Showing posts with label makeup. Show all posts
Showing posts with label makeup. Show all posts

Sunday, April 7, 2024

My Second Gender Transition

Liz on Left. Image from a Banquet we 
attended. From the Archives. 

 I am a firm believer,  I went through more than one major transition when it came to building a new life as a transgender woman. Many transitions were helped along by friends and others I accomplished on my own. 

One of the biggest I did all by myself was one I mention quite often. It was the night I went to TGIF Fridays close to me. Just going was not so amazing, in fact, I had been to the venue many times as my male self. When I was there, I often was very jealous of all the other women I saw there, many of which were dressed in fashion I could only dream of. 

All of a sudden, I decided to make my dreams a reality and one night I set out on an adventure which I would never forget and would change my life forever. I can't really tell you why but something clicked deep inside me and I decided it was time for me to move away from being a cross dresser and explore my possible existence in a transgender world. The whole possibility terrified me more than anything else I had ever tried before in my life. Possibly because I knew if I was successful there would be no turning back. 

To begin with, I had the wardrobe I needed to wear to blend into the feminine environment I was headed. I knew the Friday's venue I was going to had a very woman based clientele which came every night at approximately the same time from a large mall which was nearby. I knew exactly, who I was trying to blend in with when I chose what I was going to wear. I chose my dressy black pantsuit, black flats, sensible makeup along with my shoulder length honey blonde wig. I felt I looked presentable enough to accomplish my goal of moving into the transgender world I was just beginning to explore. 

Once I came up with a time I could sneak out for a trip into the unknown when my wife was working late, I began the transformative femininization process. Once I thought I looked fairly presentable, I left for the twenty minute trip to the venue. Through it all, I was scared but not as scared as I would be when I arrived at the Fridays. When I pulled into the parking lot, I ended up waiting over a half a hour as I adjusted my hair and makeup in my car's rearview mirror. Once I came to the point where I could barely breathe, I opened the car door and gathered myself the best as possible. After all, I had improved from the point of not being to breathe at all to being able to walk in the front doors. 

Since I managed a similar casual dining venue to a Fridays I knew the setup, Essentially, once I made it past the hostess stand, all I had to hope for was being able to find a vacant seat at the bar. I was lucky I arrived shortly before the rush and there were several seats available. The Fridays I was going to had not remodeled yet so it had two big supports on either end of the bar. I was so scared and so lucky, I was able to get a seat next to one of these supports. I got as close as I could and tried to hide until I was approached by a friendly bartender and order a drink. From that point forward, I knew my life had changed forever. Just existing as a woman among other women in a public setting had removed any idea's of being a casual cross dresser ever again. 

In a moment, my second gender transition had taken place. My first came years previous in my youth when I viewed myself as a girl in the hallway mirror. Plus, deep down I knew the next transition I would undertake would be if I could ever undertake gender affirming hormones or HRT as it was known as back in those days. My visit to Fridays that night jump started my gender future. My problem then became how I would ever be able be able to co-exist with my un-approving wife ever again. She was certainly against being with another woman. Especially if the woman was me. So my second transition was heaven for my inner woman and hell for my wife and my marriage.  

Of course, I was able to transition even further with hormonal therapy and go on to lead a comforting transgender life. Going through the process was always not the easiest and I will always remember how I felt that night at Fridays from trying to hide behind a post all the way to how my panty hosed feet felt in my flats. It was quite the evening.

Monday, March 25, 2024

Trans Crisis Management


Image from the Jessie
Hart archives. From the Ohio 
State Student Union. 

Over the years as I went through the process of living my life as a transgender woman, I encountered many instances of crisis management. 

Some of the encounters were funny, some were anything but funny. Several come to mind as I write this post. Probably the most humorous account came at the ill fated expense of a water balloon I used as a breast form one night when I was going out to my regular venues I loved the feel of the balloons. They provided a realistic bounce and even matched my body temperature if I filled them with water of a certain temperature. Of course, as I was doing all of this, I knew how fragile my fake breasts would be. And, a night I remember well, it happened, one of my beloved water balloons broke sending water down my clothes. I was lucky in that I was headed from my seat at the bar to the rest room and had just made it to the safety of the women's room, if it was empty at the time. It was empty and it saved me from any rushed explanations of the water which I caused. The only crisis management statement I could come up with was I was pregnant and my water broke. What really happened was, I gathered my one breast self together and left the venue like nothing happened, then headed home determined to find another form of realistic breasts. 

The next  profound crisis management encounter I remember was one of the worst I ever have had. It happened in another venue I went to regularly. After consuming my usual amount of beer, I naturally needed to innocently use the women's room. When I did, I didn't notice the woman who came in after me and I should have. I saw her and an older woman  I perceived to be her Mom come in the door and pass nearby me at the bar. The older woman wasn't shy about glaring at me but kept on going, minding her own business. I should have known my relaxation would come back to haunt me because when I came out of one of the stalls in the restroom, I was confronted by the daughter. Out of the clear blue sky, she started screaming at me and began her tirade by calling me a pervert. 

