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How to Be a Girl: The Things Every Beginning Transvestite Should Know

By Ursula Hitler

Author's Note: In the last few years I've spent a lot of time experimenting with drag and tracking down every book, magazine and website about crossdressing that I could find. I learned a lot, but I've also tried a lot of things that just didn't work for me. Below, in no particular order, you'll find the stuff I've tried that's worked the best, along with my own observations about the drag lifestyle. Even if you're a real girl, you might find some useful tips here. Enjoy!

Don't be scared to go shopping for women's clothes. Most folks assume you're shopping for a girlfriend. No matter how much you think everybody in the store is staring at you while you browse the ladies' section, they probably aren't. It's a good idea to bring a friend along for emotional support, and if you take a lady friend, everybody will think you're shopping for her.

Buy bras based on practicality first and looks second. For a tranny, bras aren't for showing off, they're for keeping your fake boobs on. You want a comfortable, solidly constructed bra, preferably with good padding. To find out your numeric bra size, just wrap a measuring tape around your chest, across the nipples.

Getting real boobs of your own isn't a simple matter. Hormones can mess up your health, they'll definitely make you sterile over time, and they're less and less effective after age 20. The herbal stuff ain't much better. Breast-implant surgery is expensive and has health-risks of its own, but if you really want boobs, it works.

Hit the stores the day after Halloween, when all of the greasepaint and french maid costumes are discounted.

You don't have to go broke shopping at those special tranny stores! Companies that cater to transvestites will try to convince you that you need stuff custom-made to fit your "special needs", but don't believe them. For most things, you can shop at the same stores as a regular girl. There's no reason you should pay $150 for a size 13 pump!

Clothing from Frederick's won't last long, but they make stuff in sizes to fit the biggest girl, you can order from them by phone or online, and their prices aren't too bad.

You can camouflage dark, stubborn stubble and razor burn by covering it with dabs of orange-red lipstick, rubbing it in, going over it with thick, creamy foundation that matches your skin tone (the liquid stuff won't do it), then going over that with powder, taking care not to smear the foundation. You can then blend the whole thing with a dash of blush. (See Footnote)

If you have a long, droopy nose, you can make it look shorter by shading the bottom with a little blush. Keep it subtle!

Heels aren't just cute, they also help give you a girly shape by pushing out your chest & butt. You'll hear a lot of real girls whine about how much heels hurt, but those girls are wimps.

Sex-changes aren't perfected, and many who get them never regain complete sensitivity in their genitals. You're best off learning to love your willie.

If you're scared to shop for cosmetics, wait until the middle of the night, go to a 24-hour supermarket, and pick up some cosmetics along with your groceries. The clerks will probably assume you're shopping for your girlfriend. If you really want to fool them, buy some tampons, too.

Define your jawline by shading along the area just beneath it with some blush.

Take karate class, carry a gun, or perfect a repertoire of devastating quips. And learn how to run real fast in heels. Don't get paranoid, but always be prepared for creeps.

Never, ever walk on grass in stiletto heels.

Slim your shoulders by standing sort of like a military cadet - chest out, shoulders way back. It works!

Some stores sell fake boobs for hundreds of dollars. Don't buy them! If you shop around, you can find decent fake boobs for fifty or sixty bucks. You can also get decent results by tightly stuffing two stockings with birdseed and then tying off the ends. The tied-off ends make good nipples, too!

Anna Nicole Smith is fat. Meryl Streep has a big nose. Susan Sarandon is old. Marlene Dietrich has a deep, deep man voice. Milla Jovovich has no tits at all. Sandra Bernhard is weird-lookin'. All these girls have something "wrong" with them, but they're all sexy in their own ways. Skinny, 20-year-old blondes with button noses aren't the only sexy girls in the world, so don't beat yourself up for not being one.

It's probably a good idea to experiment at home a few times before you make your first public appearance, and if you look horrible the first time you get dressed up, don't despair. You're learning, and with time and effort you will look better, I promise!

