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

    Training Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy Crossdresser
    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
    Sissy Boy
    Sissy Slut
    Sissy Faggot
    Sissy Cum
    Sissy Creampie
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • AMBERSIS SISSY CUM SLUT
      06:20
      AMBERSIS SISSY CUM SLUT
      471.6K views
    • I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI
      05:31
      I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI
      Melissa Wet Tales
      97.5K views
    • Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson
      05:29
      Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson
      655.7K views
    • Sissy in Training
      01:27:33
      Sissy in Training
      384.2K 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
      308.2K views
    • Sissy 4: Cum Lover
      10:16
      Sissy 4: Cum Lover
      784.6K views
    • Daddy's Good Girl!
      08:12
      Daddy's Good Girl!
      Pure Ts
      938.3K views
    • Will Sin Strips and Plays with Herself
      13:26
      Will Sin Strips and Plays with Herself
      Will__sin
      11.6K views
    • 2032 - the Bwno Future
      15:06
      2032 - the Bwno Future
      ChristineWest120
      114.8K views
    • Sissy bitch training
      04:02
      Sissy bitch training
      128.1K views
    • Sissy Joyce - A real life sissy slave
      01:16
      Sissy Joyce - A real life sissy slave
      Sissy Joyce
      691.4K views
    • Sissy Doll Fucking in a Pegging Date
      07:00
      Sissy Doll Fucking in a Pegging Date
      Brat Perversions
      17.4K views
    • Feminize Yourself
      16:07
      Feminize Yourself
      447.2K views
    • horny skinny mistress JOI and CEI make u my sissy fuck hole
      05:22
      horny skinny mistress JOI and CEI make u my sissy fuck hole
      Nadja Cox
      250.6K views
    • AMBERSIS SISSY HOLE TRAINING
      17:41
      AMBERSIS SISSY HOLE TRAINING
      131.5K views
    • Sissy Slave Training
      15:45
      Sissy Slave Training
      1.5M views
    • CD TRAP SISSY EDUCATION TRAINING 101
      01:27:33
      CD TRAP SISSY EDUCATION TRAINING 101
      932.9K views
    • Ryley Rails Edging JOI
      02:56
      Ryley Rails Edging JOI
      TSRyley
      10.9K views
    • YOUR MIND IS WEAK SISSY
      05:54
      YOUR MIND IS WEAK SISSY
      524.5K views
    • Horny Sissy Slut Training
      05:28
      Horny Sissy Slut Training
      littlemissbrat
      262.9K views
    • mistress cages sissy
      12:29
      mistress cages sissy
      947.4K views
    • sissy training
      15:28
      sissy training
      421.9K 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
      222.4K views
    • Trans Slut Will Receive Anal Training From a Dominant Woman
      03:47
      Trans Slut Will Receive Anal Training From a Dominant Woman
      Emmy Angeles
      19.2K views
    • Kimber's BBC Sissy Trainer
      19:45
      Kimber's BBC Sissy Trainer
      Kimberhaven
      210.6K views
    • Serving Mr. Maxxx (thad Fucks Brie Lovely and Ryley Rails)
      37:03
      Serving Mr. Maxxx (thad Fucks Brie Lovely and Ryley Rails)
      Brie Lovely
      7.7K views
    • sissy Cock Worship
      04:53
      sissy Cock Worship
      568.8K views
    • Sissy Poppers Hypnose Training III
      21:45
      Sissy Poppers Hypnose Training III
      282.8K views
    • You are a woman -sissy trainer
      04:12
      You are a woman -sissy trainer
      358.4K views
    • ..BLOW YOUR MIND.. - TGIRS & GIRLS PMV
      04:37
      ..BLOW YOUR MIND.. - TGIRS & GIRLS PMV
      324.3K views
    • How to Train Your Sissy Boyfriend
      08:12
      How to Train Your Sissy Boyfriend
      Brat Perversions
      112.7K views
    • Sissy Maid Gets Locked in Bondage and Chastity to Be Fucked by Her Sex Doll
      23:36
      Sissy Maid Gets Locked in Bondage and Chastity to Be Fucked by Her Sex Doll
      Sissy Candy
      30.9K views
    • Feminize Yourself
      15:44
      Feminize Yourself
      190K views
    • Threesome Sissy Domination
      08:12
      Threesome Sissy Domination
      TSRyley
      8.4K views
    • Rented Out by His Mistress
      06:12
      Rented Out by His Mistress
      Pure Ts
      64K views
    • Sissy Whiteboy Training
      01:23:19
      Sissy Whiteboy Training
      204.6K views
    • Cocklust sissy trainer
      09:38
      Cocklust sissy trainer
      211K views
    • Ryley Rails JOI Sissy Training
      06:51
      Ryley Rails JOI Sissy Training
      TSRyley
      16.1K views
    • Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage
      10:16
      Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage
      Jessica Bloom
      72.8K views
    • Daddy domination over his sissy sex slave and to taught her that my place is under his balls
      02:46
      Daddy domination over his sissy sex slave and to taught her that my place is under his balls
      alinanightsky
      141.2K views
    • Sissy Slut Motel
      58:39
      Sissy Slut Motel
      727K views
    • Sissy chastity training
      08:23
      Sissy chastity training
      227.1K views
    • I turned my straight roommate intro trans wife
      05:20
      I turned my straight roommate intro trans wife
      CutePinkUnicorn
      510.2K views
    • the DREAM of the girl next door, a sporty trans girl after training puts her boyfriend to suck in the kitchen
      01:24
      the DREAM of the girl next door, a sporty trans girl after training puts her boyfriend to suck in the kitchen
      GiGiMoon81
      160.9K views
    • sissy feminization instructions
      07:22
      sissy feminization instructions
      255.2K views
    • An Extraordinary Sex Session with This Extraordinary Sissy Who Breaks All the Rules!
      18:08
      An Extraordinary Sex Session with This Extraordinary Sissy Who Breaks All the Rules!
      Trans and Co
      11K views
    • A White Boys Purpose
      23:50
      A White Boys Purpose
      Kimberhaven
      603.2K views
    Previous page
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 42
    9. ...
    10. 80
    80

    Searches Related to Training Sissy

    • Whored Out
    • Transvestite Spanking Maid
    • Combat Zone Transsexual Barebacking
    • Straight Test
    • Bound Sluts
    • Sissygurl Fe Fe
    • Transgender Orgy
    • Male to Female Transformation Fantasy
    • Sissy Submission Training
    • Dildo Hero
    • Pussy Torture
    • Church Sisters
    • Role Play
    • Men Dressed as Women
    • Truth or Dare
    • Sissykanisa
    • Not Gay
    • Transexual Beauty Queen
    • Pegging Orgasm
    • T Girls Experience
    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