Blind Date

As you make the Mtf Gender Transition, there are certain milestones you must pass as your male self slips away. As it turns out, your male self often fights harder to give up his privilege than others.  I ry remember vividly a few of those moments as I transitioned. 

As often happens, my memory was jogged by reading someone else’s  post on the topic. This time it was another by Emma Holiday who I read on the “Medium” format which has been difficult to link to because it is a paid format. Regardless, Emma’s post was called “A Blind Date with my Trans Identity.” In it she details her first trip to a feminine make over artist and her feelings after the experience.

It turns out I had a similar experience years ago which started my slide towards living full time as my authentic transgender self. 

As I said, this happened years ago when I went to a transvestite “mixer” in nearby Columbus, Ohio.  The evening included a chance at having a professional makeover, if you were brave enough to do it. Finally, after agonizing I decided to hitch up my big girl panties and go for it. Of course the first problem was having to remove my wig and existing makeup.

To make a long story short, the makeup up artist was a guy and he did a fabulous job! It was the first time I had seen the real girl me staring back at me from a mirror. Deep down, somehow I knew I could never go home again to being my routine guy self again. Then it was reinforced by a guy approaching me in a venue some of us went to later in the evening.

I had experienced the first of many blind dates with my transgender self.

However, my male self would never go easily and fought totally against my feminine self. Even to the point of him wanting to show himself to a couple cis women I knew who totally were accepting me as a transgender woman. 

Finally it took my relationship with my partner Liz to completely accept my natural self. 

The last gasp took years to get to. Thanks Emma for the memories. 

Emma Holiday

A Positive Step?

 Recently, I have been reading about and even know a couple people who describe themselves as non binary humans. It’s my guess most of them would also be known as gender fluid or even androgynous back in the day. 

Then again, I don’t like to become mired in labels. Plus, as Connie has brought up in a few of her comments about how years ago, there were only two recognized genders. Then as the years progressed the transgender term became a reality. I remember the first times I became aware of the idea of a transgender person, the more it made sense to me.

All of the sudden, the impossibly feminine cross dressers I encountered at the very early transvestite mixers I attended made sense. They weren’t cross dressers at all but rather, they were transgender. While we are on the topic of labels, a few of them even made the jump to transsexual and went all the way to sex change surgery. As it was known as then. 

Now, I personally have gone way past the idea of operating outside of the gender binary. I am firmly in the transgender camp and have no desire to vary my existence at all back to any aspect of my previous male life. 

On the other hand, I am fascinated by those who aren’t and are able to be gender fluid or non binary. Hopefully, all of it represents a step forward for humans everywhere.  

In the meantime, here is the transgender flag. (I think) Because these days, everything changes so quickly in the world of gender.

Men in my Life…Sort of

As I was writing another chapter in my book called the “Men in my Life”, I happened to remember this experience which happened years ago to my wife and I in a small tavern in Cleveland, Ohio. As I recall, we were just trying to waste a bit of time creatively (by having a drink) before we were going to a transvestite mixer that night. 


As we sat at the bar, a guy on a big Harley motorcycle rode up outside and ended up sitting next to the two of us at the bar. Fortunately (I thought) for me he took the seat next to my wife and began to talk to her. I was desperately shy and insecure about myself since I was so new to going out in public as a woman at all.  I also at that time hadn’t absorbed much of the interaction of the genders’ from the women’s viewpoint.
As time went on, my wife and this guy were talking more and more and for a second I wondered what I could do if she decided to take off for a ride with this guy on his motorcycle. The answer was simple. I could do next to nothing except wait for her to come back. 


Probably, the worse part about the entire situation was both my wife and I knew she was totally in control of the whole thing. 


After leaving me to worry about what was going to happen for an appropriate amount of time, in her mind, she excused herself from the guy and we went on on way. 


