“How Do You Know?”

If there is one question that is seriously prevalent to my being, it is this: “How do you know?” I’ve asked that question enough times to fill my car with silver dollars. If they made a crossdresser anthem, that would be its title. Although it isn’t just about crossdressing, as it pertains to being transgender as well as any deviation from what they have spelled out as “Normal Behavior.” The “they” in this case are society, politics, religion, culture, history… you get the point.

I’m a mess inside as I struggle to come to any satisfactory explanation as to what I am and what I should be. I am neither male nor female. Ask me today and I might tell you that I’m comfortable being a CD, tomorrow, I may cry as I long to shed the masculine shell completely and become the woman I am, and the day after that… who knows. So again, “How do you know?”

I could rattle off all the things that I do know and try to equate that to some semblance of a dignified answer, but I’m only kidding myself. I don’t know and I wish that someone could give me an answer that is black and white that would help me to know. They can’t because if there were distinctive signposts for us to navigate, we’d all be holding hands and singing happy songs as we walk a similar path and then step off at our designated stop.

En Femme Style

If I haven’t lost you, then let me try to rationalize my thoughts. I’m in constant turmoil trying to figure out “How do I know if I’m transgender… more precisely, I’m wanting to know what are all the feelings that make someone feel they are born in the wrong body and should be a female and must go through the process to rectify the mistake, and… I don’t feel that way. So does that make me, what exactly? Here’s the thing; if you gave me the magic pill, I’d take it in a heartbeat (that’s today and not me from 10 or 20 years ago.) My life is settled, and I can face all the obstacles that would come with a complete change. So, if I could take the pill, then why can’t I start the process on my own? “How do you know?”

I used to ask, “How do you know if I’m a crossdresser or just someone who has a kinky fetish for high heels and lingerie? That answer only came after years of trial and tribulations stemming from self-doubt, irritability, and failed relationships. It morphed into, “How do I know if I am more than a crossdresser and possibly transgender?” Does claiming oneself to be transgender suddenly mean they have to pursue hormones and sex reassignment surgery? Will I lose my club card in the CD world and not be fully accepted into the transgender sorority until I start some recognizable process that exemplifies that I am serious about becoming a woman? “HOW DO YOU KNOW?”

I’ve edited hundreds of articles that have asked and attempted to answer that very question, both on CDH and TGH. The multiple truths shared by everyone have only made that question more perplexing. There are some who indeed, KNOW. They know with every fiber of their being, and I applaud them and envy them. I’m drifting on the vast ocean searching for the mythical kingdom where I am going to be accepted for who I am supposed to be. It will likely be that I will die with that question unanswered. And maybe that is ok and in its own way the answer that I’ve been searching for. “How do you know?” could easily be reshaped to state, “Why do I have to know?” My happiness today, and long into the future isn’t going to be answered by a collection of points that detail a progression from here to there. My line is my line and I only need to accept what I am willing to, nothing more.

How do I know if I’m transgender? I don’t, but I think that I am, and it doesn’t matter if I don’t “Check” all the boxes. It shouldn’t take away from this wonderful experience, one that lets me enjoy being a complete crossdresser. I love femininity and there is nothing wrong with my appreciation of it. I’m single so I’m hurting no one—this is different for those in relationships. Not that I wouldn’t love to be in a relationship with an accepting individual. If it happens, great! I’m not holding my breath. I don’t know, so I’ll keep taking one high heel step in front of the other as I sashay along the path to… wherever I eventually land. My guess is that I will never dock my boat at the magical kingdom. It’s possible that I might even drift further away from it. How do I know? Who cares?

It’s time for me to be content in understanding that I won’t find answers to my questions in the stories of others, but what I will find are similarities that have importance to me. If I were to undergo some of the procedures, I can find examples of what to expect. That is essential information to have.

Each of us, in our personal way, asks the same question, “How do you know?” I think we feel the need to garner reassurances, an “It’s okay to feel that way,” even the recognition from our fellow members that our posted picture shows our inner female.  The line between being transgender and just a crossdresser is as blurry as a 1960s television station without rabbit ears. (Sorry, couldn’t resist throwing some “old” humor out there.) That is why many of us will never find that particular answer. And… that is perfectly fine because the only answer that you need is the one that pertains to you finding your balance in life and the means to navigate it with happiness and compassion.

