by AdamZasse
It's a fine story, but people on this site care more about the fact that this is heading towards crossdressing than that it is a first time experience. At least stick a thing telling us at the top of the story, please.
I admit, your premise has me curious. I did find it distracting how you kept referring to him as "Jacob Carlotti" throughout instead of "Jacob"... unless there is a plot device, it gets annoyingly distracting very quickly. Actually, it gets distracting even if there is a plot device to it. Good work, though, I like your style.