When We were Against the Law

 

Phil Donohue on left with singer (male) 
Grae Phillips.

I am old enough to remember the days in Dayton, Ohio when transvestites and or cross dressing men were loaded into police vehicles and arrested. 

Since I was just discovering my attraction to feminine clothes, of course the whole process scared me. I did not want the police to come in and arrest me. Then, the Stonewall Riots happened in New York City in 1969 and all of a sudden there was a glimmer of hope for me again. The outside world was changing, or so I thought as I watched and learned from my home in faraway Ohio. I was in my second year of college and the world was changing for me also. As the world on occasion seemed to tip in our favor when movies such as "Tootsie" were released in 1982. 

Then there were the flood of talk shows from "Phil Donohue" to" Jerry Springer" who focused on the the so called married cross dresser and wives. Many were trash and did the transgender or cross dressing community any good.  Donohue ran from 1970 until 1996. Sadly we were left with being items of ridicule on "Springer. " We were not against the law but close. 

Now of  course we face the most difficult times a transgender woman can face. If the orange menace and his cronies find their way into power, we in the entire LGBTQ community face a real threat to our very existence. I live in Ohio and the anti-transgender political ads against Democratic Senator Brown have been ridiculous. In fact they out and out lie. What amazes me most is when I encounter a pro-tRumpt transgender person. I have had them tell me they believe him when he says he had nothing to do with Project 2025 and they are safe with him in office.

I stand with all women and support their right to control their own body. I also stand with the candidate which does not threaten our future existence as transgender women and trans men. I think you know who I am referring to. 

I know nothing I can say can influence your vote. In fact, you may have already done it. I just hope enough see through the barrage of lies and vote in our first woman president.  

When Every Night is Girls Night

Grae Phillips is still active
on Facebook if you want to 
see more. Or just keep up. 

I know I make a big deal out of my second huge transition, when I mentally moved from being a serious part-time cross dresser into being a novice transgender woman.

Sometimes I feel as if I am putting myself on some sort of a gender pedestal when I write about not considering myself a cross dresser anymore. If it comes off that way, I don't mean it to. On occasion, the written word gets in my way. Getting back to the cross dresser versus transgender statement I made, I think in my case, it was a matter of me judging my own life. Originally, as I was working my way through my early years of admiring my girl self in the mirror, I knew it could never be enough. There had to be more. I was so tired of cross dressing for one day and then two or three days later wanting to do it again. 

As I always mention, all of this occurred back in the pre-internet information era when any news and contact with like minded gender individuals, be they transvestites or transsexuals, was very difficult and rare to come by. This was even before the barrage of talk shows led by the late Phil Donohue who interviewed female impersonators such as "Grae Phillips", all the way to transvestites seeking approval from a doubting world. It was quite a bit for me to sort out. But I did. I knew I could never be as beautiful and talented as Grae but I could reach the standards of most of the transvestites I saw on my television. There was hope for my future after all.

As I progressed into meeting more and more diverse cross dressers or the women known as the new transgender group I began to think what it would mean if I went all the way and every night became girls night. In other words, a time when I would never have to go back to my old male self and live. Deep down I knew there would have to be some sort of line drawn in the sand if I did. As much as I loved all the fun of the newness of applying makeup and picking out clothes, I wondered what would happen when the newness wore off and I needed to settle into the daily routine of the transgender womanhood.

It turned out, I had nothing to worry about. I settled into my new feminine routine as if I had always should have been living this way. I found I didn't have to do much special on many days such as most cis-women do and then again still have the fun of dressing up for special occasions. It was true, once I jumped the gender border from cross dresser to transgender, I could experience what life could be like if every night was girls night.  

One Gender Size does Not fit All

Image from Grae Phillips 
on Geraldo television show.

 If the truth be known, all the way back when I was a kid struggling to understand what gender I was on any given day, I would have been known as gender fluid. 

Of course, gender fluid was a term which hadn't been invented yet. Anyone who was interested in cross dressing was branded as being a transvestite and even worse labeled as being mentally ill. In the middle of my gender vacuum, even I knew well enough I was not mentally ill just because I wanted to wear makeup and dresses. I hid my desires and hoped for the best, which mostly came when I was left alone to cross dress and admire myself in the full length hallway mirror at home. Most of all, I was trapped and could do nothing about it. Keep in mind, all of this was happening in the information "dark ages" before the internet and social media. The gender underground I was interested in came mainly from the pages of Transvestia Magazine and Virginia Prince. Even I knew the pages of the "National Enquirer" and other predecessors of Faux News who sensationalized cross dressers were not to be trusted.

Then came the barrage of so called reality television talk shows including, Donahue, Springer and Raphael. All of whom seemed to be pushing the theme of cross dressing husbands Except for the impossibly beautiful and talented "Grae Phillips" who put everyone else to shame. All of these shows probably did little or no good for my gender dysphoria except for publicizing the fact there were cross dressers of transvestites of all kinds at all. All I knew was I desperately tried to watch or tape every show I knew was coming up from my "TV Guide". My wife was trying to tape her soaps and I was trying to tape my talk shows and both kept us busy. Even though I still had to watch my shows in private attempting to learn anything I could about the outside world.

