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Chastity crossdressing stories

Stories in Crossdressing tagged chastity, ranked by how many readers finish them. Reads run 15 to 19 minutes. Writers to know: Amber Garden, Sundown Logic and Crimson Street. Readers usually start with “Linen Closet Tryst” and “The Barge Photographs”. Some are free to read in full; the rest open with a free preview.

Average 16 min · updated 24 Oct 2026

Chastity crossdressing stories, ranked by readers

  1. 01

    Linen Closet Tryst

    I signed up for the couples cooking class alone, which tells you most of what you need to know about me.

    Premium · Amber Garden · Crossdressing · 15 min · chastity, domestic routine, coworkers

  2. 03

    What the Maid Hid

    My cousin Sara got married on a Saturday in October, and somehow I ended up being the one who stayed behind to watch the lodge.

    Premium · Laurel Logic · Crossdressing · 17 min · chastity, breathless and eager, rivals

  3. 04

    Mudjack and Lemon Lime

    The fluorescent strip over the filing cabinets had a bad ballast, so it buzzed and flickered every few seconds, and Mallory Moreau had…

    Premium · The Cypress Witness · Crossdressing · 20 min · chastity, funny and chatty, boss and employee (both adults, consensual)

  4. 05

    Pit Stop Surprise

    Turning twenty-nine is a weird kind of birthday, because nobody warns you that it feels like running out of road.

    Premium · Amber Garden · Crossdressing · 19 min · chastity, car garage, matter-of-fact

  5. 06

    The Hidden Photo

    The cat started yowling around eleven on Tuesday night, and by midnight I was carrying her carrier through the rain to the emergency vet…

    Premium · Craft of Hollow · Crossdressing · 18 min · raw and blunt, chastity, strangers

  6. 08

    Rehearsal Required

    Connor came in the back door at six fifteen and dropped his keys in the bowl by the mudroom hook, the same way he did every night, except…

    Premium · The Laurel Gazette · Crossdressing · 17 min · chastity, spouses, suburb