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    Painting tranny
    07:53
    Painting tranny
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    DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
    02:37
    DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
    154.2K 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
    30.8K views
    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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    Just because I can..
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    Just because I can..
    Twistedrama
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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
    547.3K 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
    99.6K views
    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
    74.8K views
    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    18:39
    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    Derek6699
    54.9K views
    Redhead Asian shemale all covered in pain gets fucked
    07:10
    Redhead Asian shemale all covered in pain gets fucked
    Extreme Ladyboys
    40.7K views
    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
    20.1K 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
    11.8K 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
    35.2K views
    116 min degrading of bdsm sissy pain whore Alina
    02:20
    116 min degrading of bdsm sissy pain whore Alina
    alinanightsky
    17.3K 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
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    FtM bonus Toy : 100 cunt slaps
    03:23
    FtM bonus Toy : 100 cunt slaps
    BonusholeToy
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    Balls stretched masturbation
    04:08
    Balls stretched masturbation
    MyLolaTrav
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    How to torture a beautiful sissy cock
    09:59
    How to torture a beautiful sissy cock
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    Caning and choking Kitsy
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    Caning and choking Kitsy
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    48.2K views
    Transgender Pain Slut Strokes Off With Nipple Clamps For Whorish Reasons
    08:01
    Transgender Pain Slut Strokes Off With Nipple Clamps For Whorish Reasons
    Linzy19
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    How a Tgirl severely punishs her big cock.
    10:29
    How a Tgirl severely punishs her big cock.
    MyLolaTrav
    20.2K views
    Working on Sissy Slave Denise Humain Nipples for hours Part 1
    10:01
    Working on Sissy Slave Denise Humain Nipples for hours Part 1
    Denise Humain
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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
    28K views
    third try with triple penetration toy
    07:35
    third try with triple penetration toy
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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
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    Sissy Maid Icy Hot Wooden Pony Punishment 2
    23:29
    Sissy Maid Icy Hot Wooden Pony Punishment 2
    Derek6699
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    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
    9.8K 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
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    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
    8.7K 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
    4.9K 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
    23.2K 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
    15.7K views
    Selfuking
    04:12
    Selfuking
    Papiricoo
    29.1K views
    pain, pleasure & cum load for T-girl Alexandra
    11:13
    pain, pleasure & cum load for T-girl Alexandra
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    Boss tranny show him his painful role
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    Boss tranny show him his painful role
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    Icy Hot Wooden Pony Self Bondage Torture
    17:40
    Icy Hot Wooden Pony Self Bondage Torture
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    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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    Domination and pain with this 2 shemales hardcore punishment
    10:07
    Domination and pain with this 2 shemales hardcore punishment
    Latina Tranny
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    Horny tranny threesome of fun and pain
    06:42
    Horny tranny threesome of fun and pain
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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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    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
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    Becca squirts in shiny pantyhose
    02:46
    Becca squirts in shiny pantyhose
    Rebeccafuxx
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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
    16.1K views
    Candle Wax & Chastity Go Together like PB & Jelly
    07:05
    Candle Wax & Chastity Go Together like PB & Jelly
    MJ
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    dumb slut gets the belt for cumming without permission
    04:08
    dumb slut gets the belt for cumming without permission
    Bambi Christa
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    FTM fucking a huge dildo and pin orgasm
    02:34
    FTM fucking a huge dildo and pin orgasm
    Ares FTM
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    Sissy Maids Punishment
    07:53
    Sissy Maids Punishment
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