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 POV
    Sissy Bukkake
    Sissy Whore
    Chastity Sissy
    French Sissy
    Sissy Orgasm
    Sissy Domination
    Sissy Public
    Sissy Moaning
    Sissy School
    Sissy Mistress
    Sissy Spanking
    Sissy Orgy
    Sissy Swallow
    Cute Sissy
    Sissy Fisting
    Sissy Bnwo
    Sissy Story
    Sissy Punishment
    Little Sissy
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • DEEP ANAL EXPLORING
      02:04
      DEEP ANAL EXPLORING
      Fogal101
      286.1K views
    • 4 Inch Wide Toy on Machine
      05:12
      4 Inch Wide Toy on Machine
      AmandaKnight
      45.6K views
    • Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune
      08:12
      Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune
      Fiona Fortune
      12.9K views
    • I have sex with my stepdaughter
      09:27
      I have sex with my stepdaughter
      karencita
      507.7K views
    • Faggot tax
      10:42
      Faggot tax
      95.4K views
    • verbal daddy part 3
      01:32
      verbal daddy part 3
      96.7K views
    • I fuck with my work partner in the living room of her house
      05:24
      I fuck with my work partner in the living room of her house
      Yeison
      505.6K views
    • BBC & Gloryholes (YOU NEED THIS)
      01:36
      BBC & Gloryholes (YOU NEED THIS)
      littlemissbrat
      70.3K views
    • So i hear you're a secret cocksucker?
      05:25
      So i hear you're a secret cocksucker?
      XXLUCYLUSHXX
      47.8K views
    • Sissy Jessica Bloom Teaches You How To Suck Cock And Swallow Cum
      07:28
      Sissy Jessica Bloom Teaches You How To Suck Cock And Swallow Cum
      Jessica Bloom
      59.8K views
    • Sissy training instructional
      17:12
      Sissy training instructional
      230.6K views
    • Sissy Training After First Time Feminization
      12:20
      Sissy Training After First Time Feminization
      Bailey Wilde
      300.8K views
    • Sissy Elvi Lynx's asshole EATS massive Dildos
      10:01
      Sissy Elvi Lynx's asshole EATS massive Dildos
      Elvi Lynx
      7.6K views
    • The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded
      10:53
      The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded
      alinanightsky
      274.9K views
    • Missy Foxx Time
      15:18
      Missy Foxx Time
      Dark Films Trans
      13.9K views
    • Sissy Boy Training Video: Surrender to Black Cocks
      04:20
      Sissy Boy Training Video: Surrender to Black Cocks
      855.6K views
    • Sissy Slave Fed Spit And Cum
      05:35
      Sissy Slave Fed Spit And Cum
      Jessica Bloom
      27.3K views
    • Petra,s graduation party
      01:14:05
      Petra,s graduation party
      PetraTVsletje
      11.2K views
    • At Her Mercy: Hot Trans Domme Trains You
      11:12
      At Her Mercy: Hot Trans Domme Trains You
      Melissa Masters
      41.6K views
    • My Big Ass, Anal Sex
      04:13
      My Big Ass, Anal Sex
      Apple00001
      117.5K views
    • Kimber Haven BBC Sissy Training
      08:45
      Kimber Haven BBC Sissy Training
      Kimberhaven
      90.9K views
    • Sissygasm Guide & How A Good Slut Cleans Up Jessica Bloom
      12:23
      Sissygasm Guide & How A Good Slut Cleans Up Jessica Bloom
      Jessica Bloom
      469.3K views
    • Petra's porno marathon part 1-3
      01:09:31
      Petra's porno marathon part 1-3
      PetraTVsletje
      103.3K views
    • Ultimate Sissy Fuck Doll Trainer
      03:00
      Ultimate Sissy Fuck Doll Trainer
      Ria_Bentley
      5.6K views
    • Sissy Boy Training
      04:08
      Sissy Boy Training
      784.6K views
    • Trans Girl Forced Orgasm
      08:12