Even if you'll never be able to "pass" as a real girl, don't let that stop you from being as beautiful as you can be, and having fun.

The way a dress is cut affects the way your entire body looks. Some dresses will make you look short and fat, some will make you look taller and slimmer. If you're not happy with the way you look, try a different dress, and it just might change you into a completely different girl!

The police are not your friends. Most cops are macho louts who take particular delight in harassing transvestites and other sissy-types. Do whatever you have to to avoid crossing their path. When you're out in drag, be careful not to break any laws or do anything else that could attract the attention of cops. That means no driving fast, no buying drugs, etc. If a fight breaks out in your vicinity, run away! You don't want to be there when the cops show up! Few things in life are less fun than spending a night in jail dressed in drag.

Women's shoe sizes are generally one and a half sizes smaller than men's, but the only way you can really tell if a shoe will fit is to try it on. If you can't find shoes big enough to fit your feet, try shoes in the biggest size you can find that have open toes and/or backs.

You can hide your willie by tucking it down, wearing a tight pair of panties, and another, looser pair over that. Or don't hide it at all -- girls look cute with a hard-on! Don't buy one of them crazy "gaff" things! Fair warning: getting an erection while tucked can hurt. A lot.

Sex in drag is always tricky, because you have to worry about all of your girly parts falling off. Just get a wig that really holds on to your head, make sure your padding is well secured, try not to get makeup smears all over the sheets, and go crazy.

Payless sells good, cheap, big shoes.

Keep a wig on by wearing a wig-cap (for sale -- cheap -- at any drugstore) and safety-pinning the wig to it. Make sure those pins don't show through the wig, and make sure they don't poke you in the head!

Your wig probably has washing instructions -- use 'em!

Once you've applied the glue to your false eyelashes, wait a minute for it to get sticky before you apply them.

Lipstick is tricky at first, but once you get it down it's not so tough. Try this: pencil on some lipliner first, then color in the outline with lipstick, just like you're using a crayola in a coloring book. Now, gently kiss a piece of tissue to blot, then powder your lips, blowing out so you don't breathe in the powder. Repeat from the beginning, and your lipstick should stay on all night. Some folks suggest setting your lipstick by placing a sheet of thin tissue over your lips and powdering through it.

If you yearn to go out in public wearing women's clothes, do it now, while you're still a fresh young thing! Every minute you spend at home feeling like a pervert is a minute you'll regret once you realize how fun it is to be a pervert in public.

If you're nervous about shopping, perfect your "zombie face," the sullen, sleepy expression that most men have when they get dragged to the mall by their lady friends. Practice looking like you just woke up. If you look bored while browsing through the ladies' racks, people might assume you're shopping for a girlfriend. Don't overdo it, though. You don't want mall security to think you're a junkie or something!

No matter how great you look in drag, sometimes people will laugh at you. They don't necessarily mean to hurt your feelings -- they've just been conditioned by Benny Hill and Milton Berle to think of drag queens as big clowns. Show 'em drag queens mean business by seducing them.

High heels only hurt if you stand or walk in them. Sit regally at the center of attention, and only walk around when the occasion demands it.

When you're all dressed up, you might find another, unexpected personality emerging. Don't fight her -- maybe she's the real you!

Buy a purse. They're so useful that you'll wish you could have one when you're dressed as a boy, too.

If you can't remember what to carry in your purse, you're always safe with the BLEWTICK system: Brush, Lipstick, Eyeliner, Wallet, Tissue, ID, Compact, Keys.

Until you've figured out your sizes (or even after), you can probably get away with buying stuff that's labeled small and has a lot of stretch. I'm almost 7 feet tall in heels, and this works for me!

A girlish waist is a must, so it's time to do those tummy exercises! In the meantime you'll probably need a corset, but don't spend hundreds of dollars at some bondage place unless you really want to. You can get a workable waist-cincher at Sears for like $20.

Please, please don't go to one of those drag makeover services. They'll charge you a lot of money, and you'll probably come out looking like your mom.

