"His partner of ten years (who I did not know about) showed up and started throwing things at me…"
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She was in my Girl Scout troop and we started messing around one night at a sleep-away camp. We shared a cabin and spent that first night alternately making out and fingering one another. When we got back, we would find excuses to hang out at one another's houses. The first pussy my lips ever touched.
I lost my penis-in-vagina virginity to this guy just before my sixteenth birthday. We'd been dating a long time in teenage terms — so maybe a few months — and we were "in love." He had only been with one other girl, which made the idea of having sex with him somehow more appealing. On the one hand he would know what to do, but on the other hand he hadn't been with too many people so there wasn't a lot of pressure to get it right. We broke up after my birthday, without regrets.
He was quite a bit older than me, twenty or twenty-one to my sixteen, so we lied to my parents about his age. He drove a t-top Corvette and let me drive it. I slept with him the first time on the same night that Princess Diana died.
Neil (and Brandon again)
I slept with Neil one night while my parents were out. I had Neil, Brandon, and another person over to my house. While Neil and I went upstairs to my bedroom, Brandon hung out with whoever else was there. Later that night, Neil hung out downstairs while I fucked Brandon in my bedroom. Brandon tried to convince us to have a threesome, but Neil and I declined.
We came from totally different economic backgrounds, which made it hard for us to connect. His was the first uncircumcised cock I'd ever seen.
We were good friends in high school and often messed around "just for fun" during sleep overs.
I only slept with Eric once. I felt pressured into sex with him. After it was over, I learned that he didn't use a condom, even though he acted like he was putting one on. It was my first experience with a true douchebag.
Jon, a.k.a. "Sexsquatch"
We started sleeping together in his bedroom at his mother's house. His mother would call my mom pretending to be a made-up girlfriend's mom, asking if I could sleep over. This was my first experience with adults who were willing to lie to other adults for not very good reasons. Jon was older than me by three years, and moved out of his mom's house while we were sleeping together, but his mom would still call and ask if I could sleep over with "Jenny" any time I wanted to stay with him.
This was a summer camp to remember. She was my first experience with a girl who identified openly as a lesbian. We used to sneak off to make out, and found several places to discreetly fuck during our month-long stay.
I was seventeen, he was thirty-four. I flirted hard with him for three days while working at this music fest. He finally took me in a van in the middle of the day and fucked the hell out of me. In my naïveté I thought that meant I would be his girlfriend, but when he found out how old I was he never spoke to me again. Looking back, I'm pretty sure he used a fake name.
This British expat was also too old for me, but not in maturity. He was twenty-two and lived at home with his mother and stepfather. He'd had never had a job because he didn't have a green card, but he had the biggest cock I've ever seen in my life. I cried when I broke up with him to go away to college, but he cried harder, and has never spoken to me again. I regard him as my first true love.
This guy was the lowest of lows in my sexual history. One time only, and I still for the life of me don't know why.
Aaron was a high-school friend who came to visit me at college. Though we fucked like bunnies, he stopped talking to me after one of my friends told him what a slut I was.
She lived on the same floor as me in my dorm at college. I convinced her to come back to my room one night, despite the fact that she'd never been with a girl before. She lay there awkwardly while I tried to get her off, and then quietly left in the middle of the night and avoided me for the rest of our time at college.
Cindy's roommate and I slept together fairly regularly, but always in secret. I have no idea if she ever knew I had taken her roommate to bed.
We both had internships at this company in Tennessee where we met and started dating. We went to college about an hour away from one another, so we kept dating after the internship was over. He had a small dick, which led to me trying anal for the first time. We broke up when I started dating Silas.
We met one night at a sushi bar. He had just gotten back from a year-long road trip. I fell for him immediately, and went home with him that night. It snowed that night, which was very rare for that part of the country, and the entire city shut down. It made everything seem magical. We dated for a year until he broke up with me by moving out of the apartment we shared while I was out of town. I was crushed, because I thought we were going to get married.
NEXT: “This guy (who was around twenty years my senior) gets a special place in my heart because…”
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…”
She was a cute little pixie with long blonde hair who spoke Japanese in bed. She only let me fuck her a few times before she broke things off stating, "I'm not really that into girls."
