Schoolgirl babysitter

[Ali]

"You'd like to do what with me? Ha ha! Your mother told me you might be a naughty boy, and said I could spank your bottom for you if I wanted to. She also told me that you have a pair of pretty frilly panties on under your dress. Do you? Do you have a panties on under your dress? Why don't you lift up your dress so that I can see? You may only be a year below me at school, but to me you're just a little sissy. I'll spank your bottie if you're naughty, but that's as far as any physical contact will go. And in any case, my boyfriend will be here soon. I can't wait to see what he thinks about a little sissy like you...!"

[Ali]

Did you ever have a babysitter as an older child, minisissyboy?

Being left in the charge of a girl who is at your own school, when you've been punished by being made to wear little girls' clothes, was an exquisitely humiliating experience.

[Ali]

I'm sure it's a lovely dream. I still reminisce about it. But at the time it happened to me it was exquisitely humiliating.

[Ali]

I think I might like to be spanked by a pretty baby sitter like that.

Being stripped off and spanked by your babysitter is an exquisitely humiliating experience, especially when she's younger, or not much older, than you.