u/Ok_Bathroom_3007

This story happened three years ago in Madrid, I was 23 at the time. Everyone in the story is 18+.

Waking up in the hostel room hot, sweaty and hungover, I reflected on the night I just had. It was patchy, most of the night I don’t remember, however one thing definitely stuck in my mind. I’d gone out with some friends I’d met in the hostel, playing drinking games in bars before heading to the club. Everyone was drunk, including myself. I walked with a girl named Carly, she was from near where I was, and we were both hitting it off.

Arriving at the club, we paid an extortionate fee for entrance, however we all agreed to do so. We got to the bar, trying to barge through to order a drink. I bought me and Carly a drink and we both headed for the dance floor. The next few hours were a blur, me and Carly had lost the others, and proceeded to do shots and double vodkas whilst the nightclub got busier and busier. Back on the dance floor, we danced like there was nobody around, she led my hand up her leg and over her panties. We kissed wildly until I said I had to go the toilet. This is where it gets interesting.

Entering the males toilet, it was much quieter than expected, the urinal was empty and only two guys stood by the sink. Unzipping my jeans, I let out my half erect dick. As I was about to start, a guy came and stood right by me, unbuckling his belt. The urinal was long, long enough to not have to stand shoulder to shoulder. Turning my head, I was met with the eyes of the other guy. He was feminine looking, if you had to describe a generic twink from a porno, it would be him. He had a brown curly hair, short on the sides, brown eyes, big lips and skinny.

‘Hey’ he whispered to me.

I nodded back to him, unsure where he was actually from. He pulled out his dick right next to mine, I couldn’t help but look at it as he looked at me. He moved closer, our hips now touching. He brought his lips towards my ear, softly biting the lobe, instantly making me softly moan. As soon as I moaned, he knew I wanted what he was going to give me. With nobody in the bathroom, he nodded his head over to one of the cubicles. Hesitantly, I made my way to it, and as soon as we locked the door behind us, a few guys entered, loud and drunk. There was the slightest of gaps under the door, I hoped it was small enough that nobody could see two sets of feet under them. With both of our cocks out touching each others, we waited for the guys to leave.

After a few minutes, they did, and we began to kiss immediately. We jerked each other’s dicks, mine was already wet with pre cum from dancing with Carly. We moaned in each other’s mouths, desperately trying to stay quiet just in case somebody was in the bathroom. Grabbing his curly hair, I pushed his down, his mouth taking to my tip immediately. The more he sucked, the harder it became to stay quiet, my hand over my mouth to muffle the sounds. My grip on his hair became tighter and tighter until I was ready to blow. I tapped on his head, giving him the signal I was ready. As I exploded down his throat, he sucked even harder, trying to get every last drop from me. He pulled my jeans back up, and gave me a kiss before checking if the coast was clear for him to leave. I stayed in the cubicle, noticing he had came all over the floor, unsure if it was before or after I came.

As I waited to leave, I checked my phone to find a few messages off Carly asking where I was, it had only been 10 minutes so I could easily find an excuse. I walked down back to the dance floor to meet her, shocked at what had just occurred. We soon left after that, going back to her hostel bed, kissing and doing some foreplay, the thought of the twink making me harder. After finishing, I want back to my room and slept, waking up hot, sweaty and hungover.

So on my last post, I mentioned that during my time in Thailand, I also hooked up with a 50 year old ladyboy. Some people messaged asking for the story, so here it goes.

After a boozey 4 weeks across the party islands in south Thailand, I decided to head east. I arrived on a smaller island, much more chilled than the others, planning on a break from the drink, sex and partying. Going with the flow, I didn’t book anywhere to stay, and after two hostels told me they were fully booked for the week, I headed to a guest house on the beach. This is where I met Noi, a 50 year old woman who rented out a room in her small house.

After speaking with her, we agreed a price for the week, considerably cheaper than where I’d recently been staying. She quickly showed me around the place before showing me my room, surprisingly nice, especially for the price. It was late so we said good night as I headed for a shower and then bed.

Waking up late, clearly needing to catch up on sleep, I made my way to the kitchen. Noi wasn’t around, so I helped myself to coffee and bread, taking it out to beach. Still half asleep, I had my breakfast out in the sun, looking out at the waves in the distance. It wasn’t long until Noi came back, carrying two shopping bags. It was the first time I’d fully checked her out, she was small, a little bit curvy, short jet black hair, with piercings in both ears. She was wearing sunglasses and a sundress, showing off her great figure. It was impossible to believe she was 50, looking 35 at the most. Topless and in my swimming shorts I greeted her, helping her with the shopping.

