sissy

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!

Generate your own personalized 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!

Stories

The Blacked World VR Experience

By qosis

RedQuill

RedQuill

Toby, a straight-laced young man, receives a VR headset for his birthday, leading him to discover a hidden world of sexual hypnosis and interracial domination. His curiosity turns into an addiction as he becomes increasingly obsessed with a VR game that transforms his perceptions of sexual pleasure and identity.

A Sissy Star is born

By sissy_jazmin

RedQuill

RedQuill

Nick and his girlfriend, Amy are struggling to pay the rent. With few options left, Amy suggests they make their own porno. Nick isn't sure and has serious reservations when Amy tells him that straight porn is oversaturated and suggests they try sissy porn. Nick is transformed into Nikki and with Amy's help, falls deeper and deeper into his new role as a sissy porn star.
Maya's Forbidden Lingerie Ecstasy Unleashed
Male to female cross dresser want to be a female
The Wife's Black Harem
A submissive husband, dressed in lace and silk, is dominated and used by his wife and her three muscular black lovers in a dimly lit room. The wife, dressed in a sleek leather corset, commands her husband to serve the men, who take turns fucking him, as she watches and masturbates. The husband is filled and used by his wife's lovers, taking their cocks in his mouth and ass, while his wife watches with pleasure, enjoying the sight of her husband being ravaged and dominated.
One Photo Can Make So Many Changes
A loving couple stumble upon an old photo which leads down a long, dark, and winding path to a new life

Theatrical Submission

By wilddaisy85

RedQuill

RedQuill

A crossdresser meets a couple at a sex theater, where he is feminized and forced to perform sexual acts on the husband and other men. The wife enjoys being pleasured by other sissies and watches as her husband fucks the crossdresser, who is then passed around for anal sex and eventually has a sissygasm.

Wardrobe Malfunctions Ignite Sissy's Thrill

By smut4me

RedQuill

RedQuill

A young exhibitionist, Pepper, seeks thrills at the beach, only to find herself in a series of wardrobe malfunctions that expose more than she intended. Her fantasies are fueled by the sight of stunning women in revealing swimwear, leading her to a state of intense arousal and public self-pleasure. A chance encounter with a woman who accidentally exposes herself pushes Pepper over the edge, leading to a risky and exhilarating climax.

Sissy's Overflowing Cravings Filled Deeply

By hannahcumbucket

RedQuill

RedQuill

Hannah, a sissy under the 2023 Sissy Mandate, is publicly used and filled multiple times during a trip to the shops, leaving her dripping and craving more. Upon returning home, she encounters her neighbor, Mr. Evans, who offers to help her with her "overflow problem," leading to a raw, intense breeding session in his apartment. The encounter involves verbal degradation, praise for her role as a communal whore, and the use of a plug to keep her filled with multiple loads of semen, culminating in a post-orgasm creampie continuation.

Surrendering to Cindy's Feminine Spell

By secretsissyjamie

RedQuill

RedQuill

Cindy uses hypnotic influence to transform Jeremy into a submissive sissy named Jamie, dressing him in feminine attire and painting his nails. She then invites her dominant gay friends, Quincy and Chris, to join them without Jamie's knowledge, setting the stage for a night of intense exploration and submission. The men take control, pushing Jamie's boundaries and guiding him through a transformative experience that challenges his perceptions of self and desire. Jamie's journey involves deep emotional and physical exploration, culminating in a night of intense, consensual submission and discovery.

Sissy Jean's Altar Gangbang Breeding Orgy

By hannahcumbucket

RedQuill

RedQuill

A transgender bride, Sissy Jean, is forced to undergo a public gender reveal and a brutal gangbang on her wedding day, as per the 2023 Sissy Law. The ceremony involves intense verbal degradation, multiple partners, and a focus on breeding, with the bride being used and filled repeatedly until she collapses at the altar, her body a vessel for the congregation's pleasure.
Components
Betrayal by a Confidant background

Betrayal by a Confidant

A close ally (partner, best friend) discovers the protagonist's repressed sissy fantasies and orchestrates scenarios to "help" them transition—often with ulterior motives (e.g., cuckolding fetish). Scenes must involve gaslighting ("You've always wanted this"), staged "accidents" (public wardrobe malfunctions), and emotional manipulation using guilt or affection to erode resistance. Focus on bittersweet tension between betrayal and liberation

Details

Trope

5881

Locked in chastity as proof of submission background

Locked in chastity as proof of submission

The character's genitals are secured in a chastity device that requires another's permission to remove. Scenes will emphasize the constant reminder of their restricted state during daily activities and sexual encounters. This device creates ongoing sexual frustration while visually demonstrating complete control by a dominant figure.

Details

Plot Device

1212

Forced sissy sissygasm training background

Forced sissy sissygasm training

Detailed sessions using toys and penetration to train the character's body to cum from anal stimulation alone. Focus on the confusion of enjoying 'wrong' pleasure. This device physically rewires sexual response to reinforce sissy identity.

Details

Plot Device

936

Enforced cross-dressing session background

Enforced cross-dressing session

The scene will focus on the physical act of being dressed against one's will, with detailed descriptions of lace panties, stockings, and a maid uniform being meticulously put on the reluctant participant. The humiliation comes from both the forced feminization and the commentary on their transformed appearance. This plot device emphasizes power exchange through clothing as a symbol of submission.

Details

Plot Device

875

Hypnotic Temptation background

Hypnotic Temptation

The protagonist encounters a hypnotist/charismatic influencer who implants triggers linking arousal to femme behaviors (e.g., blushing when called "good girl"). Over time, post-hypnotic commands escalate: stripping masculine habits (deep voice), adopting submissive gestures (curtsying), or craving humiliation like being dressed by strangers. Ensure trance sequences blend dreamlike obedience with moments of lucid panic about losing control.

Details

Trope

709

Hypnosis-induced feminization background

Hypnosis-induced feminization

The character undergoes hypnosis sessions where they're conditioned to enjoy makeup application, girlish movements, and receptive sexual postures. Focus on the gradual erosion of masculine identity through suggestive repetition. This device allows exploration of subconscious transformation and programmed responses.

Details

Plot Device

576

Sissy posture and walk training background

Sissy posture and walk training

The character is forced to balance books on their head while walking in heels, with posture corrections administered via crop or verbal abuse. Focus on muscle fatigue and repeated failures. This device connects physical discomfort to identity transformation through bodily discipline.

Details

Plot Device

277

Cum denial as motivation tool background

Cum denial as motivation tool

The character is kept in a state of perpetual arousal, with ejaculation permitted only after completing particularly humiliating acts. Focus on the desperation that builds over days or weeks. This device utilizes biological imperative to drive narrative progression through suffering.

Details

Plot Device

234

Forced confession of sissy desires background

Forced confession of sissy desires

The character must explicitly describe their secret urges into a camera or microphone, with threats of the recording being shared. Scenes emphasize stammering admissions and tearful vulnerability. This device makes abstract desires concrete through verbal articulation under duress.

Details

Plot Device

209

Sissy speech pattern coaching background

Sissy speech pattern coaching

The character must repeat phrases in a high-pitched voice while being corrected for insufficient femininity. Includes lessons on giggling, using deferential language, and adopting a 'sissy lisp'. This device attacks identity through vocal transformation and verbal self-degradation.

Details

Plot Device

207

red quillRedQuill

RedQuill is a free AI erotic story writer that lets you instantly explore and remix your kinky, sexy fantasies in a safe and vibrant community.

Innerworlds, Inc.

169 Madison Ave, STE 11408

New York, NY 10016

© 2025 RedQuill. All Rights Reserved