Shopping 201

Image from Brett Jordan
on UnSplash

Over the years I did quite a bit of shopping in clothing stores and malls, mostly successfully.

It took a while but I finally learned much of my success had to do with the fact my money was more important than my gender to the average store clerk. Many I think worked on commission and anything they sold was added to their paycheck. Even still, the experience was valuable in building my confidence as a novice cross dresser in the days I was running from the idea I could be transgender. I was paying my way to people so they would be nice to me. Only one time did I run into any problems when an older clerk told me my skirt was too short. In response, I left and never returned since there were plenty of clothing stores to go to.

In a short period of time, I grew tired of the same old shopping I was doing and started to expand into stopping for lunch where I needed to interact one on one as a woman with servers. The entire process opened a whole new gender world to me and for the most part I was treated politely with respect. Overall the process took me to a whole different level of Shopping 101. I grew bored and was ready for a new course I called Shopping 201. 

The new course ended up providing me with endless possibilities to expand my horizons as a very serious cross dresser. At the time, I was searching for ways to do different things in the feminine world. One way to sneak around behind my wife's back was to start doing part of the grocery shopping. I would pick times I knew the grocery store we went to would not be busy and out I went. The women's fashion trends back in those days fit me well. I could wear one of my oversized soft sweaters along with a mini-skirt and flats and look like any other fashionable woman without going overboard. One morning in particular was memorable. 

On the day, I carefully shaved my legs and prepared my wig. After dressing and putting on a light amount of makeup I took off to the grocery when my wife was at work. I arrived at the store, grabbed a cart and proceeded to pick up a few needed items. Then I headed up to the register line to be checked out. This was back in the days before self checkout so there was only one way to go. At the register there was one older cashier and one kid bagging groceries. When he saw me, his eyes immediately went to my legs and when he noticed me watching him, he blushed and stammered something about helping with my groceries to the car. Never before and rarely since have I affected a male such as that. The cashier just gave me a knowing smile. 

From there, I couldn't resist reverting back to Shopping 101 and made a quick stop at a nearby big box store to pick up another pair of panty hose and shop for new makeup. By doing so, I was able to hide my expenditures along with what I spent at the grocery store. 

I was able to negotiate the morning as my feminine self and learn so many new things so I could graduate Shopping 201 and move on towards life in a transgender world.   

Going Back

Image of Liz on left and Daughter on right
from the Jessie Hart Archives.

 Recently I read a rather sad post from a person who was giving up her gender transition and going back to her original life. 

Even though I consider myself very fortunate in how my gender path turned out, I could understand the facts the person mentioned when it came to her new life. Among other things, the person related experiences which have haunted many of us following a transition. Such as having problems with loneliness, finances etc. So many transgender women are stuck in their houses, often with just having a computer to provide any contact with the outside world. This de-transitioner was older and provided a picture which showed a very presentable senior woman. My heart broke when I saw her image, I just can't imagine going back after putting so much work towards accomplishing a goal. Perhaps it is because I tried so hard and risked so much when I crossed the gender frontier. Plus, possibly for one of the few times in my life when I ever set specific goals, I was able to achieve what I set out to do. 

One of the major differences I saw when I read the post was how I approached the gender goals I was attempting to accomplish than most others. One of the examples was how I approached on-line dating services. I went all in with three or four services with the usual results of receiving tons of trash back in the process. I tried everything such as woman seeking woman to man seeking man. Amazingly, when I was giving up, some how I ended up meeting my current wife Liz who lived within driving distance in Cincinnati, a city I had always loved. That happened over ten years ago and it all started with a date to a drag show. As an aside, Liz identified as a lesbian witch so I was intrigued. 

In addition, the lucky move I made to create a new social life came when I decided to not go to anymore male gay venues and decided to go to the sports orientated big venues I was used to. I figured if I was going to risk being discriminated against, I might as well go to a place where I could enjoy myself. The gay bars aggravated me because I was always treated as a drag queen. What I don't recommend is the amount of alcohol I consumed along the way. On the other hand, I ended up meeting several other women in the venues who became friends. 

