Losin' It

Losin’ It
It only happens once, it’s usually not all that great, and most of us try to forget about it because it’s kind of embarrassing. That’s why we asked assorted New Yorkers we like and admire to reveal their first time stories, at the risk of losing their respect. Enjoy!
[I helped find interviewees]

MY FIRST TIME • Audrey Ference
I lost it to a guy named Ace. Seriously. That was the name on his birth certificate. I was in college, which I realize is embarrassingly old, but I grew up in Texas and my high school boyfriend was kind of churchy, so we never went all the way.

Ace, who was nominally my boyfriend — I’m not the sort of girl to lose it to a stranger, after all — was visiting me at school. I was at the point where I just wanted to get it over with. I wanted to get past the awkward first few times and get going with the good stuff already. I was in college. I wanted to sleep around.

We were in my roommate’s room. She was out of town, and all the beer was in her fridge. Ace had deflowered a lady before, and suggested that a few beers might make things go more smoothly, hymen-popping-wise.

The plan had been to get the beer, drink the beer, go back to my room, then do it. But once we started drinking the beer, we kind of got wrapped up in making out, and all of a sudden, we were all naked and ready to go.
“We can just wrap up in towels and scoot back to my room,” I said, and opened the door a crack. The hallway was packed with people — my other roommate was having a party. I slammed the door.

“Let’s just get dressed and go back to your room,” he said, pulling on his boxers.

“No,” I said. I was tipsy and naked and I had waited long enough — I didn’t want to lose my nerve. I was tired of being a virgin.

So we did it, right there on her floor. It hurt. I never did tell her.

MY FIRST TIME • Jessica Delfino
Ms. Delfino is a potty-mouthed comedienne often compared to the likes of Redd Foxx, and, well, Redd Foxx. Her recent Youtube smash hit, “My Pussy is Magic,” is very funny.

The loss of my virginity was iced with a layer of criminal mischief and riddled with illegal and immoral dealings, like a bullet-holed car door in some old (sexy) make-out pit.

I was just an eager, measly 14 when a first botched attempt at stealing my virginity was made by a local car vandalizer named Evan. However, my petrified vagina was too tight for him to break and enter into. The kids (literally, the kids) all made fun of me for having a vagina that was too tight. True story! In my small town, I'm lucky it didn't wind up in the police blotter, beside Evan's weekly listing.

The man who actually took it was a statutory gent named Paul, who was 18 to my 14. The handsome man removed me of my needless virginity in my own bed, while my father was out unloading lobster trucks one cold, Maine winter night. I shuddered nervously as Paul clambered around on top of me, and shyly inquired about the weird thing that had happened when I accidentally had my first orgasm, atop my first round of intercourse. Paul must have felt like a real pro. As he pulled away, he noticed the red flag of my innocence. "Are you a virgin?" he asked. I had originally told him I wasn't, feeling like the car-burglar and I had practically "done it.” I then

confessed, that yes, I guess I actually had been a virgin, only moments earlier. A perplexed look came across his face, and he seemed genuinely concerned, but not concerned enough to not bang the hell out of me continuously for the next six months. Our relationship fell apart that summer when his girlfriend came home from college and he had his own confession to make. What a dick!

MY FIRST TIME • Molly Crabapple
Ms. Crabapple is a burlesque performer-cum-artist whose recent book, Dr. Sketchy’s Official Rainy Day Coloring Book!, is all the rage with artists and voyeurs alike.

Box-munching is a right of passage for the female intellectual. Which of us in art-school hasn’t drunkenly proclaimed our sisterhood with Sappho? Guys are insensitive and smelly. They break our hearts. They accidentally call us fat. For me, banging chicks felt like heady liberation. Until I realized I kept jonesing for cock.

The first girl I slept with was this nail-tough, copper-skinned Puerto Rican woman who worked at my coffee shop. She was 36. I was 19. Attempting to act like the opposite of my many lousy boyfriends, I bought her flowers, then tried an ingénue act so bad I’m surprised she could stand me. She took me home anyway, tied me to the bed and nailed me with a strap-on. The next morning, we drank fresh mojitos in her kitchen. Getting slowly drunk in her huge Sunset Park apartment had all the aspect of heaven.

We dated on and off, though I soon realized that, like many pseudo-lesbians, I couldn’t get emotionally attached to women. So now I confine my girl-attraction to paper — where it continues salaciously to this day.

