Dear Gabi, I Do Not Understand Crossdressing

Dear Gabi,

I did not nor do I now understand crossdressing. I was raised very religiously and naive as to what the world’s about. When I met my husband, 30 years younger than me, his mom would say that once we got together his bisexuality and crossdressing would not be there, but to my horror it was an every day thing and that he wanted to be a girl.

I’ve tried for all these years to deal with it give him some of my clothes, watch porn, deal with him chatting with his gay and crossdressing friends that don’t understand where I’m coming from. I’m severely depressed and this has only driven me farther and farther into it. I had problems before but this has escalated it.

After his mom’s death he wanted to start it up again and I said no. For the first time in our marriage he’s talked about it, now wants to go on with his life as were separated, and moving in with another bisexual and soon there will be a relationship there. He led me to believe that we could work things out sometime in the future but hit me with separation (same as a divorce) and he’s moving on and being what he is. This has torn me up and anxiety depression and feeling inadequate and the scum of the earth.

I’ve asked the docs and therapists for help it’s not enough. All I do is cry and feel like a complete failure. Even though I should just not talk to him and cut the ties, I can’t do it. My love is so deep and yet it’s obvious he only used me for money and getting what he wants. I’m not trying to step on any toes here, I just don’t understand and it’s messed me up so bad I can’t function. I have serious health issues and yet I can’t get disability and I’m on Lexapro and Clonazepam, but they’re not working. They won’t let me see another doctor or counselor and tell me to deal with it.

The same as my husband tells me about his crossdressing and bisexuality, the only support I have is my family and friends who think he should’ve been honest before we got married when he only wanted to talk when he was in my clothes! That’s not the time to talk to me about it. This is a lot of info and I’m sorry. I’m trying whatever I can to get help to get understand and I’m tired of hearing it’s not me. I feel after this being the 3rd marriage and other relationships have gone bad and left me with feeling very inadequate, I’m a failure and shouldn’t have been born.

Thank you for at least listening.


Gabrielle HermosaDear Chris,

I am so sorry to hear about your failed marriage and painful emotional struggles. There is nothing I can say or do that will heal your broken heart, but I may be able to at least shed light on some things that don’t make sense to you.

Crossdressing is different from one person to the next, therefore I cannot adequately spell it out in simple, logical terms. In general, it’s a man’s need to express his feminine side. Like being left-handed or naturally athletic, it’s a personal trait and not something that goes away or can be “cured” any more than one can “cure” being left-handed.

Bisexuality is a person’s attraction to and romantic interest in both sexes. It is not linked or directly related to crossdressing. Most crossdressers are, in fact, heterosexual men with no romantic interest in other men whatsoever. Most gay and bisexual men are also not crossdressers. Sometimes crossdressers happen to be gay or bi, and sometimes gay or bi men happen to be crossdressers.

May-December romance is tricky at best, depending on the age discrepancy. Romantic relationships between couples, in which the age difference is significant, tend to have less of a survival rate than couples who’s age does not differ greatly. The 30 year gap between you and your separated husband is pretty significant. Although age difference alone does not necessarily mean a relationship is doomed to fail, it certainly plays a considerable role.

I understand that you knew little to nothing about crossdressing or the significance of one’s sexual orientation before getting married. It was ignorance on the part of your husband’s mother to suggest it would go away once the two of you got married. Marriage does not change one’s sexual orientation/preference or their need for feminine self-expression.

It was admirable of you to try and be open to your husband’s crossdressing and sexual interests. Unfortunately, his desires (and perhaps needs) went well beyond just crossdressing and porn. You should not see this as a failure on your part because it has nothing to do with who you are as a person, and everything to do with what your husband wants and needs in his life. In other words, do not blame yourself for your husband’s behavior.

I can’t help but wonder if your husband may be more of a transsexual than a crossdresser based on your saying “he wanted to be a girl.” If that is the case, it is likely he has felt this way for a long time. Crossdressing and transsexualism are two very different things. Although both may involve the act of crossdressing (as in someone who is genetically male dressing as a female), the motive for doing so differs. Both are also very complex subjects and explaining the differences is better suited for a series of lengthy books.

