u/Tattie-Anna

So... I’ve had this dream about being feminised for such a long time, and I follow so many groups and subs on Reddit and Tumblr that I think I had become addicted.
There was this girl who was posting on Tumblr a lot, and I really liked her vibe, the things she was posting and she seemed really nice.
Anyway, I commented on a few of her posts and after a couple of weeks, she sent me a message. It was clear from my profile and the stuff that I was sharing that I was a closet sissy. This seemed to turn her on, and she started to ask me lots of questions. I basically told her that I was totally closeted, no one knew, but I had this yearning to be feminised by a woman and then treated like a sissy maid and whored out at a party.
After a short while and lots of messaging, she convinced me to buy some toys, clothes, a wig, and a cock cage. Doing this felt so naughty, but liberating at the same time. It’s who I wanted to be, and I was taking the first step to becoming my alter ego, Justyna.
The delivery came, and I was so excited to get dressed up. I set aside the whole weekend to have some "me time," and it was amazing. The stuff I’d bought meant I could mix and match to create about five different outfits.
I put them all on one by one, took so many photos, and saved all these looks. It just made me horny as hell.
So after I’d had a bit of fun, I started messaging again, and she asked to see some pics. I was really nervous, but we exchanged Instas. I’d created a special one for Justyna so I could be anonymous if I needed to be. At first, I covered my face with a big love heart emoji, but I got more and more into it and realised I’d sent one with my face uncovered by mistake.
I panicked, thinking, What if it’s all a scam and she outs me? My life would be ruined. Nobody knows about this side of me.
After a nervous 10 minutes thinking about what she might do with the pic, I needn’t have worried. She sent me back a pic of her with proof that it was real and reassured me that I shouldn't worry, as I had her pics now, too. From then on, I got braver and braver, sending all my pics with my face uncovered. We got to chatting more and more, and it was just so natural.
Over time, though, the dynamic was definitely changing. From being friends who chatted, it was turning into a Dom/sub dynamic. She started to give me tasks and would make me punish myself if I didn’t complete them correctly or in time.
I had bought a case for my cock cage key that she could access remotely, meaning only she could open it. I would end up in my cage for weeks at a time with no release. This was so intense, and with the new butt plugs I’d bought, I was permanently horny. But I came to realise this is how she wanted me.
Finally, after about four months, we shared our locations and found out we were about three hours apart. This was sort of exciting, as we could have been in completely different countries.
It was then that stuff started to get really real. She asked if she could take me to a Dom/sub night at a sex club she knew and have me there as her sissy maid.
This made me really nervous, and I said we needed to meet first. I couldn’t do that the first time we met. Secretly, I was in, but I just needed some courage first.
We agreed to meet somewhere about midway between us the next weekend and stay the night in a hotel. I was to bring a couple of outfits and all my toys and clothing etc.
The day came, I collected my things and drove to the hotel. I had instructions to ready myself for her arrival. She gave me two hours to get ready before she arrived and was very specific about the outfit she wanted me to wear, a pink frilly maid outfit and my long red wig. I had frilly pop socks to wear over a pair of 4-inch strapless heels. When I was ready, I was to sit on the edge of the bed awaiting her.
Time was ticking so slowly until she finally arrived, exactly on time. I heard the key card open the door, and my stomach just dropped with total and utter fear of what the hell I was doing. It was too late now; she was here, and there was no turning back. She walked around the corner of the corridor of the room to me sitting there on the bed, just as I had been instructed. She looked me up and down and squealed with delight. She came up to me, kissed me on my forehead, and said, "Good girl."
She undid her long black trench coat to reveal herself in what can only be described as the mother of all outfits. She was wearing long black stockings with a black basque lifting up her ample bosom, set off with 6-inch black patent heels. She also had on long black gloves. She looked so sexual and so in charge .
She had already arranged for room service, as a knock on the door came moments later. She shouted to the door, "It’s open. Come on in."
I didn’t know where to look. I just sat there and froze as the waiter came into the room, looked at me, and set the food down for us. She gave him a piece of paper, a tip, winked at him, patted him on his bum, and sent him on his way. She was so in control. It was hot as hell.
