Monday, August 11, 2025

Buckle Up!

 

Alpha Gatekeeper Hope
Who Let Me In!

If you are a transgender woman or trans man and you have been transitioning along your gender path for any length of time, you know there are plenty of highs and lows to prepare for.

I know on my gender journey; I have had to buckle up for many rough roads ahead. I have many examples I write about often such as being told to leave one venue I started to go to when I decided to leave the gay bars behind and go to mainstream straight venues. I went home in tears like when I was laughed out of malls by groups of teenaged girls when I first attempted to go out in public. For a long time, I never thought I had a chance of living my transgender dreams at all.

Deep down, something told me to fasten my seat belt and keep trying to succeed. You see, the problem was all along in my life, if something went wrong, I ran to my skirts and put on makeup to make it go away. In these cases, I had nowhere to run, so I had to get it right. I was in a corner, and I couldn't get out without a lot of work. It turned out to me, the whole process was a labor of love, and I felt good going forward on my gender path. The problem was I was still quite naïve about what I was facing and thought success could be found if I just was able to present properly as a woman. To try the new world out I was in, I went to all sorts of different situations. Examples were when I went to a downtown festival and an outdoor concert just to see if I could. Following painstakingly applying my makeup and choosing just the right clothes, I managed to be successful at both, and my confidence soared.

When I did, my frail confidence was shattered again when I learned the world was curious about me as a transfeminine person. It meant I would have to really buckle up and do more than trying just to look like a woman, I needed to communicate like a woman. All of that turned out to be harder than it sounds (no pun intended). I found out quickly that women operate on a different wavelength than men. Men use a more simplified straight forward approach to communicating with each other and other women. On the other hand, I discovered I better refine my listening skills, plus be aware women communicate with each other on non-verbal wavelengths. Also, eye contact with other women became very important too, if I was ever going to be allowed to play in the girl’s sandbox by the alpha female gatekeepers.

As with anything else, I needed to allow practice to become perfect if I was ever going to succeed at reaching my goal of living as a transgender woman. To do it, I needed to forget my unreachable dream of being able to present so well as a woman that anyone would ever think I was cisgender. To begin with, testosterone poisoning had taken all of that idea away from me. I needed to re-buckle up my expectations and know the best I could do was follow my path as a woman from a different background. To succeed, I needed invitations from cis-gender women to their girls’ nights out so I could observe and learn how other women acted when men were not around. Naturally, I needed to put what was left of my male ego behind me when I had to buckle up and attend several of these meetups. My primary example came one night when I was invited along with a group of servers where I went to, to another upscale venue to party. They were all young and attractive and immediately were surrounded by attentive males, leaving me by myself and my drink. I learned a powerful lesson that night why certain attractive women tend to hang out together.

I was fortunate as I traveled my gender journey, I had key alpha females to help me with my seatbelt. As an example, I have added the picture of “Hope” who ironically gave me hope for my future dreams. She was the first bartender I ever met who went out of her way to be kind to me, all the way to introducing me to her lesbian mother who I stay in touch with to this day. Hope led the way for me to be accepted by others and thrive in the girls’ sandbox, and I will never forget her for it.

My main message is, no matter how many bumps and bruises you may suffer along your own gender journey, just try to securely fasten your seatbelt and make the trip as interesting as possible. Just remember, not many are able to make the same journey and achieve their dreams of living as a transgender woman.

 

 

 

Sunday, August 10, 2025

Low Risk...High Reward?

 

Image from Jayson 
Hinrichsen on UnSplash.

There are many things we do in the gender universe which represent a low risk, high reward effort.

For example, under the cross-dresser umbrella, we have the far-ranging participants who go from wearing panties under their male clothes, all the way to those who fully dress as transfeminine women in their spare time. At the least, there is more risk to the cross dresser who is fully dressing in feminine fashion and makeup than the person who simply needs to pull his pants up to cover his panties. At some point too, one must consider if wearing women’s clothes is simply a fetish or is there more to it. Which carries even further into the world of sissies and such which involves men who fantasize about forced femininization.

