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    • Kitsy - Paddled & caned (a severe spanking in strappado with anal hook)
      16:47
      Kitsy - Paddled & caned (a severe spanking in strappado with anal hook)
      Kitsy Meow
      160.8K views
    • Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
      14:42
      Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
      Denise Humain
      31.1K views
    • Caning and choking Kitsy
      04:56
      Caning and choking Kitsy
      Kitsy Meow
      75.7K views
    • Pathetic Maid Apology Riding Crop Self Punishment
      13:17
      Pathetic Maid Apology Riding Crop Self Punishment
      JessicaLynn15
      2.3K views
    • Spiked Chastity Cage Torment - Sissy Maids Self Bondage
      18:39
      Spiked Chastity Cage Torment - Sissy Maids Self Bondage
      Derek6699
      101.1K views
    • How to Give Pain and Pleasure to a Big Sissy Cock
      11:41
      How to Give Pain and Pleasure to a Big Sissy Cock
      MyLolaTrav
      58.3K views
    • More maintenance spanking for Kitsy. OTK punishment.
      06:53
      More maintenance spanking for Kitsy. OTK punishment.
      Kitsy Meow
      23.7K views
    • Sissy Denise: Tied Nipples Tortured with Rough Round Brushes
      18:54
      Sissy Denise: Tied Nipples Tortured with Rough Round Brushes
      Denise Humain
      2.8K views
    • Slapping My Tits and Ass Like a Good Pain Slut
      08:55
      Slapping My Tits and Ass Like a Good Pain Slut
      Gray Perrier
      6.2K views
    • some fun kitty playtime
      16:17
      some fun kitty playtime
      Kittykisses96
      20.9K views
    • Sissy Maid Icy Hot Wooden Pony Punishment 2
      23:29
      Sissy Maid Icy Hot Wooden Pony Punishment 2
      Derek6699
      39.4K views
    • How a Tgirl severely punishs her big cock.
      10:29
      How a Tgirl severely punishs her big cock.
      MyLolaTrav
      43.6K views
    • Extreme Painanal large dildo with chilli sauce pushes Denise to her limits and makes her cry.
      14:26
      Extreme Painanal large dildo with chilli sauce pushes Denise to her limits and makes her cry.
      Denise Humain
      43.1K views
    • How to torture a beautiful sissy cock
      09:59
      How to torture a beautiful sissy cock
      MyLolaTrav
      27.4K views
    • A desperate trap sissy pain whore asks a top man to take her as a sex slave and let him fuck her throat and ass
      01:34
      A desperate trap sissy pain whore asks a top man to take her as a sex slave and let him fuck her throat and ass
      alinanightsky
      41K views
    • Rebeccas Pervertions 8
      11:21
      Rebeccas Pervertions 8
      Rebeccafuxx
      17.3K views
    • Sissy Denise: Nipple torture with combination pliers – Live until the end
      09:37
      Sissy Denise: Nipple torture with combination pliers – Live until the end
      Denise Humain
      2.6K views
    • Sissy Maids Punishment
      07:53
      Sissy Maids Punishment
      Derek6699
      27.9K views
    • Icy Hot Wooden Pony Self Bondage Torture
      17:40
      Icy Hot Wooden Pony Self Bondage Torture
      Derek6699
      26.7K views
    • Let her feel what Nipple Pain means. Let her suffer to her limit while we smile at her.
      13:59
      Let her feel what Nipple Pain means. Let her suffer to her limit while we smile at her.
      Denise Humain
      20K views
    • Another weekend - Same result, nipples hurt, asshole is destroyed, still i wish i dont had to do it by myself.
      14:21
      Another weekend - Same result, nipples hurt, asshole is destroyed, still i wish i dont had to do it by myself.
