Losing My Virginity in a Three-Way

by Anon

What’s your gender? Man
How old are you? 20
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Naperville
Highest education received: Some college (currently in college)
What’s your occupation? Student
What’s your current relationship status? Single
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Open to almost anything with almost anyone
How many sexual partners have you had in your life (including oral sex)? 5
How many hookup stories have you here posted before? 0

Losing My Virginity in a Three-Way

How long ago did this hookup happen? 2 years

What was your relationship status at the time? Same as current status

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 close friend from high school with is a tall extremely skinny nerdy dude and his girlfriend is a very attractive nerdy girl with a huge ass, glasses, and small perky tits.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It began with our group of friends all drinking in my basement together and my one friend bringing his girlfriend along. We were pretty clearly flirting with each other and instead of getting upset or anything a couple weeks later he calls me and asks if I want to have a threesome with them. Me being a lonely virgin I immediately said yes. So a while later I come to his house while they’re both there and we drink some booze and smoke some weed before I eventually start playing with her tits. She says, “He’s licking my nipple,” and he says, “I know, let’s go upstairs.”

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? It began with us all getting naked on the bed together and her sucking my dick. They both told me I should make some noise to indicate I enjoyed it since apparently it’s weird not to. Then she sucked his dick and she had mentioned that she didn’t like being eaten out but I wanted to try anyway. I licked her pussy for a bit and she quickly felt overstimulated and told me to stop. Then her boyfriend wanted to as well and she said the same to him. I started fucking her with her on top riding my cock cowgirl with him watching and me just trying to come for 15 minutes until we both got tired. She asked why I couldn’t come and I said it’s probably because I masturbate too much. He fucked her while I watched and then came inside her. She went to the bathroom to clean up and then it was my turn again. This time I was on top in missionary position and making out with her. I felt like I was getting close but at that point it had been an hour and her boyfriend asked us to stop fucking. At one point she commented on my foreskin and how she liked playing with and had never seen any before because all the guys she’d been with were circumcised.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

Did your partner have an orgasm? I don’t know

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? They went into the bathroom to take a shower together and had a conversation I was not privy too while I awkwardly got dressed on the bed and went home soon after. I had hoped that I would get to fuck her again but they had decided it was a good experience but only a one time thing. Me and her are still incredibly attracted to each other but behave ourselves out of respect for my friend.

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

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, To feel better about myself, To feel more confident

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol, Marijuana, hashish

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

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? Everyone I know. With shock and awe at such an interesting first time.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Finally getting some pussy, and making out with her while being balls deep inside her.

What was the WORST thing about this hookup? The awkwardness afterwards and during.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Absolutely, I think casual sex is a possible fun activity and I think open relationships can definitely be beneficial.

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 had all talked about me and him experimenting a little but none of that ever took place.

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 wish everyone accepted casual sex as something that can just be done without emotion or connection involved and just have a good time.

What do you think about the Casual Sex Project? Great

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