I get a lot of very kind emails and comments full of appreciation that I speak positively about men who wear womens clothes. Many of them “wish there were more women who love cross dressers”. And a lot of them say how hard it is to find such women. So there’s obviously something of a shortage of such women. I have touched on this in other articles and here I want to take it further and try to help those of you, who are searching but not finding.
Much of what comes now is not rigorous research or analysis on social studies but mostly opinions that I came to from my own life story and my encounters with the people in my life. I know, that might not help you terribly well, since I’m not exactly a ‘normal’ woman. But I’m not a total nut job either. What gave me the attraction to cross dressing men was not a freak incident or a birth defect that only few women have. It was a series of experiences and I’m sure that many other women, surely the majority, would arrive at a similar place if they had made the same experiences. From my point of view, I can’t see how one can not appreciate men willing to wear womens clothes. But that view is where I am AFTER undergoing the process that led me here. Before that, I was just as ignorant and dismissive as everybody else.
How is that supposed to help you?
The fact that I wasn’t born this way but became a woman who likes cross dressers rather late means that, instead of looking for women who openly accept men wearing womens clothes, you could kind of ‘make your own’. As with everything involving people, it won’t always work but I am sure that, given enough chances, most men could make this happen. I also believe it’s probably more successful than going out looking to date women who already say they like men wearing womens clothes.
I have had a reader tell me he finds it best to go out openly from the start, so perhaps I’m wrong. But I obviously can’t comment on his experiences. I can say, however, that many ‘normal’ women would reject a man who wears womens clothes openly from the start. I probably would have, if I’d met one when I was 18. But, because of what happened with me, I think many of those same women who dismiss and reject cross dressers, might very well learn to love them if they had the same things happen to them.
How to help your partner to like you wearing womens clothes
The most important thing here is how you tell her that you cross dress. If you haven’t yet, then I suggest that you read that article now. In my case, that turned out to be crucial and I am certain this will be the same for most women. I’ve heard many stories about men who keep their lifestyle a secret for many years and then get caught. That, for example, is not the way to go about it.
But that isn’t enough. Another important part of the story is that I was completely in love and my boyfriend could have told ma a whole load of things and I wouldn’t have minded. Maybe my attraction to cross dressing men was down to my associating it with someone I love. That could very well be and then it could also work for many others.
The problem is, you don’t just want her to put up with you and tolerate you wearing womens clothes. You want her to appreciate it and perhaps even love it as much as you do. I won’t lie to you. This is much harder. It’s always a tough thing to try to make somebody like something but it’s not impossible. Again, I’ll try to describe how I started liking it and maybe it works similarly for others. Read my article on why I love cross dressers to get an idea. In short, it’s down to him trusting me with such a secret, the fact that I’m attracted to vulnerability in men and the fact that he has a gorgeous body that looks stunning in anything that reveals or flatters his shape. Those three things are what drive me nuts about it and any one of them would have been enough to make me like it.
It’s not just about clothes but also about taste
The fact that men wearing womens clothes is an issue to many people, is mostly down to ignorance and intolerance. We all know that but there’s another side to it that I rarely see mentioned by anyone and that is taste. If you wear something that doesn’t suit you at all then you’re not going to win people’s appreciation. That has little to do with gender. You see, not all women get away with wearing all the clothes they want either. For a laugh, I put on my boyfriends casual wear and it looked absolutely hideous on me even though it was ok on him. Or as another example, try to imagine a very overweight woman with hairy legs, be honest with yourself about how you’d think of her wearing sexy lingerie. And the reality is that most men don’t look after their bodies like women do and so there are a lot more men who aren’t suited to that kind of fashion. It’s not because they can’t become suited or because the male body isn’t suited for it per se, but simply because they didn’t prepare enough.
As far as I’m concerned, I even love those men wearing womens clothes whom it doesn’t suit in the least because it has something endearing and helpless about it. But this is the part where I’m the weird one and you shouldn’t count on meeting many others with such a preference. Then again, I don’t really know that - just a guess based on my observation of the people I meet. The bottom line about this “taste thing” is that, something like sheer tights or suspenders look amazingly hot on the right legs - that is every bit as true for lean muscular mens legs as it is for lean womens legs (far more so in my opinion) and I’m sure most women would agree with me.