Black underwear is fun, but underwear that matches your flesh-tone shows less under thin outfits.

Make cleavage with duct-tape. Just lean forward, and pull your pecs together with one hand, then tape 'em tightly together with the other. If you have a hairy chest, shave before you tape! Taping directly across your nipples will give the deepest cleavage, but if you do this be sure to put band-aids over your nipples first. When you're done, your chest will look kinda like a pair of butt cheeks; you can create the illusion of space between your pecs by subtly shading between them with a little blush. To make sure nobody spots your tape over your neckline, try black tape under a black bra. When it's time to take the tape off, a warm shower will loosen it up some, but it'll still hurt like anything.

When you're out and about in drag, use the ladies room. No matter how uncomfortable it makes you, it's preferable to the alternative.

If you've got the guts, tell the world you're into drag. Some people will freak out, but plenty more will think it's interesting! Don't be a windy bore about it, though.

Elbow-length opera gloves are beautiful, and they give the arm a lovely, graceful look. Plus, they save you from all the complications of painting your nails or wearing those damn press-ons!

As a rule, girls have thinner, higher, more widely-spaced eyebrows than boys. You can simulate that look by defining your brows with eyeliner pencil. Shaping them a bit by trimming or plucking is a good idea, but don't get nutty about it. Big brows are cute, no matter what the drag queen eyebrow mafia says. I'd caution against a big uni-brow (eyebrows that meet in the middle), but hey, it's your face.

If any of your real hair shows under a wig (your temples for example), you can temporarily color that part of your hair to match the wig by using artist's non-toxic acrylic paint, pastel chalk, certain shades of lipstick, or a product called Lancome's Hair Streaks.

Just like with your lips, when your eye make-up is all done set it with powder, then do it all again.

Liquid eyeliner is nice and dark, but it smears like crazy while it dries, so tilt your head back and look down while applying it. You'll probably still have to touch it up with pencil, too.

One of the best ways to make sure that your wig will look natural is to get one that exactly matches your real hair color. That way, you can be sure the wig will perfectly suit your skintone and eye color.

Always leave yourself a lot of time to get ready before you go out. If you think something should take half an hour, it will actually take an hour and forty-five minutes.

Mascara spoils over time, so every few months you gotta throw it out and replace it.

To make your eyes stand-out, add some subtle highlights just under each eye and along your forehead over each brow.

Camouflage dark circles under your eyes with a dab of smeared-in orange-red lipstick, some foundation, and powder.

Bright colors jump forward, dark colors recede. Remember this when applying make-up and selecting your wardrobe.

Don't take crap from rednecks, religious freaks, uptight feminists, your friends and family, or anybody else about drag being bad. They just wish they looked as cute in a skirt as you do!

If your boy-self likes girls but you discover your girl-self likes boys, then let your boy-self enjoy the company of girls and let your girl-self go crazy with the boys. Don't waste time worrying about your sexual orientation when there are cute people out there you could be french-kissing right now.

Maybe you think catty is sexy, but it's not cool to be cruel! Any bitch can put people down... it's an art to make people feel better. Smart, sweet people are the best.

If you have a cell phone and an auto-club card, take 'em with you when you go out! Do you really want to end up stranded someplace at 2 a.m. wearing a pink ballgown and glitter pumps?

You can make yourself some girly hips and a butt by cutting the legs off a pair of pantyhose, wearing the pantyhose like shorts, and stuffing the hips and butt with foam-rubber or other padding. It's a good idea to wear another pair of pantyhose or tights over this to smooth everything down. You might look a little lumpy, but at least you'll have a butt.

This isn't a "phase." Trust me, no matter how much you try to repress your gender confusion, those feelings are not going to go away, and the more you fight them, the more it'll mess you up. Quit feeling sorry for yourself, buy some goddam lipstick, and have fun.

Wearing crotchless tights under your panties greatly simplifies visits to the ladies' room. It also leaves you nicely accessible if -- heh heh -- anybody wants to explore beneath your skirt.

