Showing posts with label cis men. Show all posts
Showing posts with label cis men. Show all posts

Tuesday, August 18, 2026

Try then Try Again

 

Early Days in my Gender Closet
JJ Hart.


When I first broke out of my gender closet and into the world, there were many cases of failure I needed to deal with.

For example, all the evenings in malls when I was singled out for abuse by groups of teenaged girls. So much so that I tried my best to head to the other side of the mall as quickly as I could in my new high heels before the girls noticed me and started laughing.  When that happened, many times I was sent home in tears wondering what I had done wrong with my presentation. One thing was for sure, I needed to go back to my cross-dressing drawing board and try, try again.

It took me a while to realize I was backwards in my public presentation thinking. I was dressing myself how a man would rather than how a ciswoman would if I stood any chance of blending in and making it in a world I only had just dreamed of. Plus, I benefitted from a crash diet I put myself on which helped me to fit into more stylish feminine clothes. It was the first time in my life that I had been so serious about anything that I could remember.

One big thing I did not realize was the total scope of the male to female femininization project I was taking on. The deeper I delved into the feminine culture I was in, the more I found I had to try to do to become successful and there were many times when I simply not a success. One time that sticks out in my mind was when I visited my gender therapist unannounced as my authentic self and sent her into obvious shock looking around to find out where her son was. I would have thought, since she advertised herself as a gender therapist, she would have been more comfortable around a person cross-dressed as themselves. But she was not. I took it as I had to keep on working on my feminine presentation to hide all the testosterone poisoning male puberty had wrecked my body with.

The more I was able to find myself behind the gender curtain as a transgender woman, the more I needed to try, try again to never stop learning more about how ciswomen spend their lives operating in the world. The circles they run in and their overall dealings with each other as well as men come to mind as I think back on my initial experiences. It was a scary yet exciting time in my life as much of the time I was still risking destroying life as I knew it, if the world discovered my deep dark secret. I had not yet concluded my secret really was that I was a woman hiding behind a man. Not the way I was living thinking I was a man trying to be a woman.

Most of the time, the world did ignore me as my presentation improved well enough to get me by but on the occasions I met the rare TERF (radical feminist) gatekeeper who did not want me behind the gender curtain, I was sent away to try, try again until I earned my way into the places I wanted to go mainly such as women’s restrooms because on my long days out I simply needed to go to the bathroom and not make it such a big deal. It took me a lot of resilience and knowledge of the feminine world to do it but I finally earned my way into the “room” also.

I have always thought that building my fragile confidence into a strong one was one of the best moves I ever made so I could relax in the world and stop trying so hard to be myself. I say fragile because there were so many times over the years when I thought I had achieved confidence only to have it shattered by an unfeeling gender bigot. By trying again and again to overcome the haters, I made it to a point where I could say to heck with them and I was going to live my own life the way I saw fit.  

When I had reached a point where I thought I had enough confidence to get me by was when something unexpected happened to challenge my path. All along, I had some sort of an idea of how complex a ciswomen’s life was than a man’s life, but until I got there as a trans woman, I did not have a real idea of how complex. It was as if every time I thought I could see a clear road ahead on my gender path, someone would throw a stop sign in my way. Making me stop what I was doing and look around. Did I really want to take all these difficult steps I was taking to be a transfeminine person after all.

Of course, once I stopped, looked around and thought about it, I discovered I was in the world which I had always belonged to and I wanted to stay in the worst way. The more I was allowed to play in the girls’ sandbox, the more natural I felt as I felt my life make a seismic shift towards becoming the person I had always meant to be. To keep trying, I needed to decide to risk losing all my remaining close friends, family and employment and embark on the road without any more stop signs.

I was not getting any younger and at the age of sixty my transgender biological clock was running out. It was time to try to see if I was still healthy enough to be approved by a doctor for gender affirming hormones or HRT and I was. Which was actually the last big gender hurdle I had to try because I had already done the social part and I did not desire any extensive facial or genital realignment surgeries. So, I could then try to discover if I could find anyone to share my unique life with.

