Stories

The following are short stories written by Tiffany Chastain. They are available to read to read on Kindle, Kindle Vella, and Kindle Unlimited.

Sissy Study Buddies

The school year’s almost over, and Robby isn’t ready to say goodbye. Leaving his dorm also means leaving his study buddy, Drew, and he’s worried that time apart will break up their newfound friendship.

So, when Drew seems uninterested in their final exam, Robby comes up with a fun idea. He challenges Drew to a bet based on their test scores. But things take an unexpected twist when Drew declares that the loser should dress up as a sexy school girl.

As things unfold, the bonds of their friendship will be tested as they explore new interests in dressing up and feelings for each other.

My Stepsister’s Sissy Bridesmaid

After an attempt to kiss his stepsister, Heather, leads to a family fallout, Miles is surprised to hear that she wants to pay him a visit. During her visit, Heather surprises him with the news of her engagement, leaving Miles feeling surprised and disappointed.

The news gets worse when Heather tells him that their family doesn’t want him to attend her wedding. But being that it’s her wedding and she wants her stepbrother there, Heather has an idea to get around her family’s wishes.

By dressing him up as one of her bridesmaids.

My New Job as a Sissy Maid

James has been unemployed for over two months, and his lack of progress in finding a new job is causing distress for his wife, Anna. He also hasn’t been making good use of his extra time at home. He hasn’t been cooking, cleaning or fixing any of the issues around the house that he had promised his wife that he would.

When Anna comes home from work and finds James on the couch, absorbed in video games yet again, she has had enough. She comes up with a plan to make James into a more useful, participating member of the family. By transforming him into her maid.

Follow along as Anna transforms her once useless husband into a submissive and obedient sissy maid.

From Intern to Sissy Secretary

Jacob has just started his new job as an intern at a top-shelf sex toy company. He’s bursting with ambition, aiming to make it big within the company’s ranks. While he’s still feeling his way around, a chance encounter with the striking and influential Senior Vice President, Victoria, takes his journey in a surprising direction.

In department dominated by women, Jacob stands out, becoming an intriguing asset for Victoria’s needs. She’s on the lookout for someone to test a new product line, and Jacob fits the bill perfectly. He’s introduced to a prototype chastity cage, and after a bit of persuasion, he’s convinced to give it a shot—with Victoria’s hands-on assistance, of course.

Unbeknownst to Jacob, he’s stepping into uncharted territory, oblivious to the potential of the chastity cage and Victoria’s newfound hold over him. Soon, as he earns his promotion to become her personal secretary, Jacob will learn what it means to be a sissy and will learn how good it feels to be a submissive to a powerful woman.

Sissy’s First Date

After a night of fun drinking with his friend Olivia, Ben is ready to call it a night and head home. However, Olivia has other ideas and convinces him to join her at her place for more fun. Once there, she suggests they play a game of Truth or Dare.

What Ben doesn’t realize is that Olivia has a secret plan in store for him. As the game heats up, he ends up wearing her clothes and getting locked in a chastity cage, and it becomes clear that Olivia’s playful game is part of a larger scheme—to transform him into her sissy.

Read the FULL story of Ben’s tale of transformation as Olivia unravel’s her plan to turn Ben into Becca, her new slutty best friend, and teach him what it’s really like to date as a woman.

Feminization Camp

Neil and his wife Daphne have finally reached a breaking point in their relationship. After years of Neil playing the traditional “man” role and leaving all the household chores to Daphne, she’s had enough. She gives Neil an ultimatum: Attend Camp Transcendence, or their marriage is over.

Feeling resentful but with no other choice, Neil begrudgingly agrees to go to the camp, thinking it might be a nice escape. Little does he know that Cindy and the other counselors are determined to keep him busy and teach him what it truly means to embrace femininity. It’s going to be a transformative experience for Neil, whether he likes it or not.

Follow along as Neil learns what it truly means to be a woman through the lessons and exercises of Camp Transcendence.

Feminized By My Best Friend

Nick has carried a secret crush on his best friend, Samantha, for as long as he can remember. But when it comes to romance, she has always been out of his reach and out of his league.