MY FIRST TIME • Rachel Kramer Bussel
Erstwhile and much beloved sex columnist at the Village Voice (she was replaced by the celibate bourgeoisie) Ms. Bussel currently hosts the In the Flesh Erotic Reading Series at Happy Ending and is the editor of several collections of naughty fiction.

When I was 17, which seems very young to me now, but felt very old then, I was still a virgin. All my friends had already had sex and I felt totally behind. It was the summer after high school and before college, and I was working at a very small non-profit group in Maryland. There was this older guy (31) who I spent my whole summer flirting with. I really had no clue about sex, and had only made out with a few guys before that, but I knew at some point that I wanted him to be my first. Finally, one night we wound up at the movies (we saw The Firm) and later went back to his place and did it.

I honestly don’t remember the details about the sex itself, but do recall feeling totally insecure because he was so worldly. He’d forget that I was a virgin, and ask questions like “Have you ever had a threesome?” I let him take naked photos that he jerked off to, and felt really cool for having done that, but then when I got to college I felt weird about him having those and made him tear them up. Also, I was totally convinced that I was pregnant, so much so that I went to get tested at Planned Parenthood even after I’d gotten my period.

I think our ages and experience levels were too imbalanced for me to really feel comfortable enough to truly enjoy first-time sex, but the week or so we were together made me head off to school feeling a little bit less behind my peers. I’ve been catching up ever since!

MY FIRST TIME • Jonathan Ames
This story is from my first novel I Pass Like Night, but it’s a rather autobiographical account of my loss of virginity and so it’s practically non-fiction.

I lost my virginity my senior year in high school. I had a 16-year-old girlfriend with brown hair in braids and cute little tits, and I wish I had a 16-year-old girlfriend now. I think about her when I go home and I pass the sign for her street, but I haven’t seen her in years. Sometimes I think I’ll give her a call, but she’s probably not my type anymore.

We were going out for about two months and did our making out in the car. Then a big break came our way — her parents were going out on a Saturday night. They told her, even though they liked me, that I couldn’t come over. So after they left she called me and I drove over and parked the car up the block, in case of neighbors, and went in the back door. We made out for a while on the couch in her den and we were going farther than ever before. […] I made it all the way to third [base] and I rested there awhile, until she said, “You can if you want to.”

I hadn’t expected to hit a home run and I just lay there stunned. She waited and squeezed my hand and I was caught in a lie. I had told her that I had slept with older girls, so that whenever she was ready (she was a virgin) I could handle it because I had experience. So she was ready and I was filled with fear and I didn’t know what to do, but now was no time to get honest. I forced myself into action and I whispered to her, “I want to.” I pulled my underwear off, got my penis out, lay on top of her, poked it around a bit, and then went soft. After having an erection for the last hour, and the last four years, my penis died at the most crucial moment of my young life and my heart was breaking. I was pushing it against her and it was bending in half and receding to the point of vanishing, and I was hoping she wouldn’t know the difference. I was moving around as much as I could, trying everything, rubbing this way and that, but nothing helped. I was hating myself and it seemed like my father was right behind me yelling “Klutz!” like he had done my whole life. I kept on pushing and praying and almost crying, almost thought I would quit, and then God came through and it got hard and slipped in there like I had been doing it my whole life. And I think my whole soul just gave a big smile and I thought to myself, this is all I want to do from now on. I just held myself in there and didn’t even move, my eyes were closed and I was proud. Then she moved like a woman can, to take in a little bit more, and she made a noise, a sigh, and maybe she raised her hips just the slightest, and I was overwhelmed by her presence and the urge to come, and I panicked, yanked it out, and went on her belly. I had lasted ten seconds and she was 16 and there was a look on her face, and I never wanted to have sex again.

Mr. Smith is likely the only artist to have appeared both at the Whitney Museum and onscreen in a porno. It’s true.

The first time I had sex I remember thinking — like probably a lot of people — "Oh my god, I'm having SEX — this is weird! Wow, look at this, it's sex, and there's boobs and bouncing and... whoa..." And then I thought, "Well, sooner or later I'll get over that and I'll be all sophisticated and it'll be like normal." But it wasn't true — every time, even when I'm doing a movie, I still go "Oh my god, I'm fucking having SEX — this is so weird!"
The other thing I remember thinking was "Oh god, this table is totally gonna break,” which also still comes up now and again.

MY FIRST TIME • Shandi Sullivan
Ms. Sullivan is currently working as a DJ under the name “Shanthrax.” She is perhaps best known for her memorable appearance on America's Next Top Model.

