Updated date:

Why Women Leave Men Who Wear Women's Clothing (Part One)

Do you think 99% of women would leave James Bond because he occasionally wears a bra? Methinks not...

Do you think 99% of women would leave James Bond because he occasionally wears a bra? Methinks not...

This is a tough issue, but I think that it is one that needs to be addressed. It has become obvious that many men who wear women's clothing, both those who wear panties, and those who take their female fashions much further have difficulty sustaining romantic relationships with women. Some men even report losing several partners because of the lingerie, or because of the skirts and high heels.

This article will look at the question why. It's easy to simply say that most women are evil and bigoted and leave it at that, but I don't believe that is true. I think that most women, once they fall for a man, will do most anything to please him, in much the same way a man in love will try his best to keep his special lady happy.

As with anything involving human beings, the issue is complicated, but I have several theories concerning why men who wear women's clothing may find difficulty in maintaining a relationship, and in discussing these theories I hope to also provide some possible solutions.

Problem One | The Hardline Woman Who Refuses To Brook The Mere Mention Of Men In Panties

Women with hardline views religiously or culturally may also have a very hard time dealing with a man who wears women's clothing. To be honest, I think without being too harsh, women who possess hardline views are normally best suited to men who share the same hardline views and values. If a person, male or female, is unable to compromise on arbitrary conditions, then they require either a partner who shares the same value system, or one who is prepared to nod and smile and agree.

Unfortunately, I have a feeling, a hunch, if you will, that men who wear women's clothing for the joy of being feminine and soft and passive, perhaps even submissive are attracted to these hardline women because it is easy to mistake inflexibility for strength. A woman who vociferously and aggressively defends her views may trigger certain responses in a man who enjoys his own feminine side.

So, the man who wears lingerie finds himself dating a string of strong, though inflexible women who, far from indulging his desire for lingerie, simply forbid it, expecting to get their way as they always do.

The Solution

Wean yourself off this type of woman the same way women learn to wean themselves off the 'Bad Boy' type. Yes, domineering women can be sexy, but unless you find one who likes her men to wear lingerie (and there are severe supply and demand issues with that little scenario) you're going to be opening yourself to ongoing heartbreak and guilt as these women reject you and your desires out of hand.

Problem Two | Identity Issues

The likelihood of this problem arising depends on the extent of your dressing in women's clothing. Some men like to wear panties and draw the line there. Some men like to dress up entirely in women's clothing and adopt female personas. Obviously these behaviors sit at obvious ends of the spectrum, and men whose desires tend towards just wanting to have a few pairs of panties about the house are going to have an easier time with their mates than men who want their wives to call them “Susie Snookiepants.”

You have to be honest with yourself, are you the same person on the inside that you portray to your partner on the outside? If your spouse or girlfriend becomes confused about who you are, or worse, suspects that you are simply transitioning to a different gender, she will feel hurt and betrayed. Women want, above all, to understand and to empathize. If you make that impossible, she will not be happy.


If you have an alter ego, introduce your partner to this alter ego at the appropriate time. (The appropriate time being that magical spell in a relationship where you are past simply dating one another, are becoming increasingly intimate and the birds are singing in the trees and under every daisy is a little pot of gold.) Chemically speaking, you're both quite mad at this time, and this is the time where you set expectations and boundaries in your relationship. If you go through this time without letting her see your secret facets, don't be surprised if she freaks out later on.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.


Dewey on September 09, 2020:

I've been wearing panties from 10 years old I've been with older lady 4 before age 18 I've found they come to me when alone its the best time for them to tell me the want of me to put on silk pink panties that they have a fantasy of suckling a hard cock in silk pink panties now I'm putting on the sexyest pink panties add verry hard

Karrl Schroder on August 06, 2020:

The problem I know myself is the false idea that feeling human beautiful one automatically assumes it's female. Big mistake.

Rick on March 19, 2020:

Maybe women leave men because there men look better then they do and are jelous. So men keep on dressing like you want and if your woman dosent like it t.s. find one who dosent care hopefoly the same size.

