The Mole

The training went well. We broke for dinner and actually went out in public to a restaurant to help develop my confidence. Deb even forced me to order my own meal. Scary at first, but I noticed nobody seemed to care about this lady with the low pitched voice. Of course, I was speaking softly and smiling a lot with lots of eye contact. Deb complimented me on my feminine mannerisms. I was trying hard.

Day three, I wore a short skirt and a blouse with a low, revealing neckline and a lace trimmed bra which showed. Again, the playacting centered around the gay bar scenario. Deb did whatever she could to tease and harass me as a drunken patron might do. She also tried to portray a "hands -all-over" manager. I did well to thwart the advances in a non-hostile manner, but I also really enjoyed the physical interaction with Debbie with whom I had become deeply attracted. We engaged in a lot of horseplay and I stole more than a few kisses which forced me to refresh my lipstick frequently. By this short time, I had adjusted to applying and wearing makeup and rather enjoyed the appearance of it on me.
It was a real challenge to maneuver in the short skirt yet maintain feminine modesty but I quickly learned. By the end of this last session, I was exhausted and Deb was convinced I’d do well in my new identity. She contacted Bruce and was given the okay to proceed with the plan for me to seek employment. Deb was to be the liaison for Bruce and I and cover me in case of trouble. I would be unable to carry a weapon, for obvious reasons, but she was armed. She was to pose as my "roommate and best friend. But while I was at work, I was on my own."

I was still very apprehensive about this whole matter, but then, I was only pretending to be a transvestite, not a real woman. So why worry? I figured I might as well enjoy the experience.
I entered the sleazy looking lounge, oddly named "The 19th Hole," and asked to see the manager. These places all appear dank and sleazy in the daylight, smelling of stale beer, I noticed. It’s like opening a dark basement.