Popping His Cherry: The Women Who Have Sex with Male Virgins

What's so sexy about unspoiled male flesh? We spoke to some serial deflowerers to find out.

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Dec 14 2015, 3:50pm

Photo by Victor Torres via Stocksy

I knew a guy in high school who scratched actual tally marks into his bedpost. Not just for the number of girls he had slept with, but for the number of virginities taken. In one form or another we've all encountered the seedy male stereotype who loves to deflower.

But it's not just men who are into taking virginities. Women like collecting V-cards, too—we're just unlikely to scratch up a perfectly good bed frame over it. Personally, after one time in high school, I swore never again—dude was Catholic and flung major steaming heaps of guilt my way afterwards. To learn what's so sexy to some about a squirming young virgin, I spoke to three women who get off on sleeping with them.

Screengrab via YouTube

BROADLY: How many men's virginities have you taken?
Catie* (45): Four (alleged) penis–vag virgins. I say alleged because I think some young men may be using this as a move to get laid or to have sex without a condom: "I'm a virgin—please help me out," or "I'm clean for sure, because I'm a virgin."

Will you tell me about the experiences?
When I was still a teenager but no longer a virgin, I had my first. He was 16 and very cute and had some sexual experience, just not actual penetrative sex. He was actually quite fun. I didn't realize he was a virgin until after we had sex, so it wasn't that I planned it. We had sex one more time several months later, and he was basically the same sexually.

Bring your own condoms and don't be shy about giving direction.

I had sex with a 26-year-old who claimed to be a virgin, and I believe he was. He was shy and a little embarrassed about getting naked, wanted to keep his shirt on. He had a look of amazement during the whole thing. He said he was very inexperienced and had really only made out and never been naked with a woman before. Everything seemed to blow his mind. Like touching me with his hand made his eyes get wide. He didn't get off, even though we did a lot of things over a couple hours. He felt like the condom was maybe the problem, and that none of it felt like his usual masturbation technique. It had a bit of a scientific feel to it, not very passionate or emotional.

Only one was really terrible. He just lay there with a huge hard-on not having a clue what to do. He was 19. He looked starstruck.

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What about virgins turns you on?
I really prefer younger men. All of them were attractive to me in general. I really enjoy giving pleasure as well.

Do they ever become obsessed with you afterwards?
This didn't really happen, but the 19-year-old has asked repeatedly for another try since he's had some more sex, to prove that he's not still lame.

What advice would you give to someone who wants to fuck a virgin?
Bring your own condoms and don't be shy about giving direction. And don't fake an orgasm just to make them feel like they did good! Sets them up for failure.

Screengrab via YouTube

BROADLY: Will you tell me a little bit about yourself?
Kelly (22): I'm a dance and swimming instructor. I live a pretty normal life. I have a small group of friends, most of whom know all about my kinks.

You've taken three V-cards. What was that like?
Every time was very different. The first time was with a boyfriend who was overly confident; he thought he had watched enough porn to know what to do, so I let him go for it. He had no idea where to put it, and when I showed him, it didn't take long for him to finish. He was so cocky afterwards—until he asked how it was for me, of course. I told him he needed more practice. After a few days of sulking, every time we had sex he would try so hard! He wanted a play-by-play instruction manual.

The second time has to be my favorite—the guy was so shy he couldn't even say the word sex. We arranged to meet up at his house; we both knew we were going to have sex. He tried to play it cool—putting on a film, Netflix and chill. He nervously started playing with my stomach and pulling my top up, so I turned to kiss him. I think it took him by surprise. I got down to my underwear and started undressing him. He jumped under the covers so I couldn't see anything. He was so nervous I decided to take control. I loved edging him, stopping right before he was going to come. When it was all over, he ran straight into the shower. Afterwards it was like he had put a big brick wall up; he stopped talking to me and completely denied anything had happened between us.

I love making men nervous.

The third time the guy had specifically searched out someone who would like to take his virginity. We spent a month beforehand talking about his expectations and what he thought he might like. When things finally came down to it he was very open and could talk to me freely; it was more of a lesson for him than a hot and steamy experience. Afterwards I answered all the questions I could so he could finally have the courage to have sex with his girlfriend.

Did any of them ever get clingy or obsessed after?
In my experience no one has become obsessed or infatuated after. Guys tend to get distant; they might be embarrassed that things may have not gone the way they expected. Sex isn't always like porn. Guys are always afraid of being judged on their appearance or performance.

What about virgins turns you on?
I love making men nervous. And losing your virginity is one of the big life experiences; everyone always remembers losing their virginity, and who it was with. I guess I like the thought that they will remember me many years from now. I think it's difficult for guys nowadays; it's so easy for them to lose all confidence in themselves. I'd like to think that in some way I help them become more confident, making life a lot easier for them.

Screengrab via YouTube

BROADLY: Tell me a little bit about yourself.
Rachel* (44): I'm a woman who discovered this rather wicked side of myself. I'm single, been married in the past, and I love being a domme. I am fully and gainfully employed; I have a master's degree. I love men. I love sex. I only play safely. And I am very, very patient. Not everyone wants to deal with virgins. I am willing to be gentle and patient.

So you've taken men's virginities?
Yes, I have taken a man's virginity—anally.

Anally? How many?
How many? Seven. I don't force anyone... I also don't go after anyone. They find me.

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What turns you on about taking anal virginities?
Turn-ons? Begging, the lead-up to the actual act, seeing someone go through the emotions, and seeing a man's body shake in anticipation.

Do they ever get obsessed with you?
Good Lord, obsessed? No. But one reason may be that I am somewhat selective. I won't agree to a play session until I feel comfortable with a person; it may take a while. I'm usually on good terms with my boy toys.

What advice would you give to someone who wants to bang a virgin?
Someone who wants to bang a virgin? Don't use the word bang! I have no advice—people do what they want when they want.