When first emerging out of a very late puberty, there’s nothing better than having every type of crazy, wild, random sex you can imagine. Beach-chair blowjobs in Costa Rica, nightclub orgies in Cancun, a handjob from my cousin’s friend in Central Jersey — for me, any fantasy was possible. I could construct the exact sex life I wanted, down to the whipped cream and barbecue skewers. Sure, I was a neurotic, short virgin who gravitated to the friend zone, but no one had to know that — as long as I could make my fantastic sexual encounters sound convincing.
My fantasies sparked after my sophomore year of high school, when my best friend defeated me in our mutual pursuit of a busty, freckled junior; we were hypnotized by her cleavage and ignored her screams of delight upon any mention of My Chemical Romance. A few months later, we both fell in love with the same literary lesbian, but he was the one who got to enjoy a conversational, repressed romance with her. On my many dateless nights I watched a lot of teen movies, and I was quickly identifying myself as the fall guy — known in scholarly teen-movie circles as “The Baxter.” Not that I’d ever admit this to my friends.
Instead, my elaborate lies seemed to work. But as I approached the end of high school, I still resisted lying to my friends that I had lost my virginity. I felt comfortable telling my soon-to-be college roommate that a girl had just lathered my dick with AstroGlide while we watched a Hugh Grant marathon (this act was, sadly, actually executed by my left hand), but I couldn’t imagine the kind of fictional character that could take my virginity. My friends would really dig deep to investigate, and I was afraid I would crack under the pressure and scrutiny.
The answer for me emerged, as it does for many virgins, with the coming of prom.
I asked my crush to go with me, but she already had a date with the dude that sold steroids out of his locker, so I went home, filled a half-empty 46-oz. QuickChek Coke with Bacardi, and IM-ed a girl I’d met at a college’s admitted students day.
Her name was Rori, and we “picnicked” on a south Jersey dock. The fried chicken soon turned cold and soggy. She kissed me, which I’d done with real girls before, so I felt reasonably comfortable. Soon, though, she led my hands under her skirt. My hands began to shake. These things were far less frightening in my imagination. But to my utter surprise, my quivering fingers soon gave her an orgasm (or so she claimed). I repeated the act in the back of my Camry in a dark, abandoned lot, delaying the prospect of having to do anything more. Then she said she wanted to fuck me. I asked for a blowjob instead, a terrified tremor reverberating in my voice. Her mouth was gaping; it turned her otherwise pretty face grotesque and frightening, and I never wanted to see her again.
The next night I got very drunk at a party and announced to all of my friends that I had lost my virginity. Yeah, I got all in there, with you know, my penis. The vodka tonic strengthened my resolve. Fuck it, I figured, Rori actually existed and graduation was only two weeks away. If I didn’t act now, everyone would think that I left for college a virgin.
My friends surprisingly accepted this story, and I counted the days until I’d arrive at college, where my fantasy world really would have the opportunity to flourish. My high-school past would become boundary-less and malleable. It would have all the fun of shaping a penis out of clay, except that penis was my penis, and in my retellings, I could put it anywhere I wanted.
Two months into college, I was still really enjoying soaking in my fantasy world, but a problem had arisen in the form of my new girlfriend, Hadley, lying naked on her dorm room bed, very ready for us to have sex for the first time. All right Joe, you’ve done this before, I thought — but then I remembered that I hadn’t.
I was faced with my almost-certain sexual incompetence, the womb-like paradise of my fantasy world traded for the colossal hole I’d dug for myself with Hadley. In the weeks I’d known her, I’d drank a few too many water bottles full of gin and tonic and made myself out to be a James Van Der Beek/Freddie Prinze, Jr. hybrid, with a charming alcohol problem thrown-in. So she dumped her clingy, virgin boyfriend for big, bad me. And now she was posed for her teen-movie moment, and I was sure to deliver a Jason Biggs-esque performance.
I announced I had to take a piss. In the bathroom, I stood dumbly over the toilet at half-mast while a terrifying future flashed before my eyes. She was my romantic ideal — literary, dark-haired, olive-skinned, curvy, a drinker, a pot smoker, a pun maker, beautiful, and culturally Jewish — and I was going to lose her. You know, I know, everyone knows guys are awful their first time. She’d take custody of all of our fun friends with drug connections and tell everyone I couldn’t even put on a condom. Not only would my real world be demolished, but my fantasy world would be, too. Even if I transferred to a new school, I couldn’t ever create a better fictional girlfriend than her. My imagination would be permanently scarred. I’d be left cold and alone and have to become one of those kids who draws their own anime cartoons and masturbates onto his finished product. That’s what my fantasy world would come to, and to make matters worse, I’m a terrible artist.
I walked back into her room. We started kissing. She touched my penis; it was scared but excited. I stared at her nipples and fingered her lazily and tried to remember which fucking way you unroll a condom. I had no idea. She grabbed a Trojan from her desk drawer.
“It’s sexier when you put it on me,” I purred. She unrolled the wrong way. I insisted that she keep trying.
“Practice makes perfect!” I sounded disturbingly like my nana.
My stoned roommate had lectured me for hours on the merits of lube, so I had begun carrying Astroglide in my bag. I hoped having sexual aids would give me an air of authority on the matter, like a doctor casually whipping out a tongue depressor on a house call. Hadley looked confused, but I insisted “trust me, you’ll love it,” before emptying half the bottle over my dick and drenching her sheets. The reality was a lot moister than any of my fantasies. I moved over her. My arms were shaking ferociously, which made it nearly impossible to hold myself up. I tried to think of what fantasy-world Joe would do, and in the process, I got her thigh sticky for about ten seconds. Then, I actually found myself inside her. I did the only thing I could remember from the Kama Sutra and put her legs over my shoulders. I tried to keep a steady motion, like I was at the gym, which was strange because you usually don’t kiss and caress your exercise machine. She began to moan and arch her back, and I prayed to Ernest Hemingway, F. Scott Fitzgerald, and Bret Easton Ellis that she was going to orgasm and wasn’t just having a very strange seizure. And then she came! (I think.) And I came! (I know.) Good God, this is what people made such a fuss about — there was more to sex than just telling stories that impressed people and boosted your ego. I clumsily tied off the condom, flipped it in the trash, and we cuddled.
I’d love to say that immediately after this I realized the error of my ways — that no one was really impressed by my half-baked tales; that continuing to lie to Hadley about my past would be inevitably destructive; that to my real friends, the true romantic failures of my high-school days would ultimately be more appealing than unabashed conquest. Not true at all. For the next two years, I relished having both my wonderful romantic present and my fictional past. Eventually, I admitted the truth to Hadley, because my stories lacked the necessary specifics and consistency to endure two years of intimate conversation. But still, my fantasy world continues to exist in the minds of many, those brave boys and girls that endured my awful, cocky stories at high school keggers and college cross-dressing parties. But as I publish this essay and post the link on Facebook, my fantasy world dies and can never be resurrected.
And it’s better that way. With my self-esteem secure and Hadley loving the real me, I’m ready to regale my friends with genuine tales: the early years where I get caught masturbating with my mom’s Herbal Essence Conditioner, then the failed kisses and crushes, and the drunken, mistake-ridden nights where I never ended up with the girl at the end. But finally, the college girl came along, and somehow I didn’t sabotage myself. Now, finally, everything feels good enough to tell the truth.
This article originally appeared in Hooksexup’s True Stories.