At first, my fight or flight mechanisms kicked in and my first inclination was to vacate the rest room. Instead, my inner female kicked in and faced the red faced screaming woman. Somehow during her rant, I was able to learn she ran her own hair dresser salon. When she slowed down, I asked her for a business card so I could pass it along to a very influential local LGBTQ organization and naturally tell them about my negative experience with her. It worked because she abruptly stopped and left the rest room while I not so calmly washed my hands, checked my makeup and returned to my seat. The whole experience taught me to always be aware of my surroundings and other potential problem people in it. 

Of course, these two examples are just the tip of the iceberg when it comes to dealing with our own brand of trans crisis management. From makeup and fashion  struggles when we first come out of the closet, all the way to unwanted government discrimination, we face it all. I am sure all of you have faced your own crises over the years. Maybe going back all the way to being caught cross dressing in your Mom's or sister's clothes when you were growing up. Surviving it all was the challenge while preserving our mental health. Sadly, with the extremely high rates of suicide in the transgender community, too many don't make it. In fact, we just had a local trans musician commit self harm and die last week. 

Crisis management with all of us just needs to be a priority. 

Saturday, March 23, 2024

Leaving me For Years

Image from Brock Wegner
on UnSplash

I become a little amused when someone thinks I overnight completed my gender transition from a fairly successful male to a struggling novice transgender woman. 

To put everything in perspective, it took me nearly half a century to figure out my gender issues and how I needed to deal with them. Perhaps you noticed I used the word needed and not wanted because deep down I knew I never had a choice in my life. My gender journey was pre-written for me and I just had to follow the script.

For me it meant dealing with years of extreme gender dysphoria which wrecked my life and several relationships along the way. It was an extreme struggle for dominance from the two binary genders which lived within me. Naturally, even though he wasn't happy or satisfied, my pre-destined male life just didn't want to give up all the male privileges' he had worked so hard to gain. While, on the other hand, my feminine side had to put up with the fact she felt so free and natural when she was let out of my gender closet. 

The struggle left me in a situation for years where I couldn't win. I was in some sort of a gender trench warfare when one side had a little success, the other side would come back to reclaim victory. Battles were won, purges were made but the war went on and on. First I tried to hide in the mirror but that didn't work when I began to escape into the world as a cross dresser. All of a sudden, I discovered I might be actually able to live a dream life as a transgender woman if I worked hard enough to do it. At that point, I sat out to take better care of myself and lost nearly fifty pounds so I could fit into the woman's fashions I so admired. Plus I started to take better care of my skin so my makeup was easier to apply and I looked more natural doing it. 

At that point, I tried to outrun my gender dysphoria the best I could by changing jobs and locations where I lived way too quickly. In a space of three or four years my second wife moved from our home in Ohio to the metro NYC area, back to a very rural area where we heated with wood and finally back home again. All I finally learned was I couldn't out run my problems. They all began and ended with my gender issues. 

Even with all the problems I mentioned, I still did not want to give up totally on my male self. In many ways, the life he had carved out from such a bleak beginning was just too comfortable. What happened then were the years I spent as a novice transgender woman. All of them were scary yet exciting times to live through. 

So no, my decision to leave the male world behind was not an overnight decision. It just turned out he was leaving me for years. 

Friday, March 22, 2024

A Transgender Inch Equals a Mile

Image from Jessie Hart Archives
Civil War Cemetery Cincinnati

Distances are often very blurry when it comes to beginning and pursuing a gender transition. 

The meaning wasn't lost on me when I began to remember what many of my more experienced dating male friends said when it came to discussing their girlfriends. The biggest complaint was when the guys gave in an inch with their women, the women took a mile. 

As I transitioned into the feminine world, often I thought the same thing about my inner girl self. Or, as soon as I cross dressed in front of the mirror, the more she wanted. Specifically, she wanted out of the mirror and into the world. Quite early, it meant making the trip to the mailbox to check to see if there was anything in the box. I so enjoyed the feel of the outside air on my freshly shaved, panty hose covered legs. 

What I discovered was as soon as I made the very short trip out of the door, my girl dreamed of doing more and more in the world. So much so, my entire life was effected to the point I would become very grumpy almost to the point of disorientation when I couldn't cross dress again. The whole process just didn't seem fair because I was doing the best I could with the very limited resources I was able to put together. Fashion was difficult to find for my rapidly growing body but I could manage to buy my own makeup with my very small allowance I earned plus the money I put together from having my own newspaper delivery route.

Through it all, I managed to get by when my inner trans self wanted to take an extra mile when I was giving her an inch. I thought it was some sort of a gender poetic justice when my male friends complained about their girlfriends and I knew exactly what they were talking about when I wasn't outwardly involved with a girl at all. 

