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

    Sissy Training Comp Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy Training Compilation
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Sissy #1: Accepting Your Destiny
      11:37
      Sissy #1: Accepting Your Destiny
      496.4K views
    • My Neighbor Fisting My Ass
      08:59
      My Neighbor Fisting My Ass
      Emmy Angeles
      146.4K views
    • Sissy's asshole is filled up to a meter deep
      17:25
      Sissy's asshole is filled up to a meter deep
      Drift3-4
      716.2K views
    • Ryley Rails Dominates You
      06:51
      Ryley Rails Dominates You
      TSRyley
      52.2K views
    • Sissy Throat Fuck Cum Swallow Training
      05:31
      Sissy Throat Fuck Cum Swallow Training
      444.8K views
    • My Biggest Anal Dildo Training Vf
      08:12
      My Biggest Anal Dildo Training Vf
      PrxcyTgirl
      56K views
    • Pornstar Ria Bentley Takes Giant BBC On Public Hotel Balcony
      07:06
      Pornstar Ria Bentley Takes Giant BBC On Public Hotel Balcony
      Ria_Bentley
      139.4K views
    • Fisting Double Sissygasm Cumshots
      01:38
      Fisting Double Sissygasm Cumshots
      Lola Spais
      160.7K views
    • Trained to Be Completely Subservient to Him
      08:12
      Trained to Be Completely Subservient to Him
      Pure Ts
      107.2K views
    • Big Breasted Sissy Oils Her Big Fat Tits and Enjoys a Big Fat Cock
      08:42
      Big Breasted Sissy Oils Her Big Fat Tits and Enjoys a Big Fat Cock
      Sissy Slut Chantal Sweet
      55K views
    • Extreme Anal Gape Xxxl Dildo & Fuck Machine
      05:56
      Extreme Anal Gape Xxxl Dildo & Fuck Machine
      Elvi Lynx
      64.6K views
    • Trans Girl Masturbating and Cums All Over Her Self
      03:44
      Trans Girl Masturbating and Cums All Over Her Self
      Bellaroar
      155.3K views
    • Sissy Chastity Maid Service Training With Ria Bentley
      07:07
      Sissy Chastity Maid Service Training With Ria Bentley
      Ria_Bentley
      42.7K views
    • The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)
      07:20
      The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)
      Sonechka25
      37.4K views
    • I fuck my stepsister's busty for her big pussy
      07:14
      I fuck my stepsister's busty for her big pussy
      Yeison
      2.3M views
    • Mistress Eudora's Anal Slut
      05:28
      Mistress Eudora's Anal Slut
      Loren Aprile
      148.4K views
    • SISSY TRANSFORMATION
      11:07
      SISSY TRANSFORMATION
      653.2K views
    • Admit That You Are a Slut For My Cum
      13:12
      Admit That You Are a Slut For My Cum
      Natalie Napoli
      335.2K views
    • Training to become a sissy cuckold
      03:26
      Training to become a sissy cuckold
      amatorxxx
      624.5K views
    • Jerk off While I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI
      07:47
      Jerk off While I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI
      Jessica Bloom
      328.6K views
    • AB094 Lustful teacher extreme trained -Milking 65cm dildo  (Chinese and English subtitles)
      03:52
      AB094 Lustful teacher extreme trained -Milking 65cm dildo (Chinese and English subtitles)
      Abby Kitty
      384.7K views
    • Relevant Short videos

