Crossdressing Stories

Discover AI Generated Erotic Stories, Story Ideas and Components from the RedQuill Community

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Seduction in Silk and Shadows Unveiled

A closeted cross-dresser's secret life is discovered by his coworker, leading to a series of intimate conversations and a date that blurs the lines between Michael and his alter ego Karen. Rick's curiosity and acceptance allow Michael to explore his feminine side openly, culminating in a passionate encounter where Karen's true desires are revealed and fulfilled. The narrative delves into themes of identity, acceptance, and the erotic tension between a man and his alter ego, with explicit scenes of oral sex and mutual masturbation.

Cosmotologist Final Exam

Ben, a man in his late 20s, wakes up to find himself bound and naked on a padded table, surrounded by three young women and their instructor, Rachel. The women are cosmetology students, and Ben is their final exam subject. He must endure a full transformation into a woman, including waxing, makeup, and a final outfit, all while restrained and unable to escape. The story explores themes of consent, vulnerability, and the power dynamics between the students and their subject.

Anne's Perfect Pastry

Ben visits a charming 1950s-style bakery owned by Anne, a captivating redhead who flirts with him in a way that feels more than just sexual. Anne offers Ben a new pastry she's been working on, which he finds delicious. As he begins to feel sleepy, Anne guides him to a chair and he passes out.

Samantha's Waxing Ritual of Forbidden Desire

A man, Ben, is captured and bound by a seductive, older woman, Samantha, who has a unique and painful fetish. She subjects him to a full leg waxing and a complete pedicure, culminating in the humiliation of wearing high-heeled shoes.

¡The Crossdresser Rimuru!

By naounable

RedQuill

¡The Crossdresser Rimuru!

Rimuru, and androgynous boy try Crossdress! But he sometimes get's caught, anyway he tries to don't get caught too easily, but when he is aroused he does not think about consecuences.

Dressed in Desire

By romnixx