[MF] [Long] Hottest one night stand of my life during trip to Cuba

**Background:** I was then a 22 year old male senior in college, and was in a week-long trip to Cuba with a very close friend, celebrating our upcoming graduation. We had nearly zero planned out, although we had done some research about travelling and lodging in Cuba We had no hotel reservations or specific plans on what to do and see.

**How we met:** my friend and I got out of the airport and in search of a cab to the city. To save money, we ended up sharing a van to the historical center with a Japanese couple and two girls from a different part of the country. We all chatted on the way there and had some laughs. As soon as we arrived, the Japanese couple left and we never heard of them again. The girls, my friend and I planned to meet there and explore Havana together. Before we left, I finally had them chance to get a good look at them. Stella was about my height, with C-cups, thick legs, a thin waist, and shoulder length hair. Ilana was a little shorter, with perky (braless! which already got me going, although I had nothing in my mind at the time) B-cups, and a round, bubbly ass. She definitely had a sexy look, which I can’t really describe. She looked at you like she wanted you to picture her naked. That might be just me being horny in retrospect. We left, and my friend and I went to find a place to stay and a meal to eat before we met them in the time we planned (no cellphones – you actually had to plan a time and place to meet).

We hung out together for the next four days. Although we had became good friends and had joked at the verge of intimacy many times, it didn’t seem like anything was going to happen. There was hardly any drinking involved, we were mostly seeing historical things, eating and joking around. Until their last night there, the only night we actually went out.

**The build-up:** We met at around seven for dinner. Stella had her regular clothing on: short shorts that showed her legs off well, and a loose tank top with a sports bra underneath, leaving a bit of a cleavage for our craving. Ilana probably didn’t mean to, but she impressed me with her clothing. Again she went braless, with yellow shirt on the verge of see-through, which was driving me mad. She also wore a short, loose skirt – I am absolutely crazy about short loose skirts. The thought of being so easily moved, of simple windy moment showing her off, and especially the thought of her knowing that it made her so easily seen, made me horny instantly.

We had a beer before dinner and had some drinks throughout our meal. Sometime during dinner Ilana’s leg and mine started bumping and touching. At first they were short touches, but they slowly started to last longer. By the end we were done with our meals, we weren’t bumping anymore: our legs were touching 100% of the time, even if we had to sit a little bit awkwardly for it. I started moving my leg a bit, like I was caressing her with it just slightly, but still seemingly innocently. She looked at me and smirked. I took a peek a while after and she had clear pokies. Her nipples were hard – we were close to the window, but I could tell it was not the wind that was doing that to her.

By the end we decided to seat there, down some shots and have one more drink. The conversation stirred to sex slightly, and we had a little drinking game about things we liked in bed. I found out she liked being fucked from behind with a hand shoving her head in the pillow. I’m a dom (a little bit), and found that very hot. They had a laugh about me not liking blowjobs, and Ilana joked that I probably didn’t have a good one yet because I was so inexperienced (I forgot to mention they were both 26, slightly older than us). I pretended to be pissed to go along with it.

We finally got up and went to a club the girls had heard about. We got in, bought uorselves a bottle of rum and talked a bit about how different everything was. There were people ranging all ages there, which by itself was very uncommon to us – but nice, too. It felt like an inclusive place. Also, everyone danced in a sexy way. Guys and girls, and not a grinding kind of thing, just really sexy. We got friendly with two guys (probably the coolest guys in the club, they were jacked and danced really well). They told us they were dance teachers, taught us all how to dance. We were having a good time, and eventually the girls started making out with them. My friend and I didn’t think it was a big deal and kept having fun with them.

Eventually, at around 4am, the club was closing and these guys invited us to an afterparty they were having. As my friend and I didn’t really feel safe with that and were not interested in hanging out more with them, we politely declined. The girls didn’t want to either and stuck with us. We went to somewhere that was open and would sell us beer (not really a bar, just a little window opened in a house – probably illegal now that I think of it). It was around a 15 minute walk on the seaside avenue.

Ilana and I stayed behind in our walk, talking and having fun. I was making fun of her for making out with that guy, and eventually our conversation got a sexier tone. She said he wasn’t really a good kisser, so I stopped, held her by the waist, and said “you shouldn’t let this night go wasted” or something along those lines. We immediately started kissing. I was turned on by the alcohol already, and I guess she was too – and by the other guy. I picked her up and put her on a waist-height wall next to the ocean, held her by the butt, our crotches smashed against each other, almost dry humping right there, in the middle of the street. I started caressing the inside of one of her legs with my hand, moving up slowly until I could feel the side of her underwear under her skirt. She immediately shivered, and turned me on even more. Kissing intesified, and I started fingering her very slowly (yes, it was a very awkward position for that, but somhow it was manageable), and just with he tips of my fingers. She was wet, and her labia were on fire. I wanted to get her as horny as I could in the hopes she would come home with me rather than be satisfied right there, and I was clearly succeeding.

We eventually decided it had been too long since we abandoned the two and that we should get back to them. I mentioned they were probably doing the same as we were, and for my friend’s disappointment, Ilana said “Probably not”. We met them having a beer sitting on the sidewalk, and they received us with a grin. I said they should come to our house with us, and they agreed, so we got a cab together and went there. An even larger turn on for me (pathologically cheap), taxi rides were so cheap there that even if the drivers reaps you off you won’t spend too much.

