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...

Jake Barlowe has just won a high-profile case for the wealthiest man in the world. He should be happy, but he isn’t. He hates his client, Sebastian Oliver. He hates how he destroyed Oliver’s accuser’s reputation again. But his job as an attorney is to defend his clients, even scum like Oliver. After a night of drinking with Oliver, Barlowe leaves the party drunk and drives home. With two DUIs under his belt, he can ill afford another one, which would be a felony and possibly send him to prison. On his way home, he’s pulled over by Sheriff Avery, the sister of the woman Oliver ...

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, ...

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-...

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...

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 ...

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 ...

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...

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 ...

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 ...

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.

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 ...

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 ...

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 ...

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, ...

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...

Because of his secret desire to crossdress, Jaden steals women's intimates from a store and ends up on probation. Mr. Ventura, his Probation officer, secretly desires to be with a sissy crossdresser. Penny, Jaden's best friend, has an idea to get Jaden off probation, change him into a woman, to feminize him. Jaden agrees to be femininized but reluctantly. In the end, Mr. Ventura gets his wish, and so does Jaden.

Mr. Gay, a tenured college psychology professor, pretends he's conducting a study on sexual kinks, specifically about crossdressing and feminization. He acts like he's interviewing a stripper and dominatrix at a local bar. In reality, he's too scared to take the first step toward his secret desires to be feminized and crossdress. To talk to Kitty, he has to buy her drinks at the bar, and this causes him to get behind on his rent. Fed up with his delinquent rent, Ms. Martinez, his landlady, and a highly skilled special effects and makeup artist, plans to get her rent money and transform Mr. ...

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 ...

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 ...