But life takes an unexpected turn when Nick lends a hand to help Sam move and stumbles upon a box filled with her lingerie. Lost in the allure of the delicate garments, he becomes completely absorbed, momentarily forgetting that Sam is in the room with him, watching his infatuation of her panties.

Little does Nick realize the familiarity he will soon have with Sam’s lingerie and the surprises that await him, as Sam unveils her secret plans, forever altering the course of their relationship.

Read the full story of how Sam helps Nick transform from her best friend to her girl friend.

Becoming My Mother-in-Law’s Sissy

Evan leads a comfortable life following a comfortable daily routine of going to work, followed by relaxation at home with a beer and some video games. His wife, Maddie, takes care of dinner and keeps the house clean, creating what seems like the perfect existence.

Not everyone is content with this arrangement, however. Evan’s mother-in-law, Yvonne, disapproves of his behavior and how he treats her daughter. After months of urging Maddie to take action, Maddie finally agrees to allow her mom to try an unconventional and drastic measure to transform Evan into a better husband: a chastity cage.

Maddie presents Evan with an ultimatum: wear the chastity cage or risk losing her. Evan reluctantly agrees to wear the cage, unaware of the profound changes that await him. And unaware of how he will soon fall under the submissive spell of his mother-in-law.

My Neighbor’s Sissy Maid

When Henry suddenly attracts the attention of his beautiful neighbor, Laura, he is surprised. She used to be friends with his ex-wife, but they had never spoken much themselves. His surprise, however, quickly turns into disappointment when Laura asks him to rake her lawn. But he’s quickly enticed when she says she will reward him for his hard work.

Henry agrees and gets to work even though it’s beginning to rain. By the time he’s done, the rain has left him drenched. Laura invites him inside where she has him undress so she can dry his clothes… and so she can give him his reward, the opportunity to wear her clothes. An opportunity that could change his life forever.

Follow the story of Henry as he becomes Hannah and Laura as she becomes his dominant mistress. Through practice and the right amount of discipline, Henry begins to eagerly transform into his neighbor’s good, obedient sissy maid.

Feminized by the Maid

Living back home for the summer, Alex has his eye set on his family’s maid, Tiffany. He hatches a plan, hoping to finally seduce her, but when it backfires she threatens to tell his parents.

Worried that his family will cut him off, he quickly becomes desperate and begs for forgiveness, telling Tiffany he will do anything. She decides to make him dress up as her and be the maid for the week. She will have her hands full training him to be a good and obedient maid and he will have his hands, and mouth, full in more ways than he could have ever expected.

Read the full story of Alex and his no nonsense mistress Tiffany as he learns what it takes to be a sissy maid. And he learns to love it.

The Replacement Maid

Chad’s wife, Rachel, is always pestering him to help clean the house, but as the man of the house he sees this as women’s work and her responsibility. After endless fights, they finally come to an agreement to hire a house cleaner to help around the house.

This is exciting news for Chad. One of his friends had told him about a company whose cleaners come dressed as sexy French maids. He eagerly orders one and isn’t disappointed by the beautiful maid who arrives. He is disappointed, however, when he learns that she’s actually an escort and has no intention of cleaning. Panicked and needing a solution, Chad decides to become the maid and do the work himself.

When his wife finds out, she decides to teach him a lesson by locking him up in chastity and forcing him to become her maid. With the assistance of her friend Kelly, Rachel teaches Chad a valuable lesson. What his place in the house really is and why she is actually in charge.

Blackmailed Sissy Maid

Chris has a secret, he likes to wear women’s panties under his clothes and even sometimes sneaks away to his office to wear dresses and lingerie. But what he doesn’t know is that his wife, Amy, has find out.

When Amy confronts Chris, she forces him to reveal his stash of women’s clothing by threatening to reveal his secret to the world. But that’s not all she has planned for Chris. Seeing his secret wardrobe inspires her to make him dress up. And seeing him dressed up gives her an even better idea. To make turn him into her sissy maid.

Read the story of how Amy transforms her husband into the perfect, submissive sissy husband.

Frat House Sissy

How far would you go to be accepted into the best fraternity on campus?