I did learn once again. my gender size was unique and did not fit all. In fact, I still felt out of place when I started to attend my first cross dresser - transvestite mixers here in my native Ohio. I discovered there were so many different levels of participation from transsexuals headed for gender surgeries down to the weekend cross dressing hobbyists.  For some reason, I was not part of either group and once again my gender size was not fitting in. The problem was, all of this happened before the transgender terminology was introduced. When it was and I started to have access to my first computer, I was able to research the term which was unknown to me. Suddenly I knew what had been missing my whole life, a gender size which fit me and I set out to discover more about being transgender. For me, it meant being part of a gender description which was somewhere in-between the spaces I had been in previously.

Even though my gender size did not fit all, finally I was able to locate my own niche to thrive in. Life became fulfilling, scary and exciting at the same time. I found out I was fine being who I was all along and it felt so natural. I was home. 

It's a Man's World?

One of the first things I learned was when I entered the feminine world was how I lost almost all of my relevance when talking to men. I remember vividly jumping head long into a conversation one night with three men and getting totally patronized. I thought "Oh! Is this the way it is going to be?" Well, it was...and worse. Soon I learned I had lost most of my intelligence too.

After I had transgender transitioned into the world for awhile, I learned the truth. The idea men run the world is a myth, except for Washington. And, how is that working for us? As I absorbed what I needed to live as a woman, I learned the feminine rules I would need to survive in the real world. In other words what women did to talk around men or how they would bide their time until they got their way. The two "P's" of my new life became all too real. Passive aggressiveness and patience. Both were needed to get by in my new life.

So it may indeed be a man's world but women run it.

Sometimes I wonder what a person like Grae Phillips would think? Did he ever become so engrossed with being a female impersonator that he lost any perspective about being male at all. Or did presenting himself as a guy presenting as a woman provide him with the publicity to build a career? Since he does not read Cyrsti's Condo that I know of, I will never know.

Speaking of Grae, Connie had her own take on Phillips career being an entertainer herself:

" My guess is that his act is no longer relevant. Also, age is not a woman's best friend - especially in the entertainment industry. Shows like "Dragrace" have taken the novelty to an extreme, and this is (to paraphrase) no country for old queens. Not that Grae was ever really a drag queen, but that could be part of the problem of relevance today. Most likely, though, the whole act lost relevance for him. After all, he says that he only did the female impersonation because he was getting nowhere in show biz as a male performer.

As a singer, myself, I can only dream of having a voice in such a high register as Grae's. Still, unless I wanted to do a full-on drag act, there is not much call for a transgender woman singer these days. Of course, I don't see myself as anything other than a trans woman who sings, and I only want to be seen as that, as well. Even if I am, though, it's tough to be convincing when I'm a 68-year-old singing "Making Whoopie." I imagine that it would be the same for a female impersonator, too."

Good point! Thanks.

Remembering

For some unknown reason, my steel trap noggin (which is seriously rusted) came up with a female impersonator from the past. Perhaps you remember too when cross dresser extraordinaire Grae Phillips took the daytime reality show circuit by storm. As I recall, Grae was a struggling singer in New York before he went the "Tootsie" route and started to perform as a woman.

I couldn't find any ideas on if he is still performing today.

If you know, please let me/us know.
 

"Fade to Grae?"

Recently, I presented a "Flashback" post and photo on female impersonator Grae Phillips (left) who, according to Cyrsti's Condo visitor:Lynn Davis  who commented: "Grae just sort of vanished."

Indeed Lynn and here is what I think happened. 


From the very beginning, Grae was a drag queen who could sing and perform as a woman, rather than a parody. Good enough to parlay her act into a singer for a real group or band.


 By then, Grae was in a prime spot back then to cash in on the "real life Tootsie" idea as well as the "explosion" of talk shows eager to "expose" any cross dressing issues.


Today, all I can find is a series of sales pitches and old videos of Grae as a woman and a man.


I have also considered Grae was sort of a womanless beauty pageant winner who hit the mainstream and disappeared just as quickly when the beauty and fame began to fade.


If anyone else has any other facts or ideas, please let us know!

 

Cyrsti's Condo "Flash Back"

Grae Phillips was one of the first glamorous transvestite/female impersonators I saw back in the 1980's on talk shows such as Phil Donahue. As I remember it, Grae's story was he couldn't make it as a male singer in New York, happened (??) to discover he could be a very convincing feminine singer-with a very convincing look:

Cyrsti's Condo "Cover Girl" of the Day

Our feature cover of the day today is a very "80's" looking Grae Phillips.  If you don't recall Grae's story, he was billed as the "original Tootsie." I still remember clearly when he made his first appearance on the Phil Donahue Show.  He couldn't land a job as a guy singer in NYC and just " happened" to throw on a dress and makeup with the help of a girlfriend and was much more successful performing as a woman.
There are tons of Grae's videos on YouTube plus you can follow the link above for a website.

Grae Phillips

As far as I know, Grae Phillips was one of the first in my generation to hit the talk show circuit looking and sounding exactly like a tall sexy female singer. If my memory serves me correct, Phil Donahue was where I first saw Grae. Here's a look at the talented female impersonator on our Cyrsti's Condo big screen: