In America, it’s Halloween

The wildest New Year’s Eve parties in Thailand will have men showing up dressed as women. In America, it’s Halloween. My topic here isn’t very much about Halloween, which took place last late month, but is there something about getting into drag that fascinates us — both straight and gay men.

To me, getting into drag, which usually happens on Halloween night, is done only to entertain friends in a party. It’s our own group of friends’ tradition in East Hampton when we welcome the autumn season with gaiety. And on that night, to make them laugh, make them laugh, make them laugh is everyone’s contribution to the group.

But I definitely have to make sure that I really look good in drag too. You’ll never catch me dead in ugly drag. The ‘make them laugh’ part in my case does not mean I will dress up as Miss Piggy, Jersey Shore’s Snooky, or a witch. I want to knock them dead with my utmost superficial beauty.

The fascinating part is that it takes guts for us men (both gays and non-gays) to pull it off. For a man, if he wants to dress up as a woman, it still takes guts, especially the first time. The question in our minds is ‘should I or shouldn’t I?’ I think it really depends on the individual. Some may dive into it naturally with joy, while some may have to struggle with reservations, or (shall I use the word) hang-ups. Some may find it offensive. That’s why I’m just going to stick with only my own experience of getting into drag to tell you all about it.

Pizza Face

First, I found wearing real or complete womanly make-up makes me look ugly. My face looks like an overly-baked pizza. So, most of the time, since I’ve been in drag —about 7 times so far in my life — I only put on lipstick and nothing else, not even powder. Perhaps that’s my secret of looking beautiful naturally (God help us!). The wig is a big plus though. Once I put the wig on, it’s a go from there.

Anyhow, to me to put on a wig and sticking colour on my lips are the easy parts. The hard part is the brassiere. How do women clip their brassieres in the back, on and off, day in and day out? Worst all are the high heels. It’s very difficult to walk in them, and we are not even talking about those killer platform shoes of Lady Gaga.

Also, the silky, long black gloves are great to cover our man-sized hands. I must admit they make me feel glamorous, but it’s difficult to hold a glass, open the doors, turn on the bathroom light, etc. Do women take these long gloves off at the dining table? As I found it to be terribly difficult to use cutlery with them on, everything keeps slipping off my hands. I guess it takes a lot of training or getting used to.

Exposed to Drag

I was first exposed to big shows of drag on Halloween in San Francisco in 1967. Believe it or not, it was much ado about everything, perhaps, for the whole town. Limousines were ordered three months in advance, and most requests were for the convertibles. The gowns were more or less couture which took weeks and weeks for all the fussing and the fittings. On the night of Halloween itself, make-up artists all over town would go nuts with customers’ demands, from those wanting a Ginger Rogers or a Zsa Zsa Gabor look, to a Cleopatra, Helen of Troy, and Mata Hari, etc.

The most adventurous of them all back then were a group of rich gay men in San Francisco who took the whole thing a lot more over the top than the rest. Not only just expensive gowns, gloves, hats, shoes and all. They went out and bought real diamonds, too. We are talking Tiffany’s. These days I still remember Tiffany’s taking out ads in San Francisco prior to Halloween night, which said plainly; ‘Tiffany’s reserves the right not to sell diamond necklaces to men for their own use.’ It was that drastic.

It’s something that Tiffany’s, or Cartier, Harry Winston, or Van Cleef, etc. would never ever do today. It’s downright discriminating or sexist in reverse on top of the reversal. But to be fair to Tiffany’s; since way back when, the original creators of the company always put women first. Men were counted on to walk in and buy diamonds for their women, not for themselves. As Tiffany’s once suggested very strongly, diamonds are for women, exclusively.

Each Halloween night for the three years I lived in San Francisco before 1970, was a festival which I never had seen the likes of before or since. There were parades of the convertible limos. The well-to-do drag queens, or the faux dames with real diamonds and — guess what — real furs on top of all that, perched proudly on top of the back seats. It’s certainly a night for them to celebrate their vanities and fantasies to the max. In the early evening, the limos would take these drag queens up and down all around the hilly streets of San Francisco, showing them off and letting them accept acclaim from the public, all over Pacific Heights, Nob Hill, and Russian Hill.

Around midnight onward, all wound up on Polk Street which, at that time, was the major gay street. The long street itself is mostly flat but very small with two-way traffic. On such nights, both sides would be filled with drag queens in limos. They would go back and forth slowly, passing one another on Polk, over and over, while the far-too-done-up San Franciscan males/damsels, in their darndest dresses, dripping with diamonds, real and fake, waved their hands and blew their kisses, greeted one another from car to car. Greetings of ‘dah-ling’ and ‘honey’ were exchanged. The extra eye-candy sometimes was the drivers and escorts — good Californian blonde boys in their formal uniforms and movie star suits. All of the festivity and hoopla would go on just like that all night until dawn and a good time was had by all. What a night for once-a-year femme-fulfilment for gay men.

One thing is certain — at least in my case and for a lot of my friends in the west — getting into drag, if successful, becomes addictive. We may wait a whole year for the next Halloween night, but it’s still an addiction of some kind. It’s so much fun with no harm done to anyone, so, why not. The same may be said for some on New Year’s Eve night in some parts of Bangkok.

All in the Family

But my most startling experience of getting in drag was when I wasn’t in drag at all, but while I was a judge at one of the drag contests at a gay club on Silom road, one Valentine’s night.

That was long ago, last century. While judging, I saw someone win the Miss Congeniality title for no good reason. He, the contender, didn’t do good drag. He/she was too big, too tall, and too old for a drag contest, at least the one I was judging (look who’s talking).

But, that night’s Miss Congeniality, which had nothing to do with us, the honourable judges, won not because he/she was super-friendly, but because he/she got most of the bouquets brought to the contestants on stage. As a matter of fact, the winner got too so many. Those bouquets were sold by the club itself to make money and they were ridiculously expensive. The rule was whoever got the most of the bouquets would automatically be Miss Congeniality. In other words, that night, it was pure politics that this particular drag queen got nearly all the bouquets there were, while a lot of really beautiful and sweet, friendly contenders got none. In wonderment, I turned and asked the judge next to me: how did he/she get that many bouquets?

My colleague’s answer: they were all bought for him by his wife. Wife! Now I was really surprised. Then my fellow-judge pointed to a simply-dressed woman sitting quietly in the audience with a group of kids, really young kids who all looked bewildered and totally out of place. The judge whispered softly into my ear: ‘That’s his wife and kids.’

And I thought I’d seen everything.