By trying to put myself out there on dating sites and in the regular straight venues I was going to, that paid off for me too when a ciswoman lesbian from nearby Cincinnati responded to one of my on-line dating requests and we are still together fourteen years later.

All those early years of trying and failing came back to help me years later when I needed it most and my life went full circle.

Thanks for reading along and passing along all your comments and reactions! I really appreciate hearing from you.

 

 

Monday, August 3, 2026

Letting Tomorrow take care Of Itself as a Transgender Woman

 

Image from Valentina Conde
on UnSplash.

Since I was always a person who had a difficult time living in the present, tomorrow always loomed large in my mind.

I think it all started when I began to rebel against the masculine world I was being forced to live in and always thought tomorrow could be better. It turned out that all the wishing and hoping I did for a better tomorrow turned out to be wasted time and energy, I finally needed to take matters into my own hands, stay in the present and do something about me being stuck in my dark, restrictive, gender closet with only a mirror to help me.

It took a quantum shift of thinking on my part to even thinking about how I could change my life. First of all, it was nearly impossible for me to quit daydreaming about the next time I could cross-dress in my mom’s clothes and try on her makeup. Any time I was not actively being engaged in male activities, I was hoping that soon I would be glimpsing a view of me in a favorite miniskirt I had found by accident at school outside of the girl’s locker room. If the girl who left it behind did not want it, I certainly did before a janitor found it and threw it in the trash. I was overjoyed to add it to my small but growing feminine wardrobe at home. Hopefully away from any prying eyes who may find it.

Somehow, I managed to hide my “treasures” away and add to them with my own meager funds I had earned from my rural newspaper route and from chores I was doing around the house. I will never forget the excitement I felt when I found a pair of women’s shoes that fit me in the department store where I was sneaking in to buy my makeup and panty hose. The whole process made me feel good because for once I was not relying on anyone else to help my cross-dressing along. It all was just me, and I was in the present doing it.

As I moved along in years and experience, I increasingly wanted to break out of my dark closet to see if I could exist in the world, in the present for once as the person I was coming to believe could be my true self. I learned the hard way that the public would not be as forgiving as much as my mirror was as I was treated quite rudely the first several times I went out. Even in places I should have had no problems in such as the big shopping malls back when they were popular. I couldn’t seem to dodge the giggles and stares I got from the teen girls before I learned to stay in the present, be who I was and begin to blend in with the group of other ciswomen in the mall. I learned the hard way to dress for them and not rely on some sort of trashy look that appealed to men. Which was getting me clocked as a man in drag every time.

All this new reality was teaching me I could indeed enjoy the present when I was out in the world. But not enough to keep me there when I was back in my unwanted male world. I have always wished I could get back just a portion of the time I wasted daydreaming of how it would be if I was the only ciswoman in a business meeting I was in. I know I could have been more effective…if I could have been accepted. Which I would not discover how difficult that would be until I got out further in the world as a transgender woman. I will always remember how I was shunned by a small group of men I somehow became involved in a discussion with when I first came out of my shell. Quickly I discovered, as a woman among cismen, I would have to fight for my right to be heard on an equal basis.

The more I was out in the world, the more I was forced to stay in the present. If I did not, I could find myself slipping back into old male habits which would give my past away much sooner. Such as not employing my old “stay away” male scowl and replacing it with a much more pleasant feminine look which said I was happy to be here. Which got me by. Other areas of just being a woman I needed to concentrate on was how I moved around in the world when I was still trying to juggle being in both worlds of male and female. One day I needed to be feminine, and the next masculine ended up taking a real toll on my mental health as I did not know somedays what present I was supposed to be in.

