Everyone I’ve Had Sex With
Kyle was the most attractive guy at a Halloween party this year so we had sex in the basement. Unfortunately it was the basement of a girl who didn't know that people have sex at parties sometimes, and had a little sister who screamed, "get out of my house!"
By Megan Boyle
Adam: I had a big fixation on him that lasted all of high school. It happened my first year of college, on leap year, 2004. I’m glad it was him, I was a little drunk so I don’t remember feeling that self-conscious during it, but afterwards I did. It hurt, but in an exciting way. There were a lot of awkward moments. I weighed a lot then, probably 165. We used a condom, it was strawberry flavored, and my underpants said “POW!” on them like a Roy Lichtenstein. One of the best kissers. It was at a party which raised money for a hard cider home brewery. I bled on the sheets and he got them cleaned. Nice person. Terrible ex-girlfriend who he was still in love with. I was convinced that this ruined my life for awhile, but I don’t feel that way anymore.
Jake: I also had a crush on him in high school, based solely on physical attraction. If someone had told me in high school that I would someday have sex with either of these guys, I wouldn’t have believed it — not because they were ‘out of my league’, because I was painfully shy and insecure and didn’t really even talk to boys until my junior year of high school. Jake didn’t use a condom because I was on birth control, and that really shocked me, I used to think any time you didn’t use a condom you automatically got pregnant. We hooked up for a few years, on and off. Never kissed me, unless I asked.
Noah: We met in college. He was in acting school and had a fairy tattoo. One time we smoked weed under the el tracks and started making out. He liked Paul Simon a lot. Sex was kind of routine, but okay, he was a mechanical kisser. We didn’t use condoms. Happened a few times.
Nick: We went to summer session at an art school together in high school, then both ended up at the same college. He got in a car accident and died last year. I had a big crush on him, but he didn’t want to date me. We only had sex once, in the laundry room, standing up. My friend walked in on us. It was his second time. We didn’t use a condom. He told me I looked like a Greek statue.
Jess: Jess is a girl and she gave me my first orgasm from another person. We hooked up twice. We were really good friends. I wish we hooked up more. I wish we were still friends. It felt weird giving/receiving oral sex to a girl, like my head was above my body, and it was surfing or something. I don’t know how to describe it.
Ryan: Ryan ‘got lucky’ because he was a boy who hung out with Jess and I one night and we had a threesome. He reminded me of Frodo, I wasn’t attracted to him. We didn’t use a condom. We had sex for maybe three minutes. It only happened once. It wasn’t good.
Derek: Derek was Jess’ ex-boyfriend and one night we stayed up all night talking, I forget how that happened. We had a really good talk, got sleepy, and started spooning. Then we had sex. It was dry and unmotivated, I remember thinking “why am I even doing this?” We didn’t use a condom. I don’t think he came either. He said he owed me one. Only happened once.
Mike: Mike is Jake’s brother. We were/are really good friends. One night on spring break, a bunch of us had a fire in the woods and ate hot dogs. Mike came over to my house after that and we watched Return of the Living Dead and Night of the Living Dead, I think. We ended up spooning on the couch and touching each other’s faces for a long time. He took off his glasses and asked when my parents would be awake. I said “late,” and then it happened. It was really good, I was very attracted to him and he was a great kisser. I had a big crush on him that didn’t go away for awhile. We’ve hooked up several times. I’ve had a few orgasms with him. No condoms. Maybe once we used one.
Anonymous guy: We had sex at a friend’s party. I was drunk and I didn’t want to and I think I started crying and made him stop.
Dave: I’m surprised I remember Dave’s name. He followed me home from this party one night and we had sex in my creaky loft bed. I didn’t want to have sex. I had my period. I was drunk. He was persistent and I think I was really bored the whole time. He ‘dirty talked’ and it was annoying. I was mean to him. After he finished he said, “uh, one of us is bleeding,” and I said, “oh my god, is it your first time!?” and he followed me into the shower. I said, “you can wash up but then you have to go.” He wanted to stay. It was probably a 45 minute train ride back to his dorm. The next day he called me and asked if I had AIDS. I said, “no.” We didn’t use a condom.
