PornPorn Transgender • US
  • Videos
  • photos
  • Users
    Forgot password
    google
    Sign in with Google
    Sign in with Twitter
    Sign up for free
    Videos
    • Best Videos
    • Moments
    • Watch History
    • American
    • Amateur
    • Shemale Fucks Guy
    • Shemale Fucks Girl
    • Big Cock
    • All categories
    Live Sex
    Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Amateur
    • Shemale Fucks Shemale
    • All categories
    Pornstars
    • Pornstars
    • By Countries
    • xHamster Creators
    Creators
    • Top Creators
    • Top Creator Videos
    • Awards 2024
    • All xHamster Creators
    • By Countries
    • Become a Creator
    Channels
    Photos
    • Ladyboy
    • Tranny
    • Big Cock
    • Thai
    • Blowjob
    • All categories
    Faphouse
    Premium Videos
    Dating
    Free VPN
    Free VPN
    AI Friend
    AI Friend
    Subscriptions
    • Upload
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Amateur
    • Shemale Fucks Shemale
    • Sissy
    • Shemale Fucks Girl
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Bareback
    • Ladyboy
    • Cum In Mouth
    • Big Black Cock
    • Mature
    • Big Ass
    • Creampie
    • Cumshot
    • Teen
    • Domination
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Extreme Painful Porn Videos

    Free Porn Videos
    Paid Videos
    Photos

    Did you mean extreme painal?

    Best Videos
    By clicking the content you will also see an ad.
    More Trans Chat with xHamsterLive trans now!
    Pain Slut Kira
    36:28
    Pain Slut Kira
    Twistedrama
    76.2K 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
    140K views
    Pain and Pleasure  Part 2
    01:15:03
    Pain and Pleasure Part 2
    242.3K views
    Pain and pleasure, chastity and lust, Part 2
    01:15:02
    Pain and pleasure, chastity and lust, Part 2
    313.2K views
    Pain Is Her Pleasure
    14:58
    Pain Is Her Pleasure
    Kink
    976.5K views
    Compilation with Weekly Episodes from the pain whore Alina
    02:05
    Compilation with Weekly Episodes from the pain whore Alina
    alinanightsky
    52.7K views
    116 min degrading of bdsm sissy pain whore Alina
    02:20
    116 min degrading of bdsm sissy pain whore Alina
    alinanightsky
    68.5K views
    Sexy Asian Big Cock Shemale likes to fuck and give pain to big Ass Porn Star Magic Michel deep anal
    10:05
    Sexy Asian Big Cock Shemale likes to fuck and give pain to big Ass Porn Star Magic Michel deep anal
    Legacy Mess
    47K views
    The sissy pain whore Alina show her skills in self-humiliation and deep throating with dildo
    02:55
    The sissy pain whore Alina show her skills in self-humiliation and deep throating with dildo
    alinanightsky
    19.7K views
    she puts her bikini aside and fucks him in painful doggy
    03:20
    she puts her bikini aside and fucks him in painful doggy
    191.7K 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
    77.7K views
    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    18:39
    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    Derek6699
    85K 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
    97.5K views
    HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-
    31:02
    HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-
    95.7K 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
    132.3K views
    Pleasure and pain 2
    26:26
    Pleasure and pain 2
    293.9K views
    Caning and choking Kitsy
    04:56
    Caning and choking Kitsy
    Kitsy Meow
    64.3K views
    Step-sister pinkish Jim got long painful anal with squirting on her engagement in the morning time
    03:36
    Step-sister pinkish Jim got long painful anal with squirting on her engagement in the morning time
    xhtad1
    75.7K views
    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
    64.2K views
    How a Tgirl severely punishs her big cock.
    10:29
    How a Tgirl severely punishs her big cock.
    MyLolaTrav
    36K 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
    31.8K views
    Finishing up with pain on my balls
    04:02
    Finishing up with pain on my balls
    12.1K views
    More maintenance spanking for Kitsy. OTK punishment.
    06:53
    More maintenance spanking for Kitsy. OTK punishment.
    Kitsy Meow
    16.5K 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
    48.7K views
    fucking my femboy slave sissy slut painful anal
    01:33
    fucking my femboy slave sissy slut painful anal
    123.1K views
    Sissy Maid Icy Hot Wooden Pony Punishment 2
    23:29
    Sissy Maid Icy Hot Wooden Pony Punishment 2
    Derek6699
    33.8K views
    Pleasure Pain Sissy
    03:14
    Pleasure Pain Sissy
    43.8K 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
    24.4K views
    Pain and pleasure, chastity and lust,  Part 1
    51:35
    Pain and pleasure, chastity and lust, Part 1
    115K views
    Sissy Maids Punishment
    07:53
    Sissy Maids Punishment
    Derek6699
    23K views
    Redhead asian trans all covered in pain ass fucked
    07:30
    Redhead asian trans all covered in pain ass fucked
    Extreme Ladyboys
    9.2K views
    slave for pain
    00:39
    slave for pain
    41.5K views
    Sissy Nipple Cow Chastity Nipple Pump Electro Pain
    02:06
    Sissy Nipple Cow Chastity Nipple Pump Electro Pain
    Titten-Sau
    22.5K views
    Painful Anal Stretching With Facial
    06:53
    Painful Anal Stretching With Facial
    Chantal Fouet
    2.6K views
    Painful nice big cock
    01:57
    Painful nice big cock
    74.2K 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
    16K views
    Tranny with big cock fucks latino man in the ass
    35:40
    Tranny with big cock fucks latino man in the ass
    EroCom
    21.1K views
    Thick Anal Viring Gets Her 1st Time Very PAinful & Begging
    17:02
    Thick Anal Viring Gets Her 1st Time Very PAinful & Begging
    52.3K views
    Icy Hot Wooden Pony Self Bondage Torture
    17:40
    Icy Hot Wooden Pony Self Bondage Torture
    Derek6699
    22.4K views
    Ass-to-Mouth Painful Sissy Bareback Fuck in Motel
    05:55
    Ass-to-Mouth Painful Sissy Bareback Fuck in Motel
    31.5K views
    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
    38.8K views
    Sissy Maid - Pain & Pleasure Bondage
    14:55
    Sissy Maid - Pain & Pleasure Bondage
    Derek6699
    14.1K views
    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
    14.4K views
    Kisses and pain in intimity
    18:35
    Kisses and pain in intimity
    22.7K views
    Pain free Kitty Kaiti..mega load
    02:13
    Pain free Kitty Kaiti..mega load
    85.9K views
    Lisa Femelle - The Whore of Master pain-
    13:35
    Lisa Femelle - The Whore of Master pain-
    56.8K views
    Sissy slut in pain
    01:18
    Sissy slut in pain
    SissyPropertyUk
    11.2K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next
    Chat with xHamsterLive trans now! More Trans

    xHamster

    • xHamster Shop
    • Press
    • Blog
    • Creator's Blog
    • Advertising
    • xHamster NFT
    • xHamster Awards 2024

    Help

    • FAQ
    • Contact us
    • Content Removal
    • Improve xHamster

    Legal

    • Terms of use
    • Privacy policy
    • Cookies policy
    • DMCA/Copyright
    • Parental Controls
    • EU DSA
    • Trust and Safety

    Start making money with us

    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    Monetize your content
    Become a creator
    © 2007 - 2025, xHamster.com
    Mobile Version
    18 U.S.C. 2257 Record-Keeping Requirements Compliance Statement
    RTA Restricted To AdultsRTA Restricted To Adults