You are asking the right ladies when it comes to ideas for how to dress like a sissy. My opinion though is that your friend that you made the bet with might have some ideas of her own. If I won a bet like that I would be all over dressing up my friend.
Have her call me Zach, I will guide her in exactly what needs to be done to you!
Mommy Rebecca
“You don't appreciate a lot of stuff in school until you get older. Little things like being spanked every day by a middle aged woman: Stuff you pay good money for in later life.”Emo Philips
