The latest releases from Tiffany Chastain! To keep up-to-date, make sure to follow her Amazon Author Page and sign up for her Newsletter.
Sissy Study Buddies Part 4: Earning Extra Credit
Robby is loving his life with Drew, especially when he is dressed up as Robin. Whenever he’s home he’s always dolled up in his sexiest dresses and lingerie and loving how feminine and womanly he’s beginning to feel. But to the outside world he’s still Robby and that’s starting to cause conflicts.
Robby’s desire to stay as Robin is interfering with going to class. He no longer want’s to dress in men’s clothes or pretend to be someone he’s not. Because of this, his grades are starting to drop and he’s close to failing an important class. As the semester winds down and the realization of his failures is dawns on him, Robby is forced to come up with a desperate plan to fix his grades.
A plan to seduce his teacher.
Sissy Study Buddies Part 3: Sissy Shopping Spree
Things are heating up between Robby and Drew now that they feel the freedom to explore their desires for one another. Between that and unleashing their lust for dressing in women’s clothing, the two of them are living in their own world of passion and pleasure within their small school dorm.
But after months of wearing the same clothes over and over, Robby decides that it’s time for something new. It’s time for the world to meet Robin and Daisy as they go out for the first time to shop for more sexy clothes. When Drew hesitates, Robby encourages him with a deal; if Drew goes out with him, then they will do anything he wishes when they come home.
Drew gleefully agrees, already knowing exactly what he wants to do to Robby. Drew plans to make him feel more like a woman than Robby could ever believe possible.
My New Job as a Sissy Maid: The Complete Series
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.
Sissy Study Buddies Part 2: Back to School
After a long summer apart, Robby and Drew are finally heading back to the dorms for a fresh semester at college. Robby is especially excited to see Drew after fantasizing about what they might do together all summer. Including what they might wear together.
But when Drew gives Robby news that spoils their homecoming, tension builds between the two friends. Even so, Robby holds on to hope that things might once again ignite between them and waits patiently for his opportunity. When that moment finally comes, not even he can believe what he does to try to win Drew back.
Sissy Study Buddies Part 1: First Time Feminization
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 Part 4: Wedding Day
Today is the day, Heather’s wedding day. It signifies the final day of Miles’ role as her bridesmaid, Megan. However, as emotions run high and Miles ponders his future now that Heather is married, a power struggle emerges between him and his stepsister.
To settle matters between them, Heather issues Miles an ultimatum, one that will define his future. Will he take back the keys to his chastity cage or embrace his destiny, remaining under his stepsister’s control as Megan?
My Stepsister’s Sissy Bridesmaid Part 3: Bachelorette Party
After enduring over two months locked in a chastity cage and fully embracing his role as Megan, one of his stepsister Heather’s bridesmaids, Miles hits a significant milestone—Heather’s bachelorette party.
Heather once again works her magic to transform Miles into Megan, getting her all dolled up for the night’s festivities at District 5, an exclusive downtown club. It’s here that Megan will finally meet Heather’s other bridesmaids and attempt to blend in as one of the girls.
As the night unfolds, fueled by a bit of alcohol and the pulsating music on the dance floor, Megan experiences an unexpected twist—she discovers just how appealing she has become and relishes the thrilling sensation of being a sexy woman in the vibrant club scene. But just how far will she take her role as Megan?
My Stepsister’s Sissy Bridesmaid Part 2: Dress Shopping
Now that Miles has agreed to be ones of his stepsister Heather’s bridesmaids, it’s time for him to start acting the part. So when Heather needs someone to accompany her to her wedding dress fitting, she taps Miles for that role. Only now, Miles will be dressed and made up as Megan.
Heather once again feminizes and dresses her stepbrother up in her clothing and prepares him to go out in public for the first time as a woman. But that’s not all. Heather has some new ideas up her sleeves to help better control Miles and make sure he’s a good girl for her.
And that’s not all. Heather has a few extra surprises left for her stepbrother once she has him out as Megan for the first time.
From Intern to Sissy Secretary: The Complete Series
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.
My Stepsister’s Sissy Bridesmaid Part 1: Feminized
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 Part 4: Promoted to Cockold
After experiencing true pleasure at the hands of his dominant wife Anna, James is all in with his new life after agreeing to be her forever sissy. But what James doesn’t realize is that when he made such an agreement, it came with certain implications.
While he still has plenty of avenues for pleasure, with his chastity cage sworn to never be removed, his dear wife Anna is now lacking in options. When her needs become desperate, she decides it’s time to made another change in their relationship.
She decides to go find a new man, a real man, to satisfy her womanly needs.
My New Job as a Sissy Maid Part 3: New Desires
Nearly a month has passed and James is still locked in his chastity cage and still required to dress up as a maid everyday for his wife, Anna. As each day passes, he grows even more pent up with sexual energy. A sexual energy that is looking for any way to get out.
When Anna suspiciously leaves for work late one day, James can’t help but try to discover the reason why. Soon he stumbles upon one of his wife’s sexy toys left in their bed and the sight hits him with a whole new array of sensual desires. Desires that will open a door to a path he never knew existed.
Will he regret his discovery? Or will he long to further explore this new path that he has discovered?
Paperback: 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.
My New Job as a Sissy Maid Part 2: A Good Maid’s Reward
As the days go by locked in a chastity cage, James is quickly growing more interested in his wife Anna’s desires for him to be her maid. So much so that he can’t resist wearing her panties every day while she’s at work, longing to experience what he felt the first time she dressed him up.
