At first it was just for a bet.. now i cant resist dressing up

i made a bet with my roommate that sissy hypnosis doesn't work

She bet she could take it 😂

After I beat the shit out of your son and put him in the ICU,

Lost bet!

I know my cock is hard but i bet you can make it even harder

I lost a size bet with my roommate and he made me wear this,

Sissy Sports Bet

I bet you’re too busy stroking your cock to my tits to even

Lost a bet to my bullies and had to dress up like a girl. Since

Strange Sissy Bet

He won the bet, but you're the real winner here