
Sissy for the Strict Headmistress
Femdom Feminization, Book 1
Failed to add items
Add to Cart failed.
Add to Wish List failed.
Remove from wishlist failed.
Adding to library failed
Follow podcast failed
Unfollow podcast failed

Get 2 free audiobooks during trial.
Buy for $6.95
No default payment method selected.
We are sorry. We are not allowed to sell this product with the selected payment method
-
Narrated by:
-
Razor After Dark
-
By:
-
Charlie Quinn
About this listen
When burly tradesman Tyler finds some women’s clothes hidden away at the empty school he’s working on, he can’t resist exploring his secret sissy fantasies. But the strict Headmistress catches him in the act and punishes him in a most unexpected way–forced to fully feminize, he is spanked over her desk and made to satisfy both her and himself. But who’s enjoying it more–the hot but stern Headmistress, or big, butch Tyler, all dressed up as a girl?
12,000 word story with sissy feminization, CFNM, erotic humiliation, a submissive male and a very dominant woman. Enjoy as a standalone novella or listen as part of the 'Femdom Feminization' series.
©2021 Charlie Quinn (P)2024 Charlie QuinnListeners also enjoyed...
-
Mistress Peggy and the Stag Night Submission
- The Femdom Conspiracy, Book 1
- By: Charlie Quinn
- Narrated by: Tadd Morgan
- Length: 1 hr and 13 mins
- Unabridged
-
Overall
-
Performance
-
Story
“I’m Peggy by name and Peggy by nature,” the dominatrix said as she bent him over. Darren looked up at the sexy yet terrifying woman who towered over him in her thigh-high leather boots. How on earth had his bachelor party stag night ended up like this? And was he really going to submit and let her do that to him?
By: Charlie Quinn
-
Obey Her
- Extreme Office Femdom: She's the Boss, Book 1
- By: Charlie Quinn
- Narrated by: Smokey Patton
- Length: 56 mins
- Unabridged
-
Overall
-
Performance
-
Story
When Connor starts a new job, he's pleased to find he's the only male in an office full of attractive women. But then he starts getting mysterious, anonymous messages telling him to do some very taboo things. Intrigued, he follows the instructions....
By: Charlie Quinn
-
Cuffed and Caged
- Femdom and Male Chastity, Book 1
- By: Charlie Quinn
- Narrated by: David Piper
- Length: 1 hr and 42 mins
- Unabridged
-
Overall
-
Performance
-
Story
A disastrous first attempt at femdom leaves Jonathan bruised and humiliated, and he’s at rock bottom. Then, sexy, sophisticated, and wealthy Mrs. Cavendish comes to his rescue and promises to make everything all right again - at a hefty price. She demands total obedience and utter control over him.
-
-
very hot
- By Stephen Perry on 07-08-24
By: Charlie Quinn
-
A Brother Becomes a Sister
- An LGBT, New Adult, First Time, Short-Read Romance
- By: Barbara Deloto, Thomas Newgen
- Narrated by: Ruby Rivers
- Length: 2 hrs and 25 mins
- Unabridged
-
Overall
-
Performance
-
Story
Toni’s twin brother Riley has just graduated from art school, and Toni invites Riley to live with her in California until he can find a good job. Toni has always wanted a sister, and Riley has always been a bit of a femboy anyway, so Toni puts her plan into action. She manages to enlighten Riley about the nuances of presenting his feminine side and immerses him in the pleasures of catering to his feminine persona.
-
-
So romantic
- By Elinor Scott-Lester on 12-22-24
By: Barbara Deloto, and others
-
Feminized by Her
- A College Student Falls in Love With the Girl Who Crossdresses Him
- By: Barbara Deloto, Thomas Newgen
- Narrated by: Ruby Rivers
- Length: 1 hr and 50 mins
- Unabridged
-
Overall
-
Performance
-
Story
A geek named Joss, working on his PhD thesis on motivation, rents a house away from the noise and takes in a roommate named Marcy to help pay the bills. Little does he know how lucky he will be to have Marcy as his roommate. She is another PhD candidate, also working on a thesis about motivation. Gorgeous and intelligent, Marcy motivates Joss to discover things he never would have dreamed of, and they learn about motivation, love, sensuality, and femininity. She soon has Joss fully crossdressed and feminized to experience life as Jossie, a desirable girl rather than his geek self.
