A Halloween Political Decision

Image from Nice M Nshuti
on UnSplash

This is the second in my month-long series of Halloween decisions I made during and after the parties I went to.

This party took place in a wonderfully restored Victorian Mansion in my hometown where I worked as a radio disc jockey. Just to get an invitation was impressive to me as I struggled to come up with a “costume” to wear. Ironically, by this time in my life I had almost went full circle in my choices of what I was going to wear. I had long since gone from my slutty/trashy woman look all the way to a more moderate less clownish woman with my “costume.” I could still try to be sexy without going overboard as most ciswomen around me were doing on Halloween.

I finally decided to go full circle and see if I could wear something so authentic that the normal party person would not recognize me as a guy at all. I thought it would be the ultimate chance to test how far I had come as a transgender woman in the world on a low risk-high reward Halloween evening. Once again, my wife did not want to go with me, so I ended up with the news girl at the radio station as my companion for the evening.

I discovered I was off to a good start as my companion for the evening marveled at my “costume.” I chose to be a professional woman, just getting off from work and coming to the party to test my newfound freedom in the world. For at least one night.

When we arrived and found a parking place, I loved how my heels clicked up the sidewalk as my “date asked me how long I had practiced in the heels to wear them as well as I did. I just told her longer than it took me to shave my legs and apply my own makeup, so she left me alone after that. As far as asking any further questions about my skills dressing as a woman. Fortunately, it was a beautiful warm evening for Ohio in October, so I did not have to worry about any sort of jacket, sweater or coat as we made our way up to the mansion’s front door. The whole house was beautifully decorated for Halloween, complete with a vintage wooden coffin complete with a real skeleton.

I was met at the door by the hosts for the evening who like my “date” marveled at my male to female transformation. With the good start I was having, I immediately started to relax in my new surroundings and enjoy looking at the other costumed visitors. I was just about ignored as I did manage to blend in as a professional woman until later in the evening when a couple arrived and started to talk to us. It was just after a little bit of conversation that they told me, they did not recognize me as a man at all, and my “costume” had worked. My mind was shooting fireworks of joy when they told me that and it even went on to new heights when they even asked me to leave with them and go to a different party.

By this time, I had recognized the couple who were very active in politics and was on their way to Washington due to a recent election victory. So at least I knew who I was dealing with and if it had been just up to me, I would have said yes and went to the other party with them. But it was not just up to me since I had driven and I needed to get my “date” back home, so I had to sadly make a split-second decision and say no. Either way, I was very flattered by the offer and who knows what I would have encountered as my feminine self at the other party. We stayed on at the original party for a while had a couple more drinks and headed back to the house where I needed to reluctantly return to my old male life for what I thought was going to be another year. Always maintaining the “what if” ideas if I had continued with the politician and his wife, Maybe I could have gone to Washington also.

Another good thing that happened with the Halloween party I went to was, it was the first time that I ever thought/proved I could make it in the world as my true feminine self. Plus, I knew I could not wait another year for Halloween to roll around for me to live as a novice transgender woman again. If I had made it one night as a professional woman in the world, there was no reason I could not do it again. I just had to take matters into my own hands and do something about my gender dysphoria which was helping to wreck my mental health.

The evening was also more proof I had done the right thing for a change when it came to testing the strength of my male to female femininization project. I found I was coming along faster than I thought and I could never go back to living the totally male life I had before I tested the gender waters at the Halloween parties I went to as a cross-dresser. It was as if I had found a giant search light on my gender path and suddenly, my life made more sense. It was so much deeper than anything I thought it could be.

That is why not going out with the politician and his wife maybe cost me a chance at more fun and even enlightenment about who I really was. But on the other hand, I did the right thing by my wife and my date if she did not want to go early and end my evening. I felt better about it in the years to come. Even though, I wonder what would have happened if I had made the other decision. Most likely nothing and the memories are better than the actual experience.

Another reason Halloween will forever occupy a special place in my soul and there were several other evenings I will try to pass along before the actual holiday. Thanks for reading along and commenting!

 

  

A Gender Yo-Yo

 

Image from Eric Prusak
on UnSplash. 

I have felt most of my life like I was a gender yo-yo. One day I was a boy and the next day I was a girl was the way I was living, and it was no fun. The ups and downs were killing me as it did in the future as I tried many self-destructive attempts.  Luckily, they failed.

Of course, my male self-received all the benefits since he was given all the advantages as I was born male and could do nothing about it. He got all the accolades when he did something right at home while at the same time, my feminine self-needed to remain firmly hidden away. Which did nothing to relieve the yo-yo gender life I was living.

Then, there were the vivid dreams I was having where I was the pretty girl. Sadly, I had to wake up to no changes in my everyday male world of having to compete daily with the rest of the male world I was in. It never changed so I was stuck and I could not go live in the world of women where I always wanted to be.  The yo-yo never seemed to slow down as life went by me, but I can say I did l learn to adjust to its up and down rhythms. As I began to understand what gender euphoria meant to me and how long it would last once it was over. The answer was a maximum of four to five days before the depression of not being an active participant in my own transfeminine life would set in and I would have to get creative and do something before my gender yo-yo hit the floor.

To counteract my depression, I began to research the meager amount of information I could find on gender issues way back then. The only term I could find was gender dysphoria which was labeled as a mental illness. So, I rejected it. All I knew was I was confused still if I was totally a male or a female. If the term had been popular back, then I have used gender fluid for awhile to describe myself. At least it would have worked until I began to run out of male fluid altogether. Since I did not have the mental willpower to find my gender fluid leak, I concentrated on keeping track of my feminine side. As I became a regular at LGBTQ diverse parties close to where I lived. It was like going to one of those quick oil change places where I could rejuvenate my feminine self around like-minded others. From lesbians I learned shared an attraction with me to toxic cross-dresser admirers, I was able to experience and learn from them all.

On the negative side, like my yo-yo, what went up had to come down as far as my gender euphoria went. Not too long after going to the parties, I started to miss the experience and wanted to do it more. Which made me a spoiled brat when I lost my yo-yo completely and could not find it. I was learning how to live a new life where I fit in as a secure transgender woman, but I was not there yet. What all my research at the parties proved was I had just scraped the surface of where I wanted to go as a trans woman but still had not had the chance to research where I needed to go internally. The internal piece would be the hardest to do because I had learned so effectively to wall myself off from the outside world and ignore it. As I struggled to live a life as a man.

I finally had to listen to the world and discover my internal piece was the biggest part of my second wife saying I made a terrible woman. Because I did before I was in the unique position to remake myself. Maybe in many ways, I was a clueless person all together and that would have to change before I could ever move forward into a better world. I had the chance to take what I learned in a male world and build a solid female world was a chance I just had to take. I needed to take a new approach and put the imbedded emotions of my yo-yo aside. It helped me with all the ups and downs I was feeling specifically with my mental health. I finally had to face the truth about myself and freed me up to be me as I always say.

If the truth be known, I was never any good with my yo-yo anyhow. My male-equated hand-eye coordination stopped me from doing more. Maybe it was my fault because I was always so biased about being male at all. Through all the ups, downs and sideways, I knew I could not take it anymore. It was time to take a time out from him and learn what life would be like of I took the transgender plunge. Was I risking all that I had earned to live my dream or not. I thought I would be fine after all the research in the world I did but I needed to make sure. What I discovered was I did not care for good about the risks I was about to take. As I said, I had put that old yo-yo away for good.

Hopefully you have been able to put that yo-yo of yours away too. It is certainly no fun to do it. Thanks for reading and commenting.

 

The Right Place but the Wrong Time

 

Image from Alexey Demindov 
on UnSplash.

Perhaps you remember the Dr. John song “Right Place, Wrong Time” from 1973. In his classic style, he bemoans being in the right place at the wrong time in his life.

Sometimes I think the song could be the theme of my life. To start with, I was born against all odds, seeing as how my parents had suffered through three stillbirths before I came along and survived. I was in the right place to thrive in a family who loved me, but I was in the wrong place when my gender was determined to be male. Something I could do nothing about for many years.

Without knowing it, I was being set up for all sorts of embarrassing scenarios in life running from my gender truth. Examples came fast and furious during my initial days of trying to go public with my cross-dressing desires. Way before I acquired the knowledge to blend in with the world as a feminine person. Being in the wrong place it seemed was a regular occurrence. Both my male and female egos were suffering from be stared at, all the way to putting up with out and out laughter.

At the same time, I was feeling deep down that I was in the right place at the right time anytime I cross-dressed as a woman. I had not realized at that time that along I was a woman cross-dressing as a man. Which would have saved me a tremendous amount of heartbreak in my life. In the meantime, I needed to be content with just following my gender path the best I could, being aware of the many blind curves and stop signs I would run into. Such as the times when I was learning the proper etiquette that I needed to use the women’s restroom. For the most part, I did well with very little pushback except on rare occasions I remember to this day. The worst one that I always recall was the night a ciswoman followed me into the room and started calling me a pervert when all I was doing was trying to do my business in piece. Fortunately, she was the exception rather than the rule and I never had to go through anything so dramatic such as that again. Except for the time I was on a bus tour through the deep south with my wife Liz and we stopped at a rest stop on the Alabama border.

I thought everything was going to be fine until I was washing my hands and turned to face two women glaring at me. I quickly thought that I was certainly in the wrong place until I stepped around both of them and headed as fast as I could for the bus. I was certainly in the right place to take care of my business and at the wrong time with those two women.

The more I went out in the world as a transgender woman, naturally, the more chances I had to climb out on my gender limb and take chances to see how I felt about being there. Every time I did not fall, my confidence grew stronger to put myself in more challenging situations. In the retail world, I got myself out of the clothing stores where I was a non-entity and went to the world of bookstores and coffee shops to see how I was accepted. At the same time, as I always mention, I left the gay bars I was going to all the time and went to straight venues to see if I would find myself in the right spot at the right time. I was overjoyed when I ended up as an accepted regular at several venues I chose where I could enjoy everything from the music to the beer and my sports on big screen televisions.

I was never raised to be happy or satisfied with anything I ever did, so I was surprised at how satisfied my life was becoming when I followed the correct gender path to becoming a full-fledged transfeminine person. Casually living my new life, the same as any other ciswoman would do it. I even discovered that I had been in the right place at the right time with my sexuality as I fell into a group of women who accepted me totally and being with a man was never anything I ever had to consider.

The more I did as a trans woman, the more I never wanted to do again as a man, so I stopped because I began to feel so awkward on the rare occasions, I needed to re-enter the male world I used to be so good in. In fact, I just hated going back. Which was the time that I started to get it through my stubborn head that I was never destined to be a man at all and my right place was as a woman.

 Once I arrived firmly in my right place there was no turning back. Out went the old male clothes to thrift stores and in came the daily routine of what I was going to wear in the feminine life I always dreamed of. It had been a difficult gender journey complete with approving and disapproving people in the world but somehow, I always seemed to separate the haters and TERFS (Trans Exclusionary Radical Feminists)  out, learn from them and move on. Common sense finally prevailed as I chose the only lane I could and stayed in it. Many times, it was my own lack of confidence which stopped me from taking the steps I needed to survive.

As I said, being in the wrong place at the right time did not have to be the theme of my life unless I let it. Once I corrected a lifetime worth of errors, I was able to see the light at the end of the tunnel, and it was not the train. My train was still coming to take me to a transgender dream life I never imagined I could live.

Thanks to all of you who take your precious time to read and comment on mine. Without you, none of this would be worth it.

 

 

 

What Goes Up Must Come Down

 

Image form Vicky Hladynet
on UnSplash. 

Gender euphoria for me has been a double-edged sword.

The sharp edge of the blade has been the powerful elixir I gained from when I was successful in my early attempts to cross-dress successfully and enter the world. I was well aware of the feelings from my initial view of myself as a perceived pretty girl in my home mirror. Well before I had the courage to leave the house.

On the other hand, the dull side of the blade was the quick coming down I needed to go through after my successful journeys into the world of ciswomen and cismen. But I found early that the women were the ones I needed to concentrate on because they were curious about me. Ciswomen were the most likely to pick me out of a crowd and notice that I was not all that I seemed to be.

To combat my severe ups and downs, I needed to set up and stay on a steady diet of cross-dressing activities. To do my best to always have the joy of gender euphoria to get me by the worst of my gender dysphoric issues. Often, my rhythmic cross-dressing adventures were the only thing which kept me going in life when I became so depressed with a fatalistic “Why me” mentality.

As I learned later in life from one of my therapists, I was a bi-polar depressive which added to my problems of feeling down. When I was down, I was really down and had to force myself out of bed for days at a time. When I got the professional opinion about my depression issues, I was relieved because it was one less thing I could blame on my gender issues. Then I could concentrate on my sword again along with its ups and downs. What I did was expand my ups by doing more when I was out in the world exploring to see if I really was a transgender woman or a serious cross-dresser or what.

When I was out at the bigger shopping venues in nearby Columbus, Ohio, I learned I could be accepted as just another well-dressed feminine shopper looking for gifts from the specialty stores, I went to. Perhaps because I was trying to soothe part of my guilt of not telling my second wife what I was doing, I always tried to buy a little gift for her from one of the big gardening stores I knew about and visited. She was a very dedicated gardener and for a change I could make her happy. Along with me at the same time. At least I was trying to do something positive with my gender euphoria before I started to go home and crash back into my old unwanted male life.

Sadly, after I crashed, I wanted more of my feminine world and when I did not get it I tried to internalize my feelings which only made my life worse. Since I was suffering, I was selfish and wanted everyone around me to suffer too. It got so bad that I nearly lost jobs over my attitude and probably should have lost my marriage too, if my wife was not so strong. That also had its good and bad points. The good was that when we were good, we were very good and when we were bad because of my gender dysphoria, we were very bad. Mainly because my wife had everything as a woman that I envied and I resented her for it. The worst part was she should not have had to suffer along with me on my path of severe ups and downs because I was incapable of explaining either the ups or the downs of my life when I had them. One thing was for sure; the worst move I ever made was internalizing my feelings from my second wife.

To help my ups, I continued a serious program to learn if I really wanted to risk my life as I knew it to live a transfeminine life. How could I risk all that I had built up as a man for such a selfish move which would have far reaching effects past just me. Including my marriage, my family and my employment which were all doing well except for my marriage. I felt as if I was on a run-away train on a dead-end track with my life if I ever faced my truth about who I really was.

At the same time, my downs just had to be worth all the ups I was experiencing. My gender tipping point was rapidly reaching the critical point of no return as I was increasingly carving out a new and exciting life as a trans woman. My confidence was staying at an all-time high and suddenly my dreams might be able to become a reality. The only downs I was experiencing happened when my wife was still alive and I was feeling like I cheated on her with myself every time I snuck out into the world as the new me. I think deep down, I knew our relationship was not going to be sustainable, but I never thought it would be because she would die ahead of me. Naturally, her death hit me hard and at the age of fifty-five I was going back to my drawing board. This time to do much more than re-work how I looked as a woman. Now I needed to determine how I wanted to live out the remainder of my life.

Even with the obvious answer staring me in the face, I managed to still ignore my reality and stumble forward with one foot firmly planted in each of the binary genders. Finally, my male foot began to slip, and I quit fighting the obvious. I was never meant to be a man at all, and I was a woman living a lie and living like a man. When I did, almost all my depression went away, and I was free to live the life I was always destined to live.

As always, thank you for reading along with my lifetime of gender experience. I hope I can help you and comments are appreciated!

 

 

 

Is It too Early for Halloween?

 

Early fall Image
JJ Hart

As I look around the neighborhood I live in, I see people putting up their Halloween decorations already.

Then I began to think of the supposed “good old days” when about this time in September that I was starting to seriously consider what “costume” I would wear and how could I maximize its use by going to as many parties as possible. It just did not seem fair to me that I had to wait for a once-a-year party to express my feminine side without the fear of retribution. The worse that could happen to me were the other women at the party asking me who helped me with my makeup and did I really shave my legs for one night.  I was learning a valuable lesson about how curious ciswomen could be when you cross the gender highway into their lane.

Basically, my biggest decisions came as I thought about which theme I would follow year to year if I was going to the same party. And how creative could I be with my “costume” Ironically, my first big attempt at dressing feminine at a Halloween party came when I was still in the Army in Germany, when I was invited by my future wife to go to a hospital’s party. I had a couple of other wild friends who had their costumes already picked out and were coming as various forms of the male and female anatomy. So, I thought it would be an ideal time to fall from my cross-dressing wagon that I had been forced to be on for two and half years and come as a trashy prostitute.

I do not remember now how I got the clothes I needed to complete my outfit, but I was able to put together a short mini dress, long blond wig, hose and heels for a very effective costume. Since I still had approximately six months to go in the Army at the time, I was happy that no one seemed to care that I was dressed as a woman at the party.

When I was discharged from my military duty, and Halloween rolled around, I had a different challenge to face with all the newfound freedom I had. One thing I did was get away from the prostitute look and try to find a way to find a “costume” like what a ciswoman would wear.  In other words, I wanted to go to the party and try to pass as another woman enjoying herself. During the first multi-party Halloween night I went to, I think I did well. I went as one of the French girls I had seen in Paris when I was in the Army and brought the look home with me. I paired a all-black outfit which featured black tights, mini skirt and leotard with my blond wig, red lipstick and topped it all off with black flats and a black beret.

I was having a very good time entertaining myself in one of the big local clubs I went to which was having a Halloween party when a guy in a full mask approached me and simply said “I know who you are.” At first, I needed to recover from his comment before he went on to say, “I know because you look just like your mom!” Then I knew who he was and did not know whether to be flattered or not before he did not say anything else and went on his way. I did know I looked like mom but not that much.

From then on, I began to build my Halloween “costumes” from scratch and only used my many trips to thrift stores to help me with items for what I was going to wear. All I really knew was that I enjoyed my self immensely in my new world as a transgender woman and wanted to see if I could take it past the party scene and into reality. There would be other significant parties I will write about later, for now I had to learn if the build up to Halloween was totally worth it. I learned it truly was because of all the early lessons I would need to learn if I was ever going to decide to try to cross the gender border and live full-time as a transfeminine person.

I also realized that Halloween would be just the briefest thrill in what would be a long life of gender discovery. Would the overall gender euphoria of making it through the parties successfully be worth it when I had to crash back to reality and my increasingly boring male life. Plus, I found it was unbearable for me to just wait a whole other year to experience my feminine side again without me going out in public. I took my gender life into my own hands and began to explore the world in malls and outside in different venues such as bookstores which helped me build my confidence as a novice trans woman.

I went further, quicker than I ever thought I could and forever put Halloweens behind me as a necessity in life and more of a fun pursuit. In its place, I would be trying to carve out a brand-new feminine life of my own. It was the beginning of the most terrifying yet exciting time of my life. Mainly because I was stripped of all my old male protections and had to start all over again in a world where I did not know who to trust. Including myself because everything I knew was changing when I left the good old boys’ club for good and applied for membership in the girls’ club that I had so long waited to join. I was just at a point where I needed to convince ciswomen around me that I was serious and brought different qualifications to the feminine table. I had to suggest I was a woman too but just had been socialized a different way than they had been.

In many ways, Halloween was the earliest part of my socialization process thanks to the early interactions with ciswomen (and men) that I experienced. Immediately, I found that men I had known for years ignored me as a potential cross-dresser or whatever they thought I was. It did not matter. I was out of the club.  While at the same time, women I had known for years were curious about me. Lessons that had carried with me well in the learning years to come.

That is why I will forever miss the early excitement I felt around my early Halloween parties and why I still feel the fun I felt when I see the neighbors putting up their decorations early. Who knows, there may be a person in the family with gender issues also.

 

 

 

 

 

Transgender Journey...Down but Not Out

 

Image from Alexander Grey
on UnSplash.

As transgender women and transgender men, it is easy to feel down and out as we try to navigate our new gender paths.

As I sometimes look back on my journey, it is easy to remember the good times and forget the bad. The most important thing about reliving the bad is having the appreciation for the world I am able to live in today as a fulltime trans woman. Every time I make simple trips in the world to the doctor’s, the Veterans Administration or the pharmacy, I always have to look back at remembering the not so good old days when I was struggling for acceptance. Either one of a couple things has happened. Either I have become better at my overall feminine presentation (wrong) or my confidence has taken me to a point where I don’t particularly care what the world thinks about me.

Either way, I look back to when I considered myself a very serious cross-dresser as I still was researching which fork in my gender path would I take. Back in those days, I took hours to prepare for an outing in the world, and I often wondered what I would do if I had to go out in the world everyday and compete with ciswomen everywhere. It was easy at that time to put those thoughts behind me as I was so obsessed with my feminine looks that my second wife kept calling me the “Pretty, pretty, princess.”  Naturally I loved the “pretty” part but rejected the “princess” part of her very pointed critique of me. One day, she even went as far as separating appearance from being a true woman for me when we were fighting about me wanting to go out. It was one of my all-time down moments when she told me I made a terrible woman. It hurt because I was not trying to make anything, I was just trying to express my true self, but I could not properly put my thoughts in a form she would understand.

I guess you could say, back then, I was definitely in my mental transgender formative years when my mind was trying to catch up with all the cross-dressing I was doing. Sadly, before I could formulate what a better version of my transgender self would be, all I experienced was an extreme amount of frustration. I could not understand what I was doing wrong when I was being successful in situations such as transgender-cross dresser mixers I was going to. The problem was the extreme gender euphoria I experienced at the mixers when I was mistaken for a ciswoman was not worth the resultant crash and depression, I felt when my life went back to its same old boring male self.

It all resulted in me being boxed into rarely getting out of my gender closet to explore the world and I was moody, resentful and not the easiest person to live with as I tried to internalize my gender feelings from my wife. A prime example was one year when we took a vacation from our native Ohio to the Upper Peninsula of Michigan. On the trip up there, I progressively grew more depressed and mean until my wife asked me what was going on since I was supposed to be having a good time on vacation. Predictably, I lied my way out of it and did not tell her the truth that I rather be spending my vacation time as a woman rather than a man.

Somehow, I pulled myself back together and the vacation continued without incident, but I remember it as another low point. Little did I know at that time, destiny would finally come back to me on my gender path, and I would get my wish to go on extensive vacations as a transfeminine person.

Along the way, I have had many other low points which I write about often. Such as when a woman called me a pervert for simply using the women’s room in a venue, I had been a regular patron of for a long time and had no one say anything negative to me at all. Then much earlier than that when I was struggling to blend in with the world at all, there were all the stares and even laughter I needed to put up with on my journey to present. I was reduced to tears more times than I care to remember mainly by groups of teen girls struggling to find their own femininity. I was certainly at a low point when all of this was happening to me, and I did not have the tools yet to know which way to turn. All I had was this little voice in the back of my head telling me to keep going and my low points would disappear.

All of it did go away for a while until I hit my dark age when nearly everyone I cared about decided to die within a two-year period. The group included my second wife and three of my closest male friends. Who were the only ones I had. To add to my low point, I was desperately lonely and ended up relying on that little voice who at this time was growing louder and more insistent that she had all the answers for me. This time, I had very few other alternatives to fall back on. As one person told me after I had lost my restaurant along to everything else, you will land on your feet. Not knowing my feet would be in high heels when I did it.

I am sure that everyone’s lives have its share of highs and lows and I can not say a transgender woman or trans man lows would be even more dramatic, but it seems possible because we have so much to lose as we pick up our lives and move them across the gender border. Until we find ourselves living behind the gender curtain where we always wanted to me.

Hopefully if you are in the midst of a low time, you have a little voice telling you everything will be OK. If not, remember life is but a circle and what is down will eventually come up.

As always thanks for reading along and comments are always welcome.

 

 

 

The Age of Gender Innocence

 

Image from Nicola Dowie 
on UnSplash.

I used to think that my initial days of cross-dressing were the most innocent days of my life. I was very young and the feel of the feminine clothes on my body and the expectation of seeing myself in the full-length family mirror brought me to the height of anticipation. For the moment at least, I was putting aside all the worries I had of ever being able to live successfully in a male world.

Now, with the benefit of age on my side, I wonder if I was ever so innocent. Sure, I loved all the things about being a cross-dresser such as shaving my legs and wearing panty hose, all the way to feeling all the sensations of being able to wear the same pretty clothes I had seen the girls around me wear. The biggest problem remained was that just the wearing of the clothes was never enough. The thrill I felt of dressing up was guaranteed to only last a couple of days before I could not wait to do it again. Even my young mind knew there was still something wrong.

What was wrong was I was not a cross-dresser at all; I was a transgender woman waiting her turn to live in the world. In the meantime, I would have to depend on the temporary thrills of mirror worship to get me by in life. It all set me on a very long path of gender discovery. Complete with many ups and downs along the way to make the journey either very scary or at least very interesting. It took me years of mirror living before I could ever gather the confidence I needed to finally conquer my fears and go out into the world as a novice trans woman. Of course, there were the on-going challenges of learning makeup as well as shopping for my own clothes on an extreme budget. When I discovered the thrill of shopping at thrift stores, I was able to find clothes that fit me well by having the chance to try them on before I bought them. If I made a fashion mistake when I got it home, it was not such a big deal because it did not cost that much to start with.

Rapidly, my days of gender innocence were fading away as I became more involved in the world of ciswomen. I quickly discovered their world was much more than just the external world of fashion, hair and makeup. Their world was so much more complex than a cisman’s I was not prepared for it. I found I had a lot of work to do to be accepted at all. To prove I belonged there at all, the first step was to prove I was serious about doing it. I would first have to prove to other women, I was not trying to enter their world as some sort of a dare, or that I was not up to something no good. I desperately wanted to cross the gender border and join the girls’ club and leave the men’s club forever. When I was able to, entrance behind the gender curtain opened for me like never before.

It took many times behind the curtain for my innocence to really go away. I needed to battle my paranoia with being shy to start with and then having to communicate on a whole different level before I could relax at the girl’s night’s out I was suddenly being invited to comfortably. And that was not the only one thing I needed to deal with. Such as how I would ever dress to blend with the rest of the ciswomen in the group I was invited to. I certainly did not want to embarrass myself by dressing too much or not enough and finding that special point where I blended right in. My innocence was real, since I was dealing with a world I had never been in before, but the pressure was real because I wanted to make it a success so desperately. I can compare the experience to first dates I went on with women I did not know well as a man. How would I start the conversation and what would I say.

It turned out I did not have to worry that much because the group conversation was easy to follow without men around. It flowed around family basically and the relationships the women were having with their men. I just flip-flopped my past life as a man to one of a woman. Being purposely vague about key issues such as not having the birth of my daughter but I was there when it happened. My communication efforts seemed to work with all but one woman who just glared at me. I ignored her glare and stayed in the conversation and got invited back.

As I experienced more of the world as a trans woman, the more my innocence went away. Sure, I encountered the occasional toxic woman or TERF but with my confidence level soaring I was able to handle most all of them. If you are wondering why I have not mentioned any men, it is because there were so few of them. For the most part, they knew I had left the men’s club and wanted nothing to do with me, Plus, I cannot take all the credit for my success I had a very tight knit group of women friends around me to support me too.

Perhaps the most lesson I learned about gender innocence was the amount of difference there is between the two main primary genders. Basically, I learned that men operate on some sort of a power matrix. When they are challenged, they are less likely to give you a chance unless there is something in it for them. Women, on the other hand, are much more open to the world. Especially when it comes to their sexuality, which is not as frail as a man’s.

As I always say, if you are just starting up your gender path, be prepared for a change in your innocence as you enter the world of your preferred gender. And thank you for reading along as I described mine.

 

 

Just Another Lonely Day

Image from Jarge Johansen
on UnSplash.

Throughout most of my life, I was desperately lonely, as I had no one to fall back on as I explored my gender issues.

Growing up in a rural area, I started with just a
small circle of kids I interacted with and it rarely grew significantly, so again I was stuck with why I felt the way I did about myself. All I knew was I had a difficult time interacting with the boys at all and the girls seemed as if they were some unreachable magical creatures I knew nothing about.  While all of this was happening, all I could do was carve out my own little world where I was a pretty girl in front of the mirror in mom’s clothes and makeup.

Little did I know how those humble cross-dressing beginnings would come back to influence my life later. In fact, forever. As I grew, I became more skilled in using makeup and finding clothes which I could fit into when I outgrew moms. Then, the more I cross-dressed, the more I wanted to. Which did nothing for my extreme loneliness. It seemed to me; I would never find a way out and really did not until I hit my late high school and college days. What happened was, a group of girls at high school learned that a friend of theirs did not have a date to the junior prom and I did not either and matched us up for the evening. After a successful date, I was not so lonely when another friend of mine set me up with a single girl he knew and suddenly, I was a socialite as I entered college. In truth, deep down I was still the deeply conflicted person I always had been.

Amazingly, my early college years were so intense that I forgot about my gender issues for six months or so before they crept back in. When they did, they became as intense as they were before I left for college and stayed that way until they were put on my back burner when the military draft caught up to me when I graduated. For a while I was engaged to a woman I knew from college until she left me just before I was due to report to Ft. Knox for Army basic training leaving me completely alone again. When my fellow soldiers were getting mail from wives and girlfriends, I was getting an occasional letter from mom. At the least, I appreciated her efforts and once again I was back to being used to being intensely alone.

All along I wondered what my military time would do to my gender issues. Would they go away temporarily like they did in college or not was my question. The answer I was looking for did not take long to become evident to me. No my gender dysphoria was not going away and in fact, tools I had learned in the Army just made my dysphoria stronger. For example, I became more confident in myself as I had a better idea of what I could survive and I spent hours of what spare time I had daydreaming of what I would do with my feminine self once I had served my three years.

It was not very long after I was discharged that I gathered the courage to ask my first wife to marry me. Since she was in the Army too with me for over a year, she had witnessed my Halloween party costume at a hospital party we had went to with friends. Plus, my later confession to three friends plus her that I was actually a transvestite and my costume went a lot deeper than it looked. She also turned out later be the mother of my first and only child and the marriage did last several years until I fell madly in love with my second wife.

Oddly enough it was another Halloween party which allowed me to confess to her my deep dark secret that I was a cross-dresser. It turned out that she did not care which was the case for the twenty-five years we were married. Until I began to transition into a transgender woman. Just before she passed away from a massive heart attack. During those years we had our share of good times and bad times somehow, we always made it through, and she never knew how much of a role model she was to me when I went my separate way as a trans woman. Following her untimely death at the age of fifty.

When she passed, I went into a lonely shock I had not felt through the majority of my life. I could not understand why I was having to start all over again in my mid-fifties and search for another relationship. And furthermore, which direction would I take with the gender issues I had during my life. By this time, I was well ahead of my goal to possibly live as a transfeminine person. I had major decisions to make in my life, so I kept on searching for answers. To start with, I tried dating ciswomen again as a man which failed miserably and at the same time, get more serious in my explorations ss a trans woman which I found to be a natural social release for me.

By the time a couple more years of wasting valuable time went by, I was sitting by myself enjoying my new company and I thought why was I not living like this all the time? How stupid could I be not to take advantage of what I had learned in the world so far as a transgender woman. Most importantly, my lifetime’s dream of living as a woman was within reach, and I was not taking advantage of it.

From that point forward I put together a timetable to give away my remaining male clothes and pursue HRT therapy. There would be no turning back from that point forward. I was tired of the gender struggle and loneliness I was enduring. I was afraid if I did not make the change now, I never would have the chance.

You might say I played the odds and they came out in my favor but on the other hand, I researched the odds extensively before I did it.

 

 

 

I Wish I Knew Why

 

 

Image from Jon Tyson
on UnSplash

It has been a while since anyone has asked me when I knew I was transgender. In fact, it was several years ago when one of my grandkids was coming out to my daughter as being trans.

My daughter then asked me if I had always known, true? I told her yes that was true except in the exceedingly early days of my life when I knew something was wrong with me but I just did not know what. As I grew older and I experienced that first magical visit to mom’s clothing drawer did I truly knew what the problem was. I really liked the feel of mom’s clothes and that was only the beginning as I wanted to be a girl full-time sometime in my life. Just the buzz of wearing feminine clothes was never going to be enough. So, I set out on a long journey to see if I could ever achieve my dream.

When I was able to begin to interact with others with gender issues, I found early on that it was not going to be the end to my questions that I thought it could be. For example, I was too much girl for many of the cross-dressers I met and not enough woman for the then called transsexuals I encountered in person at the social/mixers I traveled to. The closest ones initially were nearly a two-hour drive away before mixers were then set up in a nearby central location for me. It was then that I was able to meet others who identified as true transgender women and I fit in perfectly with them. Finally, I began to have answers to my identity as a person.

Of course, I needed to take all sorts of side journeys as I sought out the key to why this transgender world had chosen me. In my research I even came across the theory that the drug “D.E.S” which was given to women with a history of problem pregnancies around the time I was born, could conceivably be linked to a person having= gender issues later in life. Because to ensure the fetus went full term in the womb, the womb was flooded with estrogen to aid the birth process. I thought “D.E.S.” might fit me because my mom had suffered through three still births before I came along. Ultimately, “D.E.S” stayed just as it started with me. Another solution to an extraordinarily complex gender problem with no concrete answers.

Then there was the victim mode I wrote so much about when I went through a poor, poor pitiful me time of my life. I could not understand why I needed to be stuck with all the gender issues I had when no one I knew had them either. To this day, I envy men who have been able to go through their lives as men without the added distraction of wanting to be a ciswoman. Finally, I made the difficult turn considering my overwhelming desire to be feminine as a good thing. Because it set me off from society as a unique person with a look at both sides of the gender border. Removing my victim mentality made all the difference in the world to me as I began to look ahead for the possibilities which laid ahead. Rather than always looking over my shoulder and dwelling on the mistakes I had made.

The more success I experienced when I first was able to carve out a new life for myself as a transfeminine person, the more the wish I knew mentality I had lived with my whole life began to fade away. From that point, I went into my confidence mode because without it, I was powerless to do anything I wanted to do as a trans woman. I found that as long as I held my head high and did my best to be a quality person in the world, the more people left me alone since humans are like sharks. They sense blood in the water, and I was not adding any of mine. Confidence also allowed me to try different things. To judge if I really wanted to jump the gender border and give up living life as a man altogether. Even though it was the most difficult decision of my life, having even a sliver of hope that I could live my dream that propelled me forward to a gender tipping point that so many ask about.

This time, I could tell anyone who asked why I decided to leave a successful male life to take on a decided uncertain one as a transgender woman. The answer I always gave was deceptively easy. I had reached my own gender tipping point where I was living more as a woman (and feeling natural doing it) and less as a man as I was feeling increasingly uncomfortable doing it. By doing as much research as I had, I had given myself no choice as what I should do. When became now and that was the time, I decided to take the next step and pursue gender affirming hormones or HRT to sync my inner mind with my external body the public saw. I knew it was the point of no return for me as my body took to the new hormones magically.

I knew from there that all my explorations as a trans woman pus the addition of HRT allowed me the most powerful female privilege of all. The power to finally be myself. The wish I knew why I was different my whole life was answered with a resounding yes, I did know it all along and refused to face my own truth. I was living a counterproductive life as I was going overboard trying to be successful as a man when I was a woman forced into her shell all the time struggling to get out. The best part was when she said I told you so, as she destroyed what was left of my old male ego.

I finished strong when my why me became a why not as I had the chance to live my feminine truth among the ciswomen of the world.

Thanks for reading along and I hope you will discover your why me in life! Comments from you are always welcomed.

 

 

 

 

Labor Day 2026

 

Pik Nik with JJ Hart (left) and wife Liz. 

Time flies when you are having fun, especially when you are just getting older in life. Once again, another Labor Day and summer have come and gone. It’s like my mom used to say, life is like a roll of toilet paper, the closer to the end it gets, the faster it goes.

Around here in Southwestern Ohio though, we are entering what is called “Indian Summer” with temperatures which remind us of August. So, most of the fall fashions we have purchased will have to wait for another month until October rolls around.

Fall has always been my favorite time of the year as the leaves of the trees begin to change their colors, football is in full swing and I get to go through my fall and winter wardrobe to see what needs updating. It is one of the joys of living in a climate which still changes four times a year. In many ways, it seems like only yesterday when I first experienced my first summer to fall fashion transition as a transgender woman.  I thought now I was finally going to get to experience all the pretty clothes that ciswomen get to do. In a sense that was true once I could afford to update my fashion and find the proper sizes which fit me. To do so, I wore out my shoes going to thrift stores looking for fashion bargains which flattered me.

Of course, I forgot to mention the cross-dressers’ national holiday, Halloween which gives us the chance to flaunt how good we can look like a woman. Often for a neutral audience. I know for me it was the first time anyone saw me as myself outside of my mirror. For the first several serious Halloween parties of my adult life, I experienced the good and bad of being in public as a trans woman or even a novice cross-dresser. The good part was that I think I was successful in presenting as a woman while having the freedom to do it. However, the bad part was having to wait an entire year to do it again. Finally, I could take it no longer and needed desperately to take my feminine show on the road and head out to the malls unattended.

Once I began to try to get out of the mirror and into the world as a trans woman, Halloween just became the icing on my cake as my so-called “costume” changed from shock value trashy all the way to professional ciswoman ideas designed to see if I could fool people I did not know. No pun intended, but I made the transition from trash to class quite easily and I loved it. It gave me the direction I needed to go forward in my male to female femininization journey. I will be presenting more of my Halloween adventures as we get closer to the actual date of the holiday.

Sadly, not all my memories of fall are good ones. I vividly remember the nights I drove around alone seeking answers to my confused life which basically revolved around which gender was I and what was I ever going to do about my upcoming date with the Army. The rapidly blowing leaves in front of my headlights only reflected the despair of my life at that time.

So, that is why Labor Day represents more than just another holiday to me. As I said, the holiday makes me feel deeply about beginnings and ends as nature starts her transition from summer to winter and calls it fall and gives us brilliantly colored trees and cooler temperatures to enjoy.

Just a short Labor Day post today celebrating the beginning of fall around here. No matter where you are, I hope you can celebrate it too!

 

 

 

I Wanted it All

 

Image from Sindy Sussengut
on UnSplash.

During my gender journey through multiple transitions from cross-dresser to transgender woman, I have been selfish and wanted it all.

It all started very early when I was experimenting with mom’s clothes and makeup when I had the first idea all that I was doing may go deeper than just wearing feminine clothes. I did not have the terminology or knowledge back then to work my way through it, but in reality, I was discovering I was more transgender than anything else. In the years to come, that would be a major point to think about along my gender path.

As I grew through my first two marriages where both wives knew of my cross-dressing desires, my first wife was far less demanding than my second and on numerous occasions during fights we were having about me, my second wife rightfully pointed out that our relationship was not all about me. Since I was in the middle of an obsession with my appearance and all things related to makeup, as I said she was right and I was needlessly selfish about our relationship. She was far wiser than I and knew even at that early time in our marriage, her husband was slipping away.

Even though I loved her dearly, I still could not stay away from the powerful draw of wondering if I could ever achieve living fulltime as a transgender woman. Deep down, I knew my second wife would never come with me on my journey as she made it abundantly clear she never signed up to be married to another woman.

With a lot of work and repetition, I did finally get better with my wardrobe and makeup and then needed to figure out how to sneak out of the house and get into the world. It basically meant my imagination had to go into overdrive as I tried to think of reasons I needed to explore the world as my new true transfeminine self. Even if I was not sure what the word meant back then. I went as far as going to the grocery store for my wife who was working on the days, I was off and combined the trip by going to a nearby big box store to shop for panty hose and makeup. My biggest takeaway came when I noticed very few people were noticing me and I started to think I wanted to experience more. My restless feminine spirit was dominating me again.

At the same time, I was doing all of this, I was still searching for my dream job in the commercial restaurant business and after switching jobs and locations several times, I finally did. As I finally broke free of my fast-food background and landed a job with “Chi-Chi’s” Mexican Restaurants in the Columbus, Ohio area where I had ties to. It was a win-win situation for me because I was back home again and could start to interact with the diverse small LGBTQ group that I had known from years previous. This was the tight knit group that had several transgender women who were on their ways to gender realignment surgeries, and I could pick their brains on what it meant to do it. Even though, I did not have the resources or the willpower to consider such a radical move for me in my future, Just being considered as an equal in their group was good enough for me…then.

I say “then” because in life everything rarely stays the same. As I continued to break the vows I had with my wife, I kept going out to venues from the house and began to actually carve out a life as a transgender woman with people who had never known my male side. Wanting it all was staring to mean so much more to me than ever before as my male life began to slip away from me and wanting it all increasingly meant an ongoing break with my long-term marriage of over twenty years. Because she was not giving into her demands, and I was discovering just what mine should be if I was willing to risk it all to live my dream life. Sadly, it would have to be all me to do it as I tore down everything I had worked for as a man to start over in a woman’s’ world.

