storage bag. The expression on her face said that she had worked out what it was. She undid the drawstring and pulled out the dildo replica of my cock. She pulled a strange look. ‘It’s a dildo,’ she chuckled. ‘A very small dildo.’

‘Um, it’s my dick,’ I told her. ‘A copy of it.’
‘Oh,’ she chuckled again. ‘I see.’
‘Don’t you like it?’ I asked her, a little hurt.
‘It’s a really nice idea and I’m sure you thought it would be sexy,’ she explained. ‘It’s just, well, I’m used to bigger.’

I was simultaneously disappointed and aroused by her comments, but with my cock currently occupying a two inch cage, I was hardly in a position to disagree.

‘My ex,’ Kylie continued, ‘was pretty big. He didn’t really know what to do with it and was too stoned most of the time, so you are definitely an improvement. Plus, you are so good with your tongue and fingers, especially when you are in that thing.’ She playfully tapped my crotch, her finger clicking on the plastic through my jeans. ‘Which is really fun, by the way.’
I nodded my understanding, feeling reassured.
‘The other thing is, well, come with me.’

She took me by the hand and led me upstairs to her room. I sat on the bed while she fished something out of her suitcase. She turned around, took two steps towards the bed and handed me a long purple vibrator.
‘This is the one I use most often,’ she explained, as I took it from her.

It was about nine or ten inches long and well over two inches at its thickest point and was quite an intimidating object.
‘It’s not even my biggest,’ she said. ‘So, the one you’ve made me, as sweet as it is, probably won’t get used much. I’ll definitely keep it though, something to remember your cock by, as we probably aren’t going to be seeing much of it, are we?’
I nodded slowly.
‘I mean, this chastity thing is good fun. It has brought out a dominant side of me and I absolutely love having you so hungry and horny and desperate to get me off all time. Don’t you?’
‘Yeah, I do.’
‘And, your cock, as lovely as it is, doesn’t do nearly as good a job as your tongue, your fingers or this,’ she took the dildo from me.
‘But I can still fuck you sometimes?’ I asked.
‘Sometimes,’ she replied. 'When you earn it.'

She placed a hand around my neck and kissed me hard. I returned the kiss and within a few minutes we had pulled each other clothes off and were passionately making out on her bed - she was naked and I was wearing nothing but the chastity cage, out of which I was already leaking precum.

She picked the dildo up from the pillow and handed it to me.
‘Let’s do an experiment,’ she said. ‘Fuck me with this.’

I positioned myself between her legs, as she lay back on the bed, and gently began working it inside her already dripping wet pussy. The tip went in easily and I worked it in and out, thrusting slowly and moving deeper and deeper each thrust. She began moaning instantly, and grew wetter and wetter with each push. I fucked her with it for a good few minutes, gradually working deeper and faster until she was taking almost all of it. She came hard, biting her lip until she couldn’t contain the noise and let out a yell. I carried on fucking her with it until she motioned for me to pull it out. She rolled over onto all fours and lowered her head, her ass pointing at me and her legs spread. I worked it into her again in a doggy position and brought her to another dripping orgasm.

‘It’s your turn,’ she said, glancing over her shoulder after she caught her breath.
I gave her a puzzled look.
‘The key is in the suitcase, in a little red pot. Unlock yourself and fuck me, quickly.’

I leapt off the bed and across the room, throbbing in my leaky cage. Sure enough, resting inside her suitcase was a small plastic pot. I opened it and took the silver key out, placing it in the lock and removing the outer part of the cage. My dick looked strange at first, a stunted semi that was going to impress nobody. I removed the strap and the ring, placing all the parts and the key onto the nearby dresser. I gave myself a few gentle strokes and began to grow fully hard.

‘Hurry up,’ Kylie demanded from the bed, lying on her stomach now.
I turned around and climbed onto the bed behind her. She rose up onto her knees and stuck her butt out into the air. I got into position and guided myself inside her gaping, wet hole.

It was an incredible feeling, wetter and more open than any pussy I’d ever felt before. It made me feel small and that turned me on more than I thought it could. I began thrusting hard and fast, Kylie groaned softly once but apart from some slightly heavy breathing was fairly quiet. I redoubled my efforts, pushing as deep as possible and hard as possible, but it was clear she could barely feel me after so much fucking with the purple monster. She felt amazing though, wet and hot and sloppy, her cunt hungrily consuming everything I had and looking for more.

