Showing posts with label life lessons. Show all posts
Showing posts with label life lessons. Show all posts

Sunday, March 8, 2026

When Gender Calls

 

Image from Brooke Cagel on UnSplash. 

When I was very young, when I listened closely, I could hear the faint sound of my true gender calling me.

Please keep in mind that very early on I could not quite understand what the voice was trying to tell me. I just knew something was not right. As I grew older and started experimenting with Mom’s clothes (even to the point of shaving my legs), did I have a basic understanding of what the voice was trying to tell me. From the first view of myself in our full-length hallway mirror, I had an idea that I had arrived in the right place as I stared at the pretty girl that I had a hand in creating.

It was then that the real gender work began. The first problem I had was trying to find the private time I had to cross-dress. And once I did, when would I have the time to do it again as the gender pressure built on me every time. What I did not understand and wouldn’t for many years was that I was much more than someone who just wanted to wear pretty feminine clothing. My true gender was calling and would never be satisfied until it was properly expressed. Even though I did not fully understand the path I was on and would have to accept it over the years to come. Especially all the blind curves and stop signs I ran into. I was not prepared for all the trials and tribulations I would have to go through to even try to pursue my gender dreams which always had to do with living a transfeminine life. At that time, the phrase had not yet been invented or used, so all I knew was I wanted to be a woman with all the perceived benefits which came with it.

Jumping ahead, the benefits of living as a full-time trans woman were there but just vastly different that I thought they would be. I still had the joy of selecting and wearing pretty clothes which changed with the seasons. It turned out, some of the enjoyment was taken away when I needed to pick out an outfit every day when I gave away all my male clothes and the reality of my existence set in. I guess you could say the novelty of dressing like a woman became a necessity when my gender called.

Speaking of my gender calling, I needed to learn how to accept it when it was trying to get through in my busy life as a man. I knew who was calling all of the time, I was just afraid of facing the reality of me answering it. I ran from it until I could run no more and I had myself painted into a feminine corner of reality I could not get out of.

What I am referring to is all the nights I went out as a trans woman to be alone and ended up socializing and carving out a new life faster than I ever thought possible. Suddenly, my gender phone was ringing off the hook and demanding more and more attention. The conversations became deeper and deeper as discussions about spouses, family and jobs took center stage. At a crucial point, I needed to lose all my fears of debating the pros and cons of gender change and consider the future which increasingly looked feminine to me. I respected the world of ciswomen from all angles, and I wanted to explore my desire to fit in more and more.

Finally, my gender voice became mildly abusive and challenged me to think deeply about the life situation I was in. What was I doing by constantly fighting a situation where I felt natural and good at. For once, I put my stubborn male self behind me and listened. Sure, there were bound to be bigots and haters still on my path, but I would have to ignore them and stand up for myself. The availability of gender affirming hormones or HRT helped me a lot because the hormones softened my skin and harsh male facial angles and made it easier to present a feminine face to the public. Which in turn, gave me more confidence. For the first time in my life, my external and internal features came close to matching.

At least now, my gender voice could quit screaming and calling me stupid for the way I was trying to run my life. Then perhaps, I could answer my gender phone and think about more pressing issues such as how I was going to run my life as a successful, happy transgender woman since happiness was something which eluded me for most of my life.

During a classic “if I had known then what I know now” moment, if I had known way back in my past how deep my gender issues ran, I was so much more than someone who enjoyed wearing feminine clothes. I wanted to be a woman as my ultimate goal in life. It would have been nice too, to have other guidance to help me along in my gender dysphoria struggles. In those days, not only were there not any qualified therapists to help, but there also wasn’t even internet to refer to for information so our closets were very lonely and dark.

Certainly, the one thing missing in my closet was a phone so I could talk when gender called. Maybe it would have saved me a great amount of stress and turmoil. I say maybe because of who knows, I would have had the maturity and courage to lick up the phone and have a honest and far-reaching discussion with myself about who I really was.

Maybe, when your gender calls, there will be a real person such as a supporting spouse to talk to about your life. So many transgender women and transgender men don’t have that luxury. One way or another, pick up the phone and talk. It could be the best therapy for you.

 

 

 

Thursday, March 5, 2026

More Euphoria

 

Image from Marcus Winkler 
on UnSplash.

Yesterday, I wrote a post describing the joys of gender euphoria and promptly received this comment from “Joey”:

Hello JJ! I am Joey. I discovered your blog today from a link on Stana's blog, femulate.org I am a crossdresser who presents male while wearing tasteful, feminine outfits. I do feel some euphoria, primarily when I have been out in normal life while dressed pretty for a couple of hours, and all of the stress hormones go away. Only my wife and a few other people know about this side of my life, so it is stressful when I go out in public every week or two. But after the stress, it is very freeing and happy!

First of all, Joey, welcome to the blog! Hope you enjoy it. The feelings you described were similar to mine too. I know I could not wait until I could shed my male clothes, wear something pretty and sample what the world had to offer for me that day before I had to go back to my old boring stressful male existence. Sure, I felt stress going out as a transgender woman when I first started to do it, but it was nothing compared to my male life. When I was mistaken for a ciswoman, my heart literally sang with joy, and the best part about it was, it all felt so natural. What a homecoming!

My only caution about seeking out more of the male to female femininization process is, it led me to take premature chances with my life. I did not understand all the layers that went into a woman’s life and the only way to gain understanding was by doing it. It was only then that I was given the opportunity to look behind the gender curtain to see what really went on. As I did, I was surprised to learn that many things were the same and women learn in their lives to keep certain things secret from men. Which is why both genders have such a difficult time understanding each other. For example, ciswomen have developed two basic ways of negotiating their lives which have to be understood by any novice transgender woman.