      Dirty Sissy Maid Feet Comp
      Dirty Sissy Maid Feet Comp
      Lilly Disgrace
      511 views
      Sissy slave fuck and piss comp. | Clip 2
      Sissy slave fuck and piss comp. | Clip 2
      Bound_Sissy
      235 views
      Sissy slave fuck and piss comp. | Clip 1
      Sissy slave fuck and piss comp. | Clip 1
      Bound_Sissy
      266 views
      Sissy slave fuck and piss comp. | Clip 3
      Sissy slave fuck and piss comp. | Clip 3
      Bound_Sissy
      295 views
      ASMR - Monster on Shemale Compilation 1 -  (Headphones Advised)
      ASMR - Monster on Shemale Compilation 1 - (Headphones Advised)
      Ai Babes
      3.6K views
      Ultimate Shemale Cumshot Compilation
      Ultimate Shemale Cumshot Compilation
      Bellaroar
      1.2K views
    • SissyAline - Train your sissy pussy, be a buttslut
      09:06
      SissyAline - Train your sissy pussy, be a buttslut
      426.1K views
    • Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl
      05:43
      Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl
      alinanightsky
      344K views
    • TS Cumslut Elf Fucked Hard By Santa - Ass to Mouth And Facial Jessica Bloom
      06:43
      TS Cumslut Elf Fucked Hard By Santa - Ass to Mouth And Facial Jessica Bloom
      Jessica Bloom
      17.9K views
    • TRAIN YOUR SISSY PUSSY, BE A BUTTSLUT
      09:06
      TRAIN YOUR SISSY PUSSY, BE A BUTTSLUT
      556.5K views
    • POV housemate finds your panties and feminizes you JOI dominant trans girl
      11:53
      POV housemate finds your panties and feminizes you JOI dominant trans girl
      Holly unt
      165.9K views
    • Kira caught during self-bondage
      02:45
      Kira caught during self-bondage
      Twistedrama
      48.9K views
    • Assfucked by a Sissy
      13:01
      Assfucked by a Sissy
      Natalie Napoli
      15.6K views
    • Anal orgasm, cumshots in my mouth, compilation of my hot cumshots
      05:49
      Anal orgasm, cumshots in my mouth, compilation of my hot cumshots
      LuziaTv
      21.6K views
    • Petra,s day in the woods
      30:59
      Petra,s day in the woods
      PetraTVsletje
      89.5K views
    • Become the Whore - Sissy Slut
      07:00
      Become the Whore - Sissy Slut
      196.1K views
    • Cum ride with me
      12:10
      Cum ride with me
      Katie Fox
      452.1K views
    • Urethral Tube Stimulation with Chastity Cage
      07:00
      Urethral Tube Stimulation with Chastity Cage
      Reina Hanno
      46.2K views
    • Sissy Cum Training
      12:16
      Sissy Cum Training
      139.8K views
    • Story of when daddy pimped me out. First week. Anal toy.
      08:50
      Story of when daddy pimped me out. First week. Anal toy.
      Sunaxfemiknulla
      19.3K views
    • So You Think You're a Sissy Slut?
      06:37
      So You Think You're a Sissy Slut?
      Mistress Jodie May
      91.3K views
    • Sissy in Training
      01:27:33
      Sissy in Training
      384.2K views
    • Sissy 4: Cum Lover
      10:16
      Sissy 4: Cum Lover
      784.6K views
    • Will Sin Strips and Plays with Herself
      13:26
      Will Sin Strips and Plays with Herself
      Will__sin
      12.6K views
    • Sissy bitch training
      04:02
      Sissy bitch training
      128.1K views
    • Sissy Doll Fucking in a Pegging Date
      07:00
      Sissy Doll Fucking in a Pegging Date
      Brat Perversions
      17.4K 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
    • Sissy Slave Training
      15:45
      Sissy Slave Training
      1.5M views
    • Ryley Rails Edging JOI
      02:56
      Ryley Rails Edging JOI
      TSRyley
      10.9K views
    • Horny Sissy Slut Training
      05:28
      Horny Sissy Slut Training
      littlemissbrat
      264.1K 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
    • 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
    Previous page
    Next page
    1
    1. 1
    2. ...
    3. 5
    4. ...
    5. 8
    6. 9
    7. 10
    8. 11
    9. 12
    10. ...
    11. 45
    12. ...
    13. 80
    80

    Searches Related to Sissy Training Comp

    • Oiled up Sissy
    • Sissy Boy Training Slut
    • Sissy Maddis Is Back at It
    • Wants Training a Sissy Husband
    • Attitude Adjustment for Sissy Girl
    • Straight Guy Fucks Sissy
    • Sissy Perfect Trainer
    • Sissy CD Needs a Daddy
    • Ps Edit CD Sissy Bitch
    • Mmf DP BBC Sissy Training
    • Sissy Slut Progression Trainer
    • Made to Be Sissy
    • Sissy Boys Getting Fucked
    • Mistress Sissy Training
    • Sissy Slut Training Pmv
    • Sissy Getting Smooth
    • Sissy Girls Getting
    • Xtc Sissy Playtime
    • Sexy Sissy 4
    • I Love Fucking Sissy Boys Like You
    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