A Classic Dilemma: Do I Tell or Not?

do i tell about crossdressing

A Classic Dilemma: Do I Tell or Not?

The very nature of being part of a greatly misunderstood minority makes most of us very secretive.

As we all know, crossdressers and other T people have long lagged behind the other “letters” in the acronym LGB (years behind in fact). Even now, despite the recent amazing advancement in awareness of T issues nationally and internationally, the general public, by and large, simply does not understand crossdressers.

I know I’ve said this before but it’s not altogether surprising really, given that many of us don’t truly understand ourselves!

Now, as we all know it’s about gender and not sexuality but the typical man or woman in the population at large simply doesn’t get it. A gay man can dress in a tee shirt and chinos or he can wear a smart three-piece, double-breasted business suit—but either way it’s often hard to detect that he’s gay. A lesbian woman can have a masculine style haircut and wear denim and a plaid shirt or she can don a pretty flowing dress—and, again, it can be hard to discern that she is gay.

But a crossdresser…? Most crossdressers I know, when attired in one of their En Femme dresses or wearing a set of slinky En Femme underwear and wig, look “180 degrees” different from what they look like in their male attire. Add in a change of mannerisms, walk and even speech—and you can see why the public doesn't know what to make of us! Labels such as being gay or assumptions that we all want to transition to be a woman are immediately levied at us.

Right, so now we’ve agreed that crossdressers are different to most others. We also agree that we need to be furtive, secretive and, above all, cautious—especially as there are still some people around who often take offence at what we do. No matter that crossdressing physically harms no one, there are those who will look to cause us injury or even worse.

But the point is, do I continue keep my secret?

Well, let’s have a look at some of the groups of people nearest and dearest to us:


Especially for those married crossdressers—and if you believe oft-quoted statistics that almost all crossdressers are heterosexual males with spouses—keeping their dressing a secret can be painful and highly fraught. To make time to dress and to keep hidden “stashes” away from prying eyes often needs the skills and organisational abilities of a military operation. The omnipresent risks of getting caught or discovered or forgetting to take off all of your makeup or nail polish can be very stressful.

So, do I tell?

Well, you know your partner better than anyone else. Some crossdressers tell their prospective partners before getting married or co-habiting—and some relationships simply flounder and go sharply “downhill” and dissolve, whilst others go from strength to strength.

Some crossdressers never, ever tell—and you can understand why. If you are already married or in a long-term relationship, the “fear factor” is exponentially higher. Questions with no real answers include: What if my wife/partner can’t accept it? What if she walks away from our (long) marriage/relationship? What if she tells someone…, everyone?

Family Members:

Even if you don’t have children, keeping your crossdressing desires and needs hidden from family such as parents or brothers and sisters can be very hard also. After all, they raised you or you grew up with them, so they should know you better than most. They are more likely to spot your longer than average fingernails or notice that you have trimmed and shaped your eyebrows just that little bit more than most men.

Of course, some of your close family may have vague recollections of the time you were caught in a dress when young or when your younger sister persuaded you to dress as a girl for Halloween or the like.

Most crossdressers find it hardest of all to even approach this subject with their parents—in almost all cases certainly with their father. On the other hand, many crossdressers have a special empathy with their mothers (after all, possibly but for quirk of fate or a dose of estrogen, we could have been their daughters!). Yet it’s nevertheless hard to summon up the courage to try and explain to people of another generation just exactly why it is you have the need to dress as a woman sometimes.

Children, brothers, and sisters may be slightly easier to deal with—although the law of averages suggests that, for every 3 or 4 siblings or relatives who are comfortable with knowing you are a crossdresser, 2 or 3 will be aghast and may well terminate—overtly or otherwise—your relationship.

Work Colleagues:

It’s often said you spend more time with your work colleagues than you do with your family—often 9am to 5pm every day of the week. In any office or work environment, people watch each other carefully. They get to know all about their co-workers lives, trials and tribulations, and habits and foibles.

They’ll see the admiring glances you give to someone’s new dress. Or the way you look appreciably at your secretary’s new shoes, or possibly they’ll notice that you always spend more time talking to women in the office. They’ll observe that you are not really “one of the boys."

It goes without saying that, like it or not, in many cases revelations that you crossdress can be damaging to your career (unless, of course, you are the boss!). Despite notional protection for all in the workplace, office or workplace intrigue/politics, coupled with subtle pressures brought to bear, all add up to problems galore for anyone who dares to be different.

Close Friends, Associates, and Other Men You Know:

Many crossdressers really don’t like to hang around with other men. We’d much rather be in the shopping mall getting some retail therapy or in the beauty salon getting a manicure or the like. Yet, some of us do try to camouflage our differences by joining golf clubs, sports clubs, and maybe even work-related associations. There are also other male-dominated bastions we join so as to keep up appearances. We’ll probably make some good, close friends from within and spend some fun times bonding with other men—yet always just that little bit aloof.

But, now and then, maybe after a few drinks, or in a particular happy moment, the temptation is there to confide in someone you are close to, to tell them what you really like to do in your spare time. Easy to tell, hard to hide…

Is there a single, right answer?

In a word, “No!”

"If in doubt, don’t let it out" is an adage I heard when I was young. But I also heard, "What people don’t know doesn’t hurt them!"

In reality, it’s for you and you alone to make those calls and make those decision—and don’t let anyone tell you otherwise!