The first is the use of non-verbal communication. Women often give information to other women through their eyes and bypass men all together. I can’t tell you how many silent warnings I got from other women when I was in potential danger from a toxic male.  The second major lesson I learned was how to operate in the new world of passive aggressive women. I needed to have my head on a swivel to look for some other woman coming after me after she initially was smiling and was nice to me. I looked at both of these major changes in my life as just another way of playing the game, and the only problem I had was switching gears when I had to go back to my male life. I had built a career of being aggressive in my business and the change was often difficult for my mental health.

Even though the path went quite slowly for me several times in my life, on occasion, it sped up. Almost to the point of being out of control. My male self-had a unique way of saving his existence when it was on the brink of being taken away. Which made matters worse in my convoluted gender world. How could he continue to be so strong in his resistance when my gender euphoria was so strong when I was successful as a trans woman? I am sure you can understand my dilemma and perhaps have even been there yourself. Somehow, someway, I needed to arrive at a point where I did not define myself as a transgender woman. I defined myself as just me.

Sadly, that point did not come for many years in my life. As my male self-fought long and hard for his right to live on in the world he was successful in. Many times, I good old shot of gender euphoria was all I had to keep going if I was ever going to have a chance of reaching my feminine dream of attempting to live full time. Fortunately, for my life-long dreams, my gender euphoria turned out to be strong too, in its own way. Far past the feel of hose on shaved legs and the sound of my high heels when I walked, all the way to having the confidence knowing who I was. Acquiring the ability to look and another woman eye to eye and communicate on her level was so important to me as I needed to break the communication gap I had with the world when I started to live as a transgender woman.

I am aware that gender euphoria can be different for all of us as we follow our gender paths. Referring back to “Joey’s” comment that she enjoyed being tastefully dressed when she went out. That became so important to me too when I was able to begin to blend into the everyday world as I knew it. Out went the too short miniskirts, replaced my more tasteful denim skirts was a prime example. I was told my legs were always a fashion positive for me so I wanted to show them, but I learned moderation was the best way to go when it came to my male to female femininization process. When I did, my moderation led to a different kind of gender euphoria when I searched for the best way to find my dream.

Euphoria, I found, is also joy of living in a feminine world. Where I always dreamed, I could be. More importantly, once I got there and was living my dream, it was everything I thought it could be and I started to wish I had not waited so long to do it. Of course, thinking that way was just wishful thinking because we are given only one life to live.

I learned I had made the best choice I could and living as a woman was the way to do it.

 

 

Saturday, February 21, 2026

A Little Success Goes a long Way

 

Hair by JJ Hart. Bead Work
by Liz T Designs

In the life of a novice transgender woman or man, a little success can go a long way. Mainly because very few of us are blessed with the natural gender characteristics of the gender we feel is truly us to get us started.

At that point, we must feel our way along. Sometimes submitting ourselves to abuse from the public as we go forth in the world for the first time. In my case, I make no secret of the many times I headed back home in tears after being laughed at to my face in public. Somehow, through it all, I was able to catch and enjoy brief moments of gender euphoria to keep me going to a distant dream of possibly living a life as a full-time transgender woman. Of course, I did not have any idea that I actually could do it.

I was fortunate that practice made perfect (or close to it) as I was able to improve my makeup and clothing skills to where I could survive in public when I left my mirror. Which I discovered was one of my biggest problems because it had the tendency to lie to me when it came to my overall appearance as a woman. Too many times, I went out thinking I looked great and then had the world slap me down in laughter because of the mirror. Plus, my male ego was giving me the wrong impression of how to look as I attempted the sexy look when I was in my thirties not in my teens. There could be no shortcuts in being able to present myself well as a trans woman, I would have to concentrate harder on my makeup and wardrobe than anything I ever tried before. Just because I was trying to dress sexy and show too much skin would not work in the real world if I was to blend in with the other ciswomen around me.

Finally, success did come to me as I haunted the thrift stores in my area for just the right fashion to attempt to flatter my testosterone poisoned body. It turned out I could not attempt to test my success until I left the gay venues I was going to and tried to go straight with my public excursions. The gays did not care how I looked and just viewed me as a drag queen any how so I was wasting my time until I discovered how I could make it or not in the big sports bars I was used to going to as a man. When I followed my three-step method of acceptance, I had no problems being accepted. My three steps were to put my fear behind me and smile, never cause any trouble and tip well earned me the right that every regular had. Especially the one I cherished more than anything else, the right to use the women’s restroom.

With my success came responsibility. I needed to be on the alert for other strangers who wanted to talk to me. Especially ciswomen who were curious about why I wanted in their world. Success in my communication skills led me to learn more about living behind the scenes as a ciswoman than I ever though I could. My primary example I always use is how women use the power of nonverbal and passive aggressive communication to get by in the world. Especially when it comes with dealing with men. It was very difficult for me to learn the basics women use to live but as I did, a whole exciting new world opened to me. Perhaps the best part of it all was that it felt so natural, so I knew I was on the right gender path in my life for the first time.

My success then began to go a long way when I discovered a small circle of women friends I could socialize with on a regular basis. I was always a social person anyway, so the fit seemed fun and natural to me as I gained the confidence I never had before when I was a solitary, lonely cross-dresser. And the best part was, I was having the opportunity to learn from the other women around me about knowing how it really was to interact with the world as a transgender woman rather than how I always dreamed it would be. Needless to say, I learned a lot.

I looked at my whole experience as paying dues as I went from being laughed at in public all the way to having my own set of ciswomen friends to socialize with and even marrying one later in life. Ironically, it was my wife Liz who convinced me once and for all to put my male self behind me, give away all my male clothes and start gender affirming hormones. Which I had always considered the next logical step in my male to female gender transition. It turned out, hormones would be the great “aha” moment in my life as the femininization process took hold. It was as if I should have always been on the hormones because the process felt so natural. The changes went way past the external softening of the skin, breast and hair changes all the way to all the internal changes such as emotions and more.

