PornPorn Transgender • US
    Sign up for free
    Videos
    • Best Videos
    • Short Videos
    • Watch History
    • American
    • Amateur
    • Shemale Fucks Guy
    • Shemale Fucks Girl
    • Big Cock
    • All categories
    Live Sex
    Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • All categories
    Pornstars
    • Pornstars
    • By Countries
    • xHamster Creators
    Creators
    • Top Creators
    • Top Creator Videos
    • Awards 2025
    • All xHamster Creators
    • By Countries
    • Become a Creator
    Channels
    Photos
    • Ladyboy
    • Tranny
    • Big Cock
    • Thai
    • Blowjob
    • All categories
    Faphouse
    Premium Videos
    Dating
    Subscriptions
    • Upload
    WINTER MAGIC SALE ❄️☃️ Snowy discounts, hot deals!
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • Shemale Fucks Girl
    • Sissy
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Cum In Mouth
    • Big Black Cock
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Milf Boss Anal Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Shemale MILF boss gets fucked and then fucks male employee
    07:44
    Shemale MILF boss gets fucked and then fucks male employee
    70.9K views
    He Used to Be the Boss but Not Anymore
    08:12
    He Used to Be the Boss but Not Anymore
    Pure Ts
    474.3K views
    I fuck my boss's pussy
    08:45
    I fuck my boss's pussy
    FLACO
    1M views
    GenderX - Guy Fucked By Trans Boss To Save His Job
    11:31
    GenderX - Guy Fucked By Trans Boss To Save His Job
    GenderX
    703K views
    Exposed Crossdresser has to satisfy the Office Manager
    03:10
    Exposed Crossdresser has to satisfy the Office Manager
    321.1K views
    Imagine, How Does Separated Wife, Manages Masterbation
    02:29
    Imagine, How Does Separated Wife, Manages Masterbation
    Apple00001
    178.6K views
    Rigid3d D3d Buttercoat Intense Office Threesome: Hot Slut Fucked by Two Huge Cocks, Deep Throat & Anal with My Bosses
    02:41
    Rigid3d D3d Buttercoat Intense Office Threesome: Hot Slut Fucked by Two Huge Cocks, Deep Throat & Anal with My Bosses
    taptapKO
    180.6K views
    The Boss Bathroom
    17:57
    The Boss Bathroom
    230.3K views
    Blowing the gigantic cock of the boss to get the job - Blowjob Interview! - HQ 3D Animation
    05:35
    Blowing the gigantic cock of the boss to get the job - Blowjob Interview! - HQ 3D Animation
    T TheHentaiGuy94
    136.3K views
    Beautiful Sasha De Sade Get Used by Her Boss Actorfab
    06:17
    Beautiful Sasha De Sade Get Used by Her Boss Actorfab
    ActorFab
    52.3K views
    DesireSFM - FUTANARI MILF Fucks Her Boss Hardcore Futa Sex - SO MUCH CUM 3D Futa Hentai
    18:20
    DesireSFM - FUTANARI MILF Fucks Her Boss Hardcore Futa Sex - SO MUCH CUM 3D Futa Hentai
    NaughtyGameplays
    2.7M views
    boss fucked two women in room
    03:42
    boss fucked two women in room
    821.3K views
    Petershentai Naughty Employee Slut Fucked by Her Boss Doggy Style Swallowing a Huge Cock for a Promotion
    05:27
    Petershentai Naughty Employee Slut Fucked by Her Boss Doggy Style Swallowing a Huge Cock for a Promotion
    taptapKO
    68.7K views
    ASMR with EngSub. Bossy master in black nylons gives a sticky footjob and humiliates. Now it's your turn to dominate her back.
    12:53
    ASMR with EngSub. Bossy master in black nylons gives a sticky footjob and humiliates. Now it's your turn to dominate her back.
    Harinni
    10.7K views
    FUTANARI MILF Fucks Herself AND Futa Boss Assfucks HARD on a Plane - SO MUCH CUM - Amy's Big Wish S01-4-5
    15:05
    FUTANARI MILF Fucks Herself AND Futa Boss Assfucks HARD on a Plane - SO MUCH CUM - Amy's Big Wish S01-4-5
    AgentRedGirl
    80K views
    Office Fuck Up Gets Lucky With Shemale Boss Lady Janice Renee
    11:39
    Office Fuck Up Gets Lucky With Shemale Boss Lady Janice Renee
    Janice Renee
    104.7K 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
    Mature bubble ass hotel manager gets his first ass fuck by a Black trans Dick - WickedWhims
    05:34
    Mature bubble ass hotel manager gets his first ass fuck by a Black trans Dick - WickedWhims
    SimsLust
    60.1K views
