Ciao!
From time to time you have to face the fact that some men will chase anyone in a skirt, quite literally. How should we deal with this? If you do find yourself being hit on whilst cross-dressed, it does help if you have bags of self-confidence. Either that, or fake it well enough that others won’t know the difference.
I once went to a meal out with friends from my writing group, and we’d decided on a general sartorial theme of “something that takes you out of your comfort zone, or other people out of theirs.” This theme was tempered by the fact we were eating in an Italian restaurant in the city centre, so we didn’t go over-the-top or anything; just goth makeup, leather kilts and me in PVC leggings – that sort of thing.
Over the course of the evening, I was hit on by three Italian waiters. I suspect the first tried to set up the other two as a prank, but I’ll never know. I also reckon they told the chef, because every ten minutes or so, a Slavic face popped out from the kitchen door to stare at me. When I tried to avoid laser-eyed Boris, or an ingratiating ‘”Hey, ciaoooo!!!”, I found myself being stared at by a guy I think of as ‘Wistful Dad’, who was eyeing up women at other tables, presumably to take his mind off the wife and kids sitting with him. I was directly opposite him, so caught him looking at me …a bit too frequently. My girlfriend (now fiancee) was sitting next to me and thought it was hilarious. At least it was a controlled environment, surrounded by friends, and we could leave easily.
More recently, I went clubbing for the first time in 20 years (I decided dancing wasn’t my thing when I was a teenager). A friend in York was celebrating his 40th birthday with a fancy dress party. After a few months of watching my diet more carefully than usual, I went as Lara Croft: blue vest, unignorable cleavage, and those tight, nad-mashing leather shorts which make me feel practically functionally female…
Boy, they really like Lara Croft in York! Especially on a Races Night. I think I had a dozen requests for people to have their photo taken with me around the streets – usually after they realised I was a guy…
Anyway, in one pub, a woman approached me and said, “‘ere, you are a bloke, aren’t ya? Me ‘usband’s been starin’ at yer arse fer ‘alf an ‘our! Come with me a minute, will ya, luv?”
She then introduced her husband and I to each other, thusly:
“You’ve been starin’ at a man’s arse, ya silly sod! Go on, tell ‘im!”
I just shrugged.
“Yeah, I’m a 38-year-old man,” I explained, “All it means is you like things that look feminine.”
He didn’t say anything. He just stared, slack-jawed. A couple of groups at the tables behind him applauded and took photos with their phones. I don’t think there’s anything I could’ve said that would make him feel less embarrassed (“Hey, c’mon, don’t be sad – everybody loves buttocks!”). There was simply no way his wife was going to let him forget this. Ever.
After the party a bunch of us went to a newly-opened nightclub, still in costume. As I said, I’m not much of a dancer, but I was up to my eyeballs with Red Bull and I simply thought “fuck it.” On the dancefloor, a drunken racegoer tried grabbing one of the women in the group, going for her wig. Being a wearer of a feminine wig, I’m kind of sensitive about that sort of thing. But mostly, I just couldn’t believe that some prick would do that to someone he doesn’t even know.
“DUDE – NOT COOL!” I barked.
He looked at me and I can only assume his brain did that blue-screen-of-death you get with a crashed computer. I could see the cogs weren’t going around – they were just jammed in a kind of “Lara Croft… but it’s a guy… Lara Croft… but it’s a guy” groove. (The woman he grabbed gave him a fearsome earful. Do not mess with Yorkshire women; they’ve had to deal with Yorkshiremen.)
Going clubbing in a blue vest and tight leather shorts is either very brave or very foolish.
A month later at the end of the Edinburgh Fringe, after emceeing a show on the final night, I was faced with a 45 minute queue for a taxi at about 1.30am. Or, I could walk home in heels in 20mins. I walked. (But not before a random punter asked to take a photo of my chest. I said yeah, sure, whatever floats your boat…)
I made it a less than a couple of minutes down a steep, cobbled street when a guy jumped out, presumably to scare first girl he saw. Except I’m not a girl, nor scared. His brother and brother’s fiance standing nearby pissed themselves laughing. The fiance asked me how I got my tits like that and showed me hers (erm… you don’t have to do that, really!); the brother mocked her for taking fashion tips on how-not-to-be-flat-chested from a guy. I told her to work with what she’s got, which is more than what I have. Then the jumper came out as a closet cross-dresser with a *ton* of questions for me. Feeling charitable, I answered them all (jeeeeeeezuz). Anyway, after a group photo and handshakes and smiles, we went our separate ways.
Five minutes up the road, and a guy in too-tight jeans and a smart shirt, looking like the last dregs of his youth were slipping from his grasp, looked me up and down (I was wearing a rainbow-coloured Space Invaders dress, if that helps explain things).
“Awwight, dahhhlin’? Fancy comin’ back to my place for a pahhhhty?”
I hadn’t taken my heels off*, so my sole tactical manoeuvre (“Run away!“) wasn’t an option. I would have to rely on bravado and hope things didn’t turn nasty.
I sighed.
“Dude. I’m tired, footsore and busting for a piss. I’m in three pairs of Spanx. All I want to do is go home, take all this crap off, have a shower, and sleep. If you’re still interested, you’re out of luck.”
Happily, I appeared to have sassed him into silence/ submission/ mental-bluescreen-of-death. I think my 38-year-old-guy-voice helped. He looked really dopey for a moment (kinda like the buttock-fancier in that York pub) and walked silently away (it was a busy-ish road, thankfully). I was mightily relieved to get home without further incident.
Moral of the story? Well, I don’t have one. These are all just one-off incidents and I’m not going to generalise from them. All I’ll say is that cross-dressing may not let me know what it’s like to be a woman, but I think it gives some fascinating insights into what it’s like to be seen as a woman… and that’s a lesson I think a lot of guys could benefit from.
I had no problem hailing a taxi dressed like this.
*Heel-wearers might question this choice – I can only assume you’ve never seen the state of Edinburgh’s streets on the last night of the Festival…
Miss Twist speaks her brains 