Please share your experiences or grievances in the comments.
steven on May 09, 2019:
my women likes me in leather she likes me in my black leather motor bike leather jeans also brought me a women red pvc pants and womens black leather jeans
Alan Oakley on November 14, 2018:
Thank you so much for this artichle. As a man I would love a woman to indulge my feminine side, and I think it could really build intimacy and true sharing when it is realized that here is a man who also comes with the ability and interest to really know and learn how to treat a lady. Shopping trips, shared emoting, real friendship built on trust, are all possible with this type of man. Men in the west are reared to not show feelings, to be ice except when in the bedroom. It is changing, but to slow. Men are in need of reshaping, even if it is temporarily play. We need to meet women on their level, and learn them in order to do that..
Alan Oakley on September 05, 2017:
I love my feminine side, but have never found a lady who would be interested. I have looked, but I think mosr women want a masculine man, and not a feminine one....
mattyhose on June 28, 2017:
I just want to say I love wearing pantyhose and heels, dresses, bras, panties, make up. I'm straight male just like dressing up and would like to find a girl that likes it
Stephanie on April 29, 2016:
From the age of 5 I picked out of my mother's bedroom furniture one of her bras. I do not know why I did this but I took to my bedroom and put her bra on. I must of felt in love with what I needed. As time has passed and growing up as a teenager, wearing a bra under my clothes, helped me feel comfortable. After getting married at 19 years of age, I hoped this would bra wearing would go away..... From time to time it did. But she saw me in her bra and on Halloween I got to wear one of her real nice bras she said will work for my sexy maid outfit, it was heaven......As time passes and drives in my car with a female breasts under my shirt. That I loved to do when ever I could. Years later on with a new wife I now have the same thing going with me and its this female wanting out. One day I hinted that I have a bra, and she said put it on. I was so happy, oh maybe she will help me with this female desire. After a few months she encountered me to wear it takes to be this right brain loving feminine woman. And so now I dress as Stephanie, life is so much better for our marriage.
Kathleen D. on March 08, 2016:
I live in the conservative Davenport,Ia. area and I've never had a problem getting a boyfriend that will wear panties for me. If he will wear a bra for me then I know he is really into me. I would not want a guy to wear anything outwardly girly, but I love it when he wears something special for me under his guy clothes. I like to get a guy to take me on a trip where he will wear panties for me all the time and sometimes other things like a padded bra or pantyhose. It's our romantic secret. Every guy that I have dated for very long has always done this for me. You would be amazed what a guy will do for you if you just ask seductively.
Kathleen D. on February 21, 2016:
I posted earlier and now I have new boyfriend. I love being in control of what the guy wears under his guy clothes. I would not want a guy that was a crossdresser on the outside because I want him to look manly, but I love getting a guy to wear special things for me. If he will wear a bra for me, then I know he is really into me. I live in conservative Davenport,Ia., but I always manage to get a guy to wear things underneath. I have convinced a boyfriend to wear corsets, stockings, girdles, pantyhose, panties, even a longline bra with large breast forms under a bulky winter coat show it wouldn't show. The ultimate fun is doing this so he is a bit on edge when we are out. He will always be very attentive to me if he's wearing special things underneath that keep reminding him of me. I have never had a boyfriend refuse to wear something special like panties for me.
Tulip69 on February 06, 2015:
hi im very embarasing about this, dont know how ro start :-( x thanks lucy
Doug on July 04, 2013:
I am happily married to a woman who accepts, but does not embrace, the feminine parts of my personality. However, I think that if I were single and looking for a relationship, I would start off en femme rather than in male mode. I would seek out opportunities to meet and form friendships with women in low-stakes, non-threatening situations, such as continuing education classes, arts groups, etc. or even at the nail salon. I would then introduce them to my male self if we hit it off. That way there would be no surprises a about cross dressing and I would know from the outset that she doesn't mind hanging out with a guy who is comfortable with his femininity.
