How to Pop a Cherry

If I ever have a daughter, I’m going to advise her to wait as long as she can to lose her virginity (OK, until she’s eighteen or something; I don’t want her to be a thirty-year-old virgin loser). It wouldn’t be for any puritanical reason, but simply because I lost mine when I was sixteen, and I was definitely too emotionally stupid to understand that “having sex” was a relatively unimportant signifier in the scheme of everything that would happen to me in my life. As such, I made an incredibly huge deal out of the first time I got laid.

My first “serious” boyfriend was a boy called Vinni, who went to the Catholic boy’s school near mine. He was gorgeous; born to an Indian father and an Italian mother, his skin was perennially tan, his eyes dark and almond shaped, and his tips frosted. He wore an earring like a rapper and had a samurai sword hanging over his bed, along with a series of mint condition vintage Star Wars figurines. He taught me how to play Diablo II, and, possibly oxymoronically, everything I knew about sex.

Vinni was two years older than me, so when I was sixteen and he was eighteen, he’d pick me up from school in his car, which would make everyone whisper as I walked down the hill we’d wait on for the bus or our parents to collect us. He’d buy me cigarettes and alcohol, and on Fridays, we’d drive out to the McDonalds near the airport and buy a chocolate sundae and an order of large fries each, then we’d park behind the fence where the planes come closest to the ground before they land on the runway. We’d sit on the hood of his car and dip our fries into our sundaes, and with mouths full of chocolate deep fried potatoes, we’d throw tennis balls, which would never actually make contact, at the bellies of the planes.

I fell in love. It was a time when I wasn’t particularly popular at school, and even though Vinni dragged me to the midnight premier of Star Wars Episode II, where there were people dressed as Jedis, fighting with light sabres in the aisles of the theatre, he was cool. He listened to Ministry of Sound compilations and had a nipple piercing and a giant cross tattooed across his back like David Beckham. It was the first time in my life, despite being a horny little girl and a curious teen, I’d ever felt that yes, I definitely would like this boy’s penis inside my vagina.

Vinni wasn’t a virgin when we met; he was slightly older than me and frosted tips were hot in the 90s, so he’d had sex with a few girls before me, all of whom were older and sexier than me. I’d troll their photos on a site called Picture Poll (like Facebook, but you could rate everyone’s photos on a scale of one to ten, really great for inspiring self-esteem and altruism) and work myself into a frenzy of insecurities. There was one girl, Krystal, an alleged Playboy bunny and model, who posted photos of herself lying across the hoods of sports cars, that terrified me. In all her photos, her pencil-thin eyebrows (which were all the rage back then) bordered expertly applied eye shadow that graduated from shimmery white to pink to black, and her huge breasts seemed to always be attempting to high five her chin. Vinni had slept with this girl and many others like her. And now, I wanted to sleep with him—an awkward little girl whose limbs were growing out of time with one another (first my legs were too long for the rest of me; then my boobs eclipsed everything else; then suddenly, my arms became apish and too gangly for the rest of me), whose eyebrows still joined up in the middle, who thought it was chic to get fluro pink bands on her braces, and who had a generous smattering of soft but dark brown hair across her lower back.

I was the first obstacle to my planned lovemaking. I was insecure and worried that I wouldn’t be as sexy as the girls he’d slept with before, and at the same time, I’d developed the suffocating notion that having sex wouldn’t mean as much to him as it did to me, because he’d done it before. As a teenager, everything is soaked in meaning this way: the first time is the most important time. What I didn’t know then, which I do know now, is that if you lived your life placing this much import on “firsts” and thereby eliminating the importance of subsequent events, life would probably become entirely meaningless by the age of twenty-five. To this day, I still have sex that is as memorable as that first time, although now, it’s generally memorable for better reasons than “It wouldn’t go in then when it did, I bled everywhere, and locked myself in the bathroom and cried afterwards.”

The first time Vinni and I tried to have sex, I planned everything down to the last pube. Seriously, there were spreadsheets and weeks of scheming; did I mention I was an awkward weirdo? My parents had gone out for the evening, and my mum, not knowing about my deviant plans, helped me cook all afternoon so that Vinni and I could have a romantic dinner at home while she was out of our hair. I made his favorite foods: spaghetti Bolognese and chocolate mousse for dessert, and I laid it out on a card table in the living room with candles and flowers. It was how I imagined American teenagers did it, and for some reason, that felt like the right way.

I had used all my money to buy a black g-string and matching bra, which, at the time, I thought were very chic, although the cheap lacy polyester combo probably shrieked “stripper” and not “high-class escort” like I wanted them to. I wore a stupidly inappropriate dress for hanging out at home, slinky and black with high heels, which I planned to keep on while I was “making love,” dark eye makeup, and a whole bottle of Ralph Lauren “Ralph” perfume. When Vinni finally came over, it was awkward in my head. I wanted to be seductive and alluring and grown up, so that awkwardness translated into prolonged silences and me doing a strange, deep laugh I thought was somehow more sophisticated and womanly than my regular laugh. It was weird. But it got weirder.

After dinner, when it was time for the sex to happen, I moved the action to—wait for it—the floor, in front of an already blazing, open fire. I was going to lose my God damn virginity in front of a fire. At sixteen, I was adamant that my first time having sex would be exactly like the worst, most cheesy teen movie you have ever seen. I guess I thought that when I grew up it would be cool to be able to tell people the first time I had sex was on a rug in front of an open fire, which, I assumed, was what all adults thought was The Most Romantic Thing Ever. But I was terrified. I knew, deep inside my gut, that I was going to do sex wrong, or in the very best-case scenario, I would do it sort of right but it would be painful and awful. My anxiety increased as I lay naked on the carpet in front of the sexy fire, and it was time for the pee-pee to go in my ‘gine-y. My eyes began to fill with tears as he began to stab into my as-yet unpenetrated vagina with something my vagina absolutely did not want to let in.

We tried for about ten minutes. Vagina was not having it; I would not be losing my virginity by this perfect, sexy fire, on this perfect, sexy night. Instead, for the first time in my life, I felt what it was like to be completely naked, physically and emotionally. It was the most vulnerable I’d ever felt, and as I curled my knees to my chest and cried, and Vinni reassured me it was OK and we’d try again another time (because he was lovely and supportive for a teenage boy and in that respect, I was lucky), I knew that “another time” wouldn’t be this perfectly organized, special time, and that however and whenever I had sex for the first time, it would be utterly horrible. Suddenly, sex was no longer the life-giving Holy Grail I assumed it to be; it was more like the duplicitous bejewelled cup the greedy guy drinks out of that turns him to dust. Later, I would learn, of course, that following instincts, rather than a preconceived notion of what sex should look like, could make for beautiful encounters. Like when Indiana Jones took the ugly cup and drank from it and it was the right one.

I’d lose my virginity a few weeks later, in an entirely unglamorous situation. Vinni and I—in my single bed in my childhood bedroom, still covered in soft toys and those plastic, brightly colored gerberas stuffed into vases filling every corner of the room—did it on a whim on another occasion when my parents went out. It hurt like hell, and I cried the entire time because I’m a wimp, but Vinni told me that he loved me and when it was over he stroked my hair. The sheets were covered in blood and Vinni washed them by hand in the bath; he took them outside and hung them on the washing line to dry while I showered and contemplated how I wasn’t a virgin anymore, although I still couldn’t drive. Nothing had really changed, and I was not a smidge closer to being “grown up,” except that now I was someone who put dicks in my vagina; it was that simple, and that profoundly irrelevant to my personhood.

- This is an extract from Kat George's book Pink Bits, which you can get here.