I was a junior, just turned 18 a few months prior, and was on my way to the senior graduation party. The moon was full and I'll never forget looking at it and thinking, "Tonight, it's going to happen. I'm going to lose my virginity." At the party, which was out in the middle of a field, everyone was congregating around the massive bonfire. We were all getting our fix. Mine that night was a hit of acid. Before too long, and after a couple of beers and a keg stand, I started talking to Trevor. He was a senior who I had gone to prom with. We had tried having sex that night, but there was no condom in sight. Anyway, I'm wasted and snuggling up to him; we're making out for what seems like hours. I keep saying, "Come on, let's go." He replies, "Are you sure?" Since I'm totally loaded and I know he's not trying to take advantage of me I remain persistent. Finally, he grabs my hand and leads me to a tent out by the edge of the field. I lay down on my back and he slowly takes off my clothes. No kissing, no caressing. Then his clothes come off and… nothing. I don't feel anything. Amazing! I thought this was supposed to hurt? Five minutes later, he gets up, puts his clothes back on and leaves. No words and me lying naked realizing what just happened. My first time was painless, quick, with someone who wasn't aggressive, and I didn't regret it afterwards. Then I didn't have sex again until a year later. Go figure.

MY FIRST TIME • Eamon Harkin
Mr. Harkin is the international DJ superstar behind Calling All Kids.

My recollections of the first time I had sex are blurry at best, which I might feel bad about if I weren't almost positive that hers are as well. It boils down to something like this: I'm 16 and it's the summer of 1993 in Derry, Ireland. I know it's the summer because the "event," if you will, took place outdoors. I'd been out all night with friends at a rock club, the name of which has escaped me, but it was within the walls of Derry, which happen to be the only completely intact walls around any European city. The lucky lady, if we'd ever want to call her that, was a very good friend, also around 16. Fast forward to the end of an evening of copious amounts of alcohol and bad grunge music, and somehow the opportunity came up for us to momentarily leave the club together. As an "eager" Irish Catholic lad to whom these opportunities were not necessarily common, we left quickly and made it as far as the top of the wall, which is not just a barrier but also an elevated pedestrian walkway. The memories at this point can be summed up as follows: Vertical, brief, probably pretty clumsy, hopefully private, and ultimately pretty innocent. We made our way back to the club after what was probably no more than 20 minutes outdoors, and ended the evening with our crew. We remained friends but never uttered a word about it or repeated the act.

MY FIRST TIME • Ben Greenman
Mr. Greenman is an editor at the New Yorker, and is the author of Superbad and Superworse. His new book, A Circle Is A Balloon and Compass Both, comes out in April.

As long as we were kids, it didn’t matter. Then, suddenly, terrifyingly, the syntax shifted. Girls had been something, but now they were something else, sitting right there in class, easy to talk to and impossible to talk to, more than an idea but less than a reality. At first I didn’t let it get to me, not because I was satisfied with failure, but because it seemed as though everyone was failing equally. The one exception was a guy in eighth-grade phys ed. Already nearly bearded, he banged on his locker for attention and announced that he had done it with a cheerleader. The next day, he told us again, and the day after that, too. Something about his steely, almost pleasureless insistence on repeating the story scorched the ground around me, and I started looking toward the summers, when I went off to an academic camp a few states away. It was lousy with smart, eager, aggressive kids who, for one reason or another, weren’t getting lucky at home. Hormones were perpetually at high boil. The first summer there, I got a bra off a short but still leggy Texas girl who was pleasantly rude and always smelled like shampoo. The second summer, we went up into the library, unshelved some Japanese erotica, and got back to business. Underwear (hers) and wide eyes (mine) came into play. The third summer, she didn’t show up. Her parents had sent her to dance camp instead. I fantasized about a divine hammer that would powder her devil parents into dust, and rebounded with a sweeter, duller girl from one of the Carolinas. When I felt her up I knew that I was laying groundwork. The next summer, finally mostly sure of it, I met her in her dorm room one afternoon and we exercised our mutual determination. I would like to report that the first time was anything less than anticlimactic, but the truth is that it was as boring as everyone else’s story: there was fumbling, excitement, some clarifying terror, and, at the close of the majestic two minutes, a great sense of seriousness that, 20 years later, seems like a kind of sadness, a mutual acknowledgement that innocence was going if not exactly gone. I didn’t really talk to her much after that summer. I remember only her first name. I wouldn’t know her if I saw her.


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