When the weekend comes around she offers him a chance to earn his release from his cage if he obeys her every command for the entire day, he quickly jumps at the opportunity. But what he doesn’t realize is Anna’s intentions to feminize him into a more proper maid and make his new job full-time.
James obey’s her every command in hopes of a reward, but what is a proper reward for a good maid? He will soon find out.
Sissy’s First Date: The Complete Series
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.
My New Job as a Sissy Maid Part 1: Hired as Her 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.
From Intern to Sissy Secretary Part 4: Secretarial Duties
Jacob’s newfound desires are fueling his passion for his job more than ever. His eagerness to satisfy his boss, Victoria, is also growing while she continues to hold the key to not only his chastity cage, but his pleasure. Luckily for him, Victoria has developed a fresh batch of kinky toys for him to try out, promising to fulfill his deepest desires.
However, Jacob’s desires go beyond just toys. He yearns for more.
Soon, as complications arise between his company and Roger’s, he sees his chance—not only to fulfill his cravings but also to prove to Victoria that he can be the obedient sissy she desires.
From Intern to Sissy Secretary Part 3: Sissy Plaything
Jacob has officially taken the plunge into his new role as the sissy secretary, working under the formidable Victoria. But this isn’t the old Jacob anymore. The sign on his desk spells out “Jenny” now, and he’s got a daily dress code that involves embracing his feminine side. The longer he spends locked in his chastity cage, the more he finds himself enjoying this fresh identity and lifestyle.
Yet, things shift gears when an unexpected package arrives and Victoria requests him in her office to discuss it. She’s got news about a shipment of new products from Roger and suggests they put them to the test — together. Little does Jacob realize, there’s a hidden agenda at play. Victoria has plans to transform him into her personal sissy plaything, using him as a canvas to try out all her new toys.
Paperback: 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.
Becoming a Sissy Maid: Unlocking Hidden Desires
After allowing his marriage grow stagnant, Brad is faced with a tough decision. Wear a chastity cage or lose his relationship with his wife, Melissa. Melissa has issued him this ultimatum after years of growing unhappy in their marriage and because she believes that wearing a chastity cage will help turn Brad back into the loving, supportive man she married.
When Brad agrees, Melissa begins to give him daily chastity chores. Motivated by his desire to prove his devotion to his wife, Brad performs his chores diligently even as Melissa begins to add to his list of chastity chores. To further test his love and growing obedience, Melissa decides to tell him to dress up like a French maid for a deep cleaning of the house. When Brad not only agrees but seems eager to dress up again, Melissa understands that Brad was meant for a different life and takes it upon herself to unlock his hidden desires.
From Intern to Sissy Secretary Part 2: First Time Sissy
Now that Jacob’s under lock and key in a chastity cage by his boss, Victoria, he’s quickly becoming her personal experiment. And to further her experiment, she’s now requiring him to wear bras and panties to work every day.
While Jacob is adjusting to his new clothing and the new desires that result from wearing sexy lingerie in public, Victoria is making other plans for him. When Victoria’s secretary, Sarah, goes on leave, an unexpected job opening pops up. Victoria sees an opportunity and believes Jacob’s the perfect fit. However, there’s a catch: she wants him to step into the role of Sarah, not himself.
From Intern to Sissy Secretary Part 1: Caged & Dominated
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.
Amidst a 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. But, as events unfold, he’s about to get an eye-opening revelation.
Feminization Camp: The Complete Series
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.
Blackmailed Sissy Maid: The Complete Series on Paperback
Now in Paperback!
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.
Sissy’s First Date Part 4: Date Night
As time goes on, Ben remains locked in a chastity cage by his friend Olivia. She’s determined to transform him into her new friend, Becca, giving him a taste of online dating from a woman’s perspective. Every day, he’s tasked with dressing up as Becca and chatting with men Olivia selects on the dating site.
However, Olivia has a surprise up her sleeve. She plans to reenact one of her past dates that didn’t go well, but with a twist: she’ll be the man, and Ben will play the girl. This pretend date is designed to push Ben out of his comfort zone and help him understand the new desires he’s experiencing. But how far is Ben willing to go as Becca?
Sissy’s First Date Part 3: The Practice Date
As time goes on, Ben remains locked in a chastity cage by his friend Olivia. She’s determined to transform him into her new friend, Becca, giving him a taste of online dating from a woman’s perspective. Every day, he’s tasked with dressing up as Becca and chatting with men Olivia selects on the dating site.
However, Olivia has a surprise up her sleeve. She plans to reenact one of her past dates that didn’t go well, but with a twist: she’ll be the man, and Ben will play the girl. This pretend date is designed to push Ben out of his comfort zone and help him understand the new desires he’s experiencing. But how far is Ben willing to go as Becca?
Sissy’s First Date Part 2: Becoming Becca
After a week in a chastity cage, Ben is starting to grasp his new place in life under Olivia’s control. Despite wanting his cage key back, her charm and power make it tough for him to deny her ownership of it.
This suits Olivia’s plans perfectly. She’s set on fully transforming Ben into her sissy, and this time she’s taking things up a notch, pushing him past his limits into a whole new world. A world where he’s known as Becca.
Olivia keeps Ben browsing dating sites as Becca and messaging men. It’s all part of her plan to guide him toward his first sissy date, which will be the ultimate step in his transformation journey.
Sissy’s First Date Part 1: Truth or Dare
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 first story of Ben’s tale of transformation as Olivia begins her plan. A plan that will soon turn him from single man to a sissy with a date.
Feminized By My Best Friend: The Complete Series
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.
Looking for More Stories?
For more of Tiffany Chastain’s books and short stories, check out the following links!