When Cross-Dressing Puts Relationships in the Crosshairs

Black dress and purse on bedA long time ago, my (much older) bachelor next-door neighbor confided in me that his pleasure in life was purely “sartorial.” Unfamiliar with the term, I ran to my dictionary and learned sartorial meant “pertaining to clothing, especially men’s.” But this distinguished college professor was no dandy—his clothes appeared unremarkable, plain, and masculine.

As we became better and better friends, he confessed to me that his sartorial interests were with feminine clothing, and that he had been wearing female lingerie under his tweed suits for many years. He lamented that he had lost his last girlfriend years before when “the allure of her panties reared its satin head.” What offered a sexual turn-on for him was a turn-off for her.

He wanted my help with shopping for dresses, but I was wearing work shirts and overalls—this was the early 1970s, and nobody condemned me for dressing like a male farm worker! Since I couldn’t offer shopping assistance, I spent time with him and listened.

Henry was lonely and felt keenly isolated. He felt he didn’t fit in with gay men. “They would think I’m a homosexual hiding out in the closet and avoiding my desire for another man,” he would say. He thought transgender people also disdained him: “They think I don’t have the guts to act on my transsexual longings.” Henry was sexually attracted to women.

Since that time, I’ve learned much more about cross-dressing, a type of compulsion or need that some people, primarily men, have to dress like another gender, also known as “transvestism.” Apparently Henry’s sweetheart was fine with this until he began raiding her underwear drawer.

Most male cross-dressers I’ve met since then are heterosexual, married, and the last guys you’d imagine dressing like a girl. Many choose macho professions to help hide or mitigate the feminine side of themselves—jobs such as firefighter, auto mechanic, or plumber. A male cross-dresser may derive sexual excitement by identifying with a woman, but he can still maintain a heterosexual consciousness when out in the world.

I don’t know what happened to Henry. I know he yearned for a female partner who would understand. He especially hoped that one day he would marry a woman who could accept him with all his quirks and proclivities. Back then I don’t believe there was as much support available as there is now.

Guys reading this while wearing frilly garb might be concerned about being caught. This fear is shared by many cross-dressers. You might want to look at the most recent edition of The Tranny Guide, sometimes referred to as “the tranny bible”—a book full of helpful and humorous suggestions. Laughter can really help! Another book that many people have found useful is The Man in the Red Velvet Dress.

Therapy won’t take away your desire to cross-dress, but it can help you find peace with yourself, especially if your intimate relationships are being adversely affected.

So, what if you’re a wife or girlfriend discovering your guy’s sartorial interests? I recommend a 90-day “chill” period before taking any drastic measures. Talk to him about what he does and why. Read anything written by Frances Fairfax, especially A Wives’ Bill of Rights. Look at the site for The Society for the Second Self or “Tri-Ess,” a national organization for cross-dressers, their wives, and their families. These folks do everything from campouts to discussion groups to bus tours, and they may be able to help you find a local support group.

One wife told me years ago that it would have been easier to accept her husband if he announced he was gay. She felt scared she would lose “the butch part of him—the manly part.” That didn’t happen. Over time, she came to terms with it: “There are worse things he could be doing, and I’ve found he’s the same guy I fell in love with before he broke out the Little Bo Peep outfit for Halloween. I don’t always condone his fashion statements, but I don’t need to divorce him, either.”

© Copyright 2014 GoodTherapy.org. All rights reserved. Permission to publish granted by Jill Denton, LMFT, CSAT, CCS, therapist in Los Osos, California

The preceding article was solely written by the author named above. Any views and opinions expressed are not necessarily shared by GoodTherapy.org. Questions or concerns about the preceding article can be directed to the author or posted as a comment below.

  • Leave a Comment
  • Grace


    September 30th, 2014 at 10:23 AM

    Wow, now that takes a strong woman to stand by her man that is doing this. I am not sure that I would ever be okay with that, because all this time I would think that he was gay and that this was his way of expressing that. I am fine with that on its own, but not from my husband!

  • Mavericksa


    January 23rd, 2017 at 8:55 AM

    If your husband did cross dress your issue surely would stem from the “I would think he was gay” part of your statement. Also I strong is not necessarily the adjective to describe the woman. Open, non judging, caring, accepting and most important trusting. Understandably it took my wife many weeks to accept the truth after finding women’s clothes. He mind only wanted to believe I was cheating. Why wouldn’t you accept it “in your husband” afraid what the neighbors would would think and say? We ALL have masculine and feminine energy in us. Woman are beautiful and so are men sometimes expressing that in all kinds of ways feels good. I am far from being attracted to men. Food for thought. w/love. All One.

  • Joanne W.

    Joanne W.

    November 9th, 2019 at 7:40 PM

    I love dressing as Joanne & having sex with men, I should have been born a girl

  • janney


    November 11th, 2019 at 7:08 AM

    To each his own “Joanne” but I pray you don’t catch a disease. No one cares who you fornicate with or what you enjoy.