We sat at the table and ate our food while she just kept looking me up and down, smiling with a mischievous grin.
Now it was time for whatever she had planned, which was all about putting me at ease. We just chatted, and she said I needed my makeup done. As I’d never worn makeup before, having her help me finish my look was exhilarating.
She took her time and made me look more feminine than I ever imagined. I almost didn’t recognise myself. I was amazed by her talent. I was hers 100%. She could do with me what she pleased. But I was not prepared for what she planned next.
She put on a little black dress and told me we were going to the downstairs bar in the hotel, assuring me that if I trusted her, no harm would come to me. I was so nervous; this was so far outside my comfort zone and far beyond anything I had imagined. But I had given myself to her in my mind and heart, so I trusted her.
We went downstairs and sat in a corner booth, where she ordered some drinks. It was the weekend, and there were some businessmen having a meal and drinks nearby. One sent over some drinks to us and asked if he could join. To my sheer horror, she said yes, and I had to pretend to be a real girl until she told him that I was a special girl with special attributes and talents. He asked questions, to which she replied that if he really wanted to know, he could come to our room to find out. She then asked for a bottle of champagne to be sent to our room, and we all left together.
My head was spinning. I didn’t know what was next, what was happening, whether this had been planned, or if I had been set up. What was I expected to do? It wouldn't be long before I found out.
We got back to the room and started to drink the champagne. I’m only petite, and having had 5 or 6 drinks, it all went straight to my head. I was dizzy and just so pliable. Mistress. as I was now told to call her, instructed me to sit on the floor next to her, at the feet of the gentleman who was now in our room.
I was told to undo his fly and put my hand in his pants. I didn’t know what I was doing, but I did as I was told, I was too far gone to resist. I reached in and fumbled around until I had it all in my hand. His head went back, and he let out a moan of sheer joy as if he was going to cum on the spot.
He undid the rest of his trousers and dropped them to the floor. He was now standing in front of me, his cock out and in my hand only inches from my face.
Mistress then instructed me to do what came naturally. So I massaged his cock and caressed his balls. He held my head and pulled my face to within millimetres of his cock. I was then instructed to kiss it, which I did. Then lick it, which I did. Then lick it some more, which I did. Then finally take as much as I could in my mouth, which I did.
Up to this point, I had considered myself straight, as I had only ever been with girls. But with a guy's cock in my mouth and his balls in my hand, I was quickly reassessing my situation. Mistress kept guiding my head back and forth on his cock until I’d taken almost all 7 inches in my mouth. Not bad for a first try, if I do say so myself.
Mistress then instructed me to carry on while she excused herself to the bathroom. Five minutes later, she returned in her sexy outfit again, only this time she had a strap-on cock around her waist and labia. It was a beautiful black rubber cock like the ones I had only ever seen in porn movies. Things were about to get serious, as I knew what that meant. We had talked about me being pegged many times, but I had never really thought it would happen.
The guy lay on the bed naked, and I was positioned on all fours in front of him, ass up and head down, sucking his cock deeply. Mistress pulled out my butt plug and lubed up my ass good and proper. She first slid a couple of fingers in, which went in too easily, I guess the plug had gaped me a little over the night.
She told me to relax and take a deep breath, saying this would hurt me a lot more than it would hurt her. I couldn’t respond as my mouth was full of cock. I grunted, and she took that to mean I was ready. She pushed the tip in and then the rest. My ass pussy was so wet with lube that it slid in so easily. She held it there for a few moments to get me used to it, then started grinding and pumping away. It was slow and steady to start, forcing me down on his cock further and further. I was now taking all 7 inches; I couldn't stop myself even if I tried, as I was pushed further and further onto him. I was actually being spit-roasted. This was way beyond anything I had imagined for tonight. I was dizzy from the alcohol, the excitement of the moment, and just the cocks in my ass and mouth. This went on for quite a while until the guy was about to cum, and I was made to get on my knees and suck the whole load out of his cock. If I dropped any, I was to be punished. Luckily, I took it all. I had tasted my own once before, but this was different. It tasted musty and smoky, but it was amazing, and I wanted more. We broke for a little while, and he got dressed and left. It was quite a first experience, and one I thought I’d love to have again.
