by Katie

What’s your gender? Woman
How old are you? 18
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Some college (currently in college)
What’s your occupation? Student
What’s your current relationship status? Single
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)? 2
How many hookup stories have you here posted before? 0

Roommate Got Us Both Over the Hill.

How long ago did this hookup happen? 3 days ago

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 roommate Anne (and best friend!) and her friend Jack in middle school that reconnected in college. Anne is a tiny blond bombshell. She is really short, like 5’0″, but has a fantastic ass and enough up top. Also the cutest face ever. Jack is 6’6″, really thin, brown shaggy hair, but he’s started to work out and it’s had some effects.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It wasn’t planned, by me at least. Jack came over to our room to hang out and “study” on Friday, but snuck a bit of booze in. We ended up quitting on the studying around 11, and started to play silly games like never have I ever that lead to truth or dare when it was clear that Anne and I had done nothing and Jack wanted to change that.

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? At some point I was nude and pulling Anne’s panties off with my teeth. I then realized I had no idea how we had let it get this far, but I wanted to finally go all the way! Not long after Anne and I were making out and sucking on each other’s breasts and Jack was just loving it, jerking himself off watching us. Then I dared Anne to suck his dick, she said no way you do it and I did. Any pretense of the game stopped then. She joined me in trying to give him a blow job but it’s a lot harder than I realized.

He came on us then, we cleaned each other off (his cum tasted pretty good, though Anne didn’t seem to like it that much) and I pushed Anne down to continue the process. I had really never thought of being in this situation before, my family is very religious even though I’m not, but eating her out was really fun! Jack got hard again while I was doing that and stuck it in me. It hurt a lot, but it also felt really good. He fucked me for a bit before I made him fuck Anne while I sucked on her tits. Then he told me to lay on top of Anne so he could switch back and forth. That really didn’t work that well, but I got to make out with Anne some more and he ended up fucking me till he finished inside of me. It was really nice, and Anne ate his cum out of me.

It was really fun.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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 cleaned up after the hookup and he slept on my bed while Anne and I shared hers. When we woke up in the morning we tried to have a round two, but Anne and I were a bit sore from losing our virginities, so we just sucked him off and pushed him out the door to play with each other. That was really fun though, and I hope we’ll have Jack around again soon.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

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 more confident

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

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

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? No one yet, other than Anne, but she was part of it. She loved it just as much as I did!

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? Accepting that I am really attracted to Anne, and that’s not wrong. And that being attracted to Jack was still allowed despite being into Anne. I’ve tried not to think about it for a while, but even though its just been a few days I feel I can finally accept I’m bi.

What was the WORST thing about this hookup? We needed to recover in the morning so I couldn’t get pounded again! Sorry, everything was just so good I can’t think of anything else.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I want to have more of it, with more people, and that’s ok.

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? I’ve been taught that casual sex is bad, and wrong, and giving into the devil, but I hadn’t believed that for a long time. This really just confirmed it for me, and I’d like to have more of it.

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

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