Showing results by author "Phoebe Pearl" in All Categories

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 ...

Clover Fitch is a Dominant Shemale. She is a successful businesswoman who designs sissy and cuckold clothing and accessories. She loves to train Sissies and Cuckolds. She recruits Aiden to be her accountant and Sissy Cuckold. She has monthly reviews for all her Sissy Cuckolds. Will Aiden please his new boss? This includes: Forced crossdressing, caught crossdressing, male chastity, group sex, sissy humiliation and Femdom training.

Cole acts like an alpha male and treats his wife, Grace as if he owns her. He has a secret, however. He likes to crossdress and secretly wishes to be her sissy cuckold. He secretly cross-dresses until Grace catches him dressed in her panties one day. His secret is out. Grace is unsatisfied sexually. Cole's penis is small, and his lovemaking abilities are lacking. After catching him in her panties, very aroused, she intends to end the marriage. But her lawyer has another idea-feminize him and turn him into her sissy cuckold. This story includes: caught crossdressing, sissy cuckold husband, ...

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.

Owen Jones is the most capable financial investor in the country—as long as he’s wearing Dasha Cavendish’s panties, his boss’s wife. When Quincy Cavendish catches Owen in a compromising position with his wife. Not only is he screwing her, but he’s wearing lingerie. Owen gets fired. His life spirals out of control. He’s broke. Nowhere to turn he receives a Tantalizing Proposition. One he can’t refuse. An offer that will allow him to unleash his potential as a financial investor but unveil his true inner nature as a sissy.

Angel is a cop. Angel crossdresses in secret. Angel only dresses privately, at home, and in slutty, revealing clothes. Pretending to be a slut relieves the stress of the streets. Saturday night is Angel the sluts night, when Jessica, his girlfriend, goes out for a girl’s night out. He has never gone out publicly until he hears a rumor about Jessica. Angel decides to do some undercover work. He dresses as slutty as possible because his destination is a nightclub known to cater to sluts, whores, loose women, thugs, and gangsters. He knows vice has raided the club numerous times for reports ...

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 ...

Taylor's delicate features and soft mannerisms make him stand out among the crowd, but his wife Harper relishes in his femininity. She discovers Taylor's hidden desire for cross-dressing and sees it as an opportunity to spice up their monotonous sex life. With a cruel glint in her eye, Harper demands that Taylor become her sissy, dressing him in frilly lingerie and locking his manhood away in a cock cage. As she delves into the world of Femdom, Harper plans an exotic vacation where she can fully explore her newfound power over Taylor. Despite his reservations, Taylor allows himself to be ...

Never in my life would I have imagined that I’d be in a position to fulfill some of my most secret desires. Never would I have imagined that the catalyst for fulfilling my kinkiest fantasy would be my best friend's Mom, Mrs. Bourbon, the richest woman in America. Luke, My roommate had a particularly strange problem. He refused to masturbate. Six months into our four years at the strict all-male university, he’s failing every class, and struggling on the football field. He needs sexual release. I’d offer to help, but he’d never allow another guy to take care of his needs. The ...

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 ...

Eli has a very perverted habit. He strips naked and watches his neighbor, Ms. Stratford, as she stretches for her morning run. He does a little more than watch; he takes photos of her in compromising positions and masturbates each morning. Ms. Stratford is the ultimate Milf. Eli has another secret. He is obsessed with women's underwear, wearing them, and being feminized. But he can't fulfill his desires. He lives with three macho brothers, his mother, and his father. He's too scared to order panties online or purchase them in a store, fearing his secret desire to crossdress gets out. One ...

In this steamy and provocative tale, we follow Audrey and Joey as they uncover hidden and taboo desires neither thought they had: submission, dominance, feminization, chastity, and discipline. Audrey’s husband, Joey, has a secret passion for her to be more dominant in bed, and he wants to be feminized. Slowly, Audrey inches into her new role, at first finding it repulsive. Feminize my husband? Dominate him? But once she has him in chastity, she discovers how much power this gives her. It’s addictive. And she loves it. As Audrey becomes more dominant, Joey loves her more and only wants ...

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 ...

Oscar Yarrow is a timid and unassuming man who harbors a secret desire to embrace his feminine side. He yearns for the touch of a dominant woman, one who will take him under her wing and guide him on his journey towards sissification. When he meets a sophisticated and alluring woman, he can't resist joining her exclusive club known as the Sissy Cuckold Harem. The training he undergoes is intense and demanding, but Oscar is determined to prove himself worthy of being the perfect Sissy Cuckold for his Mistress. With each passing day, he begins to shed his old identity and fully embrace his ...

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 ...

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,...

Liv, my girlfriend of five years, planned our European vacation all year. We traveled through Europe for two weeks, made love, and had a great time. When we checked into a hotel in Amsterdam, things changed. Liv was always bossy and demanding, but her demands became well freaky. Insisting we watch porn before sex. Not just any porn. But cuckold porn. Caged sissy crossdressers dressed in skimpy schoolgirl outfits were her particular kink. I developed a problem getting an erection as she humiliated me verbally. When I caught her with a guy, I left. Liv left, too, taking my wallet, cash, ...

Adam Knight had it all: a high-paying job in investment banking, an expensive home in an exclusive neighborhood, and a luxury car—all that didn’t satisfy his one need. Every Friday night, Adam becomes Amanda. At first, crossdressing was enough. It isn’t enough anymore for Amanda; she craves to flaunt all the effort, money, and practice she puts into creating her feminine persona. Crossdressing at home, showing off on hookup apps, and hooking up with guys on those apps no longer satisfied her. Amanda needs more. Craves more. Not only size-wise but intensity-wise. Amanda needs to go ...

Jaxon clenched his fists as he stepped out of the police car and into the cold, harsh light of the station. Another fight, another arrest. His stepmother's voice echoed in his head, preaching about how girls don't fight and are easier to raise. Navy, his wicked stepmom, had agreed to an anger management program suggested by Jaxon's attorney to get the assault charges dropped. Reluctantly, Jaxon entered the program, not knowing what to expect. As he entered the program, Jaxon was met with a heavy emphasis on feminization—from the pink walls and flowery decor to the gentle, soothing voices ...

Book Three of the series: Demoted To Sissy Cuckold picks up where Book Two, Clean Up Duty, Left off. Carter and Ella return home from a sex-filled and role-changing weekend. Carter is on his way to becoming the sissy cuckold he secretly dreamed of, and Ella is settling into her desire to feminize Carter. Ella wastes no time when the arrive home. She begins her home study SissyBootCamp course. Humiliating and nibbling down on Carter's manhood, turning him into the sissy she desires. Ella trains her new sissy on his new duties as a sissy maid. While feminizing Carter, she edges him all day, ...