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

    Shemale Pain Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Pain
    Anal Pain
    Extreme Pain
    Ladyboy Pain
    Sissy Pain
    Crossdresser Pain
    Bbc Pain
    Pain Slut
    Trans Pain
    Guy in Pain
    Bbc Anal Pain
    Sissy in Pain
    Big Cock Pain
    Beautiful Thai Ladyboy Anal Pain
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Black tgirl with giant tool fucking a white ass fat faggot
      11:38
      Black tgirl with giant tool fucking a white ass fat faggot
      Latina Tranny
      1.6M 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
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.3M 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
    • 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
    • Painting tranny
      07:53
      Painting tranny
      650.7K 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
      260.6K 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
    • Daddy Milks Trans Girl Prostate
      05:06
      Daddy Milks Trans Girl Prostate
      Gray Perrier
      319.7K 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
    • He Screams For Shemeat Compilation 2020 (TS TOPS)
      15:53
      He Screams For Shemeat Compilation 2020 (TS TOPS)
      2.9M 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
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3M 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
    • Lovely young girl is a shemale with big cock
      08:11
      Lovely young girl is a shemale with big cock
      10.5M views
    • Pain Is Her Pleasure
      14:58
      Pain Is Her Pleasure
      kinkts
      1M views
    • BRUTAL Tgirl TOP Gives Guy Extreme Painal
      02:24
      BRUTAL Tgirl TOP Gives Guy Extreme Painal
      993.5K 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
    • I Sodomize Morgane Marks Intensely and Deeply Part 2
      13:58
      I Sodomize Morgane Marks Intensely and Deeply Part 2
      Mamou5891
      81.8K views
    • Pain and pleasure, chastity and lust, Part 2
      01:15:02
      Pain and pleasure, chastity and lust, Part 2
      340.5K views
    • She Wrecks His Ass
      01:37
      She Wrecks His Ass
      1.1M 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
      160.8K 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
    • 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
    • I'll fill your asshole with cum to overflowing
      06:01
      I'll fill your asshole with cum to overflowing
      MrNastyXavier
      1.9M views
    • Pain and pleasure, chastity and lust,  Part 1
      51:35
      Pain and pleasure, chastity and lust, Part 1
      125.2K views
    • why do I suddenly love trannys?
      12:46
      why do I suddenly love trannys?
      1.2M 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
    • Brutal top making him loud
      01:32
      Brutal top making him loud
      474.6K 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
    • 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
    • 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
      69.5K 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
      962.3K views
    • DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      02:37
      DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      231.9K views
    • Exotic Tranny Got That ULTRA-COCK!
      08:10
      Exotic Tranny Got That ULTRA-COCK!
      Anna Loves Shemale
      1.2M views
    • fucking my femboy slave sissy slut painful anal
      01:33
      fucking my femboy slave sissy slut painful anal
      130.5K views
    • hard session of needle in ball by my master part 2 of 3
      02:14
      hard session of needle in ball by my master part 2 of 3
      279.5K views
    • Caning and choking Kitsy
      04:56
      Caning and choking Kitsy
      Kitsy Meow
      74.8K views
    • Latin Mature Tranny Predator with Monster Cock Fuck a Slave
      09:21
      Latin Mature Tranny Predator with Monster Cock Fuck a Slave
      8M 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
      31.1K views
    • Maso Whore Fucked and Slapped Like Good Slave
      16:30
      Maso Whore Fucked and Slapped Like Good Slave
      ActorFab
      100.6K views
    • Pleasure Pain Sissy
      03:14
      Pleasure Pain Sissy
      48K views
    • He can't run
      00:17
      He can't run
      1.1M 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
    • Dude takes a tranny painal
      01:16
      Dude takes a tranny painal
      169.2K views
    • Pathetic Maid Apology Riding Crop Self Punishment
      13:17
      Pathetic Maid Apology Riding Crop Self Punishment
      JessicaLynn15
      2.3K views
    • She fucks him so hard he can't take it, very dominant shemal
      04:08
      She fucks him so hard he can't take it, very dominant shemal
      304.7K views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80

    Searches Related to Shemale Pain

    • Shemale Painful Anal
    • Extreme Pain
    • Sissy Moaning Screaming
    • Amateur Painal Homemade
    • No Mercy Fuck
    • Shemales Brutal
    • Please Stop
    • He Can't Take It
    • Uncontrollable Intense Shaking Orgasm
    • Destroyed by BBC
    • Black Boy Screams
    • Raw Creampie
    • Humiliating Cock Comparison
    • Too Big
    • First Time Sex Very Hard
    • Aggressive Top
    • Out of Control
    • Rectal Prolapse
    • Beautiful Agony
    • Destroy Ass
    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