PornPorn Transgender • US
  • Videos
  • Short videos
  • photos
  • Users
    Forgot password
    Sign in with Google
    Sign in with X
    Sign up for free
    Videos
    • Best Videos
    • Short Videos
    • Watch History
    • American
    • Amateur
    • Shemale Fucks Guy
    • Shemale Fucks Girl
    • Big Cock
    • All categories
    Live Sex
    Categories
    • Shemale Fucks Guy
    • Black
    • Big Cock
    • Shemale Fucks Shemale
    • Amateur
    • All categories
    Pornstars
    • Pornstars
    • By Countries
    • xHamster Creators
    Creators
    • Top Creators
    • Top Creator Videos
    • Awards 2025
    • All xHamster Creators
    • By Countries
    • Become a Creator
    Channels
    Photos
    • Ladyboy
    • Tranny
    • Big Cock
    • Thai
    • Blowjob
    • All categories
    Faphouse
    Premium Videos
    Dating
    Subscriptions
    • Upload
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Black
    • Big Cock
    • Shemale Fucks Shemale
    • Amateur
    • Sissy
    • Shemale Fucks Girl
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Big Black Cock
    • Cum In Mouth
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Pain Fisting Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Pain Slut Kira
    36:28
    Pain Slut Kira
    FapHouse
    101.7K views
    some fun kitty playtime
    16:17
    some fun kitty playtime
    Kittykisses96
    21.3K 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
    41.7K views
    BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
    07:34
    BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
    FapHouse
    5.8K views
    BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys
    08:00
    BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys
    FapHouse
    6.3K views
    Moira Zweit. Anal fisting, huge dildo, painful Ball busting
    12:23
    Moira Zweit. Anal fisting, huge dildo, painful Ball busting
    Moira_Moet
    2.5K views
    Transsexual
    35:14
    Transsexual
    MIMEROMOLE
    3.4K views
    Sissy training Extreme CBT electric shock cock pain bdsm
    00:20
    Sissy training Extreme CBT electric shock cock pain bdsm
    iFetFuc
    84.6K views
    Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
    44:10
    Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
    alinanightsky
    241.9K views
    Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune
    13:12
    Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune
    Fiona Fortune
    221.7K views
    Hunter boyfriend gave the pain of in the bathroom
    21:53
    Hunter boyfriend gave the pain of in the bathroom
    Redroseromance
    2.2M 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
    Onlyfans
    102.9K views
    Sfmnewbie delicious tasty pussy swallowing huge big giant cock sweet pleasure painful gaping pussy hardcore intense ass thirsty
    03:30
    Sfmnewbie delicious tasty pussy swallowing huge big giant cock sweet pleasure painful gaping pussy hardcore intense ass thirsty
    HatanoMiwa
    406.5K 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
    276.8K views
    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
    109.2K 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
    162.3K 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
    66.4K 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
    70.3K views
    Compilation with Weekly Episodes from the pain whore Alina
    02:05
    Compilation with Weekly Episodes from the pain whore Alina
    alinanightsky
    65.7K 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
    32K views
    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    18:39
    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    Derek6699
    102.2K 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
    74.9K views
    Caning and choking Kitsy
    04:56
    Caning and choking Kitsy
    Kitsy Meow
    75.7K views
    116 min degrading of bdsm sissy pain whore Alina
    02:20
    116 min degrading of bdsm sissy pain whore Alina
    alinanightsky
    80.1K 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
    58.3K views
    More maintenance spanking for Kitsy. OTK punishment.
    06:53