  • MaryJane


    November 11th, 2019 at 2:25 PM

    To Joanne, dressing up and being homosexual for sexual activity doesn’t make you a girl. A woman has menstrual cycles, a uterus, can give childbirth. You just play “pretend” you are a woman.

  • Mavericksa


    January 23rd, 2017 at 9:26 AM

    “Her mind….” Here is an article that 95% rang true. tgforum.com/wordpress/index.php/background-papers-on-transgender-issues-from-renaissance/reasons-for-male-to-female-crossdressing/ CD ing goes deeper than article talks about. I can only be honest I haven’t fully grasped a complete understanding of the why for my self. Also men have a strong desire for female attention and it’s not uncommon in a marrage or just in life for woman to have a some what less desire for that “attention” from men that men desire of a woman. Men and women cheat however men seem to get caught more. I am a faithful devoted husband and and known for my creativity. CD is a way to experience femininity if only in a fantasy escape with myself. The deeper also has an element of the inner child and “toxic shame” as John Bradshaw outlines in is work. Healing The Shame That Binds Us. Whether one admits dealing with toxic shame we all have some element of this because we all where children at one time and it would just about impossible to not have had one or two events effect us as children. It doesn’t take much. Children are such sponges and look up to all the adults and other children to learn “how to be”. Up till about the age of 7 as far as understand, after which we start to take on our own personality and build upon the base that was establish during the first 7 years. Even acts that a child was near like adults fighting or a husband raging at the wife in the other room will effect a child and has the possibility to cause “shame” . Or a wife griping at the father or saying something she Really did not actually mean just couldn’t help her self from saying it. Again JFLS w/love All One

  • Joanne


    June 1st, 2018 at 4:03 PM

    My wife did not like it when I would dress as Joanne but she put up with it for 2 years until I came home one night with acrylic nails, pierced ears & my eyebrows waxed pencil thin with a high arch in them, she asked me if I wanted to be a woman 7 I told her yes. That ended our marriage.

  • WP


    June 4th, 2018 at 8:33 PM

    Please understand that she as a straight woman attracted to males and masculinity has a right to have that attraction.

  • Deanna


    June 5th, 2018 at 7:31 AM

    Women marry men, to expect them to accept you as a woman is a bit much. Men who hide their crossdressing and then act like the wife should accept it or be turned on by it are fooling themselves.

  • Tracy


    February 15th, 2019 at 6:01 AM

    I am a cross dressing married man. I have found that I don’t get turned on unless I am crossdressing. My wife has been very understanding but she is losing her patience I can tell. I feel like I have let her down in some ways in our marriage.

  • cassaundra


    September 30th, 2014 at 2:39 PM

    I am not saying that I would like it, but you know, this is who that person is and what makes them happy so who am I to judge that? I don’t really want a guy who does that, but then again, if I met the man of my dreams and he like women’s panties better than he dows boxers, then maybe I could be brought around. I don’t know, it’s such an awkward kind of situation that I don’t even know how you start to have a conversation about it.

  • Margo


    October 12th, 2014 at 8:00 AM

    It is an award situation because we have been taught that male where boxers/briefs and women where girdles/panties. Truth is they never told us why. There is no law saying we have to wear assigned underwear, there fore if a man wants to wear panties he can and if a woman wants to wear boxers her choice. No law against it except man’s emotional law. If it makes them happy and stable hey i am good with that.

  • marc


    October 1st, 2014 at 3:47 AM

    It is not that you need to fight that urge and deny who you are, but it is all about discovering ays to tap into all parst of you and become comfortable with who you are. We all have our little quirks and differences and those things alone shouldn’t be a reason for us to feel unloveable no matter what they are.

  • anon


    October 1st, 2014 at 9:35 AM

    I don’t want to put my name out there becasue I am a little embarassed but I do what I do to feel a little better about me. I guess I am bi, I have loved men and women, but there is something about the woman’s clothing that honestly just makes me feel a little more special than my own stuff does. Is that weird? I don’t like to think of it as strange because this is something that I have wanted to do for as long as I can remember but the society as a whole sees it as strange so I try to keep it tampered down at times. I know that eventually I could meet someone that I don’t feel like I have to hide this from but for now I will just stick with the items that you can’t see underneath the clothes on the outside.

  • RonaldQ


    October 2nd, 2014 at 3:50 AM

    It could be that issues such as this are going to be easier to deal with and for both partners to deal with once all of the shame and secrecy is gone. If there is one person who is so busy hiding what they do and feeling horrible about it, then there is the other person in the relationship not getting everything that they need because the other is too busy hiding part of themselves that they never fully give one hundred percent to the relationship. They can’t because they are scared and afraid of what might happen if they are truthful and their partner does not understand and becomes unwilling to even try to understand. If you find that ability to get everything out in an open and honest way than I think that there may actually be a little more understanding and clarity there that has always been missing and could in the end result in a stronger relationship overall.

