01-17-2013, 11:00 AM
I was a typical 60+ year old guy who had been going to BDSM mistresses for about 20 years to get a dose of teasing, torment and cruelty from time to time. I always enjoyed these sessions, but nothing like the day a I went back to a Pro Mistress for a session and jokingly, she asked me if I had ever dressed as a woman. I told her not since I was a teen and tried on my mom's bra. She then "hooked me up" by my leather collar to an overhead winch and began to put me into a bra (with forms), panties, garter belt, nylons. Then she attached my leather cuffs to each other behind my back and had me sit at her makeup table, facing away form the mirror, while she applied makeup, lipstick, eyeshadow, and several wigs until she found one that she liked. Only then was I permitted to see what I looked like and WOW! I couldn't believe my eyes!
They she applied stick-on nails and painted them bright red to match my lipstick, dressed me in a pencil skirt and bulky sweater and about 1" heels. After having me practice my walk and having me read to her in a falsetto voice, she said, "common, girlfriend, we're going out!" So we did, going to a drag bar inhabited by all sorts of CD'ers and Trannys as well.
This was a really profound experience for me and I have been hooked on crossdressing ever since.
They she applied stick-on nails and painted them bright red to match my lipstick, dressed me in a pencil skirt and bulky sweater and about 1" heels. After having me practice my walk and having me read to her in a falsetto voice, she said, "common, girlfriend, we're going out!" So we did, going to a drag bar inhabited by all sorts of CD'ers and Trannys as well.
This was a really profound experience for me and I have been hooked on crossdressing ever since.