For me, success took a long time coming, and early failures at passing in public made me very timid. Once I made it through all of that, success came more naturally to me. All the way from just leaving the house cross dressed to HRT, my life became a blur of changes. Sure, the battles I needed to fight came at me fast and furious because I was so embedded in the male culture but I was able to fight my way through them and be successful as I discovered a little success went a long way and kept me going along my gender path towards a life I had only dreamed of.

Friday, February 20, 2026

Time Flies When you are a Crossdresser

Image from UnSplash. 
Since now I have been blessed with making it to the age of seventy-six, I spend a lot of time wondering what I did with my life.

As I mentioned in yesterday's post, I spent much of my time running from myself by changing jobs and moving my family. At the same time, I was doing all of that, I was busy cross-dressing to keep my fragile mental health together. I started the same way most of you with gender issues did by trying on my mom’s clothes and moving on from there. The urge was so strong that I even went out and got a newspaper delivery route (back when newspapers were relevant) so I could make extra money to buy my own makeup, panty hose as well as other feminine items I could afford. Before I knew it, I was becoming fairly proficient at applying my own makeup. So good that the first time I talked a ciswoman into making me over into a woman, I thought I had done a better job with my makeup.

Those were during my college days which were split in two by my military duty during the Vietnam War and all cross-dressing activities were brought to a complete halt. When you are younger, years are more precious and the time away from my makeup, dresses, and wigs seemed impossible to face. Somehow, I made it through and even discovered the magic of attending a Halloween party dressed as a woman while I was in the Army. The good news is I did it but the bad news was the time was very limited, and I had a lot to go over in my mind including Halloween was then another year away. What would I do in the meantime to help solve my cross-dressing dilemma.

What I tried to do first was to drink my gender problems away, which only partially worked because when I sobered up, my issues were still with me and sometimes potentially worse when one night in the Army I told three close friends I was actually a transvestite and like to wear women’s clothes. Not just at Halloween. I was lucky, the word about my gender issues never got out to my higher ups and I went on to serve out my time with a honorable discharge.

When I rejoined civilian life, I had the chance to seriously consider making the gender jump from a male life to a female one. Following serious consideration, I felt the leap would just be too far to make, so I reluctantly chose to stay on the cross-dressing path I was on. To do just enough in front of the mirror to maintain my sanity.

Nothing changed until I began to leave my mirror behind and experience life in the public eye as a novice cross-dresser. Or so I thought. All was good, until the night something clicked in my mind when I was getting ready to go out to the straight venues I was visiting when I left the gay spots behind. As I examined myself in the mirror, I stopped and said what I was doing.  I suddenly felt empty and needed more and then concluded I had taken just dressing as a woman as far as I could. I needed to experience the next step which was actually interacting one on one with other women as an equal. Even though the idea scared me to death, I needed to hitch up my big girl panties and transition again into a full-fledged transgender woman. The venue I chose was TGIF Fridays I was familiar with as a man and I knew if I could make it past the hostess stand with no extra attention, I had a good chance of finding a seat at the bar with the other women who were just getting off work at the nearby mall. Amazingly, my plan worked to perfection, and I made it to the bar and claimed my seat. The bartender waited on me without showing any signs of gender disgust and I even ordered a second drink to celebrate my successful major transition in life. From serious cross-dresser to novice transgender woman. Even saying the word felt good to me.

By the time, time was flying by as I was trying desperately to build a new transfeminine life while at the same time maintaining a long-term marriage and successful job. I found I was not too successful as a juggler because the same time I was feeling good and natural as a trans woman my male life would sneak back it and ruin it for me. Eventually, it all became too much for me to handle mentally, and a suicide attempt followed.

Maybe I spent too much time in my life obsessing over my feminine appearance which I attribute into being a very serious cross-dresser. Certainly, all the successful public appearances I made as a woman were not helping me with my ultimate goal of living my dream. In the long-term, I never bargained on going through two major male to female femininizations to even come close to discovering if I could find my true life and live it as a successful trans woman. Maybe I was too shy or scared to go too fast. One way or another, it is too late now to cry over torn panty hose. Life gives us only one chance to get it right.

Wherever you maybe in your gender transitory journey, I hope you can steer clear of the major roadblocks’ politicians are attempting to out in our way as transgender people. May your path be as smooth as possible as your own time flies by as a cross-dresser or transgender woman.

  


Tuesday, February 17, 2026

Is It All Competition

 

Image from Gavin Allenwood on 
UnSplash. 


As I began to follow my gender journey, I did have some sort of an idea on how cis women compete in the world and how it differs from men. The one mistake I did make was thinking women somehow operate in a kinder/gentler world when it comes to competition.

Once I was allowed to play in the girls’ sandbox and get into a couple brief but intense scuffles with other women, I learned the hard way that women were into it as much as men when it came to what was important in their lives. The difference being was what was important. Men of course, compete in athletics and business while women tend to build their lives around family and home. And let’s not forget the influence of appearance with women. While it is a shallow existence, some women have a tendency to make friends and socialize with other women who fit in with their appearance. I remember quite clearly trying to watch my pre-teen granddaughter try to socialize with and fit in with a much prettier girl at a birthday party she was at. This extended with me all the way to a lesbian mixer I was at one night when a friend of mine wanted me to approach a very pretty femme lesbian for a date for her. It turns out that both my granddaughter and lesbian friend were both out of luck.

Not unlike when men try to date beautiful women and get rejected. I know when I started down the path of getting out in public as a novice transgender woman, I was only concerned about my appearance. I felt I was working to compete one on one with the other women in the world I met. How was my makeup, hair looking and did all my accessories match the rest of my outfit was all that was important to me. It took me awhile to go through this portion of my life as a cross dresser and emerging as a wiser more mature feminine person.

It was also about this time when I started to really engage with other women. Which was a real challenge because I was so timid. What would I say and how would I say it became I bigger priority other than just how I looked. I discovered too, the power of the submissive compliment to start a conversation. An example was when another woman would come up to me and compliment my earrings to start a conversation. When in reality, she was just curious to find out what I was doing in her world. In particular, I found out that I needed to beware of the you look great compliment because it could be tied into a compliment such as a man dressed as a woman.

