Crossdressing?

Question

Hey i'm a guy thinking about trying it. Could somebody help me out to get started.

Answer 1

OK, for starters, you need to get an idea of what women's size you wear. Go to Goodwill or the Salvation Army because the clothes there are cheap and you can "guess" at size. After you have a pretty good idea what size you wear, you can invest in nicer stuff.

They sell outer wear but you will have to buy your bras and panties elsewhere. Men's undies go by waist size but women's undies are sizes like 4, 5, 6. My bf is a big guy so he uses women's panties in size 8!

Personally, I think he'd look better if he shaved his legs when he crossdresses but he doesn't want to go that far so he uses really dark hose. We have to order his shoes off the Net since he's got such big feet.

Careful who you tell. He made the mistake of telling a buddy and the buddy told his wife and she told me when we started out dating, figuring, I guess, that I'd dump him but I acted like "Who cares?"

It's easier for my bf because I help him buy stuff by pretending it's for my mother if we're in the store or by passing on catalogs to him so he can order stuff anonymously.

Answer 2

Good God, where to start?

Know your size is probably the best single piece of advice I can give you. Bust, waist, and hips are the big three, but you should also know your inseam, sleeve, and shoe size as well. Most catalogs and websites will have a sizing chart that will let you convert your measurements to sizes. Payless shoes has an excellent one for determining your shoe size and width. Bear in mind that most women are proportioned differently than men, so you may find that you only hit 1 or 2 out of the three measurements given for a particular size. For pants and skirts, your waist measurement is most important. For tops and dresses, your bust measurement is most important. It is not uncommon to wear one size in a top and another in pants or a skirt. I wear a size 16 in pants and skirts but an 18 in tops. And even that can vary depending on the design, cut, and / or manufacturer. Needless to say, when you take your measurements, wear whatever undergarments you will be wearing while dressed, especially if they are padded.

Underwear. There is no delicate way to say this other than most panties are not designed for "extra weight" you have down there. Ironicaly, you will have the exact opposite problem with bras. Neither problem is unsurmountable, but both require a little creativity. A gaff is basically a thong for men, that will allow you to tuck your penis down between your legs and hold it there. And yes, it is as uncomfortable as it sounds. Believe it or not, though, you will get used to it. As far as your bra goes, you are going to need to measure for that too. Again, websites and catalogs will help you here. Victoria's Secret is excellent. So is Lane Bryant if you are a little bigger. A bra has two measure ments, the band and the cup. Since you don't have breasts, you are going to have to make your cup size up. "A" is the smallest and they go way up from there. I am 6' and about 200 pounds and wear a 40D bra which seems to be in proportion to my body size.

Breasts - If this is something you plan on doing for a while, then by all means, invest in a good pair of quality silicon breast forms. They look and feel very natural. They are also a little pricey. A cheaper alternative is knee hi's filled with rice. A one pound bag of rice will create a nice DD cup. Adjust as necessary.

Makeup - Remember the old joke about how to get to Carnegie Hall? Practice, practice, practice. The same holds true for makeup. Unless you are extremely skilled and a little lucky, you will look like a clown after your first attempt. That's OK, I did too. Like anything else, applying makeup is a skill, one that will get better the more you do it. Starting out, look for a kit with everything in it. As you become more skilled at applying it, you will discover what works and what doesn't work for you and can build your collection from there. Drugstore.com has a neat feature that remembers your previous orders in a favorites list, which saves you having to remember what shade of lipstick it was that you really liked.

I could go on and on, but I think this gives you a good start. If you have any more questions, feel free to email me. Welcome aboard!! If you stick with this, I can promise you that it will be one of the most thrilling, frustrating, liberating, expensive, creative things you will ever do.

Answer 3

Confide in a girlfriend if you can. Chances are she will be happy to help you.

Don't be afraid to buy anything in stores or anywhere else.

