30 Hilarious Stories About People Losing Their Virginity

No matter how many movies or books we read, losing your V-card is not what you expected. Anyone that has had sex can vouch that losing your virginity is definitely an interesting, most of the time awkward, experience. To get some of the most awkward and hilarious stories, we asked 30 college students to share how they lost their virginity.

1. Confessions to a priest

“It was Halloween 2k16 and I was dressed up as a priest. I had gone to my best friend’s house for a Halloween party and brought these two girls from my rival high school with me. We got to the party and danced for a little bit before winding up in a room surrounded by couches. A couple of my friends had wandered in the room with us.

Someone suggested we play a game of dirty truth or dare so I downloaded the app and we began to play. Five minutes into the game my name came up with one of the girls I had brought. We were sentenced to the bathroom for 7 minutes, but were caught by my friend’s mom after only a minute. After that, I suggested to take it back to my car.

We walked across the street to my liberty wagon and climbed in the back seat. We started messing around and just as she undid my pants I heard someone calling my name. All I could think was, not again. My friends ended up opening the door and proceeded to make fun of us before I slammed it shut in their faces. Scared the moment was gone, I looked over at her. We both said nothing for a moment and then she looked me in the eyes and said, ‘forgive me, father, for I’m about to sin’ before she ripped off my clerical collar.”

2. Campfire music

“It was my first time being a CIT at a summer camp. I wasn’t quite a camper or a counselor, but I thought I was the shit. It was the first night that all the campers had arrived and we were doing a big campfire. One of the counselors came over to me and asked me to go somewhere with her, I can’t remember where but I got up and followed her.

We ended up behind the barn which happened to be the other side of where everyone from the camp was. She had asked me to fuck her and I obliged. Little did I know everyone could hear us. The owner of the camp came over and started screaming. My face turned white and I just stared at her with my pants down looking like a deer caught in headlights. Scared of the repercussions I ended up throwing up all over her and being sent home the next day.”

3. Not the right hole

“My girlfriend at the time and I had decided to finally have sex. It was both of our first times. We were in her car and I thought I was in her, but it turns out I was between her and the car seat. She never said anything. She just sat there watching me fuck her car. That night I thought I had lost my v-card to my girlfriend but it was actually her car. We tried again a week later, this time in a bed, and I succeeded.”

4. Church is definitely a place of worship

“It was the middle of the night when I got a text from this guy I was seeing. He wanted me to come pick him up. So, I got in my tiny VW Jetta and drove the 20-minute drive to his house. He got in my car and immediately assaulted me with his tongue. We frantically made out in his driveway before looking for a place with a little bit more privacy. Eventually, we stumbled upon a dark, empty parking lot, behind a church. We started making out again before moving to the back of my car. Let’s just say that night ended with a stiff neck and a lot of screaming out for God.”

5. Sibling bonding

“My brother and his girlfriend walked in on me having sex with our next-door neighbor. They just stared in shock for a moment before laughing and walking away. They left the door open, but it didn’t stop us from finishing.”

6. Never mix work and pleasure

“I was working at a small mom and pop bakery in high school. The owners had a son and he would always work the same shifts as me. He would flirt with me constantly and one night we were both working the closing shift and we took the flirting a bit too far. I ended up covered in flour and fired the next day.”

7. Daddy’s little girl isn’t so little anymore

“It wasn’t during the actual act of losing my virginity that anything funny happened but what happened after. My boyfriend and I had sex one day when my parents weren’t home. We cleaned up everything and went on with our day. Later that night, my dad walked into my room and held up a torn foil package. My face paled. “What is this?”, he asked. I gulped before saying it was for a friend. He obviously didn’t believe me, so he called my boyfriend over. He sat us down on the couch and asked us about it. My boyfriend’s face turned bright red and the veins on my dad’s neck were popping out. My dad took a deep breath and then proceeded to give us an hour-long sex talk hoping he could scare us from ever trying it again.”

8. Stage fright

“It was two days after my 18th birthday and my boyfriend who was in college had come home for the week to celebrate. I took the day off from school and drove over to his mom’s tiny two-bedroom apartment. His bed just happened to be in his mom’s room, but that wasn’t the awkward part. We honestly just skipped the foreplay and went straight to getting naked. In hindsight, that was a bad idea because the whole time during sex he couldn’t keep it up. All I could do was lie there while he kept apologizing.”

9. Night out gone wrong

“It was my first week in college and I was ready to get it over with. My friends were all making fun of me for still being a virgin, so I was set on going out and finding someone to take it. We went to a club within walking distance from my dorm and we met a few girls. We were all drinking and having a good time. I brought one of them back to my dorm and we had shitty drunk sex while my roommate slept. After we were done she started to gag and threw up all over me, twice.”

10. The more the merrier

“So my friends and I had decided to spend the day relaxing by the pool. My friend had a community pool in his neighborhood so we decided to go there. When we got there, I looked around and spotted this incredibly hot girl. I pointed her out to my friends and we decided to try and get her attention. We waved our arms around and jumped in the pool. Eventually, we went over to talk to her. After a little bit, we had to go, but I told her we would be back later that night for some more fun if she wanted to hang out again.