In my case, even though I deeply felt the pleasure of hose on my shaved legs, or other beginning thrills such as looking at myself in the mirror, deep down I knew there was so much more to what I was doing about my developing gender issues. I knew too, if I was ever caught with my clothes and makeup on, there would be no rewards, just risks, so I needed to be very careful. All the way to the point of never wearing panties under my male pants at school and on rare occasions dreaming about a woman forcing me to cross dress at all. Ironically, I talked a woman into dressing me head to toe as a woman only one time and I ended up thinking I could have done it better myself. The risk of telling her did not equal any reward at all.

The risks and rewards proportionally grew greater together as I grew older and my male life began to grow. Many times, without my feminine one who was still stuck in her mirror. It was in the Army of all places, when I first came out to a small group of friends that I was a transvestite and much more than the fully cross-dressed woman they were able to see at a Halloween party. Naturally, it was a huge risk to take because the Army could have taken measures to discharge me. The reward did come when I was able to finally feel the relief of telling someone else my deepest secret and no one cared.

The further reward of coming out of gender shell was the fact my first wife was in the group of friends I came out to. Our marriage then led to the greatest reward of my life…the birth of my daughter who supports me to this day.

As my male world kept expanding and threatened to take over my transfeminine experience, I was going through a wonderful period of great discoveries in my life. Those were the days when I first discovered the transgender term and what it meant to me. For the first time in my life, I found a community which I belonged in. I was too much woman for the average low risk cross dresser and too little for the risk it all world of the transsexuals who were headed for gender realignment surgery.

I was so comfortable in my new place in the world, I was prepared to take bigger and bigger risks. Much to the chagrin of my second wife who had no problem with my cross dressing but was totally against any thoughts of starting gender affirming hormones and living increasingly as a woman. Every time I went out to explore the new feminine world I was creating, I was risking my twenty-five-year marriage. Because I chose to lie to myself for many years of denying who I really was, I ended up making us both miserable.

My excuse was I knew I would be losing a great marriage, a substantial job and many hard-earned male privileges if I threw all my cards into the middle of the table and came out into the world as the person I was always meant to be. Finally, the choice ceased to be mine as I embraced my new feminine self. My wife had passed away, I reached the point where I could retire from my job, and I was eager to check out the world of female privilege. It was all a huge risk, but I had to take it as I was nearing the age of sixty and I figured I was near a now or never moment in my life.

I had never been a gambler of any sort, but I wished I had the courage to make the move I made earlier. One thing is for certain; you can never rewind your life to make up for past mistakes. You just have to do the best that you can of your past to plan ahead for the future risks you will have to take.

 

 

Saturday, August 9, 2025

No Easy Way Out.

 

Image from Peter Fogden
on UnSplash.

When I had grown used to escaping my male problems by dressing in front of the mirror in my small stash of girl’s clothes and makeup the best I could, then I forgot my problems. It was an effective way to find a way out.

Before I knew it, I was digging myself a hole I would have a difficult time getting out of. As always, my main problems came from my refusal to accept my gender issues. I would cycle through the same old issues such as cross dressing until I relieved all the pressure I was under as my male self. Then knowing the relief would only last a couple of days.

Occasionally, I thought I would find the way out of my gender shell by trying the infamous “purge” which would finally do away with my feminine self altogether. Of course, we all know purging was no escape either as in a very short time, my urge to cross dress would flood back in again. All of this resulted in depression I struggled to control.  Years flew by before I was diagnosed as being bi-polar by a gender therapist I was going to. The diagnosis helped me to understand why I would sometimes want to do nothing but stay in bed. Fortunately, I was able to find a medication to help me that I was able to tolerate, and to this day, my depression is under control. Plus, having my bi-polar under control allowed me to separate it from my gender issues.

It became extremely important when I was matched up with a therapist from the Veteran’s Administration who controlled my gender affirming hormones. One thing I did not need was a therapist who connected my dots wrong and left me no escape. What I mean is, if I was matched with a therapist who thought my depression and gender issues were connected in any way. As with other things I excessively worried about, the therapist I ended up being matched up with never connected my dots wrong, and my HRT and depression medications were always kept separate.

