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    This Dildo Hurts!
    07:07
    This Dildo Hurts!
    Subby Kim
    10.5K 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
    23.8K views
    Tranny's sore asshole is torn by a huge anal dildo in the bathroom
    05:06
    Tranny's sore asshole is torn by a huge anal dildo in the bathroom
    Dicktrassy dicktrassy
    7.8K views
    I want to lick a black dick and then put it in my ass. I want to drink milk, I am bored. That's my ass hurting. I want a black penis that relieves me of honey.
    01:10
    I want to lick a black dick and then put it in my ass. I want to drink milk, I am bored. That's my ass hurting. I want a black penis that relieves me of honey.
    Zwiml_oficaill
    1K views
    Young Goth Trans Does Painful Anal
    06:12
    Young Goth Trans Does Painful Anal
    Khatara Shikiku
    4.4K views
    This big fat strapon dildo will hurt at first
    09:38
    This big fat strapon dildo will hurt at first
    Sissy Instruction
    15.9K views
    Anal Training. First Time Using Big Dildo. I Give Up, That's Hurt
    01:52
    Anal Training. First Time Using Big Dildo. I Give Up, That's Hurt
    MaureenNadh
    32.5K views
    Up Close Painful Femboy Dildo Practice
    01:04
    Up Close Painful Femboy Dildo Practice
    Khatara Shikiku
    2.8K views
    Fucking my sore butthole with dildo.
    01:22
    Fucking my sore butthole with dildo.
    everydeygrey
    2.8K views
    Just got new toy realy big and it hurts lol...had to try it
    22:42
    Just got new toy realy big and it hurts lol...had to try it
    Xi Liang
    4.3K views
    Sissy Anal Close up of 8 plus inches it hurts so good
    10:15
    Sissy Anal Close up of 8 plus inches it hurts so good
    1.8K views
    Putting this humongous dildo in my ass hurt
    04:17
    Putting this humongous dildo in my ass hurt
    FeelingFull
    1.5K 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
    563.7K views
    BLACK SHEMALE COCK DOES HURT
    01:16
    BLACK SHEMALE COCK DOES HURT
    479.6K views
    This GIANT TS RAW COCK will HURT!!!
    00:41
    This GIANT TS RAW COCK will HURT!!!
    317.3K views
    She'll give him a sore ass and weak legs
    01:53
    She'll give him a sore ass and weak legs
    160.6K views
    Blond angel tranny can't take this painal anymore
    07:11
    Blond angel tranny can't take this painal anymore
    63.7K views
    Please don't daddy, it hurts! He disregards it and fucks his crying pussy hard!
    01:12
    Please don't daddy, it hurts! He disregards it and fucks his crying pussy hard!
    12.9K views
    Boss tranny show him his painful role
    02:17
    Boss tranny show him his painful role
    XXL4XXL
    29K views
    fucking my femboy slave sissy slut painful anal
    01:33
    fucking my femboy slave sissy slut painful anal
    111.1K views
    Came so hard it hurts! Closeups and cum in mouth! (Astra and Nicky shemale on female amateur webcam couple)
    06:51
    Came so hard it hurts! Closeups and cum in mouth! (Astra and Nicky shemale on female amateur webcam couple)
    Astra DIsaster
    90.2K views
    A Sissy Painslut Slave Is Born!
    14:44
    A Sissy Painslut Slave Is Born!
    31.3K 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
    53.6K views
    Stretch Nipples with special tool , VERY PAINFULL !!
    08:34
    Stretch Nipples with special tool , VERY PAINFULL !!
    11.9K views
    Goddess TS Foxxy's Painal Slave
    07:26
    Goddess TS Foxxy's Painal Slave
    Kink
    207.7K 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
    5K views
    Ass-to-Mouth Painful Sissy Bareback Fuck in Motel
    05:55
    Ass-to-Mouth Painful Sissy Bareback Fuck in Motel
    29.6K views
    ts cock this big is gonna hurt
    07:23
    ts cock this big is gonna hurt
    50.5K views
    My asshole hurt a lot but I enjoyed it very much
    05:09
    My asshole hurt a lot but I enjoyed it very much
    cd_aysemmm
    3K views
    Cum hurt me!
    03:29
    Cum hurt me!
    Victoria Lecherri
    3.4K views
    My huge tranny cock is going to hurt a little at first
    14:37
    My huge tranny cock is going to hurt a little at first
    Tranny Newbies
    57.3K views
    painful anal stretching and outdoor cumshot
    04:34
    painful anal stretching and outdoor cumshot
    Chantal Fouet
    3.6K views
    Big Black Cocks Really hurts
    05:07
    Big Black Cocks Really hurts
    cd_aysemmm
    3.2K views
    Slutypia rides first time ass wide open it hurts so good
    00:53
    Slutypia rides first time ass wide open it hurts so good
    7.7K 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
    1.3K views
    Your tight white ass is going to be sore for a week
    15:19
    Your tight white ass is going to be sore for a week
    Tranny Newbies
    1.2K views
    A quickie during the game never hurts
    06:11
    A quickie during the game never hurts
    16.8K views
    Sissy painful chastity cage cumshot with hair clip
    01:00
    Sissy painful chastity cage cumshot with hair clip
    Sorona
    4.4K views
    It hurt so much but I put it all inside
    05:07
    It hurt so much but I put it all inside
    cd_aysemmm
    1.5K views
    CdTina painful anal
    01:37
    CdTina painful anal
    2.5K views
    Kinky iris with new spike clamps, very painfull first time
    06:52
    Kinky iris with new spike clamps, very painfull first time
    8.3K views
    Ouch feels good ouch!
    23:56
    Ouch feels good ouch!
    14.8K views
    Tgirl Scarlette is so horny that it hurts
    00:59
    Tgirl Scarlette is so horny that it hurts
    1.5K views
    Hurts so good
    08:44
    Hurts so good
    33.2K views
    Femmby hurts their dick and has a painful ruined orgasm
    05:08
    Femmby hurts their dick and has a painful ruined orgasm
    2K views
    DGB - TRANNY GAY GREEN HIGH HEELS PAINFULL ANAL - ASS GAPING
    09:55
    DGB - TRANNY GAY GREEN HIGH HEELS PAINFULL ANAL - ASS GAPING
    2.8K views
    It hurts so good.
    00:13
    It hurts so good.
    3.3K views
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