Male Privilege

Recently I have received several very good in depth comments from Logan, a transgender man from the Medium writing platform I use.  From our communication I began to wonder how it would be to undertake a gender transition from the other side of the human binary. In other words , what does a transgender man go through to compete and/or thrive in a male world. Of course as I write this post, I am using a few stereotypes and biases because I can only speculate on the process. 

Years ago I actually went on a dinner date with a trans man. It was the first time I had been on a date with someone as my authentic self  so the first thing I remember is being scared to death. After all, I was building a new person from scratch.  But we aren’t writing about me. Through it all, he was the perfect gentleman and we remain friends to this day.

Other transgender men I have met have come through my dealings over the years with Trans Ohio which true to its name tries to provide statewide services throughout Ohio for the transgender community. My first observation was how well they presented as men. If I had not known, there would have been no way I would ever guessed their true birth gender.  Secondly they all seemed to be so well adjusted, the opposite from many of the transgender women I meet. Probably a topic for another blog post.

Here is where my pure speculation sets in. I would think using the men’s room early on would be as traumatic as it is for a novice transgender woman. Even though the great majority of men try to distance themselves from any communication in the “room.” 

For younger trans men, I am sure the parental adjustment is just as brutal. It is a special breed of parent such as my former hairdresser Theresa who adjusts to, loves unconditionally and raises a trans son. A lot of effort is needed.

I think also relationships may be easier for trans men to form, at least I know several who are in relationships with cis women. My thought is (and it is only a thought) it is because women are more sexually relaxed than men. Meaning, a hybrid transgender male person can be more appealing than a cis man.

What we can’t forget, male privilege comes with the potential of toxic male behavior which I haven’t seen from the transgender men I have known. Perhaps it is because they were never taught it growing up.

The whole process is so interesting but still so confusing to me. Perhaps Logan or someone else could shed some light on the process a transgender man goes through to survive in a man’s world. 

The Most Difficult Post

 Seemingly the Christmas Day post here in Cyrsti’s Condo would be one of the easier ones to write. But, it just isn’t. 

I know for many in the LGBTQ community the day brings back memories of ex-blood families who have rejected us. Of course I have documented many times  how my brother and his family did not support me when I came out to them as transgender. These days the extended family I have developed have more than replaced what I have lost from my brother. 

The bigger loss to me were the frenetic times I spent with my deceased wife whose favorite holiday by far was Christmas. All the memories now are so fond and bring back such great memories, it makes Christmas one of the more difficult times of the year for me too. As much as I try to make it as close to any other day as possible, I just don’t want to.

Even my daughter quit celebrating the Christmas holiday when she converted  to Judaism. This Christmas she is spending in Alaska with her kids on some sort of a glacier. That leaves just me, Liz and her son to feast on a holiday ham. As far as ham goes, we now have an embarrassment of riches. We bought one on our pickup from our main grocery store was shorted on our order. So it was deducted and we went down the street to another store and bought one. Then when we returned home and found the ham they shorted us. Finally, to make matters even more ridiculous, Liz was gifted a large ham or turkey from her company.   So either we have enough protein to last through June or we donate one of the hams to a local food pantry.

So much for our positive food issues. Let’s get to the important part of this post. I hope you all have a meaningful holiday, however you decide to celebrate it!

Twice the Man

 If you are like me, there have been many times in your life when you wished you could go back to a social situation you found yourself in and redo it. Often you have thought of a comment or reply which may have been more appropriate or even witty as a retort to a person who approached you. 

Seemingly as transgender women or transgender men we are more subjected to the possibility of a negative statement or gender comment. 

Today, I have decided to share Connie’s comment on how she handled a situation following a comment directed towards her:

”  You’ve reminded me on an incident, many years ago, when my wit was quick enough to make the perfect zinger. I was feeling every bit the woman I knew myself to be at a rather-formal gathering one night. A man approached me, I believe with full intent of chatting up a lady (I have always tried, as a woman, to be a lady). After a bit of small talk, including some obnoxious toxic male comments from him, my voice must have finally outed me. The guy suddenly remarked, “Wait, you used to be a MAN?” My quick retort was, “I used to be twice the man you’ll ever be, and now I’m twice the woman you could ever handle.” ūüôā

Nice! The worst I ever had to handle was a guy who was adamant about wearing my panties. We were kind of on a date which went quickly sour after that comment and was quickly brought to a halt. For his sake I hope he gathered up enough confidence to buy and wear his own panties.