Escape finally came slowly when I began to take control of my own life. I went down a huge rabbit hole I had been ignoring. As I left my old gender closet and explored the rabbit hole as a whole new person, I discovered the world I had only dreamed of as I began to live as a transgender woman. I also found many new layers of a feminine life I knew nothing about. I went from creating a fictional trans woman to a real person as I explored the world. The real person I became had to be able to communicate with the world at large. As with any other worlds I ever discovered (such as the military) being a transgender woman came with a whole new set of rules I could not escape.  

As my confidence increased, so did my success in building a new life. I so badly did not want to escape at any costs, I risked all my male life such as family, friends, and employment to live as a transfeminine person. I was putting on the line such as the benefits of hard-earned male privileges, a long-term marriage and a good job. All to follow my feminine dreams. It turned out, I learned many lessons when I was attempting to escape the rabbit hole I was making for myself.

Some would say it took a lot of courage to do what I did. While others would think I was nothing but a fool. I would say neither is the case because in order to live in this world at all, I knew I would have to make changes to escape. By the time I needed to make the final transition decision, I was nearly sixty and it had been weighing heavily on my shoulders for years. By then, I took all my so called “practice” time and became a transgender woman on a mission.

I escaped all excuses and rabbit holes I explored on my way to living my dream. Becoming my true self in a woman’s world was incredibly difficult to do. Just when I thought I was conquering the road I was on was being successful, I learned I was only just beginning and there were many obstacles to come. I was lucky enough to be able to negotiate everything by having wives to women friends to help me on the way.

If I had given up the fight and given in to the true desires I was having, I would have never had to think I had no way out.

 

Friday, August 8, 2025

Hormones in my Life

 

Image from Mitch
on UnSplash.


This morning, as I changed out my Estradiol hormonal patches, I briefly paused to consider the magical changes HRT has meant for me.

My thoughts were formed yesterday when I wrote a short chapter in my book I was writing on my life that my daughter bought for me. As I remember, the question of the week for me was how I responded to changes to my body over my life. I started by writing about how bad I felt when my body began to form angles when I went through male puberty. It was long ago, but I still remember my disappointment. This was way before the time of puberty blockers for young transgender boys and girls. Not that my parents would have approved of blockers for me anyhow.

I followed up my ideas on male puberty with what had happened to me since I was fortunate enough to be approved for gender affirming hormones and I could experience a second puberty in my life, this time, one I wanted. Even though I was attempting to overcome all the damage testosterone did to my body, I could not fix most of it. I was stuck with broad shoulders and a big male torso which served me well to keep bullies away but did little to help me to present well as a transgender woman.

On the positive side, the new HRT meds were able to soften the harsh angles of my face and soften my skin, so I could use less makeup. I also found I had no male pattern baldness, so my hair grew so well one of the first things my daughter did was treat me to a hair styling and color at her upscale women’s beauty salon. Another case of being totally out of my old male environment and loving it. After my fear went away. At that point, I was loving my new life.

My new life as a transfeminine woman took on a new meaning as I adjusted to my new body. Gone were the old days of blustering my way through life with my male body. In were the days of being more in tune what was my body telling me from newly sensitive breasts to a developing transgender woman’s’ intuition, I was really changing. By intuition, I mean I needed to develop a sense of anyone who was going to potentially threaten me with any harm. Much of the new development was not much of a problem because I was going through so many other internal changes anyhow. The easiest way to explain it is, my world went from the harsh realities of being male, all the way to the softening universe of being a woman.

Also gone were the days of me attempting to macho my way through any situation. From being able to admit when I was cold, all the way to planning ahead to any potentially dangerous situations, it all presented me with a new world to consider. All because of two little Estradiol patches I applied twice a week. It was magic to me how well and how fast they worked. It was as if my body was waiting for the HRT meds my entire life.

It is not often that I have the opportunity to slow down my everyday life and consider the benefits of being approved for gender affirming hormones. I needed to go to a physician back in those days which were relatively difficult to find. On one hand I had seen the health problems other transgender women had gone through when they went the route of unsupervised hormones. Since I was near the age of sixty at the time, I did not want to risk any health issues and fortunately, there weren’t any. Even though I do not remember the exact year I started HRT, I remember I took my first dosage which were pills with my future wife Liz on New Year's Eve. From there, I progressed to higher dosages and eventually to the patches I am on today.

