Tiffany Chastain's Blog

First off, I wanted to thank all of you for your continued support. Without you buying my stories and giving them positive reviews I would have stopped writing long ago. But with your encouragement I keep on going

Personally, 2024 was a wild year filled with many life changes, things that have altered the course of my life. True to my original book, Becoming a Sissy Maid: Unlocking Hidden Desires, I have finally quit my day job to become a full time devoted servant for my mistress. Now all day I dress in my frilly dresses, my puffy petticoats, and my highest heels to obey her every whim and command.

But don’t worry, she’s a fair and just mistress and will give me the time I need to continue writing for you — actually, she insists that I have some outlet for my pent up desires. 

She also gave me the great idea of reflecting over this last year so I could better appreciate the change that she has allowed me to make. In a similar fashion, I thought it would be a great idea to share with you all the stories I’ve written this year just in case you’ve missed anything.

Locked in servitude for one of the world’s richest and most powerful women.

Creating a special bond with your college roommate and earning special credit with professors.

Learn what it really means to be a sexy woman.

Unleash your inner femboy and embrace that special side of you.

Become your ex-wife’s sissy servant and finally treat her like the goddess she is.

Plan the perfect getaway for your mistress, and make sure she is satisfied in every way.

Become your wife’s special doll for her to practice her hair and makeup talents.

Get that promotion you’ve always wanted while discovering what you’ve always needed.

Swap gender roles with your wife by becoming the maid while she becomes the master.

Teacher and sexy student role play is even hotter when the genders are swapped.

Santa’s little helper gets a special surprise from his keyholder.

All she wants for Christmas is a strong man to pleasure her in every way that you can’t.

Being a full-time sissy maid has never been easy. It demands poise, purpose, and unwavering dedication. It thrives on desire, duty, and devotion. But above all, it requires absolute obedience.

For Zoe, however, the boundaries of her role are shifting yet again. Her life as a full-time sissy maid now comes with an unexpected twist—she’s being thrust into the role of a mistress. As she takes on the task of training Scarlett to become a proper sissy maid, emotions run high, and the once-clear lines of her identity blur, forcing Zoe to question the life she’s built.

Amid the changes, one thing becomes clear: her relationship with her wife, Melissa, must evolve yet again. But how?

Don’t miss the sexy and dramatic conclusion to the Becoming a Sissy Maid saga!

The post 2024 in Review first appeared on Tiffany Chastain.

Becoming My Mother-in-Law’s Sissy Part 1: Caged for Control is this month’s first free book!

From January 11th until January 15th, get Becoming My Mother-in-Law’s Sissy Part 1: Caged for Control for free!

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.

Becoming My Mother-in-Law’s Sissy Part 1: Caged for Control is available to read on Kindle and for free with a Kindle Unlimited membership. This story revolves around the themes of sissies and feminization.

The post January Book Giveaway first appeared on Tiffany Chastain.

Blackmailed Sissy Maid Part 1: Becoming Her Maid is this month’s first free book!

From November 16th until November 20th, get Blackmailed Sissy Maid Part 1: Becoming Her Maid for free!

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.

Blackmailed Sissy Maid Part 1: Becoming Her Maid is available to read on Kindle and for free with a Kindle Unlimited membership. This story revolves around the themes of sissy maids, femdom, and feminization.

The post November Book Giveaway #2 first appeared on Tiffany Chastain.

The Sissy Model: First Time Feminization is this month’s first free book!

From November 6th until November 10th, get The Sissy Model: First Time Feminization for free!

When Vince’s hot neighbor Cindy surprises him at his front door, begging for help, Vince thinks he finally has an in to getting into bed with her. She tells him that she needs someone to replace the model for her photo shoot which is just hours away and that she thinks he would be perfect. Vince agrees to help in trade for her owing him a favor. A favor that he hopes to make sexual.

However, what Vince doesn’t know is that Cindy doesn’t need a replacement male model. She need someone to replace her missing female model and wants Vince’s help because of his petite and feminine body.

Once Cindy has transformed and feminized Vince, he sudden comes face-to-face with his tall, handsome and muscular costar, John, and quickly finds out how willing he is to play the role of a woman.

The Sissy Model: First Time Feminization is available to read on Kindle and for free with a Kindle Unlimited membership. This story revolves around the themes of sissies and feminization.

The post November Book Giveaway first appeared on Tiffany Chastain.

Feminized By My Best Friend Part 1 & Part 2 are this month’s discounted books!

From October 24th until October 28th, get BOTH Feminized By My Best Friend Part 1 & Part 2 for only $0.99 each!

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.

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

Feminized By My Best Friend is available to read on Kindle and for free with a Kindle Unlimited membership. This story revolves around the themes of sissies, feminization, chastity, and bdsm.

The post October’s Discount Books first appeared on Tiffany Chastain.

Taken by the Wolf: A Halloween Gender Swap Story is this month’s free book!

