Sissy School

I would love to be transformed by you!

My fantasy has always been the sissy that is made up to make it painfully obvious that I'm a boy that is being compelled to dress up like a sissy for any number of reasons. It's the teasing and making fun of me that excites me. But it is important for there to be some kind of emotional connection as well. I like to believe that the teasing is for my own good and my Mistress really loves me and is only doing what I need.

I can relate to that. I found that once I got a handle on what styles and colors to wear, and skill with makeup. I liked being recognized as a male dressed as a woman.

Maybe that is why it is so difficult for me to "let go" and act feminine. I would like to have a natural, carefree femininity though.

It's like there are too many obligations, whether it be work, cupcake, or any number of commitments that mean there is no way, in reality, that I can let my feminine half be completely free and open. That sort of sounds like what you are saying too?

That's part of it, I am a guy with typical guy interests. Though I would prefer to go to the mall than some sports event. I've tried hard to be believable as a woman, but seem to have a mental block to where my femininity is contrived. The closer I got to passing, I found I liked being "read". As if deep down I don't want to "pass". Yeah, it's weird.

It comes very close to what's the point of being a sissy if you just look like another girl