It wasn't until much later in life when I could begin to give up more than just an occasional inch to my transgender self and discover all I was missing. More and more I was able to take the extra mile. Even though I was scared (or even terrified) to do it. Such as the first night I went to a "Fridays" bar/restaurant for a cocktail. I ended up sitting in the parking lot for a good thirty minutes checking my makeup before I gathered the courage to go in. Once I did, and began to breathe again, I was able to relax and enjoy myself.

At that point, I was very proud of myself and considered I wouldn't challenge my novice transgender woman for more. After all, I had just given her the mile she wanted and I thought she should be satisfied for awhile. Needless to say, none of that worked. Instead of going to the so-called gay venues she had been going to, she wanted more of the "Fridays" vibe she succeeded in. I found she could become a regular fairly easily by being friendly, minding her own business and above all, tipping well. All of a sudden, a new life was beginning. No matter how scared of it I was at the time. 

Perhaps the biggest transgender inch becoming a mile was when I started gender affirming hormonal treatment. In what seemed a very short period of time, my body femininized as well as my inner self. I was feeling more emotional than ever before in my life as the new hormones took effect. The whole process was close to running a record setting mile. 

All along, my old male self was fighting giving up every inch he could. Not wanting to lose his life and all he had worked for. It turned out, once I went all the way into an new exciting transgender world, he lost the battle and the victory belonged to my stronger half. My feminine self as she took the final mile.

Thursday, March 21, 2024

Walking the Transgender Tightrope


Image from Johannes Plenio on 

I have never been accused of being coordinated at all which completely held me back when it came to me being able to participate in any sort of athletics except for football which often meant dealing with brute strength. 

Little did I know, I would have to develop my own sense of gender coordination to deal with my gender dysphoria. It turns out the better I became navigating the world as a novice transgender woman, the more balance I would need to survive in life. What happened was, the better I became with makeup and fashion, the more confidence I felt and in addition I was gaining the all important confidence to try more and more exciting yet terrifying experiences as my feminine self. 

Doing the more I could possibly hope for led me to trying to walk part of my life in my old male gender and part in my newer female one. My second wife even approved of a plan where I could have three days a week to leave the house dressed as a guy, go to a motel, cross dress as a woman and basically do whatever I wanted. Then dress back into my boring drab male clothes and come home. It didn't take long for me to become bored with this arrangement and I began slipping out of the house behind her back when she was working. Out of sheer willpower I needed to begin being more coordinated in how I was trying to run my gender conflicted life. There was really only one thing I knew for sure, I loved my feminine side and wanted to do more and more to let her out. 

Sadly, the whole process of trying to balance the two genders fighting for dominance within me was destroying my already bi-polar fragile mental health. I tried therapy and for years had only one therapist tell me the truth...there was essentially nothing I could do about wanting to transition into a transgender woman. I was what I was and I should accept it. Of course I wasn't smart enough to take her advice. I still wanted to save what was left of my long term marriage to my second wife while at the same time exploring what could be possible if I actually had the courage to transition into a fulltime world as a transgender woman. 

Finally, after falling off the tightrope more times than I can say, I could take the mounting gender pressure no longer and tried suicide as a solution. Just before my wife passed away from a massive heart attack, I thought I "purged" for the final time and got down from my tightrope. I grew a beard, gained a bunch of weight and overall was miserable but I gave it my best effort. 

I proved to myself I wasn't coordinated enough to navigate something complex enough as a gender tightrope and moved on to living a life as my authentic self. I am not one for regrets but if I allowed myself one, it would be I would have had the courage to transition earlier in life (before the age of sixty.) I would have saved myself so much time, effort and frustration as I attempted to balance my gender tightrope.      

Sunday, March 17, 2024

A Rare Night Out with Family


Image from
the Jessie Hart

After my appointment with my veterans doctor, I forgot my wife Liz and I had agreed to meet up with her son for a rare night out at our favorite Mexican restaurant. 

It was welcome news for me for several different reasons. First of all, the evening was a chance to get out of the house again and experience the world. I spend way too much time in the house. Liz has been encouraging me to get out during the day when she works and  I could write my blog posts and even might encourage me to begin work again on my second book, which I have long put off. So I take responsibility for at least not taking our laptop to a nearby library to write. The move would help me to re-improve my makeup skills as I get out in public again.

Secondly, yesterday, since I had already applied a light amount of makeup for my doctor's appointment at the Veterans Administration, I would just have to lightly update it for my evening out with Liz and her son. Being the basically lazy person I am, it gave me time to catch up with an afternoon nap I need because I am old.

Before we left for the restaurant, Liz and her son had the time to catch up on life, not to mention when we arrived at the restaurant and were seated. The venue is very casual and I even didn't need to change clothes except to add a light fleece jacket/top my daughter gifted me for my last birthday. We had major storms pass through the night before which killed three people not too far away from us in central Ohio and dropped the unseasonably warm spring temperatures we had been experiencing. So the fleece was a welcome addition to my wardrobe. Once we arrived, I noticed the venue was almost full, including many families, which normally is good for me not getting noticed as a transgender woman, just another customer. When I did, gender euphoria set in for me.