Ironically (or not) I become a little agitated when a guy comes along with with strong male toxicity. Especially when he views transgender women as sex objects only. Then again he may feel the same way about all women, trans or not. 

I am also a bit humored when a novice transgender woman says how desperate she is to find a quality man. Just think of the dating pool she just entered with the number of cis women seeking that same man.

Bullied Kid Photo by Kat J on Unsplash

Connie was correct though. Once we transition, the possibility exists you can become twice the woman a man can handle if you have learned any gender lessons at all. The possibility of recognizing  male toxicity and steering clear of it is easier once you have lived it in a previous life. After all men aren’t shy of bullying other men as well as using other forms of gender dominance to get their way around other men. In many cases we did have to be twice the man as someone else just to survive.

Thanks for the comment!

What Makes a Woman

 This post actually began with a question which I saw asked in Facebook from one of my acquaintances who is starting down her own gender path. This isn’t an exact quote but essentially she asked what/when did we know we were women. 

Backtracking just a bit on the subject, I have never felt women were ever just made because they were born female. Both binary genders, male and female end up being socialized into men and women. Obviously, since I can’t birth a child or have monthly periods I prefer to refer to  myself as a woman of transgender experience.  In other words, I had to spend many years outwardly living as a man before I could finally take the plunge and begin  living as my authentic feminine self. 

These days also there are those who somehow want to suggest late transitioners  such as myself are not “transgender enough”. Mainly because we put off completing our gender transitions. There are several problems with that idea. The main one being, all the changes which have occurred over the years when transgender women and men are concerned. After all term “transgender” wasn’t even used until the mid 1960’s (according to my quick research). My gender dysphoria predates that by approximately twenty years. Of course too, I predate the internet and all the social media sites which have made more knowledge possible about all sorts of gender issues.

I am fond of using the term “gender fluid” as an example. If I go back to my teen and pre-teen years, I remember vividly  how many times I would wake up in the morning thinking which gender did I want to be today. I most certainly could have been described as gender fluid before I more clearly understood my true gender intentions. 

I also can not take all the credit for socializing myself into a woman of transgender experience. You may recall recently I wrote about my daughter’s role in setting me up in a very intense and scary appointment  at my first hair salon. I also have written about my two very close cis female friends who initially accepted me as a person and paved the way for me to socialize with them as a girlfriend. I love to say they taught me more about my new life than they would ever know. Before I met them, I never considered all the layers there were in a woman’s life which men didn’t have. They definitely helped me climb out of my closet but the person who kicked me out and slammed the door was Liz.

Liz (left) and I. Pre Covid
New Years Photo

Liz is my current partner and we have been together over ten years now. When we met, even though I was having success socializing my feminine self, I still was clinging to the slightest bit of male privilege and life I was leaving behind. 

She flat out told me she never saw any male in me and I should take whatever means necessary to get out of the closet (totally) and live full time as a woman.

So, I am far from being wise enough to tell or suggest to anyone what makes a woman. We are socialized by society to be confined to our own gender closets. How we escape makes us the women we are today.    

I Don’t Remember

I become  a little embarrassed when someone asks me when I started to transition into the transgender woman I am today. I just can’t say I don’t remember.

Photo Courtesy
Cyrsti Hart

I feel as if there are several answers which are too complex for the great majority of those who asked to follow. After all, they weren’t looking for an answer in a book length format. Even still the whole idea is something I should be able to explain in a simple blog post. Without having the person’s eyes cloud over in boredom as I explain.

Perhaps the easiest answer is I started to transition when I was born. However, since I didn’t really know what the problem was, did being born really count. The excuse is also to blame my Mom or her doctor for putting her on the meds which were so popular in the late 1940’s into the early 1950’s which (I think) flooded the womb with estrogen to prevent mis-carriages. Since my Mom had suffered several, the meds were prescribed. The drug was called “DES” and was a form of synthetic estrogen prescribed between 1940 and 1971 according to Google. The double edged sword of course was I may have not been born at all without the drug. I will take being transgender instead.

From birth until I was approximately 12 years old, I went through a phase of life I call “trans-interrupted” During that time I saw no way out of being a boy and indulged in all boy things such as sports and exploring the nearby woods to our house. 

