Showing posts with label sissies. Show all posts
Showing posts with label sissies. Show all posts

Sunday, April 26, 2026

My Life's Passion

JJ Hart on vacation
last winter. 
Without a doubt, the one passion which has consumed my life the most has been my desire to be a woman.

I continually write about my youth as a confused boy wondering if I was the only boy in the world who wanted to be a girl. My desires extended all the way to what I wanted for Christmas (the doll baby I never got) all the way to when I lied about what I wanted to be when I grew up. Rather than rock the boat I always said some sort of a male profession such as a doctor or a lawyer rather than what I really wanted to be, a woman.

All I could do was take refuge in my mirror which told me I made a pretty girl out of the boy I was at the time. It became a passion for me to use as much of my free time as possible to cross-dress. At the same time, I became really good at acting like a boy by playing sports and having an interest in cars. I was so good, it kept the bullies away until male puberty invaded my body. Outside of hating the changes puberty was making to my body, I remember being intensely aware of my new masculinity and what to do with it. Even walking like a man was a chore for me to learn to do. I was so afraid of walking like a “sissy” and be made fun of by the bullies that I feared what to do. Little did I know that later in life my passion would be to unlearn all that I needed to learn at the time about being masculine.

As much as I tried and as tormented, I because of my gender passions, I could not seem to lose my desire to be feminine over my hated male image. At the time, I was in the midst of what I call the information “dark ages” before the internet and any social media input. Even the word transvestite was new to me as I struggled to find my footing in life. In other words, my gender closet was very dark and lonely, with little opportunity to have any future at all in my passion to understand and be feminine.

I stayed that way until I grew older and my passion included receiving my cherished issues of “Transvestia” magazine and I could read the “wisdom” of “Virginia Prince” whenever I could get my hands on another issue. For a while I thought it was working until I began to read about the social mixers certain chapters had to meet and greet other cross-dressers or transsexuals as they were known back in those days. Amazingly, one of the chapters in my native Ohio held mixers on a fairly regular basis that I could attend. I thought for sure, meeting others with similar gender issues could help me but I was wrong. Their passions exposed the many layers of where I could fit in (or not) with the remainder of the cross-dressing community and at the least, I hoped I could come away from the social by making a friend or two.

The only thing that really came out of the mixers was the knowledge that another chapter was coming close to establishing their own socials in Columbus, Ohio which was vastly closer for me to attend. Maybe I was too standoffish or even shy to make what I would call friends, but I continued to keep going any way and even was rewarded with invitations to smaller more diverse parties in Columbus which did not have to supposedly adhere to all of “Virginia Prince’s” archaic rules such as admitting heterosexual members only. As I said, the parties I went to were very diverse from lesbians to cross dresser admirers all the way to transgender women getting ready for gender realignment surgeries. The learning process I went through every time I went fueled my passion to learn more about my place in this new exciting world, I was becoming a part of. I could not wait to be invited to the next party.

I felt so secure from my party experiences, that I decided to do more exploring in my own in public. That is when I began to seek out the straight venues I used to go to as a man when I always wondered what it would be like to experience them as a woman. My passion for my new life exploded when I discovered I could be accepted which kept me out of the gay venues which I did not feel comfortable in at all. I was able to go out to be alone and mostly socialize by myself for the most part as I worked hard on my passion to fill out my gender workbook which was seriously lagging behind my fast-paced life as a novice transgender woman.

By this time, I had decided I had made the right decision to follow my feminine passion and try to survive in a world run by ciswomen. My path felt natural and I was rapidly coming close to the time when I was going to push all my male privileges I had earned to the middle of the table and bet my life on the transfeminine path I was on. I could not believe that my entire life’s dream/goal was suddenly within my grasp. If only I had the courage to finally follow through on my passion.

I did follow through and with the help of my future wife Liz, I went on HRT, threw out or gave away all my male clothes and never looked back on my male life except to decide which baggage to bring with me. I even went as far as taking female vocal lessons to try to teach me all important feminine communication skills which I desperately needed. It all turned out to be a labor of love as I listened and learned from the world around me.

The boy so long ago in the mirror finally had his deep-seated passions rewarded.

 

 

 

  


Sunday, August 10, 2025

Low Risk...High Reward?

 

Image from Jayson 
Hinrichsen on UnSplash.

There are many things we do in the gender universe which represent a low risk, high reward effort.

For example, under the cross-dresser umbrella, we have the far-ranging participants who go from wearing panties under their male clothes, all the way to those who fully dress as transfeminine women in their spare time. At the least, there is more risk to the cross dresser who is fully dressing in feminine fashion and makeup than the person who simply needs to pull his pants up to cover his panties. At some point too, one must consider if wearing women’s clothes is simply a fetish or is there more to it. Which carries even further into the world of sissies and such which involves men who fantasize about forced femininization.

In my case, even though I deeply felt the pleasure of hose on my shaved legs, or other beginning thrills such as looking at myself in the mirror, deep down I knew there was so much more to what I was doing about my developing gender issues. I knew too, if I was ever caught with my clothes and makeup on, there would be no rewards, just risks, so I needed to be very careful. All the way to the point of never wearing panties under my male pants at school and on rare occasions dreaming about a woman forcing me to cross dress at all. Ironically, I talked a woman into dressing me head to toe as a woman only one time and I ended up thinking I could have done it better myself. The risk of telling her did not equal any reward at all.

