15 People Open Up About the Cringe-Worthy Ways They Lost Their Virginities

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If you have no regrets about the way you lost your virginity, we’re really happy for you! Yet for most of us, the first time is, well, awkward emotionally, logistically, spiritually, etc.

We found 15 of the most cringe-worthy How-I-Lost-My-Virginity stories on Reddit, and they’re pretty hard to read.


“I had sex with this girl who didn’t tell me she was married.”

“In 11th grade I threw a party because my parents were gone for the weekend. It ended up getting out of hand with over 100 people showing up. A girl I’ll call ‘Tori’ decided to have sex with a senior from another school in my room. Since it was her first time, she bled everywhere. All over people’s bags, some of my clothes that were on the floor, my bed and the floor. Feeling embarrassed, she tried to clean it up with a bottle of spray bleach she found in my bathroom. She ended up bleaching my carpet and bed sheets. She passed out covered in her own blood and bleach. ”


“I tried to finger her without any knowledge of what I was doing. It was more like mindless meat-stabbing and after five endless minutes she went: ‘Are you looking for anything in particular?’ ”

“I was 17, and my more experienced girlfriend was 19. She rented a cheap motel room for us. We’d been dating and fooling around for about a month, so I was a little nervous, but mostly excited. As we’re laying there, basking in the afterglow and each other’s warmth, we hear them. Police sirens. Still naked, we jump to the window. From our second floor room, we can see two or three police cars streaming into the parking lot. Holy shit, I thought, I’m getting busted. We watch, frozen, as the cops exit their vehicles and barge in to a first floor room below us. After another hour or so, they all left. We left shortly thereafter.”


“The first thing I noticed was that it didn’t feel nearly as awesome as I had imagined. Like you spent your teen years imagining what it actually feels like, and then you’re finally there, with a REALLY hot chick and it’s like meeeeeeh. Then, after a few minutes, I realize that it’s not that it doesn’t feel awesome, it’s that I don’t feel anything at all. Like, I couldn’t feel my penis. So, not only was it my first time, but I also couldn’t FEEL anything. I’m sure it was probably the worst sex she’d ever had. The only thing I’m thinking about is, ‘Oh my god, I must be gay.’ I thought I was bi this whole time because I’ve always found myself attracted to women more so than men, but here I am having sex with a woman and I can’t feel ANYTHING! I figured I just had to be gay. She eventually made some noises that I’m sure had to be fake. I followed them up with some awkward kind of grunting. Then, after we shared a post-sex kiss. I told her I was going to go outside and have a smoke. I don’t smoke, but I had a pack of mini-cigars for when I hang outside with people that do smoke. So I go outside and stand there, pretending to inhale, contemplating what life will be like as a gay man. I eventually shuffle back into my room, and we fall asleep together. The next morning, in the light, I look at the floor and see the condom wrapper. It was a triple-thick desensitizing lubricated condom for guys with stamina problems.”


“She was on top of me, we were on her bed, the door was on the opposite wall behind her. Her brother walked in, she grabbed the blanket to cover herself up and quickly jumped off of me, and for some reason I quickly grabbed my phone and pretended I was texting. I didn’t even think to cover up or hide or anything, I was just lying on my back fiddling with my phone while my girlfriend tried to rectify the situation.”

“I went in and thought I came instantly. I didn’t feel an orgasm, but I felt fluid rushing out. I figured it was due to anxiety that I didn’t get the pleasure out of it. After rolling off, we saw blood everywhere. I asked her, ‘Is that you’? And with this horrified look on her face she shook her head no. I went into the bathroom and checked myself out. I had a little cut just below my head that was bleeding a little. I had gone limp by then, but I assume it was just flowing out when I was erect, hence the fluid sensation.”


“My story starts awesome, then gets awkward, then goes back to awesome. So after fooling around with my GF for a few weeks she finally hints that she’s ready to go for it tonight, and that I should buy some condoms. I run to the pharmacy after work and am faced with 20 different types of condoms, I just grab the normal type and try not to seem too nervous while paying. We get to her place that night and things start getting hot, we finally strip naked and I get the condom out. Having never used a condom before but not wanting to show it, I casually try to keep up conversation while I’m struggling with all my might to put the damn thing on. After breaking the first one, I kinda excuse myself and walk into the bathroom with a second condom and the instructions. After a few minutes I am panicking because the condom will not go on and am mortified that I look like an idiot who can’t even put on a condom. She finally walks into the bathroom confused and suggests I try a condom she had in her purse just in case. That one is not going on either, and I’m standing there with a boner in one hand, unrolled condom in the other muttering apologies and feeling absolutely ridiculous. Maybe the condoms are too small she comments; we should buy XL ones. So we get in my car and drive to the nearest pharmacy, and then came the second most awkward part; this was a different pharmacist, and this one did not have any condoms on display, so I had to ask an elderly lady for condoms for gentlemen with extra girth. The lady smiles and looks at my girlfriend waiting in the car outside. She goes to the back of the store and hands me the box with a wink and told me to have a nice night. Later we sexed, and it was glorious.”


“I was getting hot and heavy with my girlfriend when my buddy called wanting to hang out. I told him it wasn’t a good time cause I was finally about to have sex. He then insisted I’m not going to take that long and he was coming over. Seven minutes later he was knocking on my door and I really was already finished.”

“The morning of the big day I cut school, went to my girlfriend s house, we got naked, we got aroused, foreplay ensued, I put the condom on and about 10 minutes later was on my way to the ER. Before that day I d never heard of, nor would I have thought that anyone could be allergic to latex ”


“I lost my virginity to the words ‘Just sit on it.’ ”

“The dude, who was Mormon, just curled up into a ball after they were done and cried. I guess he thought he failed Joseph Smith or something.”

“I got chlamydia.”


“I used to hang out with bums, freaks, and weirdos in the downtown area of my city. I took some friends and a girl that I liked down there to drink. We end up running into this eccentric guy who tells us he’s a vampire, and 400+ years old, even though he looked to be in his mid 20s. He’s down to buy minors booze, and we proceed to party. As the night wears on, he gets weirder and weirder. He shows us how to suck the life force out of someone, by sucking on said girl dance partner of mine. We end up getting a ride back to her place from the vampire and she invites him in. He goes full creeper, trying to make out with her, telling me we can have a three-way. I flip out and tell him to leave. Dude doesn’t back down. I had to forcibly pull him off her bed and walk him out the door. With the vampire gone, I return to her room and she asks me to sleep with her, not in the sexy way. We wake up in the morning and I awkwardly say ‘Wanna have sex?’ She said yes, I lasted a full minute.”

“It lasted five seconds.”

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