A silly little sissy must have all the tools she needs in her purse to take on the big bad world.
![Incentivizing an Increasingly Sissy Life](https://www.sissify.com/wp-content/uploads/2024/07/dresses-350x270.jpg)
Incentivizing an Increasingly Sissy Life
This sissy wishes to help herself become better over time. Her Superior absolutely will not apply any sort of correction, ...
![OMG can’t make this up](https://www.sissify.com/wp-content/uploads/2011/06/bangcock-gogo-350x181.jpg)
OMG can’t make this up
Curtsy girls. What carri is about to report is so crazy it has to be true. gurls you read this ...
![faeries dance!](https://www.sissify.com/wp-content/uploads/2024/07/IMG_2061-1-scaled-e1721503559758-312x350.jpeg)
Dancing With the Fairies: A Celebration of Life
An interesting lesson in that it’s not about the trials and tribulations of cross dressing. Rather it’s that we dress ...
![panties](https://www.sissify.com/wp-content/uploads/formidable/20/IMG_20240527_151143-1-350x157.jpg)
Secret sissy step 1: wearing my panties
Sissy is making her 1st steps, and even though she's not in the position to do anything openly, the training ...
![flirt](https://www.sissify.com/wp-content/uploads/2023/09/IMG_8522-e1709234686724-307x350.jpeg)
Mmmmmm the art of flirting!
This is one sissy is always been very good at, sissy lived with a transsexual hooker and had a line ...
![Will you be able to find a real Mistress?](https://www.sissify.com/wp-content/uploads/2014/11/realmistress-350x181.jpg)
Finding a Real Mistress
Humble greetings, and thank you for taking the time to read and grade sissychrissy’s training assignment report A sissy such ...
![Safety and first meetings](https://www.sissify.com/wp-content/uploads/2015/05/safety-featured-350x181.jpg)
Let’s be Smart and Safe!
Safety for a sissy who is going out on the town or meeting other sissy’s or a Superior for the ...
![resolutions](https://www.sissify.com/wp-content/uploads/2021/04/Screen-Shot-2021-04-09-at-8.50.49-AM-350x251.png)
Goals and aspirations for 2024
curtsy Greetings and a very Happy New Year to Madame Stewart, the House Staff and Superiors. chrissy has several Assignments ...
![Happy New Year!](https://www.sissify.com/wp-content/uploads/2016/01/vintage-new-years-pinup-via-blisstree-287x350.jpg)
2024 here we come ready to improve
jenn has been thinking quite a bit on what 2024 will bring, that being said jenn has set some goals ...
![The Future is Female](https://www.sissify.com/wp-content/uploads/2023/12/future-is-female-3-350x350.jpg)
2024 is the year of Twenty-Twenty Whore
Happy New Year sisters and a very Happy New Year to our Superiors and the Staff here at The House ...
![Resolutions](https://www.sissify.com/wp-content/uploads/formidable/20/resolutions-271x350.jpg)
Resolutions – getting started with purpose
This sissy is a planner. She needs to know that what she is doing contributes to progress and/or to something ...
![Will you be able to find a real Mistress?](https://www.sissify.com/wp-content/uploads/2014/11/realmistress-350x181.jpg)
Finding a Mistress!
Silvia's and other sissies' desires and dreams are not wrong. Our nature is unusual and exceptional. But, despite any negative ...
![panties lingerie oh my!](https://www.sissify.com/wp-content/uploads/2022/12/20221201_122448-263x350.jpg)
Being as feminine as this sissy can be
This sissy is still in the closet, but she always finds a way to be girly. This sissy always wears ...
![Finding a Superior](https://www.sissify.com/wp-content/uploads/2023/10/20231008_160302-scaled-e1698422068782-243x350.jpg)
Finding a Superior
First, this sissy wishes to give Ms. Selena Alcott a huge curtsey and a deep Thank You, for showing rikki ...
![secret sissy](https://www.sissify.com/wp-content/uploads/2023/06/20230622_101145-1-263x350.jpg)
You Wanna Keep This Secret Right?
There really is no use in pretending, this girl is a Secret Sissy. This girl tells everyone how much s.he ...
![annie](https://www.sissify.com/wp-content/uploads/2023/03/IMG_27761-263x350.jpg)
When she was 6 she was little and quick.
annie recall's peeing in her pants at 6 and Mother placing her in her sister's underwear! She was small for ...
![jenn](https://www.sissify.com/wp-content/uploads/2022/11/image-1-263x350.jpeg)
sissy’s first road trip
Dear Madame Stewart, Superior and House Staff: sissy jenn is a secret sissy and has been for quite a while ...
![Resolutions](https://www.sissify.com/wp-content/uploads/formidable/20/resolutions-271x350.jpg)
sissy resolutions
This pathetic sissy resolves that by the end of 2023 she will be open with her wife and friends about ...
![Panty Flash](https://www.sissify.com/wp-content/uploads/2019/11/flashthosepanties-350x197.jpg)
nikki’s secret sissy adventure
“A day without panties is like a day without sunshine.” Unfortunately, for various reasons, namely family and job, nikki is ...
![secret sissy](https://www.sissify.com/wp-content/uploads/2022/11/IMG_0012-263x350.jpg)
Hiding My Femininity in Plain Sight
Good Afternoon to my Superiors This sissy does her best to always have on some Women's clothing, not just her ...