I went to visit him over a long holiday road trip. The sex was boring, and then he whispered, "I still love you," in my ear. I definitely did not feel the same way.
I fucked her in the bathroom stall at a bar the night I drafted her to my derby team. I was her captain, which meant this was against the rules. I never touched her again, but we're still good friends.
I was totally in love with this guy, but he had just gotten out of a long-term relationship and was very wary of getting involved with me. I got him to fuck me a couple of times, but mostly it was just making out and heavy petting after smoking copious amounts of weed.
I slept with her a few times while she was cheating on her long-distance girlfriend. Eventually her friends started whispering things about immorality in her ear and she broke it off.
The British One-Night Stand
I got pretty drunk and took this guy home from the bar. We had pathetic drunk sex and then he left when I drunkenly started to imitate his accent.
Yet another coworker. I liked sleeping with him because he was kinky and had a Sybian, but he was emotionally unbalanced and had self-esteem problems.
Jacob's best friend. I started sleeping with him behind Jacob's back, and dated them both simultaneously for several months. Aidan was entirely aware of the situation, but Jacob was not. Aidan had only been with one other girl, and he got very attached to me very quickly. I broke up with him the same day that he gave me an iPod for no particular reason, which was exactly a week after I broke it off with his best friend Jacob.
We dated for a summer. She was only a few years younger than me, but way less experienced in life and self-sufficiency. I helped her move from her third floor walk-up to a fourth floor walk-up. Not one of her friends showed up to help her move, and I ended up calling two of my friends to help me move her shit. When she told me it was a temporary situation and that she would be moving again in forty-five days, I broke up with her to avoid having to help her again.
Yet another coworker. We got very drunk one night and took a cab to my place only to never speak of it again.
After months of flirting, we dated for about seven months, but I never really felt that super-special thing that lets you know you want to be with someone for a really long time. When she started talking about love and moving in together, I broke it off with her.
He was a very short Peruvian man, probably five-foot-two or five-foot-three. We got tipsy and then we took a cab to his metal shop so he could show me around. He taught me how to use a TIG welder and rubbed his hard cock against my ass while doing so. We didn't have penis-in-vagina sex, but we spent almost all night alternating between him eating me out and spanking me while I was tied to one of his worktables. The next time we got together I was going to fuck him, but his partner of ten years (who I did not know about) showed up and started throwing things at me. I got the fuck out immediately and went to…
A bit shaken about being the other woman and getting random workshop tools and objects thrown at me by Andres' partner, I went to Leo's apartment. He is a very slutty man, and I thought he would be able to sympathize. He sympathized with me by convincing me to get naked while he massaged me. Then he popped a thumb in my ass and bent over to ask, "Is it okay if I kiss you?" To this day I still find this order of events hilarious. We ended up dating for quite a while, and even after we stopped dating we still got together occasionally for no-strings-attached sex.
This was yet another mistake in my sexual history. I didn't sleep with him at first because I got some weird vibes, but then I gave in when I saw his massive cock. He ended up being pretty upset when he realized I was seeing someone else at the same time, and called me a number of accurate names.
My longest relationship to date. I started seeing G either just before or just after I started seeing Bryan A. G was also seeing someone else. G and I dated for three or four months before I knew I wanted to be monogamous with him. He took a little more convincing, but eventually we both agreed to just be with each other, and dated for about two years. The sex was amazing and we were completely in love. I cried almost as much about losing his giant cock as I did about losing him.
My neighbor, a twenty-three-year-old fireman. Extra-large dick. Eight-pack abs. Several sessions of pure fun.
NEXT: “He has ‘RIDICULOUS’ tattooed on his body in huge letters…”
I picked this girl up at my neighbor's birthday party, and took her back to my apartment and fucked her brains out. Despite the fact that she insisted she was a top, she begged me to fuck her with my strap-on. I quickly realized she was bat-shit crazy after the slew of messages I got the next day, and never spoke to her again.
Another neighbor of mine. I was totally in love with him, even though I was pretty sure the sex would be awful. We only fucked once. Not exactly a highlight of my sexual career.