So flash forward to that night when my friends and I were sitting in a hot tub with the girl from earlier. We hung out and drank for a bit before one of my friends walked off with the girl. I hadn’t thought anything of it until they had been gone for quite a while. I decided to go see what they had been up to and stumbled on them naked on the sidewalk. Completely intoxicated, I wasn’t thinking and asked them if I could join. After I spoke I immediately regretted it until the girl surprisingly said yes. And that’s how it happened, I lost my virginity on the sidewalk of a neighborhood pool in a threesome.”

11. Allergic reactions

“I was 16 years old when it happened. I had gotten my first fake ID and gone to a club with a few of my friends. We were dancing and drinking and I saw this really hot girl on the dance floor. My friends saw me staring and dared me to go up to her. Never wanting to deny a dare, I walked over to her and asked her to dance. She looked me over and to my surprise, said yes. We danced for a while and I bought us a couple of drinks. When the club called last call she asked me to walk her home. I was so excited I sped walked the two blocks to her house. She asked if I wanted to come in and of course, I said yes.

She pushed me onto her couch and straddled me. After some foreplay, she placed a condom on me and started riding me. My dick started to burn, but I pushed through it till I finished. After we were done I quietly got dressed and walked to the door. I was itching badly and my heart started beating fast and before I knew it I was falling to the ground. The girl from the bar ended up calling 911 and I left her house in an ambulance. That was the night I lost my virginity and learned I was allergic to latex.”

12. How to save money on a hair cut

“I was over at my girlfriend’s dorm room trying to help her lower her bed, but it was too hard and eventually we gave up. We decided to cuddle up and watch a movie. It quickly turned into more and we started having sex. All the sudden we were falling and she was screaming. The bed had finally dropped, but her hair got caught in the hinges. We had to cut her out.”

13. Front row seats

“When I was 15 my brother was three and my parents would hide a Nany cam teddy bear in the house when the babysitter would come over. Not realizing they had left it in their room, I brought my girlfriend there. She told me she had something for doing it in a parent’s bed and I knew my parents would be out that day. I lost my virginity in my parent’s bed. When they got home I guess they were looking through the footage and I ended up grounded for three months.”

14. Going viral

“I was working on a school project with this girl from my class and one thing led to the next and we weren’t doing homework anymore. The next day I found out she had a live stream on her blog going and everyone saw me lose my virginity.”

15. Dogs don’t have nine lives

“It was valentine’s day and my parents had gone out for dinner. I invited this guy I’d been fooling around with over and things had finally gone further than heavy petting. Just as he was about to cum, the front door opened and he jumped off me. We panicked and quickly got dressed. He decided to try and climb out the window, but lost his footing and fell. He broke his leg in three places and my dad had to drive him to the ER.”

16. Frenemies?

“My friends dragged me to a party my freshman year of high school. I didn’t want to go and figured alcohol would make that night better. I drank like half a bottle of vodka before winding up stairs with some random guy. The next morning, I woke up naked and next to the school asshole player.”

17. Off to a rocky start

“My family had decided to take a cruise right before I left for college. I wasn’t really excited because I wanted to spend time with my friends before we left but I was determined to make the most of it. One of the days that we were docked, my family had decided not to wake me and left the ship without me. Stuck on the boat by myself, I went looking for fun. I went down to the pool and was tanning when I noticed a few guys from my high school. They looked over at me and I waved. They signaled for me to come over, so I got up and walked over. We started talking and hanging out.

After a couple of hours, I decided to head back to my room and one of the guys offered to walk me back. I let him and he kissed me as we got to the door. Things escalated quickly and before I knew it I wasn’t a virgin anymore. As he was getting off of me, the door opened. I looked over his shoulder to see my parents and little brother staring right at me, mouths on the floor.”

18. Up in flames

“This guy had asked me over to his house. He said he was cooking dinner for us and that his parents wouldn’t be home. I got dressed up and headed over to his place. When I got there, he shoved his tongue down my throat and walked us to his bedroom. The night ended with the fire rescue coming to put out the burnt chicken we had forgotten on the stove.”

19. It’s okay to ask questions

“It was my first time and the guy asked me to ride him. I had no idea what I was doing and thought I was supposed to just grind with his dick in me, boy was I wrong. I ended up grinding so hard I sprained his dick. Who would’ve thought you could sprain someone’s dick?”

20. Times up

“One night, my friends and I had decided to stay in and have a girl’s night in. We were drinking and playing cards against humanities when we all got hungry. Everything was closed, but I remembered I had pizza rolls back in my dorm. So, I offered to walk back and get them. They asked if I wanted them to come, but me being stupid and drunk I said no. I walked back and ran into my RA, literally. I fell back but he caught me. He asked if everything was okay and I said yes.

