Foursome And First Anal Sex

by Charlie

What’s your gender? Man
How old are you? 43
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Washington
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 30
How many hookup stories have you here posted before? 1

Foursome And First Anal Sex

How long ago did this hookup happen? 5 years

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

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 met a bisexual male-female couple. My girlfriend at the time and I met them via a swinging website. We communicated quite a bit through email before meeting and were impressed with how articulate, sexy, and interesting they were.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My girlfriend at the time was also bisexual, and she and I had already had connected with one other male-female bisexual couple for a foursome which included oral sex between everyone. She had also enjoyed fucking me with a strap-on. We both fantasized about taking the next step. I had never received anal sex from a man but I wanted to, and she wanted to see it and be a part of it. Our ideal scenario was a foursome in which everyone connected with everyone. The man fucking both my girlfriend and me. This couple seemed to be a perfect fit in terms of their interests and experiences. R, the man, was naturally dominant (although not aggressive) and seemed excited to fuck me.

We traveled to a city near them and got a hotel room. We met them for drinks and appetizers and there was an immediate connection and attraction. After a few hours of talking and breaking the ice, we invited them to our hotel room, and they accepted.

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? We spent several hours together and for the most part had great chemistry. Each of us kissed and had oral sex (giving and receiving) with everyone else. R and I kissed and sucked each other’s cocks, which felt great. R then went down on my girlfriend while J, the other woman, sucked my cock. She was incredibly skilled, and I was soon close to orgasm. I told her and she surprised me by finishing me and taking my come in her mouth.

Next, both of our guests had vaginal sex with my girlfriend (J using a strap-on, R his cock). It turned me on to watch, and my girlfriend and I both really enjoyed this part of the experience. I did notice that J got very quiet when watching R fuck my girlfriend. Although we’d talked in advance about this being part of the experience, and she’d supposedly been in threesomes before, the reality of watching her partner fuck another woman seemed to bother her a bit.

I was both excited and nervous to have R fuck me. I’d fantasized for years about receiving anal sex from a man, and I loved when my girlfriend pegged me, but it was still intense to face the reality of the experience. Anal is the ultimate sex act between men. I was glad to have my girlfriend there to encourage me. She opened my ass gently, with her fingers and lube, the same way she did when she pegged me. When she felt me relax, we knew that it was time for R to fuck me.

R told me to come to the foot of the bed, and I obeyed. My girlfriend put a condom on his cock. I stood facing the headboard and bent over, putting my arms and chest on the bed and presented my ass to him. He stood behind me, grabbed my hips, and pulled me back towards him. I really enjoyed feeling him take control. I felt the head of R’s cock against my anus and although I was still nervous, I wanted him to fuck me.

R then said, “I promised to fuck you. I never promised to be gentle.” It was another display of his dominance, and it turned me on even more. Then I felt his cock in my ass. It was somewhat uncomfortable as I got used to the shape of his cock and the angle, but it wasn’t painful. As I relaxed, he began to fuck me, hard. My girlfriend took my hand, reminding me that she was a part of the experience and that it was something we wanted to share. I don’t know exactly how long R fucked me, but after a while, he reached a hand around, took hold of my cock, and began to masturbate me. I had a second orgasm from the combination of his cock in my ass and his hand on my cock.

Afterwards, we all spent about a half hour lying together and talking before the other couple left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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? My girlfriend and I went to dinner and talked about the experience. She was curious to know how I felt about having been fucked by a man. In fact, I felt great. It was an intense experience but a good one, and something I knew I would want to repeat. She’d also been incredibly turned on by watching. We had fantastic sex later that night while we talked about how hot the experience had been.

We wanted to meet this couple again, and emailed with them for a while about arranging a second meeting, but after a short while they politely told us that they needed a break from swinging. I think that this probably had something to do with J’s reaction to watching R fuck my girlfriend. It seemed like she wasn’t quite ready for that experience. We certainly didn’t have any hard feelings and wished them the best, although it was too bad she had felt that way, we would have loved to meet up again.

My girlfriend and I loved the experience and had other foursomes (with a different couple) until we broke up a few months later.

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, Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, Submission / Relinquishing power

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’ve told a few close friends and lovers about this experience. Their reactions have been overwhelmingly positive.

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? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Fulfilling the long-time fantasy of having a man fuck me. R was a strong and skilled lover and the perfect man to be my first. Having my girlfriend there, encouraging me and getting turned on by the experience, made it even better.

What was the WORST thing about this hookup? Only that one participant seemed to have a bit of regret, and that we weren’t able to repeat the experience.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’d already identified as bisexual going into this experience, but I’d felt like I needed to receive anal sex from a man in order to fully understand my sexuality. I felt like the experience completed me as a sexual man. I still fantasize about this experience and how exciting it was. I’ve been fucked by other men and women since then as well.

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

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

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? With a willing and eager bi partner, exploring casual sex was a great way of keeping our relationship fresh and exciting! It’s important to communicate and be reasonably cautious, but overall we had a great time. This experience definitely enriched my life.

What do you think about the Casual Sex Project? I think it’s great – keep sharing people’s stories!

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