It turned out, when I built my own circle of ciswomen friends, I did not need to worry as much about competition in the world anymore. When I was approached, it was when I was part of a group of out-going women who without thinking, shielded me from any negative people. The process worked wonders for me because I could set back and learn how to act from the other women around me and only step up and out when needed to secure my place in the group.

Slowly but surely, my competition turned to confidence that I could live the dream life as a transfeminine person I never thought I could be. I began to join writer groups with my wife Liz which in turn helped build further my new life because these people never knew anything about my previous life as a male. It all separated me from my old unwanted life and propelled me into a future I so wanted.

Furthermore, I did not have to compete in the world with other women. If they had a problem with me, so be it. It was their problem not mine. I did not have to please everyone was a powerful moment in my life. But without all the gender competition I went through, I would have never made it to the point I am today. I learned from how men compete with each other as well as women from both sides of the gender spectrum. Typically, men don’t compete well with women at all, and I knew that going in. So, I knew what to expect. With other women though, I did not have any idea at all. It took me a long time to learn feminine competition and how it worked.

As I said, once I did learn to compete in the real world as a trans woman, my life changed for the better and I truly began to live the life I always dreamed of.

Monday, January 19, 2026

Setting New Traditions

 

JJ Hart bottom row, left. 
Girls Night Out Birthday Party

Establishing new traditions or routines can be difficult when you decide to finally live as the gender you were always meant to be.

In my case, the biggest moment of change was when my regular invitation to the family’s Thanksgiving feast was rejected by my brother and sister-in-law who did not have enough backbone to stand up to her rightwing Baptist family. The excuse I was given was, what would the kids think. I was fortunate that my dramatic change was by my daughter and my future wife Liz. Both of them invited me into their family gatherings with open arms and I ended up having an even better time than I would have had with my brother.

Other traditions I was invited into were girls’ nights out for various special occasions such as birthday parties. I cherished the chances I had to go behind the gender curtain and see how ciswomen interact with each other when there are no men around. Sure, I was terrified to go at first but quickly calmed down and warmed up to the experience when almost all of the women there treated me as an equal. Surprisingly to me, I ran into no problems except for one woman who acted as if she was mad at the world anyway. Plus, my most important lessons were if you take men out of the picture, women are looser acting around themselves and the only real difference in the conversation is the lack of sports and job talk. The bulk of the conversation was built around family and spouses.

I took these new learning experiences with me and ran with them into my everyday life’s interactions with other women. I subtracted any talk of employment and my major interests (sports) unless I was asked about something specific. Which surprisingly I was not and my private life which I had not merged at that time, stayed mine. No one pried, and I did not offer. Which worked well for me.

As I slowly began to build on the experiences I mentioned, life became more fluid and natural to me, and I knew I was on the right path. I felt better after spending a night with the ciswomen than I ever did when I was busy posturing with other men. It just took me time to establish new traditions, and I came to expect the occasional invitation to join other women in their celebrations. I became my own woman, just from a different background than the rest of the group. As I learned so much, most of the women never knew how much they benefitted me by just allowing me into their lives. Including the lesbian experiences, I had which went such a long way towards shaping my future.

From the earliest days of going to diverse mixers in Columbus, Ohio and ending up leaving with a lesbian I talked to, all the way to attending lesbian mixers with Kim and Nikki in Dayton, Ohio years later, I again was able to learn so much about the sort of woman I wanted to be. As many of the transgender women around me were stressing about finding a man, I learned I did not need a man’s validation to be me. It really helped me to not needing to change my sexuality while I was building new traditions in my life. I had always appreciated the company of women around me and nothing changed.

If you are considering, or are building new ones, as you know it is a major deal and one that can take a while. My advice is fairly simple, pursue as many avenues as you can and be prepared for the occasional rejection you may receive. Especially from men who may perceive you only as some sort of fetish object. And of course, be safe and meet strangers in public places initially.

Sooner rather than later before you know it your new traditions will become established and second nature to you. That is when the woman who has always been a part of you can emerge and live the life she always imagined. Jumping the gender border may be something you were always destined to do but never dreamed you would have the chance to do it like I did. I needed to wait for decades as I experimented with my gender but finally the doors opened wide for me to find myself in a do or die situation. Either try a male to female transition which was always a female-to-female transition in my world or forget it and move on with my life at the advanced age of sixty. It would have been easier just to do what I always had done and live a life with one foot in each of the binary genders.

I took the hard way out and decided to pursue the next step in my transition (it was a big one) and seek a doctor’s approval to begin gender affirming hormones or HRT. It was a huge step for me and one I did not take lightly. My body took to the new hormones like why did I take so long to do it? It fit right in with the rest of my life of waiting too long to do what was right. Establishing new traditions in a life I always should have known was just the beginning.

 

 

 

 

Friday, November 14, 2025

A Marathon not a Sprint

 

Image from Peter Boccia
on UnSplash.

In my life, I have rarely ever had to run any distance at all. The only times when I did was when I played football and was in the Army. So, I was never a sprinter until I discovered my love of cross dressing as close as I could to a pretty girl. I could not wait until I came home from football practice, and no one was home so I could put on a short skirt like the cheerleaders I admired so much, were wearing.

I wonder now, if I knew how long it would take me and all the trials and tribulations I went through to arrive where I am today, would I have given up on my journey. I doubt it because along the way, my gender feelings ran so deep and I felt so natural as my feminine self, I could have ever turned back. I needed to settle in for the gender marathon I was facing because sprints (which I compare with brief moments of gender euphoria) were hard to come by. It is a good thing, because I was always better at marathons anyway.

