Love & Sex

Everyone I’ve Ever Had Sex With: Female, 21, Toronto

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"We had that kind of sex you can only have after a lot of build up. When you’re nearly attacking each other."

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My first sexual experience. She was the first bisexual I had ever met, also the only girl I had met to lose her virginity. We would get drunk at lunch and go to vocal class, wasted out of our minds. On one of these particular lunch dates, we ended up making out, then in my bed, then in my shower. It was awkward, I barely remembered it, and ended up being little more than a party story years later.


I was 17 and all my friends had lost it at 15. I was fairly sexually aware for a 17 year-old, I was eager to get it over with, and he was my best male friend. I trusted him, and I figured that was all that mattered, in the long run. We had awkwardly gone past being just friends that Halloween. I was a witch, he was a lifeguard, and he fingered me on our high school football field. He texted me one night when I was grounded and he was out at a party. He climbed through the basement window; we drank half a bottle of raspberry vodka chased with diet coke. We started fooling around, we pulled the bed part out of the couch, and before you know it, we had sex. It was awkward. He was clearly nervous, as was I, and it lasted about 45 minutes before my vagina begged for mercy and I made him stop. He asked if he could leave out the front door. I said no.


He sat next to me in biology, his girlfriend sat next to me in French. We hung out at a party conveniently located two houses down from mine, and after a few drinks and a blow job in the bathroom of that girl’s house, I invited him back to my place. The pullout couch saw some more action. His girlfriend confided the next day that she thought he had cheated on her, and I almost had a stroke. To this day she has no idea.


One of the first times I used my fake ID, I went to a bar with some friends from high school (we had just graduated). This particular guy had a famously large penis, and when he made the charming move of writing “i want to fuck you tonight” on his phone and passing it to me under the table at the bar, how could I resist?


He was super popular in high school (I was not), and we made out once at a party when we were 15. A few years later, when I moved out on my own, I was feeling bold (drunk) and asked him over. We ended up being fuck buddies for a bit. He thought it was hilarious to call us fuck bunnies. He was not the brightest, but damn, the sex was amazing. He was so goddamn pretty, with his hard body from working out for so long, his sexy scruff, and his curly black hair. He eventually ended it because he wanted to date a virgin. Go figure.


Oh god. The worst of the worst. He was 27, I was 18. He was living with his pregnant ex-girlfriend, he thought it was love, and I knew better despite my age. I would get lonely and horny, call him over at 2 am, have crazy sex, then demand he left the next morning. I might have been a mess.


Another mess. I worked with him at some point, met him at a club after downing several Percocet and several Jager bombs, and woke up with the most hickeys I have ever seen on a person. And 60 bucks and a quarter of weed missing. That was an awkward 9 am staff meeting.


My supervisor at the cheesy fake Italian restaurant I worked at. Also my pot dealer. He had been hitting on me as long as we had known each other. I got bored one time when he was dropping off weed. He came in and we had extremely rough sex. He still texts me to hang out occasionally, although it was for sure a one-time thing.

Dan A.

He was a host at the Italian place, I was a server. He was a year younger, so adorable, and we flirted madly. I always called him “little boy” jokingly, and he always pouted in a super cute way. I never considered him seriously at all. One night he invited me to hang out with him and his friends. We all played beer pong and laughed, until one by one, they fell asleep at the frat-like house we were in. When just Dan and I were left standing, he awkwardly asked if we could fool around. I found it terribly endearing, and we ended up having sex on someone’s bed that was out of town at the time. He lasted less than two minutes, and when I tried to get him to go again, he basically told me it wasn’t happening. Clearly still a little boy at heart.

Dan K.

Pretty cool guy. He worked at the Italian place with me for a bit. I was never super attracted to him, until one night we were out, and a good friend of mine started flirting with him. I got super unexpectedly possessive, and just HAD to fuck him that night. The sex was pretty good, and we managed to remain friends for the remainder of his time at the restaurant.


I thought Adam was my ideal man and I pined over him. Manly, big guy, always wore plaid, grew a Chuck Norris-style beard. I finally managed to get myself at his place alone after a night at the bar with our mutual friends. We had great sex, just like I pictured, but I spent the following summer celibately pining over him some more, because I was too stupid to know that I liked him more than he liked me. We had sex one more time (entirely my plotting) before he broke the news that he wanted to be “just friends." I celibately pined for 8 more months, until I moved away.


I heard about Matty before I ever met him. Everyone I knew said he was a giant teddy bear. So cute, so nice, such a good guy; they all missed him because he was temporarily away. When I met him, it was lust at first sight. He was the tallest man I had ever met, and he was a big boy, too. So much that my curvy self felt like an imp in the sweater I stole after our one-night stand. I thought we had a connection. He thought I was a crazy slut.


Craziest person I have ever met. We started hooking up after I had hooked up with Matty, and she pretended she was fine with the fact that I had a one-nighter with him. Until one night, she invited me over, kissed me, started taking off my shirt, and then told me he was coming by to get his drill back. I asked if she wanted him to walk in on us. She said yes. The last time I ever saw her, I bummed a smoke off Matty in the smoke pit at a bar. She came up to me and screamed in my face about what a whore I was for about five minutes. Matty backed away slowly.


Some random Australian guy I picked up when I was really angry at Matty. Don’t quite remember his name, just remember him trying to thrust his half-hard tiny penis in me for a bit before I got so fed up, I shoved him off. Not my proudest moment.


Ah-dorable. Met him in a club, immediately thought I’d take him home, and ended up walking home with him. He lifted me by my ass onto the bridge on the way home and told me he “had to talk to me because I looked so free” at the bar, and kissed me. I lived in a dorm-style room and had to ask my roommate to go to her boyfriend's place when we got back to the room. She reluctantly got her stuff together as I went to the bathroom. When I got out, he had picked up her boyfriend’s guitar and was singing her a song about how he was sorry she had to leave, but he really wanted some alone time with me. Great sex. After we were done, he asked if I came. I said yes and we high-fived. His bar change fell on the floor with his pants. He didn’t pick it up, and it happened to be the exact change I needed to wash my sheets. Best one night stand of all time.


The only person I regret having sex with. My roommate was dating him all summer. She broke up with him before she left town. He asked to hang out with me, and I accepted because I felt bad for him. When he put his hand on my leg, I knew what he wanted, and I did it just to get back at her for all the shitty, shitty things she had done to me that summer. Revenge is not a good reason to have sex with someone.


Brady was my boss all summer. I was slightly attracted to him, but I kept it under wraps because I thought it would never happen. He was Australian, a bit of a manwhore, 15 years older than me, and every time he would say something sexual around me, (we worked at a kitchen, it was often) he would get afraid I would take him to “haich ahhh” (HR to all normal people).

We had a running joke that he thought I should be more ladylike, and so when he asked to take me to dinner, I decided to tease him a little by putting my sexiest dress on, doing my hair and makeup, like he had never seen me before. His eyes nearly popped out of his head when he saw me, and later that night at the bar, he looked me in the eyes and said, “Fuck it, come home with me”. We had that kind of sex you can only have after a lot of build up, when you’re nearly attacking each other. Unfortunately, it was my second to last night in town, and the next night he was over and we had sex again. I’ve been home three weeks and I miss the fuck out of that fucker.