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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
      259K 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
      165.9K views
    • Pain Slut Kira
      36:28
      Pain Slut Kira
      Twistedrama
      104.2K views
    • Caning and choking Kitsy
      04:56
      Caning and choking Kitsy
      Kitsy Meow
      77.4K views
    • 116 min degrading of bdsm sissy pain whore Alina
      02:20
      116 min degrading of bdsm sissy pain whore Alina
      alinanightsky
      81.5K views
    • More maintenance spanking for Kitsy. OTK punishment.
      06:53
      More maintenance spanking for Kitsy. OTK punishment.
      Kitsy Meow
      25.6K 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
      7.6K views
    • 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
      30K 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
      42.8K views
    • Sissy Maids Punishment
      07:53
      Sissy Maids Punishment
      Derek6699
      28.7K views
    • Crossdresser enjoys a very painful flogging session in the d
      21:10
      Crossdresser enjoys a very painful flogging session in the d
      eroticfemaledominati
      179.2K views
    • 3 dildos, a crop, clothspins and a horny girl on a bed
      09:09
      3 dildos, a crop, clothspins and a horny girl on a bed
      Bambi Christa
      18.4K views
    • Painful Anal Stretching With Facial
      06:53
      Painful Anal Stretching With Facial
      Chantal Fouet
      5.4K views
    • Sadistic vampire Mistress
      05:41
      Sadistic vampire Mistress
      Jazebel
      8.1K views
    • FtM stuffed and whipped painfully
      07:06
      FtM stuffed and whipped painfully
      1.3K 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
      7.2K views
    • Moira Zweit. Anal fisting, huge dildo, painful Ball busting
      12:23
      Moira Zweit. Anal fisting, huge dildo, painful Ball busting
      Moira_Moet
      2.7K views
    • No pain no sissy gain
      01:32
      No pain no sissy gain
      Kittykisses96
      5.3K views
    • Denise Humain in bath Final hard self spanking and nipple pain
      23:11
      Denise Humain in bath Final hard self spanking and nipple pain
      Denise Humain
      8.9K views
    • Morning Procedures - bathing in sheer lingerie and painful anal stretching
      06:36
      Morning Procedures - bathing in sheer lingerie and painful anal stretching
      Chantal Fouet
      6.1K views
    • Tyche_Toxic Winces In Pain During Self CBT
      01:14
      Tyche_Toxic Winces In Pain During Self CBT
      Tyche Toxic
      5.7K 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
      5.1K views
    • Rebeccas Perversions 10
      05:35
      Rebeccas Perversions 10
      Rebeccafuxx
      1.4K views
    • Pink psycho bath bondage
      05:37
      Pink psycho bath bondage
      Jazebel
      5.4K views
    • Spanking myself a bit!
      02:33
      Spanking myself a bit!
      Bambi Christa
      4K views
    • sissy slut punishing herself with a paddle
      02:49
      sissy slut punishing herself with a paddle
      Emma Huntcock
      3.8K views
    • Sissy tortured with wax
      02:59
      Sissy tortured with wax
      Sissy_Nadiene
      1.3K views
    • 1 Painful Fuck Session. Shemale Big Cock Fuck a Guy, AAIIGRR
      01:48
      1 Painful Fuck Session. Shemale Big Cock Fuck a Guy, AAIIGRR
      997.7K views
    • Hung Ts Aakosha Bentley makes her sub scream in pain
      02:03
      Hung Ts Aakosha Bentley makes her sub scream in pain
      930.5K views
    • Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune
      13:12
      Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune
      Fiona Fortune
      230.5K views
    • Painting tranny
      07:53
      Painting tranny
      673.8K views
    • Hunter boyfriend gave the pain of in the bathroom
      21:53
      Hunter boyfriend gave the pain of in the bathroom
      Redroseromance
      2.3M views
    • Sexy Asian Big Cock Shemale likes to fuck and give pain to big Ass Porn Star Magic Michel deep anal
      10:05
      Sexy Asian Big Cock Shemale likes to fuck and give pain to big Ass Porn Star Magic Michel deep anal
      Legacy Mess
      114.4K views
    • Sfmnewbie delicious tasty pussy swallowing huge big giant cock sweet pleasure painful gaping pussy hardcore intense ass thirsty
      03:30
      Sfmnewbie delicious tasty pussy swallowing huge big giant cock sweet pleasure painful gaping pussy hardcore intense ass thirsty
      HatanoMiwa
      414.6K views
    • 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
      285.5K views
    • Teen Gets Her 1st Painful Screaming Anal But Let Her Finish
      10:28
      Teen Gets Her 1st Painful Screaming Anal But Let Her Finish
      106.1K views
    • Sfmnewbie delicious and painful intense anal sex hot big ass tasty swallowing big dick anal sweet intense pleasure gaping ass
      04:04
      Sfmnewbie delicious and painful intense anal sex hot big ass tasty swallowing big dick anal sweet intense pleasure gaping ass
      HatanoMiwa
      112.6K views
    • Pain and pleasure, chastity and lust, Part 2
      01:15:02
      Pain and pleasure, chastity and lust, Part 2
      347.2K views
    • Pain Is Her Pleasure
      14:58
      Pain Is Her Pleasure
      kinkts
      1M views
    • Pain and Pleasure  Part 2
      01:15:03
      Pain and Pleasure Part 2
      264.8K views
    • Transgender Pain Slut Strokes Off With Nipple Clamps For Whorish Reasons
      08:01
      Transgender Pain Slut Strokes Off With Nipple Clamps For Whorish Reasons
      Linzy19
      72.1K views
    • 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
      Candy Ass Sissy
      68K views
    • Pain and pleasure, chastity and lust,  Part 1
      51:35
      Pain and pleasure, chastity and lust, Part 1
      129.4K views
    • she puts her bikini aside and fucks him in painful doggy
      03:20
      she puts her bikini aside and fucks him in painful doggy
      218.3K views
    • DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      02:37
      DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      238.3K views
    • Compilation with Weekly Episodes from the pain whore Alina
      02:05
      Compilation with Weekly Episodes from the pain whore Alina
      alinanightsky
      67.8K views
    • Pleasure and pain 2
      26:26
      Pleasure and pain 2
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