At this point, there was a knock at the door and the shout of "Room service!"
I thought to myself, When did Mistress order room service? But I was in too much euphoria, so I just lay there and closed my eyes, hoping there was some more wine.
I opened my eyes to two male waiters and one female waiter in the room, looking at me. I didn’t know what to say.
All I got from my Mistress was, "Here you go. Three more for you to take care of. And if you do a good job, there will be a lot more where that came from." I saw them all hand her £50 each, and I was to be theirs for the whole night, passed around like a piece of meat to be used until they were finished with me. First, the girl used Mistress’ strap-on while both guys filled my mouth and hands. I had two real cocks in my face and a rubber one in my ass. But that was about to change real quick. I saw one guy putting on a condom and wondered why, I didn't want to suck a condom. Then I realised: he went over to where the female waiter was, put his cock against my pussy, and pushed inside. I was now actually being fucked properly by a real dick. It felt so different from the rubber cock and so, so much better. I said I wanted to feel it for real and told him to take off the condom. I was so drunk and horny now that they could have done anything to me, and they did. I was fucked sideways, upside down, ass to mouth, two cocks in my hand, pussy in my mouth, every position you can imagine for what seemed like forever. And it was all amazing. You name it, we did it, and I was at the centre of it all.
I’d totally lost track of what Mistress was doing this whole time, as I was just so in the moment. When I came to a little later after a nap and after they had all left, I found that Mistress had been filming so much of our foursome, with me covered in pussy juices and cummed on and in multiple times, doing my best to swallow every drop. All my makeup was smeared, and I looked like a total cum dump at this point. I just rolled over and went to sleep in her arms, cuddling until I woke up the next morning to the news that she had booked another night for us in the hotel. She said she had bigger and better plans for me tonight.
To which I just asked, "Which outfit should I wear?" and we went down for breakfast.

So... I’ve had this dream about being feminised for such a long time, and I follow so many groups and subs on Reddit and Tumblr that I think I had become addicted.
There was this girl who was posting on Tumblr a lot, and I really liked her vibe, the things she was posting and she seemed really nice.
Anyway, I commented on a few of her posts and after a couple of weeks, she sent me a message. It was clear from my profile and the stuff that I was sharing that I was a closet sissy. This seemed to turn her on, and she started to ask me lots of questions. I basically told her that I was totally closeted, no one knew, but I had this yearning to be feminised by a woman and then treated like a sissy maid and whored out at a party.
After a short while and lots of messaging, she convinced me to buy some toys, clothes, a wig, and a cock cage. Doing this felt so naughty, but liberating at the same time. It’s who I wanted to be, and I was taking the first step to becoming my alter ego, Justyna.
The delivery came, and I was so excited to get dressed up. I set aside the whole weekend to have some "me time," and it was amazing. The stuff I’d bought meant I could mix and match to create about five different outfits.
I put them all on one by one, took so many photos, and saved all these looks. It just made me horny as hell.
So after I’d had a bit of fun, I started messaging again, and she asked to see some pics. I was really nervous, but we exchanged Instas. I’d created a special one for Justyna so I could be anonymous if I needed to be. At first, I covered my face with a big love heart emoji, but I got more and more into it and realised I’d sent one with my face uncovered by mistake.
I panicked, thinking, What if it’s all a scam and she outs me? My life would be ruined. Nobody knows about this side of me.
After a nervous 10 minutes thinking about what she might do with the pic, I needn’t have worried. She sent me back a pic of her with proof that it was real and reassured me that I shouldn't worry, as I had her pics now, too. From then on, I got braver and braver, sending all my pics with my face uncovered. We got to chatting more and more, and it was just so natural.
Over time, though, the dynamic was definitely changing. From being friends who chatted, it was turning into a Dom/sub dynamic. She started to give me tasks and would make me punish myself if I didn’t complete them correctly or in time.
