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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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3y ago

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