Plus, the one aspect of being in the now as a transgender woman was the one I always mention, communication. As I was blissfully (sometimes) going along my gender path, suddenly more and more ciswomen wanted to know about me and were curious why I would be in their world. I was totally blindsided when I needed to start and participate in entire conversations with other women who appeared in my world. I discovered communication went way past just how my voice sounded into exactly what I was saying and how fast I could pick up two uniquely feminine communication aspects. Non-verbal communication and passive aggressive behavior. The normal ciswomen who interacted with me ended up using all their skills to size me up and often it turned into quite the contest that I needed to stay on my toes to get through.

Eventually, surviving all the gender wars I went through, made me a better, more well-rounded trans woman who could hold her own in the world. Primarily because I had built up the confidence to do it, and it became my number one accessory. So, what if my makeup or walk wasn’t exactly correct, I knew who I was and it showed. There was no blood in my water for the human sharks around me to come after.

All those years of trying to get into my present and stay there finally paid off for me, but only after I had paid all my dues.

 

 

 

 

 

Friday, July 31, 2026

When There is No One to Believe in You

 

JJ Hart

Sadly, transgender women and transgender men spend much of their lives being lonely with no one left to believe in them.

When it happens, the dark lonely closet you have been dealing with becomes even more restrictive and uncertain. With me, the only thing that kept me focused on my gender path was a little voice which kept telling me that against all odds, I was doing the right thing.

Maybe, like some of you, I had the same misgivings of what I was doing as I cross-dressed as a girl. Was I going through a phase, a fetish or was something wrong with me mentally all entered my mind one time or another. I did know, I had very few male friends and for some reason felt uncertain around the ones I did meet. Which only added to my loneliness and made me withdraw further within myself. It was very difficult for me to believe anything about myself during this portion of my life. But I thought I had no choice but to struggle on.

It was not until much later that I found that I did not have to struggle as much as I was doing as ironically, both sides of my dual gendered personality were coming out of their shells slowly at the same time. After military service in the Army, I learned to not be afraid of other competition from men, while at the same time I was learning how to exist in a ciswoman’s world I had always dreamed of. Life as I knew it was becoming unbelievably complex as I tried to balance two genders mentally and physically.  Every day, I needed to concentrate on who I was going to be when I faced the public. Ironically, I needed more room in my closet to make room for marriages, kids and employment.

Even when all of this was going on, I still felt lonely and wondered what I was doing wrong with my life. The problem was I was living backwards, which I would not understand until much later in my life sadly. The basics did not come to me that I was not a man trying to be a woman but was a woman trying not to be a man. It all comes under the old saying “If I had known then, what I know now, what a better life I would have had.” But the fact remained I was still living a very shallow life as a novice transgender woman and had so much to learn before I could claim my own version of womanhood.

For the longest time, I just took for granted I would just be lonely as a part of life I would have to get used to. Especially after my second wife of twenty-five years unexpectedly passed away from a massive heart attack. Even though she did not accept me as a trans woman, somehow, we still did stay together until the end. At least, I loved her deeply and was never lonely with her, or so I thought.

I found you do not miss what you had until it is gone, and death is the ultimate version of being gone and starting all over for me at the age of fifty-five was not going to be easy. Even though the relationships I had built up as a man were very few, what I had were all starting to die also. Any relationships with ciswomen as a man that I had were few and far between because I was not sure which direction I would go with my gender. I did not want to start another relationship with a woman just to end it by telling her she was actually living with another woman. As the gays would say, I was keeping my true self on the “downlow” the best that I could.

What happened next was that I was increasingly having a difficult time staying on the “downlow” because of all the explorations I was doing in the straight world I was trying to re-enter. This time as a transfeminine person. I was slowly building social relationships in the world with ciswomen who suddenly showed an interest in me. The problem I had was I was still not on HRT yet and was still in my mind too fake to pursue a relationship with a woman when after I stripped down to my basics, I was still a man without my fake hair, breasts and hips. Even with all the social stimulus I was receiving in my new world, I was still frustrated and feeling alone in my life.