So, I could say I started to transition when I noticed I still could fit into and try on some of my Mom’s clothes as I entered puberty. I like to say those adventures into femininity started me on a half century trip into cross dressing. It wasn’t until much later I finally figured out all that time I was actually cross dressing…as a man. It took awhile to transition myself away from it because I was so good at it and had established quite a bit of male privilege. 

Then again, I could say I began to transition the night I sat all alone and decided I couldn’t take all the ripping and tearing I was experiencing in myself any longer. All coming because of my developing gender dysphoria. The whole process led me to be extremely depressed all the way to attempted “self harm” as my therapist calls my suicide attempts. Finally I decided to follow the feelings I was having when I was exploring the world as my feminine self. In other words, I felt so natural. I finally got it through my thick noggin to do what was best for me. No matter how selfish it may seem to others in the world, I had to save me.

Lately, I have been taking the easy way out when someone asks me when I started to gender transition. I reply by saying I do remember. It was eleven years ago when I was 61 and decided to seek out whatever help I could find to begin hormone replacement therapy (HRT). The process was a way of telling myself there was no turning back as my life was changing for the better. Plus it’s a simple way (I think) of explaining to others where I am in my life. It helps me also to have my rusty memory working overtime to clear out the cobwebs.

You Reap what You Sow

Over the years here in Cyrsti’s Condo, precious few posts are dedicated to the transgender allies who aided so dramatically in my gender transition. One of the main contributors who I have mentioned is my only child…my daughter. 

As a child, I tried to do my part early in her life to be inclusive. I remember the days I scolded her on the back of the bicycle I rode her to school on. Particularly about how she was treating a boy who was getting bullied.

As she grew up, her mother (first wife) and I became divorced and moved apart. My wife stayed in Ohio while I moved to New York. We became separate but equal parents while my daughter remained the only child and was raised by a village. In other words, she was able to experience life in more than one situation.

All of this contributed to her becoming a determined confident woman with a stable marriage and three children. 

By now you are probably thinking how does any of this have to do with her becoming a steadfast LGBTQ ally with a transgender parent. It all mattered the day I came out to her. This is how it all worked out. I was extremely nervous of course when I invited her to lunch. I quickly told her why I invited her, I was transgender and would be starting hormone replacement therapy soon under a doctors supervision. 

What she said startled even me. She said “Did Mom and her Step Mom know?” I replied partially to both. My daughter only said “Why was she the last to know?” That was it. No rejection of any kind. Needless to say I was relieved because she was the last major person left for me to come out to as transgender. Everyone else who was near and dear to me had passed away except for my brother who is another not so pleasant experience. 

It just so happened also all of this happened near my birthday. As a wonderful gift my daughter offered to pay my way to her hair salon for my first ever color and style. At that point, I didn’t know to be more thrilled or scared. Of course I went for it and even have an “after” picture of the experience. (above)

Along the way, I paid many prices to go to the salon. First of all, I was accompanied by my daughter which made me even more nervous with the thought of her previous big brave Dad subjecting to her new self and going through all of this adventure. The second of which was cruel and unusual punishment it seemed. All because the salon was long and narrow and I had to walk through a gauntlet of women who had nothing to do but stare at me. 

After it was all over, I was proud of myself for passing another milestone in my path to woman-hood but I was more proud of my daughter’s acceptance of me. She gifted me a gigantic start down the pathway to being my authentic self.

Now, I share a rare acceptance from her family and even her extended family. Needless to say I cherish all of the gifts she has given me. Plus, I have lived long enough to see what I sowed so many years ago grow into such a strong transgender and LGBTQ ally.

Christmas Continues

This is a promised continuation of my Christmas adventure posts which furthered my confidence of surviving in a feminine world. I already have posted my shopping successes when I searched for gifts for my wife but this is a little different.

Actual photo of Clifton Mill


 At the time I was searching for things I had done as a man which I so badly wanted to do as a woman. I wondered how the whole experience would feel.

One place I gave quite a bit of thought to was a actual working flour mill in a nearby village which decorated heavily for Christmas every year

The mill and surrounding shops were normally well visited and were a great time to wear one of my in style heavy fuzzy sweaters with leggings and boots. Even though I still did have to fight off my anxiety by trying such a new idea, the excitement of finally being able to live my dream made up for it.

After I completed the fifteen mile trip to get there, the first thing I did (after I parked the car) was take a deep breath and tell myself to enjoy everything. Two things helped, the first of which was my wife again was working a closing shift and I managed to take the day off so time was not a problem. The second was it was a perfect winter evening. Chilly but not too cold so the deep breaths helped my anxiety quite a bit. 

