Showing results by author "Phoebe Pearl" in All Categories

The journey continues in Book Two of A Steamy Sissy Scavenger Hunt. In Book One: Mistress Holly and her submissive sissy cuckold Husband, Sissy Gina, embark on an exhilarating Scavenger Hunt. Mistress Holly, with help from her sadistic mind, created the ultimate Sissy Cuckold Games and introduced Sissy Gina to new levels of submission and pleasure. Fate intervenes and introduces them to another potential sissy, Toby. Mistress Holly’s vacation takes an unexpected turn. Mistress Holly welcomes Toby into her twisted world of submission, and a transformation begins. Mistress Holly begins ...

Book four, the last book of the series picks up where book three ended. Jaxon, now simply Sissy, complained, begged, and pleaded with his stepmom for a night on the town. Dressed as a girl, of course. Navy has him complete some community service first, then has him dropped off for a night on the town. Sissy removes her blindfold and finds she's in a very unsavory location. She has a choice: one of two strip clubs, a porn shop, and an adult store. Sissy heads to the Pink Paradise, a strip club. She puts into practice all the tasks and assignments of her feminization program and is amazed at ...

Read Sissy Gina and Mistress Holly’s Journey into the Uncharted Depths of Power, Pleasure, and Taboo Desires. Sissy Gina and Mistress Holly have been husband and wife for many years now. Sissy Gina is bored with the same old sissy cuckold games and wants more adventure. Mistress Holly has perfected her sadistic talents at feminizing and dominating men. She concludes that the world has too many sissies and not enough Mistress, so she devices not only to give her sissy cuckold the adventure of a lifetime but find another sissy or two. Their journey begins with a Steamy Sissy Scavenger Hunt ...

Jace fantasizes about being forced into feminization constantly. He has urges and sexual desires he can’t control, which leads him to steal women’s panties from the cheerleader’s locker room at the stadium, where he’s a security guard. Everyone knows there’s a panty thief on the loose. Mary Jane, an especially determined cheerleader, takes action. She tapes Jace wearing her clothes while on the field, cheering the home team on to victory. With advice from the Human Sexuality professor at college, she decides to feminize Jace and make him pay in a very unusual, sexually humiliating...

In Book One Of The Lost In The Hood series, Jordan Jones, a software developer, has 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 ...

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 ...

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.

“Feeling like I could lose my bowels right then and there. I considered taking off, maybe to Brazil. Change my name. Change my look. I mean, change my look. Like, going through a male-to-female transition. I crossdressed, sometimes. Putting makeup on made me feel better, but something was missing. Like a vagina. If I’d been smarter instead of gambling away my salary, I’d have transitioned by now.” I always felt like I was out of place in my body. I’d crossdressed, but something was missing. I wanted to be a woman. A real woman. With breasts. Working equipment below. No more fake ...

Have you ever felt trapped in your male body? Did you feel more like a woman than a man? Have you ever looked at those captions on social media and asked:If you could take a pill and change into a woman, would you? Was your answer yes? Adan Howe was one of those men. Adan Howe is a safe cracker, a thief, and what he uncovers in his latest haul shocks him. He’s been set up to be a human guinea pig. Little do they know that he wants nothing more than to be a woman. But will the drug work? And if it does, they plan to change him back into a body he doesn’t want. Adan runs. He’s thrilled ...

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 ...

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 ...

Eve's world shatters as she discovers Adam's secret affair with their seductive Domme neighbor. Consumed by anger and betrayal, she confronts the woman and uncovers her husband's hidden desire to become a submissive sissy cuckold. In an act of revenge, Eve locks Adam in chastity for a week, determined to make him fully embrace his new role as her obedient and humiliated cuckold. But as the week progresses, will Adam succumb completely to his wife's control and become her permanent sissy slave? Only time will tell.

“Bound by desire, surrendered to pleasure.” Sissy Gina can’t stop complaining, but through complaining, she comes to realize the pleasure she derives from misbehaving and being punished. That is until Mistress Holly finds a discipline she cannot endure—being locked under their bed while she plays. For six long months, Sissy Gina remained locked, listening, and suffering until Mistress Holly invents a game. It's a game so sadistic and yet so fun. To return to warming up her bulls and playing with her and her bulls, Sissy Gina must win free nights by completing Sissy’s tasks and ...

Lily seethes with disgust at her lazy, slovenly husband. She hatches a devious plan to transform him into her obedient Sissy Cuckold Maid. Mason is resistant at first, but through humiliation and submission, he eventually embraces his role as a sissy cuckold husband. In addition to tending to Lily's domestic demands, Mason now serves as her sexual plaything, fulfilling her every desire and whim without question or hesitation. His masculinity stripped away, he exists solely for the pleasure of his dominant wife's satisfaction.

"An unexpected twist of fate ignites a forbidden love between a student and his seductive professor." In a world he always felt comfortable in writing, academia, and introspection, Cary, an infatuated, naive virgin eighteen-year-old student, uncovers his sordid desires under the guidance of his dominant, seductive literature professor, Mrs Delgado. Cary’s forbidden passions ignite under gentle pressure, sometimes not so mild. Will he sacrifice what was once sacred, his masculinity, for a taste of his English Professor? Will he let her turn him into her and her husband, Jerry’s sissy ...

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 ...

Jess is a crossdresser. No one knows about his secret, including his Alpha Male Roommate, Ryan. Ryan finds out about his best friend's secret: Crossdressing. Ryan's in a jam. He needs someone to play his girlfriend for a weekend trip home. Jess agrees to crossdress reluctantly for Ryan. Jess cross-dresses for Ryan and plays the part of his sweet, innocent girlfriend. Jess playing the part of Ryan's girlfriend, gets more than he bargains for with plenty of sex.

Book Four of The Series: Demoted To Sissy Cuckold Sissygasm Sissy Carter returns to work after being subjected to two days of intense orgasm denial and edging and needs relief desperately. He struggles at work, the chastity devices on his desk taunting him with what will happen. Soon he'll be locked up, with no choice but to wait for Mistress's Ella permission. He wonders where he can relieve himself. Mistress Ella has another very sadistic, challenging, and very public sissy assignment for him. Sissy Carter gets reliefs relief, his first Sissygasm, but it happens in a very public, ...

To everyone who knew Ty Gionata, he was a hardened criminal, a hardcore gangster. He takes no crap; you don’t want to cross Ty “The Coin” Gionata if your life depended on it. But Ty has a secret: the tough guy is an act, but he’s had to perfect that act to stay to survive. Tyla is more like him. In his secret condo in Miami, he has a secret life. Tyla’s life. Ty, Tyla loves sexy clothes and relaxing in her… or his femininity. The problem: his career as a criminal and his fears of getting caught crossdressing keep him from his one genuine desire—being a woman. He’s about to ...

Charlie Wilde was born male, or so everyone thought. When her equipment started growing, it was evident that he was a she. And yet her equipment down under was bigger than most women ever imagined. Charlie hid her package and avoided sex until one night. Her girlfriends get the surprise of a lifetime. In the morning, everyone leaves happy. This title includes Shemale lesbian, Shemale on female, oral sex, and group sex.