My first time becoming a sissy
You can see that this crossdressing newbie has never transitioned before. Not that it matters, though - we're sure his first time becoming a sissy will be really fun!
You can see from the smile on his face at the start of this scene that he wants nothing more than to become a beautiful woman. It begins with some makeup application but soon enough it transitions into finding a set of bra and panties that he can wrap his sissy body in. The red lingerie outfit is just perfect for what he wants.
It's a little uncomfortable to begin with, but the experience is taken to a new level when this sissy slut looks down at the body she's created. In fact, the cross-dresser gets so horny that she starts to masturbate at the very idea of being dominated by a man as she embraces her feminine ways. While it might be a first time sissy, it sure as hell won't be a last time sissy!