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We started talking and he walked with me down to my room. I walked in and told him he could come in so he did. We kept talking as I walked to the kitchen and put the food in the oven. We walked back while they cooked and eventually wound up on my bed. I kissed him and he pulled back at first, but then kissed me. We finished just as my timer went off and we both left my room and went our separate ways. I walked back to my friends with the pizza rolls and never spoke to my RA again. Move out day was awkward as fuck.”

21. 15 going on 30

“I met up with this woman I’d met on tinder. She was probably 30 or so and I was about 15 years younger. I looked much older than I was and she had no idea. We were fooling around in her house when she let me have sex with her. I could tell she was enjoying it and I mentally high-fived myself. When we were done she told me I was better than her husband and I told her I was 15.”

22. Liar, liar pants on fire

“My girlfriend and I were fooling around in a hot tub and we had sex, or so I thought. I found out a month later she was using her hand and a jet and that I was still a virgin. I was so pissed off I went out and found some girl to have sex with. It was awful and I felt awful for cheating on my girl. I went to tell her what I had done, but before I could she broke down and told me she was scared to have sex and that’s why she did it. I felt like an asshole and decided not to tell her. A month later we finally had sex and she still doesn’t know she’s not my first.”

23. Jungle gyms aren’t for children or teenagers

“This guy in my neighborhood asked me to meet in the park across my house to smoke. It wasn’t anything out of the ordinary, so I went. We were fucked up when he thought it would be fun to fool around on the jungle gym. We started messing around and things went further than planned. His footing slipped and we slid down the slide. I had road rash all down my stomach and my ankle was bruised. I figured it was time to go home, so I hopped the fence and landed weirdly on my already hurt ankle. Turns out I tore a ligament and broke my ankle. I told my mom I slipped in my messy room.”

24. Sleepover + 1

“I had some friends sleeping over and we were all hanging out on my bed when my FWB popped by. He stayed and hung out with us for a while. My friends fell asleep in my bed, but JT, my FWB, and I were still talking. He kissed me and we started fooling around. I ended up letting him go all the way while my two best friends slept next to us.”

25. Seeing stars

“My girl and I were leaving a restaurant when it started pouring. We had no umbrella and were parked like a mile away. We ran through the rain and got to my car where we decided to take our clothes off. I look over at my girlfriend who’s in just her bra and underwear and couldn’t help but kiss her. She took off her underwear, pulled my boxers off, and started to ride me. She was going up and down when she hit her head hard on my roof. I checked to make sure she was okay, but she wasn’t answering. She was knocked out cold. I had to call an ambulance and explain to her cop father what happened. I was banned from the house for 3 months.”

26. Too much gas, not enough foreplay

“My boyfriend of three months and I were both virgins and decided we wanted to lose it before college, so we planned a whole night. Candles, rose petals and even the sappy music. When the night finally came we were so excited that we rushed into it. I wasn’t wet enough, so it hurt like hell. He was moving so slow and I just wanted it to end, so I yelled at him to go faster. The reason he was going so slow wasn’t that he was scared of hurting me, but he had to fart and didn’t want to ruin the already ruined moment. When he sped up he farted loudly and I just laughed. I thought okay this can’t get any worse, but the farts kept coming and eventually he got up and held his ass as he ran to the bathroom.”

27. Pick your roommates wisely

“I was supposed to be studying with this girl, but she had other plans and I wasn’t going to stop her. We were in a pretty compromising position when the cops busted through my bathroom looking for my stoner roommate. The cops were questioning us as I was still in her. She was mortified and started panicking. She pushed me off of her and walked out of the room naked. A second later, she came in, grabbed her clothes, and left. So did the cops.”

28. Not the toilet

“It was my first time so I was expecting to cum quickly, but not with in a minute. It was just too soon and I freaked because it didn’t feel as good as I thought it would. I pulled back and noticed a yellow stain on the bed. I then realized I had peed in her and quickly got dressed and left before she could say anything.”

29. My mom’s best friend

“My parents were having a party with all their friends over. I was stuck there bored out of my mind when one of my mom’s best friends walks into my room. “Hi Grace,” I said and she stumbled over to me. “You know I’ve always wanted to do this,” she said before she kissed me. She was hot for a 40-year-old woman, so I went with it. The whole time she complained about her husband cheating on her as we had drunk sex. I never told my mom and we still fuck occasionally.”

30. GBF

“A new family moved in next to us and they had a son about my age. He was hot as hell and his room was across from mine. We could see into each other’s rooms. We started talking through small waves and smiles. After weeks of no progress, I decided to try something bold. I was going to leave my curtains open after my shower.

So the next day after my shower I walked into my room naked and walked in front of the window. I saw the boy staring at me and I just smiled and closed my curtains. The doorbell rang and I slipped on my robe and went to answer the door. ‘Hi. I’m Jack.’ The boy next-door said before kissing me. He undid my robe and fucked me in my kitchen. When we were done he got up and said, “okay I’m definitely gay”, before walking out of my house. Now he’s my best friend.”

Do you have a hilarious story about the time you lost your virginity!? Share in the comments below!

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