Showing results by author "Phoebe Pearl" in All Categories

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...

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 ...

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.

Cy, a successful and powerful corporate attorney, has a weak spot for her husband, Paul. She’d never let anyone at work or anywhere else run over her like she lets Paul. Cy can’t figure out why. He doesn’t work anymore. He doesn’t clean or make love to her like she wants. Cy tells herself one day, things will change. She thinks about cheating and finding an alpha male, which Paul is not. But there’s that weak spot she has for him. She considers divorcing him, but her moral character won’t allow that. She’s going out of her mind for good, mind-blowing affection when she meets a...

Todd has tried to keep his sissy crossdressing fantasies and desires secret. Though he works for a legitimate brokerage, his only client is a criminal. Todd launders money for a criminal enterprise that runs illegal gambling houses and whorehouses. If his boss, a self-described lady's man, or the criminal overlord found out about Todd's secret, it wouldn't be good. Not only would he lose his job, but the substantial gambling debt he'd accumulated would be immediately due. Fat Tony, the owner of the illegal establishments, might even decide to end Todd's life. When Todd's boss dies and ...

Taylor is very effeminate, but his domineering wife, Harper, likes it that way. Harper discovers Taylor Taylor's obsession with cross-dressing and decides to spice up their boring sex life. Harper demands that Taylor crossdress for her, become her sissy, and wear a cock cage giving her the control she desires. Harper learns about Femdom as she plans an exotic vacation. Taylor reluctantly allows Harper to crossdress him and go out for a night on the town. They meet up with three guys, and the night of wild, kinky sex transforms their dull relationship into something that would work in a porn...

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. When 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.

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.

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 ...

Henry wants to be Hazel full time, his cross-dressing other half. Hazel wants to break free from her monotonous routine: dressing up to kill on Saturday night, trolling the trans pickup apps, and being disappointed. The guys this Saturday night are driving her insane with shallow, monotonous questions. She wants, no needs sexual satisfaction, but she knows she’s not getting it from any of these guys. One guy asks what are you looking for? She responds: A knight in shining armor. Frustrated and thinking it might be a good joke, she updated her profile. She runs in her new white booty ...

Oscar Yarrow is a Sissy Crossdresser who desires to meet a dominant woman and become her sissy cuckold. He meets a sophisticated woman and joins her, Sissy Cuckold Harem. His Sissy Training is rigorous. Can he become the Sissy Cuckold she desires?

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, ...

In this femdom romance novella, a retired dominatrix decides she needs a husband. But not just any husband, a sissy cuckold. She finds it in her college-aged renter. Margie made a fortune as a dominatrix. When she made enough from humiliating men, she started her beauty studio, Makeup Maven, and semi-retired from training sissies. Margie has to be the best and wants the best. When she began her beauty studio, she only hired the best artists. Her equipment was the best. When she decided she wanted a husband, she decided he would be the best sissy cuckold on the planet. Trinity, a college ...

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...

Sterling, the husband, and Harley, the wife's sex life, have seen better days. One night after work, Sterling proposes he wants to be Harley's sissy cuckold husband. Harley agrees, reluctantly at first. As a perfectionist, she wants to feminize her man and make him the best sissy crossdresser ever. Harley begins her forced feminization of Sterling and begins to train, humiliate and discipline her new sissy cuckold husband. Harley starts a game with his new Sissy: A Cuckold Delight. Harley wants Sterling to arrange a gangbang, or he won't be set free from his cock cage.

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, ...

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 ...

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 ...

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...

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 ...