    More maintenance spanking for Kitsy. OTK punishment.
    Kitsy Meow
    24.4K views
    Slapping My Tits and Ass Like a Good Pain Slut
    08:55
    Slapping My Tits and Ass Like a Good Pain Slut
    FapHouse
    6.6K views
    25 min of abuse and hard use for the pain whore Alina
    03:04
    25 min of abuse and hard use for the pain whore Alina
    alinanightsky
    53.9K views
    Sissy Denise: Tied Nipples Tortured with Rough Round Brushes
    18:54
    Sissy Denise: Tied Nipples Tortured with Rough Round Brushes
    Denise Humain
    2.8K 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
    28.9K views
    How a Tgirl severely punishs her big cock.
    10:29
    How a Tgirl severely punishs her big cock.
    MyLolaTrav
    43.6K views
    How to torture a beautiful sissy cock
    09:59
    How to torture a beautiful sissy cock
    MyLolaTrav
    27.4K views
    Sissy Maid Icy Hot Wooden Pony Punishment 2
    23:29
    Sissy Maid Icy Hot Wooden Pony Punishment 2
    Derek6699
    39.8K 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
    112.6K 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.
    FapHouse
    43.9K views
    Rebeccas Pervertions 8
    11:21
    Rebeccas Pervertions 8
    Rebeccafuxx
    17.3K 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
    44.1K views
    Sissy Nipple Cow Chastity Nipple Pump Electro Pain
    02:06
    Sissy Nipple Cow Chastity Nipple Pump Electro Pain
    Titten-Sau
    26.3K views
    Sissy Denise: Nipple torture with combination pliers – Live until the end
    09:37
    Sissy Denise: Nipple torture with combination pliers – Live until the end
    Denise Humain
    3K views
    Extreme Anal Insertion Two Foot Long XXL Anal Slink
    10:11
    Extreme Anal Insertion Two Foot Long XXL Anal Slink
    Onlyfans
    45.6K views
    School Uniform Painful Dragon Dildo Fuck
    07:15
    School Uniform Painful Dragon Dildo Fuck
    PrincessKitti3
    827 views
    Sissy Maids Punishment
    07:53
    Sissy Maids Punishment
    Derek6699
    28.1K views
    Up Close Painful Femboy Dildo Practice
    01:04
    Up Close Painful Femboy Dildo Practice
    Khatara Shikiku
    6.1K views
    Young Goth Trans Does Painful Anal
    06:12
    Young Goth Trans Does Painful Anal
    Khatara Shikiku
    9.2K views
    Icy Hot Wooden Pony Self Bondage Torture
    17:40
    Icy Hot Wooden Pony Self Bondage Torture
    Derek6699
    26.7K views
    Newest Scene Compilation (with new Stuff) incl. Anal, Gaping, Nipple Pain, Humiliation, Sissy, BDSM, Trans, Denise Humain
    13:53
    Newest Scene Compilation (with new Stuff) incl. Anal, Gaping, Nipple Pain, Humiliation, Sissy, BDSM, Trans, Denise Humain
    Denise Humain
    3.4K 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
    43.6K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 31
    • Next
    xHamster
    • Press
    • Blog
    • Creator's Blog
    • Advertising
    • xHamster Awards 2025
    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 - 2026, xHamster.com
    Mobile Version
    18 U.S.C. 2257 Record-Keeping Requirements Compliance Statement
    RTA Restricted To AdultsRTA Restricted To Adults
    xHamster is adults only website!

    The content available on xHamster may contain pornographic materials.

    xHamster is strictly limited to those over 18 or of legal age in your jurisdiction, whichever is greater.

    One of our core goals is to help parents restrict access to xHamster for minors, so we have ensured that xHamster is, and remains, fully compliant with the RTA (Restricted to Adults) code. This means that all access to the site can be blocked by simple parental control tools. It is important that responsible parents and guardians take the necessary steps to prevent minors from accessing unsuitable content online, especially age-restricted content.

    Anyone with a minor in their household or under their supervision should implement basic parental control protections, including computer hardware and device settings, software installation, or ISP filtering services, to block your minors from accessing inappropriate content.

    To enter xHamster you must be 18 or older
    how to protect your minors
    RTA Restricted To AdultsRTA Restricted To Adults