-
-
Fantasy
- By gh on 08-08-20
By: Barbara Deloto, and others
-
Becoming a Sissy Maid
- Unlocking Hidden Desires
- By: Tiffany Chastain
- Narrated by: Gabrielle Ash
- Length: 3 hrs and 19 mins
- Unabridged
-
Overall
-
Performance
-
Story
After allowing his marriage to 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.
-
-
Good Story - Dislike One Character
- By JJarvis on 09-10-24
By: Tiffany Chastain
-
Mistress Peggy and the Stag Night Submission
- The Femdom Conspiracy, Book 1
- By: Charlie Quinn
- Narrated by: Tadd Morgan
- Length: 1 hr and 13 mins
- Unabridged
-
Overall
-
Performance
-
Story
“I’m Peggy by name and Peggy by nature,” the dominatrix said as she bent him over. Darren looked up at the sexy yet terrifying woman who towered over him in her thigh-high leather boots. How on earth had his bachelor party stag night ended up like this? And was he really going to submit and let her do that to him?
By: Charlie Quinn
-
Obey Her
- Extreme Office Femdom: She's the Boss, Book 1
- By: Charlie Quinn
- Narrated by: Smokey Patton
- Length: 56 mins
- Unabridged
-
Overall
-
Performance
-
Story
When Connor starts a new job, he's pleased to find he's the only male in an office full of attractive women. But then he starts getting mysterious, anonymous messages telling him to do some very taboo things. Intrigued, he follows the instructions....
By: Charlie Quinn
-
Cuffed and Caged
- Femdom and Male Chastity, Book 1
- By: Charlie Quinn
- Narrated by: David Piper
- Length: 1 hr and 42 mins
- Unabridged
-
Overall
-
Performance
-
Story
A disastrous first attempt at femdom leaves Jonathan bruised and humiliated, and he’s at rock bottom. Then, sexy, sophisticated, and wealthy Mrs. Cavendish comes to his rescue and promises to make everything all right again - at a hefty price. She demands total obedience and utter control over him.
-
-
very hot
- By Stephen Perry on 07-08-24
By: Charlie Quinn
-
A Brother Becomes a Sister
- An LGBT, New Adult, First Time, Short-Read Romance
- By: Barbara Deloto, Thomas Newgen
- Narrated by: Ruby Rivers
- Length: 2 hrs and 25 mins
- Unabridged
-
Overall
-
Performance
-
Story
Toni’s twin brother Riley has just graduated from art school, and Toni invites Riley to live with her in California until he can find a good job. Toni has always wanted a sister, and Riley has always been a bit of a femboy anyway, so Toni puts her plan into action. She manages to enlighten Riley about the nuances of presenting his feminine side and immerses him in the pleasures of catering to his feminine persona.
-
-
So romantic
- By Elinor Scott-Lester on 12-22-24
By: Barbara Deloto, and others
-
Feminized by Her
- A College Student Falls in Love With the Girl Who Crossdresses Him
- By: Barbara Deloto, Thomas Newgen
- Narrated by: Ruby Rivers
- Length: 1 hr and 50 mins
- Unabridged
-
Overall
-
Performance
-
Story
A geek named Joss, working on his PhD thesis on motivation, rents a house away from the noise and takes in a roommate named Marcy to help pay the bills. Little does he know how lucky he will be to have Marcy as his roommate. She is another PhD candidate, also working on a thesis about motivation. Gorgeous and intelligent, Marcy motivates Joss to discover things he never would have dreamed of, and they learn about motivation, love, sensuality, and femininity. She soon has Joss fully crossdressed and feminized to experience life as Jossie, a desirable girl rather than his geek self.
-
-
Fantasy
- By gh on 08-08-20
By: Barbara Deloto, and others
-
Becoming a Sissy Maid
- Unlocking Hidden Desires
- By: Tiffany Chastain
- Narrated by: Gabrielle Ash
- Length: 3 hrs and 19 mins
- Unabridged
-
Overall
-
Performance
-
Story
After allowing his marriage to 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.
