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.
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
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,
Hit the stores the day after Halloween, when all of
the greasepaint and french maid costumes are
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
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
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
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
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
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
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
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
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
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
Bright colors jump forward, dark colors recede.
Remember this when applying make-up and selecting your
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
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
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
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
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
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
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
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
Don't bother with the Wonderbra. Unless you've got
really big manboobs it won't do much for you but make
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
Try some subtle highlights just above your eyelashes
and just under each brow... it'll make your eyes look
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
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
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
Keep all your receipts.
Women's sizes are just screwed. You'll learn that
sometimes big is too small, but sometimes small is too
Your penis is not a tragic flaw. It's your special
place. Some of the best girls in the world have a
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!