First Threesome

by FunBiGuy

What’s your gender? Man
How old are you? 41
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Manager
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 60
How many hookup stories have you here posted before? 0

First Threesome

How long ago did this hookup happen? 22 years

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

How would you best classify this hookup? Group sex

How long did you know the person before this hookup? For 1 to 3 years

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 GF was a small-breasted redhead with hips. She shaved below but kept a tuft of red upfront. We’d been dating about 6 months, and had done a lot. I actually met her in HS, but we didn’t date until college. The other guy was a guy I’d known for almost two years, as we became friends when we were freshman, and hung out a lot. He was shorter, with brown hair, kinda skinny and skater like.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My GF and I had talked about threesomes before. She was as interested as I was. We actually discussed having a threesome both with a guy and a girl, but the girl kept falling through due to bad timing. My GF actually suggested my friend, which I was perfectly ok with, and she did all the work approaching him and asking if he’d be into it. It was never fully planned, but it was a casual agreement we were all interested in.

When it actually happened, my GF asked us both separately at a party we were all at “do you want to tonight?” Which let to us finishing our drinks and exiting the party together, with my gf walking between us.

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 got to the dorm room and locked the door. It was a flurry of clothes being removed as she was stripping him while I was stripping her. She stroked him while I fingered her, and he played with her breasts and sucked on them. She must have been ready, as she was quick to lie down on the bed and make out with him, and not long after, she looked at me as she grabbed his cock and guided it in.

I stood in awe at first, as I had a great view of his cock inside her, and he was a lot thicker than me. It didn’t take me too long to get into a position where she could suck on me while fucking him. It didn’t last too incredibly long unfortunately, as he came pretty quickly.

After he came, he went over to the other dorm bed and watched as she went into position as I took her doggy. Eventually, I laid down and she rode me, and he watched as I played with her breasts, but he couldn’t get hard enough to join again.

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 didn’t talk about it a ton. My friend said he loved it, and said she was a freak in bed (all good things). My GF was kinda wanting to do it again, but the timing was never right.

I of course loved every minute of it. Unfortunately, the relationship for me was based on sex, so it eventually unraveled, but it was great while it lasted.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Hoping or expecting it would lead to something more

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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? We’ve only discussed it a few times.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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 the first time I’d seen another man hard. It was kinky as hell, and I still think about it. We knew each other’s status, so we didn’t use condoms, and using my friends cum as lube was a HUGE turn on.

What was the WORST thing about this hookup? He was a bit too drunk to go longer.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It started a string of things that eventually led to me experimenting with men and admitting my bisexuality.

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? Less taboo. People should be free to experience what they want to, without judgement.

What do you think about the Casual Sex Project? First time posting…

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