Which brings me full circle to the meaning of this post. With or without the hormonal medication I am on, I would still identify as transgender. HRT just helped my external presentation in the public’s eye. And, if you are considering hormones, you don’t need them to be you either. If you do, make sure you seek out a doctor to help you to know all is well before you make the jump.

For me, the HRT process was the final point of knowing I was doing the right thing by jumping off the gender cliff I was on. It sure made the landing softer.  

Thursday, August 7, 2025

Jocks and Dresses

 

Image from Norbert Toth
on UnSplash. 


As a youth growing up, I found myself embracing the world of sports to cover up any lingering feelings of wanting to be a girl. Plus, being a jock of any kind helped keep the bullies away when I needed it the most. Why would they think a defensive end on the football team would ever want to be feminine in any way?

Little did they know, the time I spent longingly looking over to watch the cheerleaders practice was much more than admiring their short skirts and tight tops. My desire was in no way sexual; I did not desire any of the cheerleaders that way, I just wanted to be them. Happily, my cover worked and to the outside world I appeared to be a “normal” boy with normal hobbies such as sports and cars.  

It was my rendition of having my own gay beard as described here on “Wikipedia”: “Often, the term was used in the early to mid-20th century, used by homosexual individuals to conceal one's sexual orientation through the disguise of a heterosexual relationship.” I was not gay but needed sports to conceal the fact I was a cross dresser. My “beard” worked and got me through school very much unscathed. My gender closet was secured.

I was able to play football until I was hurt twice in my junior year and there was no place on the team for an injured slow defensive end and no matter how much dreaming I did, I could never make it as a cheerleader either.

Along the way, my love of sports became ingrained in me as much as the desire to be a transgender woman. If I can describe the love of sports I had, it was like a big set of luggage I was carrying from one gender to another when I needed to figure out what I could take with me.

It was about that time in my life when I was leaving my gender closet and looking around, that I began to see other women who shared my passion for sports. Just maybe, I could drop my beard and bring along what could be one of the most important pieces of baggage I had in life. If I was careful, and set myself up of success, it could quite conceivably be me as the woman at the bar watching her favorite team on one of the big screens. While I would not be a jock in a dress, I could be one in a football jersey.

Even better was when I was able to befriend a couple other cisgender women who were sports fanatics like me. We would get together often to watch games and harass each other when our team lost. It all led me to one of my proudest moments when I was invited to a NFL Monday Night football game in Cincinnati. I was still quite new to the world as a transfeminine person, so I was very scared, but I accepted her invitation to go. I had made the big time in my quest to have brought my passion for sports with me into my transgender world. Except for my team losing, I ended up having a great time and the whole experience really built my confidence in my new life.

While I never became exactly a jock in a dress, I did become one in makeup, leggings and boots. All along, I had my doubts about where my journey would take me and how I could get there. But I never missed most of the male baggage I needed to leave behind as I embraced the transgender future I was looking at. Maybe I was fortunate in that the world around me was catching up to an expanded role for women in the world as I was entering it. Whatever the case, it made my transition so much easier.

Also, I did not do it by myself, I had women friends to show me the way. They just happened to share many of the same interests I did. I mention them a lot, but I would feel bad if I didn’t give credit where credit is due.

Plus, from the comments I receive, I know I am not alone in utilizing sports to use as a “beard” in your life to cover up your gender issues. I remember one comment from a reader saying she used football shoulder pads to cover up the gynecomastia breast growth they went through early in life. Proving for many of us experiencing gender issues, hiding them can take many paths.

 

Wednesday, August 6, 2025

Female Privilege?

 


Is there such a thing as feminine privilege? Even though it is much different than male privilege, I think there is.

At first, the only privilege I could see in response to putting in all the work I was doing to present myself as an authentic woman was men would open doors for me. Ironically, opening doors for me was just a prelude to taking away my intelligence if they took the time to talk to me at all. Sort of like the tow truck driver one night who needed to explain the basics to me of how his wrecker worked before I gave in and just played the part of a dumb blond which matched the color of my wig, I was wearing that night when my car broke down.

What I was going through was losing my male privileges. The main one I always warn novice cross dressers or transgender women about is the male personal security privilege. Beware of going about your business as you had as a man when you jump the gender border because it could get you hurt. There is a reason women don’t go out alone into dark unsafe areas and you need to learn it too. You can get hurt, or worse if you have no one to protect you as a transfeminine person.

