Going one (two, actually) better than Dean and Chellee, I hereby present 3 versions of how I lost my virginity. Only one is true; the others are partly true, and could have happened. It's up to you to decide which is which.
1. I'd known M since Grade 5, and we hung out with the same crowd (the smart band geeks). He’d been dating another girl in our grade off and on throughout most of high school - they broke up every couple of months or so then reconciled within a week for about 4 years. Their fights were famous, and frequent. He was very smart, very funny, and a great dancer. And short - if I wore flat heels, we were the same height.
M & I were at a party together a couple of months before graduation, during one of their 'off' periods, watching horror movies. We were sitting together on the sofa during, as I recall, Cat People with Nastassja Kinski, and I hid my face against his shoulder in one scene - not because I was particularly scared, but because it seemed like a good idea at the time. He put his arm around me, and before the end of the movie we were kissing tentatively (well, I was tentative anyhow). We didn't really date - our group didn't do formal dates - but we started hanging out together after school (he had a car and could be relied on for rides home). My mom was friends with his mom and therefore quite delighted that there was 'something' between us. I think she had us engaged and married off within a couple of weeks.
What she didn't know was that M had a well-deserved reputation for horniness and spent most of his time trying to get his hands in my pants. All my friends were sleeping with their boyfriends and as the only virgin in the group, I was more than a little curious about what I was missing. M was certainly experienced, as well as enthusiastic and persuasive, and he was a good friend so I figured I could certainly do worse for my first time. All that was lacking was the opportunity - his mom ran a daycare in their house and he had both older and younger siblings who delighted in thwarting his plans, so his place was out. His aged Audi was not particularly conducive to romance - or even plain old sex (I'd heard stories from his girlfriend). And my parents, although they trusted me to a remarkable degree, didn't go out much in the evenings, and invariably left me in charge of my brother and sister when they did. Eventually, we decided to skip school one afternoon and do the deed in my bed while my parents were at work. M would have had sex in the middle of the field at school, during a soccer game, given the opportunity, but I wanted somewhere a little more private (and comfortable) for my first time.
We'd been doing some hot-n-heavy petting for a few weeks and M was ready to go before the front door was locked behind us. We did make it to my bedroom, shedding clothes as we went, and I'd grabbed a towel on the way down the hall (dark coloured - as a voracious reader I knew what to expect). I will say this for him - M knew what he was doing (he'd brought condoms, too). No fumbling around, no misfires ... not a lot of pain, either. A little discomfort, then it was over. We had another go a while later, and a few more trysts over the next month or so, but there was never really any romance between us and sex didn't do a lot for me, so things kind of fizzled out. Eventually he went back to his off-again-on-again girlfriend, who never found out about us, and I found a more conventional boyfriend. We remained good friends for years, although he continued to hit on me whenever we were alone right up to the last time I saw him, 3 or 4 years ago (long after we were both married and had children).
2. D. was in my Grade 12 English class, and kept showing up wherever I was - in the library, waiting for the bus (although he lived in the other direction), at the drycleaners where I worked on Friday nights ... I was completely oblivious to the fact that he was intently pursuing me. He asked me out for the first time a few weeks before grad, and we started hanging out together more and more over the summer. He was an odd guy - not in a bad way, but a defiant loner who secretly resented people who fit in. I was flattered by the attention, although in hindsight it might have been a bit obsessive. Looking back, I think I fell in love less with him than with the idea of falling in love, but at the time I believed it was the real thing.
He didn't drive, and my parents weren't all that keen on him so didn't offer their car as often as I would have liked, which limited the amount of time we spent together. He lived with his single mother, and we most of our dates making out in his basement, although I don't recall him pressuring me to go all the way very often. We watched Spaceship Yamato and he introduced me to Dungeons & Dragons.