I can blame my marital situation on the fact that I was still trying to run gender sprints. Rather than face up to the truth of who I was, for years I tried to maintain the delicate balance of a stable marriage and a rapidly growing love of public living as a transgender woman. All my sprints did were cause problems at home when I was caught and put a tremendous strain on my twenty-year -plus marriage. On occasion, life between us became so bad my wife on several occasions simply told me to be man enough to be a woman. I hadn’t been yet, but I was working on it. She did not know it, but her challenges kept me going during my gender marathon. I just needed time to get it through my old unwanted male head that being a woman (transgender or not) meant more than looking like one.

I receive many comments from those individuals who are just wondering where their gender path will take them. When I do, I try my best to point out I did not magically appear where I am now. It took me a lot of work and disappointment to realize I needed to be better than the average ciswoman to survive in their world. They had a head start on me in the race to womanhood and I needed to work hard to catch up. Along the way too, I found some ciswomen were eager to help me into their world, and some were not. Maybe they had their own marathons they were running in life.

Another thing I learned from running a gender marathon was I had the time to relax and enjoy the journey on occasion. I felt much different than the fast pace of fleeting gender euphoria when I was involved in a gender sprint. Then, it was back again to living in the present as a transfeminine person, rather than living in the future and missing most of the enjoyment. Slowing down also gave me time to research who I really was and who I was, was on the right path in my life. Because I had huge decisions to make. Family, marriage, jobs and friends could have been all on the line. At times I was crushed under the pressure of it all and had to put it down for a different day. Something I could have never done as a gender sprinter.

The moral to the story was that slowing down helped me to determine my own pace. The problem was that I wasted valuable time coming out of my male closet longer than I should of. I finally came to the conclusion that I could not have it both ways. I ended up doing what was right for me keeping in mind that your story you are writing in life could be totally different.

Either way, what you consider is a gender sprint or a marathon is a personal matter and has a lot to do with how old you are. Even though I have read about male to female transitions well after the age of sixty (when I did it) I think it is rarer because those who think they can put it off longer because they have put it off as long as they could. But then, on the other hand, there are people like me who realized their gender truth and could not put off making a move any longer. Before I had to sprint for the finish line of life itself.

 

 

 

 

 

Saturday, October 25, 2025

All that And More

 

JJ Hart

When I jumped from the cross-dressing world and I went into the public, I found myself in a situation where all that was more in my life.

Why? Because I was very naĂŻve about how the two binary genders react to each other. In my relatively sheltered male life, naturally I had only experienced life from the male side only, and I was trying my best to make all I could out of it. To make matters even worse, I was so shy I could barely talk to girls at all. So, I never had any experience with them. No experience led to no confidence which sent me further into my shell.

I used my shell to protect myself the best I could and give the best impression I could that I was a so-called normal boy. For years, I fought the good male fight and internalized all of my feminine feelings. In the meantime, I was studying the girls and women around me, daydreaming of the day I could be just like them. My gender workbook was blank at the time, and I should have hung a sign on me saying “no experience necessary to survive.” In the meantime, I immersed myself in sports and cars and appeared to the outside world as a normal young male. There I go, using the “normal” word again, when I know now, there just isn’t such a thing.

It took me years of trying to break out of my shell or closet and tentatively go out into the world as a girl. I started at night by going to places I knew would be deserted but then again had big windows where I could still see my dim reflection. I was actually headed to a book/magazine store where I could hopefully navigate the books but never had the courage to do it and ended up going back home deeply disappointed in myself. Slowly, I resolved to do better but I never did make it into that particular store. Instead, I began to explore the world of women’s clothing stores where I found any number of helpful clerks who were more than willing to look past my gender, and into my available money.

After I realized that the women’s clothing stores were too easy on me and did not present a challenge, I began to branch out and try to look for more challenging venues. I came up with the plan to stop for lunch when I went out cross-dressed, just to see what would happen. I discovered that when I was dressed to blend in with the rest of the cisgender women around be, I was able to interact with the servers waiting on me. More importantly, I was beginning to realize, it was easier for me to talk one on one with another woman than it ever was when I was a man. It was a huge point in my life which ranked right up with realizing I was much more than a male wanting to wear feminine clothes on occasion. It would lead the way to me discovering I could live the transfeminine life I had always dreamed of.

In many ways, I was able to channel the pure fear I felt when I went out for the first time as my true authentic self and turn it into energy I used to further my communication skills with the public at large, and women in particular who seemed to be more receptive to me because I was in their world. Before I knew it, I was able to settle down and begin to enjoy my new life as a transgender woman. To be sure, I was different than most everyone else I encountered but I wanted desperately to make it a positive difference. Mainly because nearly everyone I met had never known another transgender woman or trans man in their life. I just had to make our meeting a special occasion which was all of that, and more.

In return, I was learning valuable lessons from the ciswomen I met. In ways they never realized, the women helped me discover the wonderful world of my own womanhood. In doing so, I was able to navigate the pitfalls of my male to female transition and always move on to higher ground.

When I did, I went on to discover the layers of life women live in during their lives which they hide from men. My life went from chasing a dream to living it as I discovered a transgender woman’s life was all that and more.

 

Monday, October 20, 2025

It's Halloween Season

 

Image from Andrea Li
on UnSplash.

It is finally here, the season that all cross dressers and novice transgender women dream about, Halloween. It is the magical day when we can be ourselves without all the paranoia of being caught and exposed as a man wanting to be feminine. The time when everyone has a chance to cross the gender line and be themselves.

These days, since I sadly don’t participate in Halloween much anymore, I don’t write much about it. But back in the day, I was fanatical in my Halloween preparations. Without fail, I would begin thinking of my “costume” the first of October and change my mind several times before Halloween itself. I always felt a transgender woman had the right to change her mind. Would I try to be sexy this year or try for a more authentic “costume” such as a professional woman look. Major decisions I needed to make with the added pressure of knowing it would be another year before I could take advantage of the parties again.