It took me awhile to realize there were many feminine privileges except for clothes and makeup. Like so many other things I was experiencing, I discovered the whole process was layered into the world of women as a whole. Much feminine privilege I found came from the separate world women create away from men. For example, to be allowed to play in the girl’s sandbox by cisgender women became much easier when and if I was accepted by an alpha female who acted as a gatekeeper. Much like when I was accepted in a venue I chose by a lead server or bartender. It was an easy way to earn the right to use the women’s room. All I needed to do was mind my own business and tip well and the alpha would do the rest.

At no point did I ever take the privileges or freedoms I had earned for granted. Because when I did, I would risk sliding back into the old male world I had come to dislike so much. There were many times when I sat alone and weighed the benefits of my new life to see if all the gender turmoil was worth it. On one hand, I was learning what my second wife told me I would have to learn about being a transgender woman, and on the other, I was scared to keep going towards a very steep gender cliff.

I suppose the biggest move I made towards learning what female privilege was all about was when I started gender affirming hormones or HRT.  As my body took to the new hormones as something it should have always had, as much as I appreciated the external changes, I appreciated the internal changes even more. My world rapidly seemed to soften as my emotional level increased for the first time in my life. I understood for the first time what women had gone through all those years in their lives. It was a privilege to try to erase as much as I could the effects of testosterone poisoning, which I had gone through so many years ago. As well as having the opportunity to go through my own version of female puberty while I still could.

The end result of my gender exploration was that each of the binary genders has their own privileges. It just is as if a man’s benefits are more pronounced, which is like a man’s life in general. As the man, I was for all those years, I was used to blustering and forcing my way through many situations I found myself in. Plus, I had very few real friends as a man which I could rely on to help when and if I found myself in a bind. Of course, women turned out to be different as I could rely on my cisgender women friends to help me in times of need. Which turned out to be mainly emotional, more than anything else.

After seeing both sides of the gender border, and having the chance to cross it, I made the right choice for me when I chose to seek out the real meaning of feminine privilege. Women certainly do not have it any easier, but I would take what I learned and feel secure in my choice to live in society as a transgender woman.

Tuesday, August 5, 2025

Is Purging Just a part of a Trans Journey we Need to Go Through?

 

Image from Shayan Rostami
on UnSplash. 

I received several wonderful comments to my “Purging” post yesterday including people such as Jeanie who has had gender issues for years such as me.

Here is the comment and we will go from there: “I just purged last Thursday. I wanted to see if there was a strong enough "desire to reacquire". I'd go months with the stash behind insulation in the basement under a bay window without dressing. It might be I was too chickenshit”.

Thanks for the comment! And it got me to thinking about all the ways we cross dressers or novice transgender women went to hide our small collection of feminine wardrobe and makeup from our family. As a kid, I even went as far as hiding my stash in plastic garbage bags in a hollowed-out tree in a neighboring woods. Where I hoped no one would ever discover it. In addition, I had two other small hiding places in the house I could go to if I was suddenly free to cross-dress in front of the mirror. The entire process added to hiding my gender issues in plain sight. Almost, as all along, I was desperately trying to escape being caught and being sent on an unpleasant trip to a psychiatrist who would have most assuredly pronounced me mentally ill. Which was the norm for mental health professionals back in those days.

Since I never completely purged my feminine stash ever, maybe I was too chickenshit to do it (as Jeanie said). Or, as I struggled throughout my life with gender issues, my own “desire to reacquire” would return to rule my life. As it turned out, I was never strong enough to purge totally. Which looking back should have given me a clue to who I really was, a woman cross dressing as a man. Deep down, I knew, every feminine item I had worked so hard to acquire could not so easily be thrown in the trash. It would ultimately come down to me wondering how much different I would look in the mirror if I had not thrown out my previous stash.

At first, it all got worse before it got better when I entered my strong going out in the world as a novice transgender woman with my second wife. Fortunately, when I was restoring the old house, we lived in, I was able to build in a closet we rarely used. So, I found a place to hide the many thrifts store finds I had made and purchased. Also, by this time I was in a place where I did not care what my gender foes thought. I was building my future public persona, so I needed to look my best. Essentially, I entered the “don’t ask, don’t tell” phase of our relationship when my wife never said a word about my increasingly large wardrobe. She knew, I knew I was never going to purge again. Which turned out to be not true.

