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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
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    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
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    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    Derek6699
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    some fun kitty playtime
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    some fun kitty playtime
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    How a Tgirl severely punishs her big cock.
    10:29
    How a Tgirl severely punishs her big cock.
    MyLolaTrav
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    Caning and choking Kitsy
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    Caning and choking Kitsy
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    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
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    More maintenance spanking for Kitsy. OTK punishment.
    06:53
    More maintenance spanking for Kitsy. OTK punishment.
    Kitsy Meow
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    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
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    How to Give Pain and Pleasure to a Big Sissy Cock
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    How to Give Pain and Pleasure to a Big Sissy Cock
    MyLolaTrav
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    Sissy Maids Punishment
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    Sissy Maids Punishment
    Derek6699
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    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
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    Sissy Maid Icy Hot Wooden Pony Punishment 2
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    Sissy Maid Icy Hot Wooden Pony Punishment 2
    Derek6699
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    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
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    Icy Hot Wooden Pony Self Bondage Torture
    17:40
    Icy Hot Wooden Pony Self Bondage Torture
    Derek6699
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    BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
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    BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
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    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
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    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
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    The Pressure of Pain and Punishment
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    The Pressure of Pain and Punishment
    BadGod
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    dumb slut gets the belt for cumming without permission
    04:08
    dumb slut gets the belt for cumming without permission
    Bambi Christa
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    Candle Wax & Chastity Go Together like PB & Jelly
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    Candle Wax & Chastity Go Together like PB & Jelly
    MJ
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    Tabasco Dildo Punishment for forgetting my butt plug today...
    02:50
    Tabasco Dildo Punishment for forgetting my butt plug today...
    Sissy-Hinata
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    FtM boy punished for being lazy
    05:10
    FtM boy punished for being lazy
    BonusholeToy
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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
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    Domination and pain with this 2 shemales hardcore punishment
    10:07
    Domination and pain with this 2 shemales hardcore punishment
    Latina Tranny
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    Mistress Cy IPL Hair Removal Punishment
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    Mistress Cy IPL Hair Removal Punishment
    Cyanide Mistress Of Darkness
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    Rebecca's painful Orgasm
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    Rebecca's painful Orgasm
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    Little sluts bills punishment
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    Little sluts bills punishment
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    Femboy slut gets hard ass spanking as punishment (SissySandyy20 Solo)
    03:43
    Femboy slut gets hard ass spanking as punishment (SissySandyy20 Solo)
    Sissy Sandy
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    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
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    (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
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    Tyche_Toxic Winces In Pain During Self CBT
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    Tyche_Toxic Winces In Pain During Self CBT
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    Shemale cock and nipples pain...
    06:02
    Shemale cock and nipples pain...
    MyLolaTrav
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    Maso Muslima squirts in Pain
    06:27
    Maso Muslima squirts in Pain
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    Hot Wax On Sissy Cock
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    Hot Wax On Sissy Cock
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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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    Masochistic tranny whips himself with flogger
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    Masochistic tranny whips himself with flogger
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    Painful nipple torture chains
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    Painful nipple torture chains
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    Cock Punishment
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    Cock Punishment
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    Sissy tortured with wax
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    Sissy tortured with wax
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    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
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    1 Painful Fuck Session. Shemale Big Cock Fuck a Guy, AAIIGRR
    01:48
    1 Painful Fuck Session. Shemale Big Cock Fuck a Guy, AAIIGRR
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    Hung Ts Aakosha Bentley makes her sub scream in pain
    02:03
    Hung Ts Aakosha Bentley makes her sub scream in pain
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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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    Painting tranny
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    Painting tranny
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    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
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    Pain and Pleasure Part 2
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    Pain and Pleasure Part 2
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