As I began to notice, no one noticed me. I then summoned the courage to stop in one of the small shops and buy a cup of hot cocoa. Again I was treated with a smile and my courage was at an all time high. It was then time to buy a ticket and tour the mall grounds myself. As you can see by the picture, the mill itself is beautifully decorated. What you can’t see is the extra work they do with the surrounding grounds and out buildings. I was able to take my time and double enjoy my femininity as well as all of the decorations. I even bought a second cup of hot cocoa in the mill itself. Still, no negative feedback from anyone.

My disclaimer is I knowingly (or not) set myself up for success by doing several things. First of all, I had plenty of time to get ready and had the stylish clothes in my wardrobe to help me along. In fact my wife supported me enough that she had bought them for me as a gift. Second of all, as I have written, time was on my side. I didn’t have to rush and ruin this milestone moment in my life. Finally, I attempted it all under the cover of darkness. Which covers a lot of flaws. Even the places I purchased hot cocoa had soft lighting which in turn made me look softer also.

I know it is a selfish thought but the whole evening proved to be the best Christmas present I could have ever given to myself. Plus give me the confidence to continue my quest to locate and support my own femininity. It all felt so natural.

Christmas Lessons

I have been saving a couple posts for the time when we came nearer to the Christmas holiday itself. All of them involved me taking advantage of the opportunities to gift shop for my wife. Essentially, I was doing the wrong thing by sneaking out behind her back for all the right reasons by finding her just the right gift. 
It just so happened she was into vintage gardening items so any trip to an antique mall was a great start into finding her a gift. Routinely I used to cross dress as my authentic self and make the trip to local and regional antique malls. I was fortunate in back in those days I brought home a good wage so I had spendable income to come up with a great gift or two.

What did I learn? Essentially two things. The first of which was the basic dress to blend plus I had to leave the heels behind for comfort when I was heading to the antique malls. However, on occasion I did go to an upscale mall over in Columbus, Ohio to shop for a new garden gift in a couple of  specialty garden stores. In fact, I often broke my own heels and hose rules. In my own way I was dressing to blend as many other women were dressed in a similar way.


One night which stands out in my memory was the time I ventured out to buy my wife an oak bookcase to match the roll top desk we previously purchased. My wife was working a closing shift  in the bookstore she managed so I could know where she would be and till what time. .For whatever reason, I chose my black pantsuit, flats, long blond wig, along with my full length black coat.  

As I headed back to Columbus, Ohio for my purchase, I knew exactly where I was going but my anxiety level was still at an all time high because I was fearing how I would be treated. 

I wondered on the other hand how I would ever be able to load such a large object in the car by myself. Little did I know I had nothing to worry about because the store had two young guys ready, willing and able to load my purchase.

I was treated to a thank you mam’ and off I went with my purchase. I had to get it home before my wife returned from work. The trip took about a half hour one way and the best part was I was able to hide it in the garage away from prying eyes.

Maybe though, the best part was proving to myself I could exist successfully in a feminine world. Once again I had “survived” and could move forward again .

It turned out there were several other Christmas lessons to come.

Fun on a Bike?

Actually I didn’t have any fun with my imagined wig hair (back then) blowing in the wind plus having my hands wrapped tightly around my new crush’s waist. I was never able to beg my way into a ride and I never tried. I’m sure you remember the post I wrote about the experience. 

Long time Cyrsti’s Condo reader (and co-founder) Connie Malone does and commented:

” I’ve known you long enough that I recall discussing with you what to do about the biker guy at the time. It was fun girl talk, with lots of anticipation. Although it wasn’t a fairy tale ending, it still created much drama.

Photo Courtesy of
Connie Malone 

The banana thing never appealed to me (intended). I guess I’m penis- averse in general, and even more so concerning my own. I have been asked for dates a number of times, let alone the numerous hits I’ve had to endure – mostly on the unsavory side. I did meet with a fellow band member for dinner one night before a rehearsal, but it wasn’t really a date. He was just a really nice guy who totally accepted me when I came out to the band (a whole story in itself), and we met as friends. I remember sitting with him in the crowded restaurant, amazed that he was so comfortable being with a trans woman in public. Of course, it was fairly early in my transition, so I wasn’t really so comfortable being in public, myself. By all appearances, we must have been perceived to be on a date by others, and I was even more amazed that nobody was staring at us. It was one of those validating experiences that added to my confidence, at any rate.

