First Threesome And First Bisexual Experience

by Charlie

What’s your gender? Man
How old are you? 42
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, D.C.
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? 2

First Threesome And First Bisexual Experience

How long ago did this hookup happen? 8 years

What was your relationship status at the time? Single

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? My partners were a married male-female couple in their 40s (a few years older than me at the time). I responded to a Craigslist posting of theirs, in which they sought a man to join them for sex. They were suburban professionals with children, and I would likely never have guessed at how sexually adventurous they were if I’d met them in a different context. The man was fit and handsome. The woman was overweight but very pretty, and her breasts were spectacular.

After a few emails, we met for drinks and conversation at a local bar. It was a very relaxed and fun outing, and I felt comfortable following up. After we acknowledged a mutual interest and attraction, I invited them to come to my home and they accepted.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few years earlier, after decades of living comfortably as a straight man, I became attracted to another man and questioned my sexuality. I began to fantasize often about sex with men, but I was conflicted for a time about whether to act on my fantasies and, if so, how to begin. I ultimately decided that I needed to try having sex with a man at least once, so that I didn’t spend the rest of my life wondering “what if?” I think that the idea of being with a male-female couple was a comfortable way for me to take the first step, because I was familiar with and enjoyed sex with women. The idea was therefore a bit less intimidating than the idea of going into a 1-on-1 encounter with a man and not knowing where to begin. I felt comfortable enough with this couple to take the plunge.

When they came to my home, we had a glass of wine and talked for a few minutes, but with a clear sexual vibe. Before long, they suggested that we go to the bedroom. We went there, undressed, and got onto the bed.

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 woman lay in the center of the bed, with her husband on one side and me on the other. He and I took turns kissing her and kissing and sucking her breasts. After a few minutes, she reached out her hand and began gently stroking my cock. I was incredibly turned on, and in what seemed like only a few moments, I came into her hand. It felt great, and even after coming I was still turned on.

My main reason for coming to this encounter had been to explore with a man, and before long, the man was on his knees on the bed, facing me. He was still wearing jeans but opened them to reveal a hard, smooth, beautiful cock. Faced with the chance to finally realize this fantasy, I was a bit nervous, but excitement won out. I took his cock in my hand and held it for a few moments, then took it into my mouth and sucked him. It felt natural and exciting.

After some time, he asked his wife if she’d liked to be fucked. Her answer was something like, “That’s a silly question” – delivered in a way that was sweet and intimate. They fucked beautifully. Meanwhile, my cock had become hard again. When he finished, she invited me to fuck her. I put on a condom and fucked her until I came a second time. We talked for a few minutes afterwards and then they dressed and 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? The next morning, I woke up and remembered the previous night. It was exactly what I’d hoped for, as I had sucked a man’s penis and loved the experience. I knew that I wasn’t just curious, but that I was bisexual and that I would want to further explore sex with men.

I felt a bit awkward about how to proceed with this couple, because the experience was new and because of some other developments in my life. I ultimately saw them one more time, and we had a similar experience. They were charming and likable people who made me feel extremely comfortable, and I’m grateful for this experience.

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), Learning new things, experimenting, Thought it was an important experience to have

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? For a while, I told only one close friend (a lesbian woman whom I trusted). She was extremely encouraging. About a year later, I began seriously dating a woman, and I chose to tell her. In an extremely pleasant surprise, she revealed that she was also bisexual and that she was excited by my sexuality and experiences.

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? Exploring my sexuality, enjoying sex with a skilled and friendly couple.

What was the WORST thing about this hookup? Awkwardness because it was my first time with a man.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. Before this experience, I thought that I was bisexual and I fantasized about sex with men, but I harbored some doubt about how I’d enjoy the experience in real life. After sucking a cock for the first time, I knew that I enjoyed men and their bodies and wanted to explore further.

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

All things considered, how NEGATIVE was this experience? Not at all 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? Casual sex during this part of my life was very valuable, as I was exploring my sexuality and was able to do so safely and comfortably.

What do you think about the Casual Sex Project? I think it’s great – keep encouraging people to share!

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