I find that generally, women are very friendly to me when I am dressed femininely. I think there are a lot of women who appreciate a guy who understands things from their perspective. After all, I have walked quite a few miles in their shoes (and pantyhose, makeup, etc.)!
maid sissy slave on April 24, 2013:
Ihave been to pro doms in the past. But now Im looking for a classy lady who needs a sissy maid maybe someone could help me on this site
toni on March 27, 2013:
i am a man i like to dress up it makes me fill great
K on January 15, 2013:
Thanks. I am a man but inside me there is also a woman. I sleep in womens underwear and nightgown. I shave most of my body hair but leave my lower legs alone and some in my pubic area. I love to feel feminine. But I am also a very capable man. My wife does not like my feminine side so I keep it somewhat restrained for her sake. I wish she was more like y0u in this regard.
Josephine on November 16, 2012:
I am a man that just love wear women's clothes a lot my favorite color is Pink, and Purple only.
Lucy83 (author) on October 23, 2012:
Wow Psy Mode.
That's one hell of a moving comment.
Psy Mode on October 18, 2012:
I'm finding it hard to write how much your articles and website are meaning to me. I have only relatively recently begun to accept my feminine side and need to express it (albeit in private). I have spent my whole life denying it due to a very strict Catholic upbringing. The enormous feelings of shame and fear can be so overwhelming you just can't imagine. So I'll try to express how much your words mean by saying this: Thank you so much for showing me that there are others like you. Thank you for showing me and others that the myths that often come with cross dressing are ALL WRONG. Thank you for showing me and others that it is mainly a heterosexual thing. Thank you for showing me that some women get turned on by men expressing their vulnerable side like most women do and take for granted. Thank you for showing me that I'm not a freak! Thank you for showing me that I should not be ashamed of the need to express my feminine side. And thank you for helping a 40 year old come to terms with who he really is. *tear falls*
B.A. on October 04, 2012:
IVE crossdressed since I was 9. what did it for me though was when I tried on my very first bra. It was white and that did it for me.I love women so much so that I dress like one at home.Nothin fancy with me. At home I wear black spandex and boots and my bra and my big big boobs and a shirt.In fact im wearing it now and I feel like myself. Besides why is it women can wear pants and shirts and us men who wear the dont complain but yet if we men wear somethin of thiers then its like so taboo? Sounds to me thats a double standard.At least im not out cheating.I love my life at home as a women.And yes I love women not men.But I feel like such a slut. But it sure is fun though.
Lucy83 (author) on June 12, 2012:
you'll never know until you attempt it. Hope you find what you're looking for.
Ellen on June 06, 2012:
I have been crossdressing fully for about 16 months. I have not made any attempts to date any women because of the feeling they would not understand what crossdressing is all about. Hopefully I can meet someone who will.
Paul Duane from Salt Lake City, Utah on April 22, 2012:
I'm of the opinion that you make your cross dressing such a common part of your life, that anyone that gets to know you very well will find out about it very quickly. Discuss it in a very matter-of-fact way with anyone who asks. I've been very fortunate to date several women who loved my alternate fashion sense. You can see a few photos of how I make it work here: http://www.paulduane.net/blog/fetish It's definitely doable. The first item of business is to become totally comfortable with yourself. You can never expect anyone to be more comfortable with you, than YOU are.
mark on March 26, 2012:
there are a lot of women that i have sen in my life thatdont mind and even like the fact that i like to where womens cloths from my exsperence and i know i could not stop feeling the way i do like when i am dressed up in sexy lingerie my fav thing to do it seems like is to go shopping in the womens section at the store and the sexier the better i ant afread to bye the lingerie but i would never where them in public and i would never tell anyone othertan my lover and she exsepts the fact that i cant help the way i feel and soe times she even picks out what i will where .
michele samina on January 10, 2012:
I've found openness and patience to be the key towards understanding and acceptance. You have to be considerate of your partner's feelings and know when to bring up the subject. I don't subscribe to the rigid framework that is forced upon us by our ignorant society, but at the same time, I have to find a balance to keep the peace. I find it liberating to be able to express myself as a person, not a construct, much the same way women have already done. I wish for the enlightened day when the "double standard" would be referred back to as a time of intolerance.