Dinner was enjoyable, the food was great as well as the company, the server was just interested in getting us served and on our way, so he did not pay me any extra attention one way or another. Which again was a good thing.

Certainly, getting out again was good for my mental health and well being. Can't wait to do it again. Unfortunately our upcoming appointments are with our doctors. It will be interesting to me to see how the dermatologist's perceive the skin growth I have on my face. It could be nothing or something they are concerned about such as cancer. Which of course concerns me deeply. But I will cross that bridge when I come to it.

Wednesday, March 13, 2024

Making it all Effortless

Image from the Jessie Hart Archives

When I decided to go all out and attempt to go public as a novice transgender woman, I found I had plenty to do before I go conquer the world as my authentic self. 

Reversing all I had learned to try to fit in to an unwanted male world proved very difficult to accomplish. Even more so when I learned I needed to make the gender transition seamless and effortless if I was to survive. The first problem I had to beat was getting myself out of my mirror. Just posing in my spare time cross dressed as a woman wasn't getting it anymore. Deep down, I knew I needed more if I was going to survive in my scary new world.

As I attempted to put my new feminine self into focus in the real world, I knew I needed to put away all my deeply ingrained male mechanisms. The prime example was doing away with my permanent leave me alone scowl on my face. I needed to replace it with a softer, kinder gentler look. I needed constant reassurance from myself to make it happen. Primarily because I didn't want anyone approaching me. I found out the hard way my methods were completely unfeminine and I was coming off as a bitch or worse yet, a miserable mean human being. I even was called a big mean woman in a clothing store one day by a little girl, so I knew I needed an immediate change.

The second most profound change I needed to make was how I moved as a transgender woman. Of course, it is no big secret women move differently than men and even though any added dimensions to my hips and butt were due to foam padding, I still had to practice overtime to accentuate my new figure. What I resorted to was trying to practice every second when I thought I was alone trying to walk like a woman. The problem I always encountered was everytime I thought I had put the total package together of makeup, hair and fashion and put the movement with them, I needed to go back to my male world and try to forget the whole thing. Through it all, I became very frustrated. I was having real problems making my whole feminine image effortless. 

Even still, I continued to make it a priority and finally began to see improvement in how I was perceived in the world as a transgender woman. I know, athletes call it "muscle memory" when they repeat a motion over and over again until they get it right and that is exactly what I needed to do. I started to look the public in the eye when I communicated with them and paid attention to what they were saying to me. By doing it, I was able to more precisely tell is someone was reacting negatively to me because I was trans and then what could I do next time to improve my presentation. 

Making it all effortless, did take a great amount of work but it was what I needed to do to accomplish my goal of leading a life as a transgender woman. Plus, I could not have done it without closely observing all of the women around me and the many ways they reacted to the world.    

Sunday, March 10, 2024

The Blue Coat

Image from the 
Jessie Hart

Many years ago I frequented a wholesale coat store which seemingly carried an endless inventory of women's coats including many in my size. Which was rare.

I used to make the store a regular stop on my circuit of favorite places to haunt looking for a coat I could not afford. Even at the store's sale prices, finding one would still be a struggle.  One day I was there was an extra special day when I saw and then slipped into a powder blue wool lined three quarter length coat. Once I tried it on, it was lust at first sight. It seemed to fit in perfectly with my honey blond shoulder length wig I was so fond of. 

The problem I had was one of the usual ones many of us encounter as novice cross dressers or transgender women have, And, where is the money coming from for our new fashion discoveries and would the new fashion really be worth it in the long run. At that time, I was still struggling to hide any extra money I could from my wife who was a trained book-keeper and kept track of our finances. If I was going to my usual thrift store, it was easy to hide my limited expenditures from her and not be afraid of making a huge fashion mistake. If I did, I could simply take the item back and let someone else make the same error without losing much money in the process. 

This time though, as much as I wanted to, I couldn't leave the thoughts of how great it would be to be able to buy the cherished blue coat. In desperation, I kept going back to the store and then modeling it in front of one of the many mirrors. At one point, I wondered if I was parading the coat so much that someone would finally notice me and tell me to buy the coat or leave it alone. Luckily, that never happened but on the other hand I was never able to get together enough cash to purchase the blue coat and make it my own. Plus I had no idea where I would be able to hide it where my wife would never notice.

During this point of my life, I was completely entranced or obsessed with looking like a woman. Particularly a well dressed professional transgender woman in a mall or restaurant. My wardrobe at the time included a black silky pantsuit I loved as well as a pale green jacket I paired with a matching mini-skirt and kitten heels. Those were the days of colored opaque pantyhose and I even managed to find a pair of hose which also matched my outfit perfectly. 

Ironically, when I look back to a decade or so ago when I started this blog thanks to urging on from friends such as Connie, I can't believe how much I have changed. In the early days, I still believed being a success as a potential transgender woman was just looking the part. As I progressed I learned I was so naïve and I was looking ahead at so many layers of learning what it really meant to come out as my authentic feminine self. Leaving the mirror behind and entering the world was terrifying and extremely challenging at the same time. All the years I spent studying the women around me helped but I discovered it was only the beginning. 

Through it all though, I still remember how much I wanted that blue coat and wonder if I would have continued to cherish it as much as I did in the beginning for years. Or, similar to so many other lustful encounters in my past, it would have lost it's newness and just fade away.    

Thursday, March 7, 2024

Gender Truth


Ripley, Ohio Image from
the Jessie Hart Archives

Following years of living a huge lie, I decided to live my gender truth. All along, I should have never been a male and felt so natural and alive when I was being feminine. 

As with any lie, you need to be more and more skillful to keep the ball rolling and not be discovered. The process all started when I was a kid and was carefully hiding away my small collection of girls clothes and makeup. Some of the items, I "borrowed" from my Mom when she discarded them and others I was able to purchase myself with funds I earned doing odd jobs around the house and from my newspaper route. I will never forget the first trips I had made to stores in nearby downtown Springfield, Ohio to buy makeup. I was scared to death since my Dad worked close by and I thought for some reason he might catch me there. Even though, it was my money and I was spending it the way I saw fit, I still felt guilty. The truth of my life still escaped me as I did my best to live in the male world. 

Somehow I was able to hide away all my clothes and makeup and even managed to shave away the hated hair which appeared on my legs when I became a little older. Probably, I was shaving my legs earlier than some of the girls I knew with strict Mom's who wouldn't even allow them to use lipstick. Looking back, I am sure I would have had the same problems with my Mom had I been born female. I just know she would have tried to restrain me the same way she did when I was her oldest son. All she really accomplished was enabling me to be more skillful in hiding my truth. I think. At the least, nothing was ever said to me by either of my parents.

As I cross dressed my way through college and my post military days, hiding my gender truth became increasingly more difficult. Primarily because I was slowly doing more and more in the public's eye as I left my closet to explore the world. The new truth I needed to face was how or if I was going to tell potential spouses who crept into my life. Even then, it seemed to be extremely unfair to both of us to not come clean from the very beginning. Except for my first fiancé, none of my future wives held my gender truth against me. Primarily because of a Halloween party, my first wife attended also, she was around when I confessed to a very small group of friends my costume was more than a casual fling to dress as a woman. As the years progressed and I became more assured of my gender truth, I decided I needed to tell my second wife also before we became married.

The problem became with my second wife was when I though I was telling her my gender truth about being a cross dresser, I wasn't. All along I was lying to myself and I was really transgender, not a cross dresser. Which was always a major problem for my second wife. She didn't care about the cross dressing but drew her line in the gender sand when it came to any idea or discussion of beginning any gender affirming hormones. Which, had she lived, would have probably ended our relationship.

Years later, at the age of sixty, I thought I was done with anymore serious relationships and wives is when several other friends came along, including my current wife Liz. With them, I basically had the opportunity to go full circle with my gender truth. Specifically, with Liz who told me at the time, why didn't I just leave the rest of my male life behind because she didn't see any man in me at all. 

Her push was all I needed to throw out what was left of my male clothes and concentrate on living my gender truth. The only problem I had with how it all worked out is why I waited so long to see it and live my gender truth. 

Wednesday, February 21, 2024

Writing Euphoria

Image from the Jessie Hart

Every now and then I receive a comment which brings all the effort I put into writing a daily transgender blog into focus. 

When I started writing this blog over ten years ago, I set out to hopefully help anyone else with gender issues similar to mine. Back in those days, when I revisited my old blog posts, I mainly see an over riding interest with my feminine appearance and not much else. Of course when I transitioned into a fulltime life as a transgender woman, I discovered all the other challenges I was going to face. It was all much different than my life as a casual cross dresser. 

This is where the writer's euphoria comes in. I recently received this comment from Jennifer " Thank you for publishing your thoughts and experiences. I am an older, but not that wiser, transgender woman just starting out on the road to femininity. Your blog helps me much to understand the hurtles I am about to encounter. Thank you for sharing your thoughts and opening up to your experiences.

Thank you, Jennifer" You are welcome Jennifer and thanks for sharing such a wonderful comment. 

Somehow, along the way, the blog made it's own transition into looking at my life as a senior transgender woman. I found, being "more mature" in many ways had it's advantages. Primarily when it came to beginning gender affirming hormones. Because at my age, my testosterone level was already in a decline, the rush of new estrogen in my system seemed to be more natural. On the other hand of course, I needed to go through the medical screening process to determine if I was healthy enough to proceed on the program I was prescribed

As far as being "older but not wiser", I think I faced that aspect of my life also more than I could ever write about. For better or for worse, I had already went past and missed my formative feminine years and needed to master the mysteries of makeup and fashion on my own. There were no teen girls to critique my look and for me to return the favor. Plus, I spent way to much time alone with no girlfriends to shop at the mall with. 

