Gender Puzzle

Anna commented on Medium concerning my coming out experiences as bravery.  I have never thought my gender transition as having anything to do with bravery. Rather, it was something I had to do. Now I look at the process as more of solving a gender puzzle.

Photo-Ryoji Iwata (Unsplash)

As I assembled my gender puzzle, I kept discovering more and more missing pieces. What happened  then was I needed to accomplish more and more in the public eye to prove I had it right. I have written in depth on many of my learning experiences all along with more and more I continue to discover as I follow this writing path.  Once I think I have it all figured out, something new comes along to prove I have not.

One thing I don’t write about enough are my severe bouts  with gender dysphoria. Perhaps there was a level of bravery to overcome passive and active suicide attempts. I know I was scared to death to enter the world as my feminine self on more occasions I can count. I have often told you all about all the times I came home crying following ill fated attempts at living as my authentic self. Back in those days I was still of the opinion I was crossdressing as a woman. When, actually all those years I had been cross dressing as a man.

I need to add in also I have never been good at puzzles. I tend to approach them (puzzles) with my usual impatience. When a certain outfit didn’t work instead of trying another, I allowed the mirror to lie to me and out I would go to fail again. Slowly I did learn not to force pieces of the puzzle together that didn’t fit. At that point, I discovered I could have success in public with my external feminine appearance and learned it was only the beginning. In other words, I discovered a whole new set of puzzle pieces. 

Now, even I wonder how I managed to navigate all of the challenges I was to face. It seemed every piece of the puzzle I located and was able to find a place for created the need for another. An example is how women communicate with each other. I found they have a unique way to communicate when men are present or when they are not. I had several women who protected me from possible negative situations with men as an example. It wasn’t just men though. Along the way I learned women specialized in passive aggression. Or where were the knives located when they met you. Those were the ones who said you looked good as a woman…for a man. (un said).

The biggest puzzle piece had to be what happened when I lost my male privilege’s. I reached the point of my life age wise when the term “sir” had been bestowed on me, if I wanted it or not. Most importantly I found my personal security changed drastically as I tried to live a feminine existence. For the first time in my life I asked friends for help getting to my car at night when it was parked in a relatively unlit parking lot. Overall, the loss of male privilege deserves it’s own post we will get to another time.

Over the space of life, I learned to respect my gender puzzle as just a extra special portion who I became as a human. After all, how many people get the chance to sample life from both sides of the gender spectrum.

I just hope I haven’t lost any pieces as I complete my puzzle.

Comments From You

First of all, a big WOW and thanks to all of you who took the time and effort to write in and comment on recent posts. The first  comes from Connie:

Photo courtesy Connie Malone

“So, I went out to grocery shop to get my booster vaccine. I was quite presentable in my hair, dress and makeup, and was feeling even a little pretty. At the grocery checkout, though, there was a discrepancy in the total, and it took three employees to figure it out. During their discussion, among themselves, I was referred to as “he” twice. I guess that answers any question as to my passing. It had been over two years (maybe three) since I was last mis-gendered, but the sting still hurts and kinda messes up my day. The employee who mis-gendered me had always been so friendly and accommodating in the numerous encounters we’d had in the past. 

The one thing that is common among cis people is that they don’t very often give their gender much thought at all. I have been getting myself to that point, as well, but it’s taken many years so far. As confident as I have become with myself, though, I guess I’ve not attained everything I’ve worked to achieve. 

The only positive here is that the hurt does not last as long as it used to. Big girl panties may not be enough; at my age, I should probably be in granny panties. I did get some redemption when the immunization coordinator at the drug store did not hesitate to check the female gender box on the form. The only bad thing about the experience there is that I ended up having a bad reaction to the booster, and I’ve been awfully sick for the past two days. Or, maybe it was the first experience at the grocery store that made me sick? :-(“

That is unfortunate! I think sometimes when I think I am most presentable is when I let my gender guard down and cis people mis-gender me. I am a strong believer in the “aura” a person gives off in everyday life. So in situations with strangers I try to remember to input feminine on them. Seems to work for me.

The second comment comes from Emily:

“I came upon your writings through Femulate. Really appreciate your acknowledgement that some of us pass most or all of the time.

Some sites claim that is impossible which causes a turn-off for newbies. It also indicates a lack of self confidence on the part of the author and/or laziness to do the work.Some of your other writings discuss friendships with women –I have found that most come around very quickly. Most men remain turned off”
Thanks Emily and welcome. Yes I have always thought the great majority of us can “pass” most of the time if they put a little work into doing it. What I mean is, take the time to learn a little of the feminine arts such as makeup and clothes. Maybe attempt to lose a little weight and strive for the closest possible shave. It’s never easy but is worth it. Others may not take into consideration the years of error and trial which went into being where we are today. 

