1. The double whammy.
"Me and a guy I'd been seeing grabbed some condoms, put on a porno, and followed what the actors were doing. But the porno we were watching used spit for lube, so we did too. The pain was nothing like I had ever felt before. As he pulled out, his penis had changed colour to a poop brown. As it went all over the bed, the smell hit us and he was sick all over me."
2. The garden toilet.
"I slept with a guy I’d been seeing for a month. After the initial pain, I got into it and enjoyed it a lot. The tragedy occurred later on that night, when I realised that I had to do a number two. He said the toilet in his guest house (where we were) wasn’t working. The one in the main house was fine, but he had rented out the main house and I couldn’t go in that late, so I ended up taking a dump in his garden."
3. The surprise baby.
"When I was a freshman in college, I went out with this guy. We went to a football game, grabbed some food, and proceeded back to his dorm room. I went to the bathroom and when I returned, he was wearing nothing but a diaper and asked me to treat him like a baby. I was so freaked out that I grabbed my things and left as quickly as I could."
4. The log splitter.
"After pulling down his pants, I immediately knew that I was in grave danger. His penis was not the six and a half inches that I was promised, it was an eight-and-a-half-inch log splitter. The penetration nearly blinded me from pain. Afterwards, he high-fived me like a true gentleman, told me that he liked my teeth, and drove off into the sunset."
5. The non-invasive penis.
"This guy had been boasting about how sexually experienced he was, so I figured that he’d make me feel more comfortable. He ended up getting inside me once for about a second, and then thrusted between my cheeks for the rest of it. He expected me to think that he was actually inside me the whole time, as if I wouldn't feel that he wasn't."
– Ryan Wildgoose, Facebook
6. The exorcism.
"When I got home from getting my cherry popped, my mother’s church friends were there. I started to panic, sincerely believing that they were there on an intervention from God and wanted to exorcise the gay out of me. I kissed my mum on the cheek as I entered the house, and was terrified that she would smell his dick on my breath."
7. The nervous poo.
"I decided to put my anus in the hands of Grindr and met up with this guy. I actually had a really good time, until I realised mid-penetration that he was married to a woman (his wedding photos were next to the bed). Due to this realisation on top of my pre-existing nerves, I got a hard pit in my stomach and he proceeded to literally fuck the shit out of me. It didn’t make a huge mess, and he was really cool about it. However, I didn't meet up with him again."
8. The wrong name.
"I was working backstage for a play. There was an afterparty where I got too tipsy and lost my group, so I started talking to a guy about how we were wearing matching shirts. We started making out and he led me behind a tree, where I got my first blow job. We then got in his truck and ended up having sex in the parking garage of the theatre. He called me 'Ryan' twice."
– Kevin, Facebook
9. The confusing pillow talk.
"My first boyfriend was going to college in the town where I lived, so we did it in his dorm room. I don’t remember much of it but then after we finished, he turns to me and says, 'You might have to fart afterwards.' I was so confused."
10. The caring boyfriend.
"It was my first year at uni and my boyfriend and I decided to give anal a go. It felt like a knife jabbing into my ass. I went to the bathroom to clean up and felt what I thought was lube dripping from between my legs. When I looked down I saw it was actually huge splats of blood. I fainted and the next thing I remember is my boyfriend waking me up in a cold shower attending to the cut across my temple and a bag of frozen peas on my ass."
11. The Craigslist taxi driver.
"I poked around on Craigslist until I found a guy to do the dirty with. He told me to meet him at the public library and that he would be driving a yellow car. When I got to the parking lot, there was only a taxi there. When the driver waved, it hit me that this guy had responded while he’d been driving around in his cab. As my first time, I’ll tell you that bigger is not the way to go. I walked funny for a week."
12. The aspiring singer.
"The first time I had to give oral sex I literally said, 'It looks like a microphone, let me sing into it.' I’m mortified to this day."
13. The down and dirty.
"We had nowhere to do it so we ended up fucking in the dirt in the cinema car park. Needless to say the knees of my jeans got covered in dirt. My mother's face when she picked me up from the train station afterwards was a picture."
– David Eden, Facebook
14. The pizza topping.
"It was on the hood of a car at night to a guy I met six hours earlier when he delivered a pizza to my house. It wasn't too great."
– Alex Williams, Facebook
15. The extracurricular activity.
"It took place at a theatre camp. We flirted heavily during the day and then I snuck into his room that night. We made out for hours, but his facial hair was so aggressive that I made him go shave. After he came back, we got naked, and he just sort of did a resting pose while I awkwardly thrusted him from behind. I remember staring at the clock, fixating on how late it was and how I should be in bed."
16. The long and painful walk home.
"He was just over 10 inches and thick. Needless to say I could barely walk the next day, and he lived on the complete opposite side of campus to me."
– Rex Gregory, Facebook
17. The stubborn quest.
"I booked a hotel to spend the night with a well-endowed man I’d met on the internet. I spent the first two minutes hovering after the tip went in debating whether I should carry on or quit while I was ahead. Fifteen minutes later and I had never resented my stubborn nature more. What followed was a mix of awkward exchanges, including the realisation that a soapy finger was not enough to prepare."
18. The book bag dash.
"I had just finished my gym class and was chilling in the sauna when I noticed this guy giving me the eye. We started talking and he undid his towel so I did the same. Next thing I knew we were all over each other, only taking a break so I could run to my bag and grab a condom. I topped him and lasted less than five minutes."
19. The valiant effort.
"My roommate set me up with one of her friends. He came over and we had dinner and a lot of wine. After dinner we made out and moved things to the bedroom. About 10 minutes later we both realised how drunk we were and fell asleep in each other’s arms. It was a valiant effort!"
20. The breakup.
"I was so nervous during my first time that while we were doing the deed, I threw up all over his bed. We broke up a week later."
Note: Submissions have been edited for length and/or clarity.