These People Lost Their Virginities In The Most Awkward And Hilarious Ways

#1 The one with the condom struggles

"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 chemist 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 fucking 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 one's. I thought that was nice of her but I never had thought my penis was above average.

"So she convinces me and we get in my car and drive to the nearest chemist, and then came the second most awkward part, this was a different chemist 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."

#2 The one where he questioned his sexuality

"I was having a house party for my 21st birthday (Late bloomer? Perhaps. I've been the fat guy my whole life... confidence was always an issue for me) with my friends that weren't old enough to make it out to the bar with me. A month and a half prior, I had become friends with a group of girls who really liked to party. I had just started getting into the crazy party drunken scene (with my newly found confidence, I learned I could be the life of the party.)

"One of these girls I had a bit of a thing for, but she was way out of my league. Like way out of my league. But newly found confidence, drunkeness, and the fact that if I "went for it" and was rejected, it wasn't like I was losing a friend from 10+ years ago, I set my sights that I was going to try and get with this chick. We made out a few times, but eventually the night started slowing down, and she ASKS to come sleep in my bed with me.

"I'm super nervous... it's like I was being pulled over by the cops... my drunk just instantly went away and I was just freaking out. Eventually, after making it blatantly obvious she wanted me to finger her and I just kept rubbing her stomach awkwardly, she grabs my hands and forces it into her pants. I awkwardly asked "should I get a condom?" After she replies yes... I think asked her about 3-4 times if she was sure.

"I had been hosting quite a few parties over the past 6+ months, and learned how helpful having a community condom drawer was. Kind of like a give a penny/take a penny system. I didn't want my friends getting pregnant. I didn't want my friends getting an STD. I didn't want my friends getting stains... anywhere. So I reached into my community condom drawer, slid it on, and went to work.

"The first thing I noticed was that it didn't feel nearly as awesome as I had imagined. Like... you spent your teen years fapping and imagining what a vag 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 realise 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.

"While I have my dick in this hot chick... the only thing I'm thinking about is 'oh my god, I must be gay'. 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 desensitising lubricated condom for guys with stamina problems."

#3 The one with the Monica-style organisation

"My girlfriend and I decided we would lose our virginity to each other , so she decided to set up everything before hand because she likes planning things. She likes it SO much in fact, that she told me the date it was happening 3 months before hand, so she could get on birth control, get a nice place to do the deed, have a nice body by working out a bit and so on.

"What I did those entire 3 months was freak out every moment I could about performing,and how fast the date was approaching. I psyched myself so much that when the date finally happened, I couldn't get it up for about 2 hours, and couldn't orgasm the entire night. All I did was get frustrated and tired. "

#4 The one where slow and steady wins the race

"It took a month of my boyfriend putting the tip of his dick into my vagina, me crying due to pain, him getting soft and consoling me before he was able to actually go all the way in."

#5 The one with all the romance

"I lost my virginity to the words "just sit on it".

Yeah."

#6 The one that really WAS that bad

"I dated a guy for 9 months when I was 15. He was 18. I was a virgin for sure, he says he was and judging by how terrible he was at it, I believe him. The day after we lost our virginity to each other he sat me down and said "Last night made me realise....that I'm gay".

"I thought he was joking, then he told me that he met a guy online and was going to move one state over to be with him. He left the next day. I still hoped that he was joking but I was really close with his grandmother and she confirmed that it was true."

#7 The one where he nailed it

"I was an awkward teen barely into my Sophomore year in high school. I found myself in a situation where I was actually getting into the pants of a girl who I thought was my girlfriend.

Now here's the awkward part. I started touching her vagina and eventually tried to insert my finger into it. It became uncomfortable for her and I eventually gave up. That was as far as we tried to go.

"In the coming weeks, some other girls that knew her seem to smile funny when they saw me. Eventually I heard one of them call me 'nails'. I didn't understand at the time but eventually figured it out. I need to trim my fingernails. That nickname stuck with me throughout high school and was even brought up at my ten year reunion.

She ended up being a lesbian and I turned out to be gay. I often wonder if our little experience had anything to do with that."

Thank God it only has to happen once.

#8 The one with the tears

"I have a female friend who lost her virginity to a Mormon. The dude just curled up into a ball after they were done and cried. "

#9 The one with your mum for company

"Home alone with the gf. During the 'act' we heard the phone ring. I let it go (obviously). This was the old days, with land lines and answering machines. The machine picked up. Right as I was about to finish, my mother proceeded to leave a 5 minute message. It was loud. I lost my virginity with my mother's voice in the background. "