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    Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
    08:09
    Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
    Kitsy Meow
    71.3K views
    Redhead Asian shemale all covered in pain gets fucked
    07:10
    Redhead Asian shemale all covered in pain gets fucked
    Extreme Ladyboys
    39.7K views
    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
    63.8K views
    Daddy domination over his sissy sex slave and to taught her that my place is under his balls
    02:46
    Daddy domination over his sissy sex slave and to taught her that my place is under his balls
    alinanightsky
    3.2K views
    pain turns me on
    01:14
    pain turns me on
    boobyb0y
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    Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots
    17:38
    Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots
    Derek6699
    48.7K views
    Caning and choking Kitsy
    04:56
    Caning and choking Kitsy
    Kitsy Meow
    47.3K views
    116 min degrading of bdsm sissy pain whore Alina
    02:20
    116 min degrading of bdsm sissy pain whore Alina
    alinanightsky
    7.2K views
    Sissy faggot bitch
    11:32
    Sissy faggot bitch
    Sissy Cindy Slut
    5.5K views
    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
    12K views
    Sissy Maid Icy Hot Wooden Pony Punishment 2
    23:29
    Sissy Maid Icy Hot Wooden Pony Punishment 2
    Derek6699
    25.3K views
    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
    9.3K views
    Compilation with Weekly Episodes from the pain whore Alina
    02:05
    Compilation with Weekly Episodes from the pain whore Alina
    alinanightsky
    8.6K views
    Trans Girl plays with an 18 cm Dildo for the first time, Moans from pain but ends up liking it Succubo16
    29:58
    Trans Girl plays with an 18 cm Dildo for the first time, Moans from pain but ends up liking it Succubo16
    LaRicura16
    4.6K views
    Kylie's prediciment
    10:55
    Kylie's prediciment
    Kylie Lynn
    9.6K views
    Icy Hot Wooden Pony Self Bondage Torture
    17:40
    Icy Hot Wooden Pony Self Bondage Torture
    Derek6699
    16.2K 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
    51.4K views
    Ass-to-Mouth Painful Sissy Bareback Fuck in Motel
    05:55
    Ass-to-Mouth Painful Sissy Bareback Fuck in Motel
    29.2K views
    Sissy Nipple Cow Chastity Nipple Pump Electro Pain
    02:06
    Sissy Nipple Cow Chastity Nipple Pump Electro Pain
    Titten-Sau
    15.1K views
    Candle Wax & Chastity Go Together like PB & Jelly
    07:05
    Candle Wax & Chastity Go Together like PB & Jelly
    MJ
    2.7K 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
    3.9K views
    TS_ScarlettRose struggles to take it!
    00:37
    TS_ScarlettRose struggles to take it!
    forsakinsin
    8.8K views
    Thick Anal Viring Gets Her 1st Time Very PAinful & Begging
    17:02
    Thick Anal Viring Gets Her 1st Time Very PAinful & Begging
    41.9K views
    Girl loves pain and cum
    10:00
    Girl loves pain and cum
    12.8K views
    Sissy Maid - Pain & Pleasure Bondage
    14:55
    Sissy Maid - Pain & Pleasure Bondage
    Derek6699
    8.8K views
    Sweet Anal Pain for Solo Sissy CD
    05:00
    Sweet Anal Pain for Solo Sissy CD
    Regina Blasegern
    8.8K views
    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
    4.1K views
    Sissy slut in pain
    01:18
    Sissy slut in pain
    SissyPropertyUk
    8.2K views
    Up Close Painful Femboy Dildo Practice
    01:04
    Up Close Painful Femboy Dildo Practice
    Khatara Shikiku
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    Little sluts bills punishment
    10:18
    Little sluts bills punishment
    Lizz_ss25
    3.9K views
    Young Goth Trans Does Painful Anal
    06:12
    Young Goth Trans Does Painful Anal
    Khatara Shikiku
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    Labor Pains
    01:23
    Labor Pains
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    Hot Wax On Sissy Cock
    04:15
    Hot Wax On Sissy Cock
    SubmissiveFetish
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    Ladyboy Lisa 3 Pain And Pleasure
    06:12
    Ladyboy Lisa 3 Pain And Pleasure
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    21.6K views
    The Pressure of Pain and Punishment
    03:41
    The Pressure of Pain and Punishment
    BadGod
    2.8K views
    Pain and Joy 2
    00:59
    Pain and Joy 2
    Pai-chan
    1.3K views
    First try for new plug and a bit bigger
    01:28
    First try for new plug and a bit bigger
    Sanne
    4.3K views
    Artist. Nithes (hard and Painful Sex, Big Thick and Milky Cock with Rich Testicles)
    00:46
    Artist. Nithes (hard and Painful Sex, Big Thick and Milky Cock with Rich Testicles)
    StrightAss
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    Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 4 - 4
    10:24
    Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 4 - 4
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    3.4K views
    Denise Humain Scene Mix (Anal, Nipple, Blowjob)
    17:28
    Denise Humain Scene Mix (Anal, Nipple, Blowjob)
    Denise Humain
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    cd tranny getting anal pain pounding by fucking machine
    00:57
    cd tranny getting anal pain pounding by fucking machine
    Sasha Earth
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    Deepthroat Blowjob Training and Wax on Tits and Nipples
    17:10
    Deepthroat Blowjob Training and Wax on Tits and Nipples
    Denise Humain
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    Ifetfuc chastity devices and ball stretching toys. Humiliation as he is turned to a sissy for mistress. Painful.
    00:29
    Ifetfuc chastity devices and ball stretching toys. Humiliation as he is turned to a sissy for mistress. Painful.
    iFetFuc
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    Tight Ass Shemale Reign Swallow 12 Inch BBC Deep Up Her Ass
    00:40
    Tight Ass Shemale Reign Swallow 12 Inch BBC Deep Up Her Ass
    Soloregin
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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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    Slut cd using stiging nettles.
    00:44
    Slut cd using stiging nettles.
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    Cock Punishment
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    Cock Punishment
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