Illustration by Les McClaine

When we asked Mercury readers to submit their tales of losing their virginity—and promised $100 to the person with the best story—we didn't expect to have to read so many gross, sad, and depressing emails. We also thought some girls would submit, but all of the entries came from guys. This proves one of two things: Either girls have way better first-time experiences, or guys have absolutely no shame if there's a remote possibility they might win $100. Without further ado, here are the best three entries.

THIS VAN IS ROCKIN'

My mom bought a giant white Ford Econoline van that summer. It had a TV, mood lighting, and captain's chairs. Really, that van was nicer than the house we lived in.

I had just turned 16, and one night after endlessly driving around in the van with my girlfriend, looking for places to make out, we pulled into an elementary school parking lot. We started making out, and it eventually moved to the back seat, which folded out into a bed.

So I fumble with her bra and she fumbles with my belt, soon we are naked, and three pumps later, I'm lying there naked with a condom on my limp dick full of man gravy, when we see lights flash across the windshield. We freak out, get dressed, and peel out of the parking lot, leaving my innocence behind, never to be seen again.

Three years later, my mom sold the van to a nice Christian family with seven kids. They made small talk with my mom, and then they started inspecting the van. All of the sudden, one of the kids came crashing out of the van with all his brothers and sisters in tow, screaming, "I found a balloon! I found a balloon!" and running in circles around the van, with my used condom in hand. It was an odd moment for all of us.

—Grant Ray Howard

COMING HOME

I am eternally grateful that someone who got around introduced me to the ways of love. I'll refer to her as "Janet," even though her real name is Cheryl.

"Janet" taught me the virtue of "foreplay." In other words, kissing and boob fondling. I discovered that I like to touch boobs and that they are squishy. The pointy part is called the nipple and it gets hard, like a little erection. It's nothing to be afraid of.

Then came the "moment of truth" when finally my thing went inside of her stuff. It felt good, of course. Better then good, but not quite as great as eating pancakes.

Mostly it just felt weird. The weirdest thing was this feeling that when I went inside, I was "coming home," which is weird, because my home is nothing like a vagina. Nobody lives in a vagina.

As I understand it, when a man and woman make love, it's the primary role of the man to not ruin things. In other words, not to prematurely ejaculate. There is no need to go into this problem, however, since "Janet" just rolled over and finished herself off. This was my first experience with a vibrator, even though it was actually her experience of it.

But the coolest thing is that while I was waiting for her to finish, I found a bunch of back issues of Hellboy in her room, including the third issue, which is really hard to get.

Scott Erickson

AN AUDIBLE POP

Sara Rainbow was tall, heavy breasted, long faced, and an outcast. "Unconventional looks," my mother would say. "Horse faced," my friends would snicker. But I set to work on making her mine, and soon enough, she was.

And that's how we ended up in my bedroom, stripped to the waist, those enormous, delightful breasts playing across my pasty chest, the crotches of our blue jeans locked in a frictive crush. That's when it happened.

I should explain: Sara Rainbow was a late bloomer. She hadn't figured out masturbation, knew almost nothing of sexual anatomy, much less of the act itself. After an early makeout session, she called to ask me if I had soaked my pants, because it had gone all the way into her panties. I didn't have the heart to explain. She was so clueless, in fact...

Making her sexy face, and dry humping in earnest, she came down full force on my tented penis. It first shuddered, and then buckled painfully, causing an audible pop of gristle. I stared, open-mouthed at the ceiling, a cry caught in my throat, eyes tearing up. And as my brain flashed to the days that would come—I imagined the bruise, and the lump of scar tissue that still gives a gentle kink—she looked at me through heavy eyes and mouthed, "Did you come?"

Aaron Walker

We can't do anything about that kink, Aaron, but here's hoping your $100 first-place prize helps alleviate some of that pain. Also, for the love of Christ, never tell us that story again.