Very quickly, going back in my transition never had to be an option. By the time I decided to go all the way as a transgender woman, I knew my daughter would support me as well as Liz and my small circle of friends. As I made the final slide down the gender slope my landing turned out to be very soft. Even still, my heart goes out to those who are considering going back. Perhaps the whole experience could be thought of an ultimate experience which failed. Or maybe, they just wanted their old male privilege's back. 

Then again reversing my life again would be unthinkable because I would be so unhappy. I am afraid the person who did decide to go back would never be happy on either side of the binary gender border. 

Changing the Gender Locks

Image from Adam J
on UnSplash

It took awhile for me to change the locks on my old male self. He kept hanging on and on to the smallest reason not to go all the way with my gender border crossing.

Through it all, he was quite comfortable on occasion taking advantage of all the male privileges he had come to take for granted. He was used to taking personal security and even intelligence for granted. Age seemingly was the only prerequisite in gaining respect. When the locks were changed years ago, life changed with it. 

Changing ones' gender is nothing to be played with. I'm biased but I think transitioning as a transgender person (woman or man)is one of the hardest things a human can experience. All the cards are stacked against you as early in life you are forced into a square hole when you are certainly a round peg. Perhaps the interesting fact of the whole gender experience is when one door opened and you went through it, often it was slammed shut and locked behind you. You then had to be quick on your feet and learn what to do next. Surely mistakes were made but it was the only way to learn. Some would call it tough gender love. 

The farther I went in life as a novice transgender woman, the more locks I needed to change. The more I entered the world and was successful as a feminine person, I felt natural and couldn't wait to lock the old male door behind me. Even when it led me to potentially dangerous situations. I write often of the times I was on the verge of being seriously molested or worse in my early days of exploring the world. One night I was dressed way to skimpily and attracted the wrong set of man. My second wife needed to bail me out of the situation so I never heard the end of it. Even still I locked that door behind me and moved on with an important lesson learned. 

I was doing what I believed in so I was stubborn and any progress gave me hope. To follow in someone else's path would just have not worked. So I said to hell with the possible consequences such as losing my three "F's" family, friends and finances, I kept changing the locks behind me. I needed a huge lock as well as amazing amount of duress and thought before I decided to go through with donating all of my male clothes and deciding to live a fulltime life as a transgender woman. Also, hormone replacement therapy was in my future should I decide to explore the possibilities of furthering my femininity through HRT.

Along the way, I became very proficient at changing my gender locks and hiding them from the everyday world. Depending on the door, often I had to stop and look around at a totally new and exciting world. Once I did, I always decided to move on seeking a new door to go through.

A-Ha Gender Moments

 

Image from the Jessie
Hart Archives

Since I have been fortunate enough to live a fairly long life, I have experienced several a-ha moments when it came to my all important gender needs. 

When I started my gender journey as a youth, even though for the most part I considered my desire to cross dress my boy self as a girl to be a fairly innocent hobby...unless I was caught. Looking back, I don't know how I managed to hide what I was doing. 

Perhaps my first a-ha moment came when I was able to save up enough of my own meager funds to buy my own makeup and pantyhose. Sure I was petrified but somehow I made it through and was emboldened to do more. The whole process was to set the stage for more gender adventures and a-ha moments or being scared to death but loving the feeling of success.  

A few of the biggest moments I mention quite often and I am sure I will remember them when if and when my life flashes in front of my eyes when I pass on to the other side. One was the night I decided I would make the effort to go out as a transgender woman and quit thinking of myself as a cross dresser. Knowing full well, there was nothing wrong with being a cross dresser, I just needed more since I was increasing how many times I was going out and the venues I was attempting to go to. On the night in question, I ended up in the parking lot of a nearby "Fridays" venue gathering my courage to go in. The end result was predictable as I was to discover later. I lived and was treated with respect. I had done so much more than just interacting with store clerks in the mall. 

The more a-ha moments I had, the more emboldened I was to try more. For the most part I was successful except when I tried a couple redneck venues where I was roundly rejected. I guess you could say I had different a-ha moments when I had the cops called on me. I learned the hard way and kept on trying. When I tried, I was able to find more success in my quest to see if I could live fulltime as a transgender woman. As I progressed, on occasion I was elated and couldn't stop thinking how I could fit in to the feminine world but other times when I thought of the enormity of what I was thinking of doing. My male self and wife were fighting me at every turn so life was not pleasant. 