She lowered her head onto the pillow and pushed herself back onto me. I gave her everything I could and she gave a few soft moans, but that was all.

‘Do you see the problem?’ she said. ‘There’s nothing wrong with your cock, I’ve just been ruined by big dicks and big toys.’

I couldn’t hold back anymore, I’d only been fucking her for a few minutes but that comment tipped me over the edge and I came hard inside her with a loud groan. She giggled and wriggled while I twitched inside her before pulling out.

‘See,’ she told me, turning around and lying on her back. ‘You’ll still get to fuck me sometimes.’
I nodded away the headrush and let out a few deep breaths.

‘The only condition is this,’ she said as she put a hand on the back of my neck and guided my face towards her soaking wet pussy. ‘You have to lick up afterwards.’ I ran my tongue over her lips and her delicate pink pussy, tasting my cum and feeling it drip out of her and onto my tongue. I scooped it into my mouth and continued licking as more emerged. I flicked my tongue over her clit a few times, listening to her gasps and moans, then back to the last few drops of cum pouring out of her, which I swallowed on her instructions.

‘Be a good boy for me,’ she whispered. ‘Stay locked up and do as I tell you - and when you’ve earnt it, you’ll get this.’

I looked up at her with a dopey smile. ‘Yes mistress,’ I said.

reddit.com
u/Afraid-Flan4278 — 1 month ago

This is what happened the last time I got to cum

I was allowed out of my chastity cage for my first orgasm in a couple of weeks - but there were a few conditions and this is what it looked like. A ruined orgasm with crushed balls.

u/Afraid-Flan4278 — 2 months ago

Earning my Release - First time in chastity with my long distance girlfriend

This story is part oy my latest collection, which is available on Kindle, and is all about the first time my long distance uni girlfriend Kylie locked me in chastity and what I had to do to get my first release. I will be posting more soon. You can view previous parts on my profile.

I was still locked in the chastity cage when Kylie left at the end of my birthday weekend. She knew I had experimented with chastity by myself and had a partner lock me up before but still felt it best to not rush headlong into it. At least, that’s what she said, but when she left, we had no plan on if we would be able to meet again before Christmas, which was little over a month away.

Fortunately, Kylie had planned things out. A few days after her visit, we were chatting on webcam one evening and she asked me to show her the new pyjamas I’d bought. I’d gone with a fluffy pink and white pair and she laughed when I modelled them for her.

‘And did you throw away your boy pyjamas?’ she asked me.
‘Yes. They went in the big bins downstairs straightaway.’
She smiled wickedly down the camera.

 ‘Are you enjoying being locked up?’
‘Yes,’ I told her. ‘But I am wondering about how I will get unlocked. I might not see you until Christmas.’
It was then that she revealed that she had hidden the key in my flat and would let me know where, if I completed three simple tasks for her.

‘What are the tasks?’ I asked.
‘Your first task,’ she explained, ‘you can probably do this tomorrow. You are going to go and buy ten more pairs of feminine pants, a nice variety of colours and styles. You have to do this in person, not online and I want a picture of you in the shop with your purchase.’
‘Okay. What is my second task?’
‘When is your next night out with friends?’ she replied.
‘Friday,’ I answered, which was two days away. ‘There is a metal night at a big club in another city and there is a big group of us going.’
‘That’s perfect for what I have in mind. You’ll go out, locked up, wearing a butt plug and some of your feminine panties. I expect you to send me three photos during the night to prove you have stuck to it.’
I nodded my agreement and understanding.
‘I will tell you your third task after you have completed the other two.’

*        *        *

The first task was simple enough and I was actually quite excited about it. I made my way into town after my morning lectures and went to a large clothing store in the shopping centre that I knew had a ‘pick and mix’ section for women’s underpants. It was a quiet afternoon and I made my way through the store to the appropriate section.

I was nervous and excited, experiencing a big thrill over such a tiny act but amplified by being locked up and the need to complete this to be closer to being unlocked. As I walked through the lingerie section, I felt sweat on my neck and brow and glanced around at the women in the area to see if they were looking at me in a strange way. Despite the fact there were no other men around, nobody seemed to pay any attention to my presence.