-
-
Good Story - Dislike One Character
- By JJarvis on 09-10-24
By: Tiffany Chastain
-
Worship Her
- Extreme Office Femdom: She's the Boss, Book 4
- By: Charlie Quinn
- Narrated by: Jonny Wonderland
- Length: 1 hr and 10 mins
- Unabridged
-
Overall
-
Performance
-
Story
The mystery of the femdom office continues as Connor is trained as the submissive, sissified office toy. Under her desk, Connor must show his absolute devotion to his demanding Mistress and the other women, as they torment and use him at work. To keep him in line, his dominant Mistress places him in male chastity, further controlling him with tease and denial and ensuring that he can only find satisfaction at her command.
By: Charlie Quinn
-
The Secretary's Key
- By: Anna Ritter
- Narrated by: Liv Watkins
- Length: 1 hr and 17 mins
- Unabridged
-
Overall
-
Performance
-
Story
Keys are important. They open doors, but they can also close locks. Andrew is acutely aware of how powerful they can be. Yes, he might control of his company and employees, but that might change. As the sole owner of his company, he has numerous subordinates, including his secretary, but he has a secret. He enjoys playing around with a chastity belt. He puts it on to sharpen his focus and heighten his determination. But right after finishing with a giant deal, he decides to let himself out for a little while to have some fun.
-
-
hot and arousing femdom erotica
- By Paul Weimer on 02-09-21
By: Anna Ritter
-
Her Gift to Him: An LGBT, First Time, Feminization, New Adult, Transgender Romance
- By: Barbara Deloto, Thomas Newgen
- Narrated by: Ruby Rivers
- Length: 1 hr and 43 mins
- Unabridged
-
Overall
-
Performance
-
Story
It’s Christmas break. Gorgeous Piper loves nerdy Jake’s passion for buying her clothes, but her intuition tells her he does it not only because he loves her so much but also because of his hidden desire to wear them himself. She buys her love everything needed for crossdressing and transforming Jake into Jackie, her girlfriend. That afternoon, she enlightens him in the nuances of presenting his feminine side and immerses him in the pleasures of catering to his feminine persona.
-
-
hot and interesting but
- By WeAreAllDavis on 04-09-21
By: Barbara Deloto, and others
-
The Landlord's Doll
- Female Landlord Feminizes Male Tenant
- By: Clover Cox
- Narrated by: Virtual Voice
- Length: 1 hr and 57 mins
- Unabridged
-
Overall
-
Performance
-
Story
One man’s dream comes true by the woman he least expects. If Arnold gave up his shopping habit, he would be able to afford rent. Instead, he spends far too much money on dresses and lingerie. Margaret, Arnold’s landlady, wants her money, so she isn’t thrilled when she finds a package waiting for Arnold when she goes to check how he is doing. Arnold doesn’t want to lose his place, and he’ll do anything to keep it and stay in Margaret’s good graces. The Landlord’s Doll is a steamy feminization contemporary romance story featuring a curious man and his demanding landlady.
By: Clover Cox
-
Enslaved and Feminized by Dommes Vol. 1
- A Femdom Story of Revenge, Chastity, and Feminization
- By: PhDomme Emma
- Narrated by: PhDomme Emma
- Length: 2 hrs and 5 mins
- Unabridged
-
Overall
-
Performance
-
Story
Timothy is an ambitious young journalist working for a prestigious paper. He launched his stellar ascent to become a journalist elite with a series of articles that he acquired by blackmailing his talented former classmate, Marcel, who was having a BDSM relationship with his teacher. Marcel is now frying hamburgers to make ends meet and Timothy is not meeting expectations and struggling in his efforts to keep his new job. He needs to come up with another hot topic, or else he will be sent packing!