From the whole experience I learned the hard way I needed to improve my feminine appearance quickly so I could compete more completely if a single guy ever approached my wife and I again. I wanted a fighting chance not to be ignored.  

Happy Mother’s Day

Or should I say, “Happy parental unit day?” That’s what my daughter calls me. 


This is my usual Mother’s Day post. My mom was a 5’2″ head strong dynamo of a person and not one I ever thought would be accepting of having a daughter instead of a son. My only “coming out” moment with her didn’t come until I was well into my twenties and was just honorably discharged from the Army. One night when I was coming home after partying all night with my friends, I came home and found her waiting up for me. I was operating under the power of intoxication and somehow the topic came up (I don’t remember how) and I told her I was a “transvestite.” She didn’t miss a beat and said she would pay for electrode shock therapy to help relieve myself of my “problem.” I quickly told her, I didn’t have a problem and no, she wasn’t paying for anyone to hook me up to a wall socket. Ironically, that turned out to be the only time the subject was ever brought up again. She has since passed on many years ago. 


For years, I resented her reaction to my coming out declaration. Then, I began to consider her life as part of the “Greatest Generation.” I realized her offer of help was just that. Help for a perceived problem she thought I had. No more and no less. 
When the time came to legally change my name, my daughter and I got together to come up with a name which would be easy for her three kids to respond to. At the same time, I began to think of family names which might work. Finally, I decided to honor my Mom by accepting her name as my middle name. 


Perhaps now, she would be more accepting of having a daughter instead of a son.


Happy “Parental Unit Day” to you all!

No, I Can’t Help

This comment comes from Calie and goes back to the recent post concerning internalized transphobia. It’s a great comment and indirectly happened to me too:


“I assume we’re talking transphobia within the trans community.

I helped a very close friend through her transition, from when she was a “he” to the completion of her many surgeries and well into her new life. Throughout her transition, she was very active in our local trans organization but all of that came to an end once she had fully transitioned and started a completely new life and job. She vowed to stay away from the trans community and has continued for many years now to have nothing to do with it. I sort of get that.

What just killed me and pretty much killed our friendship was a question I asked her when she had separated herself from the trans community. From my pre-teens, I have always felt I should transition. For many complicated reasons, I never did. There was a time, following her transition that I was very, very close to making the decision to go forward. I asked her if she would stand by me, as I did during her transition…going out with me, coaching me, helping me with mannerisms, voice, etc……all of the things I helped her with. With no hesitation at all, she said no. She felt that associating with someone who clearly would not pass, at least in the beginning, would result in her being clocked. OK, I get it, but I was deeply hurt and we now speak to each other perhaps once a year.”


Thanks for the comment!  I imagine you were hurt! So sorry. 


I had a close acquaintance I saw on a fairly regular basis until she went through the genital realignment surgery. She was always very presentable as a cross dresser and/or a transvestite back in those days, so in many ways I considered her a muse. Even though she didn’t indicate she wanted to break off all interaction with me after her operation, I assumed she would want too. After all I was a mere questioning cross dresser back in those days. Perhaps she would have had enough wisdom to tell me moving forward to GRS was not a matter of looks. It was a matter of how you felt. 


I am sorry now I assumed she never wanted to see me again. 

Body Image and the Trans Girl

As I continue to write bits and pieces in my book, the topic of body image keeps coming up. As referenced in yesterdays Cyrsti’s Condo post, cis women often have the same problems with feeling secure in their own skins as we transgender women. 

Through the years we have to struggle through the dazzling yet scary arrays of makeup and fashion to desperately try to find our spot on the world. The ancient stereotype of the cross dresser squeezed into a mini skirt and heels waltzing through a mall somewhere is my scariest vision and one I am afraid I tried too. Fortunately, there are no pictures :). 

