Stories by strangers and friends.

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A lot of things changed for the better for me the year I had sex for the first time. I was sixteen and I was always on my bike. That year or the year before, I had started biking to my high school, a half hour's ride downtown. I was coming into my own, emerging a confident kid from a bookish and often insecure preteen chrysalis. I had a mohawk that I rarely had the patience to spike, but sometimes my friends did it for me before a show or whatever. We used to use this really gross hairspray.

Anyway, I had been out to myself for years now, and had even told my friends I was bi and I was just dying to get with a guy, man. Seriously, this was all I could think of. Every day after school I would come home and jerk off thinking about - almost literally - every guy in my grade.

So one night, pretty drunk, biking home from something in the east end. Maybe it was a bush party at Edwards Gardens. Brickworks? House show? Whatever. I guess I had started taking big detours on the way home. Yeah, so, I would often end up down Church St. I was desperately curious. I was really nervous too, but not why most teenage fags were.

You see most weeks, late on a school night, I would steal off to the basement to watch the latest episode of Queer as Folk. I was fascinated, since I guess it was the first time I had seen gay people's lives up close. But I hated pretty much every character and what they were doing. I was a punk. I had everything that mattered to me – I had a scene. It really was a second family. Only thing was, there weren't many other queer punks I knew of. Was I eventually going to have to start listening to house music and going to drag shows? Was I going to have to sell out? I still hadn't resolved that in my mind, when I found myself on another late night detour through the gaybourhood on my way home, bright eyes.

Stopping in a park for a smoke - warm night. This guy comes up, handsome, older and really friendly. He kept saying how cute I was and I couldn't stop grinning. I'm touched by the attention and we talk for a bit until I tell him I've got to go. He makes me put his number in my phone. I bike home excited and hoping I didn't come off that way.

I call him back that weekend and ask if he wants to meet up. He sounds surprised to hear from me. He tells me to meet him at a corner near St. James Town, the biggest housing project downtown, which I do a few hours later. When I get there, he's getting out of a cab and he's waving goodbye to this wee lady who drives off in the cab. His Jamaican Mum, he tells me. We go up many floors in one of the towers and enter an apartment. I'm really excited to be alone with him! When we get in, there's a guy in the room watching TV. We say hi and go straight into the bedroom. Whatever.

I pull out the 40 of beer I had for the occasion, and he is surprised again, and pours some for us and gives the rest of the bottle to the guy in the other room. We're alone in the bedroom. He's so handsome. I start to kiss him and he kisses me back. He laughs and tells me we can take our time and how hot I am. I'm in heaven. He gets completely naked and sits back down on the chair next to the bed and loads a crack pipe. I don't often tell people this part of the story, if I do tell this story at all. I'm not sure if I had already tried crack by that time, or whether that would be later on. I'm pretty sure it wouldn't be for a while. I was so eager to touch him, to feel him, and I promptly started sucking his dick before he was even done with that.

I remember we were both so turned on and excited and happy. He was so gentle - so sexy! God, I'm getting goosbumps and a semi just thinking about this. Imagining his big black body up against slight frame dusted in red hair – man! When it was over, we lay there enjoying ourselves. I can't believe it, but I actually told him that that had been my first time and he laughed and said he didn't believe me!

I never saw him again, and only recently have I become unsure of exactly what his name was. It's one of two possibilities. I've always been really bad at remembering faces, so that's pretty much out, unfortunately. But he was a huge deposit in my spank bank and still is one of my most powerful fantasies. In school after that I would often smile when thinking back to that, imagining how utterly incredible an experience I had had. How unfathomable it would have been to these gangly brainiacs I sat beside every day. None of my friends would've ever believed what happened, and when I finally was forced to tell it to one of my best friends, he was awestruck. Ha! But as I biked west along Bloor that night, across the whole city grinning it felt like some crazy wish had come true! I had done it!


When I was 15 I fell in love. Unlike other boyfriends, I knew I loved this person because I liked him more after we started dating, rather than less. This was also good news because I could have sex for the first time with “my boyfriend”. I didn’t know much about sex, and had only read magazine articles that told girls “What Boys Like” and “when to go “all the way” with him”. The ratios of my relationship according to Seventeen magazine made it clear I was ready to go “all the way”. Of course, putting relationship information into practice was less straight forward. I learnt early on that teeth were usually a bad thing when it came to blowjobs. I had thought it was like kissing, where you could tease the person with “love bites”.