Tim on March 03, 2020:

Some women may not like there men wear womens cloths because the to too good

Dennis Andersen on February 20, 2020:

The reason why women leave men who wear women's clothes is that women think he is gay because he is wearing panties she thinks he is trying to atrach men witch he is not its because he feels the power of femininity throu wearing panties, witch is the first step to cross dressing and the other reason is that she dont what him to look better then her in women's clothes

Joanie on October 20, 2019:

I have been dumped by countless women who just don't understand ir care to learn why someone may like wearing women"s clothes. They are miopoc and probably feel competition. Just becaue a man likes to wear women's clothes doesn't mean he's is gay ir going to have a sex change

The other thing that sucks which I just experienced is that women will use this lever to justify infidelity and breaking up.

What's the big deal? They are j

Althea on June 29, 2019:

I'm married for 31 years from day one I told my wife that I like to dress as a woman, also wearing silicon breast. She did not care and approved it, ( if you feel good and happy in that way just do it ) that she said to me.

I still wearing woman cloths also she show me how to use make up, at this point I use lipstick and I do nail polishing in my toes only.

I was told many times from different persons that I have womanish feet. I go out and use very frequently skirt any length and style when the weather permit I shave my legs from I was 17. Also, I use exclusively woman sandal, they fit very well in my feet. I had some bad look from man, also I had many complements from woman and few from men. I had a case where a guy telling me that doing nail polishing is a female business, my answer was very simple, its my own tattoo and the best, I can erase it any time, meanwhile tattoo don’t ! He could not say anything, end of story. I do mix female and man clothing also never dress as a woman before or during sex whit my wife, I like that she feels that a man is doing the job, I guess. So I fell lucky that at home my wife and my kids ( 26 & 30 ) don’t care at all my way to dress.

Have a nice day and don’t fell shame be your self.

S212 on April 26, 2019:

I’ve secretly worn lingerie for a long time mostly just panties since I was little. I’m a straight male it is hard to find women to be into this that’s why I’ve kept it hidden for so long. Recently though since I been single so long that I don’t care about the outcome anymore I just tell women up front that I chat or meet that I do enjoy a little crossdressing sometimes.. I make this known and up front now. Never has a good ending but I’m getting to old to keep lying and would like to meet a women that I can be with and make a family with.. if I have to drop this bit of a fetish of mine I would do that for the women I fall in love with. However I’m still single and can do what I please still. I still keep my panty wearing very secret. If I have to I’ll take it to the grave with me. I just hope to meet a women someday gets lonely. Still though being single has its privileges sometimes I go to a hotel room so I can dress in lingerie and have a good night sleep like that.. then I get up change into normal male working clothes and head off to work. Been doing it since I was a teenager and I’m over 30 now and still have kept it a secret. I’m only being honest here in hopes to help the next guy in this same issue.. maybe someone will give me good advice someday..

Joanne Watters on June 01, 2018:

My now ex wife was fine with my cross dressing for three years of our marriage. The first year she increased my dressing until it was every night & even had me sleeping in night gowns. The second year, she began taking me out while dressed & had me growing my hair & nails long. I only had panties, bras & pantyhose which she said I had to wear under my male clothes at all times, I didn't even have any socks to hide my ankles. She took me out to her hair salon & had me get a complete makeover including acrylic nails, waxed thin & arched eyebrows & pierced ears for Halloween that year. If my hair had been longer, she probably would have had that styled & colored. She made me go to work as a girl on Halloween then at my works party that night, she told all of my co workers that I dress as a girl all of the time & that I am constantly begging her to get me female hormones so I can have real breasts. From then on I went to work wearing women's slacks, a blouse, women's flats, earrings, nail polish, perfume, full makeup & carrying a purse. My work let me dress like this for four months before they found a reason to fire me. After being fired, my wife got rid of all of my male clothes so I began living as Joanne. She had me keeping the house, doing the wash & all of the shopping. By March of our third year of marriage, she took me back to her salon & got my hair cut, styled into a feminine style & frosted, she also told me that she has been giving me male hormone blockers & female hormones since last Halloween, she then asked me if I liked being a woman full time, of course I said yes, so she said it was about time she found me a boyfriend. She started bringing men home & had them teach me how to have sex as a woman, I must admit, I loved it, especially giving oral sex. It was September and my wife brought home two of her male friends, she told them that I would keep them entertained until she got back, she had an appointment to go to and she left. It didn't take long before I was on all fours with one guy in my mouth & the other in my butt, when in walked my wife with her mother & her aunt. My wife acted completely shocked, saying, how long have you been dressing like this & being with men, I cant believe this, I don't want to be with a woman, I want a man, a real man. She told me she was getting a divorce from me so I can be the woman that I wanted to be and didn't have to worry about her catching me again. Her, her mom & aunt gathered a bunch of her things and started to leave, my wife turned around and said, good by Joanne, I hope you become the woman that you want to be, then they left. I was not expecting anything like that, the sad part was, I had to go back to being a man to get a job, how I wish she would have stayed.

