On a purely physical, non-sexual level, I don't necessarily enjoy the various steps that go into "being a woman". Walking in high heels are a pain compared to a pair of comfy running shoes. Makeup during a heatwave in August? Not all that fun. Yet I still eagerly do it because the mental aspect just does it for me on so many other levels. The more restrictive the clothes, the sluttier the look, the more uncomfortable the situation, the more I enjoy it. Part of that is probably because I'm so submissive by nature, it just plays into the whole shut up and take it type mentality I enjoy. A super tight corset is very much like a pair of tight handcuffs, something that is restrictive and inhibits your natural actions.
On a much deeper level though I think, and I'm doing some self psychoanalysis here, I enjoy the process of transforming from the average guy next door to a slutty whore bitch, of which the careful regime of getting dressed is a huge part. It acts as a gateway from one extreme to the other. Where as a football player might make the switch between a calm educated adult to a quarterback crushing animal by psyching him self up before a game with yelling and screaming, I make the switch by gently sliding on stockings and slipping on a bra. Each has the same effect, you leave your normal comfort zone and enter a mental place you want to be.
I don't want to sound all Buffalo Bill from Silence of the Lambs creepy, or anything, but it really does feel like a transformation when I'm fully dressed and in my proper sub space mentality. Things I wouldn't do or say in my normal vanilla life aren't held back anymore. I'm much more outgoing, open, and less nervous when I'm dressed and serving Miss H. It's such a mental escape valve to blow off negative feelings. No matter what issues I might have to deal with that are bothering me, being able to take a break from them, even if only briefly is a great way to reset me and alleviate an unimaginable amount of stress.
So I guess kinky sex and dressing in particular is kind of my coping mechanism. Probably not the healthiest way to deal with life when things get tough, but it could be worse. I could be an alcoholic, use drugs, or just be an asshole in general, instead I pull on a shiny satin pink sissy dress or lace up some thigh high boots. Doesn't seem so bad in comparison now does it? There's also other options like running (which I do) or meditation (which I've always wanted to try) to keep you sane, but they aren't quite as much fun as dressing like a hooker now are they?