Sure, I was scared to death as I decided to keep concentrating on the feminine me who had waited so long to live her life. But the whole process and path I was on felt so natural, I decided to be selfish and continue it. By proceeding along the path I was on, I needed to take several abrupt detours when I had problems with deciding my sexuality all the way to just basically communicating with the remainder of the world I was in. Which I discovered was made up of ciswomen not so unlike my second wife. Many were strong and sure of themselves and set up forms of communication which were totally foreign to me as I was coming from a male world. Suddenly, I needed to adjust to forms of non-verbal and passive aggressive communications which were reserved for use when cismen were around.

Perhaps my best selfish move I made was to be approved for gender affirming hormones or HRT which enabled me to come closer to my transgender mentors of so long ago. Since I had ruled out any surgeries, the changes from the hormones would be as far as I could go to sync up my female mind with my male body.

By this time, my wife had passed away and there were very few people left who knew the old me at all. So, I was mostly all-alone with my new emotions and bodily changes such as hair, breasts and hot flashes. When I reached out to any of my lesbian friends, all they would say was welcome to their world. Little did they know how badly I wanted to be there. I was rewarded by the fact that the people who knew the male me told me they thought I was much more relaxed and happy now.

Since I can now love more deeply than I ever could as a man, my life has come full circle to encompass feelings I never knew I had before. All because of my selfish one sided past to get here. I wanted it all and finally was able to find it.

Thanks for reading along and I would be remiss if I did not mention two things. Thanks to Grace Ann Hansen for publishing my stories in her “Empowered Trans Woman” site!

And sadly, I would like to mention the passing of a true icon, Dolly Parton who was a staunch ally of the LGBTQ community. She will be severely missed.

 

 

 

 

Dealing with Gatekeepers

 

Image from Ries Bosch
on UnSplash. 

Unfortunately, all the people who see it as their job to be a gender gatekeeper can run the spectrum from nice to nasty.

The nice ones are just normally curious as to what you are doing in their world and will sometimes even help you come through their gate and cross the gender border you so desperately want. Then there are the other ones who sadly make a bigger impact in the world when they overstep their bounds and attempt to keep transgender women or transgender men from ever entering their spaces.

My problem with gender gatekeepers is who gave them the right to do what they are doing anyhow. I see the titles of woman and man as socialization words only. Meaning just because you were born female or male does not mean you are ever socialized enough to earn the title of women or men. I fear the ones who never deserved to be called a woman became the gatekeepers who are trying to stop us transgender women from ever achieving our socialization goal of at least being able to have a feminine life which includes entering spaces such as restrooms.

During my life, I have met both sides of gatekeepers. I have seen it all from being called a pervert in one women’s restroom to being helped to an empty stall in another. Then, there was the Lesbian Valentine’s Day dance Liz, and I went to years ago in Cincinnati. While Liz went up to the refreshment area to get us some appetizers, unannounced I was approached by this lesbian ciswoman who wanted to know what my “real” name was. She was nasty and naturally, I would not tell her anything about me because for some reason she took it upon herself to be a gatekeeper where she did not need to be.

Because I was completely and quickly kicked out of the men’s club when I transitioned, I did not have to worry about very many male gatekeepers. I still remember vividly attempting to join a conversation when I first came out between men when they were dealing with a subject, I knew a lot about and was quickly ignored. It reinforced in me how much I would not miss getting kicked out of the men’s club and sought out the company I really wanted which was with women. As I realized I had always felt that way and life had just got in my way as I always had been pressured to find and date a girlfriend as a male. Ironically, I was very shy and afraid to challenge the feminine dating gatekeepers to even ask a girl out. I finally overcame my internal gatekeepers with the help of friends who set up dates for me with unattached girls they knew.

As I began to explore the world increasingly, I began to meet and utilize more feminine gatekeepers to my advantage. I started to realize how much more ciswomen were secure in their sexuality than cismen and were not afraid to interact with me. Plus, when they went out of their way to do so, at the same time it gave me a chance to learn so much more from them. With men, if most of them even talked to me, they felt somehow, they were gay. Again, I was happy the male gatekeepers kept me out.

Then, let us not forget the most extreme gatekeepers of all, who are the TERFs (or Radical Feminists) who have even teamed up with groups of Evangelical Christians to keep transgender folk from crossing gender borders. There is nothing I dislike more than having a so-called Christian tell me they will pray for me as they jump on the gatekeeper’s bandwagon.  

Sadly, gatekeeping still exists in the gay and transgender community as the Log Cabin conservative Republicans have recently announced they would be taking the “T” out of their LGBT language. I always use them as an example of what will happen when the current administration grows tired of coming after a minority transgender community and comes after a larger gay one.

Even sadder yet are the transgender community members I have known over the years who have tried to exclude certain trans women for not having as many gender realignment surgeries as they have had to prove how trans they are. And they are nothing more than glorified cross-dressers. As if there was anything wrong with being a cross-dresser which most of us started their active transition to being a transfeminine person by experimenting with their mom’s clothes.  Who must say that in the future, the cross-dressing person you shunned may want to do more in their gender life and blossom into their full desired gender lives.

These days, with how divided the country is, it is so sad that so-called normal people are ready to jump into other people's business and become novice gatekeepers. Who gave the woman the right to call me a pervert or even transgender women chiding me for wearing pants too much and who needs to know my previous name except for me anyhow. I know all humans face gatekeepers in life, but it seems the trans community faces more than their fare share of people attempting to exclude us. To put it another way, I faced way too many four way stops on my gender path to finally living my dream, Seemingly, destiny had to show me the problems of living with then losing to death a disapproving wife all the way to losing friends and my brother when I transitioned across the gender border to be a happier person.

I guess I was lucky I wasn’t on a toll-road where the gatekeepers wanted a payment for passage. If I was, I would be broke by now and I was lucky to have received so much more than I lost as I carved out a new feminine life.

Hopefully, you can navigate your gates successfully as you move along your gender path.

Thanks for stopping by and sharing my lifetimes worth of experiences! Any comments are always appreciated.