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

    Sissy Training Night Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.2M views
    • Cock Whore Sissy's Training Night (Audio Erotica)
      10:10
      Cock Whore Sissy's Training Night (Audio Erotica)
      littlemissbrat
      38.5K views
    • My wife told me to play this
      11:13
      My wife told me to play this
      973.2K views
    • BBC my training night and sissy slut
      13:27
      BBC my training night and sissy slut
      2.6K views
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3.1M views
    • sissy training last night at hotel.
      00:59
      sissy training last night at hotel.
      38.3K views
    • Sissy #2: Becoming A Cock Slut
      15:35
      Sissy #2: Becoming A Cock Slut
      873.6K views
    • Late Night Sissy Training
      01:42
      Late Night Sissy Training
      littlemissbrat
      15.9K views
    • Sissy cum dump compilation
      28:49
      Sissy cum dump compilation
      2.7M 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
      144.1K views
    • How to train your sissy ass
      17:41
      How to train your sissy ass
      665.9K views
    • Slut Beril Who Trains At Home Goes For A Walk Outside Public +18 Coward
      05:07
      Slut Beril Who Trains At Home Goes For A Walk Outside Public +18 Coward
      Usaberilx
      17.2K views
    • family fun 1.mp4
      13:05
      family fun 1.mp4
      1.8M views
    • Sissy Vanessa comes home after a night at the disco and trains anally with her dildos
      10:15
      Sissy Vanessa comes home after a night at the disco and trains anally with her dildos
      Vane03_siss
      34.6K views
    • Loser Boyfriend Gets Feminized and Fucked
      08:12
      Loser Boyfriend Gets Feminized and Fucked
      Pure Ts
      300.5K views
    • Mature Sissy CD out on a warm November Night solo fun crossdresser whore.
      03:08
      Mature Sissy CD out on a warm November Night solo fun crossdresser whore.
      JonasBen
      28.3K views
    • girlcock brainwashing - sink even deeper
      17:10
      girlcock brainwashing - sink even deeper
      400.1K views
    • SisK CD in purple EP2 dressing up sexy silky panties.
      11:25
      SisK CD in purple EP2 dressing up sexy silky panties.
      SissyKanisa
      46.4K views
    • Male to female gender transformation smoking whore
      16:00
      Male to female gender transformation smoking whore
      700.3K views
    • Outdoor Public Slutwalk in Sexy Pink Outfit
      03:29
      Outdoor Public Slutwalk in Sexy Pink Outfit
      FapHouse
      3.6K views
    • Sissy Dreams 3
      26:07
      Sissy Dreams 3
      1.2M views
    • Relevant Short videos