      Denise Humain
      13.7K views
    • Candle Wax & Chastity Go Together like PB & Jelly
      07:05
      Candle Wax & Chastity Go Together like PB & Jelly
      MJ
      7.5K views
    • Mistress Cy IPL Hair Removal Punishment
      07:02
      Mistress Cy IPL Hair Removal Punishment
      Cyanide Mistress Of Darkness
      16.7K views
    • Rebecca's painful Orgasm
      10:49
      Rebecca's painful Orgasm
      Rebeccafuxx
      9.6K views
    • A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
      28:23
      A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
      Denise Humain
      12.2K views
    • Tabasco Dildo Punishment for forgetting my butt plug today...
      02:50
      Tabasco Dildo Punishment for forgetting my butt plug today...
      Sissy-Hinata
      3.5K views
    • The Pressure of Pain and Punishment
      03:41
      The Pressure of Pain and Punishment
      BadGod
      6.7K views
    • Rebeccas Perversions 10
      05:35
      Rebeccas Perversions 10
      Rebeccafuxx
      1.1K views
    • (P.4-5) Athena 50 Shades of FUCKED UP TATTOO BDSM XXX 666
      30:01
      (P.4-5) Athena 50 Shades of FUCKED UP TATTOO BDSM XXX 666
      Cyanide Mistress Of Darkness
      10.7K views
    • dumb slut gets the belt for cumming without permission
      04:08
      dumb slut gets the belt for cumming without permission
      Bambi Christa
      12.6K views
    • Domination and pain with this 2 shemales hardcore punishment
      10:07
      Domination and pain with this 2 shemales hardcore punishment
      Latina Tranny
      31.4K views
    • BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
      07:34
      BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
      Denise Humain
      5.8K views
    • Maso Whore Rebecca
      07:25
      Maso Whore Rebecca
      Rebeccafuxx
      1.2K views
    • Fat Sissy light ball torture and wax play in chastity
      03:02
      Fat Sissy light ball torture and wax play in chastity
      Chubby Sissy Dani
      5.4K views
    • I am a naughty bitch that needs to be punished severely
      06:39
      I am a naughty bitch that needs to be punished severely
      Victoria Lecherri
      4.7K views
    • Femboy slut gets hard ass spanking as punishment (SissySandyy20 Solo)
      03:43
      Femboy slut gets hard ass spanking as punishment (SissySandyy20 Solo)
      Sissy Sandy
      7K views
    • Little sluts bills punishment
      10:18
      Little sluts bills punishment
      7.6K views
    • Tyche_Toxic Winces In Pain During Self CBT
      01:14
      Tyche_Toxic Winces In Pain During Self CBT
      Tyche Toxic
      5.4K views
    • Maso Muslima squirts in Pain
      06:27
      Maso Muslima squirts in Pain
      Rebeccafuxx
      16K views
    • FtM boy punished for being lazy
      05:10
      FtM boy punished for being lazy
      4.7K views
    • A sissy tortures her buttocks severely with nettles, ties up her balls, dildoes herself and makes herself cum with the vibrator
      18:03
      A sissy tortures her buttocks severely with nettles, ties up her balls, dildoes herself and makes herself cum with the vibrator
      MyLolaTrav
      8.3K views
    • Shemale cock and nipples pain...
      06:02
      Shemale cock and nipples pain...
      MyLolaTrav
      5K views
    • Hot Wax On Sissy Cock
      04:15
      Hot Wax On Sissy Cock
      SubmissiveFetish
      4.7K views
    • BambiChrista gets punished for making demands of her Master. She has to hit clothspins off her butt and thighs
      06:35
      BambiChrista gets punished for making demands of her Master. She has to hit clothspins off her butt and thighs
      Bambi Christa
      5K views
    • sissy slut punishing herself with a paddle
      02:49
      sissy slut punishing herself with a paddle
      Emma Huntcock
      3.6K views
    • Painful nipple torture chains
      09:19
      Painful nipple torture chains
      2.2K views
    • Cock Punishment
      00:07
      Cock Punishment
      SubmissiveFetish
      1.8K views
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