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my first time ( or at least an attempt) cross dressing would have been the time I decided to try to wear my mom's boots. Needless to say it did not work out as my feet are several sizes bigger.
My first dress however, was a Snow White dress I had bought from a Spirit Halloween store. It was, a little bit hard to handle as the skirt went past my ankles and I had to lift it if I wanted to move.
No experience with heels, again, no female shoe in the house that would fit.
Not much with makeup either, only little bits here and there.
I don't exactly remember my first time but I remember that I was always grabbing garments that belong to my mother and taking them to bed with me. I pretended that they were mine I must to have been doing it since I was very little because my mother never said anything she will just take them away. I used to put on her high hills and grab a purse too I was probably 8 then. I think I try my first bra ( actually my sisters) when I was 12 and 16 when I fully dress for the firs time.
I can remember as a kid putting on my mom's high heels. But... I've never really been sure if that "counted" or not, because I did the same thing with my dad's work boots. In both cases, of course, they were far too big.
In college, I would occasionally wear my wife's panties to class or dinner. This was purely sexual, though. Both of us found it to be a huge turn-on. For whatever reasons, that practice slowly drifted away as we went through school, got married, etc. Spring of 2015 (I think; it may have even been 2014), the urge hit me again. No idea why. I got the courage to mention it to my wife. She pulled two pair of panties out of her drawer and gave them to me. I wore them to work, and loved the feeling. It was still sexual for me, but there was something else this time too. I went a few weeks with wearing a pair of hers once or twice a week. Then I went and bought three pair of my own. By Christmas of that year, I was wearing panties almost every day, and had also bought some stockings and pantyhose. By that time, it was just what I wore and no longer really something that was sexual.
This past summer (2016), the urge to wear more hit me. I don't recall ever really having that urge before, but maybe I did and just buried it. But in August, I made a pretty big purchase off of Amazon, after researching how to convert men's sizes to women's. I bought a red dress, a denim skirt, a blue blouse, a bra, and two pair of shoes. It was... relaxing, I guess, is the best word I can find right now. I bought a few more things, including hitting eBay. Things really took off for me after I found CDH. That was when I decided to make birdseed breast forms, get a wig, get my own jewelry (I was wearing hers), and so on.
And now, here I am. 🙂