I perused the ‘pick and mix’ display without rushing, picking out a few interesting pairs and holding them up to check the size. Some black lace French knickers took my fancy and I even held them up to my own hips when nobody was looking to check they would fit, I picked out a cotton red thong, a slightly silky pink pair of fullbacks, a blue g-string with a heart emblem and a black thong with a picture of a cartoon cat on the front.

While I browsed, one woman passing by met my eye and raised an eyebrow slightly, but she seemed more amused than anything else and said nothing. I chuckled to myself and fought the urge to make an excuse.

There was only a small queue and three different cashiers serving, I waited patiently with the items concealed in my basket. I glanced across the servers and noticed one of them was a particularly attractive young woman with wavy blonde hair, immaculate make up, pretty features and a nice body that suited the tight black uniform well. I prayed internally that I would not be served by her.

As the queue shortened, a woman with a large basket full of shopping went to the blonde’s till and I assumed it would take so long and I would be served by someone else, with two people in front of me. One server, however, was bogged down in what looked to be a complicated return and by the time I was next the blonde woman was handing the bags to her customer. She looked over at me, smiled a lazy smile and waved me over as her customer left. I took a deep breath and could already feel myself turning pink.

I put the basket on the counter and she scooped up the panties, looked up and me and gave a slight smirk.
‘Christmas present for your girlfriend?’ she asked as she scanned them.
‘Umm, something like that,’ I stammered.
She smiled a knowing smile and took my cash without saying anything.
‘Enjoy,’ she finally added as she handed me my change and the paper bag.

I wandered back through the store, stopping to take a quick selfie whilst holding the bag, which I sent straight to Kylie along with a picture of the contents.
‘Good job,’ she replied, ‘One task down, two to go.’

*        *        *

The next day was Friday and I spent most of it at work. We had a steady flow of Christmas shoppers popping in for take away coffees all day and it kept my mind off of my chastity cage and my task for later that evening. 

I went home, ate some food, showered and got myself ready. I chose out a black thong from my collection that I knew held the chastity cage well and put them on. I inserted a medium sized silicone butt plug that I found particularly comfortable and finished getting dressed. I wore a pair of dark, ripped jeans with a black band t-shirt and leather jacket, accompanied with some chains that were the style in the rock community at the time. I checked myself in the mirror and thought I looked good. I then pulled down the jeans to take a picture for Kylie. 

‘Very good,’ she replied. 

The rock bar was lively, full of quirky people wearing dark clothes and the lights glinted off all the studs, chains and piercing on show. There were plenty of good looking women and men around, both in my friendship group and the strangers. Our group took over a booth, got some drinks and chatted and joked around for a while, waiting for the first band to come on. 

I bought a couple of drinks for Nicky, as it was her birthday. She was one of my closest friends and we laughed a lot together. She was a lesbian but I found her attractive and that evening she was dressed up exquisitely in some lace up tight leather trousers, which showed off her cute bum very well. She also wore a red and black bustier style top - which was unusual as she was generally a very casual dresser.

We stood at the bar together and swapped gossip while waiting for our drinks and then I headed to the restrooms to get a snap for Kylie. I made my way into one of the cubicles and managed to snap a picture of my panties, cage and plug and sent it over to Kylie. I waited for a minute but did not receive any reply, so headed back to the bar.

I bought a drink and joined Nicky and the others who were dancing to the first band. We joked and laughed together and when a guy from another group tried to dance with Nicky, she gestured towards me to say that I was her boyfriend - a tactic she often employed to avoid unwanted attention. To reinforce the point, she moved closer, put her arms on my shoulders and made a couple of sexy moves towards me. I smiled awkwardly and became very conscious of the cage and the plug as my sexy little friend danced at me until the guy was gone. 

Once he had gone, Nicky grinned at me, mouthed a ‘thank you’ and went back to dancing normally. As the music became more intense and we had a few more drinks, we took to moshing. I was careful not to get too involved due to not wanting to get bashed in the cage, but joined in a little. At one point, one of my male friends picked me up and span me around a few times and I struggled to not fall over after he put me back down. Nicky caught me and was laughing as she steadied me. 

