But with her it was different. She has been a girl a lot longer than she was a boy (her parents were very supportive and basically let her dress how she wished starting in middle school) So with her not only did I have a willing partner. But I had a coaching and supportive partner to show me how to sit. How to walk. How to be basically. She never really pushed me to be feminine. But I both enjoyed how I felt, how I looked, and basically had a confidence I didn't have before. Most of our sex was now with both of us dressed. And it was mostly gentle love making. Yeah of course there was a few wild nights of just fucking. But mostly it was beautiful.There was one night in particular that I brought home one of my female friends. The three of us spend a few hours talking about stuff. Until the she (my friend) asked about us. I basically blatted out about my new found femininity.My friend right away, instantly asked me to get dressed. I guess I forgot to mention me and her had kinda dated. Trudy was all smiles and was happy to see Jenny. She complimented her on how great she looked now that she was out of the business.“No, Trudy, I am still in the business. That’s why we came to see you. We need your advice and help in finding some new girls.”I got that intimidating scowl again from Trudy as she said, “So pretty boy, here is your pimp now?”“No, he is my boyfriend and Business Manager. I decide who my clients will be, not John. And don’t for a minute think that John is forcing me to be a working girl. This is what I want to do. It is what I like doing. He only makes sure my money is invested properly and that I don’t spend it on crap I don’t need.”Trudy glanced at Ted and Carl and asked, “What’s with the muscle?”“Bodyguards for me and any girls we hire to work for me. Let me assure you that any girl working down here will be much better off working for me.”For the first time tonight, Trudy sounded genuinely impressed. “You can afford bodyguards?”“That and a lot more with.
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