Wait, so you’re a girl dressing as a guy?
::Checks link::
So, Lamia how you doin’? 
Yes. Unless I’m really a guy dressing as a girl who dresses as a guy…hmmm…Victoria/Victor? Nah.
Thank you, my dear. And let me just say that royal purple and gold is so YOU!
Someone oughta start a thread about that…
About ten years ago, when I was in college studying technical theater, my Stage Makeup class had a project–all the men had to make themselves up as women and the women had to make themselves up as men. It’s not as simple as putting on mascara or painting on some stubble.
There’s a picture of me from that day; I am completely unrecognizable. I went from a pretty feminine looking 19 year old girl to a rough-looking, long-haired, 30ish man. My dad hates that picture. 
I’ve often fooled people I’ve known for years saying that it’s a relative of mine.
Well, there was the time I was taking a Bar exam and wore my then-wife’s pink nylon panties–strictly for luck, you understand. At the end I got up and left with everyone else, and was walking down a hallway when I realized my shirt had ridden up and my pants had slid down, so anybody behind me could see that I was wearing pink nylon panties.
I made a beeline for the nearest restroom, made sure my pants were pulled up to my nipples, and scurried out to my car pretending I was somebody else.
Now, Mr killdare has been in drag a couple of times. And may I say he makes a lovely woman. Most recently he got dolled-up to be Scary Spice for Halloween a couple of years ago (I was Ginger). We had another guy as Sporty Spice, but let me tell you that it’s more than a little unsettling to watch Sporty get drunk and lose her wig after she’s had a a few too many Tequizas (gag).
But back in college we had an elaborate plan to disguise Mr killdare (then just my boyfriend) as a woman to hide the super secret fact that he had accompanied me on vacation. The parents didn’t know that as soon as my father made my plane reservations, Mr killdare had called immediately afterwards to secure his seat beside mine. I was only 18, and my parents were particularly protective. Anyway, my mother insisted on either dropping me off at the airport or picking me up, and Mr killdare could do the other. We told her he’d drop me off, so if we got caught on the way back it was too late to ruin the vacation. But then we were struck with the breath-takingly clever idea to dress him as a woman on the trip home, so he could slip off the plane unnoticed by my mother and we’d have pulled the whole thing off and my parents could continue to believe in my unfaltering virtue.
Mr killdare’s sister and I dressed him up in a smart little skirt and blouse combo and dragged him out into the world for a test run. Pretty as he was, he still looked like a guy in drag and no one at the grocery store seemed to accept him as a woman who happened to be cursed with trendy Luke Perry sideburns.
And just so you know, my mother was delayed in returning from her own trip, so my brother picked us up from the airport. Evil prevails!
[sub]I am ever so anxious for this Coldfire-in-kilt photo.[/sub]
I’ve never seriously cross-dressed. I haven’t taped up my chest (not that I’ve got a lot there) or drawn sideburns or anything. But I have had fun dressing as a guy a few times.
When I was about fourteen I dressed up a male farmer for Halloween. I wore a flannel shirt, overalls, and a straw hat, with my hair tucked into the hat as best I could. Not very sophisticated, but it was fun.
The next time was when I was sixteen and had to do a presentation for my history class. Now the teacher had said that we were supposed to dress nicely, which he specified as meaning suits and ties. I’m sure he assumed the girls would dress appropriately on their own, and that he meant the clarification to be directed toward the guys. However, I couldn’t resist. So I didn’t wear make-up and put my hair in a ponytail, and wore my brother’s suit, shirt, and tie. I couldn’t bring myself to wear his big clunky shoes, so I wore heals. I had a lot of fun, but my teacher didn’t say a word. I wore approximately the same outfit for a debate for the same teacher in my government class the next year, and for a video for my German class.
When I was at Cal Poly, my WOW (Week of Welcome) group cross-dressed for the farmer’s market. It wasn’t too serious–we all went to a thrift shop to get the stuff, and tried to get the ugliest stuff we could find. I ended up wearing loose brown corduroys and a white T-shirt with a turquoise and black striped overshirt. I think I just wore some ugly masculine shoes I had, but I don’t quite remember. I didn’t have the best costume, but it was a lot of fun. I’m usually rather reserved and quiet, but wearing a costume can be quite liberating.