They both held my hands and told me not to leave.
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Ken
After an epic breakup with my high school boyfriend (him dumping me as I sat in his lap: drunk, naked, trying to lose my virginity) I met this winner at freshman orientation. We hung out a few times before the magical night in my dorm bunk bed. The sex was terrible and I was drunk and tried to keep my boxers on. I left school with a nasty case of mono and when I came back he came over to visit me — and brought his new girlfriend.
Burt
I finally had sex with the ex who broke up with me! We stayed out all night at a Saint Patrick’s Day party snorting Adderall. I got a bloody nose all over his friends’ house so he took me home to his room — in his parent’s basement — and we did it. Nothing remarkable, but I thought I had strong feelings for him, so at the time it was fantastic. The next morning his dad came downstairs and he hid me under a comforter and pretended to be playing video games.
Years later, after he went through a serious break up and I was post college graduation and unemployed, our paths crossed again. I went over “just to hang out as friends.” Over a bottle of rum he recounted his breakup with the love of his life, and how he was meeting girls on Craigslist for hook ups but “even after smacking one around with his belt,” he couldn’t get it up for her. This really did it for both of us. He went down on me for about three hours then I rode the shit out of him. P.S. He had a broken foot. Two days we were at the same house party and he slept with my friend. We’ve since stopped talking.
Ty
We were great hook up buddies — he was always fun for a smoke and a makeout session. We finally did it during a house party. As he was thrusting away he started to cry “I think I’m going insane!” I thought it was a compliment until he had a mental break a few weeks later that culminated in him holding me against a wall screaming about shadow people, and me kicking him in the balls. He was checked into a mental rehabilitation facility. We’ve never spoken again.
Matt
I met him at a college party and we hung out a bunch of times; one memorable occasion included me blowing him on my couch while my roommate cleaned the bathroom. He invited me over to his off campus apartment which was super cool to me at the time. He also wore a smoking robe, which was also super cool to me at the time.
Will
Met at a college party while visiting a friend. Had a really hot body, but apparently used to be fat, so had no self-confidence. We had boring missionary sex which was mostly my fault. We hooked up twice over the weekend and it was a lovely three day relationship.
Dan
A longtime friend turned fuck buddy. He’d hooked up with many friends in our mutual friend group and our friendship was no exception. Over one lonely summer we started hooking up on the regular. He liked to jack rabbit but was a great kisser and really fun for a no-strings-attached thing. One time I woke up in his pants and no top. He now has a serious girlfriend so we don’t talk but I wish him well.
Seth
It was his 21st birthday and one of my best friends took me to his house party. He held my hand all night and I knew it was on. We did it in the guest room of his parents’ house and I remember being really loud. He showed my friend the scratch marks I left on his back months later.
Eli and Samantha
This was The Worst Thing I’ve Ever Done. My friend and I thought it would be fun to show our guy friend a good time at his bachelor party (he ended up divorcing her 2 weeks into the marriage.) It ended up with the three of us drinking a lot of vodka and taking Percocets. We all made out, which was fun until he pulled out his dick. He ended up fucking my friend next to me as they both held my hands and told me not to leave. I’m pretty sure it was the worst three way ever, but they ended up happily dating for years after that. So I like to think I brought them together.
Josh
This was my friend Eli’s best man. We made out all night after the wedding post The Worst Thing I’ve Ever Done. He was really cute and really nice. A year or so later, when he was back in town we ended up in my bed and had sweet, awkward sex. He wouldn’t take off the condom even to cuddle. It was perfect.
Drew
I was warned not to hook up with him as he tired of girls after two weeks, but I was interested and he was cute. We hooked up for two weeks and after hours of oral, fantastic dirty talk, and cuddling, I made him take me on a date. We had sex immediately after the date. He tried to pick me up to bone against a wall but couldn’t lift me. We ended our sexual relationship after that.
Tim
I thought that I really liked him because I’m an idiot. He was really nice and had a special pair of basketball shorts he’d let me wear when I slept over. When the rest of our friends came back for school, I saw him and a lady friend really hitting it off. I was jealous for about a minute but realized I had feelings for someone else too, and our fling was done. He’s now been dating that girl for 5 years and they are a blast to hang out with when I’m home.
?
I was visiting my friend at college and there was a themed party at a local bar. I dressed up as a slutty Hunter Thompson complete with Hawaiian shirt and gold hot pants. I was determined to sleep with someone and this lumberjack-style guy caught my eye. He took me home and all I remember is while we were going at it, he yelled, “You’re so much hotter than me.”
Xander
He was a guy friend who liked my roommate and slept with me to get back at her. He had the most fantastic dick and was a blast in the sack and the first time I really enjoyed sex. He was a little older and a huge slut and taught me a bunch of go-to moves and my favorite positions. Whenever we tried to hang out “as just friends” we’d end up naked in 60 seconds. After one sleepover, I drove him to work and he left his cell phone in my car — it was full of texts from his girlfriend I didn’t know existed. I drove back to his work and threw the cell phone at him. I was pretty upset until I remembered I got my period all over his bed.
Steven
The first person I slept with who I loved. We were friends all throughout college and I always thought he was really cute and kind. We started slow with long walks around the city holding hands and cuddling while we watched movies. We had some okay sex, some crazy sex, and some spiritual sex, and dated for four years. I ended up paying for most of his rent and he wouldn’t get his own car or laptop amongst other things, so tearfully, I broke up with him. It was the worst/best thing I’ve ever done. I still really care about him, but now I have a savings account.
Peter
Best rebound sex I could imagine. We met at my friends’ wedding — I loved his cocky attitude and laugh. After making out to a super romantic Ja Rule/Ashanti duet, I decided it was on. We hung out all night and got a room and had mind blowing, rough, dirty sex about six times in four hours. I had a bruise on my ass for a week afterwards and he sent me a picture of his back that I scratched up. We still have insane phone sex and plans to do it again — for science.
Zach
Came up to me at a friend’s wedding and told me, “I’d fuck the shit out of you.” I shrugged and we went back to his room where he had a major case of whiskey dick and no soul. He went down on me for about an hour but wouldn’t kiss me on the mouth or speak to me during the whole thing. He also told me not to tell anyone we had sex (if you can call it that?). Naturally as soon as we got back to the party, I yelled across the dance floor to my friend I’d had the worst sex ever with that guy and pointed to him. He tried to friend me on Facebook — what an ass.
