PornPorn Gay • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
      -60%
    • Pornstars
    • Channels
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday Sale

    Chastity Training Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Chastity
    Training
    Gay Chastity
    Gay Training
    Femboy Chastity
    Twink Chastity
    Poper Training
    Chastity Cage
    Chastity Bondage
    P Training
    Chastity Humiliation
    Chastity Cum
    Permanent Chastity
    Bbc Training
    Dildo Training
    Muscle Chastity
    Chastity Belt
    Bator Training
    Cocksucker Training
    Bottom Training
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Young boy locked in chastity dick cage and handcuffed naked
      01:19
      Young boy locked in chastity dick cage and handcuffed naked
      113.1K views
    • Sissy Denver in chastity, training her butt pussy
      05:42
      Sissy Denver in chastity, training her butt pussy
      Denverita
      13.6K views
    • Agf: I Keep Him Locked in Chastity and Let My Craving Passion Hotter
      05:46
      Agf: I Keep Him Locked in Chastity and Let My Craving Passion Hotter
      Amateur Guys Fuck
      46.6K views
    • Chastity Training - Hardcore Humiliation SPH
      04:21
      Chastity Training - Hardcore Humiliation SPH
      S1monReilly
      15.4K views
    • Cuckold life
      09:44
      Cuckold life
      113.5K views
    • Chastity training
      01:55
      Chastity training
      CEO sissy slave
      1.2K views
    • Caged sissy pushes out a load after a quick pump and dump (watch longer vids on OF: h.harryryan)
      03:39
      Caged sissy pushes out a load after a quick pump and dump (watch longer vids on OF: h.harryryan)
      HornyHarryRyan
      126.1K views
    • Chastity training
      00:08
      Chastity training
      980 views
    • Thank You Sir
      27:44
      Thank You Sir
      Muscle Bear Porn
      99.4K views
    • Simulated Quickie - Pussyboy Fuck Machine Training
      02:32
      Simulated Quickie - Pussyboy Fuck Machine Training
      Deleterious
      29K views
    • Inverted chastity cage - cock pushed inside of the body
      01:10
      Inverted chastity cage - cock pushed inside of the body
      Sissy Martina
      146.5K views
    • Sissy Maddy Blonde CD Anal Training
      11:43
      Sissy Maddy Blonde CD Anal Training
      Maddy Jones
      14.7K views
    • faggot in chastity cage get fucked from real man.
      00:21
      faggot in chastity cage get fucked from real man.
      180.5K views
    • Sissy Maddy is a very naughty gurl who loves big toys in her ass
      10:45
      Sissy Maddy is a very naughty gurl who loves big toys in her ass
      Maddy Jones
      12.7K views
    • Daddy Slave Cums in Chastity Cage
      03:24
      Daddy Slave Cums in Chastity Cage
      82.9K views
    • Showing Myself
      04:21
      Showing Myself
      KarinaSegal
      44.9K views
    • Slave cums from Fuck Machine
      00:37
      Slave cums from Fuck Machine
      s2mm4u
      165.3K views
    • January 2025 Live (part 1)
      30:55
      January 2025 Live (part 1)
      Ricky Cage
      36.9K views
    • Kept Locked and Used Relentlessly by My Masters: A Chastity Compilation
      11:23
      Kept Locked and Used Relentlessly by My Masters: A Chastity Compilation
      My Dirtiest Fantasy
      694.7K views
    • Sissy Maddy In A Tight Green Dress Fucks Her Ass With A Big Dildo
      04:54
      Sissy Maddy In A Tight Green Dress Fucks Her Ass With A Big Dildo
      Maddy Jones
      7.5K views
    • CBT and CUM Humiliation for Chastity Slave Doggy
      02:55
      CBT and CUM Humiliation for Chastity Slave Doggy
      Project Y studios
      143K views
    • Young Sissy Slut gets Fucked by bbc Daddy
      00:57
      Young Sissy Slut gets Fucked by bbc Daddy
      BlondeSissyHailey
      108.2K views
