Showing results by author "Phoebe Pearl" in All Categories

Jen made it in a man’s world. She married a lovely, kind, and gentle guy, and he dotes on her. She’s the top-performing stockbroker at her all-male firm, but something is missing. Sex. Greg isn’t bad in bed, but he can’t keep up with her sex drive. Control. Control is missing, too. After a strange conversation with John at a cocktail party, things change. John reveals his secret life as a dom, and Jen is hooked. What happens next transforms not only Jen’s life but Greg’s. Jen begins feminizing Greg, and life as a Mistress begins for Jen, and Greg’s life as her sissy maid and ...

Brook and Josie's marriage is stable, but their sex life has been reduced to a monotonous routine. One day, while rummaging through Brook's belongings, Josie stumbles upon a secret that ignites a fire within her - he desires to be a sissy cuckold and for his wife to feminize him. At first, Brook is hesitant and resistant to the idea, but with relentless persuasion and intense training from Josie, he slowly transforms into her devoted sissy cuckold. He serves her every whim domestically and sexually, submitting completely to her every command. Finally, after much searching, Josie finds the ...

Patty, Clover, and Raya are sorority sisters living life after college. The fun, wild times of college and men passed them by, and the reality of day-to-day living set in. Because of their experiences with shallow men, unfulfilling sex, and a deep need to get even, they have an opportunity to teach a dirty pig a lesson about what it’s like to be a woman. Danny Phoenix’s wife dumps him after she catches him crossdressing in her clothes. He wants her back and yet wants to experience being a woman. After witnessing the very public breakup of Danny and his wife at a restaurant, the three ...

Mateo was an unpopular, brilliant, but socially awkward student who didn't fit in with the typical crowd. Skinny and effeminate, he lacked the confidence to pursue romantic interests, particularly his crush, Jennifer - a gorgeous blonde cheerleader on the debate team. Mateo started a cleaning business to pay his tuition, accepting a job at Jennifer's sorority house. The sorority was holding a service auction for charity, and at the last minute, one girl offering maid services dressed as a French maid broke a leg. There's only one person who can save the auction—Mateo. The sorority sisters...

Carter has desires he thinks his wife, Ella, won't approve of. He secretly pursues his passion for being feminized during his frequent business trips. He wants to tell Ella about his desire to become her sissy. To become her cuckold. To be her sissy maid, he chickens out every time he gets the nerve. Ella fantasizes about dominating and feminizing her husband, Carter. Her urges and fantasies include bondage, feminization, humiliation, and cuckolding. Because her fantasies are extreme and she's insecure about losing Carter, she never reveals her secret. One weekend everything changed. An ...

John's secret sissy crossdresser life is just that secret! He dresses at home secretly, watches porn and masturbates. What he wants, what he craves, is to have fun with a group of horny guys. John loves being Nympha. He loves being girly, but he's never done anything sexual dressed as Nympha. So, from other crossdressers, he heard that a hotel called The Long Shaft is a great place to pursue his kinky and nasty fantasies. So, that's what he does, he rents a room and dresses, but it takes him ten Saturday nights to step out of his hotel room. When Nympha garners the courage to go out in ...

The once passionate and fulfilling sex life of husband Sterling and wife Harley has spiraled into a dull, lifeless routine. But one night, after an exhausting day at work, Sterling shocks his wife by revealing his desire to become her sissy cuckold. Though hesitant at first, Harley's inner perfectionist takes over and she eagerly sets out to feminize her husband and mold him into the ultimate sissy crossdresser. With each passing day, Harley becomes more ruthless in her forced feminization tactics as she trains, humiliates and disciplines her new sissy cuckold husband. And just when ...

Jordan Jones is a software developer with a secret. He likes to crossdress and fantasizes about wild kinky sex - public sex, humiliation, and being treated like a whore. For the most part, he can control his wild kinky sexual urges. But, dressing as Jennifer, his cross-dressing persona, he's been unable to control. He's getting married next week to a wealthy woman he loves, adores, and is his best friend. So, this is his last weekend as a bachelor, and he plans to dress as Jennifer. This is the last time he vows. His crossdresser friends, whom he plans on meeting later Friday night - doubt ...

Mr. Gay, a tenured college psychology professor, pretends he's conducting a study on sexual kinks, specifically about crossdressing and feminization. He acts like he's interviewing a stripper and dominatrix at a local bar. In reality, he's too scared to take the first step toward his secret desires to be feminized and crossdress. To talk to Kitty, he has to buy her drinks at the bar, and this causes him to get behind on his rent. Fed up with his delinquent rent, Ms. Martinez, his landlady, and a highly skilled special effects and makeup artist, plans to get her rent money and transform Mr. ...

Jake Barlowe has just won a high-profile case for the wealthiest man in the world. He should be happy, but he isn’t. He hates his client, Sebastian Oliver. He hates how he destroyed Oliver’s accuser’s reputation again. But his job as an attorney is to defend his clients, even scum like Oliver. After a night of drinking with Oliver, Barlowe leaves the party drunk and drives home. With two DUIs under his belt, he can ill afford another one, which would be a felony and possibly send him to prison. On his way home, he’s pulled over by Sheriff Avery, the sister of the woman Oliver ...