I finally realized that I was the only one holding myself back from learning if I could be approved for gender affirming hormones or HRT.  I made the medical appointment from a doctor’s ad I had seen in a local LGBTQ publication and before I knew it, I was deemed healthy enough to be approved. It was a major step in my life and one I did not take lightly. The first night I took the minimum dosage of estradiol and spiro pills I was prescribed, I saved the special occasion for when my future wife Liz could join me in a venue in Dayton, Ohio.

Very soon, my HRT dosage was increased, and I ended up calling them my “magic pills” before I was switched to patches which would be easier on my system. Thanks to Liz and a few other ciswomen friends, I was able to think about forming deeper relationships with women again. My body had morphed into a curious gender blend of breasts, hips, soft skin with a non-performing male piece of equipment which did not seem to matter to the ciswomen around me who were not as insecure with their sexuality as most of the cismen that I knew.

Most importantly, I gained the confidence to believe in myself, which led me to not suffer the extreme loneliness I had felt during many parts of my life. It was like I was on a wheel, and my life had had the time and good fortune to come around again.

Hey all!!!! Thanks for reading.  Your input makes it all worthwhile to me.

 

 

 

Wednesday, July 15, 2026

Existing in a Male World from the Perspective of a Trans Man

Image from Nicola Dowie
on UnSplash. 
 


In response to yesterday's post praising transgender men, I received a comment from “Gio”, a trans man who follows my writings and thoughts.

Here is his comment word for word on what he has gone through during his transition from female to male:

Thank you JJ for this nod. You know, they are a tough bunch, on the exterior. They are also exhausting. Try to teach them how to be a real gentleman and right out of the gate they label you a sissy. I always counter with being raised to respect and honor women. In the Italian Culture in which I was raised the women were savvy. The women in my family ran the show and they somehow left the men feeling like they were in charge. I witnessed this with my parents (first generation born in America) and my grandparents (immigrants - who escaped Mussolini; everything old becomes new again but that's another story). The Cis men I encounter, many of whom are wealthy Trump supporters, posit they own their women. She is to do what they say. A woman, if raped, deserved it because of how they acted or what they wore. It boggles my mind. So, I remind them that women are to be revered, they remain underpaid yet they have more talent than their male counterparts. I remind them that if married they took a vow to cherish and protect their wives. I could go on and on here. Suffice to say, it’s usually a bipartisan type of conversation and they often end pleasantly. Luckily, I've not been fired yet because mostly these are the people who keep me employed. I'm also amused by how they request me as their chauffeur to drive their wives and daughters. It's these little things that cause a ripple effect”. First of all, “Gio” thanks for the comment!

I really liked your insight into how exhausting men are because on the few times I went out with a man, I could not relax and be myself when I was catering to his ego. In my family growing up, we were a heavily male influenced crew but like you, mom ran the show from behind the scenes, so I learned a lot from her on how to be a woman, She is rolling over in her grave as we speak to hear of such a thing but it is true.

Fortunately, since I am retired, I don’t have to worry about working with any tRumpters and their backward gender ideas. But when I was employed, I always did my best to protect and advance the careers of the ciswomen around me. To the point of even hiring a transgender server at one of the restaurants I worked at. Sadly, I was transferred and she was fired by the next manager, but I tried to do my part.

Looking back, it was my love of sports and military service which kept me from wearing the “Sissy” tag early in my life and when I advanced as far as I did up the business ladder I was in, I understood that males form teams and I was able to benefit from that even though I detested everything I was doing most of the time when I needed to play the gender game I was in. Maybe the whole time, I was exhausted too about playing the male game and just wanted out to go to my transfeminine world. I took what my mom taught (more than dad) and was able to beat the system which was stacked against me.