If there was one thing that I wish I could have told my younger self, it would be this, “Buy the shoes! Wear the dress! Treat yourself and others with respect and love everyone for who they are and not what they should be according to what society dictates.” Okay, that was much more than one thing. You get my point. I spent too much time hating myself and it took a toll on those around me. Today, I live by being as compassionate as I can. I have lots of years to still make up for, but at least I now like the person (whether in a dress or not) I’ve become and am still becoming.

May your life be enriched by the duplicity of treading the line between male and female, it is most assuredly a blessing and not a curse…


Until next time…

More Articles by Sabrina MacTavish

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    Laura Moore 1 month ago

    Thank you Sabrina for that very insightful article. Without a long, long story, let me just say that I came to the realization that I am trans just recently. I have no doubt that I am trans, but do not know exactly where on the spectrum I am. I have a wonderfully supportive sister and an equally wonderful counselor who I have been seeing on and off for the past year. They have been my rock.

    I’ve also come to the conclusion that it really doesn’t matter where on the trans spectrum I am. I used to think that being trans meant SRS surgery. It does not. There are many variations and there is no one definition that defines all of us. The common thread to being MTF trans I think is knowing I have the soul of a woman even though I know I will never fully transition. If I had come to the realization that I am trans early on, I believe that I would have pursued a full transition. As a young child, I was so envious of Christine Jorgenson and wished it were me. I was never secure about my male persona. I grew up crossdressing whenever I could and when married started up again and came out to my wife after a few years of marriage. I thought that marriage would break me of the habit. We all know how that works. In retrospect, I never should have married. I could never really be the man that my wife thought she married. I deeply regret having hurt her. We didn’t divorce over it. She supported me for a while then we both drifted apart but stayed married. She is now deceased and I regret not being able to make amends to her.

    I am in my 70’s as of this writing and know that I will not fully transition. I would love to take hormones and that is still a possibility. I always thought I was “just” a crossdresser. There was a light that went on that convinced me that I am trans. I finally fully accept my femininity. The trans euphoria that I feel dressed or not is overwhelming and I happily reside “somewhere” on that trans spectrum. Exactly where I am on that spectrum doesn’t really matter.

    • ' class='avatar avatar-100 photo' height='100' width='100' /> Author
      Sabrina MacTavish 1 month ago


      Wonderfully put. I think that you confirm much of what I speculated. We’ve spent too much of our lives trying to be either/or because we believed that was how it had to be. I’m like you; although I would never give up my kids from a failed marriage, I wasn’t really the man I professed and tried to be. That is my fault. It doesn’t excuse her as we were incompatible regardless. I would be in a much different place today knowing what I know if I knew it then. So my hope is that our younger sisters benefit from hearing what we have to say. Maybe they can avoid much of the internal pain we endured and come to (their) place on that spectrum.

      Thanks for the comments!

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    Brielle 1 month ago

    Hi Trina, I haven’t been on the site as much lately as there have been a lot of personal things I’ve been dealing with, but I wanted to reply to your article. Your query has an infinite number of answers, none of them invalid. For me, I suspected as far back as 2015 (give or take), when I had most of 5 months home alone to rejuvenate my crossdressing. My wife was out of town helping sick family and I discovered Amazon clothes shopping. I got so wrapped up in it that I abruptly threw everything out well before my wife returned, because I was afraid I’d not be able to regulate it and only dress privately and in secret. I laid off almost all of it until January 2021, when my wife was working full days plus a lot as a Whole Foods/Amazon shopper. I was working full time remotely from March 2020 until April this year, so the opportunities were nearly limitless.

    In June of that year, I finally admitted to myself that I at least had to come out to my wife of 40 years as a cross dresser. I had already started gender therapy (initially told my wife it was to explore why I had so little interest in initiating intimacy, which was true then). The therapist met Brielle via our video sessions and commented how natural and relaxed I was as opposed to the uptight, very held-back male self. We were also seeing a therapist for marriage counseling and individual therapy. The same week I introduced both therapists to Brielle, they almost immediately, and separately, determined my anxiety stemmed from gender dysphoria, it wouldn’t go away on its own, and I would be better off health-wise to look into HRT. So I guess that’s when I “knew”, but it had been more than a 7 year process. When I was younger, I used to fantasize at night about being able to morph into a pretty girl or hot woman temporarily and at will, like a shapeshifter. So I was probably perteen and “knowing” I was transgender, but had no way of understanding or seeking out any help in the 60s, in a small, conservative WV town.

