My Last Date...as A Man

 

Long Dark Haired Wig Look
From the Jessie Hart 
Archives.

In many ways this was the final straw in my attempt to live in a male world. Approximately two years following the passing of my wife, I had the opportunity to date the Mother of one of my servers. She was smart, single ( near my age ) and very attractive. If I was a "real" man, she was the ideal woman I had ever wanted. As always, I realized nothing had really changed with my gender issues when it came to dating other women. Still I went ahead and tried and succeeded on setting up a few dates.

Along the way, we went on dates to places such as the Frank Lloyd Wright designed home in Springfield, Ohio all the way to a company sponsored suite at a Cincinnati Reds professional baseball game. Seemingly we were moving along at an reasonable rate until she sprung the question on me which probably ended it all. She asked me what my deceased wife would say about the situation I was in life without her.  I fired off the answer I drove her to an early grave without thinking of the consequences. Even though essentially I told the truth, I didn't immediately realize my future days with her were numbered. Obviously I decided not to mention any of my gender issues as probably added to the extreme stress of my wife's life.  

Through it all, my daughter had monitored my return to the dating field with some interest and at that time I hadn't come out to her as a transgender woman yet. As a gift she gave me two tickets to the late Joe Cocker who was performing at a nearby outdoor venue. I immediately took the opportunity to invite my new friend to join me. Initially she said yes and I thought all was good. Then about three or four days later she abruptly called me and said she wanted to end all dealings with me. I was shocked and said goodbye forever. Then I had to decide who I would invite to go with me to the concert.. Fairly quickly i decided I only knew one other woman well enough to invite and that was me. It was a great opportunity to judge how well I could present in a totally different situation. 

First I had to come up with a proper wardrobe choice which would blend in with a probable slightly upscale audience. For the evening I chose my black slinky wide legged slacks along with a black sleeveless top. The outfit was one of the benefits of having nearly hairless arms. By this time, I had arrived at a point where I didn't have to worry anymore what people may think of me for having hairless arms when I was still presenting as a man. For the evening I selected my long black straight haired wig to go with comfortable flats and sensible makeup to fit in. 

To my knowledge, all went well during the concert. Nobody gave me an extra glance and I was able to enjoy a cocktail as well as the concert. I ended up being one of the better dates I had ever had. A fitting end to my often discouraging history of my dating as a man. Something it turned out I never wanted to do anyway.  

When I transitioned to a transgender woman and was dating women such as my future wife Liz, I relaxed and was finally able to enjoy a new and wonderful life. The entire process was similar to everything else I had discovered about myself. Living a gender lie was never easy or successful, My last date as a man just proved it again.

Pride in January?

 Pride month for the LGBT community should be a year around celebration.  Once you reach the certain point of your life when you are comfortable as your authentic gender self, it's time to celebrate yourself.  In other words the tipping point of having total confidence in yourself. Confidence of course was the topic of a recent blog post which Paula commented on:

" Confidence is key. It took me a while to inhabit the world confidently as a woman of mature years. We missed out on a lot of the learning process, we had to compress so much into such a short time. But now, I find that I have the confidence to do things I would not have before, because I am not just confident in my femininity, but in myself. " 

As always Paula,  thanks for the relevant comment.

Pride can be expressed in many different ways. You don't have to go watch garishly dressed drag queens strut around in heels to participate in Pride. 

You can dress in your favorite jeans or leggings depending on the season or you can be the occasional cross dresser in your local bar.  The important part is you are living your life as you feel natural doing.

I know also, many of you think you are impossibly stuck in your transgender/cross dresser closet and will never escape. There was a time when I felt that too. I was just able somehow escape the tragic situation I was in and sheer destiny led me out of my closet and into a feminine world. 

I will say though I had to work very hard to put myself in a position for destiny to find me. I searched high and low on dating sites looking for someone. Either male or female to spend social time with and was a miserable failure. My Pride comes from  from finally being persistent enough to find friends such as Kim and Nikki who I met in sports bar venues and had a great time. All the while I was learning valuable lessons on how to navigate a feminine world. Then there was Liz who responded to a online dating site, saying I had sad eyes.

Along the way, being a partier didn't hurt me when I did attend various Pride events as you can see in the second picture which was taken in a very busy gay venue in downtown Cincinnati several years ago. 

To make a long story/post short, have Pride in your journey. Even though it may consist of being able to exist in a very dark closet.

You deserve it.

 

Need a Date?

Unfortunately, too many transgender women are very lonely and can't find any stable social contacts. Either with women or men. Back in the day, I went through the same dilemma. At the same time I was going out to venues to seemingly entertain myself, I searched many on line dating sites at the same time. Needless to say, I sifted through a lot of trash until my partner Liz found me. What I mean is, she answered my ad on the Zoosk dating site. That was nearly nine years ago and we have been together ever since. Perhaps I was fortunate in that I was fairly unsure about where my sexuality would take me, so I could double my search to both men and women. 

Back then, there weren't any real dating sites which dealt with transgender women and men. Most all were fetish sites mostly populated by male admirers of trans women. I had the misfortune in my dealings with admirers. One corned me in a hallway once during a party and one wanted to just wear my panties. I won't even mention the number of times I was stood up or "ghosted" by men.

Today though, a new transgender dating site has been announced which promises to be different.  I don't like the name but here is the info:

TransFable, a brand-new dating app for men and transgender women, is set to take over the digital world of transgender dating this year. The first transgender dating app of its kind, TransFable offers users a safe and secure platform to meet their match, where transgender women can connect with genuine men for free.