I discovered too, there was a small niche of older transgender women who had lived through the dark and lonely pre-internet years. I am amazed how many readers still remember fondly the "Transvestia" publication along with Virginia Prince. But then again, it was all we had to provide any sort of light in our gender closets. 

These days, I am still committed to attempting to provide any guidance I can to anyone like Jennifer who needs it. After all, our gender journeys through life on one hand are so similar but on the other not so much. Each of us needs to navigate how we are going to shed a life of living male and begin all over again. And just when we think we have it made, we need to face the reality of being trans in retirement communities and/or assisted living. Regardless of all the negative publicity we receive from politicians, I still believe more people such as the "Alzheimer's Association" are researching ways to be more inclusive to the LGBTQ community. So, there is hope. 

Thanks again Jennifer, Jen (another reader) and all the others of you who join in with me here on the blog. You give me writers euphoria and improve my mental health.

Wednesday, February 14, 2024

Beautiful...Inisde and Out


Image from the Jessie Hart 

As I obsessed with looking the best I could as a novice transgender woman or cross dresser, all I could think of was how I looked. Little did I know there was so much more coming up in my journey to living fulltime as a trans woman. I needed to live my looks as well as just admiring myself in a mirror. 

This morning turned out to be a prime example. Today I tagged along with my wife Liz to her mammogram appointment. Before I went, I applied my usual minimal amount of makeup, brushed out my hair and was essentially ready to go. While I was doing it, I felt it was time for a change. I thought I have been in a rut I have been in too long. I have essentially stopped working on my appearance and then being shocked when I am mis-gendered. 

Of course, nothing negative happened morning when it came to the doctors appointment because there were very few people waiting to begin with plus no one was paying any attention to anyone else. Since I had a spare moment, I went shopping on my phone for a foundation specifically tailored for older women. A group I naturally fit into. I found their on-line site and decided to give it a try. 

Currently, I am relying on the skin effects of gender affirming hormones, so I don't have to use a foundation at all. Or so I thought. It's occurring to me now the hormones have been a crutch for me to quit trying as much as I did. I ordered the new foundation and I will let you know my feelings. 

The end result is I need to work harder to make my inside and outside match up again. I learned long ago, similar to many cis-women, I will never be the prettiest woman in the room. I needed to find other ways to survive in the world as a new transgender woman. Little did I know, my biggest positive as a new person was already within me. My discovery was my inner feminine soul was actually good people. Opening up to others turned out to be one of my biggest pluses. The world turned out to like me. 

Doing my best to be beautiful to others, inside and out, turned out to be one of the most beneficial things I have ever done. Now, I feel it's time to get out of my rut, have some fun and get back in the game. Maybe to the point of treating Liz out to get our nails done and then have some dinner out at our favorite restaurant

I need to get us both out of the house.  

Sunday, January 14, 2024

Supporting Casts

 Recently I wrote a post concerning (among other things) the power of having cis-gender women friends to help your transgender transition along at key times. If you are similar to me, you started your gender journey in the mirror and dreamed of the day when I could enlist another more experienced woman's aid with my wardrobe and makeup. 

In response, I received this comment from "Anonymous" : " It’s nice to see the positive side, the genuine sense of joy in transition. I know I have felt euphoria as I have gained the confidence to comfortably present myself authentically to the outside world. It’s interesting that you mention feeling more comfortable in the company of women. That has been my experience. I am not attracted to men physically. Frankly, I prefer women as friends or if given the opportunity, as intimate partners." 

Thanks for the comment! 

For some reason, during my life I have always felt more comfortable around women, even though there were very few girls in the neighborhood I grew up in. In order to survive, I needed to develop strong masculine tendencies to basically keep the bullies away. Even though I was successful, I still for whatever reason, never really had many close male friends Maybe, it was a result of my inner feminine self. Or an overreaction to thinking I maybe gay. My own inner form of homophobia. In later years I wondered if the fear of my own sexuality would carry over into my own inner transphobia. Essentially when I feared what would happen if I went too far into living as a fulltime transgender woman. 

In passing the other day, I mentioned certain early cross dressers or transvestites' who were seemingly using cigars to back up their reliance on so called male stereotypes. to which I received this partial comment from Georgette who happens to still smoke cigars, even though she has transitioned:

" Why do so many people break everything down to a Masculine or Feminine thing, I get a laugh or no response from many part-time CD/TV that will say that they still enjoy all those "Manly" things, I started smoking cigars in my teen years and still do. It is a world of difference from smoking in general."