Justin: Justin and I dated for a year. It was a shitty relationship but I think I just really wanted to be with someone, which is a shitty reason to be with someone, but I didn’t realize it at the time. Sex was okay, he gave me orgasms. It got boring/routine pretty fast. I ‘wore the pants’ in this relationship, which he didn’t mind on the surface, but I think it actually bothered him a lot. We had melodramatic fights. One night after I broke up with him, he sexually assaulted me and I dropped out of school. No condoms, ever, I don’t think.
Neil: Neil and I dated in high school and I broke up with him. Then we weren’t friends. Then we were friends. Then we were really good friends. Then I thought I was in love with him and we had sex one night. He gave me an orgasm. Then I told him I was in love with him and he rejected me. We somehow pushed through it and are good friends. I feel very comfortable having sex with him, I don’t feel self-conscious. One time he tried to fist me, and it felt very intimate and good, which surprised me. He’s physically curious in a way I feel I also am. Everything feels heightened with him. There is an open line of communication during sex, which feels natural and genuine. I have orgasms. We use condoms, mostly.
Steve: Steve was my other serious relationship. Over winter break 2006, I hung out with Neil a lot, and Neil hung out with Steve a lot, so I also hung out with Steve. I was still dating Justin at this time. Then I broke up with Justin. Then the thing with Neil happened. About a week later Steve and I drank mead and hooked up at Neil’s apartment. Then we hung out a lot, and decided to try a long distance relationship. Then I dropped out of school and it wasn’t long distance anymore. Sex was consistently good, sometimes great, I always had orgasms, he was a good kisser, he had a scar on his lower lip which I liked to feel. I felt an understanding with him that I have yet to feel with another person. We listened to the Velvet Underground’s “Self-titled” and Broken Social Scene’s “Feel Good Lost” a lot when we did it. I was the ‘big spoon,’ almost always. I broke up with him and treated him poorly towards the end, then immediately regretted it and drunk dialed him a lot. I regret a lot with him. We met at the wrong time. Sometimes we used condoms. He is a good person. We don’t talk.
Ricky: Ricky and I used to work at the same place. We dated for a month, after I broke up with Steve. After Ricky and I dated, Steve and I dated again for a month, and were ‘confusing’ for another two months. Ricky was a very good guy but not for me. Sex was pretty good, kind of too violent sometimes, but I still had frequent orgasms. He ‘dirty talked,’ and that always kind of removes me from sex, it makes it a parody or something. We used condoms.
Vincent: Vincent was an influence in my decision to break up with Steve, but I didn’t want to admit that for a long time. He was one of Neil’s friends. We flirted one Halloween and at his Christmas party we had sex. We sometimes had ‘dates,’ which were confusing. I was never sure if they were dates or we were just hanging out, but 97% of the time they would end in sex. One time at a big dance party I got extremely drunk and cried a lot and asked him why he didn’t love me, and talked about how existence is meaningless while sobbing for about two hours. We still hung out and hooked up after that. Our ‘thing’ lasted from January to March, then carried into July a little. I still like him a lot, despite. He lives far away now, and has a girlfriend. We always used condoms. He is a great kisser. Sex was adventurous, imaginative, very intense and had lots of eye contact. He never went down on me, though. One time we fell asleep on his basement floor, holding each other.
Jamie: Jamie is a girl. She was a very good kisser. It felt different in a good way, but I always feel confused when I’m with girls, like I’m one step outside of myself, watching myself. We have the same bedspread. She’s funny and I like her a lot. I wish I felt like I could have a relationship with a girl.
Anthony: I visited my former college to go to homecoming with my old friends. I met Anthony while dancing. He was a freshman and it was his first time. He was a really good kisser. I bought him and his friends a handle of gin (they paid me back) and we hung out in my old dorm. It was nice. I wanted him to be sure he wanted his first time to be with a stranger, he said he did. I left right after it happened. We used a condom.
Will: Will is Jake and Mike’s older brother. One day after a bonfire he asked if I wanted to come over to his house and smoke a bowl. We ended up having sex for ten hours, nonstop. It’s the longest I’ve ever had sex with anyone. We hooked up/hung out from February to May. We had a lot of fun together, he would make me breakfast and dinner and liked to be sung to. It felt like a relationship but it wasn’t. I wanted it to be, so I ended it. For a few months during Will’s and my thing, I was also hanging out with Vincent probably once a week. I thought that if I put together these two non-relationships that felt like relationships, they would make one whole one. Not really, though. We never used condoms, and I wasn’t on birth control. We have the same sense of humor. He had a foot fetish. He went down on me a lot. I had lots of orgasms. I liked being with someone who had a foot fetish.
