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

    Old Boss Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    4K
    HD
    Full HD
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Djinn - Martha is a cum dumpster - vannesa had to do stuff with her old boss
      15:10
      Djinn - Martha is a cum dumpster - vannesa had to do stuff with her old boss
      Johannesgaming
      27.8K views
    • Djinn - Martha is a cum dumpster - vannesa had to do stuff with her old boss
      07:47
      Djinn - Martha is a cum dumpster - vannesa had to do stuff with her old boss
      Johannesgaming
      2.7K views
    • He Used to Be the Boss but Not Anymore
      08:12
      He Used to Be the Boss but Not Anymore
      Pure Ts
      470.9K views
    • Auditioning for the drag show
      08:12
      Auditioning for the drag show
      Pure Ts
      65.3K views
    • The End of a Work Week
      06:12
      The End of a Work Week
      Pure Ts
      17K views
    • Boss Fucks Petite Trans Maid
      08:35
      Boss Fucks Petite Trans Maid
      Bailey Wilde
      391.6K views
    • The End of a Work Week
      06:12
      The End of a Work Week
      Pure Ts
      8.9K views
    • Slutty Employee Interrupts Boss’s Video Call By Sucking Her Dick TRAILER
      02:35
      Slutty Employee Interrupts Boss’s Video Call By Sucking Her Dick TRAILER
      Futanari XXX
      758.6K views
    • Prison of Sissy 3 the Pr Manager Fucked
      11:10
      Prison of Sissy 3 the Pr Manager Fucked
      Johannesgaming
      18.7K views
    • Trans Maid Kaela Luna Wants to Be Used by Her New Boss
      08:12
      Trans Maid Kaela Luna Wants to Be Used by Her New Boss
      Trans Roommates
      33.1K views
    • Your Boss Is a Homewrecker
      08:09
      Your Boss Is a Homewrecker
      WetZemu
      47.1K views
    • Work Underling Becomes Secret Sissy Fucktoy
      08:12
      Work Underling Becomes Secret Sissy Fucktoy
      Pure Ts
      8.2K views
    • Femboy Boss Fucks Petite Trans Maid
      08:34
      Femboy Boss Fucks Petite Trans Maid
      Bailey Wilde
      27.7K views
    • Crossdressing Boss Fucked Petite Trans Maid Worker
      08:34
      Crossdressing Boss Fucked Petite Trans Maid Worker
      Bailey Wilde
      57.8K views
    • Sissy Maid Worships Boss Feet and Pegged
      06:08
      Sissy Maid Worships Boss Feet and Pegged
      Bailey Wilde
      24.9K views
    • Beautiful Trans Bareback Anal with Her New Boss
      08:12
      Beautiful Trans Bareback Anal with Her New Boss
      Trans Roommates
      55.5K views
    • Busty trans Milf Aphrodite Adams gets bareback from boss
      08:12
      Busty trans Milf Aphrodite Adams gets bareback from boss
      Trans Roommates
      25.1K views
    • Tuck It Upp Underwear Show off
      04:11
      Tuck It Upp Underwear Show off
      MerlinMystique
      1.5K views
    • You Trans MILF Boss Wants to Fuck You in her Office
      01:31
      You Trans MILF Boss Wants to Fuck You in her Office
      Lucy Hart
      99K views
    • Trans Maid Pleasures Her New Boss
      08:12
      Trans Maid Pleasures Her New Boss
      Trans Roommates
      93.8K views
    • While the boss is away secretary entertains clients
      04:36
      While the boss is away secretary entertains clients
      Sarahsatinslut
      12.5K views
    • VERY HOT Sissy Maid Fucked by Boss
      03:07
      VERY HOT Sissy Maid Fucked by Boss
      Bailey Wilde
      48.4K views
    • Tattooed latina beauty strips and strokes at the office
      07:40
      Tattooed latina beauty strips and strokes at the office
      Wonder Shemale
      2K views
    • Leopard print, Satin & tasty CUM
      04:43
      Leopard print, Satin & tasty CUM
      Sarahsatinslut
      37.7K views
    • Patriotic trans Kourtney Steel wants a bareback lesson
      08:12
      Patriotic trans Kourtney Steel wants a bareback lesson
      Trans Roommates
