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This all began in a Puerto Rican neighborhood in the early 70s. I was the only boy in the apartment building. I have 2 sisters one is 5yrs older than me and the other one is 1yr apart. My mom was feeling sorry for ne cause I had nobody to talk or play with. I usually played with my toys or watched PBS (Sesame Street, etc.) My mom came up with the idea of dressing me as a little girl. There was 5 other apartments and all were little girls my.age. i couldn't play.with them at the time cause boys aren't supposed to play with girls. My mom one day decided that she's going to introduce me as Jilliana aka Jill. My mom dressed me in my sisters clothes. I didn't mind cause I didn't really know how a boy really acts cause I only had 2 sisters and a bunch of girl cousins. I started to enjoy the dress up cause my sister's treated me different. They will help my mom dress me if she was busy. My Dad found out and was furious and told my Mom that she better not ever do that again. My mom still did it but wouldn't take me out dressed no more. My mom will invite the neighbors to the house so the girls can play with me. My Dad eventually found out again and that was it, no more dressing up.
I decided to take matters on my own and started dressing on my own. My Mom had gotten a job and left my oldest sister take care of us. My older sister will still dress me but would always say "don't say anything" I never said a word....
I was in the washroom one day and my Mom just washed clothes and her lingerie and nylons hanging in the washroom. I locked the door and started dressing and that became my routine. My Dad cought me once cause I forgot to lock the door. My Dad was so furious and said "you're a BOY"and spanked me. He told my Mom and blamed her for everything.
to be continued...
- 9 Nov, 2026
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