These 29 People Lost Their Virginities In The Most Awkward And Hilarious Ways

Having your cherry popped, finally getting that D wet, rounding home base — yep, your first time in the sack is a huge (awkward, uncomfortable, funny, embarrassing, nerve-racking) milestone in life. When you’re younger, you dream of the night when you’ll lose your V card. It was always going to be with your boyfriend that you loved very much, you would feel ready and secure, and you would both come in ecstasy at the exact same time, cuddling all of your previous fears away, and staying together forever and ever and ever.

HA! Yeah, right.

Virginities are taken and lost and misplaced and left in the backseat of your mom’s car. There are no church bells or sappy piano music crescendos — only some shitty country song on the radio, a dude named Chad who you met through your friend’s older brother, a squeaky futon mattress, and a mind racing with an infinite amount of sexual questions and concerns.

These 29 people lost their virginities (or took someone else’s) and it was cringe-worthy in the best kind of way: