I had no idea I was into cross-dressing until Halloween.

Up until then, I hadn’t realized I would be excited by the way a pair of silk stockings would feel against my skin or about how much I’d be into shaving myself until my body was totally smooth and bare, or about what it would be like to slip on satin panties over my stiff cock. 

But I’m getting ahead of myself.

It happened because of a simple suggestion. Sophie, who is one of my coworkers, said that all she’d ever wanted to do for Halloween was dress up as a man, but she hadn’t worked up the nerve.

“Why would you need nerve?” I asked her.

Sophie shrugged and said, “Well, do you think I could do it? I’d really want to fool people.”

I eyed her. She’s nearly... Read More