I've always hoped to find a g/f who'd be comfortable with my dressing up and our sploshing together but my experience has been negative, so far.
It seems that most people assume that someone who crossdresses is automatically gay (probably due to popular media stereotyping) which is completely wrong. (The vast majority of us are straight but it's mainly those who are 'out' who frequent gay clubs etc that get interviewed - the 'drag queen effect'.) The concept of two kinks with which most potential g/fs aren't familiar seems to be far too much for them to manage and you're treated like a mad axe murderer - to be avoided as rapidly as possible.
The trick is to show you can be a man when it counts.
In this day and age, transvestites aren't as unknown and scary as they once were and I personally have found most women dig it more than are repulsed by it (assuming you're not an ignorant, obnoxious perve, but if so that's not the fault of the frock). However, while this is good for fun and fantasy it's not a good opener for a relationship, because a straight woman has needs from her man that need to be satisfied by a man. Another common problem with an object fetish is that ultimately she'll need to know it's her you love and not the object of the fetish which she just happens to come along with. Never forget to consider what's in it for her.
Many women would like a boyfriend who's also a girlfriend, but when things get sexual there'll come a point when you need to take the man's role. It's all very well imagining yourselves as a pair of lesbians, but if she wants penetration, you ain't a girl no more, sunshine.
(as an aside, this is a problem even among gay t-girls, who often complain about being pulled by tranny lovers who then want to be the one to take it up the arse. But maybe this is too much information).
Worse is if your motive for crossdressing (as is sometimes the case) is as a way to abdicate responsibility or as a way to claim the perceived priviledges of the fairer sex. In the context of a relationship, this can become needy and selfish very quickly.
It can be done, but then the path of true love never did run smooth. Keep it positive, have fun and be prepared to give back and one day your ship will come in.
Oh, and one other hint that I was originally told by one of my magic mentors; don't run if you're not being chased. People will always assume the worst.
Good on yer, 2messy, here's to many years of fun together!
