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I'm hoping this is with a willing participant (even if he claims to be reluctant). If you haven't gotten here yet, start with that.

First of all, you should both agree on what you're hoping for at the end of the process. Does he want to look like a boy in a dress for a lark for some party? Is he wearing a costume? Does he just want to look as much like a girl as possible? Will he be out in public or just there with you?

Figure out appropriate clothing, and where you can get it. Hopefully you're similar sizes, or at least you have some items that are loose enough to work. Otherwise you need to go shopping. Get a wig if his hair is short. Don't go too outlandish with the clothing unless that's your goal. Avoid sky-high heels unless you want him to fall down and break his neck. Think about what you're planning for makeup, and whether he'll need anything of his own (sharing eye makeup is gross). If you're going for a realistic work, might need some level of shapewear.

Then have him sit still and let you work your magic.

My first time as a girl, my friend picked out an above-the-knee A-line skirt, blouse, and sweater, with tights (I didn't have a ton of leg hair, but I wasn't ready to shave) and some low wedge shoes. I was close enough size wise to wear her things.. I started by putting on my girls undies, some spanx for shape, my bra, and a robe. She started with my nails, then did some light makeup (foundation, blush, mascara, lipgloss). My hair was long enough for some teasing and a floral headband to make it look girly. Then into "my" skirt for the rest of the afternoon. We both really enjoyed it.

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Lvl 5
2y ago
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not

Lvl 5
2y ago

You're a good friend for helping. First, pick out something for him to wear that will be flattering on his body - nothing too over the top, and nothing too fitted or uncomfortable. A knee-length a-line plaid skirt, blouse, and sweater would be nice, or a casual knee-length dress. He'll likely need to borrow a lightly stuffed bra, and possibly some kind of shapewear to help with curves. If he's not shaving his legs, go with opaque solid-color tights, probably white. Go with shoes with a low heel - something he won't be tripping over. Help him do his nails to match his skirt - it will help him feel girly. Don't go overboard on the makeup - foundation, a little blush, some lipstick, maybe some eye shadow. No over-the-top colors. If his hair isn't long enough to style, help him with a wig and help him brush it out and style it. Add a headband or a hair ribbon for a little girly touch. Clip on earrings if you have them and a simple necklace or bracelet.

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Wiki User

12y ago

The question arises, how did you wants to crossdress? If you are interested in complete girly look, then you should probably seek for you leg wax, a mini size skirt, bra - ofcourse some tissue paper to grow your breast and something girly dress. Then, you should try a heel , some makeup and pony tail if you are having a long hair. The best thing to do this is to take help from a girl friend.

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15y ago

The same way you "adult" cross-dress! If you want to dress like the opposite sex, go right ahead and experiment. It helps if you watch others who were born that sex, and see how boys and girls act, talk, walk, and move. If you use Google.com or dogpile.com, you can find lots of websites with specific information about which way you want to go (male-to-female or female-to-male).

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7y ago

trick him or tell him a bet wich you know he will lose like dress as a girl for a week and if he doesent pass for half a month tell him it's fashion (easier when going to a foreign country)/trap him and then pull a dress over his head (and make sure to take a picture before he pulls it off)/first answer

Or, you could just ask him. You'd be surprised how many boys would willingly participate with just a it of convincing.

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15y ago

one thing have you done this be for ???? if not then do the following frist is the under clothes bra knickers and then tights now comes the skirt then the top jumper or what you like heels now you may need to go to a shop that will do shoes for women with larger feet to finish may be makeup and a wig all the best

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13y ago

Well, you would make them wear "girly" outfits, such as dresses and put their hair up, if its long enough. If they don't like I don't recommend force.

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8y ago

you can find some makeup artist. Get a wig and hide all beard hair with makeup.

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14y ago

in a locked bedroom or bathroom, with no one else home. but getting clothing is another matter.

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12y ago

Just put a dress on him.

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Q: How do you make a boy dress as a girl?
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