Showing results by author "Phoebe Pearl" in All Categories

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 ...

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 ...

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 ...

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, ...

Jason is an effeminate man. He is a fish out of water at Dream Body, the gym where Becky, the woman he has been infatuated with, works as a personal trainer. He joined the gym, hoping to impress Becky and gain her attention by bulking up. In the public eye, Becky is presented as someone who only dates strong, macho men. However, in private, she has a hidden attraction to delicate, submissive, effeminate men like Jason. Jason tirelessly works out for six months, hoping to catch Becky's eye. But despite his efforts, she remains oblivious to him. In a last-ditch effort, Jason schedules a ...

Five Star Sissy is a sex-packed, transgender erotica novella. Sage fantasizes about cross-dressing daily. Perhaps it's more of an obsession. But Sage can't seem to cross that threshold and dress however she wants. That is until one night; she gets caught crossdressing. Mrs. Jacobs, a transgender woman, begins Sage's feminization with the help of a cheerleader named Grace. Sage is a reluctant crossdresser at first. But, as she settles into her new persona, she becomes more confident. Not only does Sage want to crossdress, but Sage wants to be a slut.

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 ...

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 ...

Lilly is restless and dissatisfied. She craves sexual fulfillment, but her husband Ollie seems distant during their lovemaking. Is he preoccupied with work, making money, or playing golf? Lilly is shocked when Ollie hires her old friend Nova, who happens to be a dominatrix, for some kinky play. As they delve into their sessions, Lilly uncovers a secret about Ollie: he enjoys wearing women's panties and being humiliated. This revelation angers Lilly and she considers divorcing him or ruining him in revenge. However, Nova, being the creative dominatrix that she is, comes up with an idea to ...

Keith Montgomery was a ghost on his college campus, blending into the background with ease. But one chance encounter with a mysterious female basketball phenomenon changed everything. In a moment of impulsiveness, Keith stole her panties and set off a chain of events that would turn his life upside down. Briana Jacobs, known as the muscular lesbian Goddess on campus, vowed to seek vengeance upon the culprit who dared to humiliate her. When she discovers that Keith is responsible for the theft, she wastes no time setting her plan into motion. She traps him in a web of Femdom dominance, ...

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 ...

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, ...

Jaxon gets into another fight and is arrested. His stepmother believes girls don't fight and are easier to raise. Navy, Jaxon's wicked stepmom, agrees to an anger management program suggested by Jaxon's attorney to get the assault charges dropped. Jaxon enters her anger management program, which is heavy on feminization.

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 ...

Delving into the dark depths of dominance and submission, a twisted tale of feminization and insatiable desire unfolds between Bridgette and Benjamin. Bridgette struggles to find and effeminate a man who suits her needs. Benjamin struggles with his secret fetish—woman’s panties. After an accident, a fender bender brings the two together. Benjamin surrenders to the intoxicating rush of submitting to Bridgette’s will. Bridgette has her man until he’s no longer a man but a sissy. Her sissy.

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 ...

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 ...

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.

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 ...

Frank is a successful millionaire known for his exquisite antique store. But behind closed doors, he struggles with feelings of inadequacy in the bedroom and a need to be controlled—something he has never revealed. Monica, Franks's wife, designs a plan to assert her power over him through feminization and chastity using Femdom. At first hesitant, Frank eventually succumbs to Monica's wishes and transforms into Kitty under her vigilant eye. As Monica delves deeper into her newfound dominance, she decides to add chastity to the mix, subjecting Kitty to thirty days of agonizing Locktober ...