Then there is/was makeup to contend with. In the looking like a clown department, I was lucky I had quite a few chances to experiment when I was younger with makeup…even to the point of convincing my first fiance to apply it for me.  As far as my body image was concerned though, I didn’t really have one, except an unrealistic view of how I thought I should look. Again and again, the wrong use of mini skirts did me no favors. I was over reacting to the rare occasions people saw me in a short skirt and saying I had good legs. The problem was I had no idea of how to properly showcase a feminine asset. In fact, I went the opposite direction.

In the 1970’s I became enamored with the hippie boho look, complete with bell bottom jeans etc. So, I began to try to dress myself in those fashion directions (which I still like to this day). In fact, I used to get asked at the transvestite mixers I went to how I could not possibly wear a dress. During that time I was slowly beginning to discover my inner woman’s body image I have today.

I still rarely wear dresses or skirts. Relying instead on leggings and sweaters during the cold seasons and lightweight culottes with tank tops in the summer. I do have a couple maxi dresses for the hottest days. 

The fun part is, women can be different and that is OK…to a point. The hard part still is getting to a point where your inner woman tells you what she wants to be. 

These days though, there are getting to be numerous places one can go to for help with your body image. Take Ginger Burr’s Total Image Consultants for example. Leann wrote in and said Ginger runs a very trans woman friendly business. Plus around here (Cincinnati) there are a couple of the big specialty makeup stores which are more than happy to help a novice with her makeup needs. 

Look, I know the vast majority of us will always struggle with the testosterone poisoning we went through or still going through. On the other hand, options are becoming more accessible to help with your body image problems as you attempt to sync up your internal and external selves. 

Terrible Woman

This post is very much a continuation of yesterday’s Cyrsti’s Condo post on trans woman intuition. We have quite the chance to develop an amazing gender intuition because we live on both sides of the gender frontier. 

Years ago, when I was exploring jumping genders my deceased wife and I became embroiled in a huge fight over how much I wanted to cross dress. Basically, it wasn’t how much I wanted to do it, it was where. Once I had started to venture out of the house, the more I wanted to. In fact, I was still on a huge ego roll from the night two women tried to keep me out of a transvestite mixer. They thought I was a “real” woman. 

During the fight, my wife shot me down by telling me I would make a terrible woman. I told her how could that be after my encounter recently? She promptly told me my appearance was not what she was talking about and I had just made her point. Being a woman was indeed so much more than looking like one. 

From that point on, I set out to find out what she was telling me. I did my best to develop my own idea of what women went through as they lived their lives. You might say I was learning my own version of trans woman intuition. It wasn’t easy though as I had a strong male ego to work away from. 

After all these years, I can’t tell you I am where I want to be in life. To be more spiritual and intuitive may make me a more stereotypical feminine person but it also makes me a better human too.

I am far from getting to my goals. Then again when I arrive I probably will have crossed over to the other side.

Hopefully then, I won’t be considered a “terrible woman,”

What’s Next?

Seemingly, the more I think about my past, the more I consider the future. Realistically speaking, most of my life lies behind me and I have written many times here in Cyrsti;s Condo concerning my fear of being “cared” for in a nursing home with a very transphobic staff. Hopefully society will continue to inch forward in it’s knowledge and support of transgender women and men. 

Then quickly my mind returns to thinking about my past experiences I can put in the book. Many are buried deeply in my mind to a point where I can barely remember them.

Currently, I am writing about the very few men in my life including the first one. My meeting with him was brief and happened the night of my first professional make over at one of the transvestite mixers I went to. I guess I could say I had interactions with two guys that night since the make up expert who worked his magic on me was the first. Indirectly leading to the second. 

During these mixers, I loosely tagged along with the “A” crowd or as I also called them, “The Mean Girls.”  Approximately five or six of them always formed a clique which very few others were ever welcomed into. It turned out on that magical night, not even did I tag along, I crashed the clique. 

Perhaps you noticed I said “crashed” and not joined. No matter how popular I became for one night, there was no way I ever wanted to become a permanent part of their exclusive group. 

