PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
      -60%
    • Pornstars
    • Channels
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday Sale

    Sex With Pain 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
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.3M views
    • Shemale with leather cloth likes cruel sex with pain in her apartment
      19:49
      Shemale with leather cloth likes cruel sex with pain in her apartment
      92.2K 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
    • A naughty housemaid with ripped black pantyhose tried the thickest dildo into her sissy pussy and moaned with pain and joy
      07:15
      A naughty housemaid with ripped black pantyhose tried the thickest dildo into her sissy pussy and moaned with pain and joy
      Harinni
      3.2K views
    • handz free shemale cumming while getting fucked
      13:40
      handz free shemale cumming while getting fucked
      2.4M views
    • Finishing up with pain on my balls
      04:02
      Finishing up with pain on my balls
      17.2K views
    • Sissy cums too early and gets punished with rough fucking
      02:35
      Sissy cums too early and gets punished with rough fucking
      2.1M views
    • ANAL with PAIN
      01:18
      ANAL with PAIN
      79.7K views
    • I have sex with my ex-boyfriend's transsexual crush
      09:25
      I have sex with my ex-boyfriend's transsexual crush
      NaughtyTrans
      4M 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
      960.8K views
    • Dude takes a tranny painal
      01:16
      Dude takes a tranny painal
      167.7K 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
      212.5K views
    • Big Tits Asian Nurse Finds Out Her Disabled Patient Has A Cock
      11:07
      Big Tits Asian Nurse Finds Out Her Disabled Patient Has A Cock
      Futanari XXX
      7.5M views
    • Hung Ts Aakosha Bentley makes her sub scream in pain
      02:03
      Hung Ts Aakosha Bentley makes her sub scream in pain
      906.3K views
    • 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
    • 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
      224.3K views
    • He Screams For Shemeat Compilation 2020 (TS TOPS)
      15:53
      He Screams For Shemeat Compilation 2020 (TS TOPS)
      2.9M views
    • Painting tranny
      07:53
      Painting tranny
      649.4K views
    • He Tears His Cute Trans Roommate's Pantyhose To Bang Her
      10:54
      He Tears His Cute Trans Roommate's Pantyhose To Bang Her
      Devils tgirls
      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
      95.8K views
    • Afterschool Detention Sex - Tg Shemale Blake Blossom Grows Futa Cock and Fucks Asian Slut
      02:05
      Afterschool Detention Sex - Tg Shemale Blake Blossom Grows Futa Cock and Fucks Asian Slut
      Futanari XXX
      2.1M 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
      398.5K views
    • Shemale Jessy pounces on the busty slut and drives her cock
      06:15
      Shemale Jessy pounces on the busty slut and drives her cock
      Transsensual
      7.2M 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
      271.7K views
    • JockPussy - Petite trans hottie Joey Michaels cumdumps for hung jocks
      10:10
      JockPussy - Petite trans hottie Joey Michaels cumdumps for hung jocks
      Jock Pussy
      2M views
    • Pain Is Her Pleasure
      14:58
      Pain Is Her Pleasure
      kinkts
      1M views
    • I'll fill your asshole with cum to overflowing
      06:01
      I'll fill your asshole with cum to overflowing
      MrNastyXavier
      1.8M 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
    • 3 anal orgasm and hot creampie for skinny trans whore
      16:52
      3 anal orgasm and hot creampie for skinny trans whore
      ActorFab
      1.8M 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
    • When you Don't Want Anymore But Master Still Gives You
      02:20
      When you Don't Want Anymore But Master Still Gives You
      970.3K 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
    • TRANSEROTICA Sub TS Natalie Mars Bound by MILF Dee Williams
      12:05
      TRANSEROTICA Sub TS Natalie Mars Bound by MILF Dee Williams
      Trans Erotica
      441.5K views
    • Compilation with Weekly Episodes from the pain whore Alina
      02:05
      Compilation with Weekly Episodes from the pain whore Alina
      alinanightsky
      63.5K views
    • Long Anal Session for Hurting Emma Tied to the Bench
      01:05:06
      Long Anal Session for Hurting Emma Tied to the Bench
      ActorFab
      253.2K views
    • Caning and choking Kitsy
      04:56
      Caning and choking Kitsy
      Kitsy Meow
      74.8K views
    • Massaged To Climax
      15:03
      Massaged To Climax
      kinkts
      3.8M views
    • fucking my femboy slave sissy slut painful anal
      01:33
      fucking my femboy slave sissy slut painful anal
      130.5K views
    • Prostate orgasms
      11:10
      Prostate orgasms
      169.9K views
    • Pleasure Pain Sissy
      03:14
      Pleasure Pain Sissy
      48K views
    • PANSEXUALX Big Dick Erica Cherry Bangs Out 2 College Cuties
      15:08
      PANSEXUALX Big Dick Erica Cherry Bangs Out 2 College Cuties
      PansexualX
      6.4M views
    • 116 min degrading of bdsm sissy pain whore Alina
      02:20
      116 min degrading of bdsm sissy pain whore Alina
      alinanightsky
      79.4K views
    • TS Lena Kelly naked wrestling fight with Sinn Sage
      12:41
      TS Lena Kelly naked wrestling fight with Sinn Sage
      EvolvedFights
      351.9K views
    • Redhead Asian shemale all covered in pain gets fucked
      07:10
      Redhead Asian shemale all covered in pain gets fucked
      Extreme Ladyboys
      73.4K views
    • why do I suddenly love trannys?
      12:46
      why do I suddenly love trannys?
      1.2M 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
      57.4K views
    • Indian Best Threesome Sex! Fuck Both of us
      22:48
      Indian Best Threesome Sex! Fuck Both of us
      indianXworld
      22M 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
    Cartoon
    Interracial
    Japanese
    Vintage
    Young
    Big Tits
    Small Cock
    Thai
    Lingerie
    Gangbang
    Trans Woman
    Threesome
    Colombian
    Petite
    BDSM
    Public
    Couple
    Rough Sex
    MILF
    Anal Masturbation
    POV
    Dildo
    Cuckold
    Stockings
    Small Tits
    Babysitter
    Trans Man
    Indian
    Outdoor
    Handjob
    Chinese
    Fetish
    Group Sex
    Hentai
    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