Girls who like to dress up as boys are called drag kings. If you meet one, do not, as far too many queens do, say, "Oh, you're so tiny and pretty! You could never pass as a man!" Maybe you don't mean any harm, but just imagine how you'd feel if somebody told you, "Oh, you're so huge and butch! You could never pass as a girl!"

The internet is a good thing; you can use it to make lots of new friends, find drag events in your area, and learn useful tips... like these!

If having a girly voice is important to you, study the speech of a particular actress or any famous woman whose voice you like. Inflection is much more important than pitch. Nobody ever thought Kathleen Turner was a man, did they?

Shaved arms could lead to embarrassing questions during short-sleeve weather. Have a cover story ready. You could always say you're a competition swimmer or cyclist, people who shave their body hair as a matter of routine. If I'm wearing short sleeves and somebody asks about my hairlessness, I'll say, "Ah, I've just never liked having a lotta body hair. It makes me feel like an ape or something." Then I change the subject in a hurry. If I'm wearing a long-sleeve shirt to cover up, and anybody asks why I'm dressed like that on a warm day, I'll say, "Jeez, my cat's fleas are so bad this time of year... They've bitten my arms up something awful." Both stories sound a little nutty, but it's simpler than telling the truth. It's important to keep in mind that completely shaved, smooth arms are a lot less noticeable than arms with a lot of short, dark stubble.

Shaved armpits are sexy (good for cutting down on b.o., too) but if you don't wanna do it, don't! Madonna got pretty far with bushy pits, didn't she? If you do shave, trim with scissors first.

There's no rule that says you can't have a beard or muscles or whatever and also be a drag queen. If somebody dares to give you grief about it, flex your big queen muscles at them until they get scared and run away.

Study how women walk... small steps, with a rather straight-legged stride. I once heard some famous model suggest walking like you have a nickel clenched in your buttcheeks. Unless you don't really care about passing as a real girl, don't mince around too much.

If you're brave enough, you'll do yourself a big favor by using the dressing room to try clothes on before you buy.

No matter how happy you feel, a big grin is probably not a good idea. It makes a girl with a lot of makeup look like the Joker. Everything else you'll read about drag will tell you to smile, smile, smile! Ignore them.

Long hair is almost always prettiest, but if you're really wrinkly or droopy you might look better with a ponytail or one of those tall, piled-up hair-do's. Please avoid a medium-length, curly hairdo... It'll make you look like one of the "Bosom Buddies."

Consider your drag name carefully. You want a drag name with flair, but it doesn't have to be a total joke name. Your female self deserves respect!

Never hide your crossdressing from your spouse or significant other. If the two of you are meant to be together, you have to trust each other enough to not keep secrets. They don't have to participate in it if they don't want to, but if they love you, they owe it to you to support such an important part of your life.

Dancing in heels is a tricky business. Thick heels give you a lot more stability than stilettos, but it's still hard. Try planting your feet and moving your arms and swaying your hips a lot. Above all, don't think too much.

If your legs are veiny or scarred-up or you don't feel like shaving them, try a pair of flesh-colored tights with pantyhose or tights over that. Black tights will hide everything, and they'll also make your legs look slimmer.

Your wig is maybe the most important thing you'll wear... buy only the prettiest wigs! Wigs are like the number one thing most trannies get wrong. Before you buy a wig, really look at women's hairstyles, and carefully consider which style of wig would be most flattering to you. If a wig is pretty enough, the rest of you won't matter so much. Once you've bought a wig, you can't return it, so you'll either have to try it on in the store, have a girlfriend try it on for you, or just hope for the best. The best wigs usually cost a bundle... but not always! I've found some great wigs for like $30 or $40! I especially recommend the wigs at Hollywood Toy & Costume. They're cheap, and they have some that look really believable.

While you're out and about, check yourself now and then in the mirror to make sure nothing has smeared or fallen off or whatever.

