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    Morning Procedures - bathing in sheer lingerie and painful anal stretching
    06:36
    Morning Procedures - bathing in sheer lingerie and painful anal stretching
    Chantal Fouet
    4K views
    116 min degrading of bdsm sissy pain whore Alina
    02:20
    116 min degrading of bdsm sissy pain whore Alina
    alinanightsky
    53.2K 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 Slut Kira
    36:28
    Pain Slut Kira
    Twistedrama
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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
    21K 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
    3.7K views
    No pain no sissy gain
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    No pain no sissy gain
    Kittykisses96
    3.1K views
    Sadistic vampire Mistress
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    Sadistic vampire Mistress
    Jazebel
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    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
    5.5K views
    Spanking myself a bit!
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    Spanking myself a bit!
    Bambi Christa
    2.9K views
    Caning and choking Kitsy
    04:56
    Caning and choking Kitsy
    Kitsy Meow
    55.5K views
    More maintenance spanking for Kitsy. OTK punishment.
    06:53
    More maintenance spanking for Kitsy. OTK punishment.
    Kitsy Meow
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    Sissy Maids Punishment
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    Sissy Maids Punishment
    Derek6699
    18.9K 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
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    Nipple Play Found Object FTM Hairy Tit Smacking
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    Nipple Play Found Object FTM Hairy Tit Smacking
    Lyla Switch
    5K views
    Pink psycho bath bondage
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    Pink psycho bath bondage
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    FtM bonus Toy : 100 cunt slaps
    03:23
    FtM bonus Toy : 100 cunt slaps
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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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    I am a naughty bitch that needs to be punished severely
    06:39
    I am a naughty bitch that needs to be punished severely
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    Femboy slut gets hard ass spanking as punishment (SissySandyy20 Solo)
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    Femboy slut gets hard ass spanking as punishment (SissySandyy20 Solo)
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    sissy slut punishing herself with a paddle
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    sissy slut punishing herself with a paddle
    Emma Huntcock
    2.6K views
    Sissy tortured with wax
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    Sissy tortured with wax
    Sissy_Nadiene
    465 views
    HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-
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    HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-
    79K views
    fucking my femboy slave sissy slut painful anal
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    fucking my femboy slave sissy slut painful anal
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    Painful Anal Training On My Sissy Bitch Outdoors with 8inch Dildo
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    Painful Anal Training On My Sissy Bitch Outdoors with 8inch Dildo
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    Young Goth Trans Does Painful Anal
    06:12
    Young Goth Trans Does Painful Anal
    Khatara Shikiku
    5.2K views
    Step-sister pinkish Jim got long painful anal with squirting on her engagement in the morning time
    03:36
    Step-sister pinkish Jim got long painful anal with squirting on her engagement in the morning time
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    Painful Anal with a huge vegetable
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    Painful Anal with a huge vegetable
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    CdTina painful anal
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    CdTina painful anal
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    desi cd boy painful anal play
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    desi cd boy painful anal play
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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
    Fiona Fortune
    23.9K 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
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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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    Pain and Pleasure Part 2
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    Pain and Pleasure Part 2
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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
    Candy Ass Sissy
    39.5K views
    25 min of abuse and hard use for the pain whore Alina
    03:04
    25 min of abuse and hard use for the pain whore Alina
    alinanightsky
    22.9K 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
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    303.6K views
    DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
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    DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
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    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
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    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
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    Compilation with Weekly Episodes from the pain whore Alina
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    Compilation with Weekly Episodes from the pain whore Alina
    alinanightsky
    35.2K 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
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    Lisa Femelle - The Whore of Master pain-
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    Lisa Femelle - The Whore of Master pain-
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    Boss tranny show him his painful role
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    Boss tranny show him his painful role
    XXL4XXL
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    some fun kitty playtime
    16:17
    some fun kitty playtime
    Kittykisses96
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    My patient was complaining of pain in his leg, so I treated him to butt tea at my office desk
    06:06
    My patient was complaining of pain in his leg, so I treated him to butt tea at my office desk
    Nathalia Fontes
    80.8K views
    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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