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

    Prison Sissy Slut Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Slut
    Prison
    Sissy Slut
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Sissy Slave
    Amateur Sissy
    Sissy Blowjob
    Sissy Cuckold
    Sissy Gangbang
    Submissive Sissy
    Sissy Femdom
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • I'll fill your asshole with cum to overflowing
      06:01
      I'll fill your asshole with cum to overflowing
      MrNastyXavier
      1.9M views
    • Policewoman with a huge cock turns her prisoner into a dick slut
      08:28
      Policewoman with a huge cock turns her prisoner into a dick slut
      DotadaSP
      221.8K views
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.4M views
    • Extreme Anal Cavity Search - Dungeon Under Heathrow Airport - Mule Gets Found Out by valentinarosa89
      00:31
      Extreme Anal Cavity Search - Dungeon Under Heathrow Airport - Mule Gets Found Out by valentinarosa89
      Jasmine_dlight
      5.3K views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.1M views
    • prison sissy vs. men
      13:16
      prison sissy vs. men
      278.8K views
    • Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
      29:33
      Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
      Ria_Bentley
      2.5M views
    • sissies in prison
      01:37:44
      sissies in prison
      716.9K views
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3M views
    • Prison of Sissy 3 the Pr Manager Fucked
      11:10
      Prison of Sissy 3 the Pr Manager Fucked
      Johannesgaming
      20.4K views
    • 3 anal orgasm and hot creampie for skinny trans whore
      16:52
      3 anal orgasm and hot creampie for skinny trans whore
      ActorFab
      1.9M views
    • Prison of Sissy 2 Adam Used the Glory Hole Not to Get a BJ but to Give
      25:08
      Prison of Sissy 2 Adam Used the Glory Hole Not to Get a BJ but to Give
      Johannesgaming
      22.4K views
    • Lovely young girl is a shemale with big cock
      08:11
      Lovely young girl is a shemale with big cock
      10.5M views
    • Prison of Sissy - Crime Is Not the Way to Go.
      31:05
      Prison of Sissy - Crime Is Not the Way to Go.
      Johannesgaming
      16.9K views
    • Daddy's Good Girl!
      08:12
      Daddy's Good Girl!
      Pure Ts
      932.5K views
    • Straight boy disguises himself as hot femboy in prison. Prison of Sissy.
      09:39
      Straight boy disguises himself as hot femboy in prison. Prison of Sissy.
      Bigcockamateur
      10.9K views
    • Dads Bestmate Bangs Femboy
      05:11
      Dads Bestmate Bangs Femboy
      mothplayboy
      788.3K views
    • Paying My First Debt in Jail - Prison Of Sissy
      08:09
      Paying My First Debt in Jail - Prison Of Sissy
      Asura
      26.4K views
    • Sissy cum dump compilation
      28:49
      Sissy cum dump compilation
      2.6M views
    • A Demand for The Cure - Prison of Sissy
      09:07
      A Demand for The Cure - Prison of Sissy
      Asura
      23K 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
    • You Are a Prisoner to Your Sissy Porn
      11:48
      You Are a Prisoner to Your Sissy Porn
      Natalie Napoli
      13.7K views
    • 2032 - the Bwno Future
      15:06
      2032 - the Bwno Future
      ChristineWest120
      112.7K views
    • Prison of Sissy - Crime Is Not the Way to Go
      31:05
      Prison of Sissy - Crime Is Not the Way to Go
      Johannesgaming
      19.5K views
    • A Prostitute Offering Herself on the Street
      02:29
      A Prostitute Offering Herself on the Street
      Wesley Fudedor
      332.8K views
    • Nancy In Prison
      18:15
      Nancy In Prison
      Nancy Rose
      11.4K views
    • Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
      01:17
      Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
      Allmylinks
      106.4K views
    • PRISON BITCH
      00:46
      PRISON BITCH
      21.4K views
    • Shemale Anatomy
      03:06
      Shemale Anatomy
      2.8M views
    • Dickgirl Ladyboy Is Fucking Girl Standing in Her Prison Cell
      07:35
      Dickgirl Ladyboy Is Fucking Girl Standing in Her Prison Cell
      Wraith931
      10.4K views
    • Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
      18:27
      Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
      Vane03_siss
      217.2K views
    • Prison of Sissy: The First Friend
      06:43
      Prison of Sissy: The First Friend
      Asura
      33.6K views
    • This happened to me leaving school
      19:20
      This happened to me leaving school
      ELIZABETH LARA
      4.2M views
    • Captive life, peeing in prison
      06:20
      Captive life, peeing in prison
      alina1235698
      30.9K views
    • TRANS YEEHAW: Sloppy BJ & Ride By Canadian Cowgirl ABRIDGED
      09:05
      TRANS YEEHAW: Sloppy BJ & Ride By Canadian Cowgirl ABRIDGED
      Adam Castle
      371.8K views
    • Girl Sucks Sissy Ladyboy Dick in Prison
      08:43
      Girl Sucks Sissy Ladyboy Dick in Prison
      Wraith931
      7.7K views
    • Sissy Joyce - A real life sissy slave
      01:16
      Sissy Joyce - A real life sissy slave
      Sissy Joyce
      690.3K views
    • Exposing My Femboy Bubble Butt to Chef Michael in Prison Kitchen : Prison of Sissy Gameplay
      05:23
      Exposing My Femboy Bubble Butt to Chef Michael in Prison Kitchen : Prison of Sissy Gameplay
      Asura
      3.5K views
    • family fun 1.mp4
      13:05
      family fun 1.mp4
      1.8M views
    • Shemale Fucks Girl Standing in Bondage Prison Sex
      09:21
      Shemale Fucks Girl Standing in Bondage Prison Sex
      Wraith931
      6K views
    • This is how you treat a sissy slut! Guy uses tranny brutally in public and cums on her face!
      01:16
      This is how you treat a sissy slut! Guy uses tranny brutally in public and cums on her face!
      TV_Helena
      546.3K views
    • The Prison of Sissy - The Game Strarts
      09:04
      The Prison of Sissy - The Game Strarts
      Asura
      9.7K views
    • I turned my straight roommate intro trans wife
      05:20
      I turned my straight roommate intro trans wife
      CutePinkUnicorn
      505.2K views
    • Sissy Ladyboy Standing Anal in Prison
      08:49
      Sissy Ladyboy Standing Anal in Prison
      Wraith931
      just added
    • 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
      233.7K views
    • Shemale Standing Fuck Ladyboy Prison Sex
      08:05
      Shemale Standing Fuck Ladyboy Prison Sex
      Wraith931
      13.6K 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
      21.4M 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 Prison Sissy Slut

    • Sissy Femboy Fucked
    • Traps Femboys and Sissys
    • Femdom Bisex Slave Crossdresser
    • Secret Sissyboy
    • Fuck Me Like a Slut
    • Trans Public XXX
    • Extreme Rough Sex Brutal Hardcore
    • White Sissies 4 Black Masters
    • Submissive Transvestite Training
    • Crossdressing Story
    • Sissyslut
    • Teen Destroyed
    • Crossdressers First BBC
    • Sissy Pounded
    • Shemale Brainwashing
    • Turning Cuck Husband Into Faggot
    • Transgender Bimbo Porn
    • Femboi Trap
    • Sissypop by Futah
    • Real Prison Thug Breeding
    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