What’s your gender? Man
How old are you? 33
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? Toronto
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Tech
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? I think about sex often and I am sexually open to new experiences.
How many sexual partners have you had in your life (including oral sex)? about 75
How many hookup stories have you here posted before? two

Sex-Fueled Bareboating

How long ago did this hookup happen? last July

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Group sex

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 have known my swinging partner Teri for about 6 months in a casual sexual relationship. Teri was 38, 165 cm (5 foot 5 inches), and an avid runner. She was slim, extremely fit, and toned. Teri and I just experienced our first swap together, in the story “MILF curious about swinging” and we were hungry for more.

Shortly after that, we met “Dean” and “Karen”. Dean was 48 years old, 180 cm (5 foot 11 inches), with an athletic build. His wife Karen was 46 years old, 170 cm (5 foot 7 inches) with a very fit body and long shapely legs. They said their fantasy was to rent a sailboat with two other couples and enjoy ourselves in privacy with no one to judge us. They sounded so exciting. Teri and I would definitely fuck them! Fortunately, they chose to get back to us too. We met them at their place. We got along fabulously and had sex with each other. The sex was highly erotic and fulfilling, which “pre-qualified” us for this sailing adventure.

They told us they had already found another married couple, “Trent” and “Christine.” Trent was 35 years old, 175 cm (5 foot 9 inches) and muscular. Christine was 34 years old, 168 cm (5 foot 6 inches) with perfectly shaped fake tits and a slim athletic body. They let Teri and I meet Trent and Christine to determine compatibility. Teri and I met Trent and Christine for dinner. Christine showed up in a little black dress and heels. Teri wore her jacket, miniskirt, and heels, while both us men wore suits. We were all turned on! We decided to swap partners that night, with me taking Christine home and Trent taking Teri home. Sex with Christine was just as passionate and physically intense as having sex with Teri. When Teri and I got back together the next morning, we shared our sexual experiences from the night before, which aroused us so much that we fucked each other.

Having established compatibility, we all met up at Dean and Karen’s place one more time to plan the vacation. The planning itself was so exciting that we had group sex well into the next morning. Altogether Teri and I fucked these two couples once, and then we all had group sex. We all wanted more, but we purposely kept it at that to save the rest for the vacation.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The preparation and anticipation were driving us all crazy with lust. We all got STD testing so that we could have bareback sex and fuck to the extreme with no worries. We all got shaved around our genitals. Teri and I watched plenty of porn to learn different positions and techniques. Teri and I having practice sex was mind-blowing in itself. Even the packing was arousing, as we packed mostly swim trunks, bikinis, sex toys, and some shorts and light outerwear into carry-on backpacks. It was exciting to go through the airport with just carry-on for a sex vacation.

Dean was a certified sailor. We rented a 3 cabin sailboat in the Greek islands for one week that Dean could pilot. When boats are rented like this without a skipper, it is called bareboating. We called it bareback bareboating! The sailboat seemed small for a week-long orgy. However, we also felt that a more confined space would force six sweaty bodies to constantly bump up against each other to make for an extremely sexy experience. Indeed, this proved to be every bit true!

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? As soon as we boarded the boat, the women stripped to their bikinis and the men to their swim trunks. Once we were underway, we all sat in the cockpit, kissing and stroking each other, which led to fondling and groping. We anchored in a sheltered beach. There were a few other boats around us, but far enough away for privacy. By then, the foreplay had escalated. We were pouring white wine on each other and licking it off, we were feeding each other lunch, and then we partnered up and headed down into the cabins to have sex. We swapped partners back and forth for the rest of the day, breaking only for dinner. While we were sleeping in the middle of the night, the sound of intercourse from one couple would wake the rest of us up, make us horny, and then all three couples would be screwing again. Hearing the sound of couples having sex was also the most arousing way to wake up each morning.

The second day, we also had sex outside on the boat. A couple can fuck doggy style in the cockpit as the woman bends over and holds the railing for support. A couple can also fuck on the front deck with the woman lying on the deck spread eagle face up or face down and her partner lays on top to fuck missionary or doggy style. These weren’t comfortable positions, but we did it for the novelty and for the exhibitionists in us, not knowing if some other boats may be spying on us with binoculars.