    Meeting Mating
    08:00
    Meeting Mating
    TS Virtual Lovers
    5.8K views
    Kentucky fried black dick
    06:40
    Kentucky fried black dick
    Sissy Michelle MTF
    20K views
    A Hardcore Mouth & Anal Sex Drill by Hostel Manager Lola
    09:09
    A Hardcore Mouth & Anal Sex Drill by Hostel Manager Lola
    Asura
    12.4K views
    I fuck my boss's pussy in the confrontation
    09:47
    I fuck my boss's pussy in the confrontation
    A ANDREINA
    11.7K views
    Horny Shemale Boss pound My Asshole With Her huge Cock
    10:24
    Horny Shemale Boss pound My Asshole With Her huge Cock
    future money man
    4.1K 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
    Raven-haired American shemale gives bald boss a dick
    06:15
    Raven-haired American shemale gives bald boss a dick
    544.7K views
    blonde big ass shemale get anal fuck
    25:28
    blonde big ass shemale get anal fuck
    EroCom
    24.1K views
    Boss gives his big booty trans secretary his long thick long BBC
    05:02
    Boss gives his big booty trans secretary his long thick long BBC
    Enter Tranz
    106K views
    BBC boss spanks his BIG ASS trans secretary.
    05:24
    BBC boss spanks his BIG ASS trans secretary.
    Enter Tranz
    89.2K views
    patty crossdresser I'm your bitch boss
    15:54
    patty crossdresser I'm your bitch boss
    Patty crossdresser
    6K views
    Boss fucks his cd slave on the stairs
    15:48
    Boss fucks his cd slave on the stairs
    53.9K views
    I'm Stroking my Boss's Dick under the table
    03:07
    I'm Stroking my Boss's Dick under the table
    cd_aysemmm
    14.2K views
    The Creampie Clean Up Duty by Manager Selena - Sky Resort
    09:33
    The Creampie Clean Up Duty by Manager Selena - Sky Resort
    Asura
    7.2K views
    Boss is Testing My Limits : The Thickening
    06:38
    Boss is Testing My Limits : The Thickening
    Asura
    6.1K views
    Kellystar518 - Return of Devil Girl
    08:45
    Kellystar518 - Return of Devil Girl
    Kellystar518
    20.4K views
    PI3DA rides Mr. Hankey’s Boss Hogg-XL 100 times
    01:38
    PI3DA rides Mr. Hankey’s Boss Hogg-XL 100 times
    pi3da
    just added
    Problems at the office sometime need to please the boss
    16:06
    Problems at the office sometime need to please the boss
    Nicole Montero
    138.6K views
    Big dick girl managed to fuck a boy in the little car
    00:41
    Big dick girl managed to fuck a boy in the little car
    35.7K views
    Chick with dick pounded by her boss
    22:26
    Chick with dick pounded by her boss
    Shemales Tales
    4.2K views
    The Boss Plug Is as Girthy as Big Daddy
    07:56
    The Boss Plug Is as Girthy as Big Daddy
    KNKY Bee
    1.1K views
    Boss Hogg XXXL Love to bounce X
    02:43
    Boss Hogg XXXL Love to bounce X
    4.2K views
    huge tiT girl latin milf T girl boss Foxxy sucks n anal
    04:47
    huge tiT girl latin milf T girl boss Foxxy sucks n anal
    8.5K views
    Almost Halloween
    01:48
    Almost Halloween
    Karma Rainbow Smith D
    6.2K views
    PI3DA rides Mr.Hankey's Boss Hogg-XL 50 times
    01:12
    PI3DA rides Mr.Hankey's Boss Hogg-XL 50 times
    pi3da
    just added
    Transsexual maid and her mature boss have a steamy fuck fest
    09:30
    Transsexual maid and her mature boss have a steamy fuck fest
    Trans Erotica
    50K views
    Appoinment with boss and done with sex and blowjob
    02:17
    Appoinment with boss and done with sex and blowjob
    Varsha Singh
    2K views
    Slut anal nympho maid waitiing for saudi boss and his friend
    01:45
    Slut anal nympho maid waitiing for saudi boss and his friend
    3.3K views
    Sexy Slut Maid waiting for new Saudi Boss for Anal Pleasure
    01:45
    Sexy Slut Maid waiting for new Saudi Boss for Anal Pleasure
    3.8K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    xHamster

    • Press
    • 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

    Start making money with us

    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    Monetize your content
    Become a creator
    © 2007 - 2026, xHamster.com
    Mobile 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