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

    Too Painful Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Painful
    Too Big
    Painful Cum
    Painful Anal
    Painful BBC
    Painful Creampie
    Ladyboy Painful
    Too Deep
    Too Tight
    Most Painful
    Too Much
    Shemale Too Big
    Cock Too Big
    Bbc Too Big
    Shemale Painful Anal
    Sissy Painful Anal
    Crossdresser Painful Anal
    Homemade Anal Painful
    First Anal Painful
    Cum Too Fast
    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
      3.4M 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
    • Dude takes a tranny painal
      01:16
      Dude takes a tranny painal
      170.8K views
    • Painting tranny
      07:53
      Painting tranny
      658.4K 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
    • Hunter boyfriend gave the pain of in the bathroom
      21:53
      Hunter boyfriend gave the pain of in the bathroom
      Redroseromance
      2.2M views
    • He Screams For Shemeat Compilation 2020 (TS TOPS)
      15:53
      He Screams For Shemeat Compilation 2020 (TS TOPS)
      2.9M 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
    • Don't do this to me! I do not like it!
      03:01
      Don't do this to me! I do not like it!
      742.3K 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
    • Bitch boy can't take her monster cock but she doesn't stop
      01:51
      Bitch boy can't take her monster cock but she doesn't stop
      956.7K 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
      101.7K 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
      984.7K 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
    • 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
    • Pain Is Her Pleasure
      14:58
      Pain Is Her Pleasure
      kinkts
      1M views
    • Can't handle it
      10:03
      Can't handle it
      140.7K 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
    • I'll fill your asshole with cum to overflowing
      06:01
      I'll fill your asshole with cum to overflowing
      MrNastyXavier
      2M views
    • Pain and pleasure, chastity and lust, Part 2
      01:15:02
      Pain and pleasure, chastity and lust, Part 2
      343.3K views
    • handz free shemale cumming while getting fucked
      13:40
      handz free shemale cumming while getting fucked
      2.4M views
    • Relevant Short videos

      Linda asian ts pain with champagne and big dildo. (sample)
      Linda asian ts pain with champagne and big dildo. (sample)
      Lindaasian-ts
      7.8K views
      Key moment from "Hunter boyfriend gave the pain of in the bathroom"
      Key moment from "Hunter boyfriend gave the pain of in the bathroom"
      Redroseromance
      11.1K views
      Pressing a giant plug out of my anus
      Pressing a giant plug out of my anus
      Charlotte Wilde
      4.5K views
      FUCKING MY HOLE WITH A  BOTTLE
      FUCKING MY HOLE WITH A BOTTLE
      youngtightcutie
      2.2K views
      Slut cd using stiging nettles.
      Slut cd using stiging nettles.
      Amy-leigh8969
      2.6K views
      Emotional moment from "How to Give Pain and Pleasure to a Big Sissy Cock"
      Emotional moment from "How to Give Pain and Pleasure to a Big Sissy Cock"
      MyLolaTrav
      697 views
    • Pain Slut Kira
      36:28
      Pain Slut Kira
      FapHouse
      101.7K views
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3.1M views
    • Pain and Pleasure  Part 2
      01:15:03
      Pain and Pleasure Part 2
      261.7K views
    • Daddy Milks Trans Girl Prostate
      05:06
      Daddy Milks Trans Girl Prostate
      Gray Perrier
      348.8K 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
    • Sissy Cums Too Early And Gets Punished With Rough Fucking.
      03:20
      Sissy Cums Too Early And Gets Punished With Rough Fucking.
      977.2K views
    • Pain and pleasure, chastity and lust,  Part 1
      51:35
      Pain and pleasure, chastity and lust, Part 1
      127.2K views
    • Hard Fucking My Marked Ass after a BDSM event
      17:17
      Hard Fucking My Marked Ass after a BDSM event
      Melodyfluffington
      154.1K 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
    • BRUTAL Tgirl TOP Gives Guy Extreme Painal
      02:24
      BRUTAL Tgirl TOP Gives Guy Extreme Painal
      1M 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
      216K views
    • Long Anal Session for Hurting Emma Tied to the Bench
      01:05:06
      Long Anal Session for Hurting Emma Tied to the Bench
      FapHouse
      278.1K 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
    • 3 anal orgasm and hot creampie for skinny trans whore
      16:52
      3 anal orgasm and hot creampie for skinny trans whore
      ActorFab
      2M views
    • Pleasure and pain 2
      26:26
      Pleasure and pain 2
      309K views
    • Extreme Hard Spaking for the Maso Cunt
      08:02
      Extreme Hard Spaking for the Maso Cunt
      FapHouse
      203.5K views
    • DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      02:37
      DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      233.4K views
    • Big ts dick made his little clit cum
      01:14
      Big ts dick made his little clit cum
      1.9M views
    • fucking my femboy slave sissy slut painful anal
      01:33
      fucking my femboy slave sissy slut painful anal
      132.1K views
    • You Are Just a Hole - Variety Itsol
      10:46
      You Are Just a Hole - Variety Itsol
      Rodrigo Amor
      1.9M 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
    • Maso Whore Fucked and Slapped Like Good Slave
      16:30
      Maso Whore Fucked and Slapped Like Good Slave
      FapHouse
      105.2K views
    • Pleasure Pain Sissy
      03:14
      Pleasure Pain Sissy
      48.4K views
    • Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie
      03:38
      Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie
      Melodyfluffington
      35.6K views
    • Spiked Chastity Cage Torment - Sissy Maids Self Bondage
      18:39
      Spiked Chastity Cage Torment - Sissy Maids Self Bondage
      Derek6699
      102.2K views
    • lie down bitch
      01:08
      lie down bitch
      775.3K views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 10
    9. ...
    10. 19
    19

    Searches Related to Too Painful

    • Hot Sissy
    • Extreme Pain
    • Pure Filth
    • Make Me a Sissy
    • Thai Massage Happy Ending
    • Fucking My Step Sister
    • Wife Makes Sissy Husband Suck BBC
    • Fucking 85 Year Old Granny
    • Incredible
    • First Anal Painful
    • Sissy First BBC
    • No Going Back
    • Screaming Anal
    • Real First Time
    • Tiny White Sissy Boys Love BBC
    • Shemale Screaming
    • Grandpa and Sissy Boy
    • Sissy BBC
    • Bbc Sissy Training
    • First Time Painful Anal
    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