  • Margo


    October 12th, 2014 at 7:48 AM

    Ron I thank you for sharing that story. I add only that in the 1970’s it was shameful for anyone to cross dress. You use to get arrested for crossdressing and that may be why people avoided being seen in crossgerendered clothing. I am a classic tomboy from the time I
    was 5 years old. I hated wearing dresses even through high school to now. I will wear a suitskirt down to ankles or woman’s suit otherwise you will see me in bluejeans and a t-shirt or khakis. I express myself freely. If a man wants to dress in woman clothes he is free to do that, RuPaul put that on the map along with “Bosom Buddies” and “Tootsie”. After events like these people lightned up, it took awhile but people get the picture. Self expression in clothes of the opposite gender does not make them gay but it might help them understand the opposite gender better. I think that if a husband is crossdressing he might understand his wife better and vice versa.

  • Olivia


    October 3rd, 2014 at 2:50 PM

    please please please isn’t it easier to tell someone about your proclivities early on rather than letting them find out about them later one?

    At least give them the chance to make a choice whether this is something that they can handle or not before they get too involved and feel like they can’t back out now.

  • Blakely


    October 4th, 2014 at 6:04 AM

    so I am understanding that there is a difference between just plain old cross dressers and transsexuals? I mean, not every cross dresser wants to be a woman they just like to wear womens clothes?

  • raquel


    October 6th, 2014 at 3:53 AM

    The line about being a turn on for him and a turn off for her? Well that would be me. I guess that I have always had this very masculine ideal of what I want my man to be, and these two things would not jibe for me. I guess that that could limit some of my options (?) but I also think that it is good to know ahead of time what you wnat and what you can put up with in any relationship.

  • James


    March 14th, 2016 at 4:39 PM

    It is hard to find a woman that would accept me as an underwear crossdresser.. btw, i’m NOT a gay..

  • nico


    October 23rd, 2019 at 12:27 PM

    that is true i losse 12 years and still no one

  • Sam I Am

    Sam I Am

    October 29th, 2019 at 7:21 AM

    Either you find someone who loves you enough to accept it or you don’t. A secure woman will accept it while other women will fear it. If it stays home then everything is fine once a man starts going out it puts thoughts into a woman’s head that you are straying or need more attention. Tread carefully and don’t lose focus of what is important, which is your woman who is by your side.

  • Kari


    November 6th, 2016 at 10:30 PM

    I found out 6 months ago that my partner of 2 years is a crossdresser , and it has destroyed our otherwise great relationship.
    If crossdressing was as simple as just wearing clothes , im sure it wouldnt be a problem. These people that comment saying its ok for girls to wear jeans , pants etc and that its no different obviously arent looking at the big picture .
    Yes girls wear jeans and pants etc , but there is no sexual turn on involved in it at all , I wear jeans all the time BUT i dont feel the need to masturbate or have sexual fantasies while wearing them , im still the same person,I dont create an image or another person that turns me on so much that i feel the need to keep it hidden from society .
    Like i said , No its not always just about wearing the clothes its about what these clothes can turn your partner into that most wives and girlfriends im sure find hard to deal with , its the sexual componenets of the fetish side of this that i personally found disturbing , not just the simple ‘different clothes’ . For some its just not that basic and simple , it can actually change how you see that once perfect man you thought you had found.
    I dont want to offend or upset anyone here , im just saying things from my perspective.

  • mel


    February 8th, 2019 at 1:21 PM

    what you have explained is what I’m going through. its not just clothes. I was so attracted to my husband and wanted sex all the time. Now I am so angry. Everything he does makes me mad. I’m not attracted to him sexually anymore. I tired to play along with this, i did a lot of research too. “its harmless” was the most common phrase. Bull Shit! It Destroyed my very happy relationship in 6months. I am afraid I won’t be able to become attracted to him again. What do I do?

  • Jess


    February 14th, 2019 at 8:30 AM

    I agree completely. Once a fetish is established and out there it is hard for some partners to accept or play along. It is very deceitful for a person to hide something this huge also and expect their partner or spouse to accept it also.

  • Angela


    September 2nd, 2019 at 7:49 PM

    I just found out a week ago that my boyfriend of 1.5 years is doing this. He was a childhood friend who I fell in love with, and my kids, especially my 12 year old daughter adores. I was and think I am still in shock. He is very a masculine man in every way and I was always so attracted to him. I love him and thought we were going to always be growing together, but I dont know how I can knowing this is who his also is. And I dont know the full extent. I just happened to stumble on photos, and curiously looked at his email to see clothing orders, then found extensive number of shoes and clothing. I am heartbroken.