Having ‘sex” for the first time is supposed to be memorable, like the first kiss. Both of these experiences were unmemorable for me. They were probably more of a lesson in what not to do, rather than a beautiful moment I had planned in my head. However, somethings did stay true to form. I promised myself that on our six month “anniversary” we would have sex, which happened on a couch. The couch seemed to be the major place for these activities from age 15-18. I remember having the luxury of a bed once or twice, which was both highly exciting and a little weird. Things seemed too crisp and clean and I didn’t have popcorn or a dime stuck to my butt.

I don’t know what counts or not anymore, in fact counting in general has completely gone out the window. I think this is a good thing. However, I do remember the first time I ever had a penis inside my body (which was not recorded as my first sexual act, but maybe it should have been). This was around the three month marker of the same relationship. The setting was Hilton Head, South Carolina, March break, 1997. I had been allowed to take a trip with my boyfriends family for the week. The troupe included him and I, his father, grandma and grandpa. I actually remember getting a handjob underneath a blanket in the back seat of a Cadillac sitting next to his grandmother on the drive down. Handjobs were really big at this point in the relationship, and obviously seemed to happen at interesting moments. I think we were listening to books on tape in the car, but can’t remember the book. Anyway, this segues into the penis story. I was becoming more and more interested with what it would “feel” like to have a penis in my body. I don’t even think I was using tampons back then, so there was a good chance that very little had made its way up there. One night on this trip we watched a movie with his dad who ended up snoring on the couch during most of the movie. While this situation would never happen anymore, I guess back then we took the opportunities we were given. As his father lay sleeping mere meters away I decided I wanted to take the next step. The difference between this and sex was important, because I am a toe dipper. I don’t jump into the pool unless I have to. So in a way it was almost a medical probing. I sat on top of him and slowly inched my way down his penis until he was completely inside me and I sat flat against his stomach. We sat there for a while and I questioned him about what I felt like to him. I wondered whether if I waited long enough he would come. He said that that might happen. His father never woke up, based on the snoring, but you never know. I have been in his position since and lay frozen until it was safe to be awake.

FF 5

When i was 15 i started dating my best friend "Darrin" who i had known since grade 7. We were drawn to each other from the first day of middle school because we were both silly and made weird jokes and liked Nirvana. He had an IQ of 187 and when he was a little kid he was featured in an article in McClean's about geniuses. He got expelled from school in grade 9 because he stole people's backpacks, and got really drunk this one time at a school dance and ran away from the police and then threw up in the principal's office. We started dating the next summer. We already knew that we loved each other so we decided to have sex right away. I had only just gotten my period for the first time like 2 weeks before, and had my first kiss ever (with him) the week before that.

I don't remember much about the actual event. That evening we had been hanging out on the beach smoking pot, so that may explain why my memory is fuzzy. We were in my dad's basement on the floor, and i don't think any music was playing but we had the TV on, but the sound was off, and all the other lights were off. I remember that Darrin took off all his clothes right away but it took me forever because i had never been naked in front of a boy before. So my getting undressed dragged on for a couple hours. i think i kept darting to the washroom to look at myself in the mirror just to make sure i didn't look too fat or gross. I was also too nervous to really start because we had never fooled around more than just kissing, and i was pretty embarrassed to touch him.

Eventually we started having sex, and i remember feeling pretty OK about the whole thing. It didn't hurt and it didn't feel amazing but it was fine. Darrin didn't come so we just called it a night after about half an hour. It happened around 4:20 in the morning, and we thought that was cool. At school the next day i also felt cool because i was only the second girl in the grade i knew of who had had sex. Darrin and i didn't end up having sex again for several months after that, because we probably weren't really ready for it. We did end up dating for almost 4 years though.


I considered it a great prize to be led on my Sexual Way by an older, experienced woman. Though I suspect young male virgins are also coveted , if not merely for the sport and story.

She was living at home, though, relatively removed in the basement where we bided our time with endless squirming chemistry games. It was decided that waiting until her mom split for the weekend was the best laid plan, as this would afford us all the time and privacy needed for my lengthy indoctrination.

And when the weekend came there was no second guessing her mom's absence. The arrangements had been well laid out, right down to a fresh box of Kleenex and pre-poured glasses of water within arms reach of the bed. At first I thought she had tuned into the severe cold I had just picked up, with thoughtful consideration, but there was no mention of that and I was promptly thrown to the bed.

