PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    WINTER MAGIC SALE ❄️☃️ Snowy discounts, hot deals!

    Painful Bdsm Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Bdsm
    Painful
    Sissy BDSM
    Shemale BDSM
    Painful Anal
    Trans BDSM
    Crossdresser BDSM
    Ladyboy BDSM
    Feminization BDSM
    Femboy BDSM
    Bdsm Milking
    Bdsm Sissy
    Latex BDSM
    Bdsm Fisting
    Japanese BDSM
    Painful Cum
    Ts BDSM
    Ladyboy Painful
    German BDSM
    Amateur BDSM
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Long Anal Session for Hurting Emma Tied to the Bench
      01:05:06
      Long Anal Session for Hurting Emma Tied to the Bench
      ActorFab
      270.1K views
    • Hung Ts Aakosha Bentley makes her sub scream in pain
      02:03
      Hung Ts Aakosha Bentley makes her sub scream in pain
      911.4K views
    • Mamou with Rachelle Karol I Dominate a Pretty Submissive Before Taking Her Part 2
      12:58
      Mamou with Rachelle Karol I Dominate a Pretty Submissive Before Taking Her Part 2
      Mamou5891
      71.4K 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
      99.9K 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
    • Teen Gets Her 1st Painful Screaming Anal But Let Her Finish
      10:28
      Teen Gets Her 1st Painful Screaming Anal But Let Her Finish
      100.2K views
    • Extreme Hard Spaking for the Maso Cunt
      08:02
      Extreme Hard Spaking for the Maso Cunt
      ActorFab
      199.4K 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
      274.9K views
    • anything
      09:14
      anything
      1.4M views
    • Pain Slut Kira
      36:28
      Pain Slut Kira
      Twistedrama
      100.2K 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
      452.6K views
    • Pain and pleasure, chastity and lust, Part 2
      01:15:02
      Pain and pleasure, chastity and lust, Part 2
      341.8K 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
      172.6K views
    • Pain and Pleasure  Part 2
      01:15:03
      Pain and Pleasure Part 2
      260.4K views
    • Hard Belting my sissy slave two
      01:36
      Hard Belting my sissy slave two
      115.6K 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
    • anal destruction and face slapping for maso whore
      10:41
      anal destruction and face slapping for maso whore
      ActorFab
      104.8K views
    • Pain and pleasure, chastity and lust,  Part 1
      51:35
      Pain and pleasure, chastity and lust, Part 1
      126.2K views
    • Degraded and bound Alina learns that her pleasure is on the secon place during exhausting bdsm session
      11:20
      Degraded and bound Alina learns that her pleasure is on the secon place during exhausting bdsm session
      alinanightsky
      307.2K views
    • Pleasure and pain 2
      26:26
      Pleasure and pain 2
      307.5K views
    • Daddy Milks Trans Girl Prostate
      05:06
      Daddy Milks Trans Girl Prostate
      Gray Perrier
      334.2K views
    • Relevant Short videos

      Slut cd using stiging nettles.
      Slut cd using stiging nettles.
      Amy-leigh8969
      2.5K 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
      538 views
      Ifetfuc chastity devices and ball stretching toys.  Humiliation as he is turned to a sissy for mistress.  Painful.
      Ifetfuc chastity devices and ball stretching toys. Humiliation as he is turned to a sissy for mistress. Painful.
      iFetFuc
      3.5K views
      Thrilling moment from "A sissy tortures her buttocks severely with nettles, ties up her balls, dildoes herself and makes herself cum with the vibrator"
      Thrilling moment from "A sissy tortures her buttocks severely with nettles, ties up her balls, dildoes herself and makes herself cum with the vibrator"
      MyLolaTrav
      381 views
      Sissy Whores Anal Seduction Comeback: Denise Humain as Pink Lingerie Cumslut – Begging for extreme gangbangs, deepthroat & gaping holes! | Clip 1
      Sissy Whores Anal Seduction Comeback: Denise Humain as Pink Lingerie Cumslut – Begging for extreme gangbangs, deepthroat & gaping holes! | Clip 1
      Denise Humain
      598 views
      Captivating moment from "some fun kitty playtime"
      Captivating moment from "some fun kitty playtime"
      Kittykisses96
      556 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
      214.8K 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
      234.8K 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
    • Open Up my Ass and Piss Inside
      02:23
      Open Up my Ass and Piss Inside
      Loren Aprile
      646.3K 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
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.4M views
    • DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      02:37
      DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      231.9K views
    • Natalie Mars
      18:56
      Natalie Mars
      917.3K views
    • fucking my femboy slave sissy slut painful anal
      01:33
      fucking my femboy slave sissy slut painful anal
      131.3K views
    • Domina Satana , Allegro and Boo Boo
      08:38
      Domina Satana , Allegro and Boo Boo
      Allegro
      10.7K 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
    • Nipple Torture and Masturbation
      06:57
      Nipple Torture and Masturbation
      AdriaTrans
      64.6K views
    • Pathetic Maid Apology Riding Crop Self Punishment
      13:17
      Pathetic Maid Apology Riding Crop Self Punishment
      JessicaLynn15
      2.3K views
    • Paddle Spanking and Dildo Deepthroat Formation for Teen TS Kitty Rose
      08:12
      Paddle Spanking and Dildo Deepthroat Formation for Teen TS Kitty Rose
      ActorFab
      115.1K 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
    • male tgirl and female
      10:47
      male tgirl and female
      96.2K views
    • Spiked Chastity Cage Torment - Sissy Maids Self Bondage
      18:39
      Spiked Chastity Cage Torment - Sissy Maids Self Bondage
      Derek6699
      101.1K views
    • Hard Slaps for Maso Bitch
      18:38
      Hard Slaps for Maso Bitch
      ActorFab
      147.8K views
    • Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots
      17:38
      Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots
      Derek6699
      74K views
    • Mistress Fucks My Urethra
      06:12
      Mistress Fucks My Urethra
      AdriaTrans
      61.3K 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
    • Sklavin V
      01:31
      Sklavin V
      168.3K views
    • More maintenance spanking for Kitsy. OTK punishment.
      06:53
      More maintenance spanking for Kitsy. OTK punishment.
      Kitsy Meow
      23.7K views
    • Maso Whore Fucked and Slapped Like Good Slave
      16:30
      Maso Whore Fucked and Slapped Like Good Slave
      ActorFab
      103K views
    • Sissy Denise: Tied Nipples Tortured with Rough Round Brushes
      18:54
      Sissy Denise: Tied Nipples Tortured with Rough Round Brushes
      Denise Humain
      2.1K views
    • Teen ladyboy in bondage Nannie gets an anal enema filled with her own pee
      06:20
      Teen ladyboy in bondage Nannie gets an anal enema filled with her own pee
      Ladyboy Gold
      601.7K 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 Painful Bdsm

    • Extreme BDSM Torture
    • Sissy Pain
    • Femdom Ballbusting
    • Forced Orgasm Bondage
    • Rough Hardcore Punishment
    • Beautiful Agony
    • Painful Cum
    • Ass Destroy Slave
    • Femboy Domination and Tortured
    • Electric Shock
    • Black Boy Screams
    • Submissive Humiliation
    • Punished in Chastity
    • Fuck the Shit Outta Me
    • Brutal Gangbang
    • Cruel Dominatrix Punishing Crossdresser
    • Extreme BDSM
    • What Is a Sissygasm
    • Monster Cock Leather
    • Anime Girl Tied up
    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