I had bought a case for my cock cage key that she could access remotely, meaning only she could open it. I would end up in my cage for weeks at a time with no release. This was so intense, and with the new butt plugs I’d bought, I was permanently horny. But I came to realise this is how she wanted me.
Finally, after about four months, we shared our locations and found out we were about three hours apart. This was sort of exciting, as we could have been in completely different countries.
It was then that stuff started to get really real. She asked if she could take me to a Dom/sub night at a sex club she knew and have me there as her sissy maid.
This made me really nervous, and I said we needed to meet first. I couldn’t do that the first time we met. Secretly, I was in, but I just needed some courage first.
We agreed to meet somewhere about midway between us the next weekend and stay the night in a hotel. I was to bring a couple of outfits and all my toys and clothing etc.
The day came, I collected my things and drove to the hotel. I had instructions to ready myself for her arrival. She gave me two hours to get ready before she arrived and was very specific about the outfit she wanted me to wear, a pink frilly maid outfit and my long red wig. I had frilly pop socks to wear over a pair of 4-inch strapless heels. When I was ready, I was to sit on the edge of the bed awaiting her.
Time was ticking so slowly until she finally arrived, exactly on time. I heard the key card open the door, and my stomach just dropped with total and utter fear of what the hell I was doing. It was too late now; she was here, and there was no turning back. She walked around the corner of the corridor of the room to me sitting there on the bed, just as I had been instructed. She looked me up and down and squealed with delight. She came up to me, kissed me on my forehead, and said, "Good girl."
She undid her long black trench coat to reveal herself in what can only be described as the mother of all outfits. She was wearing long black stockings with a black basque lifting up her ample bosom, set off with 6-inch black patent heels. She also had on long black gloves. She looked so sexual and so in charge .
She had already arranged for room service, as a knock on the door came moments later. She shouted to the door, "It’s open. Come on in."
I didn’t know where to look. I just sat there and froze as the waiter came into the room, looked at me, and set the food down for us. She gave him a piece of paper, a tip, winked at him, patted him on his bum, and sent him on his way. She was so in control. It was hot as hell.
We sat at the table and ate our food while she just kept looking me up and down, smiling with a mischievous grin.
Now it was time for whatever she had planned, which was all about putting me at ease. We just chatted, and she said I needed my makeup done. As I’d never worn makeup before, having her help me finish my look was exhilarating.
She took her time and made me look more feminine than I ever imagined. I almost didn’t recognise myself. I was amazed by her talent. I was hers 100%. She could do with me what she pleased. But I was not prepared for what she planned next.
She put on a little black dress and told me we were going to the downstairs bar in the hotel, assuring me that if I trusted her, no harm would come to me. I was so nervous; this was so far outside my comfort zone and far beyond anything I had imagined. But I had given myself to her in my mind and heart, so I trusted her.
We went downstairs and sat in a corner booth, where she ordered some drinks. It was the weekend, and there were some businessmen having a meal and drinks nearby. One sent over some drinks to us and asked if he could join. To my sheer horror, she said yes, and I had to pretend to be a real girl until she told him that I was a special girl with special attributes and talents. He asked questions, to which she replied that if he really wanted to know, he could come to our room to find out. She then asked for a bottle of champagne to be sent to our room, and we all left together.
My head was spinning. I didn’t know what was next, what was happening, whether this had been planned, or if I had been set up. What was I expected to do? It wouldn't be long before I found out.
We got back to the room and started to drink the champagne. I’m only petite, and having had 5 or 6 drinks, it all went straight to my head. I was dizzy and just so pliable. Mistress. as I was now told to call her, instructed me to sit on the floor next to her, at the feet of the gentleman who was now in our room.
I was told to undo his fly and put my hand in his pants. I didn’t know what I was doing, but I did as I was told, I was too far gone to resist. I reached in and fumbled around until I had it all in my hand. His head went back, and he let out a moan of sheer joy as if he was going to cum on the spot.
He undid the rest of his trousers and dropped them to the floor. He was now standing in front of me, his cock out and in my hand only inches from my face.