The risks and rewards proportionally grew greater together as I grew older and my male life began to grow. Many times, without my feminine one who was still stuck in her mirror. It was in the Army of all places, when I first came out to a small group of friends that I was a transvestite and much more than the fully cross-dressed woman they were able to see at a Halloween party. Naturally, it was a huge risk to take because the Army could have taken measures to discharge me. The reward did come when I was able to finally feel the relief of telling someone else my deepest secret and no one cared.

The further reward of coming out of gender shell was the fact my first wife was in the group of friends I came out to. Our marriage then led to the greatest reward of my life…the birth of my daughter who supports me to this day.

As my male world kept expanding and threatened to take over my transfeminine experience, I was going through a wonderful period of great discoveries in my life. Those were the days when I first discovered the transgender term and what it meant to me. For the first time in my life, I found a community which I belonged in. I was too much woman for the average low risk cross dresser and too little for the risk it all world of the transsexuals who were headed for gender realignment surgery.

I was so comfortable in my new place in the world, I was prepared to take bigger and bigger risks. Much to the chagrin of my second wife who had no problem with my cross dressing but was totally against any thoughts of starting gender affirming hormones and living increasingly as a woman. Every time I went out to explore the new feminine world I was creating, I was risking my twenty-five-year marriage. Because I chose to lie to myself for many years of denying who I really was, I ended up making us both miserable.

My excuse was I knew I would be losing a great marriage, a substantial job and many hard-earned male privileges if I threw all my cards into the middle of the table and came out into the world as the person I was always meant to be. Finally, the choice ceased to be mine as I embraced my new feminine self. My wife had passed away, I reached the point where I could retire from my job, and I was eager to check out the world of female privilege. It was all a huge risk, but I had to take it as I was nearing the age of sixty and I figured I was near a now or never moment in my life.

I had never been a gambler of any sort, but I wished I had the courage to make the move I made earlier. One thing is for certain; you can never rewind your life to make up for past mistakes. You just have to do the best that you can of your past to plan ahead for the future risks you will have to take.

 

 

Tuesday, August 25, 2015

Where Did the Pool Sissy Go?

I don' really know, but if you are wondering where the picture of the cross dressed "sissy" went, Pinterest had a problem with me re-pinning it at all. It turns out unless I received permission to use our boy at the pool-I couldn't, he was copyrighted.  

Either that, he was recognized and caught?

Tuesday, February 25, 2014

Call the Maid!

 For those of you who visit Cyrsti's Condo who need a maid service, here are a couple of sissy suggestions!








He likes ruffles and petticoats and being his girlfriend's special maid.

Monday, August 13, 2012

The Cross Dresser as an Artist

One of the labels which seems to be lost in today's fast paced cyber world is female impersonator.
Over the weekend, a friend of mine sent me a couple of simply horrid cross dressing video's which have caused me nightmares.
Most of you know I love to connect the dots.
In this case, the difference in the closeted cross dressers who excel at the art form and those who don't are the dots.
First of all I know all of us are not created equal. All of us who played football in our past I'm sure now admire those guys with slim builds. (Yes I did play on the defensive line)
That's just the beginning. As one of the young transgender college students recently wrote "who teaches a 14 year old boy how to use makeup"? Take it a step farther "who teaches a 35 year old cross dresser"?
On YouTube...sometimes no one.
But other times you can see the sheer artistry some put into their obsession. You can read in their profiles they are closeted and are part time girls. They have decided "the street" wasn't for them. I have an example from a cross dresser I knew years ago. I recently found a Christmas card photo he sent me which was stunning. No possible way anyone would think the woman in the picture was nothing but a beautiful red head in heels, garters and heels. Of course I knew in person the woman in the picture probably couldn't present well in public- all 6'2 of her-without heels. There were other factors too.
(Today height is not the problem it was. Seemingly women have grown since then and tall girls in heels today are common. Ask Stana)
Regardless of any of that, she was the consummate female impersonator in those pictures. You can log into Flickr or other sites and find quite a few. I'm sure we all know their looks aren't just by accident. All of them work long and hard to perfect it-physical limitations or not.
What I can't wrap my pea brain around are those who don't. I desperately want to feel sorry in a sense for one of my cross dressing sisters who scorched my eyeballs prancing around in a Marilyn Monroe dress, blond wig and drink.  I just couldn't. I wondered if he had enough of that drink to think all was good?
I really don't begrudge him the right to do it. Insightful pictures and videos can be part of a great self education feminine program. I just don't understand  the need to go public with it?
I'm guessing he is a 60 something cross dresser and interestingly would transform into a rather realistic woman of his age.
Keep in mind, I also know there are many individuals who are only into fetish roles such as sissies or petty coats also.
By this time there are too many dots and too little time to connect them in our culture.
The good news is my eye balls are starting to recover and I have a sharp pencil.

Saturday, June 23, 2012

Working Smarter not Harder as a Trans Girl

  Image from Erik Mclean  on UnSplash. Before we get started on today’s post, here is a little background on my annual visit to the endocrin...