The Mole

You’re an experienced police officer. You’re young and unattached so there’s no wife or significant other to distract you, you’re not very tall, yet you are very slender and well proportioned, and forgive me, but you don’t appear overly macho so we feel you’d make a plausible and attractive transvestite, one who wouldn’t appear out of place in such an establishment.

Bottom line, you fit the profile of what we’re looking for. Working there, you’d be able to glean lots of information as would any waitress in a more traditional establishment as you mentioned earlier. Even a female officer posing as a lesbian wouldn’t get the reaction we need. You see, it seems that the owner of this place has a thing for transvestites…pretty ones. We want to attract who we think is the leader of the operation and we’re reasonably sure he’s the owner. Now, unless you know of any genuine transvestites in the department, someone we may have missed, we’re asking you to perform the task."

At age 28, I’m only 5’8" tall, I keep trim and am slender at 137 lb., my hair is jet black, straight, and very long. It’s worn in a bun as regulations permit, which these days of EEO rules, is allowable for minorities. I’m of Hispanic heritage and have always have long hair. It is my culture, my parents said. And I’ve been told by many that my facial features and hands appear soft and almost feminine. That comes from my mother’s side, I guess. Often, my effeminate features are an asset to help defuse a situation. I don’t give the illusion of a macho hard-ass looking to kick butt. For that same reason, female cops have an advantage. At times, I’ve even been mistaken for a lady cop.
Honey is always more effective than vinegar in catching flies, my Grandma said.
I learned that Bruce had searched the entire department’s files for a suitable candidate and he felt I was the best choice to pose as an attractive transvestite, one who could function in the position they hoped would extract the information they sought yet be able to take care of himself in case of problems. It only remained to convince me to attempt the gender bending role.