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

    18 Anal 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
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3M 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
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.3M views
    • Trans Girl plays with an 18 cm Dildo for the first time, Moans from pain but ends up liking it  Succubo16
      29:58
      Trans Girl plays with an 18 cm Dildo for the first time, Moans from pain but ends up liking it Succubo16
      LaRicura16
      10.9K 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
    • Sweet Anal Pain for Solo Sissy CD
      05:00
      Sweet Anal Pain for Solo Sissy CD
      Regina Blasegern
      11.4K 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
    • cd tranny getting anal pain pounding by fucking machine
      00:57
      cd tranny getting anal pain pounding by fucking machine
      Sasha Earth
      11.7K 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
    • Hot CD loves the anal pain she's giving herself by destroying her ass with large dildo(WARNING HOT VIDEO!!)
      06:57
      Hot CD loves the anal pain she's giving herself by destroying her ass with large dildo(WARNING HOT VIDEO!!)
      Dope Slut
      3.1K 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
    • 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
    • Compilation: Trannies Cum While they get Fucked
      13:29
      Compilation: Trannies Cum While they get Fucked
      3.8M 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
    • Lovely young girl is a shemale with big cock
      08:11
      Lovely young girl is a shemale with big cock
      10.5M views
    • Painting tranny
      07:53
      Painting tranny
      650.7K views
    • Indian Best Threesome Sex! Fuck Both of us
      22:48
      Indian Best Threesome Sex! Fuck Both of us
      indianXworld
      22M 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
    • Shemale Anatomy
      03:06
      Shemale Anatomy
      2.8M 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
    • 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
    • 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
      401.7K views
    • Illuxxxtrandy Hot Blonde with Big Ass Fucked Doggy Style by Huge Monster Cock in Public Bathroom - Intense, Dirty Sex with Tight
      02:15
      Illuxxxtrandy Hot Blonde with Big Ass Fucked Doggy Style by Huge Monster Cock in Public Bathroom - Intense, Dirty Sex with Tight
      sinsweethoneyasses
      2.1M 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
    • Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
      08:12
      Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
      nbnabunny
      1.6M views
    • Pain Slut Kira
      36:28
      Pain Slut Kira
      Twistedrama
      100.2K 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
    • 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
    • handz free shemale cumming while getting fucked
      13:40
      handz free shemale cumming while getting fucked
      2.4M 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
    • Moaning heaps while He came so deep inside me nothing comes
      02:56
      Moaning heaps while He came so deep inside me nothing comes
      Littlemapleberry
      1.6M views
    • Pain and Pleasure  Part 2
      01:15:03
      Pain and Pleasure Part 2
      260.4K views
    • Sissy Cums Too Early And Gets Punished With Rough Fucking.
      03:20
      Sissy Cums Too Early And Gets Punished With Rough Fucking.
      962.7K 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
    • 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
    • Pain and pleasure, chastity and lust,  Part 1
      51:35
      Pain and pleasure, chastity and lust, Part 1
      125.2K 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
    • 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
    • I have sex with my ex-boyfriend's transsexual crush
      09:25
      I have sex with my ex-boyfriend's transsexual crush
      NaughtyTrans
      4.2M 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
    • travesti amateur
      04:25
      travesti amateur
      1.7M views
    • DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      02:37
      DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      231.9K views
    • why do I suddenly love trannys?
      12:46
      why do I suddenly love trannys?
      1.2M views
    • fucking my femboy slave sissy slut painful anal
      01:33
      fucking my femboy slave sissy slut painful anal
      131.3K views
    • Exotic Tranny Got That ULTRA-COCK!
      08:10
      Exotic Tranny Got That ULTRA-COCK!
      Anna Loves Shemale
      1.2M 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
    • You Are Just a Hole - Variety Itsol
      10:46
      You Are Just a Hole - Variety Itsol
      Rodrigo Amor
      1.8M 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 18 Anal Pain

    • Cd Anal Fuck
    • Ass Fucked Hard
    • 11 Yaas Xxxw XXX Sexy
    • Trans Painal
    • Big Cock 18 Inch
    • Real Family Fucking
    • Dirty Asshole
    • Step Sister Fucks Virgin Step Brother
    • Lil Illy
    • Hardcore Teen
    • Assfucked and Cumshot
    • Ladyboy Pain
    • Bad but Good
    • Sad Sex
    • 18Teen HD
    • Dark Buttholes
    • 10 Cumshots
    • Oh No No No No
    • Young Dildo
    • 12
    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