    • ' class='avatar avatar-100 photo' height='100' width='100' /> Author
      Sabrina MacTavish 1 month ago

      There is a lot of me in those sentiments. I’m even guessing that many others relate, too. When we hear/read about someone with gender dysphoria, it is usually about the severity that it can cause. I think that is where some of my wonderment comes from. I don’t feel right but can survive in my man’s shell. I’m much calmer and stress free as my female self. Is that GD? I plan to find out sooner than later… Thanks for the comments 🙂

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    Terri M 2 months ago

    Thank you Sabrina for your article. It made me think more of who I am. I am becoming more aware that I am transgender. But because of my family obligations I really can’t bring myself to go further. So may say that’s a cop out. But it’s what I feel.
    Yours Terri

    • ' class='avatar avatar-100 photo' height='100' width='100' /> Author
      Sabrina MacTavish 2 months ago

      That’s my point. Don’t put self-pressure on yourself. You don’t need to be anything but you. I totally get the responsibility thing… I have a 95-year-old father that depends on me—no need to spring anything else on him at this stage in his life. I can wait and accept where I currently am. As to the future, who knows…

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    Emily Alt 2 months ago

    I see transgender as an umbrella for lots of other gender identities. I see nothing wrong with using that as your identity. It works for me and it’s how I identify. I adopted the label when I still considered myself a part-time CD. I will continue to use the label regardless of where HRT and my transition takes me.

    Nothing new here. Other gender non-conforming folks of myriad flavors have been adopting the trans label for years. And it’s accepted practice in the mental health community.

    Taking a broader approach to our identity has some advantages.

    First and perhaps most important, it settles a question that many of us struggle with for years. Why not just say you’re trans and be done with it? It works.

    And as a side note for the trans purists that reject anyone that’s not medically transitioning….get over yourselves. If anything, you ought to be happy for all the new allies you gain. You need them.

    Second, trans is a label that most cis folks understand and are more likely to accept or at least tolerate. As a practical matter, this could save a relationship or keep you out of the hospital. There are still some cis folks that look negatively upon CD’s (transvestites) but understand transgenderism is a medical condition. Go figure.

    Whatever you decide to do, make sure your path defines the label you use….not the other way around.


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      Lauren Mugnaia 2 months ago

      Hi Emily, I completely agree with you. I’ve known I was trans almost forever, even when the word didn’t exist yet. I’ve been telling people I’m transgender for several years when I was purchasing things, even if I was in drab. I’ve never had a negative reaction but almost always positive and often it starts a conversation. Now that I’ve transitioned and presenting as Lauren, there are still moments where I know they’re suspicious so I will tell them I’m a trans woman, never had a problem so far. My medical card and my license both say I’m a female if they want to see ID.


      Ms. Lauren M

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        Emily Alt 2 months ago

        I guess I could say the same Lauren. Deep down, I’ve always wanted to be a girl. I’ve always been trans. It took decades to say that out loud. Feels good to say it now. Seems to be opening doors….as they say.

    • ' class='avatar avatar-100 photo' height='100' width='100' /> Author
      Sabrina MacTavish 2 months ago

      Great comments! I would like to wholeheartedly agree with what you’ve said. Yet… You also defined the reason for my trepidation, the class status between groups. It’s not just Trans or CD but even in what constitutes being a CD. It can get nasty going both ways. What usually happens are more specific labels to quantify, which I see as a reason to exclude rather than endorse. Anytime the broader base wishes to infringe (I use that word as it is most typical of the historical responses) on the smaller and perceived to be “more important” class tempers and war have broken out. I am neither condemning nor supporting here, just stating. Tolerance is something we demand and then try to withhold from others. If it’s good for us then by all means, come, join us. If it means giving up a particular benefit or recognition, then sorry, no way.

      This is where my quandary comes in. You stated part of my rationale that by adopting the “trans” label I open myself to better treatment (in many regards) and acceptance by the general public. Being a CD carries more negative perception (unless we include drag as being part of that larger label under crossdressing–plenty of arguments there, too). The issue, I believe, has deeper roots as every pocket of every potential grouping struggles and fights for equal rights. We have hate, and we have disregard for those who are not us. The question is, “Why?” Even in this life that I understand to be difficult, I’m still guilty of seeing others negatively and often shame myself for thinking so.

      So yes, I want us all to ditch unnecessary labels and come together respectfully and with acceptance, compassion, and understanding. And that includes me. Thanks for the insightful comments.

