10 People Reveal Their Most EMBARRASSING 'Losing Their Virginity' Stories

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embarrassing stories about losing your virginity

"I'd gotten a nosebleed and just straight-up started bleeding all over her."

No matter who you are, who you're with, or how prepared you think you are, losing your virginity is rarely without its awkward moments. By now we all realize that sex the first time is never the magical, coming-of-age sexual awakening Hollywood likes to paint it as, and, instead, is usually loaded with awkward, embarrassing stories about losing your virginity.

We’ve asked around and here are a few of the most mortifying, embarrassing stories about losing your virginity that our readers have experienced during their first romp between the sheets.

1. My penis would not go in.

“Well, I don’t know if this counts but I tried to have sex with my first girlfriend a handful of times and it just wouldn’t go in. I don’t mean that it hurt a lot so we had to stop; I mean IT WOULD NOT GO IN. I felt like I was hitting a wall of flesh. We tried warming up more and digital penetration and still, I couldn’t even get the tip in enough to count. In fact, it never worked and, eventually, it broke us up. I still consider it my ‘first time’ though because of the intent but it was worse than expected.”

2. We got caught in my car.

“The first time I had sex was in my brother’s car. We were parked in what I thought was a very remote, secluded spot way out in the country. However, he had a couple of friends who were into taking dirt back roads, saw his car, thought he might need help, and stopped to offer a hand. To this day they have never let me live down the fact that they caught me during my ‘first day on the job.’”

3. He started crying for no reason.

He just started crying... Not like gentle tears of tender love but full-on, body-shaking sobbing... while he was still thrusting. We’d been dating for a long time and were losing our virginity together, so it was special, but him bawling made it so, so uncomfortable."

4. The spermicide on the condom made my mouth numb.

“I’d read in some women’s magazine that a ‘sexy way to put on a condom’ was to use my mouth, so I went for it. I didn’t take into consideration, however, that the whole thing was covered in spermicide, so my mouth went almost completely numb immediately following.”

5. I farted on his testicles.

“I was not at all prepared for the extra push on my insides that would happen once he was in there and I farted. I know that farting during sex is really not a big deal, but we were having deep, meaningful, wedding-night sex that we’d always built up to be this monumental event and then I blasted him in the testicles with a fart and destroyed all remaining mystery about my feminine wiles. I hid my face for about an hour in my shame, which honestly is the most embarrassing part of this whole story in retrospect because now I fart on him so often it’s practically recreational.”

6. I got a nosebleed.

“I was with this girl who had had sex before so I was already having mad performance anxiety. Anyway, things progress, we get to the final act, and I’m on top and trying to play it cool, but in my head, I’m all ‘HELL YEAH!!! WOOO!!’ Suddenly, she opens her eyes yells and then jerks away from me, and I notice she has blood on her face and chest. In my excitement, I’d gotten a nosebleed and just straight-up started bleeding all over her.”

7. He ejaculated right into my eye.

We were both virgins and we wanted to try it without a condom for the first time, but we planned in advance that he would pull out. As he did, it shot a straight line from right above my boobs, up the side of my face (and into an eye), and into my hair. We opted for a condom the next time just to save time in cleanup.”

8. We had sex in full view of an entire party.

“I was very, very drunk at a party and this girl I’d had a crush on for years started flirting with me, so after another hour of slamming drinks and groping each other, I led her away from the party to seal the deal. By this point, I was in a near-blackout, but I thought we’d at least gotten to a place where we were alone. I was mistaken. Apparently, we were both in full view of anyone who wanted to watch me attempt awkward, drunken, first-time sex, which included most of my friends. They filled me in on my sloppy details later.”

9. He just sat there, not thrusting.

“My high school boyfriend kind of didn’t know what to do. I thought it was weird, but I was a virgin at the time, too, so I thought maybe he was just more sheltered than me. He would do stuff like putting his penis in and then just sitting there, and not start pumping until I suggested it. He couldn’t stay hard and said all the eye contact was making him nervous, so we tried doggy style and he finally got into it. Anyway, he came out of the closet about a year later.”

10. I went into the wrong hole.

“I went for her butthole instead. I was 15 and had no idea what I was doing with a woman. Poor girl."