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!

Forced Feminization

Sissy Cuckold

Forced Crossdressing

Your own naughty sissy story

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Bakery Visit Turns Ben into Bambi

A man named Ben visits a charming 1950s-style bakery owned by a captivating redhead named Anne, 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. The pastry contains a special spice blend that induces a euphoric and sleepy state, allowing Anne to have her way with Ben while he is unconscious. Anne's intentions are clear as she takes advantage of Ben's vulnerable state, hinting at a dark and possessive nature beneath her charming exterior.

Unlocked

By bisissy420666

RedQuill

Unlocked

A crossdressing husband is initiated into a month-long training regimen by his BBW wife, who locks him in delicate lingerie and restrictive chastity, gradually introducing him to an expanding arsenal of toys designed to probe and expand his ass in daily sessions. The husband's training includes spontaneous, intimate urination rituals and culminates in sessions where he is guided to swallow his own eruptions, building layers of devotion and surrender in their deepening power dynamic.

The Sissy Maid's Enchanting Estate Surrender

By karencorset

RedQuill

The Sissy Maid's Enchanting Estate Surrender

A crossdresser answers a job advertisement for a live-in sissy maid position, finding herself in a luxurious estate with a distinguished older man. The maid's uniform is short, pink, and frilly, and the employer is immediately appreciative of her appearance. The employer, Jo, is kind and gentle, and the two share a passionate kiss in the foyer. Jo leads the maid to his bedroom, where he admires her body and teases her with his touch.

Aunt Cassandra's Forbidden Lingerie Fisting Feast

By skin05

RedQuill

Aunt Cassandra's Forbidden Lingerie Fisting Feast

A young man, Leo, is caught by his aunt Cassandra while dressing in her sexy lingerie. The encounter leads to a dominant and intimate experience where Leo is feminized, fisted, and pushed to his limits in a thrilling exploration of power dynamics and taboo desires.

Whispered Sissy Desires

By autobots

RedQuill

Whispered Sissy Desires

An 18-year-old Bengali Hindu teen, Krish, discovers a new world of crossdressing and trans porn during lockdown, finding similarities between himself and the sissies in the videos, leading to a fixation on dominant, hairy, muscular older men. Krish's journey begins with sissy hypno training videos, leading him to mimic the acts he sees on screen, including crossdressing and self-pleasure, ultimately driving him to seek out sissy clothing to further his transformation.

Whispered Sissy Desires

By krish007

RedQuill

Whispered Sissy Desires

Your own naughty sissy story

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