From the very first time I picked up my mother’s pantyhose and ran my hand over the silky smoothness I was hooked. I found a discarded pair and just had to try them on – the feeling was electric. I ran my hands up and down my nylon encased legs and it was heavenly. The only other thought I had was that it was somehow a bad thing to do. Here I was a boy wearing pantyhose and loving it. I was so ashamed that I had tried them on. I knew I had crossed some kind of normal behavior. I felt that I was a terrible person and that there had to be something wrong with me. I was ashamed and excited at the same time. I took them off and hid them away, knowing I would like to wear them again.

I sometimes came home from school and before mother would come home from work I would go through her stocking drawer and run my hands through her things . This was at a time before most women stopped wearing dresses and hose. The sound of a woman wearing stockings while walking, with the nylon rubbing together on their legs was exciting and made me want to have that experience. This is where it all began – my journey into that forbidden world, the place where boys were not allowed to go.

We were supposed to admire girls wearing stockings not want to wear them. The secret had to be kept because if anyone knew I would be most certainly be punished, ridiculed and embarrassed. How could I deal with that? My friends would never associate with me, it would be as if I had some terrible disease. This desire had to remain my secret.

Whether my mother knew that I was playing with her things or not she never questioned me. Looking back I do not know what I would have done. The next piece of female attire I tried on was high heels. I had looked at them while I was putting on my pantyhose, usually the discarded ones with runs in them, and wondered what it would be like to wear them. It wasn’t long before I gave in to my thoughts and slid my nylon encased feet into a pair. I had watched women walk in them and wondered what it would be like and when I took a few steps in them that first time feelings overwhelmed my senses. I knew I was hooked AGAIN . My feet were almost the same size as my mother’s so most of her shoes fit. They were slightly too big but I did not care. Each time I wore them I would carefully put them back and place them exactly as I found them.

This is how my secret began and I will write more about it in my next installment.




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I was a closet dresser for years, afraid that someone would find out about my secret. I hid away dressing by myself and dreaming of the day I could go out into the world as who I wanted to be. After many cycles of buying fem clothes and then throwing them away I finally met a few people who helped me with my dressing and introduced me to the transgender community.

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Sarah Mack
5 years ago

I like most of you on here it started at a very young age wearing my mother’s clothes my mother was a bit of a perfectionist and I learned real quick how to put stuff back exactly the way I found it I don’t think she ever knew but the thrill was always there. My mother and father I don’t believe ever knew of my dressing if my dad hadn’t found out I probably would still have marks on my backside I am much older now my kids have grown and moved out my wife knows of my dressing but… Read more »

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