In the kitchen we talked for hours, she’d told me about her life, that her ex husband moved back to Bangkok years ago. Although she was comfortable telling me, I decided not to ask any more questions about him. I told her all about my travels, and all the places I’d been to in Thailand. I’d explained that I wanted a chilled week, she told me I’d come to the right place for that. The more we chatted, the more comfortable we were with eachtother, even having conversations about my ex relationships. She asked if I wanted to anything the next day, and that she could take me round the island on her moped, which I agreed to.

The next day came, Noi woke me up, saying she’d made breakfast. After eating together, I climbed on the back of her moped, my arms around her, holding on for my life as she sped around. 15 minutes passed before she parked up on the side of the road, she led me through some trees. Quickly soil became sand, a small cove hidden on the island. It was like we had our own private beach, she lay down the towels as I headed into the water. It was bliss, it was the first time I’d heard nothing in a long time. Noi joined me in there, both treading water as we talked. My eyes were glued to hers, her dark wet hair made her brown eyes shine even more. We both couldn’t help but smile at each other, each sentence flirtier than the last. I held myself back from kissing her, worried I was reading it all wrong.

We both swam back to shore, lying on the towels on the hot sand. Only a foot or two separated us. Being English, I had to rub suncream on myself, managing to reach most parts of my body. As I tried to reach my back, Noi sat up and helped. It had gone exactly as I’d hoped. I lay on my front as she rubbed suncream into my back, both of us silent as she did so. She complimented my physique, which had deteriorated greatly during my travels. I turned back around, Noi stayed kneeled up next to me. I told her I found her very attractive, refusing to believe her age. A nervous smile broke, unable to look at me as I complimented her back. My hand went to hold hers, hoping to get her eyes back on me, which they did. I sat up, smiling at her, glancing from her eyes down to her lips, wanting to her to make the first move. The tension was too much for us both, our lips touching, and then passionately kissing eachtoher.

We kissed for a while on the beach before she said we should head back. As I climbed back on her moped, I held onto her in a different way, my hands exploring her body. Her tits were perky and solid, clearly fake, and from past experiences I knew what that could mean. It was something I’d already questioned when we were in the water, if she was a ladyboy or a woman, neither bothered me. Half tempted to find out straight away, I resisted the temptation to feel, waiting to get back instead.

Arriving at the house, I asked her if she wanted to go out for some drinks and food. She told me she knew some great spots and would be ready in an hour. I showered and got changed, waiting in my room for Noi. She knocked on my door, I walked over to open it and there she stood, looking amazing. She wore a green dress, her hair tied back with light make up on her face. I, on the other hand, was underdressed, not having anything in my bag to even come close to what she was wearing. We walked to the first bar, the whole time I checked her out, fully attracted to what I was seeing.

A few drinks had passed, we sat out a beach bar together, both a little bit tipsy and fully comfortable with each other. The conversation flowed nicely, with some leg touching under the table. I was eager to get back to the house, wanting to carry on from where left it at the beach. It turned out we didn’t need to go back to house, because after a few more drinks were kissing each other at the bar, her hand making her way up my shorts. She brushed over my erect dick, smiling, happy from what she had felt. Still at the bar, she kissed my neck and whispered in my ear that she wanted to go back.

We only made it to the kitchen at her house before we were all over each other again, picking her up with her legs wrapped around me. My mouth went down from her lips to her neck, then lower to her breasts. She moved the strapping off of her shoulder so her tits were now uncovered, sucking on them as I grabbed her ass. I lay her down on the kitchen table, pulling off the dress so she was only wearing her panties. I kissed down her body before reaching her black silk panties.

Unlike other ladyboys, she didn’t warn me or tell me, just let me find out myself. If I’m being honest, I’d felt her dick when she was up on me, and it was clearly erect when I took her dress off, leaving a big crease in her panties. Immediately I took off her panties and began to suck her, she was bigger and thicker than anyone I’d been with, and she’d clearly shaved whilst she got ready beforehand. Her pre cum tasted great, her moans whilst I sucked the tip made me hornier and hornier. I tried to take her whole in my mouth but I couldn’t. Off my knees, I stood up and brought her to the edge of the table, where I took off my shorts and flopped out my fully erect penis. It was clear she’d done this many times, as I received the best blowjob that I’d ever had. We spent the rest of the night jerking and sucking each other, Noi came three times whilst she made me cum four times! I think we ended up actually sleeping at 6am, cuddled next to each other when we woke up.