After 6 months or so, I decided the time was right to go all the way, and went to the student clinic at the university to get a prescription for the Pill. I told him, that night, that we could start having sex in a month - I think he was a little surprised as we hadn't talked about it first. Not disappointed, of course - he was a normal, hot-blooded 19-year-old, after all. 28 days later, I had my dad's Buick Skylark, and we headed for a secluded area (one advantage to growing up in North Vancouver – lots of wooded, out of the way places to park). The back seat was too small, so we reclined the front seat all the way and started fumbling. It was the first time for both of us, and it took a while to figure out what went where, especially since we couldn't see what we were doing and weren’t willing to get completely naked (it was, as I recall, December). Eventually we got ourselves aligned, and he started thrusting. I remember a short, sharp pain, followed by a sort of abraded irritation every time he moved (which, mercifully, didn't last long). It took me longer to get the blood out of the upholstery than it did to complete the act.
After that, we had sex a couple of times a week, either in the car or in his basement when his mother was out, but I never really enjoyed it. But everyone was doing it, and I didn't have the courage to ask any of my girlfriends about their experiences. The following year, I started getting migraines, and my doctor took me off the pill, which I used as an excuse to stop sleeping with D. He settled for regular hand- and blow-jobs, but I started to resent the one-sidedness of it. We went out for another 3 or 4 months, mostly because my parents were pressuring me to break up with him and therefore I couldn't (my one act of teen rebellion - dating a marginally unacceptable guy for an extra few months).
He never spoke to me again, and I haven't heard anything about him in probably 15 years.
3. T was the drum major for the community band I played in. The usual rule was that you had to quit the band when you graduated, but that summer we were touring Germany for a month, so some of the older members stayed on. He was in first year university when I was in Grade 11, a tall, skinny blond with glasses. He was into punk rock and cynicism, which made him seem very worldly to my naive eyes. He was also quite bright and articulate, with a fondness for quoting Monty Python, and I'd developed a mild crush on him. But I wasn't one of the 'in' girls in the band, so we didn't have much to do with each other despite spending 5 or 6 hours a day on the same bus.
One evening, at a youth hostel in the Black Forest, a bunch of us were sitting on the stairs talking. He sat a few steps below me, with his shirt off, and was complaining about how sore his shoulder was from carrying the mace in a parade earlier that day. I don't know where I found the courage, but I offered to rub his back for him. My mother suffered (still does, actually) from tension headaches and at 16 I was quite an accomplished masseuse. We started talking, and the next day he invited me to sit at The Back Of The Bus, uncontested domain of the cool kids. There were some black looks from the other girls, none of whom had been successful in attracting his attention, but it didn't take them long decide to make the best of it, and I became one of their clique. For the first time in my life, I was part of the Inner Circle.
One night, returning to our hostel after a late concert, we started kissing - my first kiss. I remember how totally surprised I was when he slipped his tongue into my mouth. We were pretty heavily chaperoned, and I think he realized how inexperienced I was (it must have been pretty bloody obvious), so we didn't go beyond kissing until the trip was over.
My mother, never having been a band member, was prepared to trust, unconditionally, anyone in the band. She was a little worried about the 2-year age difference, but T was unfailingly polite and respectful of authority around said authority, and she relaxed her guard pretty quickly. It helped that we usually went out in a group - she didn't have to know that we didn't stay with the group. T fancied himself a modern renaissance man, wrote poems for me, and was very gentle, never pressuring me to sleep with him even though I know his friends gave him a hard time about it. He also worried a lot about the vast (2-year) difference in our ages. I was totally smitten (and more than a little curious), so when we had a chance to spend a weekend alone at his parents' place in Whistler, I was willing and eager. I told my parents there were a bunch of us going skiing for the weekend, and off we went.
We took our time, T wanting to make sure I was still OK with the whole thing – I think taking my maidenhead was a bigger deal for him than for me. I just wanted to get it over with, to see what the big deal was. We made out for a long time, gradually shedding clothes and inhibitions. It hurt a little, less than I’d feared, and T stopped to make sure I was all right. No fireworks, even when we tried again the next morning. And fairly regularly after that. T was the youngest in his family, and often had the house to himself. We used condoms for a while, until my fear of one breaking overcame my fear of ‘fessing up to my family doctor and I went on the Pill.
We broke up after I started university. I was carpooling with a bunch of engineering students, who were always looking for females to grace their dances and beer gardens. T was jealous of the time I spent with them, and I wasn’t willing to give up life on campus for him.
He moved to Africa after graduating, where he met and married an Irish lass. The last I heard, they were living together in Ireland.