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I had known Derrick for years, and had done some heavy petting with him while in high school, but it wasn't until college that we finally hooked up. I ended up falling for him pretty hard, and we had an on-again-off-again long-distance relationship for a year before he moved to a town about an hour away from me. We had a very one-sided relationship, which ended with me acting like a crazy person and him moving to Texas with the girl he was cheating on me with. We've never spoken again.
I don't remember this person, but his name is on this really old list I found that ends with "Fuck it, I'm twenty-one."
Very handsome, but had a fiance in another state. We slept together a few times until I started to feel bad about it.
I robbed the cradle and dated this eighteen-year old briefly when I was twenty-one. His inexperience made it pretty awful so I broke it off.
Pretty sure I only did it once with this guy my junior year of college. Years down the road he got hitched to a girl who'd been my roommate at one point. I don't actually remember sleeping with him, but he's on a list so it must be true.
We fucked for the first time at our friend's wedding, but we had also had a very PG-rated "relationship" our freshman/sophomore year of high school. It just felt so very nostalgic.
Total wastoid who I fucked in secret because it had been so long since I had gotten any. We did it a few times and then I got disgusted with myself and broke it off.
He came home with me one night after a few dates and we had mediocre sex. He announced upon leaving that he didn't think he would be calling me again, and asked me not to contact him. I still have no idea what happened.
I'm pretty sure I slept with this guy to make another girl jealous.
This guy (who was around twenty years my senior) gets a special place in my heart because he was the first person to tie me to a bed and fuck me. We only did it a few times before he got seriously involved with someone else.
Brandon (Part Deux)
He got my number from my mother when he ran into her in the grocery store. He'd moved away from our hometown, and so had I. We started chatting and having phone sex a few times a week. Eventually he invited me to his brother's wedding, and brought all kinds of sex toys with him. It was my first experience letting someone use toys on me, and it was amazing. That was the first time we had fucked in seven or eight years.
Silas (Part Deux)
Three years after our awful breakup he contacted me again. I went to see him on his farm a few times and we ended up getting back together for a long-distance relationship. He'd hurt me badly before, so I was more emotionally detached this time around. We dated again for another year and a half, and I broke up with him after I moved to Chicago.
He was my neighbor and lived in the same building as I did. We were friends for a long time before we ever slept together. When we did, he was cheating on his long-distance girlfriend and I was cheating on Silas. He was very skinny and his hip bones would bruise my thighs. Even though the sex was awful, I fell in love with him pretty hard, and was very sad when he moved back to the Midwest.
He was my roommate my senior year of college. We were bored, drunk, and extremely horny. We ended up having casual sex until I finally moved out.
Drew was my local boyfriend while I was dating Silas long distance, though neither of them knew about the other. We mutually called it quits when I moved to Chicago.
We got together out of convenience and loneliness, then eventually moved in together. He broke up with me by getting engaged to his ex. The sex vacillated between kinky and boring, but he was talented with his tongue.
I cheated on Matt A. with this guy. He was my coworker and a total douche, but I liked getting laid while Matt was out of town for work. I slept with him the first time while my friend Ed was in town for a visit. We both slept over at Jake's apartment, Ed in the living room on the pull-out, and me in the other room getting fucked by Jake with drunken abandon.
Susan's brother. I fucked him in the pool after her wedding.
He was my neighbor who lived downstairs. It was just sex, but it was really hot sex with mild bondage and lots of wrestling.
NEXT: "I was her captain, which meant this was against the rules..."