Ideal Situation:
I would be as passable as I could possibly be, with long, styled hair and professionally done makeup, shaved smooth and wearing a tight pink dress and matching heels. My date would be well-built, with just a bit of stubble, and taller than me even in my heels. We would dance, drink, and laugh for a while before he pulls me in for a deep kiss. We would kiss for a while, my arms around his neck, while his strong hands roam all over my body, until finally he takes me back to his place for a long night of rough, passionate sex.
With a woman, it would depend on whether she's interested in me as a man or as a crossdresser. If it's as a crossdresser, it would be the same scenario as above, just with her in place of the man. If she likes me as a man, I'll just wear a nice shirt and pants. In either case, she would ideally be slim, waifish, around my height, and wearing a nice dress and heels.