Just before she passed away, I decided to throw away “most” of my wardrobe and makeup and even went to the extent of growing a beard. Which I considered the ultimate purge. Even as I did it, something told me to keep my favorite outfit, wig and shoes because I never could be sure when I would need my old friends again. Tragically, six months later I did when my wife passed away and I turned inwardly to my feminine soul for comfort. When I did, I was able to shave my beard and hit the ground running towards a new life. Or, should I say, heels on the ground.

One way or another, I was happy I was not strong enough to totally attempt to purge away my feminine life. It was time to open a new chapter, even if I was sixty, as a transfeminine person. It seems many of us, with gender issues are doomed to a life of denial. We try to sooth our transgender or cross dresser sides by trips to our mirrors until we are caught, or in a relationship which even makes it worse. We begin to feel guilty about many things such as forsaking our ingrained male habits, all the way to feeling selfish for wanting to do something as radical as changing our genders for ourselves.

A lifetime of purging falls right in line with all the other pitfalls we encounter on our gender journeys. We must be strong enough men to make it to transgender womanhood and purging is just another experience we have to go through.

As always, thanks for reading along with my writings and experiences! Your comments mean a lot to me also. They help me to know if I am headed in the right direction. Please keep them coming!

 

 

Monday, August 4, 2025

Kicking and Screaming.

 

My trans friend Racquel
with her fur-baby.

Sometimes I am asked why I waited so long to finally make the serious transition into a transfeminine world at the age of sixty.

The partial answer is I did not want to face up to my truth of who I really was. Instead, I internalized my gender desires as long as I could. Another reason was, I had a powerful male self who did not want to give up all the white male privileges he had fought to gain. Every bit of ground he lost to his transgender sister was hard earned. Plus, he had a powerful ally with him in my second wife who wanted no part of me to progress any further than the cross-dressing stage I was in when I met her.

My excuse is for not transitioning sooner goes past just ignoring the obvious. I just did not factor in the other major changes I would have to go through just to see if my dream of living as a trans woman was even feasible. Maybe I could never make it at all was a fatal flaw in my thinking because I needed the inner confidence to live. At that point, I opened my gender closet door and began to look around and my male self was dragged kicking and screaming into the world. Early on he was being laughed at in drag when he went out which hurt his male ego. Until he summoned up enough skill to stop the abuse.

All of this led up to finally realizing (for whatever reason) I was more than a cross-dresser. I was a transgender woman. It all led up to the scary, magical night when I decided to change my mind set when I went out for a drink in a venue, I had frequented many times as my male self and had always wondered what it would feel like to do it as a woman. As I said, I was scared to death, and sat in my car for what seemed like forever adjusting and readjusting my hair and makeup before I went in. I knew from previous visits, when the nearby mall closed, the bar would fill up with single professional women who just socialized with each other. As I steadied myself to go in, my male side was still screaming no as my feminine side was excited to finally get a chance to live. That night, for the first time, she had won the battle because I had a great time and even stayed for an extra drink just because I could.

Little did my feminine side know, winning one big gender battle would only make the war seem further away. Following the evening out, she wanted more which caused severe problems with my marriage and life. Deep down, I wanted to experience the thrill of feeling natural in my skin for the first time, and when I could not do it, I became depressed and downright mean to the world around me. Internalizing my gender issues became less and less of a way to run my life. As a result, I started to sneak out from the house any spare moment I had to attempt to reinvent myself as a transgender woman.

I learned I could and began to slowly carve out a new life for myself with people who knew nothing of my past male self who was still strongly resisting every move I was trying to make out of my closet. Sure, I had my ups and downs with what I was doing but my overall trajectory was up, and I was proud of myself. I had come so far from the early days I had admiring myself in the mirror. Even the kicking and screaming from my male self was beginning to fade. But I found not to be too confident because I still had a long way to go on my gender journey to be a full-time transgender woman. Since my trans woman friend Racquel always told me, I passed out of sheer will power, I always had to work harder to make it in the world. I would forever have a testosterone poisoned body my male self-had left me to work around since I did not have the finances or will power for expensive facial femininization surgeries like Racquel did.