As it turned out I out-lasted both of them and finally came to the conclusion I needed to transition fulltime into a world I had only had ever dreamed of. It was a huge a-ha moment and took a ton of pressure off of me. From there, it was a short jump to deciding if I should undertake hormone replacement therapy or HRT. HRT was yet another major moment of success. My body took to the new hormones as if I should have always been on them. 

The only problem I faced at that point in time was my feminine inner soul taking over my life. She had waited so long and proved time and time again she knew what to do if I would just trust her. 

As I near the age of seventy five, I am sure the a-ha moments maybe will be less numerous but more dramatic as I face the final hurdles of life. 

Virtual Outreach

Image from the Jessie Hart
Archives.
Ohio River in background...

 Recently I experienced a busy day virtually on the old laptop.

First of all, I needed to go through the pre screening process for another colonoscopy. I just had one a year ago but the doctors removed a sizable polyp which fortunately turned out to be non cancerous. Even so, instead of waiting the usual three years between check ups I was scheduled for to come back in a year. If you are not familiar, colonoscopies are not the most pleasant procedures to go through but on the other hand, having intestinal cancer is a terrible alternative. 

I don't know how many of these procedures the Cincinnati Veteran's Administration hospital does a year but the woman doing the intake on the phone almost immediately said, I remember you. Being transgender I am used to being remembered. However, this is one of the times I would have preferred not to be remembered. The woman I was talking to on the phone possibly reacted at my often poor attempt to sound feminine on the phone. Part of my transition I am always working on. Hopefully this time, I won't be miss-gendered when I go in early January for the procedure as I was last time.

The second part of my virtual day occurred later on when I attended the monthly meeting of the Greater Cincinnati Alzheimer's diversity committee. As always the meeting was very gender affirming as the other four participants were all women. It's almost as if I was in another mini girls night out. Plus, I am a big believer in helping anyway I can with the association because years ago, my Dad passed from having Alzheimer's. When I approached them to do more, I was pleasantly surprised to learn the association already had some guidelines in place to deal with LGBTQ patients. However as we all know, being transgender presents more unique opportunities we have to encounter than the rest of the gay or lesbian community. 

One thing I have had to do (which I have been putting off), is write a short post for the Association's Facebook page. It should be noted several of the members have made it a point to go to several of the regional Prides this summer to help publicize what programs are offered to help those in need. So hopefully I will be just aiding in the process. 

I also write for the local transgender - cross dresser monthly newsletter and each time I encourage anyone else to wants to become involved a path to do it. So far, no one has come forward to volunteer which is no real surprise because so many members are still deep in their closets. On a wider scale, if you have ever been touched by Alzheimer's and have time to spare, seek out your local association and see if they have a diversity committee to volunteer with.

One thing with a virtual day is, I need to apply makeup and fix my hair which is always good. In addition to my virtual appointments recently, I also had another one a couple days ago when it was time for the Dayton, Ohio VA LGBTQ support group. I learned then my long time (ten years) therapist is leaving for another job. I was very sad because I have always looked up to her as one of the top three influencers in my life. It will be interesting to learn if anyone else will run the group. 

Now, for awhile, life will settle back down as Thanksgiving has now passed us by and it has occurred to me I have not written about my family experiences yet. Where does time go?

Stuck in the Middle with Me

 

Image from Rene Ranisch 
On UnSplash

Once upon a time and probably more than once, my second wife told me my cross dressing existence wasn't all about me. 

We were usually fighting about my feminine existence when she came up with the same comment. The unfortunate truth was it was all about me. I had a singular desire to look better as a woman and I knew deep down the whole femininization process would not be accepted by my wife and if I was to succeed at all, I would have to do it myself. Since she was unable to help, it meant I was on my own to discover my own fashion, makeup etc. So, for the most part, we never saw eye to eye on anything when it came to my cross dressing. Over the years, it became obvious she didn't like my inner woman at all.