We lay in bed talking, she’d asked me if I was bothered she was a ladyboy. I told her I wasn’t, and that she wasn’t the first I’d been with in Thailand. She told me it was obvious she wasn’t my first one by the way I didn’t react to her dick and the way I sucked it. The more we talked about the night before, the hornier I became, my dick hardening on her ass. She turned to me and smirked, kissing me as she stroked me, teasing my tip around her hole. She grabbed the lube from the side, putting a lot in her hand, covering my dick in it. We took our time putting it in, kissing more passionately with each inch that entered. I’ve had serious relationships before, but I’ve never had more intimate sex than what me and Noi had that morning, and for the rest of the week. It wasn’t rough and hard, it was slow, enjoying every second of it.

At the end of the week it was tough to say goodbye. She’d asked me to stay a few more days but I knew it was time for it to be over. That week with Noi was one of the best weeks I’ve had, and I haven’t been attracted to anybody as much as her since. We stopped speaking a year ago after she told me she’d started seeing a woman from the island.

When I was in Bangkok, I partied hard for a week, getting drunk every night, forgetting most things when I woke up. However on one of my last nights, something happened that I could never forget.

It was roughly 2am, I was done clubbing and wanted to head back to my hostel. Stumbling out onto khao San road, I was instantly surrounded by people. In the crowd, prostitutes grabbed me, trying to pull me towards them. Before I knew it I was on the side of the road, with three Thai women in front of me. The three of them negotiated prices in front of me, until one of them told me 400 Baht (less than £10)!

Drunkenly I nodded, and she spun around, grabbing my arm and taking me to a low quality apartment block, only 2 minutes from where we were. As she grabbed her keys from her bag to enter the block, I asked one question.

‘Are you a lady?’

She looked at me with a smirk, pulling my hand towards the crotch of her dress. I was met with a hard throbbing cock. It was something I was definitely curious about before going to Thailand, and I knew I was going to go through with it.

‘I know you like’ she said to me.

After giving her a quick kiss, we headed into the room. She lay me on the bed as she got herself ready in the bathroom. I quickly messaged my friend ‘about to fuck a ladyboy’, before putting my phone down as she came into the room. She’d taken off her summers dress, and instead was in black laced lingerie. Her tits looked great, and her whole body was soft to touch. She wasted no time, unbuckling my belt and moving down on me, my dick already erect from everything. She sucked good, not the best I’d had, but the thrill of it all made it feel amazing. Although the feeling was great, I was still curious to see what she was working with.

I pulled her hair to remove her mouth off my dick, bringing her back up to me to kiss. She straddled me as both our dicks rubbed together, with only her soft panties in between us.

‘Can I suck you?’ I asked her.

She giggled and nodded her head, the excitement in her eyes growing. She stood on the side of the bed, grabbing me by my neck and putting me on my knees. I kissed the outline of her dick through her panties until she eventually lowered them down. She was as thick as me, maybe an inch shorter, with some pubic hair above her shaft. As I opened her mouth I instantly tasted her pre cum, licking all of it up, loving each taste I got. She thrusted harder and harder until she was ready to cum, hesitant if I wanted her load.

‘I want to taste it’ I said looking up at her.

I sucked her hard and good after that, begging for her cum. Her moans were slutty and very loud until she unloaded into my mouth. It was way more than I’d anticipated, having to take my mouth off and let some go down my chest. She lay me back down, licked her cum off me and sucked me until I finished, with her also taking most of my load down her throat.

I told her after I’d finished that she was my first ladyboy, and tipped her extra for her service. After it I was desperate for more ladyboy action, actively only seeking it. The rest of my time in Thailand was filled with many more stories, even fucking a 50 year old ladyboy !

Last year I got super drunk at a beach party in South Cambodia. Whilst trying to make my way back to my hostel, I was approached by a tall, slim woman. She gave me some water and laid me down on a sun lounger in the middle of the night. I was already topless, with only swimming trunks on, no boxers underneath. She began to massage my feet, slowly moving up to my legs and then bulge. After rubbing there a while, I finally became hard, leading her to pull down my shorts.

With people still walking near by, she began to suck my dick, making my toes curl and moan loud. After a few minutes, she led me to an abandoned wooden hut, telling me she wanted me to fuck her pussy. We made out as I felt my way around her whole body, her ass nice and firm. My fingers entered the side string of her bikini bottoms, bringing it round to her wet pussy. As you can tell, I did not find what I was looking for, and brushed against a hard wet cock. She giggled in my mouth as she kept kissing me, stroking my hard dick, telling me it was okay and it was our secret. After letting her continue, she dropped her bottoms, her dick flopping onto mine, which she began to stroke against each other.

She lay back onto a wooden bench, her legs in the air, her hand pulling me in close to her. She grabbed my dick, spitting in her hand to make it wet, before teasing it over her hole. She made me beg her to put it in, and after doing so, she slipped the tip in, her hole swallowing over it. The grip she had was indescribable, instantly making me moan, loud enough for people to hear. She dictated the pace, pushing her ass over my dick until all 7 inches was going in and out of her. She grabbed my hand, placing over her dick, making me jerk her as she took control of the fucking.