Thanks to you Georgette  for the comment!  I think too many people over-simplify the masculine and feminine thing. Including me. Sometimes I get lazy when I write and get ahead of myself. On the other hand, describing the differences between the two main binary genders becomes very tedious for me. As far as cigars go, they were part of my life when I needed to out macho another man, or at least connect with him. Before I transitioned and grew away from them, a good cigar was a priority of me so I understand where Georgette is coming from in her comment. 

As far as comments go, I always invite any of you to participate in the blog by commenting and I will try to add in your input when I can, Sometimes it is applicable, sometimes not. The same way I felt I couldn't use the makeup advice I was given very early on when I was a novice crossdresser. If the truth be known, I probably had more experience with makeup than some of the women I was with. Later on was when I discovered how much I could learn from the women around me about really being women. As Georgette said going much farther than simply breaking down life to a masculine versus feminine existence. 

It took me awhile to finally learn my second wife was trying to tell me the same thing when she said I made a terrible woman. Perhaps my problem was I was making a terrible person to begin with. It took the emergence of my inner female to recognize the difference with the help of a strong supporting cast.  

Wednesday, November 29, 2023

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. 

Sunday, October 15, 2023

Always on Stage

Image from
the Jessie
Hart Archives

Very early on I learned when I entered the world as a novice cross dresser, I was always on stage. 

More precisely, not only were men judging me, I also needed to worry about other women. Even more so than men as it turned out. As women in particular had the tendency to be more picky than anyone else because they had been through the process of appearing in public. Women know all of the intricacies of fashion and makeup. Even if they decide to follow the rules or not. At the least, genetic or cis-women don't have to follow the rules when they go out in public. 

How this all translates to transgender women is, we all have to try harder than the average woman just to get by in the world. Not only do we have to blend in with the women of the world in general, we have to do it better. My biggest mistake was when I began to transition, I was still mainly interested to pleasing men which eventually led me to try to dress sexy. Which eventually turned out to be trashy for me. The entire process for me led to me creating too much negative attention that resulted in embarrassing situations. I was trying to fit my testosterone poisoned male body into teen girl fashions, which in no way worked. 

Finally I learned the hard way to blend in but with an edge. By an edge I mean I still had to work hard on my feminine image. I needed to out do other women but not look like I was trying. To work towards accomplishing my task, I had to perfect an understated fashion look. What were other women wearing and how could I come close. Not to mention the makeup I chose for where I was going. 

Since I was always on stage, I became used to it. I became secure enough not to retreat when I was approached mainly by other cis-women. I kept my cool and was able to learn from them. How did they handle the world around them. Specifically their interaction with other men. It turned out, for whatever reason, I never was able to have much interaction with men to worry about. As I said, women were a different matter. Other women often were able to start a conversation with me by complementing me on an accessory such as my ear-rings. probably because most were just curious why I wanted to be in their feminine world. Through it all, I found overall acceptance and was able to slowly perfect my on stage presence. So much so, I began to feel natural doing it.

Feeling natural soon became a primary goal for me. As my old unwanted male self began to slip away, I felt better and better about myself. 

Even though being on stage was very un-nerving for me in the beginning, I became used to it as a normal way of life for all women in the world. Both men and other women were always looking at me. Once I got used to it, life became so much easier to survive as a transgender woman in the world.

Tuesday, July 18, 2023

It's an Art Form

Image from Hung Pham
on UnSplash

I don't think any transgender woman's path to her own womanhood should be taken lightly. 

We take many many years of experimentation before we reach a point where we can even venture out in the public's eye without the fear of being made fun of, or worse. The problem is even those born female don't have an easy path towards making it to woman hood. Another problem trans women have which extends far past what cis-women face is we don't have any real mentors to help us with basics such as makeup and wardrobe. In most cases, we have to sit back and let testosterone ravage our bodies with unwanted male changes. By the time we can start hormone replacement therapy later in life, it is too late. 

Also, as soon as we discover the art form of makeup and wardrobe, we also are faced with how to more completely present our new feminine selves to the world. I remember my very early days when I went to transvestite mixers up in Cleveland, Ohio as well as in nearby Columbus, Ohio. I found quite the layers of different people attending, all the way from those still dressed as their male self to those impossibly feminine women who I called the "A" Listers. Even though the "A's" had been able to conquer the appearance part of being feminine, on closer inspection, it seemed they had a long way to go to capture the art form of having any class at all. In fact, I nearly changed my terminology from "A" Listers to "Mean Girls." Maybe I was being too subjective myself because maybe they were just going through a phase in life of their own. 

You need to keep in mind too, how many cis (or genetic) females you know who never made it to the position of being true women. The same can be said for males who have never understood what it takes to be a real man. Or, to be able to put the toxic male ego aside and treat the world better. And, when you are obsessed with presenting as a woman, think of all those cis-women who struggle daily with it also.

