This post may contain Adult content.
Adult
Only logged in members can reply and interact with the post.
Join SimilarWorlds for FREE »

I Like To Dress Like A Girl

I am a true mamma’s boy. She influenced most things in my life. She kept me tied to her apron strings and she with the help and participation of my father feminized and sissified me.

Mother encouraged me to wear her underwear as a kid and throughout my life but it was those early encouragements that shaped who I am now. Most boys are fascinated with their mother’s panties and most even try them on and experiment. My mother encouraged me to wear her underwear and I often did under my clothes.

“Come dear. see what mother bought for you” and I’d go into her bedroom. She’d close the door. My older sister and younger brother would be somewhere in the house.
She’d have me take my pants off and she’d have me put on her panties. Of course I’d get an erection and of course she’d notice and she’d tell me “be not ashamed son.”

She started with panties and she also bought me bras and stockings, dresses, blouses, and my favorite thing a full slip soft and frilly and very dainty. I wasn’t sure if when she started touching my young boy cock through her underwear but she did and as she rubbed it through the material she bore witness to my first climax. Of course she said I shouldn’t be ashamed of what we were doing and how I was feeling.

She’d pass me to my father who did to me in my butt what his father did to him. He was raised on a farm and his father played with him in the barn or the shed or out in the fields.

My father played with me in the basement or on the back yard under the portico, or in his den with the door closed. The rule in my house was when the door was closed no one was allowed to enter. No knocking or disrupting.

When I was alone with mother in the house she’d have me dressed as a girl. My cock was beyond small and she told me many times (before transitioning was fashionable) “you should have born a girl, that little thing between your legs...you won’t use that for anything...men will like and use you like you were a girl.”

She started taking me to her favorite lady’s clothing stores when I was 15. The sales ladies in those high end stores didn’t bat an eye as we’d walk in “oh Anne dear, this is my son....(sometimes I’d be dressed as a male but most times I’d be dressed as a female) please make sure you take care of him...”

Anne would take care of me for many years. Sometimes I’d just show up at the store unannounced and Anne would see to my needs. She never judged. “you are very lucky you have a wonderful mother. She’s quite special.” She looked at me smiling “and so are you.”

I lost touch with Anne over the years but I had occasion to walk into a ladies boutique in the city and find a nature sales woman not those young chippy’s that just wouldn’t understand. As Betty was fitting me in a private changing room I told her about Anne. I told her how special she was to me.

My mother knew what my father was doing with me. If she didn’t encourage it and give her blessing he would have done it anyway. But this way there was no secrets. It was a “normal” and “natural” thing to be with my mother and be with my father in the way that I was.

My father was abusing my sister. She was seven years older than I and she didn’t look at their involvement as abuse. She liked it and my father liked it. And me, I liked it and it helped prepare for my life.

And I still like it. All of it.
sissysummer · 41-45, M
i like dressing like a little girl too
very exciting to read, especially the adventures with your mother.. Was Betty encouraging? It seems she would have been?

 
Post Comment