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

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

In Over my Head

Image from Alexander Mass on UnSplash In the beginning, it was all so simple. Pick something, I could squeeze into from my mom’s closet, try...