Middle schooler to friend: So, have you ever had anal sex with your mom?

Brighton, Massachusetts

Overheard by: Holly

Redhead punk: Oh, God, the first guy I ever had sex with did that to me… Well, actually, that’s not true. He took my technical virginity. I actually lost my anal virginity first to another guy.
Blonde hipster friend: [Silence.]Redhead punk: Yeah. So anyway, what happened was–
Blonde hipster friend, suddenly eating vigorously: –Mmm, French toast!

Lansing, Michigan

Overheard by: lost my appetite

Queer: No amount of chocolate or Fosse will bring back my ass virginity.

Indiana University
Bloomington, Indiana

Overheard by: spunky

Chick: … And he was so dorky that he, like, mistook my ass for my vagina and he started fingering it, and I was like, ‘Oh, he’s a pro,’ but then I realized and was like, ‘… Oh…’

Overheard by: overheardatyale

Girl #1: I fucked in the ass last night for the first time.
Girl #2: Did it hurt?
Girl #1: Nope! But this morning when I shit it did! I think my hole got bigger!
Girl #2: That is sick!
Girl #1: You’re just jealous!
Girl #2: Maybe a little.

Augusta, Georgia

Female Mets fan: I’d let the whole infield fuck me in the ass with no lube if it meant they would win the World Series.
Friend: Classy, Michelle, real classy.

Braves-Mets Game
Queens, New York

Overheard by: aaron

Bar-hopping frat boy: She was begging me for a cab, not to put it in her poop chute.

Overheard by: clinton

Frat boy #1: Dude, if I buy anal lube can I call you ‘Baby’?
Frat boy #2: No… You’ve bought anal lubricant before, right?
Frat boy #1: Yeah.
Frat boy #2: Yeah, that’s what I’m saying — we’re experienced.

Overheard by: the ear

20-something girlfriend, pointing at “exit only–do not enter” sign: I should tattoo that on my butt.
20-something boyfriend: But then you would be single.

Lincoln Park
Chicago, Illinois

Flamboyant gay guy #1, whispering discretely: I'm going to do you so hard when we get home.
Flamboyant gay guy #2, not whispering: I'm going to shit in your mouth.


Overheard by: MB