PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    LOVE FOR HALF THE PRICE ❤️😍 Happy Valentine's Day

    Prison Of Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Prison
    Sissy Crossdresser
    Sissy Training
    Sissy Feminization
    Sissy BBC
    Sissy Chastity
    Sissy Husband
    Sissy Compilation
    Sissy Fucked
    Amateur Sissy
    Sissy Blowjob
    Sissy Gangbang
    Sissy Cuckold
    Sissy Slave
    Sissy Boy
    Sissy Femdom
    Sissy Slut
    Sissy Faggot
    Sissy Cum
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • 3 anal orgasm and hot creampie for skinny trans whore
      16:52
      3 anal orgasm and hot creampie for skinny trans whore
      ActorFab
      2.2M views
    • Prison of Sissy 3 the Pr Manager Fucked
      11:10
      Prison of Sissy 3 the Pr Manager Fucked
      Johannesgaming
      25.6K 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
      328.2K 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
      25.1K views
    • Submission Sissy Trainer
      03:23
      Submission Sissy Trainer
      1.2M views
    • Prison of Sissy 4 I Love to Suck Cock
      14:54
      Prison of Sissy 4 I Love to Suck Cock
      Johannesgaming
      13.4K views
    • Rented Out by His Mistress
      06:12
      Rented Out by His Mistress
      Pure Ts
      101.6K views
    • Prison of Sissy - Crime Is Not the Way to Go.
      31:05
      Prison of Sissy - Crime Is Not the Way to Go.
      Johannesgaming
      19.6K views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.3M 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
      13.3K views
    • Sauna sissy slut got deepthroated and anal fucking like a good sex slave for BDSM
      39:24
      Sauna sissy slut got deepthroated and anal fucking like a good sex slave for BDSM
      alinanightsky
      191.1K views
    • Paying My First Debt in Jail - Prison Of Sissy
      08:09
      Paying My First Debt in Jail - Prison Of Sissy
      Asura
      28.5K views
    • Sissy Mind Alteration Video!
      04:45
      Sissy Mind Alteration Video!
      422.1K views
    • A Demand for The Cure - Prison of Sissy
      09:07
      A Demand for The Cure - Prison of Sissy
      Asura
      25.5K 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
      256.8K views
    • Prison of Sissy - Crime Is Not the Way to Go
      31:05
      Prison of Sissy - Crime Is Not the Way to Go
      Johannesgaming
      21.4K views
    • Sissyfication
      43:09
      Sissyfication
      1.1M views
    • How to Train Your Sissy Boyfriend
      08:12
      How to Train Your Sissy Boyfriend
      Brat Perversions
      141.4K 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
      573.8K views
    • feminisation training
      09:58
      feminisation training
      I IndirectInitiator50
      100.3K views
    • Sissy identity
      08:50
      Sissy identity
      604.3K 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
      98.1K views
    • Trust The Fucking Process
      52:41
      Trust The Fucking Process
      1M views
    • Sissy Slut Motel
      58:39
      Sissy Slut Motel
      751.4K views
    • CD TRAP SISSY EDUCATION TRAINING 101
      01:27:33
      CD TRAP SISSY EDUCATION TRAINING 101
      965.2K views
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.6M 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
      265.7K views
    • Daddy Milks Trans Girl Prostate
      05:06
      Daddy Milks Trans Girl Prostate
      Gray Perrier
      397.7K views
    • Sissy cums too early and gets punished with rough fucking
      02:35
      Sissy cums too early and gets punished with rough fucking
      2.2M views
    • Sissy Sex Slave
      07:00
      Sissy Sex Slave
      Kapri Sun
      90.5K views
    • BBC Fucks a Slutty Crossdresser Without Limits
      32:44
      BBC Fucks a Slutty Crossdresser Without Limits
      Trans and Co
      425K views
    • 2032 - the Bwno Future
      15:06
      2032 - the Bwno Future
      ChristineWest120
      137.9K views
    • Warning : Sissyfication is real - Sissy Joyce's warning
      03:57
      Warning : Sissyfication is real - Sissy Joyce's warning
      Sissy Joyce
      865.2K views
    • Sissy Joyce - A real life sissy slave
      01:16
      Sissy Joyce - A real life sissy slave
      Sissy Joyce
      715.2K views
    • family fun 1.mp4
      13:05
      family fun 1.mp4
      1.8M views
    • sugar Cravsitt Presents: BBC 3
      58:34
      sugar Cravsitt Presents: BBC 3
      2.4M views
    • CUM TWICE - The best compilaion - 3 SEASON - KinkyHome TV
      01:17:55
      CUM TWICE - The best compilaion - 3 SEASON - KinkyHome TV
      KinkyHome
      1.5M views
    • A guide to sissication: Beginner - Am I a sissy?
      23:32
      A guide to sissication: Beginner - Am I a sissy?
      786.6K views
    • Shemale Anatomy
      03:06
      Shemale Anatomy
      2.9M 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
      160.1K views
    • anal destruction and face slapping for maso whore
      10:41
      anal destruction and face slapping for maso whore
      ActorFab
      136.3K views
    • I'll fill your asshole with cum to overflowing
      06:01
      I'll fill your asshole with cum to overflowing
      MrNastyXavier
      2.1M views
    • Bound sissy in chastity gets BBC
      07:46
      Bound sissy in chastity gets BBC
      975.3K views
    • Never Expecting to Be a Sexy Girl
      08:12
      Never Expecting to Be a Sexy Girl
      Pure Ts
      519.4K views
    • Turned Into A Cock Loving Sissy
      18:35
      Turned Into A Cock Loving Sissy
      835.7K views
    • Submit to Daddy sissy trainer
      05:26
      Submit to Daddy sissy trainer
      444.1K views
    • Sissy Swap Tales Schoolgirl Sissies 1
      10:24
      Sissy Swap Tales Schoolgirl Sissies 1
      1.1M 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 Prison Of Sissy

    Sissy Transformation Male to Female
    Femboy Sissification
    Feminized and Fucked
    Intense Prison Style
    Crossdressing Caught Dressed
    Crossdresser Fantasy
    Femdom Feminization
    Degraded Sissies
    Turning Cuck Husband Into Faggot
    Gay Sissyboy
    Sissycdmish
    Sissy-Boys
    Crossdressing Sex Stories
    Young Crossdressers
    Secret Sissyboy
    Crossdresser Boy
    Dressing as a Girl
    Ladyboy Gloryhole
    Permanent Chastity
    Femboy Used
    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