Lucy83 (author) on December 28, 2011:
you know there is an interesting point. It seems like those women are hostile out of jealousy or a feeling of inadequacy. I've heard of such responses several times. Perhaps they feel if men are more beautiful than they are then they have nothing going for them. Perhaps those are the kind of women who rely entirely on their feminine looks to get male attention. For such people, the thought of men becoming as beautiful or even more beautiful (in a feminine way) will be very scary.
My advice to them is: grow up. There's more to being valuable than just being physically attractive. And it's a myth that men only value beauty in women. Besides, if beauty is all you offer, then don't complain if you get treated like a mindless accessory.
It's also very cynical to deny men the right to emancipate their gender role while enjoying the freedom to do traditionally masculine things for your self. After all, it was men who created women's liberation. Might not be a comforting thing to admit but that doesn't make it less true.
BereniceTeh90 on December 23, 2011:
I think part of the reason many women are so hostile towards the cross-dressing community is because many of them (no offense) really do end up looking like the over-sexualized contemporary ideal of "femininity" (ala Jessica Rabbit) which seems to dominate our media.While I do not object to these men wearing what they love, I just assume that's one of the reasons explaining women's hostility towards the cross dressing community in general. (Nobody quote me on this okay, this stems from pure anecdote)
On the other hand, you have crossdressers like Andrej Pejic, David Bowie, etc who are really quite attractive from a hetero-female point of view. Nevertheless, you will encounter hostile women towards these guys. I was shocked to find many hate-filled, homophobic comments on the forums concerning Pejic, and to my surprise, most (if not all) of these comments were left by women!
One woman summarized her feelings by saying that,
"I won't deny it. ANdrej is beautiful, but nevertheless, he is still a fake. And his donning of female attire does nothing to make real women feel good about themselves, in attaining that impossible body ideal".
Another was a tad bit more spiteful, saying
"You see? I knew that most fashion designers are gay men; they design women's clothes in order to fit the male body, not the voluptuous curvy figure!"
threesweds on December 16, 2011:
Lucy I understand. Not only do I enjoy wearing lingerie, but I also like to look at women and guess what lingerie they may be wearing. Sometimes the vpl or outline of the bra through her clothing or even a peek of the panties or bra showing can be quite a clue to the mystery. If I met you, you would have no problem knowing I wear women's lingerie, because I also like to "show off" my panties. My girlfriend thinks I'm crazy, but I enjoy the comments from women.
Lucy83 (author) on December 14, 2011:
Well I can't be sure of course until I ask them straight out (which I have done). When you have a passion for certain things you start noticing them everywhere when other people wouldn't see anything. No idea if that makes sense now.
threesweds on December 13, 2011:
Lucy, you must have a good eye for spotting men in women's underwear. What gives it away? I love your insight and open mind about men wearing lingerie.
Lucy83 (author) on December 13, 2011:
Actually I haven't met that many crossdressers personally. Only when we go to some party really or when I spot them in public (I can often tell even those who just wear women's underwear) and of course countless online.
Sometimes other things come up but I haven't come across much age play.
Kevin on December 11, 2011:
I'm guessing you've met a few crossdressing males. Have you found many who share other kinks as well? I've met quite a few who are into age play, which I also happen to enjoy.
Lucy83 (author) on November 22, 2011:
sorry I had to deny your comment because it had links that you can't see unless you sign up for something and I think that's just a little too spammy for most people.
But please repost your comment without the links (or with usable links).
To answer your question, being a little bi myself I can only say I prefer feminine looking men but as far as the physique is concerned, I like the slightly muscular - or athletic type of male body best. Body hair I prefer there to be less and ideally none. As far as height is concerned I'm a lot more open than I used to be. I think most women will want a man who's at least their height though. I'm a little more eccentric there.
Lucy83 (author) on November 12, 2011:
I'm sorry you had those experiences. That just goes to show that most people are idiots - male or female. I know I should say "well such people aren't worth your attention anyway" but it still hurts on some level no matter how tough you are. Perhaps you're attracting the wrong kind of woman or perhaps you're hanging out in the wrong places. Just an idea.
