Update
Search: Sissy
6,943 stories
Sissy Boy
It never is easy to watch a loved one slip right into death's clutches. That torturous strain in your chest and sting in your eyes everytime you so much as get a little memory of that person.Being left with none other than a raging alcoholic as a father, the broken boy has to cope with life, going as far as indulging in self malignant acts in order to pull through. Ryder Hart never knew what hit him the day he stormed out of his house after his now rehabilitated father discloses news of remarriage. That day, he had come across the sheltered and timid crossdresser, Aleister Carter. Both boys seem to hit things off as friends, not even realizing the blossoming feelings they were slowly catching for each other. As time went on, these feelings bloomed, one was determined and the other was confused. In this romantic LGBT thriller, we watch as several obstacles get in the way of love between a depressed smoker and a sissy boy.โฅIdK9n65dโค WARNING!CrossdressingIncest20-04-2019 ....14-08-2019Summary editted by @TheHermit_Crab
Cheer Sissy!
this is the story of how Tim became Kim and found her true sissy calling: as a slutty college cheerleader! ** 18+ ADULT CONTENT WITH THEMES OF HUMILIATION, DOMINATION, AND GENERAL BDSM+SISSY CULTURE. THIS IS ALL FANTASY.
The Natural Sissy
Sebastian is on his way home after his first term at boarding school, a difficult term at a very special school, and he doesn't know what awaits him. He knows he has let his mother down, and he knows that he is in trouble, but he hopes he has survived the worst of his punishment and that things will be back to normal over Christmas. His new friends think otherwise, but educational petticoating is not for him, and he thinks his mother will agree...
Justin's Sissy journey
Justin has been getting in to trouble .so as a last resort his mother tries to feminize him.
The Natural Sissy and the Gang
Following on from The Natural Sissy, Sebastian Montague starts at the new sissy school and learns to make new friends, and enemies, whilst getting used to his new petticoated life. Expect thrills, frills and lots of tears as our sissy hero and his friends, and their parents, negotiate the perils and pitfalls of a petticoated life!
Princess Sissy Land
๐ Emma wants to change things up for her birthday. She and her three best friends, Lucas, Gabe, and Drew are going to "Pammie's Pretty and Pink Petticoat Lane," an incredibly girly amusement park.No one will be spared from humiliation- whether it be a pile of dresses fall on top of them, getting mixed up as an actor for the park's princess musical, or the various forms of high technology the amusement park brings (like a robotic dresser..?), they'll all be in for a feminine treat!Extra information: โ ๏ธAll characters in this story are over the age of 18. This is a fun fetish story, involving boys in dresses, some diaper-related content, some makeovers, tights, brief mention of underwear, and light swearing. (Any pictures in the story are not owned by me, and are used only to further depict scenarios.)Enjoy!
Becoming A Sissy
Tom is blackmailed by his roommate to pose as his girlfriend. This helps Tom discover he was born to be a sissy slut.
The new Sissy Academy
Paul drops out of his high school due to bullying from his classmates; However, before he can look for a new high school himself, a confirmation of acceptance for the "Superior International States School of Indiana" (SISI) is in his mailbox that same day. Without really realizing what is happening, he suddenly finds himself in the said institute, which is supposed to help him to his true (new) identity, which he is discovering bit by bit for himself...
I let AI write my story about a man becoming a sissy
Pretty simple, I asked AI for a few prompts where a man finds himself wearing a diaper and girl clothes: It spit out a few prompts, then I asked it to write a story. At the end of each chapter, I asked it to continue the story while prompting what should come next. I also asked the AI to rewrite parts that would have ended the story. Here is the result.
![My Sissy Baby [on going]](https://img.wattpad.com/cover/351820195.jpg "My Sissy Baby [on going]")
Sissy Farm
Back when Tumblr was cool, Brianna met Tim. Tim owned a farm in Pennsylvania and was looking for a live in maid. This is the story of how Brianna's life changed forever .
Tricked Into Feminization
This is a story of how Frank got Tricked Into Feminization by his family and other women.
Hobo to Dancer
Timothy was a homeless guy until he was offered to live with a rich couple with spare bedrooms. He's hired to work with Mitchell, a violent son of the billionaire and his boss. They have him follow a strict dress code and perform ballet as 'Tiffany '
Mommy's little princess
Samuel was a normal teenage boy until he started to wet his bed, he did it so much that his mother had enough and turned him into a sissy.This story includes -spanking-messy diapers-being forced in diapersThis story doesn't have anything that sexual but it may be uncomfortable to some. So if it is don't read this please!
Me n my sissy ๐๐
My Bestfriend has always been here for me and is like my sister has been here since day 1๐๐ค๐ฝ
Trust Me
Mia is a film photographer who made her living on her own and lives in the United Kingdom.Due to the fact that she is an avid gamer, she did not hesitate to say yes when presented with the opportunity to work as a set photographer on the first season of The Witcher.As soon as everything was settled, she hopped on the first flight to Hungary in order to get to the recording studio as soon as possible.She was taken aback by how welcoming everyone was toward her, and she found that it did not take her very long to adjust to the brand-new setting.Being social was not her problem, but being physical was.Mia didn't have to wait long to strike up a friendship with Anya and Freya, the actresses who played Yennefer and Ciri, respectively.However, her relationship with Henry, the story's lead character, was anything but friendly.Mia is the object of Henry's obsession, but she cannot let her guard down too easily around him.She longs to be able to let him in, but she knows that her past will prevent that from happening.Highest rankings.#1 in geralt#1 in night hunter #2 in cavill #3 in henry cavill
Undies for my son's growing butt
one day my son's butt started to grow read what all happened afterwards
from teen to a diaper wearing babay
jake is a normal 15 year old boy who is staying at his aunts elizabith she has a daughter named hannah and a son named luke