Prev Next The Waterfail Chris, 25 "Looking back, I don't know what I was thinking, but my girlfriend and I decided we should lose our virginity in the shower. I guess we thought it would be hot and the water might make it easier. Now, I know how stupid we were. We both stripped down and got under the spray. At first, it was awesome. We soaped each other up and were touching each other ...

Prev Next The Big Letdown Peter, 33 "I was really nervous the first time I had sex. I wanted to measure up to my girlfriend's expectations and hoped it would be great for both of us. Everything seemed fine, but I was stressed throughout the whole thing. She could tell and kept asking me what was wrong, which made it even worse. Almost as soon as we started, I went totally soft. I think ...

Prev Next In-Tents Pain Tim, 23 "After graduating high school, my girlfriend and I planned a camping trip and talked about how we would lose our virginity to each other under the stars. It sounds a little cheesy, but at the time we thought it was romantic. On our first night in the woods, I laid out our sleeping bag and we went at it. We were being playful and, at one point, I grabbed her ...

Prev Next Boy, Interrupted Jeff, 26 "I was ridiculously young when I first had sex. My girlfriend and I were 14 and made the decision to do it at her house after school one day. Her parents both worked, so we knew we would have the place to ourselves. Since I couldn't drive, I even had to walk to the drug store to buy condoms and walk back to her house. We were in her room, doing our ...

Prev Next The Hecklers Steven, 29 "I was kind of awkward and shy when I was younger and didn't really come into my own until my junior year of college. I was still a virgin and my roommates constantly busted my balls over it. One night, I was at a party and this girl was totally into me. So I decided it was time to get it done with and invited her back to my place. My roommates were all ...

Prev Next The Cookie Tosser Greg, 31 "I was in college when I had sex for the first time. I was at a house party and drinking quite a bit. My girlfriend and I were both tipsy and headed into one of the bedrooms and began doing it. Halfway through I began feeling a little sick. I didn't want to stop because I didn't want to ruin the moment. All of a sudden I got nauseous and couldn't help ...

Prev Next The Fast Finisher Derek, 24 "I started dating this girl in college, and I was a virgin. She had been with one other guy and had a bit more experience. Our relationship moved pretty fast, and one night we started having sex. She knew I hadn't done it before, and I really wanted to impress her. She was so freaking hot, and I was psyched just to be in bed with her. I lasted ...

Prev Next The Virgin Bloody Mary James, 25 "I work retail, and most of my co-workers are women. I started hanging out with this one girl. I could tell she liked me, but I just thought of her as a friend. One night she called me, and I had just gotten home from being out drinking. I told her to come over and we could watch a movie. As soon as she got to my place, I made a move. We started ...

Prev Next Kid Tested, Mother Approved Dan, 21 "I had been with my girlfriend for about a year, and we were both virgins. Finally, we decided that we had been together long enough and should have sex. I had been talking to my buddy, Mike, about how it would go and he had given me a few pointers. Everything went smoothly, and my girl and I had a great time. A few hours later, I sent a text ...

It's a given: Losing your virginity is never as hot and smooth as you'd like it to be. Another given: It's fascinating to hear about the disastrous deflowering attempts of anyone who's not you. So in the interest of entertainment via schadenfreude, we got guys to tell us their horror stories. In other words, utterly embarrassing tales of getting the old V-card swiped. Click here for First-Time ...