Brenda on January 15, 2018:

My partner is Angela re B.... n from day one I knew he was a T/V and completely accepted. Have always helped by buying wigs dresses bra & panties and did all I could to make him/her happy. He has turned on me. What the hell did I do wrong.

Steve on August 20, 2017:

I remember my wife at the time knitting herself two 'button to the neck' aran round neck cardigans one in maroon and the other in dark green, both with eight matching plastic buttons down the front. I remember trying on one of my wifes aran cardigans in her absense, I felt great being buttoned up in these lovely cosy cardigans. She also had a lovely long double breasted wool trench coat which I also loved wearing. She eventually discovered my secret wearing of her coat & cardigans and 'freaked out' saying I needed therapy. She is now my ex wife. However I still wear and own a large number of aran cardigans, some unisex, some male fashion. I have many chunky cardigans which are ladies cardigans with big shinny plasic buttons, usually in dark colours, which button on the ladies side up to the neck. I have even found a woolshop where they will knit cardigans specifically for me. I often wear these in public, with a pair of jeans. My present partner accepts my cardigan wearing and I have never received any adverse comments from anyone. I have received some knowing looks and some smiles from females, but hey I'm 65 now and not going to change, I feel great in my cardies and I'm not bothered what other people think.

The point is I couldn't be happier however now, but it important to be up front and honest in the first place, as difficult thow it may feel at the time.

Mrs feeling unhappy on July 09, 2017:

Why will he only have sex with me dressed as a woman? We used to have a good sex life being himself aswell as being "her" ...but now he only wants to do it if hes dressed up ...i dont get it and im feeling really confused and totally un wanted

Mike on May 14, 2017:

I'm a hard working straight guy yet I love dressing as a woman and I don't know how to explain it but it has always been there.

robert hathaway on April 13, 2017:

im a man who loves to wear womans clothes ans high heels to party on fri and sat nightsand I do

Matt on March 24, 2017:

I like panties and my gf doesn't judge me even when I wear the pink leopard spots

LJ on February 10, 2010:

If you do some research, you'll discover that in most cultures, (including ours) that pink was originally a boys color and blue was considered girly and frilly. Then along came the nazis and started associating pink with homosexuals and its been linked as a girls and gays color ever since. personally, I love the color pink and have never had a homosexual thought in my life.

Danielle on November 22, 2009:

Right said JSG "So, in the end, the clothing market will evolve (and us with it), to the point where men and women will be wearing whatever they want, and no one will care that a women wears a suit and boxers and has hairy legs and man wears a dress and a bra and shaves his legs." I for one have no problem with my husband weaeing panties, nylons and womans shoes which is as far as he dresses on a consistand daily basis. On occasion he will go all out and fully dress with make up and do his hair and nails and I'm ok with that too. After all they are only clothes and him dressing like a woman really isn't hurting anyone now is it?

It is his preferance and I'm kinda the one responsible for getting him started me and an accident but that is a story for another time. I've always been an exceping person as far as to each their own kinda thinng and I feel that in time it will be ok and maybe even accepted in our society.

