PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    WINTER MAGIC SALE ❄️☃️ Snowy discounts, hot deals!

    Sissy Work Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    HD
    Sissy Workout
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • LEYENDECKER PMV SISSY WORK
      04:29
      LEYENDECKER PMV SISSY WORK
      148.7K views
    • Annalicious sissy work part1
      04:07
      Annalicious sissy work part1
      145.3K views
    • Annalicious sissy work part3
      04:11
      Annalicious sissy work part3
      150.8K views
    • Annalicious sissy work part1
      14:54
      Annalicious sissy work part1
      41.6K views
    • Sucking some dudes cock while my boyfriend is at work
      05:18
      Sucking some dudes cock while my boyfriend is at work
      JsseMontz
      566.2K views
    • CD cam model gets fucked while working
      08:12
      CD cam model gets fucked while working
      Pure Ts
      47.7K views
    • The Boy Came Straight From Work to Fuck Me.
      08:22
      The Boy Came Straight From Work to Fuck Me.
      Tsdanisantos1
      160.6K views
    • Tranny dominates you at work
      07:05
      Tranny dominates you at work
      Kymmy Harper
      706.3K views
    • The End of a Work Week
      06:12
      The End of a Work Week
      Pure Ts
      17K views
    • Suck It Down Smoking JOI
      06:27
      Suck It Down Smoking JOI
      Darkfetish2k
      10K views
    • Sissy Caption - Reward him for his work, sissy.
      00:58
      Sissy Caption - Reward him for his work, sissy.
      364.4K views
    • Would You Suck Me After Working Out?
      03:30
      Would You Suck Me After Working Out?
      MadameMorganXXX
      23.8K views
    • Femboy Hooters Waitress Gets Fucked After Work
      07:54
      Femboy Hooters Waitress Gets Fucked After Work
      Pure Ts
      79.3K views
    • The End of a Work Week
      06:12
      The End of a Work Week
      Pure Ts
      9.9K 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
      502.3K views
    • Vlogmas 11.12.2025 We went to a hotel for work
      07:51
      Vlogmas 11.12.2025 We went to a hotel for work
      Veronica Sanders
      11.2K views
    • The New Maid Is Gonna Work Out Just Fine
      06:12
      The New Maid Is Gonna Work Out Just Fine
      Pure Ts
      8.1K views
    • Creamy Sloppy Blowjob Under The Counter Table at Work Place : Small Coffee
      08:01
      Creamy Sloppy Blowjob Under The Counter Table at Work Place : Small Coffee
      Asura
      48.8K 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
      278.6K views
    • Office work jerk
      03:30
      Office work jerk
      Michlle d
      167.6K views
    • a good blowjob after work for mister A.
      10:16
      a good blowjob after work for mister A.
      ClaraBCBG
      178K views
    • "i Work in the Seventh Heaven Bar." "you Are a Waiter?" "no I'm a Milk Maker.
      03:01
      "i Work in the Seventh Heaven Bar." "you Are a Waiter?" "no I'm a Milk Maker.
      XiangYan
      54K views
    • Sexy Thick sissy in fishnets at work
      05:29
      Sexy Thick sissy in fishnets at work
      Ruby Robby
      48.5K views
    • Sissy BBC Work
      08:05
      Sissy BBC Work
      77.9K views
    • Work Sissy
      06:12
      Work Sissy
      Pure Ts
      2.9K views
    • The Queen is largely derived from this work
      32:28
      The Queen is largely derived from this work
      Reynaldo6
      50.9K views
    • Sissy coming home from work
      16:12
      Sissy coming home from work
      SissyDaniella
      20.9K views
    • Your Work Review
      05:17
      Your Work Review
      Cassandra Lovit
      91.5K views
    • Cleaning slave working hard for cute tranny girl! Spitting! Assfuck! Mouthfuck! Deepthroat! Cum in mouth!
      01:17
      Cleaning slave working hard for cute tranny girl! Spitting! Assfuck! Mouthfuck! Deepthroat! Cum in mouth!
      TV_Helena
      18.4K views
    • After work guy fucks trans cute girl
      07:26
      After work guy fucks trans cute girl
      LittleVixenSlut
      5.4K views
    • He Doent Let Me Work so Naughty
      10:24
      He Doent Let Me Work so Naughty
      Stripchat official
      570K views
    • The New Maid Is Gonna Work Out Just Fine
      06:12
      The New Maid Is Gonna Work Out Just Fine
      Pure Ts
      2.6K views
    • busy truck stop whore slutwalk naked caught outdoor strangers
      02:25
      busy truck stop whore slutwalk naked caught outdoor strangers
      SusyTrav_AnalQueen
      9.6K views
    • Work Underling Becomes Secret Sissy Fucktoy
      08:12
      Work Underling Becomes Secret Sissy Fucktoy
      Pure Ts
      8.2K views
    • A tempting secretary changed her stocking after work and inserted anal plug without panty to prepare for the secret nightwork.
      13:59
      A tempting secretary changed her stocking after work and inserted anal plug without panty to prepare for the secret nightwork.
      Harinni
      6.3K views
    • Work Sissy
      06:12
      Work Sissy
      Pure Ts
      2.7K views
    • Showing myself off in my red bodycon dress. I get myself a little worked up again.
      06:27
      Showing myself off in my red bodycon dress. I get myself a little worked up again.
      JessicaXD
      1.8K views
    • How Should a Sissy at Work Dress
      03:26
      How Should a Sissy at Work Dress
      59.7K views
    • Working that mouth
      05:20
      Working that mouth
      Pandora Xysishe
      18.6K views
    • The First Thing He Does After Work
      07:42
      The First Thing He Does After Work
      Pure Ts
      5.7K views
    • Muscled Sissy Working Out Crazy Public Gym Exposure Cumshot
      06:52
      Muscled Sissy Working Out Crazy Public Gym Exposure Cumshot
      Sissy Jessica
      50.3K views
    • Playing in pretty panties
      03:12
      Playing in pretty panties
      Rachel_biTV_uk
      35.9K views
    • Playing with myself in the toilet
      04:04
      Playing with myself in the toilet
      Rachel_biTV_uk
      30.6K views
    • outdoor full naked chastity heels slutwalk at truck stop
      02:25
      outdoor full naked chastity heels slutwalk at truck stop
      SusyTrav_AnalQueen
      5.8K views
    • Larissa1sexdoll. Sissy Street Hooker. Queen of Spades
      05:23
      Larissa1sexdoll. Sissy Street Hooker. Queen of Spades
      Larissa1sexdoll
      71.8K views
    • public toilet full naked chastity heels slutwalk
      02:25
      public toilet full naked chastity heels slutwalk
      SusyTrav_AnalQueen
      7.4K views
    • Working from Home is so much fun with a Sissy Secretary.
      28:11
      Working from Home is so much fun with a Sissy Secretary.
      Lisa Essex
      113.2K 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 Work

    • Becoming Sissy
    • Sissyfication Process
    • Crossdresser Getting Fucked
    • Femboy Sissification
    • Are You a Sissy
    • Secret Sissyboy
    • Submissive Crossdresser Fucked Hard
    • Crossdressing Rent Boy
    • Crossdressers at Work
    • Femdom Feminization
    • Teen Destroyed
    • Femboy Gangbang
    • Straight Turned Sissy
    • Rough Sex
    • Cd BDSM
    • Turning Cuck Husband Into Faggot
    • Trans Gangbanged
    • First Time Crossdressing
    • Sissygasm Training
    • Crossdressers Hardcore
    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