**Finally, sex:** We eventually got to the house we were staying at. We talked to the owner briefly and she arranged another room for my friend and Stella (who, I learned later, slept in separate beds and didn’t do anything). Ilana walked into the bedroom a step ahead of me, and I couldn’t get my hands off of her, so I still had one hand on her waist as I closed the door and pushed her against the wall, where we resumed our dry-humping, just now slowly taking pieces of clothes off trying never to break our hot, intense kiss.

Eventually we were kissing agaisnt the wall, I was stripped to my boxers, and she to just her pink thong that I had felt earlier. It was hot as hell in Cuba, and feeling those perky small breasts with hard nipples rub against my chest while we kissed was taking me to another level. I started kissing her neck, while holding her waist firmly with my hands and pushing her against the wall. I moved even lower and reached her chest with my mouth. Her hip movement told me she wanted her nips sucked quickly, and that just made me go even slower. I moved my hands from her waist to her ass and grabbed them strongly, pulling her against me this time, while my mouth sucked on her boobs all around her nipple, my beard and mustache rubbing against it several times just to tease her. Eventually I decided she should have what she wanted and sucked on their hard, pinching them with my lips sometimes. She could barely keep her moans, her nails scratching my back while I sucked on and bit her nipples. I picked her up and threw her onto one of the single beds in the room, with most of her legs off the bed, and started sucking on her nipples again, just to quickly go down to her stomach, while my hands caressed the insides of her thighs from the back to the front, like in a hug. I slowly moved down, and each inch I moved I felt her hip rock, as if she was trying to push her pussy into my mouth. Eventually I reached the top of her thong, and I spent quite some time there, licking and sucking from one end to the other, in that super sensitive V-shaped part of the lower stomach. I then moved to the other edges of her underwear, eventually going as low as having my cheek and beard rub against the wet spot on her underwear. Before I switched to the other side, I took a second to gently kiss the spot where her clit was and rub my lips over it. While I sucked on her inner thigh on the other side, her body language begged me to finally eat her out. So I did. I quickly pulled her panties off and looked up with a smile, to see her looking at me, craving my tongue.

I started again sucking on her lower stomach, but quickly moved to sucking on her labia, then moved up to her clit. I started off by pressing my fingers on its sides to make it stick out, already swollen and ready to be sucked. Then I licked slowly, in long movements, my tongue as soft as I could make it under that much sexual tension. Eventually I sped up and hardened my tongue, and she responded with audible moans. Thinking that Stella and my friend could overhear us if she got louder got me turned on. My cock was raging at that point, I swear I could have come with just one stroke of a hand, but eating Ilana out was my ultimate pleasure at that moment.

I put my hands under her ass and pulled it up, so she would be more exposed, and sucked on the clit in a way that it was fully inside my mouth, and then started licking much quicker. She moaned louder, almost screaming, asking me not to stop. After a couple of minutes she orgasmed strongly and asked me to fuck her immediately. I barely had time to put a condom on and was inside her. Up to that point, I was kneeling on the floor and she had her legs off the bed. As we were now fucking kind of missionary style, I had my feet on the floor for stronger impulse and so did she, so we were half laying down, half standing. Her pussy was amazingly wet and felt so tight on my dick, I could hardly keep the slow rythm I started with to tease her, and I was pounding her strongly, our moans and our crotch smashing clearly audible from the other rooms in the house. I’m usually a bit loud too, but that night I made it a point to be even louder, and that turned me on so much that I was very quickly on the point of no return, and honestly I was desperate to cum at that moment so I didnçt even try to hold it back. I just screamed, Oh my fucking god I’m going to cum, and she begged me to keep going. I came a huge load in the condom (as I hadnçt even masturbated during the whole trip) without stopping my thrusts and kept going afterwards. It was an awesome feeling for a little bit, honestly I felt so masculine because I was pleasuring this girl so much with a (almost) 100% hard cock even after cumming. Luckily to me she quickly held my lower back, pressing her nails against my skin, arched her back and moaned loudly one last time, cumming strongly while her pussy clenched on my dick (oh my god that feels amazing). I then laid on top of her, still inside, with my condom filled with cum, while we breathed strongly, with that ease of mind of someone who just came.

I love that moment, it feels so intimate, and so reassuring. It probably took us ten minutes to move. I aid by her side and we looked at each other’s eyes for a while. Maybe too cheesy and romantic for a one night stand, but it felt awesome. It had been really hot, so it didn’t take long for us to be at it again.

I can tell more about what happened later – the next morning was probably one of the hottest morning-sex sessions I have ever had – if this is entertaining to you guys. It took me a lot of work, so I wouldn’t want to do it again if there is no traction at all. Anyway, this is my first time writing about my sex life, and honestly one of the few times I have ever wrote about anything, so any feedback would be highly appreciated. English is also not my first language, so please forgive my mistakes, but also let me know about them!

I hope you had as much fun reading as I had writing, because this made me fucking horny.

Edit: notepad ruined my paragraphs

Source: reddit.com/r/gonewildstories/comments/6sohek/mf_long_hottest_one_night_stand_of_my_life_during