5. "I lay back in the hammock and he carefully climbed on top of me..."

Female • 17 years old • Rio Grande Valley, TX

I'd always been eager to learn about sex. I was snatching my mother's romance novels at ten and reading them cover to cover in the bathroom. I'd snoop in my older brother's porn collection and shudder with revulsion at the overly large breasts and creepy, staring, eye-like nipples. I used to imagine that the gigantic breasts were some sort of extra bladder for pee. (I know, I was a weird kid.)

As I got older, I would read Cosmo and Glamour to learn "88 ways to blow his mind," look up words like "coitus" and "clitoris" in the medical dictionary on my dad's shelf, and sneak hurried glances at the naked women in the public-pool locker room. By senior year of high school, I was known for my sweet face and dirty sense of humor. Through all my research, I'd amassed a lot of sexual knowledge without any real experience. With two kisses from two different guys, one boob touch, and half a blowjob, I was basically all talk, no walk. I would joke that I planned on selling my virginity on eBay and retiring at nineteen, but really I was just hoping I wouldn't graduate a virgin.

I started dating my boyfriend early second semester of twelfth grade. He had considerably more sexual experience than I did, but I wasn't worried. I knew everything there was to know, right? Thanks to our almost instantaneous emotional connection (high school is good at creating those kinds of relationships) and crazy chemistry, we progressed quickly from making out, to boob grabs, to handjobs, to blowjobs, to manual stimulation of my nether-regions. We had to be careful not to get caught, so much of our time "watching TV" in the den with the lights out, or "talking" outside after dark was really put towards our sexy checklist.

Illustration by Thomas Pitilli

After two months of dating, and a ton of research on my part (brands of condoms, the effectiveness of the "pull-out" method, careful observation of my cervical mucus for clues to my ovulation cycle, and the effects of low BMI on fertility), I felt suitably prepared to relinquish my V-card. First, we started off with little "experiments" — just casual, introductory, "Hi, I'm a penis" meetings with my vagina. These would take place on my family's trampoline in the backyard, in the dark. About an inch would go in and we'd pause to see how we both felt, and then go another inch in. This would continue until I would hiss with pain and smack him on the arm to "pull out, you dummy!" He was a cut seven-and-a-half inches, so we'd make it about half-way in.

I never worried about breaking my hymen because I had actually accomplished that in the first grade by falling out of a tree. I just wanted to make sure my vagina would be receptive to the whole "penetration process." I'd heard awful stories of women experiencing unimaginable pain during intercourse, women who bled for ten minutes straight, women whose lovers found "growths" or "lumps" in their vaginas that turned out to be undescended testicles. All of this was "totally true" and happened to "my friend's cousin's massage therapist's niece's bunk-buddy at church camp, I swear!" but eh, I was naive and paranoid, so I proceeded cautiously.

When we finally did the deed, we did it in the big, green hammock on my patio, next to my dad's jasmine vines. It was one of those stand-alone hammocks — no trees necessary! — and surprisingly sturdy. My siblings were all asleep inside, and my mom had dozed off in front of the TV earlier. I'd changed into a short gray skirt (for easy access) and crazy-patterned knee-socks (for fun). He wore regular clothes and threw his belt into the grass. The condom? Trojan, Twisted Pleasure. I lay back in the hammock and he carefully climbed on top of me. I took deep breaths of the jasmine-scented air and tried not to be nervous. I could see the moon over his shoulder and I remember thinking, "This is right. I'm glad I waited."

I helped him put on the condom (being sure to pinch the tip), and kissed him over and over again. With my hand guiding him in, we finally had real, complete sexual intercourse. The hammock swayed with his thrusts, making me dizzy, but I got used to it. It started to feel really nice, like a foot-rub for my vagina. I didn't come that night, because I wasn't quite sure how to come from intercourse. I understood the dynamics of clitoral stimulation, but I wasn't sure how I could get a hand in with him on top of me.

Afterwards, we declared it a success. I was no longer a virgin! I felt a little regretful, mostly because I had a residual childhood belief that unicorns existed and only appeared to virginal maidens. (I told you I was a weird kid.) But I'm still with that boyfriend and we're very happy together. I can totally come from intercourse like a pro. A moonlit night in spring, in a hammock, with a guy I loved? I think my first time was perfect.

NEXT: "I was fifteen and fighting with every ounce of my power not to be gay..."