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    • Aching For Your Love by OnceUponATime
      00:30
      Aching For Your Love by OnceUponATime
      3.3K views
    • A sexy Sissy ties her big cock with a rope and gives her pain with nettles before cuming
      08:15
      A sexy Sissy ties her big cock with a rope and gives her pain with nettles before cuming
      MyLolaTrav
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    • BDSM chopsticks's play
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    • Sissy and the tip
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    • Painful constant wanking after chastity phase! Tranny Girl has 9 (!) ruined orgasms and 5 cumshots!!
      00:43
      Painful constant wanking after chastity phase! Tranny Girl has 9 (!) ruined orgasms and 5 cumshots!!
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    • Labor Pains
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      Labor Pains
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    • Synnz & Mistress Cy "50 Shades of Fucked Up" Shemale Tattoo BDSM Kink Fuck Session (FULL RELEASE)
      01:29:00
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    • Rebeccas Perversions 10
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      Rebeccas Perversions 10
      Rebeccafuxx
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    • Fifty Shades of FUCKED UP!! Advance Preview Trailer!!
      03:41
      Fifty Shades of FUCKED UP!! Advance Preview Trailer!!
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    • booty ass fat bbw big geng cum sperm squirt piss pain spit
      00:46
      booty ass fat bbw big geng cum sperm squirt piss pain spit
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    • Mistress Cy IPL Hair Removal Punishment
      07:02
      Mistress Cy IPL Hair Removal Punishment
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    • No pain no sissy gain
      01:32
      No pain no sissy gain
      Kittykisses96
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    • Clamping my nipples and clit, masochism
      02:03
      Clamping my nipples and clit, masochism
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    • 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
      5K views
    • Painful Anal with a huge vegetable
      01:01
      Painful Anal with a huge vegetable
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    • Dildo, Jerking, a little Pain
      06:05
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    • Ladyboy Lisa 3 Pain And Pleasure
      06:12
      Ladyboy Lisa 3 Pain And Pleasure
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    • 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
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    • sissy slut punishing herself with a paddle
      02:49
      sissy slut punishing herself with a paddle
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    • BRUTAL Tgirl TOP Gives Guy Extreme Painal
      02:24
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    • Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
      44:10
      Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
      alinanightsky
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    • Painting tranny
      07:53
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    • The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded
      10:53
      The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded
      alinanightsky
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    • Pain Slut Kira
      36:28
      Pain Slut Kira
      Twistedrama
      96K views
    • 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
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    • Pain and pleasure, chastity and lust, Part 2
      01:15:02
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    • Tranny Barbie can't take the BBC and tries to get away but he keeps fucking my ass hard - amateur shemale - Candy Ass Sissy
      06:08
      Tranny Barbie can't take the BBC and tries to get away but he keeps fucking my ass hard - amateur shemale - Candy Ass Sissy
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    • DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      02:37
      DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
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    • she puts her bikini aside and fucks him in painful doggy
      03:20
      she puts her bikini aside and fucks him in painful doggy
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    • Pain and pleasure, chastity and lust,  Part 1
      51:35
      Pain and pleasure, chastity and lust, Part 1
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    • Pain and Pleasure  Part 2
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    • Caning and choking Kitsy
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      Caning and choking Kitsy
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    • 116 min degrading of bdsm sissy pain whore Alina
      02:20
      116 min degrading of bdsm sissy pain whore Alina
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    • Transgender Pain Slut Strokes Off With Nipple Clamps For Whorish Reasons
      08:01
      Transgender Pain Slut Strokes Off With Nipple Clamps For Whorish Reasons
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    • Compilation with Weekly Episodes from the pain whore Alina
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      alinanightsky
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    • Slapping My Tits and Ass Like a Good Pain Slut
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      01:33
      fucking my femboy slave sissy slut painful anal
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    • Redhead Asian shemale all covered in pain gets fucked
      07:10
      Redhead Asian shemale all covered in pain gets fucked
      Extreme Ladyboys
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    • Pleasure Pain Sissy
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    • More maintenance spanking for Kitsy. OTK punishment.
      06:53
      More maintenance spanking for Kitsy. OTK punishment.
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    • Pathetic Maid Apology Riding Crop Self Punishment
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      Pathetic Maid Apology Riding Crop Self Punishment
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    • 25 min of abuse and hard use for the pain whore Alina
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      25 min of abuse and hard use for the pain whore Alina
      alinanightsky
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    • Anal fist fuck faggot love to feel the pain in the ass
      18:18
      Anal fist fuck faggot love to feel the pain in the ass
      Nicole Montero
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    • The sissy pain whore Alina show her skills in self-humiliation and deep throating with dildo
      02:55
      The sissy pain whore Alina show her skills in self-humiliation and deep throating with dildo
      alinanightsky
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    • Sissy Maid Icy Hot Wooden Pony Punishment 2
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      Sissy Maid Icy Hot Wooden Pony Punishment 2
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