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

    Boss Assistant Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Boss
    Trans Boss Fucks Her Assistant Good
    Shemale Boss
    Indian Boss
    Trans Boss
    Ts Boss
    Ladyboy Boss
    Office Boss
    Sucking Boss off
    Transgender Boss Porn
    Shemale Boss Office
    Boss Fucks Secretary
    Sassy the Boss
    Shemale Fucks Her Assistant
    3D Time Shemale Boss
    Sassy The Boss Leaked
    Transgender Boss Punishes Employee
    Indian Boss Fucked Hot Shemale
    Crossdresser Fucking Boss in Hotel Room
    My Boss Fucks My Wife
    Best Videos
    By clicking the content you will also see an ad. AD
    A BBC Boss, BBC Friend, BBC footballer, and a BBC homie pound wet trans asshole
    23:02
    A BBC Boss, BBC Friend, BBC footballer, and a BBC homie pound wet trans asshole
    Enter Tranz
    69.7K views
    Bigg Boss Tamil - Season 2 - DAY 12
    01:04:04
    Bigg Boss Tamil - Season 2 - DAY 12
    442.3K views
    OOPSIE - Security Kasey Kei Caught Boss Izzy Wilde Fucking New Hire In Elevator & Wanna Join Them
    12:31
    OOPSIE - Security Kasey Kei Caught Boss Izzy Wilde Fucking New Hire In Elevator & Wanna Join Them
    AdultTime
    494.4K views
    Femboy Boss Fucks Petite Trans Maid
    08:34
    Femboy Boss Fucks Petite Trans Maid
    Bailey Wilde
    27.7K views
    Threesome With Trans Nurse and Her MILF Boss - LeWood
    12:06
    Threesome With Trans Nurse and Her MILF Boss - LeWood
    EvilAngelOfficial
    1.5M views
    Sonechka tells how she managed to become a sissy whore. You just need to cum in your mouth everyday
    01:51
    Sonechka tells how she managed to become a sissy whore. You just need to cum in your mouth everyday
    Sonechka25
    129.1K views
    Maid Shemale Giovanna Garbi serving the boss
    00:41
    Maid Shemale Giovanna Garbi serving the boss
    112.7K views
    Beauty Bitch Cums for Her Boss
    08:12
    Beauty Bitch Cums for Her Boss
    ActorFab
    2K views
    Corporate Manager Natalie Mars Fucked In The Office
    10:53
    Corporate Manager Natalie Mars Fucked In The Office
    GenderX
    161.9K views
    TGIRLS XXX - Managing Expectations With Lola Morena
    03:12
    TGIRLS XXX - Managing Expectations With Lola Morena
    Tgirls
    1K views
    BLACKTGIRLS HARDCORE: Sassy is Da Boss
    03:11
    BLACKTGIRLS HARDCORE: Sassy is Da Boss
    Black Tgirls
    41.6K views
    Crossdressing Boss Fucked Petite Trans Maid Worker
    08:34
    Crossdressing Boss Fucked Petite Trans Maid Worker
    Bailey Wilde
    57.8K views
    While I'm cleaning I seduce my employer so that he fucks my small and tight ass
    22:22
    While I'm cleaning I seduce my employer so that he fucks my small and tight ass
    yesid
    86.4K 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
    Smoking Hot Latina Trans Boss Dicked Down By Hunk BBC
    12:52
    Smoking Hot Latina Trans Boss Dicked Down By Hunk BBC
    GenderX
    89.9K views
    GenderX - Big Dick Employer Fucks & Sucks His Trans Maid
    12:26
    GenderX - Big Dick Employer Fucks & Sucks His Trans Maid
    GenderX
    151.3K views
    Sissy Maid Worships Boss Feet and Pegged
    06:08
    Sissy Maid Worships Boss Feet and Pegged
    Bailey Wilde
    24.9K views
    Boss' