More Than Just a Passing Fantasy

 

Image from Alexsy Turenkov
on UnSplash.

As I made my way into the public’s eye as a novice transgender woman, I needed to prove to the average person I was much more than a man in a dress with a wig and makeup.

It meant I needed to change my entire thought pattern too about who I thought I was because for the longest time, I considered myself more or less a feminine “hobbyist” who dabbled in wearing feminine clothes and makeup. I considered myself as serious about my hobby as much as I did my brother being serious about his golf game.

Ironically, I can not put my finger on the exact moment I started to change my overall thoughts on myself, but it was a gradual process. Triggered by me being exposed to the transgender term for the first time in my life. It all came from the fact that I knew there just had to be more to what I was doing with my feminine self than just a casual process and the transgender terminology appealed to me. Being trans took me another step towards living my ultimate dream of living as a transfeminine person more than anything I had ever read before.

All my research into gender dysphoria and its effects on me led me to slide myself increasingly on the gender scale to the feminine side of the spectrum internally. Which was the easier part initially. Then, all I needed to do was internalize my feelings and keep on living my male life so no one would notice that I was different at all. The problem was, I did not know how much internalizing my gender dysphoria would hurt me in the short and long term.

As I always knew, but tried to hide, just cross-dressing was never going to be enough for me, as I wanted to do more with my life as a woman. Of course, once I realized it, I needed to plan a course to do something about it. Being stuck in a restrictive single occupant closet was not going to be enough. Somehow, I needed to gather the two C’s, courage and confidence to take on the world as my authentic feminine self if I was ever going to do more than jut survive in the male world I wanted nothing to do with. I needed to get out of it and convince others I was so much more than some sort of a drag queen playing a part of a woman.

Little did I know, the drag queen problem would take care of itself everywhere but in the gay venues I was going to often. After I was done hitting my head against the wall in the gay venues, I decided to go back into the world once again to see if I could be viewed than more than someone’s fantasy object. Accomplishing it became easier to me than I ever thought possible when all I had to do was to keep going back to the venues I had frequented as a man but this time as a trans woman. If I managed to wear the same wig and look the same, I was hard to miss and easy to remember if I followed my basics of always being pleasant, never causing problems and tipping well. By doing so, I became a regular before I knew it and I started to carve out a whole new feminine life away from my male past. Most importantly, there were no passing fantasies involved for me, no smoke and mirrors as I was actually doing it.

I continued to take my trans show on the road, so to speak, as I tried to live every spare moment as a woman to see if my dreams were more than just dreams and not turn out to be nightmares. I was trying to make sure I had all my life’s basics covered if I was ever going to give up everything I had earned as a man. Use what I could as a transgender woman and start all over again. That way, I would not totally be starting over, I could take what I learned as a so-called cisman and apply it all towards the scary but exciting new world I was living in.

Doing the same things over and over as a woman helped me to carve out the new life I had always wanted to live. Other ciswomen knew my name and wanted to know more about my life because they were curious why I wanted into their world. I was in heaven and continued to want more as my life changed for the better. It all did because I had the courage to put myself out in the public’s eye. While I never managed to be the most attractive woman in the room, I was the most consistent with my look. Which was all I could do with what I had to work with in my testosterone poisoned body. It took me a lot of time and effort, but I put away all my old misgivings about my life’s journey and kept my momentum up towards my extreme male to female femininization project.

By this time, most all the family and friends who meant anything to me had passed away leaving me all alone in the world to do what I wanted. After all those years of playing around with thinking I was a casual cross-dresser had completely left my mind and looking like a woman was much more than a mere fantasy, I was ready to move forward into the world I had always should have been a part of. It turned out to be a for better or for worse deal for me by this time. I had put so much effort into the struggle to femininize myself and get out of the male world that it all turned out for the better as I entered a win-win situation in the world.

In fact, during my life, there was no way I ever could have fantasized arriving in the place where I had arrived. I love it when a plan comes together. Even though it took me so long.

Thanks for reading along with all my hopes and desires during my life.

Thought are always appreciated!

 

 

How Halloween Benefitted Me

 

Image from Jennifer Marquez
on UnSplash. 

In the recent past, I have written a couple of stories about my Halloween experiences but there were more which taught me valuable lessons about the possibility of following my gender path.

Such as the time I was able to set up a training trip down to my company’s headquarters in Lexington, Kentucky to coincide with my favorite time of the year which was Halloween. In those days, the fashion rage was very much into fake leather, and I could not wait to show off my new faux leather mini skirt and matching top at a Halloween party. To get ready for the trip from Ohio to Kentucky I needed to find private time away from my wife to pack two sets of clothes. One for my male presentation at the company headquarters and another for my so called “costume.” Somehow, I was able to find room in my suitcase for makeup and a wig, and I was ready to go. The lessons I learned on that trip were that I could indeed pack effectively for two genders.

Once I arrived in Lexington, the next problem I faced was figuring out where I was going to go to show off my new “costume” in public for the first time. Luckily, the hotel I was staying in had several different publications in the lobby I could look at to see if I could find any parties that may be close by. I did, and then had to try to find them, after I was cross-dressed and ready to go. I was nervous as I put on the only pair of black panty hose I brought with me and put on the padding I needed to work with to provide a feminine figure. Next came my makeup and a resurrection of my wig following its time in my suitcase put on my heels and I was nervous and ready to go.

Probably, the biggest challenge I was going to face was going from my room to the elevator then worrying about facing anyone else as I went down to the hotel lobby. I should not have worried because I did not see another person until I arrived at the entrance and the ones I did act like I was not even there. Then, I was off to find the venue I was looking for in a city I was not familiar with at all. Back in those days, there was not such an invention as a GPS to help me along but somehow, I did find the first big venue I was looking for. Lesson learned. Try to find out where you are going before you get there. On the other hand, I had a powerful motivation to get out of my closet and see if I could survive in a straight world of Halloween party goers as a novice trans woman.

When I arrived at the entrance to the venue, they were checking identification at the door and surprisingly, no one reacted to the person in costume as a woman with the obviously male I.D. My hand was stamped and in I went to an unknown experience which might change my life as all the other Halloween experiences had done.

As I walked in, the venue was already packed, and I needed to find my way to the bar for a drink and the closest route was across the dance floor. I took a chance and made my way through the couples dancing and up to the bar. Once I ordered my drink and was served, I started back to a relatively uncrowded part of the club to enjoy people watching along with the feel of my “costume.” It was then that I learned the lesson of what it was like to be a ciswoman in a crowded venue with potentially toxic cismen who could not keep their hands off of my rear. I have never been pinched and touched so much in my life as I made my way back to one of the rare open seats I could find. Lesson learned again as I headed off to another venue to experience more of my evening before it was time to return to my hotel in my faux leather outfit.

I did find one other place which was having a party, so I decided to make it a night by stopping in there also. The second venue on was far less crowded and mellow than the first one and I was relaxed and had the confidence from my first experience to go right in. I was met by a friendly checker at the entrance and again no reference was made to my male identification which was probably due to the magic of it being Halloween.

One thing I did not do was stick around in either place for their costume contest because I was so insecure about myself. I did wonder if I did join the contest and somehow won if all the men who were fondling me would have been properly shamed but probably not. All they pinched was foam rubber anyhow and I went on my way with another powerful lesson learned about how ciswomen are really treated. I wondered if I had not been wearing any protective padding would I have bruised the next day.

The biggest problem I had was coming down off of my gender euphoria rush to effectively teach the company management classes I was supposed to teach. I did not make the trip to Lexington very often and was never able to spend a Halloween evening there again. When I went, I was often stuck going out with groups of other male managers to strip clubs where I did not really want to go. While I admired good female bodies, I never had the urge to go any farther. I was always the first to leave the strip clubs which made for a clearer head in the morning from no alcoholic hangover.

Without the benefits of many Halloween experiences, I am sure eventually I would have made it to my goal of living a fulltime transfeminine life, but it would have taken me longer. I would have not had the “A-Ha” moments I had from Halloween when I was able to see why women are able to exist in the world the way they do, and I will never forget the lessons I learned from my favorite holiday.

 

 

 

 

 

There Was Never a Plan B

 

JJ Hart, Back row far left
Girls Night Out.

Very early in my cross-dressing days, I always tried to have a plan b in the back of my head if danger approached in the form of my brother discovering me or my parents coming home early from work.

Seeing as how I had no effective plan to get out of what I was doing in mom’s dresses and makeup, I thought that somehow, I would have to just try to lie my way out of it and say I would never attempt it again. Knowing that was a deal with the devil I could never make and expect to keep. As I continued to cross-dress in the family mirrors, I finally had to throw caution to the wind and just go ahead and do it.

Years went by as well as the complexity of what I was doing as I tried my best to express my feminine self. At the least, I thought of better ways to hide away my resources from prying eyes and was successful all but once when I got careless on a weekend, I was away when I was waiting to go into the Army and start basic training. What happened was, I had just mixed my feminine clothes and wig in with a bunch of my male clothes thinking that one would disturb them until I returned. I was wrong and when I got back, everyone else in my apartment had not returned home for a college break leaving me all alone except for one other guy who had come over to visit.

As we sat around drinking a few beers, I decided to gather my courage and somehow asked would he like to see me dressed as a woman. Effectively, throwing all ideas of a plan b if he got up and bolted out of the apartment. To my surprise, he did not and was receptive to the idea, so I left to start the prep work needed to finally come out to another person. After I had taken the time to shower and shave my legs and face, I went into my bedroom looking for my feminine clothes, wig and makeup. Only to be shocked to learn they were all gone. Someone had stolen them when I was gone. All the plans for the evening I had were shattered as we sat around and then finished all the beer and nothing was ever said about him coming so close to meeting the true me. As far as confronting anyone about where my clothes, wig and makeup had gone, I decided to keep my mouth shut because I was so close to having to report to Ft. Knox in Kentucky for Army basic training anyhow. A final solution for a plan b during the next three years of my life. I knew I could not entertain any ideas of cross-dressing at all.

When I was discharged and Halloween parties with my friends became the only external form of feminine expression that I had, I needed to ignore any of the warning signs that I was giving away any idea I was not as masculine as I acted. I was so into going to Halloween dressed as a woman that I decided to take matters into my own hands and ignore all the plan b’s that I had thought up. Even to the point if some other person commented on my “costume” and the effort which went into it, I would just try to laugh it off. Mostly what happened was compliments from other ciswomen on my shaved legs and I even gained the nickname of “legs” with several of them which I had to act like I did not care. When deep down inside I was overjoyed and wanted more input. It took me years to understand what they were really saying was I looked good for a man dressing as a woman.

As more years went by and I became very serious about being a transgender woman and was attempting to hide it from my second wife, plan b’s became very important to me. In many ways, I had regressed to my childhood in the ways as I had to hide my femininity away from her. In addition to being very tuned in to when she got off of work, I needed to get better and better at makeup and eye makeup removal, so hopefully she couldn’t tell what I was doing when she was at work. The problem was that practice was making my femininized presentation more effective.  Success just made me want more and having a plan b at all was disappearing totally.

For the longest time, the only recourse I had was to attempt to lie my way out of whatever transgender activities I even had to resort to trying therapy to save our relationship. The gender therapist was wiser than I was and told me there was nothing she could do about my deep-seated gender issues. I was trying to buy time with my wife and save our relationship as long as I could, but the therapist was not a miracle worker and I quit going. Leaving me to wonder what I would do about finding the next plan b I desperately needed to hold my marriage together. Because I knew it would be just inevitable my wife would discover what I was doing as a transgender woman exploring the world and we would have a gigantic fight because I had promised I was going to stay home.

The problem was that I knew I was wrong and was just buying time until the next adventure I had in the world with the ciswomen that ran it.

Finally, what happened was I ran out of all needs to have a plan b when it came to me being a transfeminine person. I had learned to live freely behind the gender curtain which I had waited so long and worked so hard to do. In fact, it was the only big dream I had in my life. I then resorted to a new plan to live out my life the way I wanted.

 

 

 

 

It's All in the Details of Gender

 

Image from Liam Nguyen 
on UnSplash.

Quite early in life, I learned to pay attention to the details when I followed my instincts and started to cross-dress into mom’s clothes and try to put on her makeup. I thought all was good after I had snuck around and managed to shave my legs again without anyone noticing.

That was until I snagged mom’s hose on an unkept fingernail and ran yet another pair of good stockings or pantyhose. I learned the hard way to take better care of my nails as well as the rest of my body on my path to femininity. Little did I know, paying attention to just the smallest of details would rule my world as I climbed my gender path towards my dream of living fulltime as a transfeminine person.

My major problem was that I was restricted to viewing what a woman’s life was like from the outside in a male dominated family. Through it all, my mom became my mentor and role model more than she ever knew and it went way past just using her makeup and wearing her clothes. I could see how she worked behind the scenes to make sure that the family ran as smoothly as possible. Way past all the traditional female duties such as cleaning and buying groceries. She taught me all that a ciswoman could be at a young age. All the time not realizing what she was doing because she actually had a daughter, not a son.

It was not until I began to get out on my own as a novice cross-dressing transgender woman did; I really have to develop my sense of detail. It was very difficult for me because I was never a detail orientated person. When I went out initially as a trans woman, there just seemed to be so much to concentrate on and remember to do to succeed. Even if I thought I had perfected my fashion, hair and makeup for the evening, there was the problem of putting it all together outside of the mirror and getting all my movements down, so I did not look like a linebacker in drag. The details weighed on me heavily and they were all I thought about in every spare moment I had. So much so that I needed to think ahead to which gender I was at key moments in my life.

It all carried over into life events such as weddings and dances when I had to step back and wonder what I would be wearing if I ever had the opportunity to attend as a trans woman. Sadly, I did get to experience attending a funeral when my wife Liz’s dad passed away after I had transitioned. I wore my best black outfit and did the best I could to blend in properly with all the other ciswomen who attended.

The funeral was just another reality check for me as I needed to face how far I had come in my male to female femininization journey. At my age, I always knew attending a funeral as me was a possibility, but I never knew how real it was until it happened. At that time too, reality and details were becoming increasingly important as I expanded my life in the world to new and exciting groups of strangers such as in spiritual circles and Meetups of writers in Cincinnati. They were the first groups of strangers that I had ever met outside of LGBTQIA+ support groups I attended locally and at the Veterans Administration in Dayton, Ohio. Meeting new people as I said was exciting and kept me active at an exciting time of discovery in my life.

By this time, repetition replaced my need for detail as my makeup habits, along with clothing needs became ingrained as I finally knew who I was in my life. No more searching in a dark lonely closet for an answer. I had it with the help of the world of new and exciting discoveries I was in. I had brief moments of releasing my gender euphoria before but nothing like this before as all the possibilities of the world were opened to me. When I sought out and was approved for HRT or gender affirming hormones. Which I write about a lot. New emotions outweighed the need for details as I moved ever closer to being the person I always wanted to be.

One thing I never forgot as I male to female transitioned was how I was treated early on and how I needed to respond by going back to my cross-dressing drawing board time and time again until I got my details correct. There was so much more to what I was trying to do than my home mirror had told me as I tried to exit my gender closet for good. All I knew was, once I was released from my loneliness, I never wanted to go back. I spent as much time as I could out in the world working on my feminine presentation so I could overcome my testosterone poisoned body and make it.

I cannot stress enough how much of my journey has been filled with fear and or panic when I lost key male privileges such as intelligence and personal security. Details just weren’t enough to help me through all the anxiety I felt meeting strangers in my new exciting world. In fact, just yesterday, I felt the same old twinges of panic sneak in when Liz’s son and I had to take our old lawn mower into the shop for a tuneup. After all these years in the public eye and I still have the same problem is ridiculous I know, but I still do when I am entering predominantly male spaces for any reason. Again, all went well as the young person at the mower place was only interested in taking care of us. Not my gender.

All in all, the extreme work I put into crossing the gender border was worth it as I achieved my goal of living the life I wanted to live. Even though there were times when I did not think I was going to make it.

Thanks so much for joining me with my life experiences. Hopefully you can gain some insight into your life from them. Comments are always welcome!

 

In Praise of Transgender Men

 

Image from Aiden Craver
on UnSplash. 

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

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

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

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

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

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

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

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

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

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

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

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

 

 

Gender Binges

 

Image from Andy Arjun
on UnSplash.  

Binge cross-dressing happened a lot to me when I was quite young.

Once I was able to scrape together my meager finances to put together a small wardrobe of feminine clothes that barely fit me, I could not stay away from wearing them more and more. In fact, I was able to come up with two main hiding places away from the prying eyes of my family and most importantly, my slightly younger brother. It was about that time that I really became involved with binging in my new clothes which I felt made me look like a pretty girl.

Very soon, regardless of the risk involved with me cross-dressing as a girl, I was doing it as much as I could get away with. I think now that my mom had to know something about my cross-dressing but was either afraid to say anything about such a complex subject or thought it was a phase that would go away. Obviously, the joke was on her. My wanting to be a woman never did go away; I just matured into it. Plus, back in the late 1950’s and early 1960's, there was very little good information about gender issues to deal with, so we were on our own as gender issues were called mental illnesses. Which even I knew at such a young age was not true. For all I knew at the time, I really liked experimenting with mom’s clothes and makeup and binge dressing was becoming routine.

As I said, once I began to mature into being a more accomplished cross-dresser (even before I considered myself transgender) I managed to dress more and more. I was even able to buy a beautiful long blond human hair wig that she hated and I loved. Finally, after I changed girlfriends, she went away and I kept the most important part of the relationship to me which of course was the wig. It brought me to a whole other level of cross-dressing away from Halloween wigs into the real deal. Back in the 1960’s when miniskirts were in, I could not wait until I could find a chance to slide on pantyhose and miniskirt and top it all off with my blond wig. Yes, I did binge any chance that I got!

Sadly, my binge dressing needed to come to a complete halt during my military years in the Army. Instead of worrying about how short I could wear my miniskirts, I had a more immediate and important problem of how to deal with weapons and drill sergeants in Army basic training. How I survived was that I put all my fond memories of cross-dressing in the back of my head and daydreamed about the future I knew I could have shaving my legs again and binge dressing as a woman.

After I served my time in the military, the only immediate release I had from all the tension I felt to be feminine at all was with all the many and varied Halloween parties I went to. During that time, I went from being a French woman with my blond hair, black outfit, tights and beret, all the way to professional woman one year when I was mistaken for a ciswoman just getting off work. The good news was I was learning a lot, and the bad news was Halloween only came about once a year. I needed desperately to find another way to binge with a purpose and express myself as a transgender woman. A term I was beginning to accept as my own.

Once I began to accept who I was, I needed to set out to prove it to myself and the world that I could live my truth. It was then that my binging took a whole different direction from where I was before. Thanks to the basic acceptance I gained from successful Halloween parties, I had the confidence to know I could look the part and blend in with society as another ciswoman. Little did I know then, the hardest part of my male to female femininization project was yet to come.

It took me finally getting out of the gay bars I regularly went to for some sort of validation I never received and into being accepted as a regular in many of the straight venues I went to and enjoyed as a man. My validation as a regular gave me the confidence to keep trying to improve myself as a transgender woman rounding out her life in the world. As I achieved goal after goal I set up on my trans bucket list, I really binged out every chance that I got which put me into a direct collision with my second wife who did not want to live with another woman and my male self who was dead against giving up his life all together.

By all out gender binging, I had set myself up for an internal war I was fortunate to survive. It took me all I could do to keep all my lives together as the years progressed. All I knew was I was able to carve out a dream existence as a transfeminine person. No one knew of my male past, and I loved experiencing every moment of my new life. Deep down, for once I felt I was fighting my self when I was binging as a trans woman and expressing my true self.

By turning back, the clock the best I could, I tried to take the best that I learned from my male life and apply it to building a solid base for my female life. I think it worked because I was able to decide which of my male baggage was important enough to bring along and I benefitted from being blessed with a long life, so I can see a number of important things come full circle (which is another blog post.)

The bottom line is I have always been an impulsive person which helped me all the times I just had to binge to satisfy my needs. Dealing with my gender issues was just an integral part of that.

 

 

 

 

 

 

No Participation Awards for a Trans Woman

Image from Brett Jordan 
on UnSplash.

As I traveled up my very long gender path with all its stop signs, I realized there were no awards for just participating coming my way. In fact, just the opposite was true.

Every time I was able to cross dress in front of the family mirror and not get caught, I experienced major gender euphoria but no awards because I knew I would just have to go back to my boring male life which I wanted no part of. Since my feminine self was deeply hidden from the world, there were no awards when I mastered a certain make up look or did not run my panty hose. On the other hand, I could expect some sort of gratitude when I achieved good results as a boy. I hated the total imbalance of the system I needed to live under with no available choices coming my way soon.

It wasn’t until much later in life did, I began to experience any participation awards at all. In the very beginning after trips to the big malls I was going to, even on the nights I was laughed at and scorned for my appearance, I felt at least I had tried and needed to go back to my cross-dressing drawing board to come up with ideas about what I was doing wrong. After setting aside my stubborn ideas of trying to dress sexy like a teenaged girl, and dressing age appropriate I was able to blend in with the ciswomen around me and not cause any undue attention to myself. I gave myself a bigger reward when I reached that major milestone in my life back then as a part-time cross-dresser.