If you're really conflicted about being a transvestite, please, please do not join the army, marines, police force, or any other fascist organization to prove to yourself that you're a "real man". There are already way too many repressed queens in those outfits who deal with their inner torment by making life hell for the rest of us.

If you're scared to shop in stores, you can always buy stuff online, or through catalogs. This may be obvious to some of you, but plenty of girls never figure it out.

Tight miniskirts are fun, but a dress with a big, full skirt has many advantages. A full skirt is great for giving a dumpy male body a feminine silhouette; it nips in your waist, and flares out your hips. Anybody can look like a woman in a big Cinderella ballgown! A full skirt also saves you from worrying about hiding your erection. Crinoline is your friend.

When you're first figuring out how to do drag, check out a bunch of beauty magazines and/or books for advice. Once you know what you're doing you can experiment, but for now it's best to have some rules to work with. It's a good idea to buy a magazine aimed at women in your general age range. If you're fifty, you don't want to follow beauty advice aimed at some teenager, and if you're 17, you don't want to be learning beauty tips more appropriate for some soccer mom. Pay special attention to their advice about what colors go best with your skin tone and which hairstyles are most flattering to your facial shape.

Shaving 101: If you have any thick patches of fur, it's best to trim them with scissors before you start to work, here. Done? Ok, then soak in a tub of warm water for a long time, giving yourself a good rub all over with a wet washcloth. Now smear on lots of shaving cream, preferably the gel kind, and let it sit for a minute. Begin shaving downwards, in the direction of hair growth. Use a razor made for "sensitive skin", and don't forget to tap out and rinse the razor in warm water often so it won't clog up on you! Now shave upwards, opposite the direction of hair growth... but do it slowly and carefully. Keep shaving until you think you've covered everywhere, including your chest, stomach, butt, hands, back, feet, or anywhere else where you might have some gross boy-hair left. Take special care around your nipples - you don't want to cut one off! Rinse off any remaining shaving cream, and pat yourself gently dry with a towel. You'll get your closest shave by shaving dry, but be careful! This is an easy way to bleed to death. You'll probably have killer razor burn the first few times you shave, but over time it gets easier. I'm told electric razors give the closest shave, but I've yet to try it.

Models in magazines look so perfect because they've got hairdressers, make-up artists, glamour photographers and airbrush artists to make sure they do. Real girls get depressed looking at models, too.

It's a sad fact that men generally look about five years older than women of the same age. By the time you're 26, it may already be a little late to be dressing like a teenybopper.

Moisturize, moisturize, moisturize!

They ain't glamorous, but Ross is still a good place to shop, and every now and then you can find some unbelievable $20 party dresses there, the same things you'd find at Robinsons-May for $300! It's also usually so crowded that nobody will notice you peekin' through the racks.

Depilatory creams are stinky and unreliable, and they can really irritate your skin, but they can work, sometimes. Just test them out on a small patch of skin first to make sure you're not allergic, then leave 'em on for the maximum amount of time specified on the bottle.

Don't bother with the Wonderbra. Unless you've got really big manboobs it won't do much for you but make you sad.

How much should you pad? Well, smaller is definitely more realistic, but unless you're trying to pass as a real girl, I say go as big as you like in the butt, boob & hip department. Who gives a damn if you look ridiculous, as long as you're happy!

Rain is a drag queen's enemy. So is heat. And daylight. Drag queens thrive best on cool nights.

There are lots of terms for boys who like to dress up as girls: drag queens, transvestites, crossdressers, transgenderists, and many, many more. Some people spend a lot of time arguing about the exact definition and proper use of each of these terms. Please don't be one of those people.

Be subtle with perfume. Spray it behind you, over your shoulder, then step backwards into the mist before it dissipates. You can also apply a dab of perfume behind each ear, and on each wrist. Perfume doesn't have to cost a lot, so long as it smells nice.

Don't try to cover wrinkles with a lot of make-up... it'll just settle into your wrinkles, emphasizing them even more! Put moisturizer on your wrinkles, then try and emphasize your non-wrinkled areas with makeup.