TransFable stands apart from its competitors as a transgender dating app specifically designed for those seeking serious and genuine relationships. It can be a challenge for both men and transgender women to meaningfully connect with one another and TransFable offers the perfect place to do so. Indeed, if you are looking for a hook-up, this is probably not the transgender dating app for you. However, if you are serious about finding a genuine match, then TransFable is the transgender dating app to be on in 2021.

All users on TransFable are manually verified by a human so you can be rest assured that you will not match with any bots or fake profiles. 

Sex is Power?

 Recently here in Cyrsti's Condo I wrote a post about the idea of why women (cis or trans) scare men so much. Essentially it is because sex is power and to many men, women hold most all of the power. After all, women are often stuck with raising children if unplanned pregnancy's occur. Along the way too, men end up perceiving women as possessions. 

Many women (again cis or transgender) eye being with a man as a validation of their femininity. I was guilty of that also when I started to date after coming out as transgender. Plus I thought if I could find a man to be with, I could present better as a woman in public. Ironically, my brief flirtation with men didn't last long after I found I was experiencing much more attention from women.

But through it all, I found sex was power as I pursued companionship with men on the newer dating sites which were springing up on that new found contraption called the internet. I don't want to remember how many times men were willing to flirt with me on line and just as willing to stand me up in person. After seemingly hundreds of contacts, I did experience several dates with above average men...including a couple way above. Including a transgender man. 

During it all, I was always acutely aware I was different and yet I was still able to sense the strong sexual attraction rarely between men and I and seemingly always with the women who were intrigued by me. So, sex was power.

Actually this whole post came about from this comment from Michelle:

"I have to agree with you about ego vs need to feel wanted. As for the complexity of the subject, it's somewhat simple in the way, women need to feel the emotions of wants and needs. We give ourselves freely in order to secure those emotions, with the hope that a man can live up to the responsibilities of providing the security. We need to understand that it isn't just for a one night stand but a long term commitment.

As for the sex drive portion, in today's society, it's because of several factors. One is that women have learned from our male counterparts that sex can be used to secure power. It can be used for both aggression as well as passiveness. The second factor is that we have been inundated, since the 60's, with people telling us that sex is the pleasure we need to maintain our sanity. In a way they are right since a woman's body does need that kick of hormones that sex gives us to help maintain a healthy body."

Thanks Michelle! One of these days we will have to examine the role high heels play in the gender power struggle. 

On Line Action?

Recently here in Cyrsti's Condo, we have slightly covered the subject of on line dating sites and their availability to transgender women or men. In fact, over the years many have become nothing more than glorified porno sites attracting "admirers" of trans women and/or cross dressers.I have another experience which goes back to the very earliest days of on line chat rooms. But first, here is an experience from Connie:

"Maybe I shouldn't admit this publicly, especially just two weeks away from a 49th anniversary, but I dabbled in dating sites a number of years ago. I labeled myself "woman 'curious' about women," and I never mentioned that I was trans. I did say that I was married, although I was careful to always say "spouse" and never used a pronoun. I was not interested in finding a relationship; I just wanted to see if I could be seen as a woman (or be seen as attractive by another woman). I don't think the term "catfishing" had even been coined yet, but I guess I was sort of doing it. I'm not proud of what I did. There were a couple women who were really interested in meeting me, even though they lived in California. One was ready to buy a plane ticket to Seattle, and I had to be nasty to her just to get her to give up on me. I could have told her the truth of my gender, but that may have been even more hurtful to her at that point (or so I rationalized). I was scared to death, and never fooled around with dating sites again."

Thanks for your comment! Mine as I said goes back to the very earliest days of the AOL chat rooms.  I was married too of course and somehow had managed to establish a fairly regular "chat" with a person attracted to transvestites in a city not so far away. Even I was very naive and continued the chat until my wife walked in on me one day and found out. I remember it took me weeks to dig out of that predicament  I had put myself into. It was almost as bad as when I was caught sending of Polaroid photo of me cooking in the kitchen all cross dressed up to a "friend" who responded with a perfume scented letter. Again, not what your wife wanted to find in the mailbox. Again I had to promise to never go down that road again. 

My problem was technology stayed one step ahead of me and I began to learn how to contact others. Of course, after my wife passed away, I was free to experiment on line and you have been able to see some of the results I had shared. Looking back on the later experiences, I think I was stood up on so called "dates" in restaurants approximately two out of three times by men. 

However I did much better with women whom I met in person and my future was to be much brighter. 

Going Out to be Alone?

Every once in while, or especially after the transgender - cross dresser support group meetings I go to, I like to reflect back to the early days when I was exploring the feminine world. Overall I was trying to figure out when and if I could live full time as a transgender woman.

Back in those days, for the most part I was having fun. These days I receive satisfaction from the rare days when I think I look my best. I know years ago when I went out, I liked to think I was going out to be alone.

Let me explain. First of all, I was still grieving the passing of my wife and close friends. I was intensely lonely but was aware any or all of my forthcoming friendships would have to revolve around me as a different gender. Not an easy thing to do.

Liz and I's vacation picture from the "Royal Gorge" train in Colorado.

So I cross dressed all up and went to several of the sports bars I used to go to before as a guy. For the most part I was successful. For awhile I was able to spend an evening in my own little world, thinking no one would notice my secret. It worked when I let nobody in.

As it turned out though, that didn't work very long. I found several people who were attracted to me as a friend regardless of my secret. Essentially, they found a way into my solitary world. Ironically, the people most interested in me were all women and I quickly bonded with them. I did have a couple dates with guys which never seemed to work.

Then I even went on several on line dating sites and found the person (Liz) I was destined to move in with and start a relationship which now is going strong at eight years.

Even at that point, I was still clutching at what remained of my guy self. He just didn't want to let go. It took my partner Liz to kick me totally out of the closet.

So now, I don't have to worry about going out to be alone anymore. I am so fortunate.