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You can accessorize his natural hair with hair clips, bows, and headbands to add a feminine touch to the outfit. Put ribbons or barrettes in his hair to look more feminine.

Put on a wig. If you want him to have longer hair, he can wear a wig. Choose a wig that is close to his hair color to make it look more natural.

Style the wig in any style you like. Wigs are a good way to create a total transformation in his look. Part 4 of Apply foundation and powder.

Find a foundation color that matches his skin tone and apply it evenly to his face. Apply a matching powder over the foundation to finish the base of the makeup.

Put eye makeup on him. Eye makeup will help accent his eyes and make them look bigger. Eye makeup is a great way to make a boy look more feminine.

Consider using two or three colors to blend onto his eyelid to make his eyes look bigger. Use eyeliner to draw a line at the base of the eyelid.

This will accent the eyes and give a finished look to the eye makeup. Finish with mascara on his eyelashes. Use black mascara if he has dark eyelashes and brown mascara if he has light eyelashes.

For a fun, festive look you can use colored mascara, like blue or purple, to make his eyelashes pop. Add blush to his cheeks.

Blush is a great addition to dress a boy like a girl because it makes the face look more feminine. Apply the blush to the apples of his cheeks and his cheekbones.

Finish with lipstick. The finishing touch to makeup is adding color to the lips. You can line his lips with lip liner and then fill in the rest with lipstick.

Part 5 of Encourage him to speak in a higher register. Tell him to practice speaking in a higher tone to make himself sound more feminine.

Record him speaking so he can hear what he sounds like. Have him practice walking in a feminine manner. A feminine walk will help make the look of dressing like a woman appear more natural.

His feet should pull him forward instead of storming ahead head first. Have him move his hips as he walks; let his hips lead his legs to engage his whole body as he walks.

Help him adopt female mannerisms. Become more sensitive to the interactions he has with other people to make the interactions more feminine.

Acting like a girl can often have as much mental impact as dressing like a girl in terms of how an individual is observed.

What happens if I go to a wig store and someone asks me why I'm getting the wig? That's probably not going to happen, but if it does, just tell them you're buying it for a costume and they probably won't bother you further.

Not Helpful 9 Helpful Marian Andersen. Bind your breasts with tight wrappings or wear a tight sports bra. Also you could wear a very loose-fitting top.

Not Helpful 20 Helpful You could always tuck it between your legs. There are tucking devices you can buy online or at specialty stores. Not Helpful 14 Helpful Luna Rose.

Looking like a boy involves many aspects. Wear your hair short, put on boyish clothes in dark colors, take daily multivitamins and sleep 8 - 10 hours per night to help you grow as tall as possible, and work out to build muscle.

If you can, get your doctor to prescribe puberty blockers so that your body won't become feminine.

As you get older, you can begin testosterone therapy to help you look like a man. Also work on your voice and your body language. Stand tall, walk confidently, and let yourself take up space.

Check out our gender expression articles for more advice. Is it better to wear dresses or pants if I'm trying to disguise a man as a woman?

It depends on the body type. Have them try on a few different outfits and see what looks best. When I was 12 my mom asked if I wanted boy under wear or girls panties.

I said boys underwear when I ment girls panties if I new then what I no now where would I be. Just found your site, lovely!

I look forward to many visits here. I too am a long time cross dresser, should have been born a girl, everyone told me growing up, I was a pretty boy with curly blonde hair.

If only…. Your Comments. Sometimes Boys Will be Girls! Boys are told to be tough and be a man, but that is bull in my opinion!

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