The Crossdresser’s High Holy Holiday

Carmen Miranda — 2006

We can’t state it often or emphatically enough: Halloween is coming! Oh, and don’t roll your eyes like that, young lady. We know you know that Halloween is approaching. And we know that you know that we know … wait. Scratch that.

What’s important is that you’re doing something about it. And we don’t mean buying lots of candy in hopes there’s plenty left over once the neighborhood kids have come and gone. You are planning on going out this year, aren’t you?  Remember what happened last year?

You stayed at home. Came up with some lame excuse, and threw a sheet over your head to hand out treats.  And the next day, you kicked yourself, because you missed the one night a year adults are given license to dress up out of the norm.

Well, missy, it’s 2009, and time to quit making excuses. Get your girl on and get out the door! Start sending e-mails to your nearby BFFs, and get organized. If you’re not used to going out in public, there’s safety in numbers. If you’re in any kind of metropolitan area, there’s likely a TG support group of some shape, and its members are probably having some kind of a party. Wrangle an invitation, and go have some fun. No friends, and no club? No problem. If there’s a GLBT bar in your area, you’re likely to find someone else in a similar situation. If nothing else, you will probably make a new friend of some stripe, if you’re not too shy.

School girl 2003

But, let’s say you live in the boondocks: there’s no gay bars, no support group, and no other TG’s anywhere near you, (as far as you know). Halloween is on a Saturday this year. Drive somewhere where a T community exists. Make a mini vacation out of it. You have all day Sunday to recover. Besides, with the economy still dragging, (yes, we said that), motels are still desperate for guests.

Worst case scenario, you live 300 miles from the boondocks. Find a straight bar holding a Halloween party, hold your head up high, and have fun. It’s been done before. Patrons, whether they know you or not, will probably assume you’re just having a laugh. Especially if you keep a good attitude all night. And since you’re going out close to home, take friends. Make them all dress in drag as well.

But, Ronnie, (I hear you say), I go out all the time. Matter of fact, Halloween is kind of boring. What can I do?

Stop whining for one thing, and get thee a costume. Don’t just go out en femme; go out en femme in costume! Women-born-women don’t dress up for Halloween as women, they dress up as female characters.  You can do the same. (Though a note of caution: no matter how sexy the model on the costume package looks, it’s not the costume that gives her those curves. And it won’t give you the curves either.)

Get your TG friends together and get a theme. Go as the princesses from the Disney movies. All dress as maids, witches, vampires, or nuns, or vampire nuns who practice witchcraft and good housekeeping. We’ve got a group in Cincinnati, where for the second year, we’re all dressing like Dorothy from the Wizard of Oz.  Do that. Or all dress like Daphne from Scooby Doo. Or Velma, if that’s more your speed.

Friends of Dorothy, 2008

We had a blast as the “Friends of Dorothy” wherever we went last year, and were greeted on our bar crawl with much warmth. (Except for the GG who was dressed as Dorothy. She didn’t seem to be too pleased with us for some reason.)  We hit gay bars and straight bars, and lots of people, gay and straight wanted their pictures taken with us. (We also rented a limo so we didn’t have to worry about parking or driving under the influence.) And for the record, we had three TG Dorothy’s, and three GG Dorothys. This year, we tentatively have 12 Dorothys, including trans, GG, and straight and gay males.

But we hear you asking, what about the aftermath? What happens Monday morning, when a co-worker asks what you did for Halloween. Be honest. Tell them: I put on women’s clothing, and hung around in bars. Chances are good they’ll think you’re nuts, (which they probably thought anyway), or they’ll think it’s fun. (You’ll have to be the judge of your co-workers. You already know who’s cool, and who’s a tight ass.)

Just remember, if year after year, you ‘fess up to doing drag for Halloween, the sharper ones will guess your secret. And that’s okay. Because remember that feeling of liberation you had on Halloween night? That sense of freedom? That lack of guilt? Maybe, someday, with a slow cracking open of the closet door, you can feel that way year around.

Category: Transgender Opinion