Your Worst Jockstrap Horror Stories

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When I was in college, I called a phone sex line one night (this was pre-internet, so phone sex was a somewhat-viable option for the horny teenager) and, after navigating through 18 different voice menus promising me hot action, I got hooked up with a live lady on the other end. I asked her what she was wearing. Of course I did. That's standard phone sex etiquette. And then, when she was done revving me up with an imaginary teddy, she asked ME what I was wearing.

"Urrr durrr I dunno"

"Do you play football, Harvey?" (Harvey was the name I gave her)

"Yeah, kinda."

"Do you wear those little what do you call those strappy things?"

"A jockstrap?"

"Yeah. Do you wear a jockstrap?"

"Yeah. I'm wearing that now actually." (Lie.)

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Your Worst Jockstrap Horror Stories