Frank: Frank and I worked at the same place for awhile, but then he quit. We flirted a lot at work. One night I asked him to come over. He said “oh baby” and used my name a lot. I didn’t like it. I think I had to stop myself from laughing a few times. Afterwards I was hungry, so we got falafel. It was maybe two in the morning. He said grace before eating his falafel. I asked him what that was about. He said one time he did acid and saw god or something, and now he blesses his food. He mumbled a lot and didn’t make eye contact. I tried to get him to leave for about two hours and he finally did at four in the morning. Never responded to his text messages or calls after that. We used a condom.
Kevin: I was roommates with Kevin, but then we had sex and I think it made our relationship more complicated than it should’ve been. I was the aggressor. I wanted to date him. We had sex maybe twice, but a lot of nights we would make out or I would blow him and he would tell me to go to sleep. We got in huge fights and projected a lot of shit onto each other, I think. He never went down on me. He was a very good kisser and we used condoms. I felt intensely attracted to him. I never had an orgasm. I feel positively about him now.
Josh: Josh and I met at my work. He was very shy and we had the same sense of humor. He only mentioned to me once that he had a girlfriend, and it was to tell me that they broke up, but I inferred that it was probably a more ‘complicated’ situation than that. We hung out and hooked up a few times this summer, but I wasn’t sure if it was a ‘just sex’ thing and honestly I’m tired and bored of wondering this all of the time with guys, so I wasn’t motivated to find out what he thought. He was maybe the best kisser I’ve kissed. We used condoms, mostly. I would’ve liked to date him, under different circumstances.
James: I had known James through mutual friends for about five years, and this summer there were people over and he was one of them. I’ve always been attracted to him. He has a way of looking at you, but not at you, just past you or something. Pretty good/average kisser. Probably the most ‘adventurous’ person in bed. He lasted a long time. I had an orgasm. He wanted to do it again in the morning but I had to work. We didn’t use condoms. I said, “I hope you don’t have Secret AIDS,” he said, “I hope you don’t have Secret Pregnancy” and we laughed and parted ways. I feel good about this. (As of right now, I’m not pregnant nor do I have AIDS).
Kyle: Kyle was the most attractive guy at a Halloween party this year so we had sex in the basement. Unfortunately it was the basement of a girl who didn’t know that people have sex at parties sometimes, and had a little sister who screamed, “get out of my house!” This was a ridiculous experience and I think it’s funny, I almost can’t believe it happened. We didn’t use a condom. He was an okay kisser I think. It was just alright. We were both drunk. I was dressed up like a piece of pizza. I don’t think he had a costume.
Age at first time: 18 years, 4 months, 2 weeks, 0 days
Age at present: 23 years, 2 months, 2 weeks, 2 days
Total penetrative sex partners: 21
Total males: 21
Total females: 2 (2 not mentioned, I’m not sure they count as sex, it was just making out and fingering)
Total oral sex partners: 20-30
Oral sex giving to receiving ratio: 9:3 (probably)
Total official relationships: 4
Total ambiguous relationships: 9
Total one night stands: 11
Total partners I’ve said “I love you” to: 3, and maybe two .5’s
Total partners who have said “I love you” to me: 3.5
Alcohol involved in first sexual encounter: 13
Marijuana involved in first sexual encounter: 2
Total STD’s: 0
Total pregnancies: 0
Butt sex: 0
Came on my face: 0
Came on my tits/stomach/back/ass: 2+
Asked beforehand: 2
Places I’ve had sex: All rooms a house can have (not counting the garage), car, on a blanket under a tree, the woods, public bathroom, maybe — probably, laundry room, trampoline, started to on the top/roof of a construction site at night (he was not a construction worker).
What I felt after completing the list: Satisfied for having completed a task, surprised at how many details I remember, surprised at how passive I’ve been, detached from myself, angry at myself a little bit, self-pity a little bit, sad about failed relationships, happy remembering some moments/times of my life, irrationally hopeful, glad that I’m not in the past, puzzled at why I divert to other people to decide things about my personal safety, relieved that I don’t have AIDS or children.