Then, I became frustrated because it seemed the awards began to become harder and harder to come by as I started to overachieve as a transfeminine person seeing the world for the first time. Those were the days of trying to overcome a portion of my guilt for sneaking out of the house dressed as me by trying to do things which helped the household such as grocery shopping or better yet, trying to find my wife a garden gift at one of the nearby antique malls I went to. She was a huge gardener, and I thought an occasional gift would please her but probably pleased me more because it helped soothe my guilty conscience and gave me an imaginary award to put up on my mantle. I wish I could say I had a lot of awards, but they were very difficult to come by. Plus, my collection would be destroyed every time my wife caught me out of the house, and I became discouraged and decided to purge all my feminine belongings only to have to start all over again. Until I realized purging was fruitless and my desire to be a woman ran too deeply than just having the clothes, shoes and wigs that I had collected.

Overtime, with all the purges I attempted, I became better at keeping key items of my wardrobe I would need if (ha-ha) the urge to be a trans woman hit me again. I was not the sharpest tack in the box and still had not realized being trans was apart of me and would never just go away.

In the meantime, I continued to go out at night in the world and collect my participation awards as I learned what it really meant to be myself. To do so I needed to leave the gay bars behind that I was frequenting where they only thought I was a drag queen and try out the real world for a change where at the least I could be accepted as a woman from a different past. To do so, I needed to hitch up my big girl panties and do a deep, scary dive into the world I wanted so desperately to be in. I was growing increasingly tired of living a lie as a man and wanted out. In the beginning, I still took what I thought was the easy way out. By going to venues, I frequented often as a man and had wondered how it would be to live it as a transgender woman. It also helped that I was able to see how single women were treated in the straight places I was considering going. The last thing I wanted to do was to feel unwanted or afraid being a single woman in a venue full of couples.

After much thought and caution, I tossed my misgivings aside and considered what was the worst that could happen. My frail ego would be destroyed, and all my participation awards would be destroyed was my first thought. Then, I relied on all my new-found confidence as a transgender woman to succeed at my first big moves in straight venues in the world around me. To my amazement, I was treated well in my new world, and no one laughed at me or treated me with disrespect as I left my unwanted male privileges behind to learn what all the female privileges were all about.

I learned immediately one of the benefits was just being treated nicer. Even to the point where I was invited to staff girls’ nights out when the bartenders were concerned, I was lonely. Which I was. Better yet, one bartender set me up with her single lesbian mom whom I remain friends with to this day. Ten years later. There would have been no way that I could have made friends as easy as I did as a woman than I ever did as a man. A major reward for all the years of work I had put into succeeding on my gender path to my dream.

Another major reward I have received over the years comes from all your comments and feedback to my experiences. Originally, the idea was to write a blog (before I even knew what was one) to help others with similar gender differences so they could learn from them. Thanks to you, the idea has grown way past my expectations.

Thank you!

 

 

  

Being Hyper Focused as a Trans Girl

 

Image from Maxim Tolinisky 
on UnSplash.

As I followed my path into transgender womanhood, I found several times that I was too focused on my goal of presenting successfully as a woman when I went out and tried to join the world.

Essentially, what I mean is I was trying too hard to mimic the way ciswomen look and how they move about in the world. I had not yet had the time out in the world to develop the muscle memory I needed to be at my best with others. I so badly did not want to slip back into my old male ways and look like a linebacker in drag in high heels in the mall. In the meantime, I was spending every spare moment I had by myself to try to practice my best feminine walk.

The problem became when I was practicing too much and forgot where I was. Looking feminine in the least at work would not have been good for my macho career. I did the best I could with the time I had to work with just was not enough to create the habits I needed to progress the way I wanted to towards my transfeminine dream. Every time I went out, I would do something wrong and destroy the image of being female that I was trying to portray. If I had my makeup, clothes and hair to a point where I was satisfied, something would come along like catching one of my heels in a sidewalk crack to hurt me. I was very frustrated at the time until I finally began to relax and began to enjoy the new world I so badly wanted to be part of. As I did it though, I was totally surprised at how complex the entire scope of what I wanted to do as a potential successful trans woman would be. My life was like one of those huge “Bloomin Onions” you get at steakhouses. Every time you peel back a layer, you find another layer to surprise you.

As it turned out, at the time I was peeling back more gender layers much quicker than I had ever imagined. I was dodging all the stop signs that I thought I would have and was able to look around my world and enjoy what I saw. Most importantly, I was becoming the me I always wanted or destined to be. Again, I was being blindsided in that I would have to go through yet another transition as my life was coming full circle. I was not becoming someone different at all. I was just becoming me.

The one remaining aspect of my transgender being I did have to remain hyper focused on was when I began in depth communication with other women. I was always paranoid that I would give away too much of my old male past when I was talking with another woman. I worked so hard to be in the world as I was, I did not want to out myself as an intruder. Quickly, I made strides to learn the different way ciswomen communicate that men just don’t understand such as non-verbal cues about danger and happiness. All the way to the power of passive aggression that women use so effectively. To aid in my efforts, I even took feminine vocal lessons to learn key terminology I would need to complete my communication efforts in the world.

As I followed this new direction on my gender path, I did slide back into being hyper focused in my quest to be me. I was intently watching all my new ciswomen friends to see how they lived their lives and how I could fit in. In essence, the new me needed a new place to live and they gave it to me without ever realizing what they were doing because they took their lives behind the feminine gender curtain for granted and I never could. And still don’t to this day since I spent so long trying my best in the dark to get there. I guess I was paying my dues as I learned what my second wife meant when she called me a terrible woman. Back then I was, but I did not want to make that mistake again. So, I became hyper focused on a new goal…earning a spot behind the gender curtain.

