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Are we having fun yet, or are you falling in love?
Yummy! Heavy make-up & rubber! My favorite. The fantasy would be complete if he had a very tight girdle or corset underneath... It would help his figure too.
I used to sneak into my mother's things and put on her corsets, girdles and bras. I was the only teenager on the block and did a lot of babysitting. I tried on the bras, girdles and corsets of most of the mothers in our neighborhood. At the time I was growing up firm and heavily boned foundation garments were still common and I loved the feeling of them holding and squeezing my body. I made leg braces from my Erector Set and curtain rods. I devoured any pictures I could find of braces, armor, diving suits or pilot's pressure suits. The Sears catalogue was favorite reading material with the numerous foundation garments shown in it.
I also discovered that I had strong transvestite feelings although I didn't have any idea what to call them. I loved to dress in corsets, girdles and bras and imagine myself a woman. The sight of breasts on my chest sent shivers all up and down me. I wanted to wear women's underwear and feel it hold and confine my body and to have breasts. The idea of actually becoming a woman was an impossible dream in the 40s and 50s but it didn't stop me from wishing. be a woman. My ultimate dream was to be a female polio victim and to be in an iron lung at night and wear leg and body braces during the day. At the time I had never even heard the word transvestite and thought I was the only person in the world who had ever thought such things.
I also found myself fascinated by another feeling I didn't have a name for. I liked to have my genitals trapped and inaccessible, usually under a tight panty girdle. I bought several and would wear 2 or 3 at a time to get the tightness I wanted. After a while I bought a small protective athletic cup and wore it underneath. There was not room for me to get an erection in it and the feeling was exciting for me. I was not locked in but access was a little time consuming for bathroom needs and required privacy which I also found exciting.
At about 16 I got up the nerve to go into a shop selling corsets. I told them my mother had insisted I pick one up for her as she was unable to get out. You can imagine my nervousness which was about the same as a teenage boy being asked to buy a corset for his mother. I had done my homework and had a note, supposedly from her, giving style and size. I got a heavily boned front lacing corset that fit me well. I would wear it over a panty girdle and my cup and I wore stockings as well. I loved the tightness and rigidity of the corset and the way it made my genitals even less accessible. I wasn't able to wear it as often as I desired but it was wonderful when I could. My male parts were completely invisible under it all. I was not locked in chastity but it was a start.