She smiled and gestured to go and sit down so we left the rest of our group, bought another drink each and sat down away from the dancefloor.
‘Are you having fun?’ I asked her.
‘Yeah,’ she replied over the loud music. She looked over her shoulder towards the group for a second and then gave me a curious look. ‘Can I ask you something?’ she asked.
‘Sure.’
‘Are you wearing a thong?’
I instantly turned bright pink. ‘Did you see?’ I asked.
‘Yeah, after James span you round and I caught you, I thought I saw it,’ she chuckled slightly. ‘How come you are wearing one?’
‘It’s a sort of dare,’ I stammered, ‘From Kylie.’
‘That’s funny,’ she replied. ‘I think it’s cute, can you show me?’
I looked down and lifted my shirt, pulling my jeans down slightly to show the top of the purple and orange pair I was wearing.
Nicky laughed. ‘It’s okay, I’m wearing one too.’ She pulled her leather trousers aside to reveal the black and gold pair she had on. ‘We can be twins!’
‘You won’t tell anyone will you?’ I asked.
‘Of course not.’

We went back to dancing with the group and the rest of the night went smoothly. I snuck off to the bathroom to send another picture to Kylie and she replied to congratulate me on completing my second task. Nicky made fun of me a little, but not in a way that the others could hear or understand, and we took a ‘twins’ selfie together. 

It was a fun night, despite the embarrassment and I was pleased to have also completed Kylie’s second task and was now waiting patiently for news of the third.

 *        *        *

‘Have you finished your assignments for this term?’ Kylie text me Saturday morning.
‘Yeah, I handed the last one in on Wednesday. I don’t have anything due until the end of February.’
‘Good. That means you will have time this weekend for task number three.’

I was feeling hungover and still in bed whilst texting, hoping that the task would not involve going too far or doing too much.
‘It’s a simple one. You need to give your flat a big clean and tidy. It needs to be spotless and you are going to keep it that way so that it is perfect for whenever I visit you. Send me pictures as proof and I will tell you where the key is hidden.’

I sighed out loud - cleaning was a long way from what I wanted to do today. I hid myself under the covers for a few long moments until my phone buzzed again with another message from Kylie. ‘Do you understand?’
‘Yes,’ I replied.
‘Yes what?’
I hesitated, this was something we hadn’t done before. ‘Yes mistress.’
‘Good boy,’ she sent, followed by a smiley emoji. ‘Now get to it!’

I roused myself, took a quick shower and a cup of hot tea, put on some music and began cleaning my bedroom and bathroom. After a while it became cathartic and by teatime I had also cleaned the living half of the main room too and filled a large bin bag full of stuff I decided to throw out. I decided I would stop for the day and clean the kitchen tomorrow after work.

I was up early for work on Sunday, with my shift ending mid-afternoon. I was on my way home when I had a text from a friend asking if I wanted to go and play pool with him and others that evening.
‘I’m not sure,’ I replied, ‘I have a few things to do first, if I get done I will join you.’

I got home and set to work in the kitchen and after a couple of hours of focussed work, had everything sparkling clean. It was probably cleaner than when I moved in. I took a picture and sent it to Kylie, along with ones from the rest of my flat. I admired my handy work for a few minutes until my phone buzzed: ‘Perfect. Make sure you keep it like that. I duct taped the key to the top of the third drawer down in your dresser. You are free.’

I almost sprinted across the hall to my bedroom to unlock myself. I oozed precum as I removed the cage and cast it aside. I grew hard within seconds, lay back on my bed, took my cock in my hand and stroked without even stopping to get some porn. I steadily picked up the pace and after only a minute or two felt the first wave of pleasure shoot over my whole body - I shot cum into the air and down onto my belly and chest. I continued stroking as a second burst followed, shooting onto my belly and a third onto my thigh. A fourth and fifth spurt trickled out as I groaned loudly and sighed with relief, laying there for several long minutes covered in my own cum and sweat.

I replied to Kylie to thank her for releasing me, told her what I had done and then took a long hot shower - masturbating again under the warm water, with less urgency this time, before drying off and heading to see my friends.

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u/Afraid-Flan4278 — 2 months ago