I hear that question all the time.
I started playing with make-up much earlier on, although it initially was just a way to cover a blemish, or darken my blond eyelashes. I colored my hair and glossed my lips all through high school, and never felt I shouldn't have. I really always just thought, "Why do girls get to have all the fun? Who made up that rule?" As a society, we only think lip color is feminine, because someone before us decided it was and told us so. We also call a tree a tree, because that's what some one else taught us. The majority of our behavior is learned, and we often refuse to challenge those norms. Does strapping on a YSL pump make me less of a man? Absolutely not. In my opinion, it takes some serious courage and confidence to step out the house as a 33 year old man in booty shorts and a open-toe sandal with a 5 inch heel. I know that same day I was lifting weights with my callused hands and dripping sweat in the gym, and I can be both people, and everything in between if I want to.
It's a hard thing not fitting into a box though. I do remember my Mom asking once or twice if I wanted to "Be a drag queen?" The answer was always "No," but that was the only thing she knew of when it came to men putting on make-up.
I was the trainer who would probably show up in booty shorts, leg warmers, and definitely some mascara, and still sweat my butt off and kick yours along the way. It became my brand. Sort of a glamorous showgirl of fitness. Although it wasn't a show, it was simply who I was.
Dating often presented a whole new slough of conflicts. I remember hiding the heels if a date was coming over. I used to try and even butch up my apartment for fear of someone else not understanding that for me, high heels were just a small part of me. I wouldn't give my whole name, for fear of them googling and finding photos I would then have to explain. Now, in my 30's, I keep a pair of heels on display in the living room. There is a 5 foot tall portrait of me in knee high stilettos boots next to the television. While that glamazon may not be out all the time, if you're not strong enough to handle it, then we're probably not a match. So for that reason, I now keep everything front and center. If you have questions, I will gladly answer them, but the one thing I refuse to do is be ashamed for liking a little something sparkly just because you think it's too feminine.
I will never forget being told "Men are gay, because they like men, so stop "dressing up." Silly me, I always thought men were men because of their character. Men were made by their actions. Men protected and took care of their loved ones. Real men fight for causes they believe in, and work to make the world a better place. Masculinity was not something simply translated by a beard and beer drinking. I may have on two sets of false eyelashes from time to time, but I will still open the door and offer to carry your bag along the way.