Welcome to Kinkytown, Kyle and TCB! There's a number of crossdressers and genderbenders walking around the place, or guys who'd like to be dressed as chicks while dominated, bound and fucked.
Physically I'm the XY type myself, though with a body that happpily lends itself to transformation and masking: tall, lean, very slight hairgrowth on my legs and chest, slender hands, and I've been turned on by the ideas of posing as a girl and of being bound, dominated and used for many years (on these boards, I'm to be considered a girl). Those leanings are not outright dependent on each other to me, and realizing the bondage/sm bit came before going along with the trans thing (it is more sexy to be bound and tortured as a girl though: a hogtied male doesn't look terrific, a hogtied, struggling woman or convincing transvestite looks great). Yes, I also feel that being on your knees and sucking a thick male cock, preferably with your wrists bound on your back, has something quintessentially submissive about it, it robs you of both your free will. your male dignity and your speech, turns you into a slutty love toy.
I remember one of the first times I went to this club I'd gotten in touch with, a closed society of dykes who were into bondage, leather, latex, uniform and roleplaying. I had been on their mailing list for some time (found this group on the internet somehow) and finally summoned up the grit to go to one of their nights (the theme was to be "Women's prison" - like in Prisoner Cell Block H and the like. I didn't have any girl I could involve in helping me with make-up, dressing etc or getting me there, had to do it by myself. I acquied a bra, a knee-length skirt, eyeliner, lipgloss and some other make-up articles (I didn't have much before) and a fresh set of panties, and set about preparing (none of the shops made any looks at me, a guy, buying this, not the lady who sold the skirt sither - I said it was for a dress party).
So I went by public bus to the neighbouring town, missed a stop and had to walk an extra half mile along a deserted throughfare (didn't meet anyone there I think). Then came the unexpected trouble; I don't really know that part of the neighbouring big city that well, though it's a quarter with a lot of bars and clubs and youthful population. I'd drawn a careful sketch of the streets around from the main bus station and up to this joint, from the map in the phone book. Unfortunately, the map there didn't indicate that one of the streets changed its name midway and some other detail, so that sketch didn't seem to fit, and by no means were the streets signposted on every corner (I really should have checked the route in daylight before, but no time. for that..)
I got more and more nervous walking around these streets, looking for signposts and indications, trying to close in, dressed in a black knee-length skirt, dark panties,´glossy red lipstick, a not totally convincing stuffed bra (with cleft oranges and cotton inside!) though no cleavage in the shirt, and inexpertluy applied blue eye-shadow, and carrying a bag which had, at the bottom, below other stuff, about twenty yards of rope and a reel of duct tape. Yeah, some peiople noticed, and I recall a cab driver who yelled "f***ing tranny!" after me.
I wasn't scared shitless but i knew i had to find this place and get in, finally I asked two girls if they knew where that street was (it was one of the main streets of the district). They saw no doubt I was dressed-up but didn't bother, just gave me the good directions.
I'd hoped the club would be real flashy and stuffed with some weird & kinky people waving their whips and so on, i had fantasized about falling to my knees in front of a domme with my hands tied behind, kissing her toes and saying in front of sixty people "the slut Louise prays to be hung up and flogged!", punished and then made to suck somebody. It didn't happen quite like that. I was the only male-to-female dragster around and some of the proceedings didn't take off, but I know the initiation of actually being in the open, walking the streets dressed en femme and telling people openly about what I wanted, was important.
It's hard to pull off a convincing act of appearing like a lady so you can be sure to "pass" and not have the jarring feling of "hey, that's a dude", not even with peple at a gathering who are prepared. Pro drag artists have resources that no ordinary crossdresser can afford, and just getting the make-up right is a science in itself (and make-up to look like a female doesn't always equal ordinary women's make-up stuff). I know some who are really into this use latex face masks (with fitting holes for eyes and mouth etc) and carful colorations of the hair. That's not a solution I'd want and it still leaves the voice which is really hard to achieve and the profile around the butts and waist, and somehow avoiding to have your dick protruding (essential to get a skirt to look right). But okay, we're in tha Fantasies forum right now.