Photo Courtesy Paula  

The third comment comes from Paula : The whole question of passing will never go away. Not even just in the trans world, I hear my gay friends talking about passing as straight, and friends with Asian heritage as passing as white. Does this mean it’s about claiming inherent privilege we are not entitled to?

On a personal level I am quite sure that I never pass, especially as soon as I open my mouth! Having said that the vast majority of the time I am not noticed, these days I have a self confidence I have NEVER had before, now I just go about my business as me and nobody notices. I fear it is when we try too hard that we get noticed and give ourselves away. It is only when I glam up that people notice, that I start to get the comment like “You’ve got great legs” with the unspoken “for a man”.

I suspect that the situation may be different here in the UK with very many staying with support groups long after their own transition, It is a sorrow to me that I will be missing two meetings in a row due to other, work commitments.
Thanks to you Paula. I agree once you can get to the point of being able to just live your life as your authentic self, most of the other pieces of the gender puzzle come together. Which could be a topic for another post!

We Got Mail

Image by Kelli Stinett

 I am sorry it has taken me so long to respond to several comments on my “Passing” post as well as others. I simply have been to busy this week to contribute much to Cyrsti’s Condo. So, in no particular order, here are several of the comments. Tomorrow I will add more.

Ironically, Georgette commented she was surprised by the lack of response:

“I was hoping to have some others comment on your reflections.

Back in the Dark Ages, The other TW I knew were much older than me, Age 23-27 vice their 50s-60s, Had never knowing any TM,

I can’t recall we called it Passing but was learning to just Blend in with other women in our age groups, Couldn’t really go stealth as my entire family has accepted me, And where I transitioned at the same place of work,

To go wherever women would be and see what they were wearing and how they conducted themselves,

I guess for me as a youngish woman I did have the advantage of youth,

For those older TW they just settled into a more comfortable look, Nowadays I see so many late-in-life still want to look like those younger women, I keep my opinions to myself as most don’t want advice just affirmation, I have been blocked or un-friended when giving some advice/criticism, Even here on Medium I was blocked with no reason given.

When I decided to come back out to this new LGBT+ world, I looked at a lot of women in their 60s and decided I didn’t want to look like them, My style is a more comfortable woman but still not ready to give up on being attractive, Most times people don’t believe me when I give my age as 71.

But sometimes I wonder if going back to be mostly stealth would be easier, In the General non-LGBT+ world I am.”

Thanks for the  comment. As you all can probably tell, the number of active commenters I get in relation to the overall number of hits I receive on the platforms I write on are in a small minority, which is fine. Back to the comment. Georgette, I am of the same age as you and do my best to dress to blend in with. Fortunately I lived through my attempts at not dressing age appropriate.  On the other hand, I try to make sure my minimal make up is properly done and my hair is brushed.  I think it is slightly humorous when my partner Liz always runs to put on makeup when I do when we go out. I tell her she wears makeup because she wants to and I wear it because I have to. 

Also Georgette’s comment comes from the Medium writing platform I post to. I’m humbled and flattered to have received an award from them as being one of their top LGBTQ writers. If  you are interested, go to Medium.com for details on their service. 

As I wrote, there is much more to this post coming up from Connie, Paula, Emily and more. Thanks for your patience.

Good Question

Recently I wrote a post concerning the term “passing” and it’s relevance to transgender women and/or cross dressers today.  Georgette wrote in with this response:

“I’m not sure the idea of “passing” will ever go away. I see so many on-line posts of Trans People still asking/worrying about it.  And it is not just transgender women, many younger trans men are asking the same.  The ones that give up and say they will never pass  say that’s OK as I will own being a transgender woman. But I wonder if they could pass would they still own being a trans woman.”


First of all, thanks for the comment. In my experience, most all of the transgender women I knew who readily passed, all went stealth and were never heard from again. Of course, my disclaimer is my examples came from “back in the day” when going stealth was the only way to go. In other words, stealth meant being invisible to the public than being anything other than a cis woman. 


I have two specific examples of trans women who closely followed each other in their transitions. In fact, I think their genital realignment surgeries came in the same year. Both of them had an advantage in that they had natural feminine tendencies and passed very easily. Yes, I was quite envious as I struggled to work with the qualities I did have to get by  Through it all, as I tried to come to grips with my gender identity, I was able to essentially “carve” out my own little niche. 


