My Sissy Life's Journey, Devoted To Strong Women & Beautiful Trans Women
July 28, 2026
June 13, 2026
We Are The Sum of Our Life Choices
At first it all starts with a pair of panties..
Then it leads to some quiet dress up time...
The it grows to a small hidden wardrobe...But soon enough you find courage and seek others to help you...
Then a strong Woman to guide you...Then to help you repent for past male sins in new and exciting ways..
Until one day, you are nothing like what you started as...
And your new life takes over until you can't remember the old one...
And you finally become the sissy you were always meant to be...
April 29, 2026
April 21, 2026
June 20, 2025
The Room We Secretly Wanted
Imagine when you first became self aware of your sissy side if you could have had a bedroom like this? Just think of how your life would have accelerated into your Femininity!
January 22, 2025
January 11, 2025
You Told Yourself It Was Just a Phase...
Then a little dress up time to relax
Then your sissy wardrobe began to grow
Then your bravery grows, and you decide to step outside into your own little world to reveal the real you to the outside
Then you decide to pack a bag, check into a motel room and dress up away from your safe space at home
Then you step outside of your hotel room after a while and think about what it would be like to go for a walk as the real you
Then it's a small late night stroll outside
Then you find the courage one night to go to your local TS/TV/CD friendly pub
Then you realize there are others who are just like you
Then you realize you have a group of new friends who share your new found new life
Then you realize your new girlfriends have so much in common with you
Then you discover your new self in a new role
Then you find your place within your growing circle of friends
Then you discover your true love
Then you discover you can't live without it
Then you discover that all your courage and hard work pays off
Then you realize there is no going back to a life you once knew. This is who and what you have always been
Until one day you ask yourself why you didn't start sooner?Join the club...
December 29, 2024
September 21, 2024
Chastember - Go Deeper Sissy
There are a lot of sissies that truthfully, don’t have what it takes to be a bonafide sissy that is worthy of the name. I think it all begins with the proper mindset. Becoming a sissy to be proud of will require you to exorcise any ‘macho-man’ desires still left inside of you, or as I refer to it the EME (emasculated male ego) A true sissy is no longer a real male, but a chastised sissy. Being a sissy means you are no longer required to control anything or anyone. Your only role is now to perform the duties of a sissy for your Mistress. You simply do what you’re told to do. Couldn’t be any simpler than that.
The next issue is body hair. Women shave because it’s Feminine and sexy. As a sissy, you need to start shaving from head to toe…. no body hair allowed! Once you start to shave, a shift will begin to take place inside of your head. A transformation from male to sissy. You will be amazed at how quickly you become proficient at it. Before you know it, you will look forward to shaving more often.
Time to talk about clothes. Real Women adore the sexy feeling that soft, silky fabrics have against their body. If you work outside of your home, a pair of panties, garter belt, and nylons should always be worn under your work attire. When home alone, thong panties with a matching bra along with high heels should ALWAYS be worn. Start keeping your panties, bras and lingerie in one of your regular dresser drawers. There is no need to hide them away any longer. You are now becoming a true sissy so start acting like one.
You need to wear high heels constantly as you will need the practice to learn how to walk properly in them. This will take some time. As a new chastity sissy, you have a lot of catching up to do. You eventually will become very comfortable wearing heels, so much so that the time will arrive that you will never want to take them off (and why would you)!
You are beginning to look and feel like a real sissy. There is one problem though…. your undersized and under performing sissy clit. That's why your sissy clit is kept under lock and key. The only way you should ever be fucking a girl again is with a strap on dildo or face dildo. That’s your role as a sissy…. to serve…. preferably in the most humiliating, and frustrating way possible. If you don’t have a chastity device yet, it’s time to start thinking about ordering one. This is what Chastember is for! Long term denial will keep you in a constant state of arousal that will enhance your ability to perform your sissy duties in outstanding fashion.
A true sissy wants to always look as sexy and desirable as possible. Skinny is sexy! You will look better in Feminine clothes with an in-shape body. You are no longer a macho-man-pig that eats pizza and drinks beer. Sissies don’t do that. When you acquire that thin body that looks fabulous in your sexy sissy outfits, you will be super motivated to stay sleek and slim.
Let’s talk make-up. A capable make-up job will add the finishing touches to your sissy persona. If you don’t have anyone to help you out with this, it’s really not a bad idea to learn how to apply make-up yourself. This will take some time and practice to become good at, so start practising now! Besides the essential stuff to have in your make-up kit like foundation, powder, eye shadow, eye liner and lipstick, you should also add a lip-liner pencil in order to draw in fuller, sissy-like lips. And nothing will turn you into a desirable sissy faster than a set of extra long false eyelashes.
To recap, you’ve come to terms that your lot in life is as a sissy and completely given up on the idea of being a male any longer.
You’re now smooth and sexy, as in hairless.
You wear bras, panties, high heels and lingerie every chance you get.
Your sissy clit is now locked up (as it should be) and you are beginning to feel the benefits of long term orgasm denial.
You are losing weight as you want to be the best looking sissy you can be.
You’re taking every opportunity to improve on your make-up skills.
Being a true sissy is all about letting go of the need and desire to be a male any longer. It is so freeing; there is nothing to worry about any more. You no longer need to be afraid to approach Women. You will never again be nervous about asking a Girl out as you won’t be doing that any more. There will be no anxiety associated with getting it up and keeping it up. There are no dates to pay for or presents to buy. All your extra money will now be going towards make-up, lingerie and high heels. There is nothing more for you to concern yourself with other than looking as pretty, sexy and Feminine as possible.
Once you admit to yourself and the world who you truly are (a sissy), everything naturally just falls into place. You now think and act like a gurl. But remember, in order to completely remove any last remnants of masculinity, your dick must be locked up and denied. The only way to effectively do this is with a chastity device. Happy Chastember!
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