A crossdresser Son and his Dad


My story begins when I was younger. My two older Sisters would play dress up with me. Dressing me up in their clothes. As we grew older the games stopped but I would still ask them to dress me. They told our Mother what I asked them. Her response was that if I still wanted to play dress up I should be allowed to. So the games continued. As I grew into my teens it was not uncommon for me to come home from school get cleaned up and go to my sisters’ room and get dressed up. I was not at all uncomfortable running around the house wearing panties, stockings, and a nightgown. Even in front of my Brother and Father. One evening when I was around sixteen my Mother called me into her room and asked me to sit down. She wanted to ask me if I had ever thought about sleeping with a man while wearing the girl’s things. I told her that I had wondered about it. Her next statement really floored me. She went into an explanation that it was tradition in our family that Dad would sleep with the girls when they turned sixteen. She said that she and dad had been talking and wondered if I might to be treated like one of the girls since I liked to dress like one.

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   I was shocked but I was also curious. She said that dad would stop anytime I wanted him to and I did not have to do anything I did not want to. I thought about for a minute then asked Mom when. She said that we could do this tonight and that she would be there to show me what to do. I said okay. Mom told me to go shave and take a good shower. When I was finished to meet her and the girls in my After I had cleaned up really good I went to my room. Mom and my Sisters were all three sitting on my bed. They had several items of lingerie that I had always liked. They dressed me in a satiny pair of panties with matching garter belt and stockings, then a really nice silky nightgown that just covered the top of the stockings. Mom then told me to sit down for a minute. For the first time ever they applied makeup to my face. This was a new experience but it did make me feel really sexy. Mom said for me to wait in my room with my Sisters until she came to get me. It was just a minute before she did.

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   She took me by the hand and led me to her and Dad’s room. Several candles placed around the room lighted the room. Dad was lying on the bed patiently waiting for us. Mom gently led me to the bed and said for me to lie next to him. She removed her housecoat to reveal she was dressed in an outfit just like mine. She climbed into the bed and started kiss Dad. They broke the kiss and Dad turned towards me and gently kissed me on the lips. I was really nervous but excited at the same time. After we kissed for a minute or so Mom said that the first thing I needed to do was to learn how to suck his dick. She opened her mouth and slid it into her mouth. She began a rhythmic bobbing of her head and it appeared that dad was enjoying it. She let it slide out of her mouth and told me to “come here” I slid over to her and she said, “Okay, just open your mouth and put it in. When you have as much in your mouth as you can comfortably get close your lips around it. Watch your teeth, and slide your mouth up and down the length while sucking it. ” So that is what I did.


   I opened my mouth and took it in. Closed my lips around it and slip my mouth up and down the length while sucking. It felt so warm and hard in my mouth. I heard Dad start to breath really fast. He said, “ I’m going to come soon”. I was enjoying it so much that I wanted him to come in my mouth. He tensed up as his dick felt like it expanded as he came in my mouth. I don’t know how but I managed to get it all without chocking. I liked the way it tasted. It was both salty and twangy at the same time. Mom said that I could spit it out if I wanted but I swallowed it After resting for a few minutes Dad said that he was ready to continue. Mom said for me to take off my panties and get comfortable on my stomach. I did as she instructed and got really comfortable in the middle of the bed. I felt Dad get up close behind me and start kissing the back of my neck. As he did he gently rubbed the cheeks of my ass.

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   Then he slid his finger in against my hole. He gently rubbed me until suddenly his finger slid inside. I tensed a little but I really liked the way it felt. I relaxed and he continued to slide his finger in and out of me. Then he slid a second finger in. He continued to slide his fingers in and out of me until he had a third finger in me. He slowly removed all three fingers and said to Mom “I think he’s ready. ” Mom then spread my cheeks she said “this may be cold at first. I am putting some lubricating jelly so that everything will go easier. ” She applied some of the jelly directly to my hole and massaged it in. Then she slid away from me and Dad came up behind me He kissed the back of my neck again and suddenly I felt the head of his dick pressed against my hole. He applied a gentle but steady pressure as he slid into me. Before I knew it I had his entire dick inside of me. He began to gently slide in and out of me. Dad started fucking me faster and faster until I felt his dick expand like it did in my mouth.

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   He went stiff and I felt the warmth as he came inside of me. The combined feeling of the stockings, nightgown, the fullness of having his dick in me, the warmth of his cum were just to much and I shot my own cum all over the bed and my lingerie. It was wonderful. Dad let his cock slip out of me and we both just lay there basking in the afterglow of the experience. Mom told me later that I would soon be able to be with the girls sexually if I wanted. I did but that is another story as is the experiences with my Brother.



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