      31.3K views
    • Sissy Maid Fucked by Boss
      01:22
      Sissy Maid Fucked by Boss
      Bailey Wilde
      6.7K views
    • While the Boss Is Away the Secretary Will Play
      08:12
      While the Boss Is Away the Secretary Will Play
      Ficd
      17.7K views
    • My boss banned me from wearing transparent dresses in the office.
      05:09
      My boss banned me from wearing transparent dresses in the office.
      cd_aysemmm
      just added
    • Italian Tranny Boss Manhandles Her Personal Male Sex Slave - Shemale n Trans
      08:12
      Italian Tranny Boss Manhandles Her Personal Male Sex Slave - Shemale n Trans
      Trans n Shemale
      4.7K views
    • Trans Boss Fucks Petite Trans Maid
      07:08
      Trans Boss Fucks Petite Trans Maid
      Bailey Wilde
      28.1K views
    • Slut Secretary Sarah Enjoys Her Toy
      08:03
      Slut Secretary Sarah Enjoys Her Toy
      Sarahsatinslut
      7.5K views
    • Slut trans maid Aphrodite Adams served by her boss bareback
      08:12
      Slut trans maid Aphrodite Adams served by her boss bareback
      Trans Roommates
      13.2K views
    • Slut Office Boss
      08:12
      Slut Office Boss
      Ficd
      9.8K views
    • I secretly sucked my boss's dick during the meeting
      05:08
      I secretly sucked my boss's dick during the meeting
      cd_aysemmm
      3.1K views
    • Boss Hogg XXXL Love to bounce X
      02:43
      Boss Hogg XXXL Love to bounce X
      4.2K views
    • My boss realized I'm not a girl
      05:08
      My boss realized I'm not a girl
      cd_aysemmm
      3K views
    • Sissification and Strapon Fucked by Boss to Get Maid Job
      01:36
      Sissification and Strapon Fucked by Boss to Get Maid Job
      Bailey Wilde
      4.8K views
    • Trans girl manages to provoke with her beautiful feet
      06:47
      Trans girl manages to provoke with her beautiful feet
      Drakefox
      1.5K views
    • Young Cuban Trans Goddess Gets Railed by Older Man
      05:21
      Young Cuban Trans Goddess Gets Railed by Older Man
      Bigdanny10
      224.5K views
    • The 18 Years Old Asian Thai Ladyboy Yuri Like Deep Anal Sex
      07:14
      The 18 Years Old Asian Thai Ladyboy Yuri Like Deep Anal Sex
      Ladyboys and shemales
      124.8K views
    • Passionate Older Chub & Gorgeous Ladyboy Suck Each Other Dry and Swallow Every Drop
      21:49
      Passionate Older Chub & Gorgeous Ladyboy Suck Each Other Dry and Swallow Every Drop
      HeShexxx
      31.9K views
    • Stepdaddy fuck trans 20yo stepdaughter
      08:53
      Stepdaddy fuck trans 20yo stepdaughter
      Crystal Phoenix
      366.6K views
    • 19 years old trans has her first threesome
      10:06
      19 years old trans has her first threesome
      Saranji
      562.5K views
    • She Is Really Into Older Men
      08:12
      She Is Really Into Older Men
      Pure Ts
      325K views
    • Teen Sissy Already Knows Her Place
      08:12
      Teen Sissy Already Knows Her Place
      Pure Ts
      72.1K views
    • Big stepbrother finds me alone in the room and makes me his whore
      08:46
      Big stepbrother finds me alone in the room and makes me his whore
      Crystal Phoenix
      278.5K views
    • Epic Outdoors Blow Job
      04:52
      Epic Outdoors Blow Job
      SA247365
      24.2K views
    Next page
    1. 1
    2. 2
    3. 3

    Searches Related to Old Boss

    • Grandpa Shares Granny
    • Old Man Facial
    • Latin Old Man
    • Indonesian Granny
    • 50 Plus Mature
    • Saudi Arabia Xnxx
    • Vintage
    • Grandpa Loves Thai
    • Grandpas at Massage
    • Super Old Granny
    • Grandma Sucks
    • Step Mom
    • Mommy
    • Nigerian Granny
    • Old Fat Grandpa
    • Old Women Big Boobs
    • Older Housewife
    • Transgender Mom
    • Big Ass Black Brazilian
    • Black Boss
    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