The Mole

"But only as much as a transvestite needs to know, remember. I’m not going for a sex change."
"Oh sure, but you must remember, tv’s enjoy what they’re doing. They derive great pleasure in presenting as women. So you gotta start to enjoy this. And I mean, openly. So far, you’ve been very reserved. Like it’s an obligation."
"Well, you know, it is an obligation! This isn’t my choice of lifestyle. It’s only a job, even if it is rather interesting.
So now tell me, Deb, what’s your impression in seeing a guy like this? You’ve been quiet too."

"Since you asked, frankly, some guys look absolutely pathetic in drag…they’re a parody of women and a disgrace. But in your case, I must say, you are extremely passable and very pretty as a woman. No, I’m not offended, in fact, I’m flattered that you look so good and are actually willing to do this."
"So, does this make me less of a man to you?"
"Oh, so that’s what you’re worried about? Well, I obviously don’t see a man here now. But remember, I do know what’s under that dress. Manly? no….sexy? You bet!
Looking beyond all this, I see you as a gentle person, and a darn good sport. Even if you really enjoy this, I see a man in tune with his feminine side. That makes him a better person in my mind. Is that what you wanted to know?"

I was relieved with that disclosure and indicated as much. I may resemble a female at this point, but I still have my male ego, and it is fragile. And I wanted to be attractive to Deb as much as that would be possible in this role. I want her to like me more than just in a professional way.

Debbie and I began the training session in womanly mannerisms which continued into the evening, breaking only for a Pizza dinner, which was delivered. She taught me to sit in a skirt, stand, walk, all under various conditions. She coached me in speech…patterns, vocabulary, gestures, and eye movements while talking, female body language, all very subtle, avoiding showing too much exaggeration like a theatrical drag queen.