1. Not the greatest time:
"Long story short, I threw up on his dick and then kneed him in the balls trying to run to the bathroom. We broke up a week later. It was a great time." — Submitted by finleya
2. Mama's boy:
"He got a call from his mom twice and answered both times. They argued while he was inside of me. FML." — Submitted by danilunsford15
3. A hefty mistake:
"Didn’t have a condom and I did not want to get pregnant, so my boyfriend made one out of grocery bags and then taped it onto his dick. Hand to God, worst first time ever." — Submitted by kellyh421092f6f
Editor's note: Please do not try this at home. Plastic bags are not safe/effective methods of contraception!
4. TL;DR Little brothers are the worst:
"My boyfriend and I had been together around nine months. I was 18; he was 20. I went to his house, where he lived with his mom and younger brother. We distracted his younger brother with video games for some privacy and headed into the guest room. He wanted to try doggy style, so I flipped over. As he was getting into position, his younger brother came into the room and asked what we were doing (we still had shirts and socks on) and then proceeded to have a 10-minute conversation with us while my boyfriend was trying to extricate himself from me.
TL;DR: I had a conversation about Legend of Zelda with a 10-year-old while losing my virginity." — Submitted by ebaldwin96
5. Three's a crowd:
"We were both freshmen in college, and we had been together for three years at that point. We lost our virginity while my roommate was still asleep across the room, and we both cried out of guilt after it was over. Thankfully, we’re still together five years later!" — Submitted by tomtoyourjerry
6. Survival of the fish:
"I lost it to my long-distance boyfriend during his second visit to my freshman dorm. There were adjustable shelves on the wall above my bed and the lowest had my pet fish on it. Right after we finished he stood up to get tissues and knocked into the shelf on the wall, spilling fish water, pebbles, and my fish onto me and my bed. This was at 2 a.m. and the commotion caused my very conservative roommates to come running to see what was going on while we scrambled to put on clothes and clean everything up. It was horrific. (Note: Blair Waldorfish did survive the incident.)" — Submitted by ryleight
7. Do not try this at home:
"I tried to do the sexy 'pull your bra off through your dress' and ended up scratching my arm and drawing blood, which slowed things down a bit. To this day I have a faint scar on my arm to remind me not to repeat seduction techniques from TV." — Submitted by overratedbytv
8. Rescue 911:
"My ex-husband and I were very involved in church and were both virgins on our wedding night. Immediately after doing the deed, he began to have a panic attack. Being 18 and inexperienced in life, we both assumed he was dying. I frantically called 911 and an ambulance was sent right away. I fielded the onslaught of firefighters and paramedics in my T-shirt and underwear. I’m sure they all had a good laugh that night!" — Submitted by devonj4f35202b6
9. Spilling the seed:
"We were both virgins, and we tried to have sex but it was so painful I had to stop before he came. I cried so hard that I threw up, and while this was happening he was holding me, saying, 'We’re still virgins until I spill my seed.'
SPILL MY SEED. His exact words." — Submitted by cailsann"
10. A new spin on sexting:
"We’d gone back to his apartment to have a good time. Everything was perfect for my first time: a little wine, romantic lighting, sexy music. As we got into the heat of the moment and I started being a little more ~vocal~ than anticipated, his phone started vibrating. Turned out his roommate could hear us very clearly and was texting him our coitus quotes." — Submitted by stackopancakes
11. The not-so-hot tub:
"I lost my virginity in a hot tub. Probably not the best decision because water is a terrible lubricant and he was hung like a horse. Needless to say it wouldn’t go in all the way, so when we got out to finish the deed somewhere else, gravity took over and I ended up bleeding like crazy all over the place. He was pretty cool about it though, thankfully." — Submitted by mel03
"He watched The Jetsons the whole time, and lasted less than 20 seconds. He then locked himself in the bathroom, upset that he didn’t last longer. I had to comfort him and it was just a terrible experience." — Submitted by shannonw4d32fccf9"
13. Sorry, Mum:
"My mum walked in, low-key screamed a bit, then ran and told my dad." — Submitted by hannywarburton
14. Creepiest roommate award:
"Halfway through, his roommate walked in and didn’t leave. He just sat there and watched. We didn’t realize he was there until it was over. That roommate was weird." — Submitted by amyc69
15. A quick trip to the Creek:
"The theme song from Dawson’s Creek was playing while I lost my virginity. It was over before the first scene." — Submitted by katwoughter
Note: Submissions have been edited for length and/or clarity.