Of course, having been faithfully married to my wife for 49 1/2 years has a lot to do with any choices I would make in the dating (or beyond) department.”


Thanks Connie for the comment. I say in essence she was the co founder here is because I was sharing coming out experiences with her and she suggested I write a blog. Back in those days, I didn’t even know what a blog was, so I had to research it.


In addition, I too had a couple dates with men who went out of their way to make me feel feminine. Outside of the sexual side of being with men, I tried to learn communication skills which would help me on a date. Naturally, I was scared to death but survived anyhow. One of the men in particular wasn’t from the area which I lived, so he was just passing through (as I hoped I was) when we went on a dinner date. The other I left up to him to contact me if he wanted to but he never did. Ironically, I was a regular in the two places we went and¬†received¬†great service and knowing looks from the servers I knew. My rule of thumb always was have a good attitude and tip well and it worked.


Speaking or writing about male crushes, I was pleasantly surprised to be able to watch one of my all time favorite male screen crushes on Turner Classic Movies. For some reason, I always have been fascinated with the WWII era and earlier and Robert Mitchum was my male crush way before I knew I was allowed to have one.

Robert Mitchum

Of course, any ideas of having a male crush were stifled and mis-understood. To the point I couldn’t even dream of him for fear of what was happening to me. It all makes sense now why I didn’t really crush on any famous cis women celebrities. Of course I wanted to look like them but did not desire them sexually.¬†¬†


It was all part of my gender puzzle I have written about in the recent past.
As far as motorcycles go, without a doubt I am sure Robert Mitchum would look great on one. Plus I am sure Connie was a suburb dinner date. As far as I am concerned, I was single during the dates I wrote about. So now I wouldn’t even consider such a move.


It’s always fun to consider the “what if’s” of life and how everything turned on a dime (or quarter).¬†

Brave…or Smart?

 Recently GB responded to a post I wrote concerning coming out as “bravery” Which in turn came from an Anna comment. Confused yet? Don’t be, here is the comment:

Unsplash image: Sharon 
McCutcheon

“Yes, I understand completely. How can it be bravery when we have no choice? And yet, coming from a typical social perspective, what we do as trans people is nothing but heroic, and yes, it is brave. Talk about strength. Trans people are the strongest people I know. When your core foundational identity is rocked as it is for all trans people, and you still manage to survive, sometimes thrive, it is a beautiful miracle.

And regarding your thoughts on giving up male privilege, I think there is a lot to explore here. I was with one of my longest female friends recently and we talked about white male privilege and what it meant to give that up as a trans person…and I have been wondering about this a lot as I meet people from different ages, races, creeds and seeing how they react to me…and what I am finding is that people who are oppressed are more encouraging to me on this journey than other white men..”

Thank you for the comment and I did neglect mentioning white privilege in the post. Indeed it is a huge part of what I was trying to write about. On the other hand, I don’t feel I am qualified to write about pressing racial issues because I did grow up and later lived with my white privilege. 

I did enjoy your comment which said “When your core foundational identity is rocked as it is for all transgender people, and you still survive, sometimes thrive, it is a beautiful miracle.” The only idea I could add is we transgender people are able to finally thrive is because we are finally able to live as our authentic selves. 

Giving up our white male privilege is but a small price to pay to be able to¬†achieve a gender transformation.¬†There are those who argue there are female¬†privileges’¬†also and I think the future is female but in the meantime there are still too many male¬†privileges’¬†such as¬†personal¬†security to consider. In fact, you could be the brave one if you don’t consider your surroundings when you begin to explore the feminine world for the first time. Just take the time to research the number of transgender violent assaults and use the numbers to be more careful.

Cis women have the benefit of growing up with the knowledge of not having personal security and learning to the best of their ability to deal with it. I have my own personal experiences of being in the wrong place at the wrong time when I was first entering the feminine world. I will share them at another time but to make a long story short, I escaped with no violence and I learned. 

Finally, I believe many white men are feeling the potential loss of their shallow male privileges and are more likely to be less into supporting other transgender women who have “joined the other other gender team.” Plus men are likely to have a more fragile idea of their sexuality and aren’t brave enough to experiment with change. 

I know I have covered quite a bit of ground with this post but bottom line is don’t confuse bravery with ignorance. Be careful, learn your lessons and build a new life.