It’s interesting, I think, how my motivation to crossdress has evolved over the years. When I first started, as a young boy, I was curious about what it would feel like to have breasts and to wear a bra. I remember when I first tried on one of my mother’s bras, it was a huge turn-on. As my sister got older I would sneak into her room and try on her clothes, sometimes getting fully dressed up in a dress or skirt with a blouse. I felt beautiful, the way that I felt about women that I’d see in magazines and catalogs. No matter what I was wearing, I would always find myself extremely turned on, get off, and then be ashamed of what I’d done.
In my teens I didn’t dress as often. I was in college and living in the dorms and even a fraternity house made it impossible.
When I graduated and started living on my own I started buying lingerie and clothes for myself. I had everything a girl could dream of but kept it all a secret. Unfortunately, a girl I was dating found my stash one day and I was forced to purge everything. We broke up shortly after and I was forced to start over, still keeping things a secret. I continued to date and eventually got married. My wife knew about Brynn but didn't approve, so I had to keep her hidden. We divorced after 4 years for other reasons and things picked up again. By this time I had gone beyond just clothes. I had wigs, shoes, makeup, and even jewelry. I started dating again and was very upfront about crossdressing. Granted I told girls about it via text for fear of rejection again. Eventually a girl I was dating was OK with it, even curious. She asked me to model for her, so I did, and she loved it. We've been married for 6 years now and Brynn is a regular part of our lives (when the kids aren't around). The only conditions are that a) I have to model anything new that I buy and b) I have to be locked in chastity when I'm Brynn. I don't know if that's too forward for this but it's a part of who I am and I've come to love the control my wife puts on me. We've recently begun to explore pegging and feminization/sissification. I'll let y'all know how that goes, but so far,so good!