So uh, I heard about the bet... uh huh, I gotta say I’m kinda excited about it... I mean, you know way more about football than him... there’s no way my boyfriend is gonna win... you beat him every time. Did he really say he’d wear any girly stuff you pick out for a whole year? Do me a favor... after he’s trotting around here in his maid uniform serving the guys snacks at the get together... make sure you bet him something fun for ME like uh... make him watch his girlfriend blow the winner in front of him while he sings “I’m a little teapot”. Charlotte Stokely Categories: Sissy Training, Feminization, Crossdressing, Humiliation, Cuckolding, Latex Leggings, Loser Symbol.