50th time I get caned


  • Caning at home

    Caning at home

  • Long slow caning of over 400 strokes

    Long slow caning of over 400 strokes

  • Caned over the back of a chair

    Caned over the back of a chair

  • Start of a hard caning

    Start of a hard caning

  • Caned over a desk

    Caned over a desk

  • 10 strokes of cane on red ass stripes

    10 strokes of cane on red ass stripes

  • Spanked 333 times by Sir

    Spanked 333 times by Sir

  • My Hardest Spanking Yet Part 1

    My Hardest Spanking Yet Part 1

  • Caned with six slow and six fast strokes

    Caned with six slow and six fast strokes

  • Caned in Chesterfield

    Caned in Chesterfield

  • Spanked, belted and caned

    Spanked, belted and caned

  • Master uses various implements on my bottom

    Master uses various implements on my bottom

  • Collared twink cum sprayed after raw fucking with his lover

    Collared twink cum sprayed after raw fucking with his lover

  • Naughty burglar caned

    Naughty burglar caned

  • Country Boy gets the Cane and Belt Hard

    Country Boy gets the Cane and Belt Hard

  • New boy paulo stripes

    New boy paulo stripes

  • Punished for masturbating in the showers

    Punished for masturbating in the showers

  • 4 implements

    4 implements

  • My bare buttocks get caned, strapped and spanked

    My bare buttocks get caned, strapped and spanked

  • Belt, strap,tawse and leather paddle

    Belt, strap,tawse and leather paddle

  • Positions for a beating

    Positions for a beating

  • Collar whipping with a belt by the owner 10 times

    Collar whipping with a belt by the owner 10 times

  • My fourth ever caning

    My fourth ever caning

  • Find Harper - Bondage

    Find Harper - Bondage

  • Session 1: Card Game, 1/26/2021

    Session 1: Card Game, 1/26/2021

  • Spanked and wanked

    Spanked and wanked

  • Caned 24 strokes on trousers, pants and bare

    Caned 24 strokes on trousers, pants and bare

  • Kris Karis Poolboy OutDoor Spanking by BlackBear

    Kris Karis Poolboy OutDoor Spanking by BlackBear

  • Punished the for not fulfilling orders and fucked in the ass and mouth...... Oliver Strelly Falcon Al Max Gen - 13

    Punished the for not fulfilling orders and fucked in the ass and mouth...... Oliver Strelly Falcon Al Max Gen - 13

  • Caning September 2017

    Caning September 2017

  • A history of my restraint

    A history of my restraint

  • Receiving 18 strokes of the cane in my pyjamas

    Receiving 18 strokes of the cane in my pyjamas

  • Horny uncut hunk getting spanked and his cock tugged

    Horny uncut hunk getting spanked and his cock tugged

  • Spanked Hard and in Pain

    Spanked Hard and in Pain

  • spanking for a twink

    spanking for a twink

  • My striped bum gets fucked by a cute Romanian lad

    My striped bum gets fucked by a cute Romanian lad

  • Caned hard then examined

    Caned hard then examined

  • Session 2: 1000 Strokes 2.03.2021

    Session 2: 1000 Strokes 2.03.2021

  • Got Spanked

    Got Spanked

  • Bad boy is caned hard

    Bad boy is caned hard

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