PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    BLUE MONDAY SALE 💛🎉 Brighten the year’s saddest day

    Hardcore Pain Anal 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
    • 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
      218.3K 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
      402.7K 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
      108.1K views
    • some fun kitty playtime
      16:17
      some fun kitty playtime
      Kittykisses96
      20.9K views
    • Extreme Painanal large dildo with chilli sauce pushes Denise to her limits and makes her cry.
      14:26
      Extreme Painanal large dildo with chilli sauce pushes Denise to her limits and makes her cry.
      Denise Humain
      43.1K views
    • Sissy Whores Anal Seduction Comeback: Denise Humain as Pink Lingerie Cumslut – Begging for extreme gangbangs, deepthroat & gaping holes!
      05:13
      Sissy Whores Anal Seduction Comeback: Denise Humain as Pink Lingerie Cumslut – Begging for extreme gangbangs, deepthroat & gaping holes!
      Denise Humain
      2.9K views
    • Extreme Anal Insertion Two Foot Long XXL Anal Slink
      10:11
      Extreme Anal Insertion Two Foot Long XXL Anal Slink
      TheToxicTwins
      45.1K views
    • Another weekend - Same result, nipples hurt, asshole is destroyed, still i wish i dont had to do it by myself.
      14:21
      Another weekend - Same result, nipples hurt, asshole is destroyed, still i wish i dont had to do it by myself.
      Denise Humain
      13.7K 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
    • Desi painful anal sex poojakichut
      05:55
      Desi painful anal sex poojakichut
      RoZestyBypass99
      13.6K views
    • Domination and pain with this 2 shemales hardcore punishment
      10:07
      Domination and pain with this 2 shemales hardcore punishment
      Latina Tranny
      31.4K views
    • BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
      07:34
      BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
      Denise Humain
      5.6K views
    • BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys
      08:00
      BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys
      Denise Humain
      6.3K views
    • No pain no sissy gain
      01:32
      No pain no sissy gain
      Kittykisses96
      5K views
    • Denise Humain in bath Final hard self spanking and nipple pain
      23:11
      Denise Humain in bath Final hard self spanking and nipple pain
      Denise Humain
      8.4K views
    • Denise Humain works on her Asshole for 45 Minutes straight and to the limit.
      44:19
      Denise Humain works on her Asshole for 45 Minutes straight and to the limit.
      Denise Humain
      9.2K views
    • Preview Video for Maledoms wanna see my Sissy Skills. Sexy Deepthroat Blowjob and extreme Ass gaping pussy.
      02:47
      Preview Video for Maledoms wanna see my Sissy Skills. Sexy Deepthroat Blowjob and extreme Ass gaping pussy.
      Denise Humain
      5.2K views
    • Denise Humain Scene Mix (Anal, Nipple, Blowjob)
      17:28
      Denise Humain Scene Mix (Anal, Nipple, Blowjob)
      Denise Humain
      4.3K 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
    • Sissy Denise: Nipple torture with combination pliers – Live until the end
      09:37
      Sissy Denise: Nipple torture with combination pliers – Live until the end
      Denise Humain
      2.6K views
    • Let her feel what Nipple Pain means. Let her suffer to her limit while we smile at her.
      13:59
      Let her feel what Nipple Pain means. Let her suffer to her limit while we smile at her.
      Denise Humain
      20K views
    • Relevant Short videos

      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
      A naughty housemaid with ripped black pantyhose tried the thickest dildo into her sissy pussy and moaned with pain and joy | Clip 1
      A naughty housemaid with ripped black pantyhose tried the thickest dildo into her sissy pussy and moaned with pain and joy | Clip 1
      Harinni
      176 views
      A naughty housemaid with ripped black pantyhose tried the thickest dildo into her sissy pussy and moaned with pain and joy | Clip 2
      A naughty housemaid with ripped black pantyhose tried the thickest dildo into her sissy pussy and moaned with pain and joy | Clip 2
      Harinni
      201 views
      Epic moment from "BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys"
      Epic moment from "BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys"
      Denise Humain
      474 views
      Emotional moment from "BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys"
      Emotional moment from "BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys"
      Denise Humain
      592 views
    • A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
      28:23
      A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
      Denise Humain
      12.2K views
    • FtM stuffed and whipped painfully
      07:06
      FtM stuffed and whipped painfully
      1K views
    • FtM boy punished for being lazy
      05:10
      FtM boy punished for being lazy
      4.7K views
    • FTM fucking a huge dildo and pin orgasm
      02:34
      FTM fucking a huge dildo and pin orgasm
      Ares FTM
      2.6K views
    • Sissy tortured with wax
      02:59
      Sissy tortured with wax
      Sissy_Nadiene
      1.2K 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
      968.3K views
    • Painting tranny
      07:53
      Painting tranny
      654.3K 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
    • 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
    • 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
    • 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
    • Pain Slut Kira
      36:28
      Pain Slut Kira
      Twistedrama
      100.2K 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
    • Pain and Pleasure  Part 2
      01:15:03
      Pain and Pleasure Part 2
      260.4K 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
      66.4K views
    • Pain and pleasure, chastity and lust,  Part 1
      51:35
      Pain and pleasure, chastity and lust, Part 1
      126.2K 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
    • Compilation with Weekly Episodes from the pain whore Alina
      02:05
      Compilation with Weekly Episodes from the pain whore Alina
      alinanightsky
      64.5K views
    • DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      02:37
      DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
      231.9K views
    • fucking my femboy slave sissy slut painful anal
      01:33
      fucking my femboy slave sissy slut painful anal
      131.3K views
    • 116 min degrading of bdsm sissy pain whore Alina
      02:20
      116 min degrading of bdsm sissy pain whore Alina
      alinanightsky
      80.1K views
    • Spiked Chastity Cage Torment - Sissy Maids Self Bondage
      18:39
      Spiked Chastity Cage Torment - Sissy Maids Self Bondage
      Derek6699
      101.1K 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
    • 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
    • 25 min of abuse and hard use for the pain whore Alina
      03:04
      25 min of abuse and hard use for the pain whore Alina
      alinanightsky
      53.2K views
    • The sissy pain whore Alina show her skills in self-humiliation and deep throating with dildo
      02:55
      The sissy pain whore Alina show her skills in self-humiliation and deep throating with dildo
      alinanightsky
      28.4K 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
    Sissy
    Shemale Fucks Girl
    Ladyboy
    Guy Fucks Shemale
    Compilation
    Blowjob
    Cum In Mouth
    Big Black Cock
    Big Ass
    Bareback
    Creampie
    Cumshot
    Mature
    Homemade
    Teen
    Masturbation
    Domination
    Anal
    Brazilian
    Solo
    Asian
    Transgender
    BBW
    Mexican
    Cartoon
    Interracial
    Vintage
    Japanese
    Big Tits
    Young
    Small Cock
    Thai
    Gangbang
    Trans Woman
    Lingerie
    Threesome
    Colombian
    Petite
    BDSM
    Public
    Rough Sex
    Couple
    MILF
    Anal Masturbation
    POV
    Dildo
    Cuckold
    Stockings
    Small Tits
    Babysitter
    Trans Man
    Indian
    Handjob
    Outdoor
    FTM
    Hentai
    Chinese
    Fetish
    Group Sex
    Massage
    Bondage
    Pissing
    British
    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