I had him lie back down on the bed, look at the pictures and start jerking off again. He was embarrassed but I told him I liked what he was doing, enjoyed his being dressed as a woman and that he was passable. I told him he really should be a she and that everyone would get excited seeing her outside and not know she was a he. He said he shaves everything and wanted to go out dressed and I said we would go out together. I told him I had fantasies about what he was doing and had worn some women’s clothes before and jacked off. I asked him if he thought my girlfriend was attractive and if he would like to wear some of her clothing and jerk off. He said yes and confessed he had worn other women’s clothing; actually he has a collection at his house. We talked about one of the neighbors that he had clothes from and she is attractive. We talked about having her and got really hot. I was rubbing my cock through my shorts and decided to strip from the waist down. He watched and saw my hard. "Reggie, is there something on your mind?"I caught him off guard. "Uh, no, nuh-nuh-nothing in particular except being with you, and the movie, why?" You can tell me, Reggie. We're together again. We're a unit, okay? If there's something you want to do today, something special, don't be afraid to ask. I won't be offended. I promise." Really?" For the first time in months, I saw his shyness come back. I'd guessed right about what he wanted. "Really. So come on, tell me what's on your mind." I want, I want, I..." he stammered. Then he sighed heavily as we stopped at a traffic light. "Karen, I gave you a bit of a scare a couple of weeks ago. I'm sorry about that. I'm thinking about something we could do to show our love for each other, our commitment to each other, our---Um, Karen, do you get what I'm trying to say."I composed myself and answered him in an even tone. "Sure, Reggie. You want sex." Uh, yeah, that's it. I think we're ready to start having sex." Cool. I'm up for it."I could.
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