My confusion set in because I learned early in life what it took to survive behind the male gender curtain, but I had no clue at all what it would take to survive as a trans woman. Because I knew I would never be able to have such life altering experiences such as carrying and birthing a child such as ciswomen have but on the other hand, I still had a very unique way to my womanhood which still counted. I just had to wait and earn my way back to being me. Furthermore, I did not want to completely throw away everything that I learned for fifty years living in a man’s world. I just wanted to take the building blocks I learned and use them so I would be able to be a quality transfeminine “me” person and never be told again I made a terrible woman. If I was “making” anything from scratch, I wanted it to be presentable to the world.

Once I was able to stop being hyper focused on my early experiences with makeup, hair and appearance, reality in the world set in which meant I would have a chance to live my dream of throwing out or giving away all my male clothes and starting all over again. I hope being a hyper blend of the two main gender binaries helped me along once I finally sensed the true path I wanted to be on.

The ups and downs of life on the journey I took was never easy, but worth it when I made it to the surprise location I was heading for that I never realized. All along, I was just focused on being me.

 

Are We Having Fun Yet?

 

Image from Katie Treadway
on UnSplash.

Having fun as a transgender woman or transgender man can be difficult to define. First, let’s define fun as something that provides mirth and amusement. Which comes from “Dictionary.com.”

In my case, I cannot remember finding much “mirth and amusement” when I was cross dressing as much as I could to present as an attractive girl. All I can remember was that I was experiencing deep satisfaction when I thought I had succeeded. As I began to search for a better term, I went back to the “Dictionary.Com” to look up the definition of happy. Because happy is how I felt when I thought I had succeeded into transforming myself into a pretty girl. I was right when the definition of happy was “delighted, pleased or glad” when something was accomplished. It fit me totally because it worked in all aspects of what I was trying to do. Actually, it was all three of the delighted, pleased or glad definitions which fit me exactly.

The problem I was having was getting to the point where I could be happy about trying to cross the gender border. I severely struggled to find the fine line where I could disguise my broad shoulders and narrow hips of my testosterone poisoned body. I certainly was not happy or having any fun when I was brutally laughed at by the way I was trying to present myself as a woman in the world. As I always point out, back then teenaged girls were the biggest test I faced when I went to the malls and they seemed to be attracted to me like magnets, for all the wrong reasons. It took me a while to realize I was trying to dress like teenagers, which brought me completely undo attention. There was no way I could be happy.

What I also did not understand was that fun or being happy was a fleeting thing for me. Sort of what had you have done for me recently, type of thinking which I was very used to from how I was raised. For the most part, I was never allowed to be happy, so I did not miss it at all. I also say for the most part because slowly I began to discover I could feel happy when I was cross-dressing as a man into my true feminine self. When I was able to find the proper clothes, shoes and wigs which helped me with my appearance with my makeup, I could relax and enjoy a new world I had only dreamed of.  Fun became to me when I could escape the male world, I was forced to spend so much time in and explore all the new facets of being a confident transfeminine person. It made me happy to discover who I really was destined to be in life.

As I headed past the fun and happy part of discovering myself as a transgender woman, I needed to mention the satisfaction I felt when I had reached the point where my diet had kicked in and I could buy more stylish clothes in my own size for the first time ever in my life. I was ecstatic in my pre-hormonal HRT days when a cross-dresser friend of mine purged his feminine belongings and gifted me a set of silicone breast forms that I needed to run out and size just the right bra for.

Those were the early days of my explorations in Columbus, Ohio when I could attend very diverse by invitation only parties where I could see everyone from lesbians to transgender women considering gender realignment surgeries so I could have a idea of how I might want to live my life in the future. Almost every party I went to was to be a fun learning experience, and I could not wait for the next one. At the same time, I was thinking if I was having this much fun, how could it be wrong to have it.

The only negative I experienced was the night I was cornered in a narrow hallway by a huge admirer of crossdressers and almost learned the hard way about what ciswomen learn at an early age. To not put yourself in compromising positions with men which could possibly overpower you and get yourself into deep trouble. I was lucky that my wife came along to bail me out of the situation I unknowingly put myself into.  It was no fun hearing her, I told you so’s all the way home. Mainly because she did not approve of what I was wearing.

As my life progressed towards the ultimate goal of leading a fulltime life as a transgender woman, unfortunately, my wife stood right in my way of progressing.  Which meant I needed to cheat on her with another woman which was me. Every time I slipped out of the house in my heels, jeans or boots, I normally had a good time as I was finally having fun as a trans woman and did not want to ever give it up,  I had gone too far to ever look back to an old male life I never had a choice on living to start with. Like it or not, my life had put me on a collision course of having to decide what I was going to do about my marriage. The course was disrupted when my wife unexpectedly passed away from a massive heart attack leaving me tragically alone after twenty-five years of marriage.

Most certainly, those days of my life were no fun, and not filled with happiness. On the other hand, they were filled with uncertainty and loneliness until I could find my way home again. Thanks in no small part to my inner feminine self who took over my life and others such as my daughter and future wife Liz. Who helped to pull me from my major pity party. When that happened, life became fun again as I was able to lead a life in the feminine world I always wanted to be part of.

 

 

                               

 

 

My Last Date as a Man

 

JJ Hart in the long black wig
I wore to the concert. 

My last date as a man was very eventful as destiny was sending me a powerful message.

