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

    Sissy Trained Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Full HD
    HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • 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
      231.7K views
    • Sissy Play
      11:16
      Sissy Play
      Dark Films Trans
      5.9K views
    • Shemale Jane Fucks Marianne Mouth & Pussy Multi-position Creampie
      00:35
      Shemale Jane Fucks Marianne Mouth & Pussy Multi-position Creampie
      FapHouse
      just added
    • So You Think You're a Sissy Slut?
      06:37
      So You Think You're a Sissy Slut?
      Mistress Jodie May
      93K views
    • Slut Sucking Dick Until Cum
      08:12
      Slut Sucking Dick Until Cum
      c cdsluttasha
      628 views
    • Gorgeous Transsexual Stewardess Fucked Hard with Strapon
      02:49
      Gorgeous Transsexual Stewardess Fucked Hard with Strapon
      Lola Spais
      789 views
    • Trans Ria Bentley Trains Stepdaughter Eden Espi for Anal Sex
      08:12
      Trans Ria Bentley Trains Stepdaughter Eden Espi for Anal Sex
      FapHouse
      65.5K views
    • Do you have something better than this dildo I could suck on
      01:06
      Do you have something better than this dildo I could suck on
      Onlyfans
      just added
    • Shemale Jane Glory Hole Handjob & Blowjob From Seiko
      00:31
      Shemale Jane Glory Hole Handjob & Blowjob From Seiko
      FapHouse
      just added
    • Mistress Eudora's Anal Slut
      05:28
      Mistress Eudora's Anal Slut
      Loren Aprile
      153.6K views
    • Spandexfemboy - Anal Destruction with Huge BBC
      08:12
      Spandexfemboy - Anal Destruction with Huge BBC
      727 views
    • Shemale Jane Vivian Handjob Blowjob Footjob to Multi-position Fuck
      00:33
      Shemale Jane Vivian Handjob Blowjob Footjob to Multi-position Fuck
      Kathai Neram
      just added
    • Sissy in extreme deepthroat chastity upside down very wet and ruined make-up
      08:41
      Sissy in extreme deepthroat chastity upside down very wet and ruined make-up
      Vane03_siss
      1K views
    • Horny whore wants more dick in her asspussy
      05:10
      Horny whore wants more dick in her asspussy
      Sunaxfemiknulla
      480 views
    • Trans CD Queen Anal Destruction with Huge Dildo - Sissygasm
      01:36
      Trans CD Queen Anal Destruction with Huge Dildo - Sissygasm
      FapHouse
      856 views
    • Warming up My Cute Slutty Ass
      01:40
      Warming up My Cute Slutty Ass
      FapHouse
      358 views
    • Pink Satin Sissy Maid Gets Fucked by Her Fucking Machine and Plays with Her Sex Toy Doll
      08:25
      Pink Satin Sissy Maid Gets Fucked by Her Fucking Machine and Plays with Her Sex Toy Doll
      FapHouse
      609 views
    • Sissy in Micro Chastity Cage Shoving Two Bananas up Her Ass. Sissy in Body Stockings
      03:21
      Sissy in Micro Chastity Cage Shoving Two Bananas up Her Ass. Sissy in Body Stockings
      FapHouse
      just added
    • Your sissy boy training your sloppy ass to fisting
      07:10
      Your sissy boy training your sloppy ass to fisting
      FapHouse
      776 views
    • The Cucumber Sissygasm Session | Sissy Training
      01:10
      The Cucumber Sissygasm Session | Sissy Training
      Apple00001
      1K views
    • Sonechka tells how she managed to become a sissy whore. You just need to cum in your mouth everyday
      01:51
      Sonechka tells how she managed to become a sissy whore. You just need to cum in your mouth everyday
      FapHouse
      129.1K views
    • Sissy Academy, Lesson#1 “student Presentation”
      01:04
      Sissy Academy, Lesson#1 “student Presentation”
      Apple00001
      1.9K views
    • Worship Superior Foreskin
      06:50
      Worship Superior Foreskin
      obeylilith.com
      2.1K views
