When I was around eight, my sister, who is five years older than me had a pair of knee high boots. This was back during the 70’s. I would sneak into her closet and snatch her boots. I’d take them to my room and put them on under my sheets.
This was not the beginning of my crossdressing; it actually started at our aunt and uncle’s home during holidays. I would go off to “the bathroom,” but I really went into my aunt’s closet to find her crinkle vinyl knee-high, pull-up go-go boots. I’d quickly take them into the bathroom. If someone would knock on the door, the boots would end up in the shower, and I would return them later when I could sneak them back to her closet.
Boots were, and still are, my crossdressing mainstay. Now that I’m in my 50’s, I have a collection of skirts, sweaters, bras, panties, and boots. When I was in my 30’s, I had over 50 pairs of boots. I have a female girlfriend who even shops for items for me. I get called Madame all the time. Sometimes, this upsets me as I have no intent to be fully female, but I can pass just fine when dressed as a woman.
When I am dressed I am a WOMAN and act accordingly, I use the lady’s room. I use my fem voice, which my voice is fairly high so that I need to lower it for fem outings sometimes. I have used makeup, false eyelashes, and false nails. When I lived alone, I would dress up on Friday night as soon as I got home from work and stay dressed till church time on Sunday morning.
When I was younger, we had sisters in the neighborhood that lived together across the street from us. We had a key to take care of their house while they were away. I would go over at first to try on one of the sister’s boots. Then I would wear their pantyhose and then their bra. Eventually, I would be fully dressed in her clothes. I would lie on her bed in her outfit and daydream. I would change back to my clothes and head home across the street.
I am now 56, living with my older brother in our parent’s house. They have both passed. I have small collection of clothes and a couple pairs of low heel boots. When I lived on my own, I would walk home from work at night and there was an “Adult” store on the way. I saw a pair of Leather Thigh High Stiletto Pleaser Boots and paid $150 for them. I went home and put them right on. I would wear them and drive to a drive-thru to get dinner. I still have them.