After I told her I was close, she pushed me back, my dick leaving her hole. She stood up and sat me down on the bench, moving her dick in front of my face. She placed her thumb over my lips, demanding I suck it, and soon her thumb was replaced by her hard dick. She took no time abusing my throat, her whole dick going into my mouth, her pubic hair brushing against me with each thrust. Each thrust became harder until she emptied her balls down my throat, making me swallow every drop.

With her cum still in my mouth, she rode me as she shared her cum in our mouths. As soon as she begged me for her cum, I obeyed, unloading a weeks long load into her tight ass. She instantly got up, got dressed and we both left, both pretending like nothing had happened.

I hooked up with my ex’s sister about a month after she broke up with me. I’ve only told my closest friend who’s told me to not tell anyone. It only happened once but she’s asked a few times now for it to happen again. It was very fucking hot, however I felt super guilty after we did it. My ex has moved on pretty quick so I feel I can too.

Everyone in this story is 18+.

When I started university, I quickly became one of a big friend group. 12 guys and 6 girls, all with different interests, hung out together nearly every day. Most nights we’d go party out in the city or in someone’s houses. Among this group was a guy named Jo, he was openly gay, a very nice guy who knew how to party. On a night where I’d clearly had too many drinks, I’d told Jo about times I’d hooked up with guys, something he was surprised about as he thought I was completely straight. He was supportive of it and said I didn’t need to tell anyone if I didn’t want to. From then, me and Jo became very close friends.

It was around Christmas time, it was our final night before everyone headed home for the holidays. The whole group headed into the city for what can only be described as a very messy night. Near the end of the night, me and Jo shared a cigarette down an alley way next to the club. He was telling me about his boyfriend breaking up with him, not seeming too bothered about it, now saying he was single and ‘ready to fuck’ in his words. A brief pause happened after he said that, both of us looking at each other, before I laughed and said let’s head back in. More drinks later and we were in a taxi back home.

Most of us stayed in halls, whereas Jo lived with family friends. He joined the taxi back, thinking there would be an afters, however quickly realising all of us were going to bed. I told him he could sleep in my room, but had to be up early the next morning as I was leaving. We both got into my bed, which was smaller than a double, and both got under the bed sheets. I was comfortable with Jo, so both of us decided to just sleep in boxers. We said good night and I flicked off the light. Lying there in the dark, Jo’s body was close to me, he was extremely warm and fidgety. It wasn’t long until I flicked the light back on, jokingly telling him to stop moving around and questioning how warm he was.

After I flicked the light back off, we chatted a bit, eventually getting back onto the topic of me getting with guys, him asking me if I’d ever do it again. I told him I’d hooked up with a guy since being at uni but he was terrible and it had put me off guys. Jo replied, just not with words, placing his hand on my thigh.

‘What are you doing?’ I asked.

‘Shhhhh’ Jo replied. ‘Just tell me if you want me to stop’.

His hand rubbed up and down my thigh, giving me time to think what I wanted. On one hand, Jo was my friend, and I didn’t want it to ruin anything. On the other, I was drunk, horny and would take a whole lot for me to say stop. So I stayed silent. A bit more rubbing until Jo realised that I wanted it, moving his hand over my crotch, jerking me through my boxers. With my head tilted back, I let Jo go to work, pulling down my boxers, spitting in his hand and stroking me under the covers.

‘Suck it for me’ I half asked.

Jo giggled and moved down under the covers, his mouth moving down my body until his lips met my wet tip. As soon as he started to suck my dick, I knew I wasn’t going to last long, he clearly knew what he was doing. Not even 2 minutes went by before I was gripping my bed sheets and moaning as I came hard into Jo’s mouth. He stayed there for a minute, cleaning up my whole cock, before going to the bathroom to wash out his mouth. He came back into bed as if nothing had happened, and soon we both fell asleep.

Waking up both hungover and tired, we didn’t mention what had happened in the night, just casually talking about other things. Over the Christmas holidays, I messaged Jo one night, wanting to talk about what happened. We both agreed we should just stay friends but both didn’t regret it, and to not feel bad about it if it did happen again. Well to cut a long story short, the first night out we had together after Christmas ended up with him on all fours on my bed. We regularly hooked up throughout the first year of uni, and one of our girl friends even caught us!

In the summer after first year, Jo rekindled with his ex boyfriend, which they stayed together for 2 years, breaking up just before we all finished uni. On our day of graduation we finally hooked up together again, just as good as the first time. We are planning a uni reunion for this summer, with both of us single, hopefully he’s up for a good time once again.