I'd say sure, why not? I never dressed up in my mother's clothes or had sisters at all. I started in my late 20's because I wanted to see what it was like. Preciously, I had been curious for a little while what it was like to wear women's clothes but only got the courage to try it later. I do have a fem side that this does satisfy. But there is no reason why a dude couldn't try on a dress at 50 and fall in love with it.