Alex loses a poker hand and is Forced To Crossdress. Ava, Sophia, Rose, and Olivia Feminize Alex. After Forced Feminization, Alex becomes Sophia's Sissy in Pink. Next comes a trip to the nightclub where Alex, now a Sissy Crossdresser, gets all the action he can handle. He dives right into Public Sex, Group Sex, and although he considers himself straight, he experiences sex with other men for the first time.

Howie is on the verge of marrying Abbey, the girl of his dreams. But, he’s got some concerns about her past. Abbey’s hiding something, but neither the family attorney, Josh, nor Howie knows how big the surprise is. Abbey refuses to have sex with Howie until there married. So, Howie waited, thinking it was virtuous. Howie waited patiently because he loved Abbey and enjoyed her friendship. It was a long wait, but that wait was finally over. Now, in a secluded beachfront cottage, Howie gets down to business. On their first night alone, Howie discovers the one thing Abbey forgot to mention,...

We both had the same motto: Looking for a few good men. My Marine brother-in-law forced me not only to crossdress but serve my country. Serving my country meant serving the Marines. It only took a gentle nudge to get me feminized and a little help from one of his female platoon sergeants. She transformed me from an insecure, effeminate man into a beautiful female. But there'd be a price for my female-to-male transformation. It was a small price to pay to be a woman for a night. But that night turned out to be a very long, intense night filled with taboo sex. If you love female-to-male ...

Ms. Shultz was a striking figure, standing tall and commanding in her role as a Transgender Domme. She exuded confidence and power, with a subtle hint of mischief in her eyes. Her specialty was training Sissy Crossdressers, a fact that both intrigued and intimidated Todd. For years, he had secretly dreamed of embracing his femme side and indulging in the world of sissification. But it wasn't until he met Ms. Shultz that he found the courage to take the first step towards fulfilling those desires. As Ms. Shultz led him down the path of transformation, Todd began to shed his old identity and ...

I knew I should’ve left my boss’s wife alone, but it seemed like a good idea at the time. Her nice firm behind begging to be used. Four months later, I’m on the verge of bankruptcy. My house and car are going to be repossessed, and I’m getting harassed by bill collectors. Finding a job shouldn’t be a problem; I’m one of the best copywriters in the state. There’s only one job offer, but it requires a commitment that requires humiliating lifestyle changes. My new boss asked me to be a girl, not only dress like one but do all the sexual things a girl would do. I take on my male-...

Robert Johnson is an alpha male. A hard-working, successful business and corporate attorney. His client list comprises some of the world's wealthiest and most famous business clients. He works hard and plays hard, especially with women. His wife knows full well that he cheats on her. So do most of his clients, and as far as they are concerned, it's okay. It's part of being an alpha male. His clients ignore his infidelities because he saves them millions. Betty ignores them because she was raised to believe the man is the final word in the house and that divorce is a sin. Robert has a secret...

"Passion ignites into a taboo dagger of submission, cutting through all barriers to exact justice." Tom is a junior struggling to balance journalism school, rent, and his inner demons. One day, while working as a janitor at his Pulitzer Prize-winning idol's office, Ms. Sanchez offers Tom a chance to use his writing skills and go undercover for a big story. The catch? He must completely shed his masculinity and enter Miss Gigi's sissy training center. Undergoing intense training at Miss Gigi's Sissy Training Center, Mistress Gigi and her sissies transform Tom into Ivy Li. Tom's masculinity ...

It should have been an easy job. In and out. I’ve never served time or convicted because I’m a professional. But something about watching the owner of the largest Adult store in the country: Kink Addiction, excited me. When I passed a mannequin displaying sissy clothes, I had an idea. Leave a little surprise behind. Naked except for a pair of sissy panties, stroking my erection, the owner returned. Mistress Ginger catches me red-handed, or cock in hand would be a better portrayal. Forgetting about the backpack full of cash, jewels, and other valuables, the broken door, and that I’m in...

In the heart of the city, Lark Lanza found himself entangled in a web of debts and desperation. A smooth-talking, self-assured man who ran a call center, Lark's penchant for high-stakes gambling had landed him in hot water with a ruthless loan shark. Despite receiving a sizable performance bonus, he foolishly squandered it on a "sure bet" that went awry, leaving him scrambling to placate his creditors. Left with little choice, Lark agreed to Max's, the shylock's terms, feminization and assisted her in her unique brand of collecting debts. He surrendered his manhood and the key to the ...

It should have been an easy job. In and out. I’ve never served time or convicted because I’m a professional. But something about watching the owner of the largest Adult store in the country: Kink Addiction, excited me. When I passed a mannequin displaying sissy clothes, I had an idea. Leave a little surprise behind. Naked except for a pair of sissy panties, stroking my erection, the owner returned and caught me red-handed, or maybe cock in hand would be a better portrayal. Forgetting about the backpack full of cash, jewels, and other valuables, the broken door, and that I’m in her ...