Showing results by author "Phoebe Pearl" in All Categories

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 ...

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 ...

Mistress Joyce begins her sissy slave training with Asher, sexually servicing Tiffany, a well-endowed transgender woman that once worked as a stripper at The Dirty Secret - the club Mistress Joyce manages. While accepting his role as a sissy and enjoying his new persona as Ashley. Asher must keep it a secret from his nosey father or risk losing his fortune. He's managed to convince his father to write him into the will. But he must complete one more task, buy The Dirty Secret. After breaking Asher in with Tiffany, Mistress Joyce transforms Asher into Ashley, her sissy slave, with a night of...

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, ...

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 ...

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.

"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 ...

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...

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-...

“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 ...

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 ...

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.

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 ...

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 ...

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 ...

He has a secret that no one can know. So does she. When she catches him wearing panties, he has no option but to submit…. Will she expose his deepest, darkest secret? Or give him a choice and feminize him completely? Teaming up with her Dominatrix friend, Miss Hart devises a scheme to expose Billy’s secret fetish and feminize him. Billy fears if his Mother, the owner of the firm, finds out about his kinky desires, she’ll cut him off, and everyone will know about his secret sissy urges. Will Billy give in to his secret fetish and let Miss Hart feminize him? Will he abandon his ...

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...

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 ...

I had felt the need to change before I could remember. I wanted to dress in ways that would make me feel comfortable and like myself. But at the same time, guilt and fear weighed heavily on me. I longed to be who I truly was, yet something held me back from making choices that were true to my inner voice. When I caught Angela, my fiancée, with my boss, I ran to see an old friend: Claude. We loved writing and had similar views, but we didn't share that we both enjoyed cross-dressing--though Claude suspected. I never admitted it. I wasn't sure what I was expecting when I stumbled upon Claude...

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 ...