Crossdressing may be more associated with straight men than gay ones.  I'm not sure if that's true, nor am I sure why it might be, but maybe it's because crossdressing necessarily revolves around women and notions of womanhood, and straights think about the ladies more than gays do.

For me, crossdressing appeals to my soft, submissive, feminine side.  As a gay bottom, I like the idea of serving as a female for an aggressive man.  As a man who has been in a long term relationship with a dominant woman, I enjoy the humiliation angle as well.  I posted photos of myself in ladies' attire on this site in the shameful hope that women and straight men might see them and laugh.  I didn't really think of those pics as something that other gay men would find particularly attractive, though I for one like to see photos of men in drag, especially if they're actually pretty.

I haven't indulged in crossdressing as completely and obsessively as many guys.  In fact, I own only a few items, though I continue to add to my collection.  These are my favorite items from a lady's wardrobe:

THIGH-HIGHS -- Nylons are lovely.  I currently have thigh-highs in white and in black.  Nothing makes me feel more feminine than stockings.  I shaved my legs only once, years ago.  It did make my legs look nicer in hose, but I hated the clamminess of my legs in bed, not to mention the hassle of shaving.  Fortunately my legs aren't too hairy, and sometimes I do shave the upper parts of my thighs for a prettier look. 

PANTIES -- These are fun, and the silkier, lacier and girlier the better.  It's a little frustrating that even my penis isn't quite small enough to fit in a lot of the panties out there, and I've considered investing in some "manties" that would fit better.  Sometimes, if the style of the panties is right, I wear them backwards to provide more support.  I even justify it in my mind by reminding myself that the narrow side of panties is designed to cover the pussy, and my pussy happens to be in back! 

MINISKIRTS -- I can't take my eyes off women in miniskirts.  I love those a pair of long, shapely legs.  (Too bad there's nothing of interest at the top of them!)  I wish I could wear a miniskirt on a regular basis for the same reason that women wear them:  they're sexy, provocative, and they provide men with easy access to our goodies.  I like to imagine wearing heels, thigh highs, a silky pink jockstrap, and a miniskirt to work.  Of course I'd have to keep my manhole nice and lubed.  That way my boss could more conveniently step up behind me, unzip his pants, lift up my skirt and pork me to his heart's content.

LINGERIE -- Sometimes I think I'd like to just buy out the entire lingerie section of a Frederick's of Hollywood or Victoria's Secret catalog.  women are so lucky to have such pretty, soft things to wear!  My favorite kind of lingerie to wear is a see-thru babydoll.  It's so feminine and frilly.  All I need is a babydoll and a man's dick up my ass to feel like a Total Woman.