Now, back to the evening.  As I said, the make up expert did a wonderful job on me and even I was amazed. It was my first experience with someone else (who knew what they were doing) doing my makeup.

As I have written about before, the clique of the most attractive cross dressers or transgender women (before there was such a word) went out to party at gay venues after the mixer. Early in the evening I had the usual unremarkable time tagging along. It was later on when I was approached by a guy in the last venue we went to. He asked me to stay and he would by me a drink. Since I was dependent on the clique to get me back to the hotel, I declined.

More importantly though, the clique was dazzled I was approached and none of them were. 

Sadly, the next day I had to go back to my usual male boring existence.

Are There More Trans People?

Sometimes it seems to me there are more transgender women and men these days. 

I back up my theory with two reasons. The first is due to the impact of social media and the internet. I still am amazed about the amount of material I run into as I research possible blog topics. Of course, at my age, I go way back to the days of Virginia Prince and her Transvestia Magazine being nearly the only sources of information for novice transvestites. Now of course, there are nearly too many outlets to mention where you can find information on trans people,  

Janet Mock (below)

As an example, I just Googled “transgender” and received 173 million results. One of which one of the top trans activists Janet Mock. Indeed we have come along way!

Another example I can use is Angela Ponce who we featured a couple days ago here in Cyrsti’s Condo.  She competed in Miss Universe in 2018 as Miss Spain. I can only imagine some of the feminine back stabbing going on behind the scenes with such a gorgeous contestant competing who was also transgender.

My second reason is an extension of the first. Overall, we are so much more visible because we all have a better idea we are not alone. Plus, as we have pointed out in the blog, it is increasingly easier to carve yourself out a place in the world.

So, there are probably not more transgender people in the world. Just more who are visibly finding their way.  No longer do we have to worry about transitioning and disappearing. 

None of this though takes anything away from how difficult a gender transition can be. Let’s not forget how gender dysphoria can tear away at a soul and how the whole process of learning another gender can tear relationships (family) and employment apart.   

Maybe, just maybe, if there are more trans people, they can have a chance to be happier.

Halloween Dreams

It amazes me after all these years I can still have so many vivid memories of my early Halloween experiences.

One of the earliest goes back to the 1980’s when I lived near Yonkers, New York. I was working for a Wendy’s franchisee then and one of my assistant managers invited me to a Halloween get together she was having. I saw it as the perfect opportunity to get out and live as a woman for a short period of time…if I could figure out how to do it. 

Since my wife wasn’t really into Halloween and knew why I was, it was fairly easy to convince her not to go. Plus, she was always against what she thought were my sleezy costumes. With her out of the way, I was free to costume myself anyway I pleased.

I picked out a short mini dress, heels and one of my fave wigs for the evening. If you remember, big hair was “in” in the 80’s, so I fit right in. After freshly shaving my legs, applying my makeup, panty hose and getting dressed, it was time to go.

What I wasn’t prepared for was how well I was going to fit right in. 

It turned out, the Halloween “party” she invited me to was actually a group of her girl friends who all were going to one of their local taverns to party. I was in heaven when I saw all these women dressed almost like I was. Initially they were in shock when they saw me and looked me over head to toe until my friend told them who I was. Then I was accepted. 

The tavern was within walking distance of her house, so here we were all in our heels clicking along as we walked to the party. Again, I blended right in and felt great. 

Once we arrived at the tavern, we proceeded to order drinks and the other women got up to dance. Unfortunately I have exactly no rhythm and kept my seat. Inwardly though, I was savoring every moment and even got asked to dance. Again, I politely declined. 

All too quickly the evening had to end and I had to head back to my routine existence. However, the word spread through out my store how I had dressed for Halloween. Nothing much happened as I just said I always wanted to do it. Resulting in a few “yeah right” smiles.

Little did I know how long the memories of the evening would linger. It showed me how it would be to interact with women on their own level. If only for one evening.