I was a virgin until 20 because I wanted to wait until I found “true love.” In retrospect, I realize this meant a steady date for a month.
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Phil
I was a virgin until 20 because I wanted to wait until I found “true love.” In retrospect, I realize this meant a steady date for a month. Phil and I went to the movies, held hands, and talked about Jack Kerouac for a few weeks, which seemed love-like enough to warrant sex. We were the same age, but he was open about his fetish for older women. I pretended to be his high school algebra teacher Mrs. Fink and he’d yammer on about being “the shy kid in the back of the class who can ram that 40-year-old pussy.” It really turned me on, and as I type this realize it still kind of does.
Adam
I was desperately in love with Adam, a misguided DJ of sorts, but he very obviously had the hots for my college roommate. This kind of rejection catered to my shaky self-esteem and my attraction mushroomed into obsession. I’ve always been slight and he made no secret about his love for larger women. When we got naked, he told me I could stand to put on a few pounds and we fucked. He came very quickly in the doggy style position and soon got back together with his Rubenesque ex.
Richard
Richard was the kind of nerdy smart guy I want to marry someday. I can say with sincerity that I don’t think anyone has ever loved me so deeply. Unfortunately, I was young, frivolous, and distracted by more flashy suitors. I broke his heart as carelessly as a wine glass that year and I sometimes still read our break-up letters and get weepy. The sex was vanilla, but he was the first to make me orgasm and the first to look into my eyes while doing so.
Dan
Dan was a tall, gorgeous, born-again Christian hipster. He wore his hair as ironically as he did his morals. He went to church, hoovered up mountains of cocaine, and drank like a fish. He had a sexual history littered with escorts but scolded me for being okay with abortion and gay marriage. He was saved as BDD (“Big Dick Dan”) in my phone. I think he’s married to some frumpy Christian chick now.
Eric
When I moved to New York City, I was broke, scared, and depressed. I met Eric at a magazine internship and while his looks made me want to dry heave, we bonded over music journalism and embarked on a steady, sweet relationship that spanned the better part of two years. The sex got off to a rocky start, though. After a few disastrous attempts, he explained away his erectile dysfunction to anti-depressants. It was a good two months before I could get him to maintain an erection long enough to count as actual sex. To this day, he’s the only guy I’ve ever fallen for that was also my best friend.
The roommate
After my split from Eric, I embarked on what I like to call The Manic High of 2007- 2009 and boy was that a laugher and a screamer. I made the very wise decision to move in with a hot single guy who liked to walk around in his boxers, grab my ass, and invite me into his room for back rubs and bong hits. Within 30 days, we were having aggressive, hair-pulling sex and by day 45, I felt like one half of a married couple who enter therapy to gripe about the dishes. I lived in that apartment for three years and we proceeded to have scattered, random sex that was often before or after an argument about the cable bill or toilet paper. I don’t recommend sleeping with your roommate.
David
David was good-looking, successful, and lived in an immaculate apartment. At some point on our third date, he revealed a love of wearing women’s underwear and after a few tumblers of Scotch: “I like to give guys head, but I’m not, like, really bisexual.” One night after dinner he wanted to wear my thong and asked me to write dirty phrases on his ass during sex. “I want filthy,” he said, and I, of course, obliged. One of our last sexual encounters was a particularly embarrassing attempt at organizing an ill-fated sex party, which resulted in David and I being the only ones naked.
The Male Model
Girl meets boy. Boy takes off shirt and girl marvels at boy’s abs. Girl finds out boy is an aspiring model. Girl fucks boy repeatedly, and is left sweaty, sore, satisfied, and suspicious.
The Go Go Boy
I got laid off from a dream job and sought refuge with my best gay friend at a kicky little East Village gay bar called The Cock. Four vodkas later I’m making small talk with a particularly buff guy in a green speedo and combat boots gyrating on the bar. Three shots of Jameson and we’re in a cab back to my place. Two things are for certain: one, I will never forget my first time getting anal and two, I couldn’t pick that guy out of a line-up to save my fucking life.
Willis
I went through a period where I was letting “photographers” take naked pictures of me for cash. I was unemployed and needed to make a quick grand. Willis was handsome with kind eyes and standard point and shoot camera. After our first “session” he asked if he could fuck me for double the asking the price. I went for it. Uneventful but economically prosperous. That being said, I severed our working relationship after the first encounter. It made me feel scroungy.
Greg
I decided to try my hand at online dating and the OKCupid gods produced Greg. He was an Ivy League educated filmmaker who always acted a little jittery. While cute as a button, our sex life hit a snag when he confessed to a severe penis chaffing from a marathon masturbation session. We didn’t have sex that evening and I asked no further questions. I think we just phased each other out, but I still read his Twitter feed.
Facebook Boy
I’d known Bryan since I was 12 and after he friended me on Facebook we started shooting each other flirty messages. The holidays were nigh and we decided to meet at a hotel in our hometown to get to know each other a bit better. He was wholesome and intelligent, the kind who has an organized portfolio of stock investments, watches Dancing with the Stars, and owns napkin holders. Amazing sex and probably the only time I pictured getting married, having babies, and adopting a golden retriever with a one-night stand. We still text sometimes.
The Doctor
There comes a time in every girl’s life where she wipes away the vodka dribbles and tells herself to find something responsible. I was in this period when I met The Doctor. He was 41, I was 27. He told me I “looked good” for my age. I soon learned all of his exes were getting Barbies for Christmas while he was in medical school. Thankfully, the sex was good because the conversation was not. When I could no longer stomach his roaming eyes and juvenile jokes, I told him I wanted to get married and have children within the next year. That did the trick.
Alexander
Hands down the best sex of my life. Alexander was mop-headed and artsy, I was sleek and analytical. I dreamed of writing a book, he barely owned one. Oil and water, light and dark, positive and negative — we were opposite forces; matters so repellent they attracted. I can still smell the Sundays where we’d fuck, eat breakfast, and return to bed until sunset. We stayed together for over a year, drank way too much wine, and talked about “being in love forever.” It worked until it didn’t anymore.
Donovan
I met Donovan after Alexander and I split, which was a particularly low period of my life. Most of my energy was devoted to getting out of bed, going to work, and coming home. I was pretty much spent after that and boy did he let me know how much I sucked in bed. He accused me of being “mechanical,” “not at all sensual,” and “boring.”
James
James is tall, dark, and handsome with a love for words and music. While lying in his bed I’d toy with the idea of asking him to a museum or a poetry reading. I wanted to sit around, drink espresso, and talk about Van Gogh with him. Alas, the relationship hit a roadblock at a quaint Italian eatery when he told me about his disdain for monogamy and love for our waitress. He liked to scream during orgasm. I still have sex with him sometimes.
Sammy
Sammy is a very good male friend and one night after too many beers we ended up in bed. This was over two years ago and he still sexts me late night, every week or so. I try to ignore them, and every three months I re-break the news that we are never, ever, ever under any circumstances going to have sex again. He forgets this every time.
Anton
I met Anton at a party and thought he looked a little like Alexander, which automatically set my mind into a kind of frothy, sexual autopilot. Without learning much more than the fact he’s Russian and has a Henry Miller book in his bag, I decided he was coming home with me ‑ this equal parts flattered and confused him. Shortest sex I’ve ever had in my life.
Jonathon
One should never enter first dates so horny they’d dry hump a lamppost. When one is so horny they could fetishize a bar stool, they certainly should not order that fifth drink. And once the fifth drink is consumed, under no circumstances should the date be invited upstairs. But who knows, maybe he’ll call.
