Like most boys, I started cross-dressing by wearing my mom’s panties and nylon stockings. Doing so was both erotic and enjoyable, but being a pre-puberty 8 year old child, I was not sure of the reasons why. Eventually, with puberty, came the desire to wear my quintessential items of womanhood: bras and lipstick! Although strongly drawn to these two items, I was overtaken by fear. Fear that I may reach a point of no return and become a sissy (i.e. a boy dressing in girl’s clothes without any sexual reference applied). It was an embarrassment, what would my family and friends now think of me? Thus, my “secret” was born and it would be kept for another 6 years, during which, I resolutely expanded into mom’s remaining trappings: dresses, skirts, blouses, heels, jewelry, additional lingerie and makeup. I still felt guilty about my “secret” (and the arousal it caused) but I enjoyed even more my womanly transformation and seeing her reflection in the mirror. However, an unexpected day of reckoning was fast approaching.
I was 15 years old when one afternoon my dad left to watch a bowling tournament my mom was participating in. Great! Several hours alone, more than enough time to watch television and relax while dressed as a woman. However, I forgot to lock the door and as I headed to the bathroom to put on my makeup, my dad unexpectedly returned home for a forgotten item. He was gone long enough for me to put on my mom’s bra, panties, garter belt, nylons and heels. When he came in his draw dropped. I ran to the bathroom in my heels and locked its door. I was caught! Eventually, my dad came to the door and asked me to come out. I said “no, you saw me, I can’t come out!” About 15 minutes later I came out with only a towel on. We talked, and he said “I’ll need to tell your mom about this when she comes home”. I pleaded with him not to, but to no avail. I was told to get dressed and go with him to see my mom’s tournament. No more being left alone to cross-dress. After what seemed to be forever, we arrived home. When dad told mom, the s—t hit the fan as she told me to never get into her things again or else…! Next day we talked about it and she asked if I liked dressing up? I said “no, and I wouldn’t do it again”. Sadly, I wish I could have said “yes” and maybe been able to dress up after school and be my parent’s pretend daughter helping with meals, washing dishes and cleaning the house.
After several months, I began to again dress secretly in mom’s things. I’m sure she noticed that her bureau draws and closet items were not quite as she left them, but she never mentioned it. I would continue to dream of being a sometimes female for another ten years. Then following graduate school, I got my own place and with my initial paycheck, I splurged and purchased the latest female fashions thereby creating my own hoard of feminine garments, heels, makeup, and a first wig. It was thrilling and surreal; I could dress as a woman on demand! Something I had dreamed about since childhood. Thus, after work, I dressed up and became the lady of the house. On occasion, I would wait for dark to journey out for either a walk or a drive. These nightly excursions were both terrifying and exhilarating as I sometimes got cat calls or whistles, but that’s another story!
Thanks for taking the time to read my article. Now please take a little extra time to either leave a response to my article or provide an answer to one or more questions I’ve posed to you below:
- Were you ever caught cross dressing as a child or young man by one of your parents and if you did, what happened?
- When you first started cross dressing as a young boy, was there a sexual arousal associated with your cross dressing?
- Was there guilt and shame associated with your early years of cross dressing?
Thanks so very much girls and I look so forward to reading your responses!