by Mr U

What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? NYC
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? School Counselor
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
How many sexual partners have you had in your life (including oral sex)? 35
How many hookup stories have you here posted before? 0

Trying Out a NYC Sex Club

How long ago did this hookup happen? 2 years

What was your relationship status at the time? In a relationship (open)

How would you best classify this hookup? Group sex

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? This story takes place in one of NYC’s sex clubs. My partner was the one to bring up the idea, and I was the one who did the research into finding a good fit for us. Some clubs are about the BDSM scene, but we were mainly looking to ‘swap’ partners and to try out threesomes and the like.

To give you some idea of the space: In addition to several chairs and sofas near the stairway, further into the room are five beds. Four of them are connected in the shape of an L, and then there is one across from the long part of the L.

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? A few years ago, I met a woman who, like me, was interested in a FWB situation. I’ll call her Nina. Early on in our short relationship, we decided to visit a sex club, and after some research, we decided on one in lower Manhattan.

The First Visit (relatively tame): We went there on a quiet night and ended up having sex on one bed while another couple finished up on another. I didn’t reach orgasm, so after a break, we went back upstairs and had sex again, and this time, I held the breast of a woman I didn’t know while her partner fucked her. Nina and I didn’t want to have much to do with that other couple, however, because they smelled terribly of cigarettes and booze and seemed quite drunk. After we both came, we sat on one of the beds and watched a young woman having sex, doggy-style, with a guy she’d come to the club with. Another young man wanted to join them, but his date stormed out of the club, so he stayed on his own, getting a blowjob from the woman who was getting fucked. I’d never seen a ‘spit-roast’ other than in pornos, and it was much sexier in person. The drunk couple made their way over to the threesome and created a ‘fivesome’ of some sort, with the drunk woman draped over the young woman. I wanted to join, but Nina was tired, so we went home, content that we’d had a chance to experience something new though relatively mild. In hopes of some real ‘swinging’, we went back again a few weeks later.

The Second Visit (wild): When we arrived just past 12:15, there were quite a few couples on the top floor. Some people were fucking or giving or receiving oral sex; others sat nearby, watching and apparently considering whether to join. We found a comfy area to sit and enjoyed the view for over half an hour. I was raring to go, but Nina kept telling me to hold back.

Unlike the first time we visited, the place was fairly crowded, and there was a lot of swapping going on. Two couples by the far wall were taking turns with each other, and both of the women were also enjoying some spit-roasting (in this case, each woman was giving oral sex to one man while another man fucked her vagina; no anal sex happened the night we visited, though according to someone I spoke with, it occurs at times). Other couples arrived or moved from the chairs to the beds, but they didn’t seem as interested in swapping with others. I guess they were more about the exhibitionist/voyeuristic side of things.

Nina was enjoying the watching aspect a great deal and was getting extremely turned on. We kissed and groped for quite awhile, but she made no move towards the beds, and I told her that I’d stay on the sidelines with her until she felt the urge. At what I guess was around 12:45-1am, a very sexy, skinny woman motioned for us to join her and her partner, and we did. There wasn’t an empty bed left, but we found some space on the bed with the two of them and started kissing her. This was Svetlana, whom I’d later fuck to climax on a different bed. She was a bit weird, though, acting kind of like a tease. She wouldn’t let me touch her but would motion for me as if she wanted me to take her hands, and she didn’t take off her bra and sexy underwear. Eventually she started playing with Nina’s pussy, but she was rough, like a high school boy, putting in two fingers and finger-fucking her uncomfortably (or at best, un-pleasingly). I didn’t notice this because at some point, I had begun to play with another woman. I went down on her and then started fucking her. It wasn’t until I was having sex with her that I asked her name; she called herself Whimsy. I eventually went back to going down on her, so I wasn’t sure what was going on with Nina at all times. I do know that Nina ended up having sex with Whimsy’s date, Bob, and at one point we could see each other having sex with other people.

For me, it was really sexy to watch Nina getting fucked by another man, and it was sexy seeing her really getting off on it. She had her first orgasm of the night with him, and I made Whimsy come with my tongue. [Note: Like many of the women there, she had a partly-shaved pussy. I think you really need to decide to shave it all off or to leave it trimmed, but these vaginal five-o’clock shadows are rough on a person’s face!] I thanked her and then joined Nina, who was still on the bed with Svetlana and the Russian guy she’d arrived with. That guy had an odd-shaped penis that pointed up and to the side at the last two inches, as if he’d been injured during sex at some point. Nina didn’t want to do anything with him — he was giving off a strange vibe — so she ended up taking a post-coital break and watching me fuck the Russian woman. I alternated between going down on her — my tongue was sore tongue the next day! –and fucking her. I made Svetlana come while fucking her and considered allowing myself to come, but I really wanted to save myself for Nina and also wanted to continue having sex with as many women as I could and in as many configurations as possible. At one point while I was having sex with Svetlana, I found myself finger banging two other women, one on either side of Svetlana. I think one was Nina and the other was Whimsy. The night was often a pleasant blur like that.

