What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? US
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: Jewish
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 200-300
How many hookup stories have you here posted before? 0
Football Watching GB
How long ago did this hookup happen? 2 years
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? The woman– let’s call her Ayn– was a pornographic pin-up. 20s, tiny frame, leg gap, couldn’t have weighed more than 90lbs– and large D-cup fake breasts.
When I first saw her pictures online (on an adult, couples-oriented site), I doubted she was for real. I’m very glad she was.
The other people there included her BF (older, decently built, trashy douchebag) and four other guys. Two of them were, like myself, 30s, well-built, attractive. Two were decidedly not. It was clear the bf had made the selections and hadn’t been that discriminating (at least not at the end).
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The couple had posted on the website that they were interested in a GB while watching football playoffs on TV. She would service all the men repeatedly. It was a fantasy of hers. The whole thing was to take place at a somewhat remote hotel.
Lots of anxiety/anticipation leading up. Was she real? Would she look like her photos? Even if she was, was she just bait for robbery…or worse? I’d used the website to do a bit of verifying. I don’t think I would have gone were it just off CL. But who knows. I was in a weird place.
When I arrived, thankfully, she was real. And looked exactly like her pictures. She was in a tiny negligee, showing off her amazing body, sitting on her bf’s lap. She got up to give me a hug. Most of the other guys were already there. We were in a suite. I took a seat on the couch next to a couple of other guys. Another guy arrived soon after, sat across. We were ready to begin.
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? Ayn came over, sat between me and one other guy, and began rubbing us both over our jeans. We took turns kissing her. We pulled down her negligee and played with her large fake breasts–absolutely massive on her frame. She took out our cocks. I’m a little over 8″–he was maybe 6.5″. She was happy to have them both. She stroked us, started sucking us, and then stood up and indicated we should follow her into the bedroom.
It wasn’t long before the rest of the clothes came off and we found a natural enough position. She began to suck me, he worked her quickly with two fingers until she squirted, then grabbed a condom and fucked her from behind. She could coordinate well with two cocks and seemed genuinely excited. Then he pulled out and came around, I grabbed a condom, and she started to ride me while she sucked him. He asked if she liked DP– she said no anal, so he asked about double vaginal. This hadn’t occurred to her. She wanted to try. So with me under and him coming from behind, we stretched out her small pussy until she came again. After this point, we both pulled off our condom and jerked off/were jerked and sucked by her til we both drenched her face, neck, and tits in our cum.
I could have gone then, but she was so fucking hot– so truly slutty–that I wanted to stick around and see what would come. She came out. Fooled around with her boyfriend a little. Pulled him out and sucked him briefly. He told her to get back in the bedroom. Another guy went in there–a less attractive guy–didn’t last too long. Then the least attractive guy went in. I couldn’t see much and was starting to get bored, so I decided to go the bathroom–through the bedroom–just to get a sense if there was a way to get back involved.
My timing was good. By the time I came out of the bathroom, the guy was getting up to leave. He lasted even less than the other guy. I smiled at Ayn. She waved me back to the bed. She said the guy was so small it was awful. She wanted a big dick again. She wanted my big dick. She told me she needed cum. More cum. She actually called herself a cum slut. I saw her reaching into her pussy, scooping out something white, and eating it. That’s when I realized she’d just barebacked this guy. Part of me was freaked out–who does that with a stranger in a gangbang–and of course, part of me was turned on by the sheer wantonness. She was already holding my cock and pulling me towards her. I barely whispered–no condom? She shook her head. No condom. She took me into her. For someone who had already been fucked so much–including DV–she was shockingly tight. I pounded her. She was happy again. I grabbed her tiny ass in my hands, pulled her apart, bottomed out over and over. She came again. And when it was my turn to cum, she begged me to do it in her mouth. I pulled out, came all over her tongue.
As I walked back into the living room, I felt exhilarated… and suddenly terrified about the unprotected sex. I saw the next guy in. The last guy. Only other one there with a big dick. I saw him prop her up doggie style and enter her from behind. Also unprotected. I thought about staying for another go, but the spell was broken. I was now getting worried. I got out of there.
How sexually satisfying was this hookup? Somewhat
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 felt really fucked up after. She was super hot. The sex was hot. Her craving my cock and cum–and cock and cum in general–was hot. And the sheer slutty wantonness of the unprotected element was hot… but just way too risky.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal, Condoms, 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, To feel better about myself, I was feeling lonely, Boredom
How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it
What substances did you consume? Alcohol, Marijuana, hashish
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
Did you get emotionally hurt as a result of this hookup? Somewhat
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? Somewhat
Why do you regret this hookup? I got really freaked out about the unprotected element. Didn’t do anything sexual for the next 3 months until I got all my tests back. Thankfully negative.
What was the BEST thing about this hookup? Her breasts. Her waist. Her ass. Her amazing little body. How much she wanted to play the role of a porn star fuck toy. How good she was at that.
What was the WORST thing about this hookup? The unprotected element. Also, her bf– who was kinda creepy and douchey.
All things considered, how POSITIVE was this experience? Somewhat positive
All things considered, how NEGATIVE was this experience? Somewhat 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? Sometimes it has been wonderful. Expanding my mind, my friend group, my interests. Other times it’s been a distraction.
What do you think about the Casual Sex Project? Love this site. Love reading it.
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