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Chastity first time stories

Stories in First Time tagged chastity, ranked by how many readers finish them. Reads run 19 to 25 minutes. Writers to know: North Craft, Loop of Paper and Linen Quota. Readers usually start with “The Debt Was a Story” and “The Tuesday Arrangement”. Some are free to read in full; the rest open with a free preview.

Average 22 min · updated 2 Jun 2026

Chastity first time stories, ranked by readers

  1. 03

    The Barge Date

    So there I was, standing on the landing stage at Pier Head at seven o'clock on a Thursday evening, holding a bottle of wine my sister…

    Premium · North Craft · First Time · 25 min · chastity, a couple who have been dating a while, not married, playful and teasing

  2. 04

    When the Truth Slips Out

    Some nights the dispatch desk felt less like a job and more like a chair I rented from the university.

    Premium · North Craft · First Time · 16 min · raw and blunt, chastity, old classmates now adults

  3. 05

    The Wrong Fitting

    Liza arrived at the motel with her jaw already tight, which was mostly Chrissie's doing.

    Premium · Linen Quota · First Time · 21 min · raw and blunt, chastity, friend of a friend

  4. 06

    The Doorbell

    The trail up to the hut nearly killed me, and I mean that in the most dramatic way possible.

    Premium · Loop of Paper · First Time · 24 min · chastity, old classmates now adults, playful and teasing

  5. 07

    First Frost

    The drive up took six hours and I did most of it with the radio off, which should tell you something about the state I was in.

    Premium · Roan Tempo · First Time · 26 min · music scene, chastity, tender and slow

  6. 08

    A Sweet Lesson

    The band was playing something slow and the fairy lights were doing their thing over the fountain, and I stood there with a glass of…

    Premium · The Breeze Draft · First Time · 19 min · chastity, spouses, wedding or party