You are absolutely correct in that your husband should have been more honest with you about his long-term interests and desires. Life is a discovery process however, and it’s possible that he may not have understood these aspects of his own life when the two of you were engaged to be married. Regardless, he was not as open and forthcoming with you as he should have been. This is, unfortunately, somewhat common among transgendered people. The fear of rejection compiled with the desire to live a “normal” life often keeps people from being completely honest about these things prior to marriage. It doesn’t make it right, but it does explain why it happens.

Marriages do not fail because of crossdressing or sexual orientation. They fail because of compatibility issues, lack of respect, and poor communication. In your story, I see some significant compatibility issues, and lack of communication. The respect factor is debatable and unclear in your letter, but the other two shortcomings are more than enough to cause a break up. For a marriage to work, both parties need to be equally committed and devoted to making it work. Both have to want it to work.

Although you have expressed difficulty in letting go of your husband, it is probably in your best interest to do so. You cannot hold on to a man who does not feel for you, as you do for him. It’s not healthy and nothing good will come of it. The sooner you let go, the sooner you can begin to heal and move on with your own life. You deserve a man who loves you completely and can commit himself to you in a monogamous relationship. Do not settle for less.

Before attempting another relationship, I suggest you work on your severe depression and low-self esteem. Depression, low-self esteem, and insecurities will cause serious trouble in any relationship. Failure to get these issues under control prior to entering another relationship will only result in another heart break.

There is no easy fix for depression, but it can be managed if you choose to work at it. Your solution will not be found in a pill or therapy alone. Medication and counseling can help, but the rest is up to you. Understanding this important point may be your first step to true recovery.

You’ve been through some difficult times and I hope that you’ll not think poorly of all crossdressers because a single man, and/or his friends. I am a heterosexual crossdresser in a monogamous and committed relationship with my wife. She knows all about my crossdressing and enjoys this aspect of my life with me. Of course, not all women will enjoy being with crossdresser. If the idea of crossdressing in and of itself is not a desirable quality in your eyes, that’s fine. Lucky for you, most men are not crossdressers. Everyone is allowed their opinion, but you should not sum up all crossdressers poorly because one caused you pain and suffering. Every group has its bad examples. Most of us are good, devoted husbands and fathers who are completely committed to our wives and families.

You’ve got some rough times ahead, Chris. I hope you will choose to overcome your troubles and move on with your life. The pain you feel will not be there forever. You’re old enough to understand that. This is a temporary state and you will come out of it stronger and wiser for the experience. You’re a good person and deserve to be happy. Do not place your self-worth on the success or failure of a relationship, but rather on your own good qualities. I believe in you, Chris. It is time to believe in yourself.

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10 thoughts on “Dear Gabi, I Do Not Understand Crossdressing”

  1. This lady’s story broke my heart as I see it as a failure of society to properly address these issues. Her husband’s mother’s ignorance as to gender identity issues and sexual orientation likely led to her husband’s confusion and desire to be “normal” and marry a woman that was not comfortable with his sexual orientation and gender identity.

    Chris did a brave thing in trying to accept her husband, but he was never given a chance to accept himself. She is not to blame. I do hope she realizes that and finds some solace.

    1. You brought up an excellent point, Jay. Although I suspected Chris’s husband was attempting to live a “normal” life in his marriage, the potential for pressure from his own mother to do so did not occur to me. It makes perfect sense and I’m sure it is a scenario that plays out frequently.

      It is very sad – people feeling pressured into living their lives one way, that which is considered “normal” by everyone around them. This pressure weighed heavily on my own life and almost caused me to self-destruct 20 years ago. Like so many others, I also got married without telling my wife-to-be out of the fear of rejection… and also because I believed it would go away when I got married. I was so naive to my own identity as a transgendered person… I didn’t want to believe I could be this way.

      How many of us feel the pressure of society to be what is expected of us? How much trouble does it cause? Not only in our lives, but also in the lives of those who become involved with us.