When we are transgender, it is certainly a complicated world we live in when we need to go outside the confines of a so-called normal world. The old world is on its way out and hopefully a younger more progressive gender-neutral generation will power a better world. Especially for transgender men such as “Gio” who was kind enough to share his thoughts with us on his world.

 

Tuesday, July 14, 2026

In Praise of Transgender Men

 

Image from Aiden Craver
on UnSplash. 

I am fairly certain that this is the first time I have written a post which almost exclusively deals with transgender men and how they relate to trans women. But it is long overdue as I know I have several transmen who join me on occasion and read along.

Plus, they are kind enough to comment on my writing to give me an idea of what life is all about from the other side of the major transgender border. Sometimes I even have a hard time remembering what the time was like when I was struggling to be a man, so I can understand and comment back.

My actual dealing with trans men goes back to my first dinner date as a transfeminine person. At the time, the person who asked me out identified as a super butch lesbian who had not yet decided completely to live a male life. We went to dinner at TGIF Fridays and yes I was scared to be on my first date as he reminded me of later. It was the first time I was not in complete control (or thought I was) for a date and I got to see life through a whole different viewpoint.

To this day, I still follow his social media to see what he is up to and on very rare occasions in the past, he included me in some of his observations which happened when he transitioned from the other side.

It turns out, many of the same obstacles of crossing the gender border are the same but just reversed of course. Such as the problem of suddenly using the opposite restroom that you were used to using. I wondered what the shift was like from a brand-new male viewpoint when you were expected not to make any eye contact with another guy in “the room”. You were there for one reason only, and that was not to socialize, do your business and get out. Then there is the problem of having to use the stall to pee and having another guy hear you do it. As we all know, cismen have a very fragile sexuality which could be challenged unknowingly at any time when you play behind the gender curtain from female to male.

Not so long ago, I received a comment from a trans guy named “Omey” who said he was not accepted much anymore by the girls he used to know but I would think leaving the girls club would not be dealt with so harshly as leaving the men’s club is for transgender women. I know the club house door was slammed shut on me quickly when I left the men’s club for good. Again, it goes back to a man’s basic lack of belief in his sexuality. I found ciswomen did not care as much that I was living in their world as much as men resented me leaving theirs. And I wonder what transgender men face as a challenge from other men as they try to break into the “team.” Because, like the rest of us, they have no gender workbook to work from.

I know I am forgetting many of the details that went into being a successful cisman for me such as the one-on-one confrontations I had with other men. I was fortunate in that I had built up enough male privilege to get by. Basically, other men could not challenge me at work because I was the boss and could fire them. Even though that was always my last resort. I also found that men are more effective when they build teams and women when they are allowed to form cliques behind alpha-females. Which I know is a stereotype but a successful one for me.

Then there is the argument who has an easier route to passing in the world as their chosen gender, trans men or trans women. I am biased, but I think trans men have an easier time of transitioning into the public once testosterone has a chance to take hold of their body. It is the reason we see so many transgender men later in life with male pattern baldness. Before the baldness sets in, trans men also have the benefit of a good haircut which can make them appear more masculine where transgender women usually must wear wigs because their baldness has set in already.

The more intrusive cosmetic operations from both sides of the gender spectrum are pretty much a give and take in my opinion. Trans women can’t wait to grow their own breasts through HRT while trans men want to go through the traumatic operation to rid themselves of theirs. It’s all a matter of which side of the spectrum you are on, but trans women are more apt to go through more severe facial femininization surgeries to rid themselves of their testosterone poisoned male features. Not to mention the incredible expense most must go through to do it.

My praise goes out to the transgender men who can bring the best examples of the feminine culture with them. Such as deep love and understanding and applying it to a masculine world which desperately needs improving. There are far too many toxic males running around these days. I know early on I benefitted from the understanding of trans men and found them to be so much more intellectually stimulating than cismen and their drama. That is why I so enjoy hearing from trans men, ciswomen and the rest of you on a regular basis.

