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A couple who have been dating a while, not married crossdressing stories

Stories in Crossdressing tagged a couple who have been dating a while, not married, ranked by how many readers finish them. Reads run 12 to 17 minutes. Writers to know: Flint Notebook, Crimson Street and The Ochre Novel. Readers usually start with “Slam Dunk” and “Anniversary Dress”. Some are free to read in full; the rest open with a free preview.

Average 14 min · updated 12 Aug 2026

A couple who have been dating a while, not married crossdressing stories, ranked by readers

  1. 01

    Slam Dunk

    The mic squealed when I set it back in the stand.

    Premium · Room of Thistle · Crossdressing · 18 min · funny and chatty, body worship, a couple who have been dating a while, not married

  2. 02

    Anniversary Dress

    I'm twenty-eight years old, and I own a farm, and last Thursday I bought a dress.

    Premium · Delta Corner · Crossdressing · 11 min · matter-of-fact, latex, a couple who have been dating a while, not married

  3. 03

    Cork and Crepeline

    The potluck had been going for about two hours when Callie hit her stride.

    Premium · Onyx Crossing · Crossdressing · 12 min · raw and blunt, ski town, a couple who have been dating a while, not married

  4. 04

    Crow and Copper

    I was twenty-seven years old the summer I started following Leroy out to the old lampblack plant, and I will state that up front because…

    Premium · Flint Notebook · Crossdressing · 16 min · music scene, latex, a couple who have been dating a while, not married

  5. 05

    Dressed for Her Pleasure

    *This one came from a moody image of an empty school gym at night and the idea of finding intimacy in the most unexpected places.

    Premium · Flint Notebook · Crossdressing · 12 min · a couple who have been dating a while, not married, dark and intense, uniforms

  6. 06

    The Sommelier's Dress

    Vic and I had been together two years when the dry spell hit, and it didn't hit like a storm.

    Premium · Birch Logic · Crossdressing · 14 min · warm and nostalgic, latex, a couple who have been dating a while, not married

  7. 07

    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

  8. 08

    The Curator's Dress

    I'm fifty-two years old and I have been standing in the doorway of a dressing room for a full two minutes without saying anything.

    Premium · Salt Narrative · Crossdressing · 10 min · raw and blunt, film set, a couple who have been dating a while, not married

  9. 09

    A Galley of His Own

    I've been the sous chef on the Pride of the Caribbean for three years now, which sounds fancier than it is.

    Premium · Sage Word · Crossdressing · 12 min · tender and slow, a couple who have been dating a while, not married, feet

  10. 12

    The Record of Her

    The lot list was lying on the corner table where I'd left it, and I'd been walking the preview hall at Fitch's for about two hours by then.

    Premium · The Ochre Novel · Crossdressing · 13 min · tender and slow, a couple who have been dating a while, not married, hotel or conference

  11. 15

    Trunk Trick

    My name is Steve, I'm twenty-three, and I work nights at a locksmith dispatch call center.

    Premium · Dawn Post · Crossdressing · 15 min · leather, matter-of-fact, a couple who have been dating a while, not married