So, I did the best I could and managed to build a small tight knit group of women friends who accepted me while at the same time instructed me on the finesse points of being a woman. All of it brought the final curtain down on the kicking and screaming of my male self. I just wish he had not been such a formidable opponent. On the other hand, his interaction kept the bullies away from me for the most part and allowed me to get through the military in one piece, so all was not bad.

The end result was, he never felt as if he was the most natural person for me to be. That distinction always went to my feminine side who never gave up winning my own gender war. She ended up just ignoring all the kicking and screaming until it finally went away and the lack of extra noise in my life was a welcome change.

 

Sunday, August 3, 2025

Purging

 

JJ Hart from back in Ed's and Michelle's
time.

For many transgender or cross dresser women, rarely have we lived a life when we never wanted to go back to our male selves. A common term for the practice is called “purging.”

Like many of you, I have experienced my share of trying to purge away my gender issues. About the time I thought I was entering a high-profile stage of my feminine life, I began to feel guilty and wanted to throw it all away. Then, I learned there were different stages of purging. For example, when I was purging, I never could seem to throw out or give away all my hard earned, cherished feminine wardrobe and makeup away. Deep down I always left the door open to my closet for a return to cross dressing as I called it back in those days.

Then there was Ed, an acquaintance I had who really defined purging to me. Ed was a frustrated cross dresser who at the least was having problems with his family and at the same time dealing with several very serious health problems. Before he reached a crisis point with his health problems, he decided to give away all his cross-dressing items. With Ed, that meant a lot. He needed to empty out an entire storage unit he rented to hide his wigs, wardrobe and makeup from his family. I turned out to be on the receiving end of his gifts. He gave me a nice set of silicone breast forms he purchased as well as a plastic tackle box full of expensive makeup.

What ever happened to him I will never know, the last I heard from him was decades ago when he was increasingly becoming more and more negative concerning a transgender friend of ours. Michelle was very beautiful and was headed towards gender realignment surgery, and I think Ed had developed deeper feelings for her than just friendship. He never confided in me if that was the case which leaves me to yet another unclosed mystery in my life. Along with what my deceased wife would have thought of me if she ever knew me as a more complete transgender woman.

Even as I continued to progress along my transgender path, I found myself to be a contradiction of terms. I did not know for the longest time how I fit in on the gender spectrum. I had an idea I was more than a casual cross dresser such as Ed was but was I as serious about becoming a fulltime woman as Michelle was. Being in the middle as always tortured my frail mental health as I did not know which way I wanted my life to go.

Initially, I decided I could take the pressure no longer and purged my feminine fashion and makeup…almost. I compromised and did not throw out my favorite wig, sweater and Ed’s silicone breast forms. So, I had left the door wide open to return to a life I had always thought deep down, I could never leave behind. Slowly but surely, I rebuilt my wardrobe, added another wig and purchased new makeup to fill Ed’s tackle box I still owned.

That was the last time I tried to purge my physical belongings, helping to calm my transfeminine longings down. Following the many times in life I attempted to purge my life away from my deep-seated gender desires, I finally learned that I could not easily throw my real life in the trash. I also lost track of Ed and Michelle long ago and the last I heard from Michelle was she had gone ahead with her gender surgeries and was living with a lesbian in nearby Columbus, Ohio.

I just wish I had the foresight to understand how close purging was to my overall wellbeing than the obvious. All along, I thought I was trying to rid my feminine self of her external possessions when in reality, I was proving the futility of trying to deny the person I was always destined to be.

In a full circle moment, I was able to grow my own breasts thanks to gender affirming hormones or HRT and donate my silicone breast forms Ed gave me to a swap out at a transgender-cross dresser support group meeting I attended. As I mentioned, he had very serious health issues, and I doubt if he is still alive today. In a moment of clarity, I remembered his full name and searched for it on Facebook to no avail.

One way or another, I view purging yet another unique sideline of following a gender path. As far as I was concerned, I not so slyly resisted completely throwing away all of my wardrobe, shoes, wigs and makeup I acquired. I never knew when I would go back, I just knew I could.

A Thing of Beauty?

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