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!


  • Abbie

    I love and appreciate your articles. I have been wearing women's lingerie since my early teenage years. Early in my marriage my wife found women's clothing i forgot to hide away. I always enjoyed dressing up and it's grown from clothing to full Transgender transformation on a part time basis with makeup and wigs and jewelry etc… my wife was always confused more than me as to why i choose this part time lifestyle. Your articles have helped her and me so much. Following your advice to fit me has help me to create a new me "Abbie". I still have not ventured out in public for my own fears. We as people worry too much. Please continue your wonderful advice articles. My wife says Abbie treats her nicer than the man she married. We are creating a great relationship. I applaud all of you Brave Souls who are confident in being who you want to be. And admire your fortitude to go out in public any way you want. And enjoy who you want to be. My love to All, and a special thanks to all you brave women who are sometimes men.

  • Jenna

    I could never tell my wife without a break up because her feelings came out when the bathroom issue became national news. She believes T's need mental help and is totally against them. However, I believe she thinks something is up with me because I once did my own laundry and threw in my panties and I forgot to take my clothes from the dryer and she did but my panties were gone and she never brought it up. I am in a transition and I eventually will have to discuss because I have been quoted FFS surgery costs and facial hair removal and she must have noticed my breast growth which I am approaching that window of maximum breast growth from hormones.
    Kathy I appreciate your articles

  • M. J.

    Hi girls well I'm at the point I believe in my latest relationship we haven't known each other very long yet but I don't want to hurt her anymore than I want to be hurt myself so I feel I should tell her just to get it out in the open so as not to mislead her as seems very sweet but she is telling me a lot about her Christian values which I believe I have as well I'm sure most of you know how it might hurt to tell it could very well end our relationship and that's the hurtful part of that equation and yes I know its not math LoL and so I've got to own up and confess but at least it's early enough I hope before we get too attatched to each other if it's going to end might as well get it over with at least that's the idea oops there goes another good one maybe but at least I've cleared my conscious and told the truth hard as it is to spit out for some of us this life can be so confusing for us with this dilemma between ourselves and those we care for I hope things work out for us but I'm very fearful they will not I guess we get rather used to the rejection but it still hurts anyway I'll let you know soon LoL Love MJ

  • michelle

    it helps a lot if your wife knows and helps as well, she knew about my cross dressing and activities and didn't mind and thought it was kind of nice to see and watch. I would go out and about with very close friends to clubs and events and she would sometimes come along to see what was going on and see how I was acting and such. she would ask me where a head of time where I was going and help me pick my outfit out and she would even help me with my makeup and hair. she was bit surprised on what she saw and what I was doing but it was with my very close friends. as for co workers they don't know it might be kind of hard to let them know but I can tell you this I have seen a few of them at the clubs when I am there all dressed up. when I was first going out it was very scary and exciting at the same time but well worth it. it was one big step that I don't regret at all. take care michelle

  • Shanda Lear

    I think I am one of the lucky one's. My wife knows and thinks as long as I am home and treat it like a hobby, which it is, then it is fine. I have an extensive wardrobe and have not worn all of it yet though I am fully dressed at least 4 times a week. I have a scrapbook with many, many pics. My wife gets a thrill out of taking pics man y times when she is not out shopping (her hobby)((and she's pretty darn good at it too))(((both of her hobbies))). My daughter thinks I am fun crazy but with very creative since of fashion an\d often has me help her pick out an evenings wear. Almost all of my female friends know and have told me I look pretty good. They are much more understanding than my male friends .Actually none of my male friends or my family away from my house know. Since I am states away there is no reason for them to know. I am comfortable with my dual identity and have gone out in public quite a few times. (that still makes me a bit nervous) but all in all, I still consider myself as one of the lucky ones. Oh yes, I like this store and have shopped here often. Love to everyone and enjoy your adventures.

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