Don't be mean to real girls just 'cause they got so lucky.

Try some subtle highlights just above your eyelashes and just under each brow... it'll make your eyes look soooo dreamy.

When you get home from an evening out, wash your face thoroughly to get every bit of make-up off. Failure to do so can lead to nasty acne, and can even contribute to your skin getting wrinkles later on!

It doesn't matter what you look like, if you go out to drag clubs, you'll probably get hit on by a lot of really gross and/or scary guys. Now's your chance to learn what girls are talking about when they whine about how they can never get left alone at clubs. Don't expect to be raped or anything, but go in knowing that many of the people in a drag club are looking for sex, right now, and they're not going to be subtle about it.

If you're a wacky, flamboyant queen, there will be people who give you grief about being a "caricature." If you're a subtle, elegant queen, there will be people who will give you grief about not being "outrageous" enough. Don't worry about pleasing everybody, because you never will.

Remove eyeliner with a wet, soaped-up Q-tip. And wet tissues. And a towel. This could take a while. Almay sells makeup remover pads that help a bit, but when you're all done you'll probably still have little traces of liner left. I usually de-emphasize these traces with a bit of powder.

Accept compliments gracefully. If people say you're pretty, don't freak out, but don't get a swelled head either! Learn to say, "Why, thank you! You're so sweeeet," in that cute, sing-song way real girls do.

Being a drag queen doesn't mean you have to like Judy Garland, or that you have to say everything is "fabulous!" all the time. It also doesn't mean you're neccesarily gay. According to statistics, most transvestites are straight!

You can slim down a thick nose with a little blush on each side and a subtle highlight down the center.

If you're shy, going out to drag clubs alone can be really hard. If you want to make friends fast, look around the club for somebody who is also alone, walk up to them, and compliment them on their outfit. We queens are suckers for flattery. Once you've broken the ice, you can ask where they got their outfit, if they came alone, how long they've been going out in drag, etc.

Nobody says you have to dress like a Vegas showgirl with feathers, spangles, etc. Dress like the kinda girl you think is sexy!

Waxing works, but it really hurts. My ex-girlfriend swears by packing tape... just put it on your skin and rrrrip it off. Yowch!

Pluck or trim your nostril-hairs, please.

Try two different shades of lipstick, lighter on the lower lip, darker on the top. Yummy...

Comb out a wig with a brush that has big, widely-spaced bristles. Comb with care.

Just before Christmas and Valentines are especially good, inconspicuous times to shop for dresses and lingerie.

Not only do many big-city stores not give a damn if you're a boy shopping for girl stuff, some of 'em actively seek tranny business. Once or twice clerks have figured out I was shopping for myself, and they invited me to use the dressing room!

Please don't get too extreme with the rouge.

Clip-on earrings will pinch like anything by the end of the night.

It's generally best to dress as old as you look. Young queens can dress older, but an old queen dressed like a kid can be pretty tragic.

For some reason, even the longest, prettiest boy hair usually doesn't work well for drag queens. You need a wig!

Keep all your receipts.

Women's sizes are just screwed. You'll learn that sometimes big is too small, but sometimes small is too big!

Your penis is not a tragic flaw. It's your special place. Some of the best girls in the world have a penis!

To thine own self be true.

Footnote: Unfortunately, many of my makeup tips won't work very well for our African-American sisters. Sorry, I just don't have any experience figuring out makeup for brown skin. At least all my other tips should be useful, though!


Copyright © 1999 by Ursula Hitler All rights reserved. Not to be distributed, reproduced, or transmitted in any manner without the express written permission from the author.

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Ursula Hitler is a writer/artist/transvestite who lives in Los Angeles. She takes her name from a line in an obscure and not terribly funny Monty Python sketch, but she likes to tell people she's really Adolf's great grand-niece. For more of Ms. Hitler's wit and wisdom, check out her sprawling website, Ursula Hitler's Filthy Mind.

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