As for your question, I personally have some more or less strong bi inclinations. I'm sure that has something to do with my attraction to crossdressing men though I have to say I don't feel that way. I mean, I'm not more attracted because he's more like a woman but because he has the openness and sensitivity to share that side with me. I only rarely dress him up completely because he's not into that so much. It's more the occasional thing.
And I just love the male anatomy so much and dressed in soft feminine fabrics is like the perfect eye candy. So I guess I prefer to be able to see that he's a man underneath the clothes.
Sure I envy him but that's complicated because I also envy him for his masculine body. It's just so much more aesthetic and beautiful but he says he envies me for my body and some other reasons.
AnotherGuy7 on November 09, 2011:
Obviously as someone who has been crossdressing on and off for 14 years (started when I was 12), I appreciate that you are a girl who is so vocal in support of understanding and accepting those of us who enjoy femininity in addition to our masculinity. When I was younger, I would dress for a while and then stop for a period of time. Fortunately, a few years ago I finally accepted that my crossdressing side is a part of me as a whole person.
As a result, I have been more open about my feminine side within my relationships. And while I fully understand if a woman does not accept it in a relationship, the three girls I have told in the last 5 years (each was 1-1.5 years long), I have had the response that we all fear. Ive been torn down verbally, called every stereotype in the book, and had friendships threatened over coming forward in my relationships. All that has certainly made it more scary for me to do it again, but hearing from girls like you helps make it all that much easier to do it again, so thank you.
Ok I'm writing a novel and I apologize, but I also had question, that as a girl who had enjoyed dating a man who wears women's clothing, I figure you have unique perspective for. Does the degree of dressing effect your potential attraction level? Meaning, I am masculine most of the time, but when I am feeling feminine, I like to go all out with wig, make up and fake nails. In your experience, do you think that the extent of dressing when feeling feminine ("going all out"), effects the ability of a girl to accept the guy, or at least be open to trying? I know I am straight, but I can certainly understand how a girlfriend hearing that her boyfriend could be more feminine then she, could have trouble reconciling that fact.
Ok, done rambeling, thank you for listening and I hope to have the chance to hear more from you!
Lucy83 (author) on October 22, 2011:
Sorry you had that experience Marc but please don't think that all of us are like that.
Marc on October 19, 2011:
Never trust a woman who say she likes to see her man wearing skirts, high heels and so on. I was married with such a woman. She baught me skirts, panty hose, nylons, string bodies... One day she trough me away with the argument that I'm a pervers man.
Isisgreen on August 14, 2011:
Hi Lucy83 I just want say that the word gay dose not have any thing to do with same sex relationship it is a 1920 term for a state of mind or state of being (Happy) the word that must people are looking for is Home sexual all thought a lot of home sexual are happy for the most part
but to point i like to dress in woman/feminine item my self in fact i,am taken a hypnotic program to become more womanly and think like a woman hopefully to became the woman i would like to be
Sherman on June 16, 2011:
Before marriage we're all on 'good behavior' trying to make the best impression on someone we really like, but also we overlook important parts of ourselves which we fear may turn to other person away. Unfortunately I learned years into marriage how important cross dressing in underwear is to me. However, I still sense my wife would not understand. More importantly I'm certain she would not invest in understanding. I should have recognized and admitted this before marriage. Now I live with it. I regret not being 'up front' about this and letting the chips fall where they may.
Lucy83 (author) on May 26, 2011:
thanks for your nice comment. One question: Why did you marry your second wife if she was so closed minded that you knew she wouldn't tolerate crossdressing? I just can't understand that.
Either way, I'm happy you found someone worthy to share your life with.