By the third day, the constant sex was making all of us insatiable. We had not showered yet. Rather than sounding disgusting, this fueled our lust. The layers of dried cum and dried sweat on everyone’s hard, toned bodies made us feel sticky and the heat made us sweaty. Every time we swapped sex-soaked bodies, a new well-fucked partner was a feast for the senses! The sweet and pungent smell from three days of sex juices was a strong aphrodisiac. The slippery and sticky bodies begged to be touched, fondled, embraced, and licked. The salty taste was delightful. The sight of hard glistening bodies and disheveled hair was arousing. The sex talk, the dirty talk, and the moaning was unforgettable. Taking this all in made my erections harder, stronger, and more sustained. I and all three of my partners loved this foreplay, holding back until I was so hard, that my eventual penetration was a climactic relief in itself, before the start of a new round of fucking. As we fucked each other multiple times in different ways, we found favorite positions and positions where we could fuck longer and harder.

With Christine, we enjoyed a sitting scissors position where our legs wrapped around each other’s legs and waists, pulling our genitals tight together, penis in vagina. We held each other’s arms to pull us closer together. It was a very athletic performance. We were dripping with sweat, but it was ecstasy. In one session, we did this for almost two hours straight before our other partners begged to have their turn to swap.

With Karen, she liked to lie back in one of the small cabins with the low ceiling. She spread her legs and raised them up, planting her feet flat up against the low ceiling. She used this to position to raise her vagina up so that I could penetrate deep into her in a missionary position. Her body was braced tightly against the ceiling and bed, allowing me to pound forcefully, powerfully, and deep into her. Each thrust brought a loud moan or scream. It was so pleasurable that it was hard to fuck long, but with practice (and this was the only time I took viagra), this was a position we enjoyed many times for a satisfyingly long fucking.

With Teri during the day, she would ride me hard, but at night, we would lie motionless in missionary position, her legs raised and wrapped against the sides of my waist, and we would look each other in the eyes talking about the sex we enjoyed during the day. It was arousing enough to sustain my erection or we would rock and breath in tantric unision to stay coupled. Then I would thrust into her to bring her to orgasm before I shot my load into her.

On the fourth day, all three women wanted and received double penetration. It was a first for Teri and Christine. It was satisfying for everyone. Then I came up with a wild idea. Dean’s wife, Karen, would lie on her back and I would fuck her vagina. Then I would let Dean fuck my ass! Teri would sit on Karen’s face to allow Karen to lick Teri’s vagina. I had a mind blowing, eye popping fuck and orgasm. After that, we let Dean and Karen return the favour to Teri and me: I would fuck Dean’s ass, he would fuck Teri’s vagina, and Teri would lick Karen’s vagina, tasting Karen’s and my sex juices. Trent and Christine were so aroused that they also participated in a round of this with me and Teri.

After that, the remaining three days just got more uninhibited. The cabin smelled of sex by the end of the week and we spent half a day cleaning before returning the boat.

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? When we returned home, Teri had to take care of her kids for the next three weeks. She wanted to decompress and process what happened. I did too. I kept replaying in my mind everything that happened. On the one hand, it was addictive and it made me want more. More sex with more partners was all I could think of. On the other hand, there was a lonely recovery like after a high wears off. I also felt slutty. I can’t undo what happened. I always dreamed of a “normal” relationship, marriage and children, but it seems romantic dating is very hard and rare in Toronto. At least with these swingers, we enjoy each other, we were respectful to each other, we were sexually attracted to each other, and we gave each other a huge amount of carnal pleasure. With that, I was game for another sex vacation.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Birth control pill / patch / ring / injection / implant, IUD (Intrauterine device), Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, Making new friends

How intoxicated were you? Not at all (no alcohol or drugs)

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? We told a few other swingers about this, without naming names. We wanted to find partners for the next vacation. Reactions were uniformly positive and went from awe to envy.

How would you best summarize people’s reactions about this hookup? Relatively positive

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

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 super enjoyable, pure lust and hedonism. It was the best pure sex I ever had.

What was the WORST thing about this hookup? It was expensive but well worth it. I still feel a little slutty or guilty, but this hans’t stopped me nor any of us from wanting to do this again.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It changed the baseline of my experience. I don’t know if this has pushed me further out in my sexual addiction or willingness to push my sexual limits…where my partners enjoy it too of course!

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

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

Anything else you want to add about this hookup? We are doing this again in a few weeks. Trent and Christine can’t make it, but we have a new couple that expands the range of race and gender in the group. This will be exciting.

What do you think about the Casual Sex Project? I love this project!

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