      I got lucky – my wife not only accepted me, but also ended up enjoying this aspect of my life very much (it is something we can share). Many others will not be so lucky. Marriages will shatter, people’s lives broken… some people will in fact choose to deny who they truly are in an effort to live their life as a lie – the life society tells them is right and just… a gay man living a “straight” life, or crossdresser living as 100% “man”, or perhaps a mix of both. Whatever way it turns out, at least one party will end up very unhappy in their life. And if they choose to leave and live their life as they are… a broken heart is left behind.

      The pain and suffering seems needless and senseless. If we could all just be honest up front, so much of this would be avoided. The honesty isn’t easy in a relentless world of conformity. Although some are purely selfish, many others are simply trying to discover who they are… and otherwise good, caring people get hurt in the process.

      Conformity is good though – let’s all just keep it up. Best to live miserable lies than to find happiness and peace in the truth. ;)

      And please forgive my mini-comment-rant. It just comes out sometimes. Best to let it out than to keep it all bottled up and chance it coming out at the wrong time. I’m sure it happens to all us “freaks” at times. But at least we’re real. No Leave it to Beaver here. :)

  2. “How many of us feel the pressure of society to be what is expected of us? How much trouble does it cause?”

    A clue on that – it’s still in the triple digits in South Texas without a break… I’m still not wearing a mini-skirt ;).

    1. “it’s still in the triple digits in South Texas without a break… I’m still not wearing a mini-skirt ;)”

      I’ve got extras… what size are you? I’ll take the next flight out your way. No one should be wearing PANTS in that kind of weather! lol

      I ranted a bit in my last comment, but one thing is for certain. When society applies too much pressure to someone like me, I push back. I can’t change the world, nor can I open the collective mind of society, but I’ll be damned if I’m going to restrict myself to socially accepted norms. Play it safe as needed? Sure. Play by their rules? Not a chance!

      I make the rules in my life, and I’ll share my knowledge with anyone interested in truth and reality. It’s time to see the world in full color, Dorothy.

      I know you already see the world in living color, Jay… and learning more every day, as am I. I’ll make whatever difference I can. I know you will too, my friend. :)

  3. “Crossdressing and transsexualism are two very different things. Although both may involve the act of crossdressing (as in someone who is genetically male dressing as a female), the motive for doing so differs.”

    Pardon me while I work out some of my own thoughts in public here, but I’ve been lurking about while reading the material published by so many in the gender outlaw community, the truth of this comment of yours is becoming very evident. It seems (to this casual observer at least) that the difference (perhaps) comes down to the difference between *expressing* your feminine side and *embedding* yourself in society. It’s a fiddling fine distinction – and in truth the CD and TS communities are much closer than anything in hetero-normativity, but that’s my take on it.

    Perhaps a bit of self-disclosure is in order: I’ve been living the masculine role for close to 45 years, having decided when I was six years old that, basically, I’d much rather have been a girl. Other circumstances in my life have forced me to open Pandora’s box, and I’m basically trying to figure out what to do about it. And frankly, I can only see CD as a means to an end – which is the renegotiation of my current social roles.

    And I’ll spare us all any more tedium of my continuous flopping like a fish out of water while trying to find the puddle of gender identity where I can breathe for a bit, and simply end here by saying, that I really appreciate your own candor. There is a difference, even if it is hard to articulate. But in any case I am wholeheartedly with you as we try to deal with the mess our culture has made of such a fundamental part of our identities.

    1. Thank you for sharing a bit of your own story, Dayita. I thought it was interesting, and sadly accurate, how you used the phrase “gender outlaw community”. In many ways, that is exactly how most of society treats us. There’s nothing illegal about being who we are, but if social standards and “norms” were the law, we would definitely be outlaws. Of course, if that be the case, there are some laws that just NEED to be broken. In this case, certain idiotic social standards that need to be eradicated. I can’t exactly eradicate them myself, but will fight them until my last breath has been taken… and then one more punch to the balls before I’m done. ;) heehee

      I’m sorry that you’ve been stuck in a role that you would not have chosen if the choice had been yours, Dayita. That’s the real problem – the choice really is yours, or all of ours, but it’s not really that simple and we all know it. The consequences for existing outside of society’s little security blanket of gender rules can have very devastating affects on one’s life.