Ironically, the “costumes” I chose followed in many ways my progression as an early transgender woman. In the early days, I would try to dress sexy and get away with the shortest mini dresses and highest heels I could find. Of course, then, I would give myself away as more than just a casual “jokester” at Halloween by shaving my legs, wearing a long sexy wig, and having great looking makeup. Which my wife took credit for when she wasn’t and didn’t wear any makeup at all. Even the most casual ciswoman observers at the parties I went to could tell how serious I was about looking my best as a woman.

As I said, I quickly grew out of my sexy/trashy Halloween costumes and began to dream of being accepted my mistake as a “real woman” at the parties I went to. That began my era of actually being mistaken for a woman just getting off work and coming to one of the parties I went to. I was professionally dressed in a dress and heels and ended up surprising other guests I had known for years. For the evening, I went with another woman other than my wife and had to sadly turn down a request to go with another couple to a different party. Later on, I learned that the man was a politician who was elected to Washington, so my political career was quickly ended by saying no.

Outside of that party, there was only one other party I went to when I was dressed in a moderately sexy “costume”. It was during my stay in New York and another night I got out of the house without my second wife going with me, for some reason. This time, my invitation came from one of my female managers where I worked, so I looked forward to what the evening had in store for me. It turned out my sexy “costume” hair and makeup fit it perfectly with the other women I ended up meeting for the first time.

I ended up meeting everyone in my manager’s house and they were all there when I arrived. I will never forget the delight I felt when I saw they were all dressed like me, so unknowingly I had dressed to blend with them. Also, I will never forget the hush that fell over the room as the other women looked me over from head to toe. I ended up tagging along in my heels, hose and mini skirt with all the other women who were almost as tall as I when we made our way to a close by neighborhood bar where the party was taking place. I had my misgivings about how I would be treated there, but after I was in the bar for a while, there was no indication from anyone that I was not anyone different than I appeared. I was even asked if I wanted to dance by a man. All I know was the night flew by in a hurry and my wife did not speak to me for days because she saw my “costume” before I left.

Even though my Halloween highs were very high, sadly they were accompanied by very lows I needed to suffer through. I became very depressed and mean and tried to make everyone around me feel the same way. My problem was only ultimately solved by getting out of my dark gender closet more than just once a year.

In order for me to exist in a life I was discovering I needed, I had to set Halloween aside as just another day. Which ultimately took all the fun and drama away from it. But sacrifices had to be made for me to live as a transgender woman and Halloween was just one of them.

 

Wednesday, October 8, 2025

Trans Girl Acceptance Versus Competiton

 

Image from UnSplash. 

As I increased the intensity of my male to female gender transition, I was under the mistaken idea that women were not as competitive as men. Very quickly I discovered I was wrong. As with many other gender specific issues I faced, women compete as intensely as men, just on their unique level.

When I grew out of my teen girl dressing stage and began to blend in with the ciswomen at large in the world, I received my first real taste of feminine competition.  As a  man, I had always thought women dressed for other men, when if fact, they were dressing for other women. Once I got that through my thick head, life as a novice transgender woman became easier for me and I could finally progress in my journey out of my closet into the real world.

As I progressed. I wasn’t totally clueless about the differences between genders. My entire life, I had made it my business to study the world of women in case I ever made it in their world. Little did I know how difficult it would be for me to gain acceptance from the alpha female gatekeepers to the world I always wanted to be part of in the worst way. Perhaps, the most important lesson I needed to learn was how ciswomen competed in life. I had always assumed one shallow fact that women only compete on an appearance level. When in fact, they compete in a very complex layered system.

Maybe you have heard the term “Mama Bear?” It refers to women who intensely support their kids and family as one example of how women compete outside of just looking good. My daughter is a great example of a “Mama Bear” as she goes out of her way to protect her transgender child. There are plenty of other examples I have of women competing on a level which includes appearance. My company I managed a unit for used to throw lavish holiday parties which the women managers would go all out for in their gowns. Of course I was jealous as I was stuck in restricting, boring men’s clothing when I would have loved to have been in one of the fancy gowns. But I missed my opportunity again.

I found out too how women compete to keep their man. In yesterday’s post, I recounted an encounter I had with a less than pleasant woman who came back from the restroom and found me talking to her man. They left the venue quickly and I was left with claw marks down my back. Somehow, she thought I was competing for her man, and I never made that mistake again.

Another example could be the number of ciswomen who have no problem with transgender women or cross dressers as a group, UNTIL gender issues invade their own family and their husband comes home and opens up that he wants to be a woman. Then the real work begins from both man and wife as they try to discuss a gender transition. Afterall, what would the wife tell her friends and family.

The flip side of feminine competition is the wonderful world of cisgender woman acceptance. Depending on who you are asking for acceptance, expect a long journey of approving yourself as a worthy candidate for womanhood. As my wife told me so many times that I made a terrible woman, I needed to find out what she meant because I was beginning to have success in my feminine appearance. In her defense, she was right and until the gatekeepers let me behind the curtain to learn the world from a woman’s perspective. I did make a terrible woman.

Maybe you have known that one special ciswoman or two who have had that seemingly unlimited ability to love and accept the world. It is true that nothing can replace a woman’s love. And I have benefitted from them my entire life. Starting with my own mom, who after three still births kept trying until I came along. Plus, I can’t forget the wives who had loved me in their own unique way while I was on my solitary often selfish journey to transgender womanhood. It was not their fault I refused to face my gender truth.

Finally, it was an assortment of women such as Liz, Hope, Kim, Nikki and others who believed enough in me as a person to let me in to their world. They were my gatekeeps who showed me I didn’t have to compete with other women to be successful in my new life. Acceptance from them was all I needed. When I needed to compete, I could do it on a woman’s level because I had been there and done it.

 

Friday, October 3, 2025

No Way to Solve a Problem

 

Image from Babi on UnSplash.

When I discovered my true gender issues that were disrupting my life, I needed to try to solve the problems they created.

In order to do it, I set out on a lifetime journey of discovery. Like most of you, I began my explorations in my mom’s clothes and even tried my hand with her makeup samples. My mirror often lied to me and told me I presented as a pretty girl. Of course, in my pre-teen years before testosterone began to change me, I had an easier time of looking the best I could as a young girl.