In honor of the beginning of Locktober, Tiffany is offering her Halloween story for free for a limited time!

From October 4th (8am PDT) until October 8th (8am PDT), get Taken by the Wolf: A Halloween Gender Swap Story for free!

Scott used to be a fun, outgoing, partier, but as he’s grown older and settled into married life, things have changed. He’s no longer interested in going out or partying. And he’s certainly not interested in Halloween.

This is the complete opposite of his wife, Robin, who loves going out and loves Halloween. Luckily for her, this Halloween she has Scott locked in a chastity cage so he has to do whatever she says. When Robin tells Scott about the gender swapped couples costume they will be wearing to enter into the big costume contest, Scott is floored, but he also knows he has no choice but to agree. So Scott lets Robin feminize him and dress him up as a woman in a slutty Halloween costume.

Once they’re dressed up and at the party, Scott starts letting loose and breaking out of his shell, returning to his normal fun self. But he soon lets his guard down too much and learns what life is like for a slutty woman on Halloween. And to his surprise, he enjoys it more than he ever thought possible.

Taken by the Wolf: A Halloween Gender Swap Story is available to read on Kindle and for free with a Kindle Unlimited membership. This story revolves around the themes of sissies, feminization, chastity, and bdsm.

The post October’s Book Giveaway first appeared on Tiffany Chastain.

Taken by the Wolf: A Halloween Gender Swap Story is this month’s free book!

In honor of the beginning of Locktober, Tiffany is offering her Halloween story for free for a limited time!

From October 5th (8am PDT) until October 9th (8am PDT), get Taken by the Wolf: A Halloween Gender Swap Story for free!

Scott used to be a fun, outgoing, partier, but as he’s grown older and settled into married life, things have changed. He’s no longer interested in going out or partying. And he’s certainly not interested in Halloween.

This is the complete opposite of his wife, Robin, who loves going out and loves Halloween. Luckily for her, this Halloween she has Scott locked in a chastity cage so he has to do whatever she says. When Robin tells Scott about the gender swapped couples costume they will be wearing to enter into the big costume contest, Scott is floored, but he also knows he has no choice but to agree. So Scott lets Robin feminize him and dress him up as a woman in a slutty Halloween costume.

Once they’re dressed up and at the party, Scott starts letting loose and breaking out of his shell, returning to his normal fun self. But he soon lets his guard down too much and learns what life is like for a slutty woman on Halloween. And to his surprise, he enjoys it more than he ever thought possible.

Taken by the Wolf: A Halloween Gender Swap Story is available to read on Kindle and for free with a Kindle Unlimited membership. This story revolves around the themes of sissies, feminization, chastity, and bdsm.

The post October’s Freebie first appeared on Tiffany Chastain.

Turned Sissy By My Lesbian Girlfriend Part 1: Feminized is this month’s second discounted book!

From September 26th (8am PDT) until October 1st (8am PDT), get Turned Sissy By My Lesbian Girlfriend Part 1: Feminized for only $0.99!

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?

Turned Sissy By My Lesbian Girlfriend Part 1: Feminized is available to read on Kindle and for free with a Kindle Unlimited membership. This story revolves around the themes of sissies, feminization, chastity, and bdsm.

The post September’s Bonus Discount Book first appeared on Tiffany Chastain.

Forced to be a Sissy Maid Part 1: Sentencing is this month’s discounted book!

From September 11th (8am PDT) until September 15th (8am PDT), get Forced to be a Sissy Maid Part 1: Sentencing for only $0.99!

Paul is a nervous wreck. He’s unemployed, uninsured, and has just crashed his car 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 accepting 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.

Forced to be a Sissy Maid Part 1: Sentencing is available to read on Kindle and for free with a Kindle Unlimited membership. This story revolves around the themes of sissies, feminization, chastity, bdsm, and, of course, sissy maids.

The post September’s Discount Book first appeared on Tiffany Chastain.

Frat House Sissy Part 4: Everyone’s Girl is out today! This is the fourth and final installment of our latest sissy series.

The morning after pleasuring his best friend, Tyler, for the first time, Greg has his second day of sissy maid training. As he continues to learn the ropes of his new role in his fraternity’s house, he realizes that he has a problem. He needs to learn how to apply makeup.

With no other option, Greg has to seek out Tina, the girl who had dressed him up as a cheerleader. During that, she had feminized him and done his makeup, so Greg hopes she will be able to help. And she is, for a price.

But that’s not all for Greg’s day, when he comes home he is confronted by Tyler once again. And once again, Greg realizes that he likes being Tyler’s girl. A lot.

Frat House Sissy Part 4: Everyone’s Girl is available to read on Kindle and for free with a Kindle Unlimited membership. This story revolves around the themes of sissies, feminization, chastity, and sissy maids.

The post Frat House Sissy Part 4 first appeared on Tiffany Chastain.