It all began a couple of years after my second wife passed away and I decided to again seek out feminine companionship from a ciswoman. Then I made a mistake and became enamored with the mom of one of my servers at the restaurant I owned. Mom was about my age and extremely attractive and I gathered up the courage to ask her out when I learned she was single. From there we went on several dates including one in her native Cincinnati. I was quite naïve and thought things were going fairly well until my daughter got me two tickets to a “Joe Cocker” concert at an outside summer festival near to where she lived in Dayton, Ohio.

I guess the idea of perhaps meeting my daughter scared her off, because after initially saying yes, a week before the concert she abruptly said no and I wasn’t to call her anymore. By this time in my life, I don’t think anything could surprise or hurt me more than what I was already going through, so I picked up the pieces of this brief ill-fated relationship and prepared myself to move on. But I had one problem, what was I going to do with the other ticket I had for the concert. Then my mind came up with a plan, why not invite my feminine self? It would be yet another test to see how successful my transition was coming along as well as soothing the ego wounds from being turned down by what turned out to be the last date I would ever have as a man with a ciswoman in my life.

At that point, I was very much still in the closet to my daughter, so I planned to pick up the tickets as my male self then go home later and get ready. Getting ready proved to be an adventure as I knew I could put together an upscale/casual outfit for the evening. I ended up choosing a black outfit with a three-quarter sleeve mesh top and wide legged silky black pants with black sandals. Topping it all off, I chose my long black straight-haired wig and sunglasses on my head as an accessory. After carefully applying my makeup, I was ready to take on the world as a transgender woman out to her first concert. I felt good and confident for a change as I left the house for the half hour drive to the concert venue.

Once I arrived, I gathered myself, checked my makeup and took off walking to the concert which was filling up with people fast. Since it was still light outside, I could wear my sunglasses to check out anyone who was staring at me without them knowing. I was relieved when no one noticed the tall, long-haired woman in black making her way through the crowded sidewalk to her seat. I even had enough time to walk up to the concession stand and order me a refreshing drink before the late “Joe Cocker” started his show. By this time in his career, he played his hits and I was happy.

I ended up immensely enjoying the concert. Even more so since I was spending unique public time with my transfeminine self. I walked away from the experience with a new-found confidence in myself to live my life the way I had always dreamed of. In a world where ciswomen ruled. And maybe most importantly, I don’t think I embarrassed myself by the way I looked.

Maybe I was a little too over dramatic when I mentioned destiny setting in that night, but it did because never again did I set out to date a ciswoman as my male self and go through all the dating contortions I hated so much. I don’t know why but I always had felt so much more at ease when I was dealing with women as a trans woman and I never looked back.

My last date as a man was uneventful because it never happened it seemed for a reason. In the future I was able to have much better times going to places such as roller derbies with my lesbian friends where I could relax and have fun. Something I rarely did when I was trying to date as a man.

 

 

Stopping when You are Ahead

 

JJ Hart. Girls Night Out.
I am top left. 

Somehow, I never learned to stop when I was ahead when I was growing up. Or, as my parents always said, I tried when I was given an inch, I always tried to take a mile.

That whole idea really manifested itself when I began to explore my gender desires and start to cross-dress in my mom’s clothes. As I perceived myself to be successful with one new look, I always wanted more very soon. I could not stop when I was ahead and kept on pushing the boundaries of danger when I cross-dressed at home in the bathroom. Even if my brother was home too. I was risking what I had of the young male life I thought I needed to protect.

Somehow, my guardian angel was looking over me as I never got caught as a kid with my cross-dressing activities and I simply wanted more than I could get most of the time such as a nice, fashionable wig. Rather than the Halloween store wigs I was stuck with. Due primarily to financial constraints. During this time of my life, I was stuck with just being able to dream of what my life could be like when I grew into a more complete transfeminine person. It turned out to be a long (decades) away from coming true. Take wigs for example. When I finally arrived at the point where I financially could afford it, I went overboard on haunting the local wig stores around me looking for just the right wig which I thought would be the perfect addition to my hair collection to allow me to present better in the world. As I did it, mostly all that I accomplished was acquiring quite the collection of potential drag clown wigs which I did not have the patience and/or knowledge to take care of.

At that point, I could not stop when I was ahead or behind my quest to be at least an attractive woman. Every time I experienced the least little bit of gender euphoria when I went out in public, it fired me up and encouraged me to do more. Unfortunately, that meant taking extra chances with my actions and ultimately my safety. I needed to learn the hard way what ciswomen were raised to know about not putting yourself into potentially dangerous situations. I barely lucked it out when I escaped situations with no harm to me, so I essentially did not have to stop when I was ahead as a trans woman. I just had to be wiser when my male privileges were stripped away such as the personal security privilege men inherently have.

As I emerged as a wiser novice transgender woman, the reality of what I was attempting set in and I could not stop. Even if I was ahead. I began to set up a stairstep approach to my male to female feminization process which would I hoped, give me a more in-depth look at a woman’s life behind the gender curtain. Which I had spent countless hours thinking about. I started to consider all the things I wanted to discover as a woman that I had dreamed of as a man which led me to set up my own transgender mental bucket list of things to do. Basically, I set up activities at levels of difficulty. So, when I accomplished one I did not have to stop and move to another. Using the women’s room was a prime example of sliding behind the gender curtain and using a women’s only space. I knew a little of what to expect from my days as a restaurant manager when I needed to monitor how the women’s room was kept for problems I could encounter. Not starting from scratch helped me to survive in my new world with cis women.