Mistress then instructed me to do what came naturally. So I massaged his cock and caressed his balls. He held my head and pulled my face to within millimetres of his cock. I was then instructed to kiss it, which I did. Then lick it, which I did. Then lick it some more, which I did. Then finally take as much as I could in my mouth, which I did.
Up to this point, I had considered myself straight, as I had only ever been with girls. But with a guy's cock in my mouth and his balls in my hand, I was quickly reassessing my situation. Mistress kept guiding my head back and forth on his cock until I’d taken almost all 7 inches in my mouth. Not bad for a first try, if I do say so myself.
Mistress then instructed me to carry on while she excused herself to the bathroom. Five minutes later, she returned in her sexy outfit again, only this time she had a strap-on cock around her waist and labia. It was a beautiful black rubber cock like the ones I had only ever seen in porn movies. Things were about to get serious, as I knew what that meant. We had talked about me being pegged many times, but I had never really thought it would happen.
The guy lay on the bed naked, and I was positioned on all fours in front of him, ass up and head down, sucking his cock deeply. Mistress pulled out my butt plug and lubed up my ass good and proper. She first slid a couple of fingers in, which went in too easily, I guess the plug had gaped me a little over the night.
She told me to relax and take a deep breath, saying this would hurt me a lot more than it would hurt her. I couldn’t respond as my mouth was full of cock. I grunted, and she took that to mean I was ready. She pushed the tip in and then the rest. My ass pussy was so wet with lube that it slid in so easily. She held it there for a few moments to get me used to it, then started grinding and pumping away. It was slow and steady to start, forcing me down on his cock further and further. I was now taking all 7 inches; I couldn't stop myself even if I tried, as I was pushed further and further onto him. I was actually being spit-roasted. This was way beyond anything I had imagined for tonight. I was dizzy from the alcohol, the excitement of the moment, and just the cocks in my ass and mouth. This went on for quite a while until the guy was about to cum, and I was made to get on my knees and suck the whole load out of his cock. If I dropped any, I was to be punished. Luckily, I took it all. I had tasted my own once before, but this was different. It tasted musty and smoky, but it was amazing, and I wanted more. We broke for a little while, and he got dressed and left. It was quite a first experience, and one I thought I’d love to have again.
At this point, there was a knock at the door and the shout of "Room service!"
I thought to myself, When did Mistress order room service? But I was in too much euphoria, so I just lay there and closed my eyes, hoping there was some more wine.
I opened my eyes to two male waiters and one female waiter in the room, looking at me. I didn’t know what to say.
All I got from my Mistress was, "Here you go. Three more for you to take care of. And if you do a good job, there will be a lot more where that came from." I saw them all hand her £50 each, and I was to be theirs for the whole night, passed around like a piece of meat to be used until they were finished with me. First, the girl used Mistress’ strap-on while both guys filled my mouth and hands. I had two real cocks in my face and a rubber one in my ass. But that was about to change real quick. I saw one guy putting on a condom and wondered why, I didn't want to suck a condom. Then I realised: he went over to where the female waiter was, put his cock against my pussy, and pushed inside. I was now actually being fucked properly by a real dick. It felt so different from the rubber cock and so, so much better. I said I wanted to feel it for real and told him to take off the condom. I was so drunk and horny now that they could have done anything to me, and they did. I was fucked sideways, upside down, ass to mouth, two cocks in my hand, pussy in my mouth, every position you can imagine for what seemed like forever. And it was all amazing. You name it, we did it, and I was at the centre of it all.
I’d totally lost track of what Mistress was doing this whole time, as I was just so in the moment. When I came to a little later after a nap and after they had all left, I found that Mistress had been filming so much of our foursome, with me covered in pussy juices and cummed on and in multiple times, doing my best to swallow every drop. All my makeup was smeared, and I looked like a total cum dump at this point. I just rolled over and went to sleep in her arms, cuddling until I woke up the next morning to the news that she had booked another night for us in the hotel. She said she had bigger and better plans for me tonight.
To which I just asked, "Which outfit should I wear?" and we went down for breakfast.