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    Spanking myself a bit!
    02:33
    Spanking myself a bit!
    Bambi Christa
    3K views
    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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    Carlee Impaled on HUGE BBC Dildo
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    Carlee Impaled on HUGE BBC Dildo
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    Linday Loves Pain
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    Linday Loves Pain
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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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    pain turns me on
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    pain turns me on
    boobyb0y
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    25 min of abuse and hard use for the pain whore Alina
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    25 min of abuse and hard use for the pain whore Alina
    alinanightsky
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    Redhead Asian shemale all covered in pain gets fucked
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    Redhead Asian shemale all covered in pain gets fucked
    Extreme Ladyboys
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    Black blow up spiked butt plug for my S&M Daddies!
    08:37
    Black blow up spiked butt plug for my S&M Daddies!
    Victoria Lecherri
    28.8K views
    Anal fist fuck faggot love to feel the pain in the ass
    18:18
    Anal fist fuck faggot love to feel the pain in the ass
    Nicole Montero
    119.6K views
    Transgender Slut Lilith Eclipse Fisting Herself and Playing With Her Asshole in a tiny Chastity Cage and Dark Pantyhose
    10:12
    Transgender Slut Lilith Eclipse Fisting Herself and Playing With Her Asshole in a tiny Chastity Cage and Dark Pantyhose
    Lilith_Eclipse
    18.7K views
    Belted sissy pain-slut
    00:27
    Belted sissy pain-slut
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    Ass-to-Mouth Painful Sissy Bareback Fuck in Motel
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    Ass-to-Mouth Painful Sissy Bareback Fuck in Motel
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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
    2K views
    First try for new plug and a bit bigger
    01:28
    First try for new plug and a bit bigger
    Sanne
    6K views
    I need the pain in my ass
    30:28
    I need the pain in my ass
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    TS Pain getting freaky ass
    03:32
    TS Pain getting freaky ass
    5.7K views
    Electro Plug slips all the way in
    03:37
    Electro Plug slips all the way in
    Anyankah Renee Athanasia
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    Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 2 - 4
    02:02
    Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 2 - 4
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    Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 3 - 4
    08:03
    Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 3 - 4
    Denise Humain
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    cd tranny getting anal pain pounding by fucking machine
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    cd tranny getting anal pain pounding by fucking machine
    Sasha Earth
    9K views
    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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    Sweet Anal Pain for Solo Sissy CD
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    Sweet Anal Pain for Solo Sissy CD
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    9.7K views
    Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 1 - 4
    02:16
    Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 1 - 4
    Denise Humain
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    Slut taking pain
    00:29
    Slut taking pain
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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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    Pain Is Her Pleasure
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    Pain Is Her Pleasure
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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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    HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-
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    HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-
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    Pleasure and pain 2
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    Pleasure and pain 2
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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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    Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
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    Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
    Denise Humain
    19.3K views
    Painful nice big cock
    01:57
    Painful nice big cock
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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
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    How to Give Pain and Pleasure to a Big Sissy Cock
    11:41
    How to Give Pain and Pleasure to a Big Sissy Cock
    MyLolaTrav
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    Sissy Nipple Cow Chastity Nipple Pump Electro Pain
    02:06
    Sissy Nipple Cow Chastity Nipple Pump Electro Pain
    Titten-Sau
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    Painful constant wanking after chastity phase! Tranny Girl has 9 (!) ruined orgasms and 5 cumshots!!
    00:43
    Painful constant wanking after chastity phase! Tranny Girl has 9 (!) ruined orgasms and 5 cumshots!!
    Allmylinks
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    A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
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    A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
    Denise Humain
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    Working on Sissy Slave Denise Humain Nipples for hours Part 1
    10:01
    Working on Sissy Slave Denise Humain Nipples for hours Part 1
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    Sissy training Extreme CBT electric shock cock pain bdsm
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    Sissy training Extreme CBT electric shock cock pain bdsm
    iFetFuc
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    Synnz & Mistress Cy "50 Shades of Fucked Up" Shemale Tattoo BDSM Kink Fuck Session (FULL RELEASE)
    01:29:00
    Synnz & Mistress Cy "50 Shades of Fucked Up" Shemale Tattoo BDSM Kink Fuck Session (FULL RELEASE)
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    School Uniform Painful Dragon Dildo Fuck
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    School Uniform Painful Dragon Dildo Fuck
    PrincessKitti3
    just added
    got a new toy with electro shock and vibrating function
    08:24
    got a new toy with electro shock and vibrating function
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    Urethral sounding and vibration of a caged and bound shemale
    08:09
    Urethral sounding and vibration of a caged and bound shemale
    MyLolaTrav
    18K views
    The Pressure of Pain and Punishment
    03:41
    The Pressure of Pain and Punishment
    BadGod
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    Sissy Maid - Pain & Pleasure Bondage
    14:55
    Sissy Maid - Pain & Pleasure Bondage
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