Would make those Rugby lifts a hell of a lot more interesting if your teammates knew just how much you enjoyed when the shorts dig in a little extra on those lifts ;)

Maybe - but then I’d be tempted to test the theory and yank them up to see how quickly the leg holes pop out

Nothing says freedom like stripping to some tighty whities and drinking beer outside with the boys on a warm summer night

That’ll happen right about the time your Chicago Bears and Hawks both make the playoffs during the same year — so hmu in 2040’s if this app is still a thing ;)

Is that what you said to @wedgiekingt.bsky.social before you ended up like this?

If so, then I can’t wait for you to show off more of your nice jock ass… I mean skills ;)

Turns out the rumor wasn’t true. Guess there wasn’t any discussion w/ the bullies at all as the rules clearly state anybody caught with TW’s on Wednesday shall be legally encumbered to receive a wedgie.

Exclusions to the rule apply if one started the day with a self-administered chair wedgie.

10/10 page and videos truly some legendary viewing materials. So glad you got an OF page - the last time I was this excited about wedgie content was viewing the pictures in the wedgiemen .com folders (which I believe I have you to thank for as well)

Rumor has it the bullies found out and are having a board meeting to decide the appropriate handling of your TW waistband on a Wednesday