These days, I find myself  struggling with going stealth myself. In fact if the truth be known, I am an estimated  ninety per cent in the world as a cis woman. When I refer to this, I need to explain for the most part it has little to do with appearance and more to do with confidence. Much of my confidence comes from having Liz by myside. She has my back when/if anyone miss-pronouns me. Ironically, I think we get more public push back from those thinking we are lesbians. 


In addition, I have pulled back from most of my participation in the transgender – cross dresser support group I used to be fairly active in. I just don’t feel a part of it anymore. Being a full time participant in a feminine world has eliminated the need to get all dolled up to be with other like minded individuals.  If I truly thought I had anything to add, I would go. Many of the other attendee’s are much younger so there is an age gap to consider also.


Still,  I do think I carry the stigma with me of wanting to “pass” as a cis woman. Too much time , effort and worry went into during my gender transitional years. I can’t forget also how much the femininization affects of hormone replacement therapy helped me align my inner and outer selves. Finally I  learned none of it still matters totally. An example was the Thanksgiving debacle I went through with my daughter’s in laws. My excuse for their miss-gendering was how well I imprinted my maleness on them earlier in my life.


It’s a good question.

Feminine Socialization 201

Essentially this is a continuation of my recent post describing portions of my early feminine socialization. Included  in the post, I wrote about almost being included in a bachelorette party get together. I say almost because I was briefly invited then heard nothing more about it. I didn’t give it much more thought because the marriage only lasted approximately one week. 

The entire situation started when I expanded where I was going to socialize, or try to. If it sounds as if I was doing quite a bit of drinking during this period of my life, it was because I was. It is important to note I rarely drink alcohol at all now. Back then though I used it as a crutch in numerous ways. When I drank I was braver to go and try to socialize with others. To basically dive into the girls sandbox and see what happened. 

What happened was I found I was accepted into a small group of acquaintances who were socially interesting. Especially the exotic sister of one of the bartenders. She was truly exotic in that she was a dancer as well as being a hair stylist. This was in addition to her being a well tattooed dark haired beauty. To say I was envious is an understatement. She always threatened to work on my hair but I wasn’t sure how that would work back in those days when I was wearing a wig. It turned out it never really mattered. The rest of the group included me (the transgender woman) a lesbian, the bartender and her husband as well as others who drifted in and out. 

How I looked back then.

Very quickly it seemed our little group of acquaintances who gathered in the venue for drinks grew. Included in the group was a big teddy bear of a man who worked in a local lumber yard  and rode a classic Indian motorcycle. He fell in love with the exotic one and they decided to get married at the spur of the moment. Ironically, I think most of the group thought it was the wrong move to make. I know I did.

We all were right because the marriage only lasted one week. After it was over, it turned out my feminine socialization was to take another turn into new territory. I was becoming attracted to a man who was paying some sort of attention to me. It all started when the marriage had dissolved. The poor guy still kept coming into the venue and I thought was treated rather poorly by most of the group. I felt sorry for him and let him know. By knowing both of them the short time I did, I didn’t think the two were a match made in heaven. 

At any rate the group began to go in separate directions but I kept coming in the venue as did he. Surprisingly to me, he chose to sit next to me at the bar and all of the sudden I had the ultimate validation of a novice transgender woman…a man at my side. Especially a bearded one who rode a motorcycle. I always fantasized about how it would be to ride with him but never got the chance. Very quickly he took another job and moved away from the area.  

What did I learn? Even though I was having a difficult time being attracted to male companionship, I proved it wasn’t totally out of the question. Also knowing the lesbian in the group was my introduction into knowing anyone who identified as a cis gay female. 

Most importantly I gained another level of confidence. I found I could socialize with a diverse group of other people.

I had graduated to another level of life on my transgender path and it was looking more and more as if there was no turning back.    

The Good Old Days

 I have touched on the subject of my ex wife (the first one who is still alive) bringing up the story from my past when I wrecked a car. The wreck could have easily killed both my brother and I. My problem with my first wife was when she referred to me as “he” could have seriously injured both of us. It was one of those moments I wish I was quick enough to say something like “Yes HE did it but now HE is gone.”

In the grand scheme of things, the most I would have gotten out of her was a weak apology. As I began to think of it, the entire wreck was systematic of my life back in “The good old days.” In other words, the good old days weren’t so good. In addition to my gender dysphoria issues, I had the military draft hanging over my head for most of my high school days into college. 

