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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
    4.2K 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
    6.9K 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
    124.7K views
    116 min degrading of bdsm sissy pain whore Alina
    02:20
    116 min degrading of bdsm sissy pain whore Alina
    alinanightsky
    58K views
    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
    24.1K views
    Sadistic vampire Mistress
    05:41
    Sadistic vampire Mistress
    Jazebel
    4.1K views
    No pain no sissy gain
    01:32
    No pain no sissy gain
    Kittykisses96
    3.3K 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
    5.8K views
    Spanking myself a bit!
    02:33
    Spanking myself a bit!
    Bambi Christa
    3K views
    More maintenance spanking for Kitsy. OTK punishment.
    06:53
    More maintenance spanking for Kitsy. OTK punishment.
    Kitsy Meow
    11.4K views
    Caning and choking Kitsy
    04:56
    Caning and choking Kitsy
    Kitsy Meow
    57.2K views
    Sissy Maids Punishment
    07:53
    Sissy Maids Punishment
    Derek6699
    20K 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
    12.2K views
    Nipple Play Found Object FTM Hairy Tit Smacking
    05:46
    Nipple Play Found Object FTM Hairy Tit Smacking
    Lyla Switch
    5.4K views
    Pink psycho bath bondage
    05:37
    Pink psycho bath bondage
    Jazebel
    3.3K 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
    5.4K views
    sissy slut punishing herself with a paddle
    02:49
    sissy slut punishing herself with a paddle
    Emma Huntcock
    2.6K views
    Tyche_Toxic Winces In Pain During Self CBT
    01:14
    Tyche_Toxic Winces In Pain During Self CBT
    Tyche Toxic
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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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    FtM bonus Toy : 100 cunt slaps
    03:23
    FtM bonus Toy : 100 cunt slaps
    BonusholeToy
    16.9K views
    Sissy tortured with wax
    02:59
    Sissy tortured with wax
    Sissy_Nadiene
    521 views
    HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-
    31:02
    HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-
    81.7K views
    fucking my femboy slave sissy slut painful anal
    01:33
    fucking my femboy slave sissy slut painful anal
    117.1K views
    Painful Anal Training On My Sissy Bitch Outdoors with 8inch Dildo
    09:57
    Painful Anal Training On My Sissy Bitch Outdoors with 8inch Dildo
    26.6K views
    Young Goth Trans Does Painful Anal
    06:12
    Young Goth Trans Does Painful Anal
    Khatara Shikiku
    5.4K 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
    xhtad1
    22K views
    Painful Anal with a huge vegetable
    01:01
    Painful Anal with a huge vegetable
    9.9K views
    CdTina painful anal
    01:37
    CdTina painful anal
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    desi cd boy painful anal play
    04:17
    desi cd boy painful anal play
    pari_sissyfemboi
    2K 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
    52.6K 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
    658K 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
    32.7K views
    Painting tranny
    07:53
    Painting tranny
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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
    156.8K 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
    312.6K 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
    42.4K views
    Pain and Pleasure Part 2
    01:15:03
    Pain and Pleasure Part 2
    228.6K 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
    67.1K views
    DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
    02:37
    DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
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    Compilation with Weekly Episodes from the pain whore Alina
    02:05
    Compilation with Weekly Episodes from the pain whore Alina
    alinanightsky
    39.1K 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
    26.8K views
    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    18:39
    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    Derek6699
    72.8K 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
    63.7K views
    some fun kitty playtime
    16:17
    some fun kitty playtime
    Kittykisses96
    7.4K views
    Boss tranny show him his painful role
    02:17
    Boss tranny show him his painful role
    XXL4XXL
    38.7K 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
    179K views
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