Sex-Filled Week, Missed Threesome

by Frank

What’s your gender? Man
How old are you? 37
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Los Angeles
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Electrical Engineer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Everything is beautiful
How many sexual partners have you had in your life (including oral sex)? 100+
How many hookup stories have you here posted before? 0

Sex-Filled Week, Missed Threesome

How long ago did this hookup happen? 10 years

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a week

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? I was in Cuba with a group of friends to celebrate the new year. We’d rented a house in the suburbs, each of us with a private bedroom and bath. The place had a swimming pool, butler, and two cooks. It was sweet. I was told it was incredibly easy to pick up girls in Cuba, and my Spanish abilities not only helped me, but also my friends. The idea was, we’d spend the week meeting girls and invite them all to our place for the climactic New Year’s party. During the course of the week, I’d picked up two girls before meeting “Ana” in a disco. She was a slim black girl with small perky breasts, an athletic build, and perfect curves. We rode back to the house on my rented scooter and had pretty conventional sex, but this story is about our next hookup.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was having the most sex I’d ever had in my life leading up to the New Year’s party. I’d slept with three women, all of them beautiful Cubanas, and had burned through all the condoms I brought from home, and then several packs from Cuba too. By the time the New Year’s party happened, all of us guys were eating dinner (lobster, of course) around the large table, each with our favorite date from the previous week. There were lots of other girls hanging around, and a few other guys too. It was weird that one of the other girls I’d slept with was there too, making eyes at me as I sat next to Ana. There’s a sort of undercurrent of “get me out of here” between the Americans/Europeans and the young Cuban girls, and I was really getting that wistful vibe from this girl, like “how can you abandon me.” But I was clear and up front with all of the girls, that all I wanted was to have a good time. Ana got that, and there was nothing strange. One of the guys at the table, an older man, brought a girl who I would say was a 10+; like one of the most beautiful girls you’d ever see, and she was wearing a sexy white and blue dress that showed off her flat stomach, perfect curvy hips and plenty of side boob. I was actually trying to make a move on her while we were dancing after dinner, but she said she came with this other dude and didn’t want to abandon him. After a while, we all retired to our rooms with our girl of the night, me with Ana.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? The second the door closed, it was obvious what we were doing. We started in the shower where we washed each other. Ana stroked my cock with her hand full of soapy bubbles while I sucked on her nipples. We dried off and moved to the bed. I licked Ana all over her body, then we moved to 69. She really got into it and her back arched while she came. Then I slid on a condom and pounded her hard in missionary. She was making so much noise, I think she was trying to let the whole house know we were fucking and she was about to come. I heard pounding in the room next to mine as well, so we weren’t the only ones.

After the first round, we talked for a while about her family, life in Cuba, life in America, my plans, her plans (obviously not together). Then she started tickling around my balls and getting me hard again. Before long, we were at it again, and she was screaming like crazy. Neither of us were really drunk. I’m not a huge drinker, and it takes away from your stamina anyhow. Again, we had a little rest before starting up on round three. This time, when I was taking her from behind, doggy, she asked me to put it in her ass. I had just a tiny bit of lube left from a small package I brought from home, so I lubed up the condom and stuck it in. My god, I’d never had anal sex like that before, nor since. She was really, really into it, moaning with pleasure, pushing and rocking hard on my cock. I said before she had an athletic build, but now she was going full Olympic gold medal level, final sprint. I came inside her ass, and when I pulled out, the condom was in pieces. What she put my dick through was beyond normal, for sure.

She freaked out a little, but I had just been tested before the trip and was clean, and I told her so. We both jumped in the shower to clean up. She was worried about getting pregnant, but she cleaned off before too much dripped towards her vagina, so I assured her she’d be okay. We both collapsed to sleep. In the middle of the night, the beautiful girl from dinner came to our room and pounded on the door. She was horny from listening to everyone screwing around and wanted to mess around with Ana and I. I looked back at Ana on the bed who said “no” with her eyes and I was too tired and out of ammo anyway so I turned her down.

The following day, all the dudes and a few of the girls were just relaxing. Ana had gone home and after a while, it was just me, and one of the guys, from Venezuela. Funny how the rest of us were interested in picking up Cuban girls, but since he was Venezuelan, Latinas were a regular thing for him, and he’d picked up two tourists from Poland. One was pretty hot, the other, a blonde girl, was pretty, but a bit overweight. So it was just the four of us watching TV, and when he went to his room with one of the girls, the other, the blonde one, made a move on me. We kissed, and I fondled her boobs under her bra while she grabbed my cock over my pants. I don’t know, for whatever reason, I just couldn’t get into it. Again, too much sex over the prior week. That was all the two of us did. We both went back to our side of the sofa and kept watching TV. The next morning we all flew out, me to Mexico, but that’s another story.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I’d never had such a sex-filled week before, or after, although I’ve come close. It was a missed chance to have a threesome with an incredible woman, but I guess I did the right thing, since there was no time to negotiate with the other participant, and my body wouldn’t have responded the way I would have wanted it to anyhow. Ana sent me a few letters, one of which my eventual wife received and read, and I had some explaining to do, but since it was all before we were married, we laughed it off.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Making new friends, Everyone else was/is doing it

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I’ve told a few friends and my wife. It’s a crazy experience. Everybody should enjoy as much safe, consensual sex as they can without judgment.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? It was an entire week of nonstop sex with beautiful women, to the point where my body literally ran out of gas for more sex. I found my sexual limits. It’s like if you own a sports car, you’re always wondering how fast it will go, and if you don’t try you’ll always be frustrated. Well, I maxed out my body.

What was the WORST thing about this hookup? There was a tinge of exploitation with at least one of the women hoping that she could parlay our hookup into a relationship that would get her out of Cuba. Although I didn’t realize that until after the fact.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. It’s great knowing just how much my body was capable of, and not capable of. Cuban women are very open sexually, very enthusiastic, and the way they move is incredible. I enjoyed having sex with women of a different race (black). I was happy that I was capable of having sex without emotional attachment, although I think that was easier for me than for the women. But I’m sure they’ve all moved on with their lives.

All things considered, how POSITIVE was this experience? Fairly positive

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? If I’m ever single again, I’m going back to Cuba.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Sex is a normal human function and shouldn’t be fetishized or demonized the way it is. Take proper precautions, get proper consent without coercement, and go at it as much as possible. And if you don’t want to, that’s fine too.

What do you think about the Casual Sex Project? It’s cool. I enjoy reading other people’s stories.

You have a hookup story to share? Submit it here!