Even though I knew it was and had to be all about me, life went on and we were able to stay together for over twenty five years until her untimely death. Until the end, she resisted any idea of mine I would ever want to begin down the road to trying a transgender lifestyle by starting hormone replacement therapy. When she always stated she didn't sign up with me to be with another woman again I had to agree with her.

Since she did not accept me, I started to sneak around behind her back and found out it was possible I could follow my ultimate dream. In the world I was beginning to discover, I was able to begin to carve out a new life as a transgender woman. When I did I became stuck between the two binary genders. I was trying to live as my old male self a couple days of the week and my female self the remainder of the time. Of course my life became unbearable and I sustained dark days when it came to my mental health. Being stuck in the middle with myself was not a fun place to be. I would come to learn in her own way, my inner woman who was doing battle with my wife was just as strong willed. 

I quickly figured out my old male person was going to be the first person to go away when my wife passed. I'm sure in the next life, my wife wasn't surprised to see I quickly transitioned totally into a feminine world. She always said my dog would never miss her if anything ever happened and she could have added my inner woman would not have missed her either. To make matters worse with my overall mental health, my male self desperately missed her. Possibly knowing my wife was his last chance at maintaining any sort of life.

 Even though the times I was out exploring the world as a novice transgender woman on occasion I was terrified, I pushed on to experience the excitement of exploring a life I had always dreamed of. When I did, often I was surprised at the outcome. I never expected many of the results I had when my inner feminine self took over. Quite a few times I couldn't believe how easy and natural life turned out to be.

Being stuck in the middle with me turned out to be worth all the hassles I went through to arrive there. 

Gender Variables

Image from the Jessie Hart
Archives

When I was first looking at myself cross dressed in the mirror and when the mirror was lying to me, I felt as if I was well on the road to understanding what my life may be like if I ever had the courage to transition.

Of course I had no idea of the obstacles and challenges I would need to face as I attempted to live a life I had only dreamed of. There were plenty of times when I woke up in the morning following a vivid feminine dream wishing I was still the female I dreamed of being. The problem being was dreams don't ever equal reality. 

Reality meant I needed to learn all the gender variables I would have to learn the hard way if I was ever be able to follow my dream and live full time as a transgender woman. The first example I ran into was how I was dressing myself. I mistook trashy for sexy and tried to validate myself as a woman by trying to dress as a teenaged girl. Happily, I learned quite quickly I was dressing for the wrong gender. I was dressing how my male self thought I should, when in fact I should have been dressing to blend in with the other cis women around me. Cis women are women who were born female. 

Once I started to be able to blend in with and exist in the world as a visible feminine person, I found out again the hard way, how many gender variables I still needed to face head on. The main issue I always mention is how quickly I needed to learn to communicate in public. Unlike the mirror, these people really wanted to talk to me. At the time, I had barely given any thought of how my voice as a woman would even sound to another person. What I ended up doing was I tried to mimic the woman's voice who was talking to me. Men, for the most part, left me alone so I didn't have to worry about them. I think other women were just curious why I was trying to live in their world. Whatever the case, I needed a vocal or communication plan and quickly.

What I learned was women (as I already knew) operated on a totally different wave length than men. There were to be no more direct conversations which men do so well. I needed to learn the power of non verbal communication clues as well as the passive aggressive nature that women deal with. There were many times I ended up with scars on my back when I thought a smiling face meant support. All a part of dealing with the new gender variables I was learning.

As it turned out, I was learning new layers of the feminine gender I had only dreamed of living. Plus I was ultra confident I made all the discoveries I could when along came  even more challenges. At that point I developed the small group of women friends I needed to rise to the next level of gender variables I needed to face. Often I was terrified but determined to stay the course I was on. 

I learned once and for all what I had always known deep down. Women live a much more layered existence than men. Little did I know I would end up living all the gender variables and then some as I lived my life as a trans woman. 

A Night with the Boys

 

Image from the 
Jessie Hart Archives

Way back in the early days of going to what were known then as "transvestite" mixers, I ended up having a very special experience, In essence, I was still out with the boys, without my wife, it was just they were all dressed as women. 

