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My First Time
Female • 16 years old • Woods behind Papa Playground
I had been with my boyfriend for four months when I started to feel trickles of panic; we were growing distant from each other and I was desperate for us to stay together. His name was Michael and he lived pretty far from me, on the other side of the city. He was always the one to come and visit me at least once every couple of weeks. It was during one of these weekends that I brought him to meet my friends.
When it was about time for Michael to leave, I put on my best pout and shuffled my feet, and my friend Dan and I walked him to the bus stop. When he asked what was wrong, I told him I felt we hadn't gotten to spend any alone time together. He understood the emphasis on "alone" and offered to make a detour through Papa Playground.
![]() Illustration by Thomas Pitilli |
Michael and I had spent plenty of time in the woods behind Papa Playground, making out and practicing manipulating our clothes to get to the goods without exposing too much flesh to the winter wind. Today however, I felt a different type of apprehension when we left Dan behind to wait for us at the edge of the woods. Inside the woods we started our routine of kissing and fondling, stopping at third base. But this time, when Michael begged to go all the way, I surprised him by agreeing.
It was the most awkward encounter I've ever had, doubled over with my jeans pulled down enough to expose my behind, holding Michael's calves behind me as he banged unapologetically hard into me. I was screaming with the mix of pleasure and pain — pain, mostly — and when we were done, I walked back to meet Dan stony-faced and not at all happy with my decision.
Later on, while walking back home with Dan, as I looked at the mud stains left on the bottom of my jeans, Dan said he'd heard me screaming and yelling, and that he saw a guy parked across the street in his car looking into the woods fixedly and eating a bag of chips. So apparently my first (and worst) time was spent entertaining some pervert with a free show. Perfect.
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Commentarium (10 Comments)
Great story and 100% believable in my opinion.
While I am glad that nerve is finally candidly cataloging the ways of this hateful practice we commonly call heterosexuality, I can't help but always be really disturbed by these stories. It's like the women expect it to suck but for some inane reason always go with it and then men are just assholes. Even weirder is that this is REAL LIFE.
@AT
Losing one's virginity sucks, period and teenagers are selfish. I understand your point but I assure you, losing your virginity as a homo isn't any better, self-assuring, pure, gentle, etc., etc. No need to bring orientation politics into venues where they're irrelevant. People are introduced to sex the same way they're introduced to all illicit things as adolescents: someone with more experience/recklessness foisting it upon them. Blame our society which naively asserts that sex among teenagers "shouldn't" happen, despite the fact that it does and will in perpetuity.
Poor poor girl...
Poor Dan.
Sexual orientation is not irrelevant. Have you ever read Adrienne Rich's Compulsory Heterosexuality? It's mind-boggling awesome.
But I do agree that better sex education is urgently needed.(and maybe less pornography that is degrading to women<-- redundant, ain't it?)
wow this sounds exactly like MY first time. what a coincidence hmm???
The comments about every story being sad make me want to post mine, but I'm not ready to do that just yet. But it is an unfortunate fact that I know, at least among my friends, I might be the only woman who didn't feel any remorse after my first time.
AT, I want to point out that pornography isn't degrading to men or women (yes, men are in porn as well). They do it because they want to. It's their choice. If you think ill of them for doing it, then it's you who is degrading. This is my first and last time on this site, so I won't see any replies to this. I just wanted to make that point.
@ AT
Not all of these stories are disturbing. I wouldn't even use that word to describe most of them. Some of these stories are actually positive and could appear in romance movies. It's not fair to stereotype women as going along with it and men being assholes in every "first time" experience. I have not yet had sex, but I am in a loving relationship with my boyfriend of two years. We talk about having sex, but neither of us is pressuring the other and we've talked about the problems that can occur during your first time having sex. We both understand it might be a little uncomfortable, but I know for a fact that he wants our first time to be just as much about me as it is about him. Please understand that this is not always real life; there are heterosexuals who have positive experiences of first-time sex. They are here, and it's not hard to find them.