I Asked 15 Guys About How They Lost Their Virginity And Their Stories Will Make You Cry Laughing

I Asked 15 Guys About How They Lost Their Virginity And Their Stories Will Make You Cry Laughing

"Jenny if you're reading this, let's give it another go, I promise not to hit your head and I can last longer than 45 seconds now."

American Pie

You never realize how different girls and guys are until you ask them both about their V-card.

What happened?

How was it?

Would you do it again?

You can't prepare yourself for the various answers you'll receive from both sexes.

Here were my favorite 15 answers that I received when I asked guys about their virginity, how they lost it, how it was, and if they would choose the same girl.

1. Motorcycle Fuck

"So I guess the first time I actually lost my virginity was a little while later. I met some girl at a party and took her on my motorcycle afterwards. It was fun and we exchanged numbers. Then we texted for a while and eventually started flirting. I went to visit her on my motorcycle and I ended up staying with her all weekend but for the first day we got really high and basically did a bunch of foreplay.

I was too nervous to get it up (and stoned). Late that night while I was sleeping, I woke up and went to pee...When I came back I was hard so we fucked. Literally 30 seconds. Life is about the experience but I don't regret it. I kind of wish I would have told her that she was my first, at least it would have been a little bit more special. Worth the experience but I also regret not getting laid when I was younger and thinking it was all about waiting until marriage. I gave up on so many missed opportunities in high school."

2. First Time Friend

"My first time was actually with a friend from school. I got along with her really well, and one day I told her I never did it before and she was really surprised by that. She offered to be my first and I was okay with it, so we went out to eat one night and after that we went in her car and went down a back road and went to town in her back seat. It was weird because we were low-key freezing but we kept fogging up the windows because of all the friction. The embarrassing part was a mixture of being nervous and it also being freezing, I had a hard time actually staying hard. I wasn't even able to finish my first time. Other than that it went pretty well, all things considered.

Now would I do it that way again for my first time? No way. I would have chosen a warmer location."

3. Mom's Ford Explorer

"I lost my virginity in the back of my mom's Ford Explorer in high school. I didn't know what I was doing and it was awkward. Her and I didn't really talk afterwards and have lost touch. At the time I liked that it happened and I got it out of the way. It did make me feel like a grown man. If I could redo it, I would save myself. Not really for marriage, but for when I'm with someone I find special and have feelings towards. You only get to lose it once in your life and I just wish it would have meant more to me."

4. Her First Too

"The best part about losing my virginity was that it was her first time too, so I could screw up, not get off, not get hard, or last 20 seconds and she'd have nothing to compare it to. Sadly, a lot of that ended up happening our first time together, but I was happy to get it out there, and it get it out of the way. Sex today isn't like sex was my first time. People put too much emphasis on the "first time" like it's suppose to be the best day of your life. Really it's just a lesson on what not to do in the future. I learned that then, but she did too, so it was fine."

5. The Stripper

"Losing my virginity was probably the saddest excuse for losing a V-Card ever. I lost it to a stripper, so does that even count? I practically had to pay someone in order to lose it, so that put me off in itself. Then I couldn't get hard. Then I couldn't get off. Then after it was all done, I left and never spoke to her again. It was one of the worst experiences of my entire life, and I would not have done it over again if given the opportunity, I would've chosen someone else."

6. High Sex

"This was actually my first time getting stoned. (I had tried to smoke before but never felt anything from it). I was with some friends, and this time I actually got high. I had been talking to a girl that was at my friend's and we were both stoned out of our minds. It was undoubtedly the best thing I had done up until that point, and being high and having all my sense's heightened was an unforgettable feeling. I liked the girl, I liked the time, and I loved the night. 10/10 would love to have an experience like that again."

7. First Love

"My first time was with my first love, and for that reason alone I would say it was the perfect person to lose it to. I can not think of anyone else during that time period I would have rather lost it to than her. I wasn't her first, but I know she loved me too. She made it all such a memorable experience, and it was nice knowing I had someone to be with even after it was over. It wasn't just one and done. It kept happening and kept getting even better. Eventually we did break up, and it was a difficult decision on both ends, but I truly believe she was meant to be my first."

