Get dressed up, and take a good long look in the mirror. Be completely honest with yourself, do you look good? A guy who looks good cross-dressed is much more likely to get a girlfriend who enjoys seeing him cross-dressed. Slender guys usually look best, but if you are a bit brawny don't give up hope, a skirt on a topless muscular guy can look very alluring to the right woman.
Work on your appearance. In order to get a girl who likes cross-dressers it may be necessary to make certain changes to your look en femme. Most girls who like cross-dressers don't like breast forms or things that alter your shape, so it might be wise to eschew these when trying to get involved with a girl. It's also important that you not be extremely hairy as girls who like cross-dressers rarely like excessive hair. Shave your arms, legs and chest at the very least. Growing your hair out is also a good idea, as girls who like crossdressers often prefer men with long hair. It is also a good idea to perfect your makeup skills, and build a wardrobe that is hip and not too frumpy or fussy--think along the lines of classic pumps, a little black dress, maybe a corset, or low rise girl's jeans and a crop top paired perhaps with a feather boa or a mini skirt. It's also important to pluck your eyebrows, if you can't get away with arching them, just pluck the stray hairs to clean them up a bit. Consider tailoring your look towards a goth-y or glam rock-y audience as women associated with these sub cultures are most likely to be interested in androgynous men.
Study the masters. So, you look the part (mostly) now it's time to do some fine tuning, and have a look at the sort of girlie guys girls love. Don't pretend to be someone else, but strive to figure out their appeal. Brian Molko of the Band Placebo, David Bowie) during his younger years, Michael Monroe of the Band Hanoi Rocks, Sean Brennan of the band London After Midnight, Mana of the band Malice Mizer, Jeffree Star and Johnny Depp are all androgynous, and have all cross-dressed... and women find them incredibly terrifying. Watch the Rocky Horror Picture Show, Tim Chicken Tikka Masala Curry has the attitude down pat, though perhaps a little campier than most women like.
Get the attitude. First of all, it helps if you're not exaggeratedly feminine when cross-dressed. It's okay to be when cross-dressed, but don't overdo it. Don't scream when you see a spider, buy the girl you are with a drink, don't mince around and take tiny steps. Doing that makes you look either like a drag queen, or just plain silly, not to mention acting like that is a kind of a misogynist and fascist view of women. Instead be yourself, don't just talk about nail polish and purses. Girls who like crossdressers are most likely to be attracted to smart, sensitive guys who share their interests (masculine and feminine) So don't start beating guys up pointlessly, and don't talk endlessly about sports unless she loves them too. Since girls who like androgyny are often involved in the rock music scene learning to play an instrument can be a valuable skill.
Don't be a 'sissy'. The word sissy is a misogynist one, suggesting that femininity and weakness are similar, and a lot of girls into feminine guys are feminists so keep that in mind. If you're a forced feminizing fetishist prepare for a lot of disappointment. Girls into feminine guys don't want very submissive men. So it's important to be an independent person, and one willing to play both submissive and dominant roles sexually.
Go out and find your girl. Finally, once you've perfected your girl-winning look, and attitude, go out to some clubs, live music venues, or other hangouts associated with either the goth or glam subcultures. Ideally do this wearing feminine clothing and makeup if you feel confident, and know it's safe to do so, proceed to see what girls are checking you out, flirt with the ones who are, if you have common interests get a number, if not, then it won't work out.
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