JSG on September 25, 2009:

Is there really an issue with men wearing women's clothing? Yes. But, this is the way our society is. We, the human population, dictate what is correct attire for men and women, and what isn't. Any variation from this, is considered 'wrong'. If you take some time, and think back several years, it was completely unacceptable for women to wear pants. Pants were considered men's attire. These days, its completely acceptable for woman to wear pants, shorts, skirts, dresses an so on, even mix an match is fine (pants with a skirt). Men, on the other hand, are oppressed and, to an extent, forced to wear only what is considered mens clothing, or be frowned appon, ridiculed, forbidden access, laughed at, killed, etc.

As the clothing market changes and womens clothing is added to the mens attire (and vice verse), it becomes acceptable for a man/women to wear it, but not before (with exceptions like 'dress up', costume parties, or even Halloween). As an example, it was unacceptable for a man to wear pantyhose, these days, its at the 'OK' stage, and many men wear them, especially in winter. Now, there is a bra for men and mens underwear that look exactly like womens underwear, and I have noticed several where the only difference these have is the tag, the cut, color and style is exactly the same for both men and women. I men 100% the same.

So, in the end, the clothing market will evolve (and us with it), to the point where men and women will be wearing whatever they want, and no one will care that a women wears a suit and boxers and has hairy legs and man wears a dress and a bra and shaves his legs.

LatexLeah on September 23, 2009:

Peer pressure. Fear of discovery. Loss of status. When I, as "Leah", started leaving the house on shopping trips and other excursions, my proclivities, which had been known previously as a "hobby" became a problem.

Fortunately, nature ran its course and "Leah" faded from the scene. Apparently something had been satisfied and none too soon.

john on September 21, 2009:

I was confronted with the freaking out by my ex, eventhough she was the one who initiated that I would try skirt like garments. As our relation therapist pointed out lateron, considering circumstances I had to take over many a part of the tasks of my wife due to her illness. Hence by wearing a skirt also, she had in the end the feeling that I was taking over her role in to many a way, thus eventhouigh she applauded it in first instance, she did freak out (maybe also due to peer pressure)

sneakorocksolid on August 15, 2009:

Hope just deny my comments if you feel they're inappropriate.

Hope Alexander (author) on August 13, 2009:

Hi Lisa,

Thanks for your comment. I think you have a very good point, no woman should feel obligated to be attracted to anyone for any reason.

Still, (in many cases) I think it is less like comparing a man not being attracted to a woman in a lumberjack shirt, no make up and a man's hair style to a man not being attracted to a woman wearing a pair of men's boxer shorts.

You're describing full grown cross dresser behavior, which is a deal breaker for many. I should have been more clear in differentiating behaviors, so mea culpa entirely on this one.

Lisa HW from Massachusetts on August 13, 2009:

Many men are more than comfortable with "feminine sides" while also being completely at peace with dressing in men's clothing.

It is true that's it's all "just clothes", and people should be able to wear whatever they want. Still, I don't think there's anything "hard-line" about a heterosexual woman's not finding men in clothing (that's designed for a completely different kind of body) unappealing. A lot of heterosexual men wouldn't find it attractive if a woman wore a "lumberjack" shirt, no make-up, and a man's hair. style. This is the same thing.

As we hear time and time again, people can't choose what they're attracted to. That applies to heterosexual people as well as anyone else. This is where the "inflexibility" comes in, but I don't think there should be the implication that women who aren't "ok" with a guy in women's underwear are the ones who have, or are, the "issue". Being "inflexibly heterosexual" in what one finds attractive has nothing to do with being domineering or otherwise "not understanding". I agree with the author that men who want to wear women's clothing should seek out women who aren't "hard-liners" (but I think "hard-liners" is more often about being "at the far end of the heterosexuality scale" than about religious or culture).

Jakkie on August 10, 2009:

Women, like men, can sometimes be complicated individuals.

My feminine journey started at the suggesting and urginging of my ex-wife. Later, she became angry when she learned how much I truly love wearing feminine apparel.

Oh well, she's gone and I'm still in panties and nighties!

Mike on August 09, 2009:

I think people should just be able to wear whatever they want.Its just clothing ! As soon as we are born its pink for girls or blue for boys and that's the problem.As a male I love the color pink on me.So wearing pink panties is normal for me.

Related Articles