8. The MILF

"I had the ultimate experience when I lost my virginity. It sounds like something straight out of a porno, which (as much of a douche as I sound) was one of the proudest moments yet for me. It was right after I graduated high school, and before I went off to college I was cutting grass in my neighborhood. We had this woman that lived a couple doors down from us, who had a husband that died a few years back. I always cut her grass and she always brought me out lunch and something to drink. One day, I was helping her with some gardening and she told me to come inside and get some food in my belly and get cleaned up. As soon as I went inside she was really flirty with me, and definitely coming on to me. I was pretty naive when it came to sex, obviously, since it was my first time, but she led the way with everything and it was the coolest and hottest experience of my life."

9. My Best Friend

"I lost my virginity to my best friend. Right off the bat it sounds like this was a good call because I would be comfortable with the person I was doing it with, but honestly, I really regret it. It completely ruined our friendship. We were hoping to just get it out of the way, and what better way to get it out of the way than by doing it with someone who you trust and have been close to your whole life. Maybe it works for some people, but we couldn't get our friendship back on the same page it once was. I'm still mad at myself for being so stupid. There were a million girls and I chose the one that I should have never jeopardized things with."

10. Who Was She?

"I don't remember her, and I don't even know her name. I had been dating a girl prior to that for two years and we never slept together. She was saving herself for marriage. One day she broke up with me randomly because she said she wasn't in love with me anymore. I was really hurt and that night went to a college party. I got super drunk and lost my virginity to some random girl there. I never spoke to her after that, and I don't even know her name. It was a shitty way for things to happen and I think back to that point and have bad feelings because it was such a bad time in my life."

11. Not My Girl

"This is both a fucked up and hilarious version of how I lost my virginity. I was kinda wild in high school and I hung out with all of the older guys who had already lost their V-Card. I was super embarrassed to point out to anyone that I was still a virgin, so I had to lose it and I had to lose it fast.

I planned on losing it at this party I was going to with my friends, and I had my eye on this girl the ENTIRE time. I got so hammered to the point I was starting to black out, but I just remember this girl really being all over me, so I was all over her too—obviously. I asked her if she wanted to find somewhere to fuck and she said yes. I was super pumped, but also super drunk but I ignored that fact and went to find the closest thing to a bedroom with her.

As soon as we closed the door, I threw up ALL over her shoes. So we actually went into the bathroom and started to take a shower together. (At this point I have no idea how she still wanted to have sex with me). I don't even think we had sex in the shower, but we somehow made it to this bed...(Still don't know whose bed this was). I woke up the next morning, starting to piece together things from the night before. I could smell throw up, I saw water everywhere from what I assume was the shower (unless I pissed myself) and I saw a girl laying beside me turned the other way. Then she rolled over and I realized I fucked the wrong fucking girl."

12. Blood Is A No Go For Me

"To keep it short and sweet, I lost my virginity to a girl who was also losing hers at the same. As we were going at it, I looked down and saw blood everywhere. I clearly understood why there was blood—it was her first time, but trying to explain that logic to myself while I was still trying to fuck her wasn't going too well. Suddenly all the blood rushed from my dick straight to my head and I passed the fuck out. I woke up like 30 seconds later, saw all the blood, and told her I couldn't continue. She was not happy, and neither was my dick."

13. I'm Fine

"It's not too great of a story. It was more annoying than anything. My first time happened like a lot of other guys. It was over in less than a minute, I didn't know what I was doing, and I wanted to get it out of the way. I would've just kept it at that, had the girl I lost it to just dropped it. However, every hour for the rest of the day, she just kept asking me, "So how are you feeling?" I finally had to just scream at her (after being asked 20 times) "I AM FINE!" I can't watch the "Friends" episode where Ross is "fine" without getting a headache or without cracking up every time he yells it. I completely get where he's coming from. Ross and I are fine—end of story."

14. My Wife

"I wouldn't change a thing. I lost it to my wife, who has been my wife for seven years now. It is such a good feeling knowing that one day when we are explaining what sex is to our children, that we can say we both waited for one another and there is a special part of ourselves that only my wife and I know about one another. I know a lot of people think waiting is cliche, but for me, it was a really important decision, and I commend both my wife and me for waiting."

15. Can I have a do over?

"I lost mine to one of the hottest girls I have ever seen. It's seriously a story my 13-year-old self would've loved to repeat, had I not sucked so bad in the act. At one point we were fucking and I hit my head off of hers. It was really loud, and I know it hurt her more than she led on. I obviously didn't last too long, and I could tell there wasn't much to enjoy the way she completely ignored me and left afterward. If only Jenny from Dirty Myrtle could see me now. Jenny if you're reading this, let's give it another go, I promise not to hit your head and I can last longer than 45 seconds now."

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