14

"How about being disappointed in myself. I got on top, flipped my hair confidently, put his dick in then realized I had no idea how to ride it. That was my first time and I never realized it’s not instinctual.

The guy tried to teach me for like 5 minutes. He said do it like I was twerking but I could not twerk for life. It was so embarrassing. In the end he just gave up and told me to lie back down"

15

"Was invited over to a beautiful woman’s house to chill when I was naive and stupid and young. She initially initiated some foreplay but soon realized just how inexperienced and innocent I was and welp, I was sent away.

Never even occurred to me what she really wanted until it happened and I froze like a deer in headlights."

16

"Finger up the bum. She never asked or said she was going to do it, she just pushed the full thing up there with no warning. Nearly blinded her in one eye with my willy"

17

"I worked hard for weeks to knock boots with the hot chick at work, finally the day came and she smelled terrible down there. I finished the job tho, and did it a second time to be sure and yea it was pretty bad the second time too."

18

"My wife came home from shopping one evening. For some reason I kissed her hello, which was unusual for such a short trip away from the house. I don’t think she expected that because I tasted cum on her mouth."

19

"Getting my clit bit."

20

"I had a man take off his pants and then start crying about being uncircumcised. I ended up comforting him for half the night. Very confused though because I didn’t bring it up or say anything. Guess it was just on his mind?"

21

"Back in the mid 90s I fell in love with a girl in 7th grade. She moved away and we lost contact. Reconnected in our mid 20s and planned a date. We drank, we ate, we had a great time. We go back to her place and we start kissing and undressing and what not.

Im about to show her what she’s been missing out on all these years when I went full whiskey dick. Never hooked up again."

22

"Eating whipped cream off genitals. Those are flavours that do NOT go well together."

23

"Guy had poor, naive, college-aged me convinced he was truly an amateur porn star. Bragging to my friends that he’s gonna pick me up and we’re gonna hook up, after weeks of him sending me his videos and telling me all the things he’d do to me.

Picks me up. Barely grunts a hello. Pulls into an empty parking lot, slips a condom on, tells me to get in the back, and just…slams in dry. Thank god for the condom or I think I would’ve had some serious vaginal tears. He came in less than 30 seconds and then drove me back to my dorm.

My roommate/best friend was SO confused on how I was back so fast, and after explaining it, we laughed our fucking asses off making fun of everything he’d said. We still laugh about it to this day."

24

"I was going down on a girl from behind and she done pooted in my eye. Told a friend about it and I’m now known as the Pink eye booty bandit."

25

"When a girl fake moaned in my ear, shit was so cringe I almost wanted to un-fuck her."