Sissy Stories

Stories about the liberating journey of embracing femininity and submission through sissy transformation! Sissy play involves men exploring their feminine side through cross-dressing, behavior modification, and often submission to dominant partners. The appeal comes from the complete transformation, the exploration of gender roles, and the freedom to embrace a different side of sexuality. From makeup and lingerie to complete lifestyle changes, sissy stories celebrate the journey of becoming more feminine, submissive, and sexually available. It's about transformation, submission, and the joy of embracing a new identity!

Forced Feminization

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From Corporate Error to Intimate Surrender

By mrplains

RedQuill

From Corporate Error to Intimate Surrender

A new employee at a prestigious law firm makes a costly accounting error and is given an ultimatum by the Futa CEO: become her sissy slave for the company's relaxation or be fired. The employee chooses to serve, submitting to the CEO's every whim, including performing oral sex and being used for sexual pleasure in a variety of ways. The employee's role evolves from a professional position to a sexual resource for the CEO and other executives, experiencing both humiliation and unexpected pleasu...

The Midnight Strut of a Sissy Cumdump

A young girly sissy with huge protruding nipples, fat bubble butt and a tiny penis walks around at night in revealing clothing. He passes a group of older men who start talking dirty to him, turning him on. The sissy gets gangbanged by the burly men on the street, while strangers gasp in shock and humiliate the sissy. The men talk dirty to the sissy, calling him a slut, cumdump, whore, etc. One after one they ejaculate into his ass, down his throat, and on his face, until he's completely cov...

Kiran’s Sissy Month of Humiliation and Tease

Kiran, a mischievous student, finds himself in hot water after being caught lifting the skirts of female classmates and exposing their panties. As punishment, the headmaster and the mother of one of the victims decide that Kiran will spend a month living as a girl. He is forced to shop for underwear, wear dresses and a school uniform, and endure humiliating encounters in public.

Sissys Shocking Caged Submission to Exes Lover

By chrissyjingles

RedQuill

Sissys Shocking Caged Submission to Exes Lover

A jilted fiancé, humiliated and left for another man, is lured back into a twisted game of revenge and humiliation. After being manipulated into dressing as a sissy and locked into chastity, the protagonist is forced to perform oral sex on the man who replaced him, all while being recorded and degraded by his ex-fiancée. The narrative explores themes of cuckolding, forced feminization, and public humiliation, as the protagonist's deepest insecurities and desires are exploited for the pleasure o...

Danny’s sissy heaven

By jodie

RedQuill

Danny’s sissy heaven

Danny gets enslaved by a money lender and gets transformed into a BBC sissy slut

Sissy Wavie's Reveal

Wavie, a teenage sissy boy, is exposed by his parents when they discover his hidden sissy wardrobe and journal detailing his fantasies of being a submissive cocksucker for neighborhood boys. His parents, instead of being horrified, decide to confront his desires head-on by inviting Bobby Miller, a popular and dominant jock, to their home to fulfill Wavie’s fantasies in front of them. Wavie is forced to dress up in his most feminine outfit and service Bobby, experiencing a mix of terror and thr...

Your own smutty sissy story

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