I am sure, no matter where you end up as a trans man or transgender woman, you are more than happy to give up your place in your old gender world to anyone who wants it. We just need to be allowed to take the best of both worlds and build a better one from it.

Thanks again to all of you who read along and even take the time to contribute to my writing! I’m sure in this post I have skimmed over many of the obstacles transgender men face, and I just hope I flipped my usual script and mentioned a few.

 

 

Tuesday, July 14, 2015

The Science of Bra's


Think of it-which item of clothing generates more discussion than a bra. Often, the discussion is cute and nostalgic, embarrassing or even fetishistic in nature. Or Not!  For those of us who had/have a history of dating generic girls, there are the terrible memories of trying to slyly "unlock" the mysteries of removing our dates bra's at the drive in theater (Imagine what she felt?) Then, there were the wonderful girls who could "effortlessly" take their bras off-under a sweat shirt. 


Of course as time has passed and I have learned the gender grass on the other side is NOT necessarily always greener. Many of the women I know don't speak fondly of the first trips with Mom to pick out a training bra. Plus, there is the pressure to buy the right lingerie set (including a bra) for an intimate date night. (Or the possibility of one.)

Cis Model Lace Bra

And, of course there is more- so much more. If and when you decide to explore HRT and develop your own breasts, then all of a sudden you are slightly embarrassed teen girl looking for her first real bra.



Finally, I know I'm writing to the choir here about the power of the right bra. No pun intended, but the right one can "push" you to heights you never imagined. T-shirt bras can smooth you under a form fitting top or a flirty "peek a boo" lace bra can give you just a touch of class when you need it (not all low like me!)

I could go on and on. For some bra's are a BIG topic and for others (me) not so big. I can only say I have had a whole different idea of what's going on under my external clothing recently. I was more than a little shocked the first time I was told by one of my doctors to take my top off-then my bra. (Yes Mom-my undies were clean!!)

It's not a real surprise that bra's are such a big deal because they hold breasts (real or other wise.) And, we all know the power of the "girls" on both genders. Transgender, cross dresser, cis man or woman- all are influenced by breasts.

Even when I was wearing breast forms exclusively, somehow they defined my femininity.  Big or small, shaped well or not-bra's have a big job to do with all the boobs running around!

Wednesday, May 20, 2015

Lost in "Trans" Trendy?

In the midst of all the circus transgender hoopla around all of Bruce Jenner's "coming out", other stories fall to the side so to speak. 

One of those has been on going on a venerable American "soap opera" "The Bold and the Beautiful." I am going to take the easy way out and pick up the TransGriot Blog post:

"Rick and Trans Maya"
"Yesterday Maya Avant told her boyfriend Rick Forrester on the CBS soap 'The Bold and the Beautiful that she is trans.

Rick didn't take the news well initially, but when Maya was about to walk out of the door of that Big Bear cabin and out of his life forever with her heart breaking in the process, Rick once again declared his love for her."

Monica from TransGriot then takes a fascinating look into yet another key issue in the transgender community-the romantic attraction of cis-men to trans women.  Over the years, we have done multiple posts about it here in Cyrsti's Condo. If you don't know- Monica is never shy about her thoughts and words especially when trans women of color are involved!

Here is how she finished the post:

"We need to have an ongoing conversation about our relationships in which the baseline for having it is that our femininity as trans women is not erased and the cis men who prefer us as their partners are not demonized for doing so. 

The cis men who love us are going to have to step up and meet us trans women halfway.  They are going to have to come out of the shadows and say in no uncertain terms they love us, we are the women they want to marry, and to kiss their behinds if you don't like it.   

If a soap opera story line can lead to an enlightened conversation about a real world issue, then by all means lets get that conversation started."

Here is your link for more!

Try then Try Again

  Early Days in my Gender Closet JJ Hart. When I first broke out of my gender closet and into the world, there were many cases of failure I...