With a little experience one can look good enough to draw little attention if that is what you want. If you pass well you will enjoy the attention.

I am 5"11" and 210 lbs and 51 years old. I go just about anywhere in female mode. Yes I am a male. I have even flown and been through airport security. (Only trick here is your Legal ID must match the name on your ticket, you have to use your male ID) .

Just practice a lot before venturing out, and do go out it is fun.

From personal experience If I am going to a bar, I prefer to go to a higher class straight bar. Gay bars are ok and are pretty much accepting but the people there are gay, and I like women. I say higher class because you are not likely to get in a fight or anything. Plus you can wear dressier clothes.

Two things to spend money on:

1. A good wig and have it styled, don't be embarassed. A wig salon will give you a private appointment if you ask.
2. Silicon Breast forms, they are getting to be under $75 or so Good brand is Curves.

Best of luck and keep your courage up.

Answer 4

Bra straps are uncomfortable and tend to slip so go with strapless.

No matter what the fashionistas say: ALL legs look better with hose of some sort. Just be aware that the slightest snag can spell disaster within seconds.

For a spiffier appearence, tuck the blouse into the top of the hose, this will keep it from coming untucked.

White makes you look fat.

Black is slimming.

High heels are a pain. Opt for platforms.

Do not match the lipstick to your nail polish.

Purses are black holes from which your keys, lipstick, whatever else you are needing at the moment never emerge.

That's about all I can think of for now. At least in being a guy you don't have to worry about starting your period while wearing white pants and the like.
Oh! Thongs, HIGHLY over rated. If you don't want VPL, (visible panty lines), don't wear undies at all, just opt for going comando in the panty hose. You'll have to go with them anyway to hide your...ah....candy and most come with the little liner thing anyway so it's just like having panties with legs.

Good luck!

Answer 5

do a search for crossdressing clothing and the site usually have size charts so you will know how your mens sizes corrolate to ladies. then start by going to thrift and second hand stores. buy panties at discount stores that way you can experiment w/o spending a lot of cash.. if you really enjoy it then you can get some nicer clothes... you can also find wig and make up tips on a lot of tg and cd websites depending on just how far you want to go with this.. i go all the way have for a long time and love being a "girl"

Answer 6

Someone uploaded a few videos to YouTube giving a bit of a "how to", but be sure to a) read the comments attached to each of them for a different point of view and b) don't be afraid to experiment with your look and find what's right for you.

Part 1: http://www.youtube.com/watch?v=G_rLPm0w5JM
Part 2: http://www.youtube.com/watch?v=uZzhwWlrj8E
Part 3: http://www.youtube.com/watch?v=iMv3tQU5xvY

Also, you can find some advice at the crossdressers.com forums. Some Yahoo Groups are good, but there are also a lot that are just filled with people spreading pictures of themselves in their panties so...proceed with caution.

As for buying clothes, thrift stores can be good. eBay is also good for clothes at cheaper prices than retail.

Lastly, pay attention to the genetic women around you. See how they dress, do their makeup, and behave. If you want to "pass", you have to find that happy medium between acting like the male you've been raised to be and the exact opposite you will instinctively try to act like.

Answer 7

There are tons of good resources about getting started in Crossdressing in the net, Yvonnes Place, my own website, and more.

Most important, have fun, relax and go with it.

Answer 8

Try not to let morons like the collector bug you.
I'm not a crossdresser myself but a friend of mine is.
Just google crossdressing and you'll find plenty of information.
Good luck to you.

Answer 9

Just start from Bra under your regular cloth.
wear women jewellery that could be hidden
Armlet, 2 toe ring on each foot
anklet
I am sure u will enjoy that you till date could not enjoy the main thing.
Try to wear 2 Bra at once and enjoy the feelings
So I do

Answer 10

First of all, you have to find a good way to tuck your penis in. Second of all, that pesky adam's apple needs to be taken care of. Nothing a little bit of makeup can't take care of.