I generally had no concept of what time it was while we were upstairs, but I found out later that a married couple named Lana and Mike arrived around 1:15 or 1:30. They quickly joined the fun on a bed in the middle of the long arm of the L. That put them next to me and Nina. I alternated going down on Nina and kissing her while Lana fingered her and played with her breasts; Nina had a the most powerful orgasm I would ever see her have, and then she put on some of her clothes and rested on the bed. She told me to continue having fun. It was hard to gauge whether she was a bit overwhelmed, or tired, or maybe jealous; had she asked me to leave, I would have done so, but she seemed like she needed a little time to herself, so I went back into the fray.

I quickly got to live out another fantasy, fucking Lana as she sucked off her husband. In fact, it was exactly as I’d hoped, with me fucking her in such a way that my thrusts pushed her onto his cock rhythmically, meaning that I was setting the timing for both of them to receive pleasure. Pretty soon we switched so that Mike was the one fucking her and I was getting sucked off (another fantasy), and I got super close to coming. As Mike got close to his orgasm, he told Lana, and she said that she wanted all of us to come at once, with me coming on her face. That was amazing, but I held back again so that I could come with Nina. I have a feeling that if I had come at that moment, Nina would have been upset.

When that was done and Lana and Mike were relaxing, I went over to the next bed with Nina, who had been watching us the whole time; she was smiling. She went down on me and got me extremely close again — in fact, I came in her mouth a bit — and then we rested. Lana and Mike were relaxing next to us, and I started fondling her again, and pretty soon Mike was rubbing her pussy with his hand to make her come again; this time she squirted all over the bed (some of which got on me and Nina); that was pretty amazing. Next, Nina and I went downstairs to get some more water and a robe for me (so that I didn’t have to put my clothes back on).

I still hadn’t had a full-on orgasm, so there was a lot of play left in me. At this point, Lauren went out for a smoke and many of the couples were finishing up; there was no more swapping upstairs, and after Lana got back, the top floor was empty except the four of us. I had little idea of the time — there are no clocks anywhere — but it must have been close to 3:30. Nina and I were hoping to live out one more fantasy of ours: having Mike fuck her while she went down on me. The problem was that Mike couldn’t get his erection strong enough to fuck Nina, and Nina didn’t want to suck off anyone but me. The four of us chatted a lot (we were eventually the only people still there). While hoping that Mike would be able to rise to the occasion, Nina sat on my face while Lana went down on me (another huge fantasy of mine). After a few minutes of that, Nina asked me to finish up inside her. We went at it one last time with Lana and Mike watching and had simultaneous orgasms; then we just lay there cuddling for 10 minutes.

After that night, we went back to the club just one other time, and it happened to be a quiet night like the first. We broke amicably up a few months later, and I never managed to get back to the club.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? We were exhausted the next day — we didn’t get back home till about 5am, and we both found ourselves awake just a few hours later. We talked about a few things we would do differently when we went back again, such as agreeing on signals in case we needed to communicate our feelings without words. And we ended up going back to that club again a few weeks later.

Our relationship went through several changes — exclusive for a few months, then FWBs again — before I finally broke things off sexually. We stayed friends for several months after that, but eventually she drifted off.

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

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting

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? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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 told various close friends, male and female, about it. They were mainly envious, I’d say, or perhaps just thrilled, vicariously, by the salacious details and the fact that they will probably never get to enjoy something like that. That is how I had felt up till then when friends had told me about group sex that they’d been involved in (such as threesomes).

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

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? It was great living out several fantasies in one night:
threesomes (MMF and MFF)
foursomes (MFMF)
voyeurism (watching others have sex)
exhibitionism (knowing that others were watching me have sex)
casual sex with strangers

What was the WORST thing about this hookup? I can’t point to anything negative about this hookup.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I feel like I’ve checked a few things off my list. I would be happy going back, but if that never happens, I’ll still enjoy the memories from that night and be satisfied by them.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? I don’t think it’s for everyone. Some people have very different ideas about sex and get hung up on things like seeing their partner have sex with someone else. Or they feel guilty about having casual sex, etc. So you really need to know yourself and to talk with your partner beforehand. It’s also wise to err on the side of not hurting your partner’s feelings. If you sense that your partner is unhappy, better to deny yourself some small, fleeting pleasure than to risk hurting someone else.

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? I’ve engaged in one-night-stands and also was faithfully married for over 15 years, so I know both side of the equation. I have always believed that sex is a fun act that can involve intimacy but doesn’t have to — like a back rub. I think that the world would be a much happier place if we put less stigma on sex and simply enjoyed ourselves as much as physically and mentally possible.

I also think that the more experience we can draw from, the better lovers we can be.

What do you think about the Casual Sex Project? It’s a wonderful way for people to see what’s out there, what they’re comfortable with, and what they do and do not want to try for themselves.

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

What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!