PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels

    Chastity Training Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Femdom Chastity
    Chastity BBC
    Inverted Chastity
    Bbc Chastity
    Chastity Orgasm
    Flat Chastity
    Feminization Training
    Slave Training
    Bbc Training
    Chastity Creampie
    Cum Training
    Femboy Training
    Ladyboy Chastity
    Cocksucker Training
    Asian Chastity
    Faggot Training
    Chastity Strapon
    Latex Chastity
    Chastity Anal
    Cuckold Chastity
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • How to train your sissy ass
      17:41
      How to train your sissy ass
      659.7K views
    • Sissy Maid Service Practicing on a Dildo at Her Fake Glory Hole
      18:20
      Sissy Maid Service Practicing on a Dildo at Her Fake Glory Hole
      Sissy Candy
      20.9K views
    • Damazonia & Natalie Mars - Anal Fisting Strapon
      15:55
      Damazonia & Natalie Mars - Anal Fisting Strapon
      293.5K views
    • Pink Sissy Maid Caught Dressing and Playing and Has a Sissygasm Riding Her Doll
      11:21
      Pink Sissy Maid Caught Dressing and Playing and Has a Sissygasm Riding Her Doll
      Sissy Candy
      51.8K views
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.4M views
    • Sissy Oksana cums very profusely during anal dildo training
      13:54
      Sissy Oksana cums very profusely during anal dildo training
      Oksana2021
      156.1K views
    • So Strongly Fucked That I Was Wet Myself
      02:44
      So Strongly Fucked That I Was Wet Myself
      XiangYan
      81.9K views
    • POV: Young Gothic Sissy Girl Comes Home And Takes Care Of Your Cock
      09:58
      POV: Young Gothic Sissy Girl Comes Home And Takes Care Of Your Cock
      Vane03_siss
      88.2K views
    • Flat Chastity Sissy
      21:45
      Flat Chastity Sissy
      Juahlovely
      112.7K views
    • POV: Your gothic trans mistress puts you in chastity and makes fun of you, putting handcuffs on you and making you worship her feet.
      07:37
      POV: Your gothic trans mistress puts you in chastity and makes fun of you, putting handcuffs on you and making you worship her feet.
      Vane03_siss
      27.6K views
    • How to Put on Flat Chastity Cage Guide (Jessica Bloom)
      06:08
      How to Put on Flat Chastity Cage Guide (Jessica Bloom)
      Jessica Bloom
      33.6K views
    • PorchaeTS tries new homemade chastity Dick dildo to pleasure the Mrs. Total mind trip.
      04:42
      PorchaeTS tries new homemade chastity Dick dildo to pleasure the Mrs. Total mind trip.
      PorchaeTS
      90.3K views
    • All sissy should be loked in chastity
      03:26
      All sissy should be loked in chastity
      345.6K views
    • Trans Anal Training Cumming Twice From Monster Dildo Hard And Caged
      07:25
      Trans Anal Training Cumming Twice From Monster Dildo Hard And Caged
      Jessica Bloom
      3.4K views
    • Inverted Chastity Off, Itty Bitty Clitty Gets Sounded, Pushed Back in & Locked up Again!
      07:37
      Inverted Chastity Off, Itty Bitty Clitty Gets Sounded, Pushed Back in & Locked up Again!
