My first dressing up

I have held this story in my head for ever. I have wanted to tell it but too afraid to let it out. This I think is a good place to start. When I was young I began my journey to sexual adulthood.  At night I would rub myself feeling this urge I had never felt before. I was rubbing myself nightly.

Enter my mom. As you well know when you rub yourself you release this gooey mess when you cum. I didn’t know what it was but it felt good. Now at first I didn’t know why this was happening. I did know when I would see my sisters in their sleep clothes I would get urges. I thought that felt good so I would rub myself thinking of my sisters. One day I was walking past my mom’s room and I saw the door was open slightly and I saw my mom completely naked on the bed. I quickly ran by but I couldn’t get that visual out of my head. 

That night I rubbed myself and came big time. I knew it wasn’t good but oh my I felt good. So I thought I would like to see her naked some more. I would watch her go into her room and usually have the door open. I finally saw her again but I didn’t run away. I stared at her large breasts and her hairy vagina area. 

That seemed to excite me. She finally caught me peeking at her and she smiled. She got up and walked to the door. She says do you like what you see my little boy. I hung my head down and shook it yes. She says I have known for a while when I clean your sheets you are leaving stains on them. I said I was sorry. 

She said also she had noticed those same stains on her panties and on your sisters nighties. Have you been rubbing yourself on these too. I answered yes mom. She asked me if I tried them on and I said yes. I told her they felt so good on me.  She said well maybe you would  like to be like your sisters. I said yes and smiled. 

She than said come on in to my room and see how you look in them. She had laid out some sexy underwear on the bed. She says go ahead try them on. I got excited and tried them on. The panties were silk the bra lacy. She say oh my you do look wonderful in those. She says now show me what you do when you are in you room alone. I lie done on the bed and I reach my hand down to my penis. I start playing with it. 

She smiles and lays next to me. She says how does that feel. I say I like it a lot. I see her fingering her pussy and telling me that she wants me to go ahead and cum. I am so excited I can’t stop. I am watching her and rubbing my self and I explode in the panties. She moans loudly and she cums. She tells me to leave her room but she says I have plans for you. Days later there are some packages on my bed. I open them and there are panties and bras and night gowns and even a dress. There is a note attached. These are yours my sweet boy. They are just a secret for me and you to know. Enjoy.

 I have loved wearing girls clothes for near 50 years. I have tried to live a normal man’s life. I have been married several times but I have never gotten over wanting to be a girl. I have wondered what it would be like being a girl. I have over the past several years bought my own clothes that I keep hidden. With the start of the internet I have found their are people like me every where. I have connected in chat rooms and on phones with many ladies like me. 

I even have found there are men that like girls like me. I started meeting them on line and now I find myself wanting men only. My first experience was with E whom I wrote about recently. I didn’t dress up for him. I wanted to meet real men who liked CD’s and Trans girls. I put a profile out on an adult friend web site. Me all dressed up and telling these men what I liked. I have had several relationships with truckers coaches professional men. 

I have finally found myself for the first time. My only wish I had done this when I was much younger. I might have transitioned myself into a real girl. I thank my mom for not stopping me from these urges. I had to get this out there even if no one likes it.