My 18 year oldnephew lives with me and 3 months ago I came home early from work and discovered he is a crossdresser. I has always been very feminine and is very pretty. I talked to him about it and said it was OK to dress up in the house. Soon he was fem all the time. He also wanted to be called Jenny. I soon found I was getting turned on by him. We would sit on the sofa, and he snuggle next to me. One night he was in a baby doll nightie and placed his hand on my boxerd. I started to get hard and he simply leaned over and took my cock in his mouth. I was stunned, I said Jenny this is wrong. But he started crying and looked at me, " I want to Uncle Tom, I have never been with anyone. I love you, I want to be your girl." I shouldn't have but I pulled him to me and we started to kiss. A few minutes later he was on my cock. I only lasted a few minutes I was so turned on. I came in Jenny's mouth swallowing all me cum. Jenny looked at tears in his eyes, and asked " was it as good a with a real girl?" I pulled her to me and said "you are a real girl to me". And kissed her long and hard. Since that night we have been lovers and in love. I gently took her anal virginity the next night. I now see Jenny as truly female. She has a lot of sexy clothes, and we go out as a couple. We are moving as the family has disowned us. My I have money and we love each other. Last night Jenny said she wants to get boobs like a real girl. I said what every you want my love, but you already a woman to me. I love her so much, she is a prefect woman as she is. We also want to get married.

My 18 year oldnephew lives with me and 3 months ago I came home early from work and discovered he is a crossdresser. I has always been very feminine and is very pretty. I talked to him about it and said it was OK to dress up in the house. Soon he was fem all the time. He also wanted to be called Jenny. I soon found I was getting turned on by him. We would sit on the sofa, and he snuggle next to me. One night he was in a baby doll nightie and placed his hand on my boxerd. I started to get hard and he simply leaned over and took my cock in his mouth. I was stunned, I said Jenny this is wrong. But he started crying and looked at me, " I want to Uncle Tom, I have never been with anyone. I love you, I want to be your girl." I shouldn't have but I pulled him to me and we started to kiss. A few minutes later he was on my cock. I only lasted a few minutes I was so turned on. I came in Jenny's mouth swallowing all me cum. Jenny looked at tears in his eyes, and asked " was it as good a with a real girl?" I pulled her to me and said "you are a real girl to me". And kissed her long and hard. Since that night we have been lovers and in love. I gently took her anal virginity the next night. I now see Jenny as truly female. She has a lot of sexy clothes, and we go out as a couple. We are moving as the family has disowned us. My I have money and we love each other. Last night Jenny said she wants to get boobs like a real girl. I said what every you want my love, but you already a woman to me. I love her so much, she is a prefect woman as she is. We also want to get married.
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When I was in high school my friend and I would spend the night at each others house off and on but just about once a month. One night we were laying in bed after lights out as my dad would announce to us. We were whispering and she asked me if I had ever had an orgasm, I was a little surprised at her question but told her I have many times. I told her that I have only used my fingers or rubbed myself on a pillow. She was curious about that one and asked me how I did it with a pillow. I got up and retrieved one of the pillows off my chair, it was square with little tassels on the corners, they had knots in them which were great to rub on. I positioned myself on my bed with the pillow corner under me and began moving my hips around showing her how I did it. She looked on and asked me if she could try it, she got into position and started gyrating her hips and rocking back and forth and I thought to myself wow I wonder if I look that hot when I do that. We laid back down and the next thing I felt was her hand running across my nipple then tracing around my breast. I just went with it and ran my fingers over her breasts and nipples also, after a few minutes she leaned in and kissed me. She was gentle at first then we got pretty passionate and I was getting really turned on. We stopped for a second and I asked her if she wanted to take off our pajamas. She nodded in approval and then it was really hot feeling her body on mine as we kissed deeply. I made the first move down her body kissing licking her breasts and nipples, when I reached her pubic hair her scent was intoxicating and I could not wait to taste her. My first lick of her was so sweet that I just sank my tongue inside her as deep as I could reach. We made love until we both had a few orgasms then put our pajamas back on and went to sleep, we made love often.

When I was in high school my friend and I would spend the night at each others house off and on but ...