That’s… A Bad Way To Lose Your Virginity… (15 GIFS)

"Girl did not know it was my first time, probably lasted a grand total of 4 seconds, but the real embarrassing part that only I know of is I never took off the condom, for some reason I just pulled my pants back up and walked her home.

When I came back the condom was gone. Next couple days I’m walking to school and see a condom on the side of the road, I thought that’s fucking disgusting, took me a while to realise it was probably mine."

"He knew he was gonna break up with me before we had sex, and knew that it was something semi-important to me.

Note: We call this “being an asshole”"

"Met her at a drunk college house party. She was experienced, I was not. I tried to go down on her, I was so terrible she laughed and told me to stop. She got on top of me and I lasted about 8 seconds. The whole time, TLC’s “Don’t Go Chasing Waterfalls” is playing on repeat in another room nearby.

Followed by an hour of awkward cuddling and a walk of shame to my apartment downstairs."

"Fooling around outside the clothes in my bedroom but my door doesn’t lock so was afraid to take it any further since my parents were home. There is a 1/2 bath right next to my room so we sneak in there.

Not enough room to bend her over the sink or anything so she sat on the toilet while I kneeled awkwardly to line myself up. Went for about 30 seconds before it became just too weird and awkward so we just went back to listening to music and never spoke of it again."

"She gave me chlamydia. She will forever be chlamydia Cloe in my book."

"I finally worked up the courage to become intimate with someone. Took so long I didn’t lose my virginity till this summer, I’m in my late twenties.

After the fact he tells me he lives with genital herpes."

"I threw up directly onto her seconds after finishing inside her.

She responded by punching me so hard that my nose bled."

"Condom got lost inside me. Guy freaked out, drove me home, and never spoke to me again. It was quite special."

"I had to pay for it…"

"I was a wide eyed freshman in college. I didn’t really know what pulling out was and we didn’t have a condom. She was more experienced than me so when I was kinda close but not done I asked her how to pull out. She’s just like, “I think we should stop.” And that was that for the night."

"First time was in the back of a Chevy Blazer, we were to anxious to do it at each other’s home because of family members being around. But long story short great first time all things considered and the guy who walked by the blazer gave us a thumbs up."

"Cinderella 3 was playing on the Tv. I was 16 it was 2009 or 2010. I’ve never seen Cinderella 2."

"I had to fake an orgasm. I’m a guy."

"I was drunk as fuck and high as fuck. Girl and I were fooling around in the woods. Then moved it to my friends garage. I was awkwardly trying to mash it in when my friend comes in and says “What the fuck are you DOING?” What am I supposed to say? “Do you mind? We’re trying to start a family!”

That was my 16th birthday. Good times."

"Being 23 and buying condoms and a rockstar and the teenage kid behind the counter saying “you’re gonna have a good night ahead of you”"