    • Sissy Training . How should she pee ? Like a real girl
      05:31
      Sissy Training . How should she pee ? Like a real girl
      Ashlie
      4.4K views
    • Dick slut enjoy anal destruction with horn dildo
      03:11
      Dick slut enjoy anal destruction with horn dildo
      Biguy6999
      245 views
    • Just because I can..
      18:29
      Just because I can..
      Twistedrama
      173.7K views
    • You're Just Some Holes, Slut!
      04:40
      You're Just Some Holes, Slut!
      Mistress Jodie May
      16.8K views
    • Sissy Dog Show
      02:08
      Sissy Dog Show
      Disciplinater
      17.7K views
    • Feminization Training - Show This To Your Wife
      07:58
      Feminization Training - Show This To Your Wife
      Holy
      68.8K views
    • BBC Blowjob
      06:12
      BBC Blowjob
      TSRyley
      3.1K 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
      14.1K views
    • Sissy Training After First Time Feminization
      12:20
      Sissy Training After First Time Feminization
      Onlyfans
      302.8K views
    • Crossdresser gets machine fucked with XXL Monster Dildos #4
      51:27
      Crossdresser gets machine fucked with XXL Monster Dildos #4
      Niceguy_1991
      195.4K views
    • Sissy training
      08:49
      Sissy training
      parttcrossdresser
      35.9K views
    • Sissy in Office
      06:38
      Sissy in Office
      SissyDaniella
      10.3K views
    • Sissy CD Kassy J Takes Huge Toy Deep in Her Tight Ass
      00:48
      Sissy CD Kassy J Takes Huge Toy Deep in Her Tight Ass
      Kassy Jones
      1K views
    • Big sissy training
      03:29
      Big sissy training
      FapHouse
      2.4K views
    • Slutty Couple Try New Hankey's Toys
      01:16
      Slutty Couple Try New Hankey's Toys
      Lola Spais
      9.1K views
    • Girls Fuck
      01:40
      Girls Fuck
      Many Vids
      4.2K views
    • FEMDOM SISSY TRAINNING COMPILATION
      05:39
      FEMDOM SISSY TRAINNING COMPILATION
      Lola Spais
      164.8K views
    • Ryley Rails JOI Sissy Training
      06:51
      Ryley Rails JOI Sissy Training
      TSRyley
      17.3K views
    • Sissy teasing leaving and arriving home
      14:23
      Sissy teasing leaving and arriving home
      SissyDaniella
      2.2K views
    • Sissy Trainning by Mistress Kira
      04:17
      Sissy Trainning by Mistress Kira
      Many Vids
      83.7K views
    • Sissy gothic cow with red hair and in chastity rides a big black dildo on her pillow
      13:41
      Sissy gothic cow with red hair and in chastity rides a big black dildo on her pillow
      Vane03_siss
      8.6K views
    • Sissy Femboy Bondage Feminization Training
      07:36
      Sissy Femboy Bondage Feminization Training
      Wraith931
      40.9K views
    • Sissy Candy's Dildo Post Compilation!
      09:24
      Sissy Candy's Dildo Post Compilation!
      FapHouse
      53K views
    • Microbikini Sissy Wearing a Girl’s Chastity Belt Takes 1.2L Up Her Ass
      07:39
      Microbikini Sissy Wearing a Girl’s Chastity Belt Takes 1.2L Up Her Ass
      Traviezisha
      3.4K views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 9
    9. ...
    10. 16
    16

    Searches Related to Sissy Trained

    • The Ultimate Sissy Trainer
    • Feminization Training
    • A Sissy's Purpose
    • Feminized and Fucked
    • Sissification Process
    • Secret Sissyboy
    • Transformed Into Slut
    • Crossdresser First Time
    • Femboy in Skirt
    • Caught Wearing Sisters Clothes
    • Male to Female Transformation
    • Sissyslut
    • Cross Dresser Solo
    • Stop Please Stop Dick Too Big
    • Successful Transition Mtf
    • Extreme Insertion
    • Most Feminine Girl Ever
    • Caged Sissies
    • Sissypink Boy
    • Riding Dildo Orgasm Talking Dirty
    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