PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels

    Deep Painful Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Anna Loves Shemale 2: Big Veiny Shemale Wrecks My Throat and Ass (e02p01)
      08:58
      Anna Loves Shemale 2: Big Veiny Shemale Wrecks My Throat and Ass (e02p01)
      Anna Loves Shemale
      2.6M 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
      97.3K views
    • anything
      09:14
      anything
      1.4M views
    • DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      02:37
      DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      230.6K 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
      65.5K 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
      27.6K views
    • Turning a straight man into a passive little whore by passionately fucking him with my big cock
      06:15
      Turning a straight man into a passive little whore by passionately fucking him with my big cock
      DotadaSP
      1.4M views
    • Extreme Anal Insertion Two Foot Long XXL Anal Slink
      10:11
      Extreme Anal Insertion Two Foot Long XXL Anal Slink
      TheToxicTwins
      45.1K views
    • Big Ass Blond TS Screams as Monster Cock BBC Daddy Destroys
      09:51
      Big Ass Blond TS Screams as Monster Cock BBC Daddy Destroys
      Candy Ass Sissy
      186.3K views
    • Tight Ass Shemale Reign Swallow 12 Inch BBC Deep Up Her Ass
      00:40
      Tight Ass Shemale Reign Swallow 12 Inch BBC Deep Up Her Ass
      Soloregin
      3.6K 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
      171.3K views
    • Hung Ts Aakosha Bentley makes her sub scream in pain
      02:03
      Hung Ts Aakosha Bentley makes her sub scream in pain
      907.7K views
    • Anna LovesShemale 1: BDSM Play with Tattooed Trans Beauty (e01p01)
      13:12
      Anna LovesShemale 1: BDSM Play with Tattooed Trans Beauty (e01p01)
      Anna Loves Shemale
      672.8K 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
      215.1K 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
      962.3K views
    • Painting tranny
      07:53
      Painting tranny
      650.7K views
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.3M views
    • Hunter boyfriend gave the pain of in the bathroom
      21:53
      Hunter boyfriend gave the pain of in the bathroom
      Redroseromance
      2.1M views
    • Tranny model Rakel Rodrigues gets tied up and fucked by
      07:56
      Tranny model Rakel Rodrigues gets tied up and fucked by
      Tranny Edge
      114.5K 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
      400.6K views
    • Penis pump and BDSM stuff makes this T-girl horny as fuck
      06:14
      Penis pump and BDSM stuff makes this T-girl horny as fuck
      301.2K 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
      98.7K views
    • When you Don't Want Anymore But Master Still Gives You
      02:20
      When you Don't Want Anymore But Master Still Gives You
      973.3K 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
      273.6K views
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3M views
    • Pain Slut Kira
      36:28
      Pain Slut Kira
      Twistedrama
      100.2K views
    • Cruel shemale use her XXL dick on him
      02:25
      Cruel shemale use her XXL dick on him
      XXL4XXL
      748.3K views
    • Pain Is Her Pleasure
      14:58
      Pain Is Her Pleasure
      kinkts
      1M views
    • Anna Loves Shemale 3: Exotic Tranny Got That ULTRA-COCK (e03p01)
      07:17
      Anna Loves Shemale 3: Exotic Tranny Got That ULTRA-COCK (e03p01)
      Anna Loves Shemale
      1.7M views
    • Pain and pleasure, chastity and lust, Part 2
      01:15:02
      Pain and pleasure, chastity and lust, Part 2
      340.5K views
    • HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-
      31:02
      HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-
      107.3K 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
      107.1K views
    • Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
      29:33
      Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
      Ria_Bentley
      2.5M views
    • Pain and Pleasure  Part 2
      01:15:03
      Pain and Pleasure Part 2
      260.4K views
    • Tied up shemale with black boots gets fucked doggystyle by a
      08:14
      Tied up shemale with black boots gets fucked doggystyle by a
      Tranny Edge
      136.5K views
    • Pain and pleasure, chastity and lust,  Part 1
      51:35
      Pain and pleasure, chastity and lust, Part 1
      125.2K views
    • The Submissive Whore Had Her Balls Tied and Was Fucked by a Big Dick Black Guy
      03:55
      The Submissive Whore Had Her Balls Tied and Was Fucked by a Big Dick Black Guy
      Wesley Fudedor
      8.6K views
    • Pleasure and pain 2
      26:26
      Pleasure and pain 2
      307.5K 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
      229.6K 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
      213.6K views
    • Girl surprised with big cock in panties
      19:27
      Girl surprised with big cock in panties
      DefianceFilms
      441.3K views
    • Compilation with Weekly Episodes from the pain whore Alina
      02:05
      Compilation with Weekly Episodes from the pain whore Alina
      alinanightsky
      64.5K views
    • Trans Schoolgirl Gabrielly Ferraz Gets Dominated and Pounded
      08:10
      Trans Schoolgirl Gabrielly Ferraz Gets Dominated and Pounded
      Dream Tranny
      2.4M 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
      68.9K views
    • Veronica Leal Surprises Stacy Cruz with Her FUTA Dick and Gets Her Tight Ass Destroyed - FULL SCENE
      12:33
      Veronica Leal Surprises Stacy Cruz with Her FUTA Dick and Gets Her Tight Ass Destroyed - FULL SCENE
      Futanari XXX
      21.3M views
    • fucking my femboy slave sissy slut painful anal
      01:33
      fucking my femboy slave sissy slut painful anal
      130.5K 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
      40.4K views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80

    Categories

    American
    4K Porn
    HD Videos
    VR Porn
    Shemale Fucks Guy
    Big Cock
    Black
    Shemale Fucks Shemale
    Amateur
    Shemale Fucks Girl
    Sissy
    Ladyboy
    Guy Fucks Shemale
    Compilation
    Blowjob
    Cum In Mouth
    Big Black Cock
    Big Ass
    Creampie
    Bareback
    Cumshot
    Homemade
    Mature
    Teen
    Masturbation
    Domination
    Anal
    Brazilian
    Asian
    Solo
    Transgender
    BBW
    Mexican
    Interracial
    Cartoon
    Japanese
    Vintage
    Young
    Big Tits
    Small Cock
    Thai
    Lingerie
    Gangbang
    Trans Woman
    Threesome
    Colombian
    Petite
    Public
    BDSM
    Rough Sex
    Couple
    MILF
    Anal Masturbation
    POV
    Dildo
    Cuckold
    Stockings
    Small Tits
    Babysitter
    Trans Man
    Indian
    Outdoor
    Handjob
    Chinese
    Fetish
    Hentai
    Group Sex
    Massage
    FTM
    Bondage
    British
    Pissing
    Double Penetration
    Role Play
    Behind The Scenes
    German
    Anal Toy
    SFW
    All categories
    Monetize your content
    Become a creator

    xHamster

    • About us
    • 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

    Earn money with us

    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    © 2026 xHamster - Free porn videos.
    Desktop 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