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Women Talk About What It's Like to Take a Grown Man's Virginity

The responsibility of being a straight guy's first time is real, and it's even more stressful when you don't realize you've deflowered him until he tells you right after.

by Hannah Ewens
11 March 2019, 4:13am

Illustrations by Polly Williams

The door was barricaded, and I was drunk. After some promising foreplay and a few singular thrusts, it was clear that would be the sum of it. My dress was pushed up around my hips; I mentally shrugged. He was propped up, lying half on top of me. His blinking eyes had a sheen of elation, like he was seeing his surroundings—my messy room, me, the world—after a lifetime of being blind.

"That was actually the first time I've done that," he said. I laughed at first—then came the uncertainty, then the confusion, then a horrible cold feeling washed over my body.

After that night, I would inadvertently take the virginity of a number of grown men. Men in their early 20s, their late 20s, and their early 30s. One guy from work, someone off Tinder, grown men with real jobs and large friend groups. It was never someone you'd look at and think, He's a certifiable 30-year-old virgin.

That's the crux of this dynamic: No one knows who is a virgin and who isn't. The person you sit next to at work could be a virgin. The person you made out with on Saturday night could be one. You could very well be a virgin. And that's fine—people lose their virginity when it's the right time for them. But it's weird when, as the virginity-taker, you don't know what you've done until it's over.

On each occasion, the night would be fumbling along. I'd be told after the act itself—over coffee in the morning or a week later in a drunken outpouring of emotion. Upon finding out, I'd feel various things, none of which make me sound like a nice person. I'd been lied to, first and foremost. I'd been tricked into a role of responsibility. It's understandably hard for a virginal man, gay or straight, living in a hyper-sexualized society where male promiscuity is lauded, to admit that he hasn't yet had sex—but, really, letting someone know that you're about to take his or her virginity is, obviously, the decent thing to do.

When I told my friends about it, they'd tell me I was lucky. I will always be the first person for that guy, they'd sigh. Partners would come and go, but I'd be right there at the beginning of their timeline. I didn't share their opinion.

I'm over my curse, thank God, but I'm not alone in accidentally taking men's virginities. Here are some other women talking about this strange experience.

A VERY UNROMANTIC DEFLOWERING

It was a beautiful summer and the last one I'd be spending in London before moving away. I started hanging out with this guy through mutual friends. We went on a date, and afterward, I asked him back to my apartment. On the bus, he said that he didn't usually do stuff like that. I told him that was fine, thinking he meant hooking up on a first date.

We got back to mine and had sex, and afterward, he said he'd never actually done it before. It wasn't terrible or anything, and I don't think I'd have realized he was a virgin if he hadn't told me. He wasn't particularly embarrassed, but he seemed to think it was a pretty big deal, understandably.

He asked whether I thought he should have told me beforehand or not, but I didn't really mind either way. All I could think about was that it was bound to be a bigger experience for him than it would be for me. I definitely wished it could have been special for him. I didn't do anything special, like put candles or music on. The following week, I found out that all his friends had been waiting for him to lose his virginity, so it was a big deal for them too. I don't think about it much any more, but it's a nice memory.

Anoushka, 26

THE INTOXICATING POWER OF THE PUSSY

I was at a guy's house party, and we kissed in the backyard after polishing off the last of the Strongbow, before going up to his room. There were some clues that he was a complete novice—he'd clearly never encountered a bra before, and his kisses sent saliva pouring down my chin. We ended up having good, old fashioned missionary sex, but it still took him ages to find the right hole. Seconds later, it was over.

The next morning I woke up to him looking into my eyes and stroking my hair. He said, "Good morning, sexy," and kissed my head, which was in severe pain thanks to all the Strongbow. Then he whispered in my ear: "Not bad for my first time, shall we try a new position for my second go?"

He dropped the bomb that I was his first time while asking if we could go again. Then he asked if we could hang out and date properly, promising he could be a great man for me. I sympathized—this was his first time, and he was obviously excited, but I couldn't really handle it, so I made my excuses and left as soon as possible.

What followed was a barrage of messages and calls, asking when we could meet up, why I couldn't open myself up to him (ew), and how he didn't want "one of the best nights of his life" to be a one-off. After a few weeks of me ignoring him, he got the message and left me alone, but I'll never forget waking up to those puppy dog eyes. Lesson here: be cautious of the intoxicating power of the pussy.

Amelia, 25

THE TRANSATLANTIC QUICK FIX

I was recently single and hunting, just in the need for a quick fix, for want of a better term. I'd been chatting online to some dude in a band from the US, and they were coming over to the UK. I thought, Guy in band equals definite quick fix. I went to his show, and we hung out afterward. We drank a lot, and I asked if he wanted to come back to mine, in a very clear manner. He accepted my offer and the inevitable happened. It definitely felt odd from the get-go. He was taking forever and being really weird and bashful, which I've never really experienced in a guy before. I just assumed he was a cute shy one. It was OK, though—pretty good actually.

In the morning, when I was in the throes of a deep, aggressive hangover, he told me he was straight edge and admitted that the "beers" I'd seen him drinking were actually non-alcoholic ones. He looked like he was desperate to tell me something else, and after a bit of prodding he burst out that he'd been a virgin, until I took his virginity away.

I was initially pretty angry, but I'm still—to this day—not sure why. It just kind of freaked me out. I guess because there was plenty of opportunity to tell me, and we could have talked about it first. Also, if it was the other way round and the girl was sober and the guy was drunk and took a girl's virginity, even without knowing, it would be frowned upon—so I was also worried I could get into some kind of trouble.

When he got back to the US, he started messaging me relentlessly. A couple of days into DM onslaught, he told me he was about to buy flights to come straight back out and spend two weeks with me. I had to let him know that wouldn't be happening.

Becky, 25

THE ONE WHO COULDN'T KEEP IT UP

I moved back home a year ago after a bad break up and started working in a bar. The bar manager—let's call him Jay—was a guy close to my age. After months of flirting, and the time I gave him a quick blowjob when we were changing the barrels, we went on a date. Afterward we went back to his parents' house—which should have been a warning sign in retrospect, but how could I judge? I was back at home, too.

Once we got to his room, he couldn't keep it up. I thought it was because he was drunk. Now I realize it's probably because he was nervous. It didn't last long, but he was very well-endowed, so I had high hopes for future hook-ups. After sleeping with him a few times and him struggling to keep it up each time, I had a chat with him about it, and he revealed that he'd never slept with anyone before. He'd "done stuff" with plenty of people, but since falling in love with someone who was engaged—a one-sided love affair that went on for a couple of years—he'd never got to a position where sex was about to happen. Fair enough.

I couldn't sleep with him after that, though—it made me feel kind of gross and weird about the whole thing. He had troubles having penetrative sex, and I didn't want a casual hook-up to develop into me having to help him through his issues. I know that sounds horrible, but it's true. I've got my own shit to deal with.

Tara, 29

Names have been changed, except Hannah's. Follow her on Twitter.

This article originally appeared on VICE US.