The evening started innocently enough, with the usual sizing up of those cross dressers around us. A little bit of everyone was there from those cross dressers who were desperately trying to hold on to their masculine selves, all the way to the glamorous "A" listers who formed their own cliques. What I didn't know was during the evening, the group organizers were providing a few makeovers from professional makeup artists. 

I was intrigued by thinking I could be chosen for a makeover if I could fight through my fear to do it. Somehow I managed to land a makeover spot and then had to remove all the makeup I had spent so long to apply. Plus my ego thought I looked pretty good. I was to find out I was wrong.

There were several artists working, of both genders. It turned I was lucky and got one of the guys who were working diligently trying to do the impossible. In my case, he did do the impossible and I went through a magical transformation. To make matters better (or worse), along the way the make up guy was trying to explain all the techniques he was using to transform my face. I did my best to remember everything he told me and in the end run, he helped me to understand things such as the power of using a small amount of blush to highlight certain areas of my face. 

All too soon he finished his work and told me to put my wig back on. I could not believe the transformation and in my mind I was so excited  to show off my new look to the rest of the group. I did receive several compliments which cemented my desire to do more when the "A" listers went out on their own after the mixer was over. They normally went to some sort of a gay or lesbian venue to continue the party. To be able to go, I needed to be invited, so I began to seek out the one of the small group I knew and essentially invited myself along. I succeeded and managed to tag along for a night with the boys, all cross dressed as very attractive women. 

On this night, I was able to continue my own "Cinderella" experience when the group decided to call a taxi cab and go to an even smaller venue which to me looked as if it was a neighborhood tavern of some sort. It was somewhere in Cleveland, Ohio, which is all I remember now. This all happened during the pre-video game era and the place had two pinball machines. After I ordered a drink, I was able to find a couple quarters in my purse and started to play one of the games. Before long, a man approximately my age came up and wanted to play the same game with me so I had a decision to make. 

The rest of the group was wanting to leave and if I stayed, I would have to either call another cab or somehow depend upon this guy I had just met to get me back to the hotel. I made the split second decision to take the safe way out and leave with the "A" listers I came with. Before I did, to rub it in,  I made sure they knew I was approached by a guy and they weren't. 

From then on, I was more or less accepted by the group although I never had their privileged negative attitude which was so judgmental to others. However, from then on I was always searching for another "Cinderella" moment when I was able to spend a night with the boys without my wife. Partly because she normally always came along.

 Sadly, it never came again. 

Role Model

 

Image from Averie Woodard
on UnSplash

I have a close acquaintance who is taking a giant step forward in her transgender world.

She is stepping out of her comfort zone and will apply for a new job as her authentic feminine self. I was fortunate to be at one of her first attempts to explain why she was coming out of the closet which was tormenting her so much. I remember thinking at the time how far she had to go on her journey as I wished her the best.

During the following years, she has faced the same issues as other transgender women and trans men face, from marriage issues to kids and family decisions to decide upon. She has been very open on social media about her struggles. Including public pushback when her wife and her go out to eat. She lives very close to me and I know the venues she has had problems in and I understand why. In fact, I have had some problems also in one of the venues and we never went back.

Even with all of that, she pushed on and is now trying to take her transgender life to another level. Her current job is a truck driver which of course presented it's own level of challenge at every stop she made. She transitioned on the job and literally changed  her outward appearance overnight. I really respect the courage it took for her to take on her work world the way she did. Now the challenge she is seeking is to apply for another job (in the same industry) but in a whole different job as her feminine self as a logistical scheduler of sorts. 

If she gets this job or not, she is a true role model for others in the transgender community. To step out of her old gender comfort zone and sever ties with her old life as a man is remarkable.  It's a giant step forward. 

I am far from an expert in finding a job in todays' world. But from what I am reading in Cincinnati alone there are a few companies who are LGBTQ+ inclusive and offer employment possibilities to aid in a person's transition. It's good for both parties as the company can hire a good employee and the trans person is able to take a giant leap forward and support themselves financially in their new world. 

As I circle back to the person I know who is applying for the new job, I am sure this is just the beginning one way or another for her to step forward into a life she has always dreamed of. I hope she gets the job on the first try! 

Even though I am retired and don't have to face the work world as a transgender woman, I can still see a role model when I know one.