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She sent me back in for anotherlarge glass of wine for both of us. When I returned with the glasses, Iknew we were in for a serious discussion. I lit a Misty and took a dragas Brenda started talking.Brenda said that she was sure it was strange and maybe a little bituncomfortable living in a transition state. She told me that she hopedeventually that I would finally take the final step into full womanhood24/7. I asked her what she meant by that even though deep down Iprobably knew. She said that at the very least it would involve gettingrid of all my male clothing and behavior and live as a woman all thetime. She said that my new weekend job would greatly move me toward thatgoal. As we smoked and finished off the second glass, my head wasstarting to swim. She talked about learning everything a woman shouldknow from makeup application to fashion. She said that it should beuncomfortable to be dressed in anything but women's clothing.She sent me back in for yet another glass of wine. . “Alright, so,” I started, blushing a little. “Ummm… Masturbating is… Ummm… When a guy…” I trailed off, unable to finish. “Why don’t you just show me?” he asked, cocking his head to the side curiously. “If you want to, that is.”“Sure,” I blushed again. I played with myself a little until I was hard again, then tentatively jack off. Charlie watched, fascinated, as I picked up speed.“What’s the point of this?” he asked suddenly, and I stopped and looked up at him.“What do you mean?”“The point of…” he stopped, blushing. “Of what you’re doing.”“Oh… Well, you cum if you do it for long enough, and it feels amazing.”“Cum?”“Yeah, cum. It’s also called an orgasm.”“What happens?” I opened my mouth to answer, but he cut me off. “You can just show me, if you want to. I wanna see it for myself.” “Okay,” I said. This time, I started jerking off fast, closing my eyes and panting, until I felt the ball of tension again. With a moan, the ball of tension suddenly.
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