Losing Your Virginity Stories
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Losing Your Virginity Stories
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Losing Your Virginity Stories

Crazy First Time Stories That'll Make You So Glad You're Not A Virgin

We tend to measure masculinity in part through sexual experience. Teen boys don’t want to get laid just because they’re pumped full of hormones; they want to get laid because they want to be men.

This attitude creates a lot of pressure for males, and can encourage them to think of women more as conquests than human beings. Guys who wait to have sex for “too long” might feel ashamed, like something is wrong with them.

But despite the way men tend to prize the big event, having sex for the first time is a vulnerable experience. A line is being crossed, culturally and physically, and might happen any variety of ways: Badly, through abuse (given or received); well, within a healthy and caring relationship; and anywhere in between, with results varying from hilarious to heartbreaking.

Parts of Reddit are clearinghouses for personal anecdotes. We plumbed its far corners to find stories from men about how they lost their virginity, so we can take an eclectic look at the first time and see just how awesome, awful or confusing it can be.

User bearsonsays starts us off with a fairly typical, if risky, cherry-popping experience:

In high school. I was at my gal's place in the basement. We were watching the classic, award winning film, Bring It On and pulled the blanket up and made the move. As I am in the process of losing the V-Card I hear footsteps near stairs. I quickly jump up and zip up as her mother walks down the stairs. We chat briefly and she leaves. I turn to my gal and say, "was I in?" She confirms that I indeed had been. I was pumped! I high-fived her. It only takes a few seconds right guys? I chalked it up as a victory for my manhood!

For adults, having sex when someone else is in the next room over and liable to enter at any moment - in this case, it was bearsonsays’ girlfriend’s Mom — is “spontaneous” and arousing. But for the horny teenager who can’t get a moment alone with his beau, friskiness under the movie blanket is fueled not by adventurousness but by desperation.

Funktapus learned early on that this kind of desperation can lead to a bad experience.

17 years old... asked this girl to come study for a final at my house. We watch Eternal Sunshine of the Spotless Mind instead (great movie) and then start to make out. She asks me if I'm a virgin, I admitted I was, and she basically said she likes guys with more experience. I plead for her to fuck me anyway, she does and it was just kinda awkward and unsatisfying. Too nervous to barely keep it up. I drive her home, and we barely even talk after that. I dated an insatiable girl on birth control after that so I my technique improved, but my first time was bad. Oh well.

You have to be pretty desperate to plead for sex. In this case, grasping at the first available opportunity chad disappointing results.

Maybe not as disappointing as Benthos’ first time, though.

During a high school trip to Europe with a girl from another school. Having never seen a porn movie, the only example I had seen was lame sex portrayed in The Hand with Micheal Cane. I tried going down on her because I read in a cheap porn magazine that girls love a fuck after being eaten. Then I stuffed it in, and slid around a bit. She said wait, I came, pulled out, felt embarrassed, and left her hotel room. The next morning I couldn't look her in the eye. I found out later she told everyone I was the worst fuck she ever had.

It may just seem like a funny story after the fact, but a bad first-time experience can create a lot of shame, especially for an insecure teenage boy. High school gossip after the fact doesn’t help.

But Joenorris94 suffered some real pain.

I was 15 at my house, my girlfriend of the time gets on top of me, rives around for a bit, I scream because it turned out I had a tight foreskin, it ripped, I bled, I cried. It was so embarrassing she denied it ever happening for three years.

Ouch! Things are feeling better now, though:

I am now circumcised and I enjoy having wild sex with my new girlfriend in funky positions.

A lot of first-time sexual experiences are fueled by intoxicants. This might help to break the ice, but especially when young people are involved, a night of reckless drinking can lead to a miserable (and confusing) morning after. Chubbybunns recounts

Don't really remember it clearly because i was pretty drunk at the time and she was too. she was a little older than me and more experienced than i was. i remember flirting with her a bit, she flirted right back. everything got a little blurry and i vaguely remember clothes coming off. then my head cleared a little as she got on top and i remember that it felt really good. the next thing i can clearly remember is waking up next to her with a splitting headache and wondering what happened the night before.

Hopefully he came away with an early appreciation of how booze blurs the lines of consent. Not everyone is a reckless teen when they lose their virginity. For many reasons — many stories cite social anxiety, autism spectrum disorders, or a religious upbringing — many men don’t lose their virginity until they are well into their 20s or 30s.

Lost_it_at_39 tells his story:

It lost mine at 39. Yes, 39. I had my first naked-with-a-girl experience at 23, but when she told me she wasn't in love with me, I physically locked up. Took me months before I could even masturbate again. Eventually I got together again with the same girl, but during foreplay she played with my penis and I came immediately. That was the last day in college and the end of that story. Second time, I was 34. I actually penetrated but it immediately went limp. That was an amazing confidence builder. The third time was with my current wife. We had gone out on a few dates. We had watched a movie together at her place, kissed the first time that night. She asked if I wanted to sleep over in the literal sense of the word. I didn't sleep at all, fully erect the whole night. We did the deed in the morning. I came in 1 minute. Maybe some men just need to meet the right person before they’re ready.

lost_it_at_39 adds, "Things were already better the second time and now we have a totally normal and very satisfying sex life. I'm a happy man."

HerrGansefus finishes our cycle with a brief, simple story. We should never forget about the power of puppy love.

At home, in my room, with a girl I loved like only a fifteen-year-old can love, and she loved me back just as much. Best way to lose virginity, I think.

What about you? Do you have fond memories of your first time, or embarrassing ones? Let us know in the comments.

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