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

    Sissy At Work Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy Slut
    Sissy Faggot
    Sissy Cum
    Sissy Creampie
    Sissy Humiliation
    Sissy Anal
    Sissy Caption
    Sissy Bondage
    Sissy Trainer
    Transvestites Sissies
    Asian Sissy
    Homemade Sissy
    Sissy JOI
    Sissy BDSM
    Sissy Daddy
    Sissy Pegging
    Sissy Femboy
    Black Sissy
    Russian Sissy
    Sissy Maker
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Male to female gender transformation smoking whore
      16:00
      Male to female gender transformation smoking whore
      692K views
    • riding my toyfriend at work on a chair
      01:20
      riding my toyfriend at work on a chair
      DeeAmazonDoll
      1.6K views
    • Entering the Feminization Academy
      08:12
      Entering the Feminization Academy
      Pure Ts
      105.8K views
    • Playing pussy in the locker room. Breaktime at work
      02:17
      Playing pussy in the locker room. Breaktime at work
      Kibis
      671 views
    • Tgirl gets Fucked in Anal while talking to a barmaid
      19:04
      Tgirl gets Fucked in Anal while talking to a barmaid
      MySchoolLife
      670.5K views
    • Playing pussy in the locker room. Breaktime at work
      02:56
      Playing pussy in the locker room. Breaktime at work
      Kibis
      903 views
    • Mature CD Girlfriends End up with the Same Guy
      08:12
      Mature CD Girlfriends End up with the Same Guy
      Pure Ts
      67.3K views
    • Latex nun on the roof  quickie at work .
      04:16
      Latex nun on the roof quickie at work .
      Alison loves latex
      2K views
    • Dating a mature crossdresser
      08:12
      Dating a mature crossdresser
      Pure Ts
      234.8K views
    • At work fun
      00:37
      At work fun
      1.1K views
    • Auditioning for the drag show
      08:12
      Auditioning for the drag show
      Pure Ts
      65.3K views
    • a day at work of a transvestite
      10:07
      a day at work of a transvestite
      Adikiki
      6.4K views
    • Job interview leads to some intense sex
      08:12
      Job interview leads to some intense sex
      Pure Ts
      161.8K views
    • femboy Lexiamber and her small cock are playing in the bathtub of her girlfriend who is at work
      03:37
      femboy Lexiamber and her small cock are playing in the bathtub of her girlfriend who is at work
      Lexiamber
      1.6K views
    • Petra,s day in the woods
      30:59
      Petra,s day in the woods
      PetraTVsletje
      85.1K views
    • Playing pussy in the locker room. Breaktime at work
      01:15
      Playing pussy in the locker room. Breaktime at work
      Kibis
      687 views
    • 2 Mommies Training Their TS Slut - Lucy Hart - Penny Barber - Mira Maven
      15:07
      2 Mommies Training Their TS Slut - Lucy Hart - Penny Barber - Mira Maven
      Lucy Hart
      378.3K views
    • Our neighborhood friendly spider-man at work
      05:26
      Our neighborhood friendly spider-man at work
      Canbfem
      9K views
    • shemale dresses sissy to fuck
      16:14
      shemale dresses sissy to fuck
      2.1M views
    • At work
      02:54
      At work
      Pantygirl
      1.1K views
    • Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
      08:12
      Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
      nbnabunny
      1.6M views
    • Sissy maid at work
      03:27
      Sissy maid at work
      4.2K views
    • Superstar Crossdresser Loves Doing Her Duty
      08:12
      Superstar Crossdresser Loves Doing Her Duty
      Pure Ts
      85.1K views
    • Jasmine_dlight & Miss Lolalu - Stress Relief After a Hard Day at Work - Shemale Fucktoy Servicing Her Mistress
      00:31
      Jasmine_dlight & Miss Lolalu - Stress Relief After a Hard Day at Work - Shemale Fucktoy Servicing Her Mistress
      Jasmine_dlight
      3.4K views
    • Video editing session turns into a kinky bi and trans foursome orgy
      40:50
      Video editing session turns into a kinky bi and trans foursome orgy
      Spike Essex
      1.2M views
    • Entertainer Lady boy at work
      05:17
      Entertainer Lady boy at work
      Canbfem
      3.5K views
    • dominant stepmom helps out her sissy slave
      05:59
      dominant stepmom helps out her sissy slave
      Pure Ts
      364.9K views
    • Sissy Annabelle at work with her Dildo
      02:15
      Sissy Annabelle at work with her Dildo
      1.5K views
    • Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
      01:17
      Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
      Allmylinks
      100.6K views
    • The Boy Came Straight From Work to Fuck Me.
      08:22
      The Boy Came Straight From Work to Fuck Me.
      Tsdanisantos1
      153.5K views
    • Sissys in chastity
      03:40
      Sissys in chastity
      770.2K views
    • The End of a Work Week
      06:12
      The End of a Work Week
      Pure Ts
      15.9K views
    • I finally let my stepsis fuck my trans pussy
      05:30
      I finally let my stepsis fuck my trans pussy
      CutePinkUnicorn
      611.5K views
    • Sissy Caption - Reward him for his work, sissy.
      00:58
      Sissy Caption - Reward him for his work, sissy.
      362K views
    • Many crossdressers fucked scrnrs
      01:09:02
      Many crossdressers fucked scrnrs
      1.4M views
    • Suck It Down Smoking JOI
      06:27
      Suck It Down Smoking JOI
      Darkfetish2k
      9K views
    • Never Expecting to Be a Sexy Girl
      08:12
      Never Expecting to Be a Sexy Girl
      Pure Ts
      466.7K views
    • Would You Suck Me After Working Out?
      03:30
      Would You Suck Me After Working Out?
      MadameMorganXXX
      22.5K views
    • Fake Job Interview Bags a Crossdresser
      06:12
      Fake Job Interview Bags a Crossdresser
      Pure Ts
      31.1K views
    • Fucking My Ass While Working Hehe
      03:37
      Fucking My Ass While Working Hehe
      lorenahotting
      15.5K views
    • This happened to me leaving school
      19:20
      This happened to me leaving school
      ELIZABETH LARA
      4.2M views
    • Femboy Hooters Waitress Gets Fucked After Work
      07:54
      Femboy Hooters Waitress Gets Fucked After Work
      Pure Ts
      77.6K views
    • Sissy cums too early and gets punished with rough fucking
      02:35
      Sissy cums too early and gets punished with rough fucking
      2.1M views
    • The New Maid Is Gonna Work Out Just Fine
      06:12
      The New Maid Is Gonna Work Out Just Fine
      Pure Ts
      7.2K views
    • Trans Taking an Anal Virginity
      08:12
      Trans Taking an Anal Virginity
      Mistress Jodie May
      384.7K 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
      497.8K views
    • How to Train Your Sissy Boyfriend
      08:12
      How to Train Your Sissy Boyfriend
      Brat Perversions
      106.2K views
    Previous page
    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 At Work

    • Feminized by Wife
    • White Femboys Are so Submissive
    • Shemale Sissification
    • Cute Traps for Straight Guys
    • Cock Peeking Out of Her Skirt Dress
    • Crossdreser Sex
    • Guy Gets Transformed Into Drag Queen
    • Femboy Schoolgirl
    • Two Sissies
    • Crossdressers at Work
    • Sissy_tammy Leaked
    • Sissynat
    • Sissygurl Fe Fe
    • Fuck My Ass Please Dirty Talk
    • Girlfriend Catches Me Crossdressing
    • Daddy's Girl
    • Crossdressed Flight Attendant
    • Bratty Sis
    • Breeding Cds From the Top Position
    • Amateur 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