torty from Knoxville, TN. on May 25, 2011:
First of all I wanted to say thank you for raising awareness about the fact that there are indeed completely heterosexual men in the world that enjoy wearing womens clothes, and secondly that society should not get freaked out over a man wearing womens clothes. I first tried wearing womens clothes when I was 12 years old and discovered that I really liked the way that I felt when I was wearing them. I knew that my family would not accept or tolerate me wearing womens clothes so I kept it a secret. My first wife actually caught me wearing her lingerie one day and to my surprise she did not freak out. I began to wonder if men wearing womens clothes might one day be widely accepted. Things did not work out with me and my first wife and my second wife was a very close minded person that I knew would not approve or tolerate my cross dressing. I eventually found a woman that is amazing and she actually likes the fact that I wear womens clothes. I really got lucky with this one. Just bringing up the subject of me liking wearing womens clothes happened by pure luck. I had spent the night with her and forgotten that I had ran out of clean underwear at her condo, so I was going commando. We were out and about most of the day and since it was winter I was complaining that it was way too cold to be going commando. She said she would fix that. She drove us back to her place and picked out the girliest panties that she had and put them on me. Ever since that day I have opened up to her and I think that it brought us closer as a couple. She even paints my toenails for me. I don't really go overboard with wearing womens clothes in public. I have the type of job that is considered to be a dangerous job performed mainly by manly men, and there still is a side to me that is very much all man. Sometimes I like to put all of that behind me and enjoy feeling sexy and femenine.
Kathleen D. on May 13, 2011:
I have dated several guys who would wear panties for me. It all started out playfully with a guy I was dating years ago. I've always approached the subject gradually and playfully. If they won't at least wear panties for me then I don't date them for long.
My current boyfriend knows that I like to see him in panties, so he always wears them on dates, but not all the time. For special occassions I get him to wear a bra, panties, and sometimes pantyhose under his male clothes. (A jacket covers the bra). Nothing shows on the outside, so it's our romantic secret.
I got him to take me on a trip to the Dominican Republic where he wore panties every day. It was awesome!
We are both 100% heterosexual, but I love the idea of knowing that he is doing something special for me under his guy clothes. He will shop with me and I buy him things that I want him to wear. He does not behave girly at all, and I love to see him wearing these things.
Gr8legs on May 03, 2011:
There are two points in this article with which I would particularly concur:
"If you wear something that doesn’t suit you at all then you’re not going to win people’s appreciation."
I mainly wear skirts and tights as daywear, albeit in an otherwise masculine fashion with masculine boots & men's shirts and - curious looks aside - rarely have I experienced any openly negative reactions. In fact this has happened only twice that I can recall during the past year and on both occasions these were cat calls from a distance from young (& insecure) lads who didn't have the bottle to openly confront me about my dressing preferences.
I now exclusively wear lingerie (panties, tights, half-slips) in place of 'male' underwear and openly change into these in the gym locker room irrespective of the outerwear I am wearing. The regulars know me and accept it and will converse casually with me whilst I am dressing as if it were the most normal thing in the world for a man in the locker room to be donning women's clothing and underwear.
A good deal of the manner in which people respond to you is dictated by the way in which you present yourself, as well as your demeanour. If you go about your business with a confident air, then people's reactions to you will reflect this; if, however, you shrink away from them, or have a 'victim's air' then they will respond accordingly and you are more likely to be on the receiving end of disparaging remarks or abuse.
"...something like sheer tights or suspenders look amazingly hot on the right legs - that is every bit as true for lean muscular mens legs as it is for lean womens legs (far more so in my opinion) and I’m sure most women would agree with me."
I have gone out on the town on a number of occasions with my girlfriend (who luuurves me in silky, sexy lingerie and particularly stockings & suspenders) in the evening whilst wearing high-heeled boots and shoes with fashion legwear and skirts ranging from knee-length to mid-thigh and have received a number of very positive comments from women on my 'look'. Many have commented that they wished they had legs like mine, some that my legs look better in short skirt & tights than many - if not most - women's legs, or else just a plain "Nice legs". I have also had women comment that more men should dress in this manner, with the proviso that it should only be if they have the legs (and physique) to carry it off. The same could also be said of women, that they should only wear short skirts of they have the legs and figure to carry it off.
threesweds on April 12, 2011:
I love your hubs. My girlfriend sounds a bit like you. It wasn't the fact that I wear womens lingerie that she fell in love with me, but rather she fell in love with me for who I was. We have had a great relationship. She desires the sensitive, openness of our relation, while I enjoy her dominance in the relationship. We have had many enjoyable shopping trips for lingerie ending in romantic embraces. I haven't tried wearing other womens clothing, but would love to try on dresses in a womens clothing store. I hope I'm not pushing things too far.