This is a great topic. I am 24 right now and started a young age, most likely around when I first hit middle school. I started wearing my mother's panties and bras. I remember the softness and tightness of her satin panties and bra. Especially, a front clasp bra. I then started putting on her skirts and blouses while my parents were away. I stopped dressing in high school for a years. The urge to dress came during the senior year of my undergrad. I had my freedom because I just bought a truck and was renting an apartment with three other guys. I started up again with just lingerie, mostly teddies, bustiers, thigh highs, and thongs. Basicly it was just a sensual feeling that drew back in again. I was hiding this from my fiancee until I finally came out a couple months before our wedding. I am so lucky to have an understanding wife. When I started my first year of grad school, I slowly moved to wearing more conservative lingerie under my clothes. This week in fact, I went out for the first time wearing a pair of my wife's jeans (we are a similar size), leather boots, a nice short t shirt, and some casual makeup on to a nearby mall.
basicly, for me the biggest challenge is balancing my wife's feelings towards my dressing with my growth in this area. I am taking it slowly for the both of us. It is also a struggle to afford clothes on a grad student stipend.