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    Lauren Mugnaia 2 months ago

    Hi Brina, You already know what my answer is… I KNOW I am a trans woman! How do I know that?
    That knowledge probably came planted in my brain before I was even born, because I’ve always known I was supposed to be a girl. I’ve always felt like one, thought like one, wished I was one, had the mannerisms of one, and my mother even gave me a girl’s name.
    I recently had somebody I know ask me; “How do you know you’re transgender?” My immediate response was: “How do you know you’re white?” He looked back at me with a ‘deer in the headlights look’, and I said, “exactly, you just do…”

    • ' class='avatar avatar-100 photo' height='100' width='100' /> Author
      Sabrina MacTavish 2 months ago

      I can certainly see that. That is one of my points as it pertains to me. I wish I had more certainty or could say, “I just do!” I’m not saying that either way comes without pitfalls; they both have obstacles that must be addressed. (I’ve always been good and shining those same headlights onto others…) Thanks for the response!

  6. ' class='avatar avatar-100 photo' height='100' width='100' /> Author
    Sabrina MacTavish 2 months ago

    Thanks for sharing your point of view. I agree. Our conditioning from childhood is much different than today’s children endure, although I will be careful here to suggest that it is better. There are many points I could make to both good and bad. In most cases, we are trying to teach tolerance, which is good. The world 100 years from now will look markedly different. We can only hope that being human is the only label one has to wear.

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    Kelly Blind 2 months ago

    Think if they, “society, politics, religion, culture, history,” were not the ones dictating what is or is not normal. Lets reverse that thought.

    I wonder how different the world would be if the LGBTQ community dictated to society, politics, religion, culture, history what is or is not normal.

    Now you have to ask yourself, how would I feel about who I am? or what I am?

    It is my belief that religion, all religion is what is wrong with the world. Religion is what has shape all societies, all politics, all culture, and history as we know it to be.

    Put all of that aside like the day you were born and just maybe there is an answer.

    Lets not let “They” guilt us into believing we aren’t “Normal,” as if “They” know what normal is. If “They” really knew what normal was there would only be one religion….”They” can’t even agree on that!

    • ' class='avatar avatar-100 photo' height='100' width='100' /> Author
      Sabrina MacTavish 2 months ago

      Great points! I appreciate the comments. Thanks!

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    Kim Dahlenbergen 2 months ago

    I’m right handed, 6’2”, blue eyed with white hair fits and betrays my age. These attributes are all obvious.

    What goes on between my ears is seldom shared with anyone else, and even when I do share my thoughts, these can be equally unclear to me and those I confide in.

    Its getting late in life. I know, so many say its never too late. But like you, I am just not sure. I think it may indeed be too late to expect a flash of clarity after six decades of uncertainty and self doubt. And you know, that is ok.

    • ' class='avatar avatar-100 photo' height='100' width='100' /> Author
      Sabrina MacTavish 2 months ago

      Thanks for commenting, Kim! I may never know and that is (mostly) ok. I’m at a point where I can move forward if I choose, and that at least takes some of the burdens away. It’s “Do I want to?” that is hard to answer.

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    JAKe Hatmacher 2 months ago

    I believe I liked and enjoyed your article about “how does one really know,” as I think I’ve mentioned before, even though I’m on hormonal therapy, I still occasionally ask the question of whether I should be doing it or not.
    I think, for me, your words about what society, and religion, and whatever dictate has always been a stumbling block for those that “don’t fit the mold.” Maybe we were born into a wonderful era of more acceptance. Not complete acceptance, but more acceptance, because as you and I both know, there are those who can’t get past fixed molds and into fluid ones. One can see that there are more and more people expressing who they are. This hasn’t just started. It has been happening for a long time, and just like women’s rights and the “ending” (in parentheses because there is much which still exists) of slavery, these events were the result of multiple individuals who were not content to have others dictate who and what they should be. In my mind, I’ve come in late to the game, the game being the determined struggle to express who we are and not be assigned a specific role or character based on our anatomy. Our ability to more easily step out in whatever clothing expresses ourselves has become much easier due to the bravery of those before us, and how thankful we all should be.
    I’ve thought for a very long time why it is that for many many years I just didn’t allow myself to express all my emotions or use words which really expressed how I felt. And it’s like you have said, we are conditioned by society. But as you know, some have expressed who they are with much more freedom than others, even as children, and to me that ability must come from the environment in which they were brought up in, an accepting environment where one’s spirit is allowed to accept itself and then express itself fully.
    (By the way, and this isn’t part of my comments above, I can’t seem to get to my article you edited to be able to add my own grammatical edits and then give you my okay to release it. I tried following your instructions but I can’t get where I need to go)
    Jeri (no longer in the Middleground)

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