During this time I was very self destructive. As soon as I became old enough to drive, it seemed trying to kill myself behind the wheel was the way to go. In fact I began to think I had a guardian angel riding with me when I was going to try something stupid.

Another problem with the good old days was I hadn’t been diagnosed as bi-polar yet. Once I was years later when I was honorably discharged from the Army, suddenly many of my unexplained depressive episodes were explained. In fact, the first relevant gender therapist I visited told me there was nothing I could do about my desire to cross dress as a woman but there was help available for my destructive mood swings. Her advice went a long way into explaining why I struggled so hard with my life.

I wish I could say the overall self destructive experiences I had in the good old days were over. In fact, the more I tried to not risk going out in public as a woman, the more I did it. By this time I had divorced my first wife and married my second. Little did I know I would be setting off on a twenty five year odyssey  which would include many peaks and valleys. 

Through it all, I managed to go on a frenetic job journey which matched my urge to out run my demons. We managed to live in such diverse places as the NYC metro area all the way to an extremely rural area of Southeastern Ohio. My demons were relentless though and of course trying to outrun them was a waste of time and energy. 

The good old days had become a blur except for the strides I was making in my feminine presentation. Many of which put me in direct conflict with my wife. She knew of my cross dressing urges before we were married. She never agreed with any ideas of me being transgender and naturally was afraid of me being discovered going out. Nothing was good enough for me and I ended up going out as my authentic self as much as possible behind her back.

All the lying I did made the good old days less than pleasurable but still I had to do it. It’s a shame such a time of discovery and learning in my life had to have such a unfortunate ending.

So, I guess the good old days weren’t so good after all. I’m just lucky I lived through them to experience my life now as a transgender woman. 

No Restrictions

Yesterday was one of our trips up north to Dayton, Ohio for what amounts to my daughter’s Thanksgiving get together. It actually is put together by her Mother in Law.  Since the family get together is not my first rodeo, I knew what to expect. Fortunately, I am nearly totally accepted by everyone. Including my first wife who I maintain a cordial relationship with. 

With the embarrassing spread of food and the holiday, both Liz and I called off the strict diet we have been strictly following. I called it short term pleasure because it will be so much harder to resume the diet which we have pledged to do after the left overs are gone. 

However, thanks to the diet I think I was able to present myself well in my boots, leggings and form fitting black blouse.  I was able to only be miss-gendered one and a half times during the long afternoon. The mother in law seems to always comes up with the infamous he…she comment. At least she corrects herself in mid sentence. Always. The other time came from my first wife when she was describing a wreck I had which nearly killed my brother and I. I just let that slide because she is a little ditzy. 

Then there were the grandkids who accept me totally. What a treasure! I have three. One of which is highly androgynous and is a sophomore at The Ohio State University who took an exceedingly rare football beating from rival Xichigan. 

On occasion there are pictures which surface later. If there are I will share them with you. 

Giving Thanks

For many in the United States Thanksgiving is a bittersweet holiday. Especially in the transgender community. I am an example.

Over the years my deceased wife hosted the family for a Thanksgiving feast. Our door was open also to my employees who may not have a family to celebrate with. To put it all in perspective, one big turkey was never enough. Through it all, after my parents passed away, my extended family was my brother, his two sons and the kids of theirs (and mine) who followed. We had a big house I was restoring so we had a large space to set up in and all were still welcome.

For the most part these were fond memories until I transitioned. By this time my wife had passed away and the dinner had moved to my brother’s house. Before I showed up as my authentic self for Thanksgiving, I called and talked to my brother. He said in essence he would always refer to me as my old self and he would get back with me concerning having an invitation at all. He never did and I never looked back. After all his in-laws were all right wing Southern Baptists. I guess he didn’t want to stand up for me.

As I said, I never looked back. I found myself firmly entrenched in my partner Liz’s family plus I was welcome in my accepting daughter’s extended family. 

I know so  many in the LGBTQ community aren’t so fortunate. Too  many are ostracized from their families and previous friends. Now it’s not uncommon to refer to other “non-blood” folks as new family.

Whatever it takes, I hope you all are able to take a moment and celebrate your blessings.

Happy Thanksgiving and thanks for stopping by Cyrsti’s Condo! I truly appreciate it.

Tennis Anyone?

This is another of my continuing series of posts revolving around chances I took cross dressing my way into becoming a transgender woman and living fulltime in a feminine world. 

In the restaurant/bar I used to manage, two cis women who I presumed were in their fifties, came in several days a week to enjoy a cocktail or two. During the warmer months they used to stop by after their tennis matches in their tennis outfits. Of course I was jealous of the fact I didn’t have an outfit to match theirs.