      MJ
      202.9K views
    • Sissy riding dildo outside
      10:45
      Sissy riding dildo outside
      SissyDaniella
      27.1K views
    • Sissy sex slave
      32:34
      Sissy sex slave
      564.1K views
    • Gothic Sissy Slut In Pink Dress Workouts With Her BBC Dildo
      09:16
      Gothic Sissy Slut In Pink Dress Workouts With Her BBC Dildo
      Vane03_siss
      20.6K views
    • Jessica Bloom Dominates Her new Pig Fuck Toy Jenby Doll
      06:23
      Jessica Bloom Dominates Her new Pig Fuck Toy Jenby Doll
      Jessica Bloom
      236.9K views
    • Caged Sissy try get pleasure by anal dildo play
      11:54
      Caged Sissy try get pleasure by anal dildo play
      SissyDaniella
      30.5K 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
      73K views
    • Chastity fox ninja cosplay and huge anal dildo destruction
      15:35
      Chastity fox ninja cosplay and huge anal dildo destruction
      AngelSissyWhore
      11.6K 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
    • Sissy Dog Show
      02:08
      Sissy Dog Show
      Disciplinater
      16.5K views
    • Kate becomes daddy's slave
      02:12
      Kate becomes daddy's slave
      AcrylicCloud
      96.3K views
    • Sissy Candy in Lingerie Gets Fucked by Her Machine with a Huge Dildo
      07:55
      Sissy Candy in Lingerie Gets Fucked by Her Machine with a Huge Dildo
      Sissy Candy
      46.8K views
    • Sex Chair
      03:06
      Sex Chair
      XiangYan
      65.6K views
    • Sissy coming home from work
      16:12
      Sissy coming home from work
      SissyDaniella
      20.9K views
    • Bound sissy in chastity gets BBC
      07:46
      Bound sissy in chastity gets BBC
      949.6K views
    • Sissy Candy in Red Lingerie Gets Spitroasted by Her Fucking Machine and Doll
      08:25
      Sissy Candy in Red Lingerie Gets Spitroasted by Her Fucking Machine and Doll
      Sissy Candy
      21.5K views
    • Mistress Gives Her Caged Sissy a little Spanking – Obedience and Discipline Lesson
      05:13
      Mistress Gives Her Caged Sissy a little Spanking – Obedience and Discipline Lesson
      Lucy Dee
      9.4K views
    • Sissy in Pink Dress and Chastity Plays with Her Butt Plug and Gets Fucked Hard by Machine
      16:04
      Sissy in Pink Dress and Chastity Plays with Her Butt Plug and Gets Fucked Hard by Machine
      Sissy Candy
      16.1K 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
      225.1K views
    • POV/JOI: Your trans friend helps you jerk off to the alternative and original green light, red light game, by pulling dice out of her ass
      21:40
      POV/JOI: Your trans friend helps you jerk off to the alternative and original green light, red light game, by pulling dice out of her ass
      Vane03_siss
      18.8K views
    • Super-Sissy Natalie Mars
      02:11
      Super-Sissy Natalie Mars
      332.4K views
    • trans sissy slut with blue hair going crazy with big dildos - MercurySissy aka Mercury Montana  riding and training in chastity
      05:38
      trans sissy slut with blue hair going crazy with big dildos - MercurySissy aka Mercury Montana riding and training in chastity
      MercurySissy
      48.5K views
    • Sissy in chastity fucked by different people
      01:41
      Sissy in chastity fucked by different people
      Sissy Joyce
      530.5K views
    • Sissy fucking new pussy hole
      15:06
      Sissy fucking new pussy hole
      SissyDaniella
      12.3K views
    • I'll fill your asshole with cum to overflowing
      06:01
      I'll fill your asshole with cum to overflowing
      MrNastyXavier
      1.9M views
    • Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm
      13:54
      Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm
      Sissy Candy
      41K views
    • Together in a life of chastity
      09:44
      Together in a life of chastity
      Katie Fox
      141.5K views
    • 2 sissy latex nurses getting pegged in Chastity by MILF Lisa
      11:47
      2 sissy latex nurses getting pegged in Chastity by MILF Lisa
      Lisa Essex
      119.2K views
    • sissy training
      39:53
      sissy training
      134.3K views
    • Sissy in Black Lingerie Gets Fucked by Her Fucking Machine
      39:50
      Sissy in Black Lingerie Gets Fucked by Her Fucking Machine
      Sissy Candy
      3.1K views
    • mistress cages sissy
      12:29
      mistress cages sissy
      947.4K views
    • Sissy Candy's Dildo Post Compilation!
      09:24
      Sissy Candy's Dildo Post Compilation!
      Sissy Candy
      52.2K views
    • TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
      01:19
      TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
      Princesszoey
      80.9K views
    Previous page
    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

    • Masturbation Instructions
    • Ball Busting
    • Uncensored
    • Successful Transition Mtf
    • Fuck Me Fuck Me Fuck Me
    • Dirty Little Secret
    • Prostate Vibrator
    • Self Bondage
    • Lossing Virginity
    • Cock Under Dress
    • Trap Toy
    • Out of Control
    • Israeli Army Girls
    • Beautiful Trans Women XXX
    • Hotel Room With Stepmom
    • Homemade Single Mom
    • Amateur Sissygasm
    • Ballbusting
    • Feminized Hormones
    • Stop Please Stop Dick Too Big
    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