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Cross dressing sissy phone sex training, if you are in need of sissy training, I am the girl for you. I have been turning Debbie into the girl she has longed to be. She is going out on her first date tonight as a couple, with her bf. They have sex together. They suck each other off and kiss. They go on long walks and Debbie has been dressing up to please him. Debbie has been calling me regularly to learn how to become feminine and today she confessed that she wished she could dress as a girl all the time. She has sent me some photos and I must say, she has come up to the plate quickly, I can hardly see any masculine traits. She has a blonde wig, and was wearing such a beautiful skirt, sparkly pink top and pink boots. Full makeup. I am getting ahead of all that has happened.
I am going to backtrack and show you the progress Debbie has made. She emails me with questions and I answer them, she either does whatever I suggest or has her bf’s sister go and buy her things..
Her boyfriend started out by buying Debbie a dress, and she told me that he liked to have a guy wear women’s clothes. She was to be wearing the dress, when he came over that night. Next she told me, “He wants to take a walk down the road after it turns real dark. I don’t know about that. Scary. I am afraid of being seen. I did like the idea of maybe around 2 am. I did find out I like the sound high heels make on the floor or cement. I walked into my garage with them on. Very distinctive sound.” I think it is great, that her bf wants to have real relationship with Debbie, don’t you?
A few days later they had another day planned, Debbie said, “I am all dressed up. I have my floral print dress, slip, bra, panties, garter belt, nylons and 4 inches heels on. He should be here any minute. I put the wig on and the makeup. Oh, yes I have perfume on for the first time. I started getting ready at 6 pm. He asked me to shave my body (chest) hair and I shaved the legs again. I feel so feminine. I think I will walk down the street with him a lot later. I can’t wait until he gets here. I am going to greet him at the door and then give him a bj immediately. I can’t believe I enjoy this. A week ago it sort of repulsed me, getting dressed up and going to be fucked like a woman.”
After her date Debbie wrote me: ”
Dear Jennifer, It was wonderful. So much happened last night. I greeted him and gave him a bj and deep throated him (with his help) and he came in my throat. (We agreed he would hold my head and he did and I took it all). Afterwards, after he undressed me, I even fucked him in the face and put my cock all the way in and came down his throat. Then, we went to bed and he came inside me while I was on my back and then he did me doggy style ( I prefer on my back). He helped me put the dress and slip back on and we went for a short walk and I sucked him a little by some trees but not all the way to climax (too much nearby traffic). He also brought over 2 purses for me. A small one to keep the basics like lipstick, mascara, liner etc.. The 2nd one he called a sleepover bag for me to put lingerie and everything to spend the night at his place. I am glad he did not spend a lot, he picked the items up at a Goodwill store and a Salvation Army store. He wants to pick me up at my house and go to his house tonight while I am dressed up and I told him it would have to be dark outside. I mentioned we need to get some fake breasts instead of socks. I tried plucking my eyebrows a little, but OUCH. That hurts.
