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What’s your gender? Woman
How old are you? 22
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: Some college (currently in college)
What’s your occupation? Student
What’s your current relationship status? In a serious relationship (open)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 41
How many hookup stories have you here posted before? 4 or 5

First Time Being DPed!

How long ago did this hookup happen? 2 weeks ago

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? One of them is David, my friend-with-benefits and my main sexual partner in the last month or so. David was the one I had my last threesome with (with my boyfriend) and that didn’t go very well. The other guy is David’s friend. Tall, latino guy. I first met him that day. I forgot his name so let’s call him A. We didn’t talk much at all before the sex, or afterwards, so like I’m still not sure how to feel about him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? David’s apartment. I had been asking my boyfriend and David for a proper MFM but my boyfriend kept refusing, so I asked David if we could do it with someone else. David took about a week to plan it, but on Sunday evening invited me over to his place. When I arrived there, David was leaving, saying he has to attend to something and will be back in 10 minutes (had to pick up some drugs.) So I was left alone with A.

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? A and I made some awkward conversation (he brought up religion, which isn’t something I want to talk about immediately before a threesome.) Anyway, I suggested to A that he could lube me up while David was gone (we would do DP so anal was pretty much guaranteed.) He agreed, so I removed my shorts and panties and he started to apply lube to my ass. He then fingered my butt for quite some time, while I mostly just waited for David to come back. Eventually I guess A had gotten horny, cause he started touching me all over, and we made out. That removed some of the inhibition between us, and soon I allowed him to penetrate.

This wasn’t the best decision, A is much bigger than David, who is much bigger than my boyfriend. I wasn’t even sure I could fit him all in my ass. Even though we were in doggy style and I was all lubed up, initial penetration was super hard, especially because I was so nervous about his girth. Eventually, he pushed about a quarter way in and I yelled and fell forward. Luckily he didn’t pull out, and my butt slowly opened up to him, partly because I was telling myself to calm down and relax. He kept pushing in, and we adjusted positions slightly so that he could get deeper penetration. Eventually his dick was nuzzled relatively comfortably halfway in my ass and he increased the pace of the penetration. Anyway, eventually David did come back, but by that time A and I were both nearly there (me through fingering myself.) Eventually I came, and a moment later A came in my ass.

Afterwards, I convinced A to stay and we did some drugs, about an hour later we actually started the threesome.

I convinced A to be the one below me, since I had read that the longer guy should be on the bottom, and also because anal with him had been quite difficult whereas David and I have been having anal regularly. We made out and touched each other for a bit, then I got on top of A, who was laying on the bed, and guided him inside me. David then pushed himself inside my butt. It was something I always wanted and the feeling was incredible. I just lay forward and savored the feeling as A and David built up a steady rhythm. They were pros, it seemed like they had done this before. David went harder and faster, but the feeling of another guy in my other hole was amazing.

They lasted quite a long time, which allowed me to try a few different positions. One on the sofa, on top of A, with David behind me. This allowed me to bounce on A and get deeper penetration. another position I tried was David on the bottom (but in my butt) with me facing A who penetrated my pussy. This was nice too, though an uncomfortable position to be in for too long. But A came in me before long, and soon after David did too.

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? I was sore as fuck when going back home. I haven’t met A again since then, though David and I still see each other quite often.

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, Attraction to partner(s), Learning new things, experimenting, Thought it was an important experience to have, Everyone else was/is doing it, It was easy / convenient

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol, Marijuana, hashish, Cocaine

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

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

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

To whom did you talk about the hookup? How did they react? My girlfriends, who were pleased. A few of them had done this already, but not most. And they wanted to hear how it was. I told my bf too, who was uninterested obviously.

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? The feeling of two guys inside me simultaneously.

What was the WORST thing about this hookup? Nothing!

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really. I’ve mostly become super positive about casual sex over the last year and this incident was just another one that showed me how great it can be to be open minded.

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 become increasingly more accepting of it. I was raised super religious but over time I’ve realized that it’s not good to be sexually inhibited.

What do you think about the Casual Sex Project? Great site!

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