Painful Punishment Porn Videos

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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
    105.6K 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
    12.7K views
    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    18:39
    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    Derek6699
    58.8K views
    Caning and choking Kitsy
    04:56
    Caning and choking Kitsy
    Kitsy Meow
    50.2K 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
    14.4K views
    How a Tgirl severely punishs her big cock.
    10:29
    How a Tgirl severely punishs her big cock.
    MyLolaTrav
    21.9K views
    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
    19.3K views
    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
    36.6K views
    More maintenance spanking for Kitsy. OTK punishment.
    06:53
    More maintenance spanking for Kitsy. OTK punishment.
    Kitsy Meow
    4.5K views
    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
    2K views
    How to torture a beautiful sissy cock
    09:59
    How to torture a beautiful sissy cock
    MyLolaTrav
    20.1K views
    Sissy Maid Icy Hot Wooden Pony Punishment 2
    23:29
    Sissy Maid Icy Hot Wooden Pony Punishment 2
    Derek6699
    26.5K 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
    10.8K views
    Sissy Maids Punishment
    07:53
    Sissy Maids Punishment
    Derek6699
    16.8K views
    Mistress Cy IPL Hair Removal Punishment
    07:02
    Mistress Cy IPL Hair Removal Punishment
    Cyanide Mistress Of Darkness
    10.7K 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
    5.1K views
    Icy Hot Wooden Pony Self Bondage Torture
    17:40
    Icy Hot Wooden Pony Self Bondage Torture
    Derek6699
    17.1K views
    dumb slut gets the belt for cumming without permission
    04:08
    dumb slut gets the belt for cumming without permission
    Bambi Christa
    7.2K views
    A sissy tortures her buttocks severely with nettles, ties up her balls, dildoes herself and makes herself cum with the vibrator
    18:03
    A sissy tortures her buttocks severely with nettles, ties up her balls, dildoes herself and makes herself cum with the vibrator
    MyLolaTrav
    4.2K views
    The Pressure of Pain and Punishment
    03:41
    The Pressure of Pain and Punishment
    BadGod
    3.3K views
    FtM boy punished for being lazy
    05:10
    FtM boy punished for being lazy
    BonusholeToy
    2.5K views
    Candle Wax & Chastity Go Together like PB & Jelly
    07:05
    Candle Wax & Chastity Go Together like PB & Jelly
    MJ
    3.1K views
    (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
    6.9K views
    Domination and pain with this 2 shemales hardcore punishment
    10:07
    Domination and pain with this 2 shemales hardcore punishment
    Latina Tranny
    27.4K views
    Little sluts bills punishment
    10:18
    Little sluts bills punishment
    Lizz_ss25
    4.3K 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
    3.4K views
    Tabasco Dildo Punishment for forgetting my butt plug today...
    02:50
    Tabasco Dildo Punishment for forgetting my butt plug today...
    Sissy-Hinata
    1.6K views
    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
    3K views
    Masochistic tranny whips himself with flogger
    05:11
    Masochistic tranny whips himself with flogger
    Keeno666
    1.4K views
    Hot Wax On Sissy Cock
    04:15
    Hot Wax On Sissy Cock
    SubmissiveFetish
    3K views
    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
    2.8K views
    DRIPPING HOT WAX ON MY COCK
    05:57
    DRIPPING HOT WAX ON MY COCK
    Kenzie Star
    4K views
    Tyche_Toxic Winces In Pain During Self CBT
    01:14
    Tyche_Toxic Winces In Pain During Self CBT
    Tyche Toxic
    3.9K views
    Painful nipple torture chains
    09:19
    Painful nipple torture chains
    1.3K views
    Shemale cock and nipples pain...
    06:02
    Shemale cock and nipples pain...
    MyLolaTrav
    2.7K 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
    5K views
    sissy slut punishing herself with a paddle
    02:49
    sissy slut punishing herself with a paddle
    Emma Huntcock
    2.4K views
    Sissy tortured with wax
    02:59
    Sissy tortured with wax
    Sissy_Nadiene
    372 views
    FtM punished fir being lazy
    05:12
    FtM punished fir being lazy
    BonusholeToy
    925 views
    Cock Punishment
    00:07
    Cock Punishment
    SubmissiveFetish
    1.3K views
    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
    70K views
    116 min degrading of bdsm sissy pain whore Alina
    02:20
    116 min degrading of bdsm sissy pain whore Alina
    alinanightsky
    33.3K 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
    568.6K views
    Painting tranny
    07:53
    Painting tranny
    414.6K views
    Pain and Pleasure Part 2
    01:15:03
    Pain and Pleasure Part 2
    201K views
    Pain and pleasure, chastity and lust, Part 2
    01:15:02
    Pain and pleasure, chastity and lust, Part 2
    267.9K views
    Pain Is Her Pleasure
    14:58
    Pain Is Her Pleasure
    Kink
    925.6K views

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