Anyway, I came in like, two minutes. Then I passed out from the NyQuil I had mistaken for DayQuil. Later she told me that she fucked me two more times, all while I was, more or less, unconscious. To me (and prematurely) this was an indication of virility, though, I was soon corrected on that point.


it was morning and i forced him into it, knowing that we wouldn't be together forever, let alone a week more. i just wanted to get sex over with.

when he left, i felt elation only in connection to having lost my virginity.

later that day, my ugly jock roommate told me that he'd slept with 27 girls.


I lost my virginity at a sleepover camp for rich kids. I grew up in a townhouse apartment and went to public school but by the mid 80's my dad had a good job so he sent my brother and I to this fancy camp where they had sailboats, horses, waterskiing and everything a kid could want. The camp was filled with well-bred private school girls from Branksom Hall, wealthy international kids and a bunch of rich boys mostly from Upper Canada College. I had never known private school boys but the competition in those schools must be fierce, because these guys were some of the meanest motherfuckers I have ever known.

In my first year at the camp, I learned about a new form of torture, a kid in my tent held me down with a paddle and slowly spat in my face only to suck it back up quickly over and over again. I was awoken in the night with Purple Nurples, had all my personal stuff spread into the woods and adopted the worst nickname that stuck with me every summer for years, "Pickle." I don't know if I got that nickname because I was a late bloomer and everybody else around me had gone through puberty or the fact that I wet the bed and would crawl back into my wet sleeping bag every night, thereby "Pickling" myself.

I loved being the underdog; I must have because I went back to that camp for four summers. Eventually I did go through puberty, outgrew bedwetting and kissed some of the prettiest girls in camp.

The girl who took my virginity was my CIT (Councilor in training). I liked her right away when I met her; she was a confident, healthy, fertile North Toronto girl. She described herself as having Alabaster skin, it was soft pale and almost transparent. A councilor dating a CIT is forbidden at camp, which gave it a little extra excitement, but to my discredit, probably a little easier score on my part. Despite being a year older she really did call all the shots in our affair.

We went on a five-day canoe trip together, taking care of a bunch of kids and traveling around Ontario lakes and islands. On the last night we stayed by the fire after the kids had gone to sleep and got romantic under the stars. We took our smooching into my tent so the kids wouldn't catch us; we kissed and rolled around until the tent became to muggy and we ran out of oxygen. She told me she was on the pill and had sex regularly with her previous boyfriend. I lied and said I had lost my virginity to a girl I had only fooled around with at school.

When we came back to camp we acted like nothing had happened but I would sneak into her tent/cabin at night. One night she said it was time for us to have sex; I lost my virginity as silent as I could because there was four other CIT's sleeping a few feet away. It was a missionary affair because she told me sex from behind wasn't respectful and I really was glad to have it any way I could. We continued to have sex that summer everywhere we could and I developed a big crush. I remember bringing our sleeping bags out to the woods and having stuffed up allergy sex where you can't kiss much because you can't breath through your nose.

News of our affair got around and eventually they called me into the office to tell me I wasn't supposed to be dating a CIT. I don't remember if we did much after that but I was a changed man. In the second session of the camp after she was gone I kissed the most sought after girl at the camp, a total barbie, the Pickle was now a stud.

When we returned to Toronto we tried to continue our relationship but our gigantic differences really started to show. She was a rich North Toronto girl who went to a waspy jock school and I was an artsy from North York. She broke up with me not too long after. I told her I had lost my virginity to her but that failed to impress, I suppose she will always be a lot more special to me than I am to her.


i'm 20 years old and i've been fat my whole life, no girls ever wanted me. i turn vegetarian and then vegan and i'm thousands of miles away from home, in fucking vancouver. all of the sudden i'm skinny. this girl gets a job where i work. everyone says i should get with her because she wears a lot of black, like me, like we're some fucking addams family match made in heaven. i'm like "naaahhh" thing i know a couple months later i'm finger banging her on the beach in the rain. i'm 21 by then. we go to her place and i never ate pussy before before but here goes. i say some gay shit like "you taste beautiful". whatever guy it was my first time, i'll fuckin kill you. she tells me years later she thought i was a fag cause i couldn't get it up [it was the condom] the very first time we tried, but she also said it was the best head she's ever had [yesguy]. i never put on a condom before. we fuck without one cause she says she's clean, and she is. we spend three days in her room fucking, sleeping, talking and not eating. i get sick. she gets sick. things got pretty fucking dark after that and lasted a couple years. all in all i wish i'd lost my virginity to emma bell from grade ten latin and never went to vancouver in the first fucking place.