      Do you truly feel as if you’ve opened Pandora’s box though? You’ve obviously decided to allow yourself to explore your feminine side, or perhaps the female you’ve always been inside, or would rather have been. Aside from how society treats this, and us, does it trouble you to a high degree? What I mean is, are you troubled about who you are? Or is it mainly just how things will fit within your “social role”? I’m guessing the latter, but I understand that psychologically the social role thing can really do a number on how one feels about who they are as a person. That is, of course, something I’ve had to deal with all my life.

      What do you want, Dayita? Forget about what you feel as if you’re allowed to do or to be in life – what do you WANT? What is it that you want and need to be happy with who you are as a person? You deserve to be happy just like anyone. I understand the need to conform and the consequences for not doing so, but I also understand what it is like trying to live my own life as a lie – it almost destroyed me.

      I can’t change the world, but I’ll be damned if I let it change who I am… or better put – dictate who I can be. Who are you, Dayita? I know who you force yourself to be, but who are you really? I bet the question is not who you are, but rather how can you be yourself and still exist within the constraints of society? Again, what do you want out of your life? Think about. Identify it. Then TAKE IT. Make it yours. After all, what I believe you truly want is simply to be who you are, and that is something you already have the power to take! :)

  4. I could help women understand CDing – “if” I had a complete understanding of it myself. At 54 years of age, I’ve cross-dressed in varying degrees, quite literally for as long as I can remember. (the better part of 50 years – OMG!) I’m sure the mental health professionals would tell me things I didn’t want to hear, so I’ve never bothered seeking their ‘advice’.

    I’ve revealed my ‘most intimate secret’ to a total of two (2) people in my life in hopes that they’d understand. Neither of them did, but the one that accepts that c’dressing is a part of ‘who’ I am (as opposed to ‘what’ I am) has been my wife for the past 25 years. God Bless her, and all women who at least try to understand ‘us’.

    We’re not bad people, ya know?

    Or, you might think of it this way: Sometimes I dress ‘ala femme’ in the same context that sometimes I wear blue T-shirts to work, and sometimes green, or gray, or…..

    Get the picture? 8^)

    Best to all,

    1. You pretty much nailed it on the blue, green, gray t-shirt, Marci. The only major difference is that there is no social taboo in wearing a blue t-shirt. If there were, I’m sure plenty of people would be wearing blue t-shirts in private, trying to keep it a secret, and trying to figure out: “Oh what strange force makes me want to wear this blue t-shirt? God help me for I must be crazy to like this blue t-shirt!”

      Turn any perfectly normal activity in to a social taboo and it will wreak havoc on the minds of people who would have otherwise simply enjoyed said perfectly normal activity, and probably cause trouble in the lives of their loved ones as well. ;)

  5. You know, I wonder if this lady ever looked at the presentation she does, and how she wearing pants would have been counted as crossdressing.

    She says she does not understand crossdressing, well I have a hard times understanding women supporting double standards.

    You would think they would want to do away with all double standards seeing how they were victims of many in the past, and still are in some ways.

    1. I hear you on the double standard, Pythos. It is an argument brought up time and time again, but gains little traction for many reasons. I’ll try to devote a post to that argument and why it usually fails in the eyes of the mainstream.

      Chris is allowed her views, as are we all. Right, wrong, or somewhere in-between, we all have out idea of how life should be. I think the main issue here was a matter of incompatibility that existed from the start and was overlooked by both – probably the result of wishful thinking from each.

      If a marriage fails because a man falls in love with a woman in his workplace, the wife (soon to be ex) might blame it on his working long hours and if only he had been home more often, this wouldn’t have happened. She then may be inclined to be bitter toward any hardworking business man who spends most of his time at the office, believing that he is “cheating” his spouse by doing so (even if not involved with a co-worker). Because there is no social taboo associated with working long hours at the office, this kind of argument wouldn’t be of much interest to most. I hope that made sense, anyway. Been a long day for me…

      In short, I think Chris has demonized her husband’s crossdressing, sighting it as the main (or even sole) reason for the failure in their relationship. She wasn’t a fan of crossdressing to begin with, and it makes for an easy scapegoat (being something of dislike in her ideal view of life). It’s easier for people (meaning any one of us) to find purpose or significance where there is none when we cannot understand the reality.

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