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.

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?”

En Femme Style

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.

Crossdresser Superstore

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…


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Sabrina (Brina) MacTavish

Brina is from Iowa. She is currently the Managing Editor of CDH and TGH. When she isn't busy on-site, she spends her time writing--more than a hobby, but still seeking that 1st bestseller. Under her male guise, she has 5 published works of fiction and one short novella under Brina's deplume. A recently completed CD novel should be ready in the next year and Brina hopes it can become a series with fun characters.

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Rochelle Mills
Active Member
1 year ago

Brina, appreciate so much for your feminine wisdom–I can relate! Even when we can’t see and hear each other in person, we recognize and validate each other here virtually. Always have appreciated your warmth and expressions of your inner truth, as murky as they may feel at times. Many of us live with some regret, often based on the lack of positive frames of reference when we were younger. Where were the genderfluid/CD/trans femme sisters when I was younger? More in the closet then than now, I suppose… I hope to nurture and better express the compassionate woman inside me.… Read more »

Jennifer Friendly
Active Member
3 months ago
Reply to  Rochelle Mills

Where were the gender fluid sisters back when we were younger? Same place we were, hiding deep in the closet, afraid, and rightfully so. We tend to judge, others and ourselves, based on what’s happening today, but it wasn’t that way. No internet, we didn’t even have a TV until I was 10 and then there were all of 2 channels, which signed off at midnight. While there were probably many of us, no one could talk about it, much less reveal ourselves without risking physical harm. This fear, and the hiding, continued all our lives, it even permeates here… Read more »

Belinda Wilson
3 months ago

 I struggled with this question 10 or so years ago. No answers were coming so I went down the path to see what was there. HRT was prescribed and 1 course of patches had an effect resulting in my 70 year old silver hair going dark again breasts going to small B for the left and A for the right.  I loved the changes but after a while keeping up the grooming negative reactions from some of my work contacts and also at a major project I had , became a bit of a burden. I was still presenting in… Read more »

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