  • Barbara

    I feel a strong obligation to share my story of sharing , and the possible consequences. First, follow the author, Kathy Hamilton's, advice "When in doubt, Don't let it out!" And what Jenna said about her wife. "T's need mental help". I have been dressing for decades. I began at age 4 and crossdressing has always been a very lovely part of my life. I love being Barbara. That said, years ago I wanted to share this harmless, happy part of my life with my first wife. ( Heavy on the first wife). I got up my courage and told her. To my surprise, her response was encouraging and "sounds like it might be fun" was her reply. Little did I know I had fallen in an evil trap. She had a boyfriend and had been cheating on me for years. I had no idea. Months pass as I feel free to dress openly and start thinking I have the most understanding wife. Lucky me. That was until she serves up "I want a DIVORCE." Next thing I know, I am in a court room filled with her friends, lawyers and a judge answering this question under oath, " Yes or No. Do you ever wear women's clothes? "yes" I replied. "Do you get enjoyment from pretending to be something that you are not"? It went over a cliff form there. Everyone in that room judged me. It was one of the worst if not the worst day of my life. Divorce granted due to "incompatibility " What did I learn. I am not really sure why I love to dress. I can not explain it. Therefore, be careful trying to explain this wonderful part of yourself to someone who will never understand. What people do not understand, they "judge". It scares them. I remarried and have a wonderful wife. She does not know and I hope she never does. I love her and it would only hurt her. I struggled with not sharing and a few years ago sought help from a female Therapist. She was a blessing. She said " there is nothing wrong with you and as long as your dressing does not harm the feelings of others or you force your expectations for them to understand, enjoy dressing. Your wife does not tell you every aspect of her life. You do not have to share everything with her. " I know that time have changed for you younger "ladies". Our culture is more accepting. But be very careful of sharing your passion. They may not want to know as much as you want to tell. Have fun dressing! Barbara Jane

  • Daniel

    So I am at war right now in my mind. The mothers of my kids know all about my CD my first borns mom was the one who encouraged me to do the Halloween thing she said "be a hooker for Halloween and that is how the full wardrobe started before it was only bra and panties and it was like she knew somehow.well that Halloween evening after our companies party we went home and became intimate and had our most amazing sex. Things would never be the same after that. We both wanted that amazing sex without the taboo of dressing me up relationship fail number #1 . Now these are adult relationships , as a teenager I would steal my gfs bra and thongs anywho,second relationship five kids and nine yrs worth of relationship . I was heavy into partying our first two yrs and dressing up was part of that escape, I would drive put of town by myself cause at this point I've yet to tell her but after two yrs of lies and excuses, oh and she found things not her size in hiding spots for the items that were too cute to throw out before I came home Sunday sometimes mondays when I really loved an outfit or heels I couldn't part with but like I said out of excuses and lies and her discovery of said women clothing she accused me of cheating and I loved her way to much to have it end over ironically a lie ,well it forced me to tell the truth and that's when the amazing sex reentered my life 7 yrs later it wasn't exciting to her as my cding only progressed to passable and she wanted her man back so there went that whatever that was well three more relationships and they all at least tried to keep an open mind . Now my war I live 300 + miles from that life and have new friends and coworkers and I ha e kept this part of my life pretty hidden I li e in the country so I venture outside quite a bit however I was walked in on and this girl ran straight to the phones but her story was exaggerated as it included another man and I was alone and the girl was already mad at me and everyone knew it so I played it as frivolous accusations by the broken hearted ,that's another story I wont get into right now .But at the moment I find everyone is becoming more curious.Nail glue is still on my fingernails every morning
    , I have left full attire bra and breast forms under my clothes when my only guy friend has come over and he doesn't bring it up pretends he doesn't see but why do people feel the need to investigate in a creepy manner peep thru blinds listen thru walls and nose to the cracks with eyeballs drilling there way just about e to catch even the slightest glance at what I'm doing I don't know if I should just put that cat to rest or let there curiosity carry on . I mean I want the freedom to walk outside the way I want but I e heard how they talk about the other transgender in my area and I say I don't really care what THEY think however . THEY are my are my customers I e done work in the whole town . Please help!!

  • gail

    Since I've gone through a partial transition, complete with HRT, but never saw it through to the finish line, I have never felt the need to reveal my proclivities.
    i enjoy having what amounts to a secret life, and take no small amount of pleasure from concealing this part of my life from family, close friends and strangers alike.
    i'm sure this says something about my integrity or lack thereof.
    My only regret is to never have transitioned completely.
    At 70+, I'm afraid, and fear stopped me from living the life I most wanted, that window has closed, and, at for least now, I plan on taking my secret life to the grave.

  • Dave

    I truly wish I could tell my wife. However, I know that she would freak out and that would be the end of our marriage. My situation is that I'm married but prefer sex with men – so I'm a homosexual CD. That makes it even more difficult because not only will she discover that I like to cross-dress but she would then find out that I'm gay (or maybe bi). Either way, while I still love her, my sexual desires are for men only.
    Can someone out there please give me some advice on what to do and how to handle this situation.


  • Kathleen

    I've been cross dressing for 60 years, I'm still married, but living by myself in another State. Living alone has allowed me to pursue my hobby and live at least part time as a Woman. I have driven around the neighborhood and the block, something I never would have done while living with my family. I did come out last year to my daughter and eventually to my son and my close cousin. If I had that to do over again, I would have made a different decision. But now they have to deal with it, I'm free of guilt. I do love becoming Kathleen, as it has been a happy place for me and a real stress relief. I really try to do my best to pass, but I'm not sure that's possible. Someday's I just love getting up in the morning, throwing on some Women's clothes and a little makeup and playing housewife, I do the chores and laundry with much more flair than in boring boy mode. In fact, when I get dressed for work in the morning, I often find myself saying "I hate boy clothes" So now I'm more comfortable with myself. I was in a local discount store buying jewelry, and the sales girl asked kind kidding, but not really, "are these for you" I looked at her, and without batting an eye, said "Yes, the are" She complemented me on my selection. No big deal ! So keep the faith and enjoy that feeling of living as the other gender, it definitely has made me a better person.

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