Fortunately, I spent much of my time in the world successfully as I learned the basics of how ciswomen live. By doing so, I simply could not quit and kept on trying new things. My bucket was quickly being worn out by the challenges I was facing. Mainly by meeting the number of women who showed interest in me. I have always thought they were just curious about what I was doing in their world and was I living my life the best I could in the girls’ club. In my case, I was different and hopefully presented the best of the two main binary gender worlds as I socialized with many different women who seemingly were happy to see me.

By this time in my life, I simply could not stop what I had started as far as chasing my femininization process. It involved doing a deep dive into how women communicate and compete with each other, among other important things. Probably, communication was the most difficult aspect of my transition to learn. For the first time in my life as a transwoman, I needed to listen closely and completely to what was being said to me for hidden meanings and nonverbal cues. Then, as far as competition as a woman was concerned, I needed to learn that women compete just as hard as men. Just on a whole different spectrum of passive aggressive actions and reactions. Believe me, I learned the hard way a number of times when I made the wrong move and needed to watch my back from a smiling face who was out to get me.

Once I succeeded in learning all of my feminine lessons, my confidence was at a all time high. Especially with the small group of lesbian friends I had build around me by sheer luck. They ended up protecting me during my fragile times I was learning the final ropes of what it would take to round myself out as a transgender woman. By this time, my inner self could take over after being buried all those years and end up running my life’s goal that she always had a hand in. After waiting all those decades to live, she no longer had to stop while she was ahead. She was home and I was a whole person.

 

 

 

Playing on the Girl's Team

 

Image from Fa Barbosa
on UnSplash.

I am fond of calling my initiation into the world of ciswomen as being allowed to play in the girls’ sandbox. But recently, I have seen it described as playing on the girls’ team. When it comes right down to it, it doesn’t matter what you call it when you have essentially given up life as you know it to transition into the feminine world.

When I was allowed to play on the girls’ team, of course there were many new things I needed to learn because I was seeking admittance to a new and complex, layered feminine existence. For the longest time as I was learning what life really was like for ciswomen, I took the easy way out by thinking all I needed to do was look the part. This is when my second wife began to mock me by calling me the “Pretty, Pretty Princess.” She was right as my presentation was advancing quickly forward and I had ego trips when women at transgender socials I went to on Long Island, New York mistook me for a real woman and wanted to see a male identification before they would let me in.

Even though I was extremely flattered when they asked for my ID, deep down I knew my wife was right and all I was trying to be was a princess. That was when I tried to begin studying the lives of women around me to discover the deeper meaning of being allowed to play on the girls’ team. Which I knew my wife would never help me with. She was busy with bigger issues such as the possibility of losing her husband to another woman which was me.

Initially, the shock of playing on a different gender team came from losing all of my male privilege such as using my size to bluster my way through life. All of a sudden, my size which I took for granted became a problem for me to disguise with the best fashion choices I could. All I knew for certain was I was told I had good legs at the Halloween parties I attended as a woman, so I tried to build my style from there. All the way to putting together my own tennis outfit even though I had never played a game in my life. Eventually, I needed to back off from showing too much leg and getting kicked off the girls’ team for not blending in and attracting too much attention to myself.

It took a while, but finally I began to realize what feminine privilege was all about and it was so much more than just having men open doors for me. Privildge to me meant I could appreciate the world around me so much more deeply. I had many more avenues to explore in the world once I escaped the restrictive bonds of living in my old unwanted male world. Other women freely interacted with me once I was firmly accepted on the girls’ team and once I learned the rules of engagement and communication, I was able to have so much more enjoyment in my life. Most importantly, I knew I never wanted to go back no matter how many stop signs I faced on my gender path.

Sadly, my second wife passed away before she could see the maturation of her princess into a fully-fledged transfeminine person. Looking back, I don’t think we could have ever stayed married but hopefully we could have remained friends while I continued to fill out my gender workbook. I finally learned I did not have to rely on her assistance to gain admission to the girls’ team because she had given all she could to help me. As with any other female, I needed to find my own way to womanhood. And even though I was not born as a psychical female, I surely thought like one and fought to be one my entire life.

As a novice on the girls’ team, I needed to earn my way also which included many bumps and bruises along the way when I learned I was much more than a cross-dresser who liked to wear women’s clothes, the mental process I went through was much more complex and tougher. To quote an old popular “Kenny Rodgers” song, I had to know when to hold them, know when to fold them and know when to run when I was dealing exclusively with other women.

Fortunately, my newfound acceptance on the girls’ team meant I needed to do very little running. No one came up to me and tried to pull my wig off in public, and for the most part I had to just deal with silence, stares and glares when I encountered a woman who for some reason wanted to hate me. There was one in particular who was also invited to the girls’ nights outs I was invited to who had a problem with me being there. I was able to ignore her for the most part or try to kill her with kindness. Finally, it occurred to me that her problem may not have anything to do with me, it may have been with the world. Maybe she resented the fact that I was happy, and she was miserable.

The more I was allowed to play on the girls’ team, the more I learned from them on the nuances of the new life I so badly wanted to live. Along the way, I never imagined learning so much in such a short amount of time. I also never thought feminine privilege could mean that much to me after I left all my male privilege behind. Especially when the effects of HRT softened my world and improved all my senses,

Whatever you want to call it, playing on the girls’ team or playing in the girls’ sandbox never mattered to me. The most important part was that I made it and rarely got any sand thrown in my face as the princess grew up.