14 People Reveal The Awkward Story About How They Lost Their Virginity

Troy Freyee
Troy Freyee

1. “I snuck the guy I’ve been seeing into my bedroom window to have sex with him. We planned it out, but in the middle of it my brother woke up and tried to come in my room. The guy I was with ran into the closet and hid naked before jumping out the window.” – Chelsea, 21

2. “I tried to be romantic for my girlfriend at the time, but I ended up starting a mini fire in my room because I lit too many candles and knocked one over.” – Paul, 25

3. “My first time was horrible, my parent’s were supposed to be out for dinner so I called my boyfriend to come over and have sex. Well, turns out the restaurant was a lot faster than usual and my mom walked in my room to see my boyfriend on top of me. She was NOT happy, we broke up after that.” – Lily, 22

4. “I figured it would just come naturally, but as a 15 year old boy I literally had no idea what I was doing. I didn’t even know where to put my dick, so I was just poking around and the only thing we said to each other was, “is it in yet?” Talk about a mortifying first time.” – Brent, 26

5. “My first time lasted 4 seconds, I think I might have got two thrusts in and then boom, I came. I don’t even think my girlfriend felt anything, but I was stoked about those 4 seconds at the time.” – Liam, 21

6. “I lost my virginity because this girl I was friends with had a big crush on me and she had done it before I did. She told me she’d teach me what to do, and she did right on her living room couch while Forest Gump was on.” – Derek, 24

7. “I lost my virginity to my teacher in high school. Our relationship was weird at first but she paid a lot of attention to me, always offering to help and I felt like she was kind of into me. She offered to tutor me at her home after school if I needed extra help, so being young and horny I went. I lost my virginity on her living room sofa, she taught me everything I know. Great teacher.” – Brian, 28

8. “I lost my virginity in the backseat of my friends car, we parked in the back of an empty parking lot we thought no one would show up to. Well, it turns out the cops show up there because they caught us and made us call our parents. We weren’t allowed alone together for what felt like forever after that.” – Sarah, 24

9. “I lost mine in a threesome with my friends when we were drunk. It was a lot for not knowing what to do, but I learned pretty quickly. Looking back I don’t think I would have wanted to lose it any other way.” – Nick, 27

10. “I wanted to wait until marriage to lose my virginity, but I ended up losing it in college in a bar bathroom because I couldn’t resist this guy I’d been seeing. Now we’re married.” – Ally, 29

11. “I was one of those nerds who went to band camp, and let me tell you band kids are SUPER horny, that isn’t a lie. I lost my virginity at my coed overnight band camp summer trip in 9th grade to a girl who was on her period. It was messy, but she knew what she was doing and I wanted to have sex with her. I didn’t realize how messy it would be, but I also didn’t care.” – Todd, 25

12. “I lost my virginity over a game of truth or dare game with people I met when I was on a spring break trip. The guy was a total asshole though and I constantly regret it. He knew I was a virgin and took pictures because he thought it would be funny to show his friends. It was humiliating and I’m glad I never had to see him again.” – Brit, 26

13. “Very weird situation, but I’m really good friends with my mate and his girlfriend, and they know I’m still a virgin. One night after we’d been drinking a lot he told me to have sex with his girlfriend and he wanted to watch. That night I lost my virginity and now have a huge crush on his girlfriend, but obviously can’t do anything about it. The whole things just super fucked.” – Spencer, 27

14. “My boyfriend at the time wouldn’t have sex with me because he wanted to wait, but I was really eager to lose my virginity so I ended having sex with his older brother. Let’s just say things didn’t end well with that relationship and I’m not proud of my actions.” – Cait, 26 Thought Catalog Logo Mark

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