      Trans Girl Forced Orgasm
      Mistress Jodie May
      107K views
    • Trained to Be a Submissive Slut
      08:12
      Trained to Be a Submissive Slut
      Pure Ts
      37.9K views
    • I fuck the pretty girl you do my wife's thing
      08:28
      I fuck the pretty girl you do my wife's thing
      Mariaa
      352.3K views
    • Bunny-butler Reina Hanno Sucking Two Dildos
      08:12
      Bunny-butler Reina Hanno Sucking Two Dildos
      Reina Hanno
      47.8K views
    • Sissy slut spitroast training with my fuck machine and dildos
      03:05
      Sissy slut spitroast training with my fuck machine and dildos
      trixied93
      6.3K views
    • Trans Girl Tied and Teased
      06:46
      Trans Girl Tied and Teased
      Mistress Jodie May
      129.8K views
    • Come cum inside me black daddy
      01:16
      Come cum inside me black daddy
      Dirtysissywhore
      109.4K views
    • Fuck me and suck me
      02:06
      Fuck me and suck me
      Viper Fierce
      152.5K views
    • Dreamscape Sissy training
      10:20
      Dreamscape Sissy training
      2.6M views
    • SISSY MAKER
      16:47
      SISSY MAKER
      172K views
    • Ghetto Faggot
      03:49
      Ghetto Faggot
      Kimberhaven
      144.6K views
    • Sissy Slut Training
      09:34
      Sissy Slut Training
      109.3K views
    • Submissive Ladyboy Anal Casting, Creampie & Slave Training
      01:25
      Submissive Ladyboy Anal Casting, Creampie & Slave Training
      FilmmakerDiaries
      12K views
    • Trained to be a sissy slut
      08:14
      Trained to be a sissy slut
      162.8K views
    • Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom
      08:11
      Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom
      Jessica Bloom
      117.1K views
    • Do You Believe in God? Futa Nun inviting Busty Luna to Join in Futanari Faith Church on Train
      07:30
      Do You Believe in God? Futa Nun inviting Busty Luna to Join in Futanari Faith Church on Train
      Asura
      79.2K views
    • White Sissy Trained & Used by BBC NYC Cop - PhillySissySlut
      01:07
      White Sissy Trained & Used by BBC NYC Cop - PhillySissySlut
      96.2K views
    • Tranny getting wild in the shower Riding that Dick
      04:59
      Tranny getting wild in the shower Riding that Dick
      CaliFauna
      142K views
    • I fuck my stepbrother's pussy with my big cock
      09:27
      I fuck my stepbrother's pussy with my big cock
      yesid
      96K views
    • Dirty Mistress Sissy JOI Training Jerk Off Instruction by Iskra Electrical
      08:05
      Dirty Mistress Sissy JOI Training Jerk Off Instruction by Iskra Electrical
      IskraElectrical49
      14K views
    • Trans Physical Therapist Ria Bentley Works Wonders On BBC Patient
      07:08
      Trans Physical Therapist Ria Bentley Works Wonders On BBC Patient
      Ria_Bentley
      279.6K views
    • Sissy Slut Jenni needs BBC Whore Training
      18:39
      Sissy Slut Jenni needs BBC Whore Training
      199K views
    Previous page
    Next page
    1
    1. 1
    2. ...
    3. 4
    4. 5
    5. 6
    6. 7
    7. 8
    8. ...
    9. 43
    10. ...
    11. 80
    80

    Searches Related to Training Sissy

    • Perverted
    • Trained
    • Degraded Whore
    • Triple XXX Private Full Movie
    • Sissyslut
    • Thrusting Butt Plug
    • Trans-Sex
    • Shemales Cum Remix
    • Girlfriend Catches Me Crossdressing
    • Don't Stop
    • Huge Insertions
    • Bodystocking
    • Changing Room
    • Mating Press
    • Passed Around
    • British Bareback
    • Extreme Insertion
    • Fucked Machine Chastity
    • Girlcock Brainwashing
    • Degrading
    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