"He was 16 and in a kilt."
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I was 15 and volunteering at the Renaissance Faire. He was 16 and in a kilt. We spent three weeks making out everywhere and generally being a nuisance and I lost my virginity in an open field. I hiked up my skirt and he hiked up his kilt. It was fun, silly, and nontraumatic.There was no pain and we were nice to each other but not "in love." He went back to college and invited me to visit but my mom knew something was up and wouldn't let me.
The crazy went to a different high school and was in the Theatre department. His mother was violently abusive and we spent most of our time lingering in his car while he cried, listening to Nine Inch Nails. We had sex on my parents' futon and in his ancient powder blue Pontiac behind a church. He flipped out when he found out I wasn't a virgin and said stuff like "How could you dirty yourself knowing your soulmate is out there?" Gross. I was young and stupid and we lasted almost two years, until he went to college and cheated on me with a girl who had her own apartment and "so many jizz stains on her couch it was crusty" (his words, not mine). They got married.
My Mostly Gay First Ex.
In high school I briefly dated a guy for a few months before "the crazy" but even though we liked each other, one day he unexpectedly broke up with me. Years later, I'm a freshman in college and he and I are talking again. He admits that he broke up with me because he mostly prefers guys but he still has a crush on me. We watched anime and would awkwardly get our swerve on in a lofted bed in my dorm. I wasn't in a good place for a relationship, though, and couldn't keep my head together. I was honest with him and we are still, 10 years later, friends.
The Party Dude
Enter the party dude. The party dude and I dated for five years. He was fun and loved me and his parents loved me and my parents loved him and over all, we were very supportive and invested in each other. But he also drank, a lot. We went to every party, had some great road trips, went to a ton of shows and had some of the best times of my life. But he would get drunk and we'd get into these gut-wrenching knock down, drag out fights. He was better at making out than having sex. One time we both got shitface drunk and blindfolded each other and ended up falling off a bunk bed. The sex was overall kind of boring, but the making out was pretty awesome. Things went to shit when I moved 2 hours away to go to a different college and he'd call me every weekend drunk, break up with me, and then call me in tears the next morning getting back with me. Our parents were disappointed because they thought we were going to get married.
The Gross Rapist
One night after Party Dude called drunkenly to break up with me long distance, I hooked up with a friend in a mindset of "well, Party Dude, if you're long distance breaking up with me, then we are broken up." Party Dude called me back after a day or two tearfully asking for me back and we worked things out again, because I was too inexperienced to just drop the ax on that relationship. I didn't know I even could. I was hanging out with Gross Rapist again thinking things would be chill, but instead he told me that if I didn't keep sleeping with him, he would call Party Dude and tell him, and also that he would kill my pet rat. I figured the sex was less trouble than the fallout from the situation if Gross Rapist told Party Dude. Also since Gross Rapist was closer and better integrated with the group of friends I was hanging with at the time, I didn't think anyone would believe me. Everything about this was awful and it was so stressful, I actually stressed myself into getting shingles. The story ends with Party Dude and I breaking up and me punching Gross Rapist and flipping him over a pool table in a bar, and Party Dude and I still being friends. None of the mutual friends between Gross Rapist and I believed me and I was ousted from that group.
Art School Dude and Lady
Art School Dude and I had sex a couple of times and then didn't see each other for a few months. He came back into my life with a poly girlfriend and we had a few fun threesomes before they moved to Europe. Overall positive experience. Sweet people. I don't hear from them anymore, but I hope they are doing well.
Always annoyed with me but hung like a moose. Fun sex, but I think he wanted a more hip girlfriend. I was kind of a tomboy. It was over when I showed up at a gathering with his friends dressed "tomboy goth" and all the other girls there were delicate trendy hipster types. We never spoke again, it was like he was mad at me for not being the right type of person.
I was living on my friend's couch for a couple months before I moved out west. He was my friend's roommate. We would hotbox his windowless room and have cuddly stoned sex. We looked a lot alike and our birthdays were the same day (different years) and everyone thought we were brother and sister, which was weird. We had kind of a White Stripes thing going on. We drove across the country together but I had to leave him in one city and go on to a job in another, and things fell apart because he didn't like the city I was living in. I regret breaking up with him but logistically things were not going to work.
We did mushrooms together for about two months straight every weekend. We ended up having sex a couple of times but then we lost interest and are still pretty good friends.
The lawyer was a friend from my hometown who happened to get a job across the country near where I was living. We had known each other for 10 years and we dated off and on again for 4 years. The sex was AMAZING. But don't date lawyers, they are awful. Everything about this relationship was a regrettable headfuck.
A Different Roommate
One of my roommates was notoriously poly and was having kind of a sad rebound when his primary partner broke up with him. We had some nice, fun sex and stroked each other's egos drunkenly for an evening. A really positive experience. We're still friends. (Actually maybe better friends than we were before.)
The Makeup Effects Artist
A bit older than me, a monster and gore effects artist. Really great guy, great sex, and a lot of fun to be around, but things got really serious really quick. I wasn't ready for a relationship after the lawyer. Another person I'm still friends with.