When Greg and his best friend Tyler have a chance to rush one of the oldest and most prestigious fraternities on campus, they can’t pass up the opportunity. Through a series of tests, the fraternity will determine if they are worth of becoming new members.

For Greg and Tyler, emotions start to stir and new feelings begin to bloom as they support each other during the unconventional hazing. These feelings only flourish once they are accepted into the fraternity and their new roles within the house are revealed.

Training For Sissies

When Daniel accidentally signs up for sissy training while searching for physical training, he’s in for the surprise of his life. But it’s too late to stop. Daniel quickly, and eagerly, succumbs to the demands of his new trainers and mistresses, Scarlett and Ruby. Through their physical and mental training, Daniel quickly learns the in and outs of the sissy lifestyle. And he likes it.

Follow Daniel through his ten week sissy training course as transforms into Danielle, the obedient and subservient sissy, and learns that his accidental enrollment was no accident at all. It was his destiny.

Turned Sissy By My Lesbian Girlfriend

Jack and Maya are deeply in love and living a perfect life together. Or so Jack thinks. Maya has a secret she has been hiding; she has recently admitted to herself that she is a lesbian, but hasn’t told Jack in fear of losing him. So in order to keep him, Maya develops a plan.

When she finally admits her secret to Jack, he can’t believe it. But when Maya reveals her plan to keep them together, he sees an option, albeit a strange one, to keep them together. Her idea? To have Jack start a transformation to become a woman so they can stay together as a lesbian couple.

Out of his deep love for his girlfriend, Jack hesitantly agrees to give it a try, interested to see how far she will make him go towards becoming a woman. Will he quit before it is complete or will Maya unlock his inner sissy and complete her plan?

Follow along the story of Jack as he becomes dominated by his girlfriend and transformed into Jackie, a submissive sissy who is always eager to please his girlfriend.

Forced to be a Sissy Maid

Paul is a nervous wreck. He’s unemployed, uninsured, and has just crashed into the car of Jade Brooks, a powerful and gorgeous woman. When she learns that he has no way to pay for the damages to his car, she is forced to take him to small claims court to collect what is due.

But in court, Jade surprises everyone when she approaches the judge and convinces her to change her sentencing. Instead of demanding the money due to her from Paul, she allows Paul to work off his debt to her… as her sissy maid.

Paul is bewildered by the judge’s acceptance of this offer and begrudgingly accepts knowing he has no other way to pay off his debt to Jade. However, when Paul arrives at Jade’s apartment the next day, he soon discovers that the judge’s punishment was from the last he would receive.

Jade quickly becomes a demanding and dominating master for Paula, her new sissy maid. Follow along the story of Paul, as he adapts to his new life as a sissy maid, undergoes training, and succumbs to his mistress.

From Stepbrother to Stepsissy

Andrew has a hopeless crush on his sexy stepsister, Tracy, who loves teasing him to get whatever she wants. After she catches him wearing her clothing, she decides it is time to transform her stepbrother into her stepsissy and use him as her tool.

To accomplish this, Tracy has a plan to get Andrew to wear a chastity cage and dress up in women’s clothing under the pretense of sex. Andrew, eager to finally bed the girl he has had a crush on for years, falls for her plan and hands his stepsister the key to his chastity cage. After surrendering his key, he quickly finds out that Tracy has a lot more planned for him than he could have ever imagined and he’s powerless to stop it.

After successfully using Andrew to sign a client to a lucrative contract, Tracy ramps up her sissy training, teaching Andrew the pleasures of a sissy lifestyle. However, when she think’s he is ready for another outing with a more dominant client, she learns that Andrew has not yet committed to his sissy life and has to call for backup from Andrew’s stepmother, Rebecca.

Rebecca unveils a plan for her daughter to drain the last bits manhood out of Andrew and complete his transformation to be their sissy.

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Most Popular: Becoming a Sissy Maid

After neglecting his marriage, Brad is forced into chastity by his wife Melissa. In an effort to prove his love, Brad does everything Melissa demands, including dressing up like a French maid to clean the house. What neither of them expect is how much Brad likes it, and how badly he wants to continue being her maid.

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