By: PhDomme Emma
-
Finishing School: A Boy Is Sent to a Girls' Finishing School
- An LGBT Romance
- By: Barbara Deloto, Thomas Newgen
- Narrated by: Ruby Rivers
- Length: 1 hr and 37 mins
- Unabridged
-
Overall
-
Performance
-
Story
Sam was just another lazy kid - no direction in life, hanging out at his parents’ house, no girlfriend, listless. His parents gave him choices: move out and work the only kind of job he was ready for, a minimum-wage job, or join the service, or go to a girls’ finishing school. Sam becomes Samantha and goes off to school - a school where the girls are taught how to take care of a man and be the ideal wife.
-
-
Pretty Good Story & Performance
- By Xurtch on 01-19-19
By: Barbara Deloto, and others
-
Girl Boss
- By: Alyson Belle
- Narrated by: Juliana Solo
- Length: 2 hrs and 23 mins
- Unabridged
-
Overall
-
Performance
-
Story
Harry has spent his entire career working toward his next big promotion, but on the day before his performance review, he discovers that it's going to be denied to him—the company wants a woman for the job instead. Gender diversity in management is important, but that doesn’t change the fact that Harry is crushed to lose his job and everything he's worked so hard for.
By: Alyson Belle
-
Paying My Dues
- A First-Time, Feminization, New-Adult, Short-Read, LGBT Cross-dressing Romance
- By: Barbara Deloto, Thomas Newgen
- Narrated by: Ruby Rivers
- Length: 1 hr and 30 mins
- Unabridged
-
Overall
-
Performance
-
Story
Dress like a girl to join an elite society? A master’s degree student wants to join an exclusive and elite secret society where the members network and become huge successes financially. The only problem is that he has to pay his dues first. Can he do it? Membership requirements: A good person, unbiased, non-judgmental, with no homophobic or gender-slandering tendencies. An understanding of the importance of balancing masculine and feminine energies. Dedicated to helping other members. Able to keep secrets.
-
-
fan of you audio books
- By Anonymous User on 02-20-22
By: Barbara Deloto, and others
-
Sissy Dollhouse Season One: Parts 1 - 12 in the Series
- Sissy Dollhouse Complete Seasons
- By: Jenna Masters
- Narrated by: Jessica Howard
- Length: 5 hrs and 10 mins
- Unabridged
-
Overall
-
Performance
-
Story
At the Sissy Dollhouse men are captured by the beautiful dominatrix Tanya and turned into mind controlled transgender dolls using seduction, drugs, hypnosis, surgery, and hormones; then they are used as programmable prostitutes for fulfilling the fantasies of rich clients.
-
-
What Great Stories!!!
- By John Blake on 05-08-21
By: Jenna Masters
-
Femdom: Making Him into My Sissy Slave, Erotica Sex Stories, BDSM Forced Feminization and Sissification
- By: Riley Anderson
- Narrated by: Nikie Monroe
- Length: 3 hrs and 5 mins
- Unabridged
-
Overall
-
Performance
-
Story
In this three-book bundle of some of the most electrifying BDSM, rough, submissive and humiliating sex, you will be stunned, shocked, and ultimately be left begging for even more.
-
-
Waste
- By Robert on 08-02-24
By: Riley Anderson
-
Becoming a Nurse: Feminized by My Wife
- Role Play Gender Swap, Book 1
- By: Becky Huntingdon
- Narrated by: Samantha Elizabeth
- Length: 22 mins
- Unabridged
-
Overall
-
Performance
-
Story
I've always been bored watching my girlfriend's soccer matches. After a game, she invited some of her teammates over, and they made me into a cheerleader. From a dress to pom-poms, I had to do whatever they said. This short, gender-swap role play has feminization, first-time sissy action and lots of adult fun.
-
-
Shorty
- By Boating trouble on 02-28-23
By: Becky Huntingdon
-
Dominated and Punished: By My Wife and Her Alpha MILF Lover
- The Dominated Husband, Book 1
- By: Charlie Quinn
- Narrated by: Darren Schilling
- Length: 1 hr and 11 mins
- Unabridged
-
Overall
-
Performance
-
Story
When Michael finds his wife making out with the smoking-hot MILF next door, the two women team up and take control of him. He is put in his place, spanked, feminized, and made to watch while the ladies take their pleasure. Dominated and denied satisfaction, the MILF forces him to his knees to experience a humiliating new way of gaining release.
By: Charlie Quinn