No matter how you choose to look at it, following your new gender path is an art form. A woman often glides when she walks in that uniquely feminine way and putting your old male movements in motion is a challenge. Let's not forget too, the aspect of communication. There are certain smiles which women reserve for other women as well as a set of passive aggressive or non verbal communication. Consider how many times when you were cross dressing as a man and couldn't quite figure out what a woman was trying to tell you. It is just as bad until you learn the basics of communicating with another woman as your transgender self. If you think you have conquered the makeup and wardrobe artforms, just wait until you get to the level of communicating with the world. With women and men.

If you want a challenge like no other, try changing your gender. Discovering art form after art form makes the process the least. 

Monday, November 8, 2021

The Magic of Makeup

 Most certainly one of the most bewildering ,yet on occasion fun part in a transgender woman's transition is making yourself up. Of course, very early in the transition game, the importance of attempting to align your external source with your authentic self becomes very important. 

I remember back to the earliest days of rummaging through my Mom's makeup drawer and "borrowing" certain items I had seen her use such as lipstick and eye shadow. The challenge always was to use the items and put them back so well she would never notice. She never mentioned it, so perhaps I was careful enough to get by. 

All of this took place during the 1950's and I lived in a rural area where I was able to deliver news papers for extra money. I saved my paper route money and combined it with the small allowance I received for doing chores around the house and actually had enough money saved to purchase my own makeup. Having the money was one thing but finding a place to spend it and buy makeup was another.

Those days were way before the advent of any makeup specialty stores. The closest I could afford and find away in town to go to were a couple of the old "five and dimes" department stores. They featured a small selection of many items (including makeup) a lunch counter as well as other items. I was even able to find me a pair of women's shoes I cherished on one of my shopping excursions. 

Another problem I encountered was how was I going to get to the stores I wanted to shop at plus once I was there, having the courage to actually go in and search for makeup. I was able to overcome the transportation issue by spending the night at my grandma's house. She lived very close to downtown where the stores were located. I could walk and pick out my hard earned treasures. 

As I wrote, I vividly remember the fear or out right panic I felt the first time I gathered the courage to go in the store and shop. I ended up feeling very relieved when I finally reached the makeup section...until I saw the selections which were available. I thought, now what? My plan had been to briskly walk in, pick out a couple makeup items, head back to the checkout counter and leave. My plans did not include a lengthy stay to shop. 

Through it all, I stayed the course and purchased a couple of items. I was certain the whole world was staring at me but they weren't. I survived the checkout counter and headed back to my grandma's.

Little did I know  from my humble beginnings at the makeup counter, I would have many more occasions to feel nervous. Over the years I would have much more error than trial when it came to applying my own makeup. Finally the internet came along and I was able to study makeup tutorials and improve my craft. 

Ironically I became so skilled my two wives (who wore very little makeup) would come to me for advice when they wanted to dress up. 

When I became very serious about transitioning was when I attempted to take my makeup to another level,. During this period I was desperately trying to blend in with the professional woman and proper makeup was a necessity. 

These days I have basically gone full circle with my makeup. Thanks to the results of hormone replacement therapy and age, my skin has softened and the angles of my face have rounded, Naturally, I need less makeup when we go out although I still wear more than Liz. Since Liz is a former "Avon" makeup sales person, she still retains a knowledge of the artform.

She has been threatening to do a makeup job on both of us before we go out. I can't wait for her to work her magic. 

Wednesday, July 17, 2013

All The Makeup Mistakes I Have Made!

I picked this video for the Cyrsti's Condo big screen because this person someone captured all the make up mistakes I have made in two minutes!

Wednesday, May 8, 2013

"Borrowing my Face"

Sunday a friend of mine contacted me and asked if I would be interested in lending my face to a friend of his who recently became a Mary Kay Cosmetic person.

At first I thought "is he trying to tell me something?"  (just kidding) the first thing I thought was "sure why not?" If I ever reach a point with my makeup that I can't improve or look for advice, then I'm doomed to mediocrity...or worse.

When the consultant and I touched base the first phrase she texted was "can I borrow your face?" I said sure for what it's worth and if I can have it back to keep using. It's all I have!

Seriously, I feel I feel as if I'm in a makeup "rut" of sorts and any input is good input.

I'm going tomorrow (Thursday)  so I will let you know how the process goes and if I got my face back!

Sunday, June 17, 2012

1951 Women's Total Beauty Guide

Years ago I was working on finishing my own "girl" room complete with period feminine classics.
One of the classics I came across was this 2 manual "The Charming Woman" series.
For those of us who are into classic beauty and how to achieve it - these are 400 pages of everything you need to know.
Etiquette, makeup, hair, exercise, fashion and so much more!!!
They are binded together in "Art Deco" style books.
I have listed them for sale in one of my "Etsy" shoppes for 22.99 (not including postage.) You should be able to access it here.
The piece was published in 1951 an era when being female did not make you a woman!

Sink or Swim

Image from Trans Wellness Event.  Jessie Hart Archives.  Many times when I first entered the world as a new cross dresser or femininized mal...