When testosterone came along with puberty my problems became real. At the same time, I was becoming better at hiding my collection of feminine clothes I found and was able to buy from my meager allowance. I became very resourceful when it came to my cross-dressing desires, as I even resorted to a cheap Halloween costume wig to get me by for years until I could finally afford to buy one.

As I chased my feminine tail from one close call to another with my family, I wondered why I was cursed with the gender problems I had. In addition, I felt as if I was the only one who had them. I was trapped in a male dominated family who would never understand a boy who deeply wanted to be a girl. My only choice was to keep trying the best I could to solve my problem.

It took me years to realize my so-called problem was more of an opportunity than anything else. But first of all, I needed to face my problem woman to man. No more of my second wife telling me to be man enough to be a woman. It turned out, I was man enough to be a transgender woman, but it was going to be a real battle. By this time in my life, I had accumulated quite a bit of male privilege I knew I had to lose in order to be successful. Basically, for a while, my female self’s main strengths where she felt so alive and natural when given a chance to shine.

As she took advantage of her time in the public’s eye, almost all of my problems seemed to melt away, and I began to feel having the opportunity to experience both binary genders up close and personal in my life was not a problem at all. I just made it one due to my inability to deal with it. I just had too many gender obstacles to overcome. I had accumulated too much male baggage I doubted I would ever be able to live without. It turned out, I could live without most of them, and surprisingly, I could bring some of the baggage along. My prime example was my lifetime love of sports, which I found a group of cisgender women who were as serious about sports as I was, so I was able to fit right in and even have fun.

The new and improved me proved I had lived most of my life as a man as a lie. All the time I spent worrying about wearing dresses and makeup was a waste of time. I had my whole life backwards. My wife was right; I was not man enough to be a woman for the longest time. Once I was though, I never looked back. I can’t say I was prepared for all the changes I was about to make; I was excited about the opportunity I was given to make them. Which most people never get.

It was certainly never a way to solve a problem; I learned the hard way.

 

Sunday, September 7, 2025

Off or On the Transgender Highway

 

Image from David Valentine
on UnSplash. 


When I seriously pursued my male to female life as a transgender woman, along the way I was fooled into thinking I was on a smooth fast interstate highway.

What happened was I was stuck on slow-moving two-lane gender roads and going nowhere for years. Plus, I needed to keep an eye out for potholes bumps and sharp curves. Too many times, I led myself down dead-end streets when I transitioned. The entire process just slowed me down and I lost decades in the process. Then I discovered one of the main problems I had was my old male self was exercising too much influence on my life. My main example I always use were the ill-advised fashion choices I was making when I tried teen girl outfits in my thirty-year-old testosterone poisoned body. I was guilty of not looking around and noticing what other women my age were wearing or what I could wear to disguise the defects I inherited with my body. Even though I was always going to be a big woman, there were plenty of other women my size to blend in with in public. While I am not a huge proponent of age women’s fashion, I am a proponent of looking good and not shocking the world.

One way or another, as I was able to put most of the fashion mistakes behind me, I was able to speed up a little and enjoy the new small gender towns and cities I always wanted to visit as a woman when I was a man. There were to be no more miserable vacations when all I thought about was when I could cross-dress again in front of the mirror. I was far beyond that point. I had developed the confidence I needed as a transfeminine person to take the next two-lane highway ahead and see where the journey took me. More than anything else, the mini trips taught me I could not go to sleep on my gender journey as I was risking my life as I knew it at the time.

In many ways, I was used to the pressure of discovery all along since it had started when I was so young. I just ended up accepting the pressure as a way of life for me if I was ever going to achieve my dream of living as a transgender woman. It all started with the threat of a psychiatrist visit when I was quite young, all the way to losing my family and job if I was discovered later in life.

Perhaps the biggest mistake I made on my road was trying to internalize the entire process and going through the infamous ill-advised purges of everything feminine I owned. It turned out to be one of the dead-end roads I was facing when I found I could not purge my deepest feelings of wanting to be a woman. In no time at all, I was back on the road and ready to try to get on the gender interstate. Many times, I was guilty of taking the wrong exit and having to go back to start all over again when I made the wrong choice of a venue and tried out a red neck, rightwing venue when I should not have. One time, I even had the cops called on me when I visited one venue, I was not familiar with.

After being told to leave, I quietly did and regained my composure up the street at a place where I knew I would be accepted and got back on the road. Once my transgender life began to speed up, I was able to stay on the interstate gender highway thanks to a lot of help from my cisgender friends who taught me more than they ever knew about discovering myself as a trans woman. More than anything else, they propelled me forward towards my dreams. They validated me to a point where I did not have to hide myself anymore on a bunch of dark deserted two-lane roads and stay on the well-lit interstates. I mention them a lot because without them, I could still be hiding my true transgender self away in my dark closet.

It took me so long to transition, I wore out a couple of vehicles along the way, but I finally did it. Regardless of the naysayers who said I was not trans enough to make it, or I passed as a woman out of sheer willpower. I accepted my life for what is was finally at the age of sixty and did what I should have done years earlier. Stood up for myself and started gender affirming hormones (HRT) which was like getting a new sports car to drive on the gender interstate. Again, I was able to leave a lot of negative people behind and live the dream I always wanted to live, as a transgender woman.

 

 

 

Friday, September 5, 2025

Trans Girl Panic

Transfeminine person from 
the Baliente Agency
on UnSplash.
As I transitioned from male to female, I found myself in over my head more times than I can recall. But before I get started on them, I would like to wish my daughter a happy birthday. She has always been one of my biggest support mechanisms (ally), and I love her very much.

