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Age when it happend: 17
Where it happened: back of my van
Langauge: English
Sex: Female
Rating: 10
Category: Straight

So, it was kind of an accident, actually. Over the previous year, I have had a number of boyfriends and have gotten reasonably far with two. This included mostly just fingering, oral, etc. But I hadn’t actually “gone the whole way”. Every time I would be on the verge of entering a sexual relationship, the relationship would fail and I would be left in the dust. The frustration building up inside of me began to get unbearable when I was dating a boy a year younger than me who has never actually even kissed a girl before me.
I don’t view myself as unusally premiscuous, but beeing nearly 18, I wasn’t really looking for any serious. In that relationship, it felt like I was pushing but he wasn’t pushing back so I decided to just give up and break up with him.
As I was considering how to go about doing this, I asked the first boy I encountered (who happened to be a Kiwi exchange student I had met a week earlier) how one breaks up with a boy (mind you this conversation was over IM).
I really had no intention of him taking this the way he did, but I didn’t realize until it was too late. But he asked me why I was breaking up with my boyfriend so I reflected to him my frustrations. He then asked, “So you’re looking for a steamy relationship.” Jokingly I replied, “More of the steam, less of the relationship.”
To which he responded, “Well the rules of the exchange program said I’m not supposed to be in a ‘relationship’.” I, being a former exchange student myself and perfectly aware of the ridiculous Rotary rules, continued to joke with him about the loophole of ‘sex’ not being included in the ‘serious relationship’ category.
Suddenly, he asked me when we should meet and I kind of… cocked my head, confused for a second before I realized that I had accidentally just implied to him I was interested in having sex with him.
I’m going to continue to insist that I’m no slut, no matter how little you’ll want to believe it. But, I did agree to meet him a few days later. He had sort of just wanted to get right to it, but, me, feeling uncomfortable with that topic convinced him to at least hang out with me for a little while before we made out or anything. After a few hours, we drove back to around where his house was and he told me we should stop somewhere and makeout. His forwardness would have surprised me in any other situation, but I ws getting so desperate, it only intrigued me.
So we found an empty parking lot (which happened to be his school… Yeah, I know..) and started making out agressively in the back steet of my mini van (glamorous, eh?).
When he asked me to “go all the way”, I just said sure, as I knew from the start that was the only reason I was really even meeting him that day. So we did and it was nice… except for the fact it took him about an hour to get hard enough to enter (he blamed it on the condom… ha!) and I was a a bit tight I suppose. I could tell he thought it was all his fault and was probably pretty embarassed. It hurt a little bit, but it simultaneously felt good. I don’t think he had to break my hymen as it has probably been broken for some time (tampons, sports, etc.) so I didn’t bleed or anything.

We did it twice until the condom came loose, then we just fooled around a bit longer. I was tired and wanted to bring him home (as in to his house, you poor one track minded people), but he just kept at it. Eventually I brought him home, with lots of kissing involved, and drove back to my house. I only saw him once after that. And he kept attempting to contact me. And although I had reasonably little interest in him as a person, I wouldn’t have minded seeing him again.
But before that could happen, there was some more romantic craziness in my life (somehow I ended up with two [serious] boyfriends at the same night… in fact kissed both of them for the first time in the same park within 30 minutes of each other).
Yep, you’re probably thinking about what a whore I am… sleeping with men just for the sake of it. But I swear, were you in my situation, you would have done the same! It was all completely a big ironic accident. I would explain, but it would take me hours, so I’ll leave my tale of unexpected confessions and necessary outcomes to your imagination.
One of my boyfriends asked me later if I regretted that I lost my virginity essentially out of spite. I told him no. I guess, I don’t equate sex to emotional connections, usually. Although, I do feel that once you can unite the two (as I eventually did) its far more rewarding of an experience. (I still don’t miss my virginity nor so I regret how I lost it. I know it meant nothing.)

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