![Getting Real](https://www.sissify.com/wp-content/uploads/2014/11/getting-real2-350x181.jpg)
Being Ashamed
I was very subdued, as I served my wife/Mistress one evening. She was happy, and smiling as I brought Her ...
![Getting Real](https://www.sissify.com/wp-content/uploads/2014/11/getting-real2-350x181.jpg)
Assuming Positions
I was honored to be owned by a creative Mistress when I was younger. She enjoyed feminizing me, and punishing ...
![janie is beautiful!](https://www.sissify.com/wp-content/uploads/2022/08/Janie-No-Make-Up-Denim-Shirt-08.2022-1-263x350.jpg)
What Price A Pretty Face
Curtsey Dear Madame Stewart and Staff Superiors, janie is by way of being an “advanced” sissy. Meaning in polite parlance ...
![So you want to tell Her?](https://www.sissify.com/wp-content/uploads/2014/11/tellher-350x181.jpg)
Being Excited
Being a 'two spirit', isn't easy for a man (sic). i do well as a man (sic) , i was ...
![Safety and first meetings](https://www.sissify.com/wp-content/uploads/2015/05/safety-featured-350x181.jpg)
Lessons Taught To Our Girls by The House
janie was delighted with this Training Assignment and found a great deal of sense; which may go unheeded in the passion ...
![skirted slave](https://www.sissify.com/wp-content/uploads/2018/03/skirted-slave-featured-2-350x181.jpg)
Being Excited
i was excited, one evening, early in my marriage. i had told my wife that i was a sissy, and ...
![Punishment of a sissy](https://www.sissify.com/wp-content/uploads/2018/01/punishment-sissy-featured-1-350x181.jpg)
Real Punishment
This sissy’s Mistress is brutal when punishing sissy. sissy is required to confess any transgressions to Mistress. These transgressions can ...
![You can't judge a book by it's cover!](https://www.sissify.com/wp-content/uploads/formidable/20/20211114_193136-scaled-e1644034395294-225x350.jpg)
You can’t judge a book by it’s cover!
Since this sissy joined the House, she has been increasing her sissiness and feels that now is the time to ...
![secrets](https://www.sissify.com/wp-content/uploads/2017/12/secrets-peter-thiel-zero-to-one-startups1-350x321.jpg)
A secret…. no more!
For years previously this sissy had been a Secret sissy; stealing panties where this sissy could, trying on items of ...
![mansplain](https://www.sissify.com/wp-content/uploads/2021/10/mansplain-350x350.jpg)
A Repentant Sissy Who Lost he.r Way.
"Punishment follows transgression and precedes Repentance" mansplaining - "The explanation of something by a man to a Woman in a ...
![sissy erin](https://www.sissify.com/wp-content/uploads/formidable/20/20210710_194535-350x350.jpg)
erins first big adventure
This sissy was privately messaged and encouraged to submit a report on her first time out dressed at erin, hope ...
![Tell her!](https://www.sissify.com/wp-content/uploads/2015/03/tell-her-350x263.jpg)
Being Superior
For weeks, months, maybe years, this sissy had been journeying towards acceptance. All he.r life, since the loss of he.r ...
![Flirt!](https://www.sissify.com/wp-content/uploads/2017/02/Katie-Cassidy-Wink-350x214.gif)
Mistress Flirting
sissy’s Mistress is a world class flirt. sissy read this assignment but this report may not qualify as sissy would ...
![Secret sissy](https://www.sissify.com/wp-content/uploads/2017/11/secret-sissy-small-350x350.jpg)
Secret sissy starts subtle sissification
This sissy suggests that most sissies need to be secretive in some way about their sissy feelings. Perhaps they are ...
![secrets](https://www.sissify.com/wp-content/uploads/2017/12/secrets-peter-thiel-zero-to-one-startups1-350x321.jpg)
my secret sissy self
This sissy has always had this secret side to her. when she would go out shopping for panties she would ...
![Glitter Party!](https://www.sissify.com/wp-content/uploads/2020/05/glitter-rupaul-350x197.gif)
We have all been in over our heads
Dearest Mistresses, The ideas given in the lesson on Safety for sissy's is valuable advice. Ah, but young developing sissys, ...
![So you want to tell Her?](https://www.sissify.com/wp-content/uploads/2014/11/tellher-350x181.jpg)
So the journey begins
A year into dating, naomi bought a beginners strap on set for h.er Superior for Christmas. The gift was received ...
![Beach Panties](https://www.sissify.com/wp-content/uploads/2020/05/beach-panties-350x269.gif)
Wearing panties to office
This sissy put on h.er newly bought pink hips panties for the first time at work when h.er went to ...
![The many first time of kaori.....](https://www.sissify.com/wp-content/uploads/formidable/20/IMG_1168-263x350.jpg)
The many first time of kaori…..
This little sissy will like to thank the House and Superior to look to this slice of life of kaori, ...
![resolutions](https://www.sissify.com/wp-content/uploads/2021/04/Screen-Shot-2021-04-09-at-8.50.49-AM-350x251.png)
Attaining and maintaining
Curtsy This sissy has been floundering. It is so glad that it found this topic. It set a goal late ...