PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    LET IT SNOW, LET IT SAVE! ☃️ Faphouse Discounts – Winter Edition

    Classic Prison 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
      3.1M views
    • julie bond fucks girl in prison
      11:19
      julie bond fucks girl in prison
      115.4K views
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.4M views
    • PRISON BITCH
      00:46
      PRISON BITCH
      21.6K 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
      21.6M views
    • Captive life, peeing in prison
      06:20
      Captive life, peeing in prison
      alina1235698
      30.9K views
    • Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time - Trans Angels
      10:25
      Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time - Trans Angels
      Trans Angels
      9.2M views
    • Vintage shemale fun in a prison
      37:19
      Vintage shemale fun in a prison
      70.7K views
    • This happened to me leaving school
      19:20
      This happened to me leaving school
      ELIZABETH LARA
      4.3M views
    • Silky Satin Pleasure Prisoner
      00:20
      Silky Satin Pleasure Prisoner
      Shinys Bound SluTS
      3.1K views
    • Lovely young girl is a shemale with big cock
      08:11
      Lovely young girl is a shemale with big cock
      10.7M views
    • Tomboy Lesbians Futa Sexfight - Wrestling Prison Tattoo Girls Having Horny Fun with CUM Play
      09:15
      Tomboy Lesbians Futa Sexfight - Wrestling Prison Tattoo Girls Having Horny Fun with CUM Play
      Futanari XXX
      459.2K views
    • He Screams For Shemeat Compilation 2020 (TS TOPS)
      15:53
      He Screams For Shemeat Compilation 2020 (TS TOPS)
      2.9M views
    • TRANS ANGELS - Officer Chanel Santini Cannot Resist Getting  Fucked With Hot Prisoner Kimberlee
      35:45
      TRANS ANGELS - Officer Chanel Santini Cannot Resist Getting Fucked With Hot Prisoner Kimberlee
      Trans Angels
      1.3M 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
      2.2M views
    • Prison Futa Transformation - 18 Years Old Matty Mila Summons Demon and Turns Into Insatiable Shemale
      07:06
      Prison Futa Transformation - 18 Years Old Matty Mila Summons Demon and Turns Into Insatiable Shemale
      Futanari XXX
      288.3K views
    • I'll fill your asshole with cum to overflowing
      06:01
      I'll fill your asshole with cum to overflowing
      MrNastyXavier
      2M views
    • Prison Guard Fucks Blonde Inmate After FUTA Transformation Ends With Huge Facial TRAILER
      01:18
      Prison Guard Fucks Blonde Inmate After FUTA Transformation Ends With Huge Facial TRAILER
      Futanari XXX
      1.8M views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.2M views
    • Prison Guard Ts fucks another prisoner tranny 02
      07:00
      Prison Guard Ts fucks another prisoner tranny 02
      895.5K 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
    • TSVirtualLovers - Sex with the Prisoner in POV
      09:24
      TSVirtualLovers - Sex with the Prisoner in POV
      TS Virtual Lovers
      172.3K views
    • Prison of Sissy 3 the Pr Manager Fucked
      11:10
      Prison of Sissy 3 the Pr Manager Fucked
      Johannesgaming
      20.4K views
    • rosario prison style
      01:07
      rosario prison style
      238.4K 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
      7.6M views
    • Hot anal trans sex prison house fantasies
      24:32
      Hot anal trans sex prison house fantasies
      Shemale Strokers
      351.7K 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
      555.2K views
    • intense prison style
      00:28
      intense prison style
      1M 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
      6.1M views
    • My First Day in Prison: Bathroom Experience
      07:30
      My First Day in Prison: Bathroom Experience
      Asura
      116.9K views
    • Sissy cum dump compilation
      28:49
      Sissy cum dump compilation
      2.6M views
    • Nathalia Fontes Is Dominated and Punished in Abandoned Prison
      13:00
      Nathalia Fontes Is Dominated and Punished in Abandoned Prison
      Onlyfans
      101.5K views
    • Picking up a Sexy Tgirl off the Streets and Giving Her My BBC
      08:12
      Picking up a Sexy Tgirl off the Streets and Giving Her My BBC
      TGIRLPLAYHOUSE
      2.3M 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
    • sissies in prison
      01:37:44
      sissies in prison
      723K views
    • Chicks with Dicks - Sexy Latina Turns Into Prison Cum Slut for Redhead Sata Jones Futa Creampie
      01:35
      Chicks with Dicks - Sexy Latina Turns Into Prison Cum Slut for Redhead Sata Jones Futa Creampie
      Futanari XXX
      186.3K views
    • Girl forgot to tell her Tinder date that she’s Trans
      07:22
      Girl forgot to tell her Tinder date that she’s Trans
      JsseMontz
      648.5K views
    • Female alien in a prison gets fucked hard by a hot dickgirl
      27:56
      Female alien in a prison gets fucked hard by a hot dickgirl
      martha 3d group
      42.7K views
    • PANSEXUALX Big Dick Erica Cherry Bangs Out 2 College Cuties
      15:08
      PANSEXUALX Big Dick Erica Cherry Bangs Out 2 College Cuties
      PansexualX
      6.6M views
    • Travtchoin fertilize 5 times by a former prisoner from Lyon
      03:04
      Travtchoin fertilize 5 times by a former prisoner from Lyon
      186K views
    • My stepmom is a tranny
      16:46
      My stepmom is a tranny
      Combat zone transsexual barebacking
      1.1M 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
      11.8K views
    • Older bangs tranny in prison (2019)
      04:57
      Older bangs tranny in prison (2019)
      1.3M views
    • Agatha Vega Tg Prison Fuck - Horny Shemale Detective Gets Blowjob from Latina Girl
      07:06
      Agatha Vega Tg Prison Fuck - Horny Shemale Detective Gets Blowjob from Latina Girl
      Futanari XXX
      78.2K views
    • I Fuck a Beautiful 19-year-old Trans Girl with a Big Dick
      08:12
      I Fuck a Beautiful 19-year-old Trans Girl with a Big Dick
      barbanegrazponto1onepov
      2.1M 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
    • Hostel Surprise
      37:09
      Hostel Surprise
      3.1M 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 Classic Prison

    • New Algerian Sex 2025 Algerian
    • Éjac Accidentelle
    • Maximum Perversum Extrem Pervers
    • 9Hab Anal Maroc Casablanca
    • Trans avec une Enorme Bite
    • Sissy Se Fait Baiser Brutalement
    • Les Plus Belles Salopes Travestis
    • Big Dick Shemale Surprises Stranger
    • Film Français Complet Histoire Vraie
    • Branlette avec une Trans Française
    • Sperme Ejaculations Travestie
    • Travesti Baisé Brutalement
    • Bordel
    • Transsexuelle Mini Jupe
    • 3X Movies
    • Transsexuelle Ejaculation Accidentelle
    • Trans Francaise dans les Bois
    • Éjaculation Précoce
    • Lesbienne Transexuelle Francaise
    • La Maitresse D École Francais
    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