The Mole

"But why must I appear as a woman? Why couldn’t I just portray a gay man working as a waiter?" I was still trying to evade what I felt was a socially revolting task, dressing as a woman. Somehow, it violated everything in my upbringing.
"Because they will have an opening to hire a bar waitress, and we know they will specifically look to hire a very pretty transvestite for the position. We’re already working on it. And believe me, you’d be much safer as a woman there rather than a gay guy. Trust me on this. Most of their clientele aren’t attracted to women."
All I could say was, "WOW!" as I shook my head in futility.
Now I wondered what I’d volunteered for.

"So I’m to become a woman and work the lounge in a gay and lesbian bar, right?"
Bruce nodded. "And transgender. There will likely be other crossdressers there as well. No…Appearing as a guy wearing women’s clothes and ENJOYING it. You don’t need to be a totally passable woman, in fact, we don’t want you to be too good. You’re just a guy who enjoys crossdressing. The owner prefers that kind…guys in drag…Shemales"
"And exactly how do I accomplish this bit of magic? I’ve never done anything even close to this before. How do I start?"

"Not a problem, Tim…remember, you don’t have to be a perfect female impersonator. You’re still a guy, but a guy in a dress, a cross dresser. They accept cross dressers there. Your goal is to convincingly enjoy yourself in that persona, get to know people, and get them to take you into their confidence…That’s where the police work comes in. Work it like you need money to support your expensive hobby of cross dressing and are looking for some easy cash. Do whatever it takes to win them over. Hopefully they’ll draw you into their operation. Somehow, they’re buying and selling stolen property, specifically art work That we know. We must find their sources of goods and their buyers. I’m sure we can manage to get you employed there. Still interested?"