    • caged sub cum humiliation
      00:56
      caged sub cum humiliation
      201.8K views
    • Twink bondage bareback bdsm spunk cum control master and blond twink
      11:09
      Twink bondage bareback bdsm spunk cum control master and blond twink
      My Dirtiest Fantasy
      8.6K views
    • Cumshot while getting locked
      02:32
      Cumshot while getting locked
      Selfspanker
      12.5K views
    • Sissygasm Training 2
      10:58
      Sissygasm Training 2
      cdCrystal
      16.9K views
    • Oct 27 2025 - Straitjacketed Swimcap play
      25:15
      Oct 27 2025 - Straitjacketed Swimcap play
      StrapsKinks
      16.3K views
    • Sissy Fuckdoll 2
      12:57
      Sissy Fuckdoll 2
      cdCrystal
      3.2K views
    • Aicha does SPH humiliation cock comparison
      01:35
      Aicha does SPH humiliation cock comparison
      Cyber_Kink
      62.3K views
    • Rubber gimp used by slave and Master part 1 PREVIEW
      05:18
      Rubber gimp used by slave and Master part 1 PREVIEW
      EnglishLeathermaster
      5.5K views
    • Oliver Xbound
      11:12
      Oliver Xbound
      Marco Star
      187K views
    • Sissy Whore Training
      14:14
      Sissy Whore Training
      cdCrystal
      59.3K views
    • another humiliation with a big load on a caged tiny dick
      00:32
      another humiliation with a big load on a caged tiny dick
      320.6K views
    • Sissy Slut Training
      08:51
      Sissy Slut Training
      cdCrystal
      101.6K views
    • Insertion of the locking buttplug. The ultimate chastity.
      11:03
      Insertion of the locking buttplug. The ultimate chastity.
      Chastityexposed
      129.9K views
    • Sissy Maid Anal And Throat Play
      14:24
      Sissy Maid Anal And Throat Play
      Maddy Jones
      4.9K views
    • the final stage of feminization for a sissy slut
      00:50
      the final stage of feminization for a sissy slut
      562K views
    • hardcore chastity urethral sounding cumshot pov
      22:54
      hardcore chastity urethral sounding cumshot pov
      Selfspanker
      54.4K views
    • Bareback fuck will cost an extra
      14:30
      Bareback fuck will cost an extra
      My Dirtiest Fantasy
      66.3K views
    • Sissy Whore Training 2
      06:16
      Sissy Whore Training 2
      cdCrystal
      21.6K views
    • SISSYGASM IN CHASTITY
      09:11
      SISSYGASM IN CHASTITY
      Jett Ravage
      14.9K views
    • Beautiful Blonde Sissy Maddy Stuffing Her Ass With Big Toys
      18:49
      Beautiful Blonde Sissy Maddy Stuffing Her Ass With Big Toys
      Maddy Jones
      2.9K views
    • Training his new fuck boy
      26:39
      Training his new fuck boy
      1.1M views
    • Sissygasm Training
      08:48
      Sissygasm Training
      cdCrystal
      47.2K views
    • caged bottom fucked
      01:10
      caged bottom fucked
      224.8K views
    • Sissy whiteboi in stockings enjoys deep slow strokes on a veiny BBC dildo stretching his ass
      01:10
      Sissy whiteboi in stockings enjoys deep slow strokes on a veiny BBC dildo stretching his ass
      Cnje
      81.7K views
    • slutty blonde boy gets put in chastity
      06:13
      slutty blonde boy gets put in chastity
      138.6K 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 Chastity Training

    • Chastity Trainer
    • Sissy Training
    • Faggot Brainwashing
    • Gay Conversion Therapy
    • In Front of Wife
    • Learning to Become a Femboy
    • Crossdresser First Time
    • Master Trains Slave
    • Masturbation Instruction
    • Cock Worship Training
    • Sissy-Dani-In-Training
    • Public Locker Room
    • Pulling Back Foreskin
    • Wife's Bull Fucks Me
    • Sex Tutorial
    • Swallowing Masters Load
    • Dressed Like Woman
    • Wearing Lingerie
    • Cuckold Humiliation
    • Chastity 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