      Powerful moment from "Pornstar Ria Bentley Takes Giant BBC On Public Hotel Balcony"
      Powerful moment from "Pornstar Ria Bentley Takes Giant BBC On Public Hotel Balcony"
      Ria_Bentley
      6.8K views
      Solo Honeymoon Muscle Bitch
      Solo Honeymoon Muscle Bitch
      Sissy Jessica
      674 views
      Outdoor Public Slutwalk in Sexy Pink Outfit
      Outdoor Public Slutwalk in Sexy Pink Outfit
      FapHouse
      943 views
      Memorable moment from "Mature Sissy CD out on a warm November Night solo fun crossdresser whore."
      Memorable moment from "Mature Sissy CD out on a warm November Night solo fun crossdresser whore."
      JonasBen
      518 views
      Michelle Ernandes Waking up After a Hot Party Night Still Wearing Expensive Sexy Lingerie
      Michelle Ernandes Waking up After a Hot Party Night Still Wearing Expensive Sexy Lingerie
      FapHouse
      53 views
      Sissy in Slutty Dress Masturbating Her Ass in Public ATM with Dildo at Night
      Sissy in Slutty Dress Masturbating Her Ass in Public ATM with Dildo at Night
      Traviezisha
      364 views
    • Sissy Crossdresser in Chastity Walking in the Streets at Night with a Fox Tail Anal Plug Inside Her
      02:01
      Sissy Crossdresser in Chastity Walking in the Streets at Night with a Fox Tail Anal Plug Inside Her
      Traviezisha
      1.4K views
    • Sissy #3: Feminize Yourself
      16:07
      Sissy #3: Feminize Yourself
      661.4K views
    • Night walk at train station and parking lot with fishnet stocking
      03:26
      Night walk at train station and parking lot with fishnet stocking
      Niya_cd
      20.7K views
    • A guide to sissication: Beginner - Am I a sissy?
      23:32
      A guide to sissication: Beginner - Am I a sissy?
      762.7K views
    • Red-haired sissy Sonechka was almost caught on the staircase during anal self-pleasure
      06:29
      Red-haired sissy Sonechka was almost caught on the staircase during anal self-pleasure
      FapHouse
      7.5K views
    • Daddy's Good Girl!
      08:12
      Daddy's Good Girl!
      Pure Ts
      963.5K views
    • Sissy in Chastity and Slutty Lingerie Masturbating Her Ass with Dildo in a Public Park at Night.
      01:24
      Sissy in Chastity and Slutty Lingerie Masturbating Her Ass with Dildo in a Public Park at Night.
      FapHouse
      1.2K views
    • SISSY TEST CHECK HOW NAUGHTY SLUT YOU ARE
      07:22
      SISSY TEST CHECK HOW NAUGHTY SLUT YOU ARE
      714K views
    • Saturday Night Life
      01:07
      Saturday Night Life
      Starbutts
      2.2K views
    • I'll fill your asshole with cum to overflowing
      06:01
      I'll fill your asshole with cum to overflowing
      MrNastyXavier
      2M views
    • Michelle Ernandes Waking up After a Hot Party Night Still Wearing Expensive Sexy Lingerie
      08:12
      Michelle Ernandes Waking up After a Hot Party Night Still Wearing Expensive Sexy Lingerie
      FapHouse
      355 views
    • dominant stepmom helps out her sissy slave
      05:59
      dominant stepmom helps out her sissy slave
      Pure Ts
      382.9K views
    • Outdoors, near my place
      04:54
      Outdoors, near my place
      Simone Xdressing
      5.8K views
    • Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
      29:33
      Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
      FapHouse
      2.6M views
    • Sissy in Slutty Dress Masturbating Her Ass in Public ATM with Dildo at Night
      00:49
      Sissy in Slutty Dress Masturbating Her Ass in Public ATM with Dildo at Night
      Traviezisha
      1.1K views
    • Real sissy hypnotic
      24:43
      Real sissy hypnotic
      232.5K views
    • Kanisa on Purple Night Gown Ep2: Riding Dildo
      06:49
      Kanisa on Purple Night Gown Ep2: Riding Dildo
      FapHouse
      5.1K views
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.4M views
    • cycling at night
      06:53
      cycling at night
      Simone Xdressing
      2.2K views
    • Feminization Positivity Trainer
      03:20
      Feminization Positivity Trainer
      716.4K views
    • Kanisa on Purple Night Gown Ep1: Gets Anal Fuck by a Colorful Dildo
      08:12
      Kanisa on Purple Night Gown Ep1: Gets Anal Fuck by a Colorful Dildo
      FapHouse
      4.3K views
    • Sissy  Mind Fuck
      09:35
      Sissy Mind Fuck
      759.2K views
    • Down in the tunnel..., again...
      10:40
      Down in the tunnel..., again...
      Simone Xdressing
      2.8K views
    • Your friendly Sissy Trainer GERMAN
      09:22
      Your friendly Sissy Trainer GERMAN
      561.1K views
    • Slutty night training
      04:44
      Slutty night training
      Pinky Susy
      1.3K views
    • Guy loses bet turns into sissy CD giving blowjob
      04:52
      Guy loses bet turns into sissy CD giving blowjob
      1.3M views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80

    Searches Related to Sissy Training Night

    • Sissy for Ever
    • Whore Training
    • Turned Into a Submissive Gurl
    • Secret Sissyboy
    • Feminized and Fucked
    • Your Fantasy T-Girl Slut
    • The Slutty Maid
    • Wife Fucking Sissysissy Slave Extreme
    • Pretty Crossdresser Teacher
    • Dirty Talking Sissys
    • Sissies in Chastity
    • Sissystudent Daily BBC Conditioning
    • Crossdressed X
    • Gangbang Cds
    • Bad Boy Ftm [Deactivated]
    • Femdom Humiliation
    • Sissy's World
    • Sissification 2 Part 2
    • Girls Frontline R34
    • Hands Free Sissygasm
    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