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I started cross dressing at 5 or 6, I was always around when Mom put on her nylons and makeup so I learned this quickly. Some time passed then one day my Aunt and Uncle came over to go to a party with my parents. My Aunt had on a short black cocktail dress that sowed off a lot of cleavage and her beautiful legs in her high heels. When I saw her I said to myself that I wanted to look that gorgeous some day.
From that day on I would dress and put in Moms clothes and makeup when ever no one was home. Mom came home one day and caught me, she just told me to go get cleaned up and not to let my Dad catch me dressed like that. Dad was real strict and used the belt on me if I was bad.
Around this time my friend and I met a boy that was a few years older than us. I won’t go into this here.
Mom never told my Dad abut my dressing and we moved to California the following summer. Mom went to work ever day and Dad worked a lot of OT. My sisters were gone a lot playing at their friends. So I spent a lot of time dressing up almost ever day.
One day I was all dolled up real sexy and had on full makeup and high heels.. Some one started ringing the front door bell and didn’t stop. I figured is had to be the paper boy coming by to collect as he always did that a lot. I looked outside several times and didn’t see a car or any one and the door bell kept ringing. So I opened the door figuring I’d give this paper boy a thrill. There stood my Uncle looking at me. Nothing was said for a few minutes then he call my name. I was scared shitless that he would tell my Dad I looked like some bimbo. He finally came in and after me begging him not to tell my Dad he made ne go and clean the makeup off and get dressed properly. Thanks god he never did.
I only dressed a few times after that and graduated High School. I joined the Navy for 4 years. During my time in the Navy, I have a few incidents with gays civilians. But married my first wife just before getting out.
We had a great marriage for about a year and on day she said she was home sick and I ut her on a plain and she went home. Six months passed and I had no heard from her. I had no phone number to call her but her Mother called me at work and asked if she could come back. I sent plane fair out the next day. But had no idea why she never called me in the all that time.
I set us up in a new apartment and a few weeks later I came home from work and she had my rifle barrel in her mouth and said she wanted to kill herself. I had no idea why. (I suspect she had an abortion while she was gone) To make a long story short she was put in a mental hospital and we separated.
One of the guys at work told me about this club that he and his brothers owned. It was noise in the shop that day but he invited me to the club on Friday night. The club was a Female Impersonators club. Needless to say my cross dressing came to life again. Although my coworker had no idea I liked to dress. I spent a lot of nights at the club and met Rob there one weekend. We became friendly and he asked me over to his house for a weekend. He told me to meet him at has place on Friday night after work and we could go out for dinner and to the club after that.
When I got to his place he told me I could use the shower. and showed me where to go. When I came out of the shower, I saw a beautiful yellow dress and all the trimmings laying on the bed. He came in the bedroom and asked me if I would like to put the dress on. He said we’re about the same size and It should fit you. He told me I could use the makeup in the bathroom drawer and get dressed, I was so excited I didn’t know what to do, It took me a long time but I finally got all dolled up. He came into the room shortly after I had finished. He had on a gorgeous red mini dress heel and a wig It was almost a perfect match to the yellow one that I had on. He went to the closet and pulled out a blond wig and helped me put it on. I was so nervous I almost passed out. He grabbed me just then and planted a kiss on me. Needless to say we spent the evening together and never did go to the club.
Rob (Roberta) and I became good friends. I spent a lot of weekends with him. He had a huge wardrobe of women’s clothes and all kinds of lingerie. I found out later that he was an Impersonator. Roberta and I spent a lot of time dressing up. He showed me what clothes to wear together and how to do my makeup. I shared his bed quite a few times.
One week end I got to Roberta’s and there was another guy there. He and Rob ended up in bed an I saw then having anal sex. Rob wanted me to join them but I declined. I left the next morning and never went back
I met my second wife got married and hafe a family after that. I still dressed up when ever I could. Our marriage fell apart after 7 years. All my boys are grown now.
I moved to San Jose and has a new job. I dressed at home almost all the time when I was not dating. I wanted to transition at the time but had fears about my family accepting me as a female. I looked at that possibility for a few years. I had the money but didn’t have the nerve to go through with it. There were even a few men that had transitioned where I worked. One of them came down with Aids and died that scared me badly.
I met a woman who was a great cook. After 5 years if being with her we finally married. She had now idea I liked to dress. But one Halloween she help me dress and I went out as a woman I public for the first time in my live. My wife has had nothing but one medical problem after another since then. I only get to use my stash when she visits her daughters.
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Wow that is a crazy life story Jenna. Really thanks so much for pouring out your heart and I hoped it helped you get that out.
In this day and age I think it is important to remind the young adult of the dangers of AIDS and how the depiction of sex by the porn industry (like any film industry) is still not real life.
I do hope you are able to sort things out and suggest some therapy to help you deal with the harder spots. I’m not a huge therapist fan but just having someone to talk freely with and that won’t judge you is beneficial.
Hugs – Terrisa
Wow Jenna! I can relate to a lot of your story. I even got a little bit teary eyed remembering my life and the parts that touched. Only a few parts similar but it brought back great memories. I was in the Navy (29+ years). Enjoyed company with a friend who shared his dresses with me but when he started talking bout AIDS. I got scared and ran. Anyway thank you for this
I’m not sure who I getting this reply but there are 5 persons commenting on my store so I hope this goes to all of you.
Thank You all for the comments on my story. I’m glad it touched all of you. I put this out to let all the young members had life can through you some curves. And the need to protect yourself from Aids.
I liked reading your story. Thanks for sharing.
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