An Israeli man who liked to dominate in bed. We had a few fun times, but the sex was awful because he had issues keeping it up. I broke up with him by telling him that it was no fun to be fucked by a mooshy limp dick.
Yet another neighbor. I was bored, and the sex was boring. Never again.
If we had dated during a different time in my life, I would have had a long-term relationship with this man. The sex was great, and he liked to tie me up and spank me. He had a very nice dick and was a really kind man. I got scared when he said he loved me and stopped returning his calls. He forgave me and now we are good friends, and even get together occasionally for no-strings-attached sex.
I used to call him to come over and fuck me literally all night. He had trouble climaxing because of some sexual abuse when he was a kid, so I could basically get fucked as long as I wanted and then just tell him when I was satisfied. He stopped fucking me after he realized it was just sex to me.
Huge mistake. I knew before we even made it to his bedroom that I didn't want to do it with him, but I still let him take off my clothes and crawl into bed with me. One thrust and I said, "Umm, I need to use the restroom." I got up and put my dress on and he said, "You're not going to the bathroom are you? You're getting ready to leave." I responded, "Yes" and then walked out with my shoes in hand.
I went out on a date with this guy after he wrote me a cocky email on a dating site. We had great chemistry and I would have gone home with him that first night. He loved sluts, and so naturally we started fucking very shortly after that. I broke it off with him after I got tired of him blowing me off and lying to me about his relationship status with other girlfriend.
Leif (Part Deux)
I went to visit him on the other side of the state for New Year's Eve. He was so unbearably lonely that I slept with him that night, but regretted it the next morning. I wasn't in love with him anymore, but I felt like he still had feelings for me.
I met this guy on online and we went out a few times before I agreed to a sleepover. He didn't respect my boundaries and kept trying to force me to suck his cock. I've never spoken to him again.
Amazing sex. It figures though, since this guy was an actor in adult films. He broke it off with me because he knew I was interested in becoming his girlfriend and he didn't see that developing for him.
Ryan & Anne
A doctor and a nurse. I'm their occasional third, and sometimes I sleep with them individually. Ryan has been learning to be a better dom, as that's what Anne is into. Anne is a beautiful woman and it's incredibly easy to make her come. I like being in their orgasm sandwich.
I dated this dom briefly, and we had some really hot sessions where he made me come all over the place. Sadly the actual sex was lackluster and awkward because he needed to feel like his sub was emotionally attached to him, and I so wasn't. In the end I broke it off with him because I thought he was incredibly passive outside of the bedroom. He got very angry when I said I was dumping him because he "lacked teeth."
An emcee and voice actor with a voice like gravel. He rides a Harley and is covered in tattoos of varying absurdity (he has "RIDICULOUS" tattooed on his body in huge letters). He likes rough sex and fucks like a jackhammer when he's about to come. He has big fingers and uses them well. I let him stay at my house and fuck me whenever he's passing through town.
This is the first guy I've ever done it with who was a premature ejaculator. He was really good at oral sex, so I wasn't opposed to continuing to mess around with him (while seeing other people, of course), but he got distant after a few sleepovers and eventually called me to say he wanted to be just friends. I never decided if it was his own embarrassment over lack of performance that turned him off, or if it was his friends who warned him to stay away from me. I have a reputation in that circle as a sexual predator.
Oren (Part Deux)
We started fucking again after he hired me to work for him this past summer. The sexual tension was incredible all summer, and it was a huge release to start fucking him again. We're still fucking. He still has another girlfriend, but he doesn't blow me off anymore. It's not ideal, but the sex is the best of my life, so I try hard not to care too much.
This guy finally got me to go out with him after an excessively long period of flirting. We got drunk and ended up making out at my house, where he confessed to me that it had been three years since he had gotten laid. Being the good Samaritan that I am, I thought I would do him a favor, and I took him to my bedroom. He might have said no a few times, but his cock definitely said yes. I fucked him hard and left him scratched and bruised from my abuse. I felt very guilty and bad about this later, and told him that I regretted sleeping with him. I felt even worse when I found out I was only the second woman he had slept with, and that the last woman had been his high-school sweetheart that he'd married. They've since divorced.