As I was initially venturing out of my gender closet for the first time, my daughter quite literally put me in over my head when she gifted me a visit to her up-scale hair salon she was a regular at. I will never forget the complete panic I went through as I had to walk a line of at least ten women in chairs getting their hair done as I made it to my stylist I was meeting for the first time. I needed to calm down and look around until I began to realize what women know about getting their hair styled. It is a gender affirming experience and there was enough estrogen in the room to help my minimal Estradiol dosage along. As my panic subsided, I began not to care what the other women thought of me, and I relaxed.

It turned out, my first trip to the hair salon was just the beginning of a lifetime full of panic filled experiences. Many of which were brought about by my own ignorance. Such as the night my daughter invited me along to join her women friends in Dayton, Ohio at a well-known drag show. The only problem was, I couldn’t let on I was her parent to several of the other women because my daughter did not know how they would react. No pressure, right? I did manage to talk only when I was talked to and enjoy the show from a well-known drag troupe which had raised well over a million dollars to AIDS research. By the end of the evening, I was confident I had done nothing to embarrass my daughter, which was my goal, and I calmed down.

Later on, as I branched out on my own, I found myself in plenty of embarrassing situations I brought about on my own. I went through ill-advised times when my water balloon breast forms exploded on their own and I needed to head quickly to the bathroom to try to repair the damage. Luckily, no one else seemed to notice the mess I made before I was able to pay my tab and leave. From then on, I made sure I purchased silicone breast forms and did away with the ill-fated balloons forever, so I did not have to worry at a time when I had so much else going on. I was busy trying to make the transition from male to transgender woman, so any unwanted disasters were not welcome.

Such as the time I pulled a very public slip and fall when I was wearing my new high heeled boots, I was so proud of. I learned fashion needed to take a back seat for me when the weather was bad. The only good thing I can say about the panic I was experiencing was it was teaching me valuable lessons. I learned when I entered a venue, all eyes were not on me, and I was OK to simply stand up straight and find my seat unless there was a hostess present.

The moral to my story is I had to be resilient and not collapse when feminine panic set in and I was completely out of my old environment as a man. All my previous escape mechanisms were stripped away, and I needed to form new ones. I even learned to use fear as a motivator when I began to change my mindset that I was a cross dresser to I was a transgender woman. I felt if I could make it through another major change in my life during my second transition, I could make it through anything, and my confidence began to soar. Also, I found I began to put my biggest fear behind me, and I could look another woman in the eye and communicate one on one. For once, I was free to completely explore the world as a new transfeminine person.

I used all my learning experiences as a trans woman wisely (including the mistakes) to calm my panic and move forward towards my impossible dream. As my mistakes began to fade into my past, so did my panic which helped me to be more efficient in the public’s eye. Having a clear head in a new world is so important to moving ahead. And maybe more importantly, deciding where I wanted to go as a transgender woman.

 

 



Monday, September 1, 2025

The Second Time Around

 

JJ Hart (middle) at my first
Girls' Night Out. 

If you are one of the rare human beings to experience a second time around in life, you owe it to yourself and others to live it the best you can.

Being transgender can give you that rare insight into two of the main binary genders which should give you an edge in dealing with the everyday world. Having an intimate knowledge of whatever the other gender maybe thinking of us as trans women or trans men brings out fear in the public's eye. Who are we to possess such a wonderful scope of knowledge anyhow? It is especially bad with the male gender who has such a poor grasp of their sexuality to begin with. I know when I transitioned from male to female, one of my main concerns was my own sexuality. Was I expected to suddenly change my sexual preferences which had always been with women and suddenly start liking men. I even went to the point when I first came out when a straight woman friend of mine told me to buy bananas and practice. I will let your imagination do the rest.

We all know though there is so much more to a gender transition than sex when you set yourself up for the second round in life. I found I was leaving a life as a man where I was mildly successful and entering a totally new world full of women who were able and willing to question my existence in their world at all. Away from men, the women were a complex tribe, and it was difficult for me to be given the access to play with them behind the obvious gender curtains. First and foremost, just looking like a woman just got me in the game and the difficult part was just beginning. I spent hours and hours in the world just learning how to be the new me.

Suddenly, before I knew it, the doors to a totally different world opened for me and I was invited to the girls’ night’s outs. The invites could never replace the learning experiences young girls have when they are in their formative years and they get to go to girls’ overnighters with friends, but they were all I had to attempt to catch up on my gender homework. No chance to experiment with makeup or gossip about boys or other girls.

The main problem was, I had another male life to deal with at the same time. Looking back, I don’t know how or why I put up with all the gender stress and tension I did to make it to my dream. I guess the reason was I did not have the confidence to know if I could make such a major life changing step at all. We all have a lot to lose when we undertake such a step, don’t we? Plus, as I slid towards the idea I could live fulltime as a transgender woman, I was being accused of being selfish. Which made me feel guilty until I finally came to the conclusion I was being selfish. Because I had to save my own life.

As I was accepted into the girls’ sandbox around me by the majority of the women around me, my confidence grew that I could indeed live a second time around life as a transfeminine person. My long hidden inner female took over and surprisingly became a rather social person as I formed bonds with my small group of lesbian friends which was the best of all worlds for me. As I always say, the first and main thing my friends taught me was I did not need a man for validation. Which included my sexuality. All I needed to do was still keep an eye out for the rare bigot who hated me for no real reason. It turned out the haters would have to go through my cisgender friends to get to me, if they wanted to.

At that point in time, I met my wife Liz, and my second time around became easier and easier for me to live up to. I say live up to because I found myself at a point where I always dreamed of being. But I never thought I could make it. Never say never became a reality for me when Liz told me she never saw anything male about me. I was in gender heaven and stayed there until I realized what a heavy burden I needed to face. Here I was with the rare chance for a do over in my life and to not repeat the same mistakes I made as a man.

So far so good I think as I head down the stretch run of my life and I can be thankful for the chance to live two lives regardless of what the gender haters say.

 

Set in Stone?

  JJ Hart When we are born, we are assigned a gender which is arbitrarily based on our genitals the doctor sees. Often, at that point, gende...