How to Find a Girl Who Likes Crossdressers (for Young Men)

Reviewed by John Keegan

Last Updated: December 13, 2024 Approved

So you're a young male cross-dresser, and you find you'd like a girl who not only accepts your cross-dressing, but gets pleasure out of it, too? This guide is largely written for guys in urban areas, but some of it will work for rural guys too.

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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.
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.

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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.
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.
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.
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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I’m a girl who is attracted to crossdressing men. Does this mean there’s something wrong with me?

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This answer was written by one of our trained team of researchers who validated it for accuracy and comprehensiveness.

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Not at all! Everyone finds different things attractive. There’s nothing wrong with being into men dressing a particular way or bending the “rules” of how gender is usually expressed in your culture.

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Do girls like guys who crossdress?

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Every woman has her individual opinions and preferences, so there’s no universal answer to this question. However, there are definitely many women out there who like it when guys crossdress.

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Where can I find someone who can help me learn how to crossdress and be more feminine?

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One great way to start is by checking for tutorials online. There are tons of blogs, websites, and YouTube tutorials by experienced crossdressers out there. If you want to meet someone in person who can help you, try checking Meetup or a similar website for a drag group in your area. You can also try talking to a close female friend and getting advice about styling your clothes and makeup.

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Gay Bars on the transgender night, though a fun group of people, is not a good place one to find younger, hip women interested in cross dressers.

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Some women like crossdressers with prominent Adam's apple. Experiment a little to find out what look you like.

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Be a gentleman or a lady, which ever suits you. Think about complaints women always have about men and try to take that into consideration. Don't stare at her breasts, be polite, be interested.

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Bringing a friend is a good idea as there's safety in numbers.

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Some people may give you problems about wearing women's clothing, if you can take them, great, say something back, if you can't/aren't sure, stay quiet and walk off.

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Men may hit on you, if you're not comfortable with this then be polite and say "No thank you." like the classy lady you are!

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Don't be creepy.

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