  • nico


    October 23rd, 2019 at 12:33 PM

    Angela sorry for what you felling :( , am same crossdreser and have similar story but i love only woman

  • Michelle


    January 9th, 2017 at 7:40 AM

    My wife was aware of my crossdressing when we married. She does not participate or encourage me in any way. I keep my body and legs smooth shaven; and would love for my wife to encourage, even better, order me to wear sheer nylons on a regular basis for her inspection, seeing as I keep my legs so feminine. She could even tease me about my crossdressing, calling me her feminine, “bitch husband”. Thus; I would truly enjoy a dominant side to her nature. Also; I’ve always had thoughts and fantasies of my wife openly flirting with other men, and especially having a personal, intimate relationship with another man. I’ve had these thoughts and feelings since before we were married, but could never tell her, as I didn’t want her to think I didn’t love her, and I didn’t think she could be open-minded or accepting enough to include them in our marriage. Maybe too little; too late.

  • Melanie


    May 15th, 2018 at 6:34 AM

    As long as my husband wasn’t gay I would be ok with it, but if he were trying to hook up with other men I would want out of the relationship obviously.

  • greg


    May 22nd, 2018 at 9:46 PM

    My friend and I are both hetero males.
    II am stuck in a wheelchair and he cross- dresses at home and in places he feels safe and comfortable.
    We live in a small town.
    Word got out that he dresses up and it is becoming a problem.
    It isn’t MY thing but as long as he doesn’t hurt anybody, why do people have to go out of their way to make him feel terrible?
    Now I am worried that I will get lumped in as a pervert by people in town for just hanging with the guy?
    It doesn’t bother me so why should it bother them?

  • Missy


    May 23rd, 2018 at 12:39 PM

    People just need something to talk about. They could care less about your friend/roommate and his crossdressing. People are also ignorant and tend to criticize what they don’t understand. You shouldn’t let it bother you that people may talk. As long as your friend is your friend and his habits/fetishes don’t hurt anyone then let them gossip.

  • Kelli


    September 11th, 2018 at 9:14 PM

    I think I need professional help dealing with my husband’s cross dressing. I am not ready to go public with my story, but I can’t hold my secret in any longer. Can you listen to me?

  • The GoodTherapy.org Team

    The GoodTherapy.org Team

    September 12th, 2018 at 11:04 AM

    Hi Kelli. Thank you for your comment and for visiting the GoodTherapy blog. If you would like to consult with a mental health professional, please feel free to return to our homepage, http://www.goodtherapy.org/, and enter your zip code into the search field to find therapists in your area. If you’re looking for a counselor that practices a specific type of therapy, or who deals with specific concerns, you can make an advanced search by clicking here: http://www.goodtherapy.org/advanced-search.html

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  • Ali


    September 25th, 2018 at 2:30 PM

    Hi Kelli, I’m also a wife who struggles with her husbands crossdressing.
    If you’d like to chat via email maybe? It is made so much worse that this topic can’t be discussed freely with friends etc.

  • Jane


    October 26th, 2018 at 10:46 AM

    I don’t trust any man who cross dresses on the side or hides it from his girlfriend or wife. If he hides that he is hiding other aspects of his life as well also.

  • Lynne


    July 9th, 2019 at 2:48 PM

    My husband revealed his cross-dressing fantasies after we were married. At first, I tried to go along, believing “to each their own”. I still believe “to each their own”, but i also believe this should have been brought up BEFORE we married. Now, I can hardly look at him, and keep thinking he married me under false pretenses. For the most part, he doesnt cross-dress, but when he does, the fantasies he spins out are just beyond my limit. (they mostly circle around me being “dominant” and him being a “sissy princess”. ) I dont blame him for his fantasies, but I cannot force myself to pretend I like them. Its now to the point I dont want to have sex with him at all. The cross-dressing doesnt make him a bad person, but it repulses me and leaves me questioning our marriage. I am not the least bit interested having sex with a man wearing a dress and him asking when we can get a strap-on so he can be penetrated. What to do?

  • Susan


    August 16th, 2019 at 8:21 AM

    Sometimes fantasies should remain just that, a fantasy. Trying to live out them just hurts and starts confusion among a relationship on how you can’t fulfill that fantasy or even want to. Try to love someone for the person they are. Don’t discourage or encourage the crossdressing.

  • George


    August 17th, 2019 at 5:18 AM

    I have fought cross dressing for my whole life. Once our children were born my wife said she could no longer have sex with a “transvestite” That was 20 years ago. Now I gave up the fight and wear skirts/dresses/lingerie full time while at home. She thinks there is something wrong with me???

  • susan


    August 19th, 2019 at 7:41 AM

    There are two components to this behavior. One is the act of crossdressing making you feel like a woman and the act of crossdressing turning you on. The sexual behavior can have dire consequences to a healthy hetero relationship.

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