Around the point in time I am writing about, the stores I loved to shop in started to carry short thin ribbed flared dresses in larger sizes. Perfect to put together a tennis outfit. All I needed to do was find a white one. As luck would have it, I found one in my size. I then set out to complete my “outfit”. The problem I had was finding items and then hiding them from my wife. As luck would have it, we had a rarely visited other closet where I could hide an item. Often in plain sight. 

Now, back to the outfit. Finding a pair of white tennis shoes in my size actually proved to be fairly easy too. Now I had to figure out what to do about my legs. Even though I was able to shave my legs back then I added a pair of Leggs pantyhose and even added a pair of white thigh highs which didn’t exactly fit the idea of what a cis woman would wear with a tennis outfit but still added some pizzaz to the whole image. After all, I was reliving my non existent teen girl years I missed. 

I finished off the whole tennis image with my long straight blonde wig.

Let me add in here, I had rarely even touched a tennis racket in my life so I would be without one when I went out.  Once I was secure (the best I could) in my tennis woman outfit, I headed out to one of my favorite up scale malls. My wife was working that day so I had free time on my hands. Once I arrived at the mall, I was able to semi relax and feel the air on my legs and I found also I attracted quite a bit of attention from the older men who seemingly were there to supposedly walk but probably to look at women too. 

The whole situation was I equated being stared at as validation as a woman. I was  to learn later in life it was so wrong. There is a thin line between being classy and trashy when you are first cross dressing in public. I’m afraid I crossed the line into trashy in my early days of journeying into a feminine world. If my tennis outfit crossed into trashy I can’t tell you. It was so long ago.

My story is I was doing nothing different  than other cis women I had mentioned above. It was only another attempt to be just like them. 

Tennis was just an excuse.

When Life Gives You Lipstick

When life gives you lipstick, wear it!

Anyway you cut it, life is never fair for everyone. I’m biased but I think transgender women are dealt the most difficult hands in life. First of all, we have to do the difficult work of  figuring out who we are. Looking back I have written numerous times about all the mornings I woke up and immediately tried to figure out if I was a boy or a girl. What made matters worse was the fact this all happened before the internet and social media eras. Loneliness was extreme. I wasn’t old enough to understand all that was happening to me and there was no one to explain the meaning of being gender fluid.

In the meantime I did the best I could to survive. I even tried to “come out” to a friend in high school (a guy) and was roundly rejected. Looking back, I had a total girl crush on another friend which I never let on to. It seemed life had dealt me a hand I couldn’t win. 

Once I turned driving age though, I did get a small break.  On a couple occasions I was able to cross dress and sneak out of the house when my parents were away. I remember the trepidation I felt when I saw my reflection for the first time in a store’s shopping center window. On the other hand, I felt a bigger sense of accomplishment. Other than those extremely rare occasions, high school wasa continuation of my gender frustration. The only relief I felt were a couple of school events I went to which featured a couple of very presentable boys in drag. Needless to say I was very jealous. 

The biggest setback I thought was coming was being drafted into the military. Along with the obvious reasons to dislike my upcoming service was the fact that women didn’t have to worry at all about the military. Ironically this all turned out to be the time when life gave me a potential set back and I was able to turn it all around for the better. First of all I was given very little chance of  continuing my career as a radio disc jockey in the Army and I did just that in the American Forces Radio and Television Service. Then perhaps more importantly, I was able to finally come out of the closet toa few of my closest friends as a transvestite. Finally, the gift which kept on giving was meeting the woman who would turn out to be my first wife and birthed my beloved accepting daughter. 

Even with all those successes, I was still missing a huge gap in my life. Something was still wrong. Around this time life gave me the transgender term and the internet to research it. .All of a sudden I knew who I was. All those times I went to the transvestite mixers and didn’t quite fit in made sense.

It all left me with the huge “what if” questions. Life had given me the answer to my gender issues but also left me the choices to settle my problems. Was I going to take the chances to give up all my male privileges and live full time as a transgender woman. After years of experimentation and soul searching the answer became clear and I took the gender plunge. 

At this point life gave me options. When my wife passed away, she was my biggest naysayer, so tragedy turned to a bittersweet triumph. Around this time also, the Veterans Administration began offering Hormone Replacement Therapy which I could take advantage of at a very low cost and I was old enough I could take advantage of early Social Security retirement and not have to worry about coming out at work.

It turned out life was repaying me for all the years of  turmoil and stress it put me through.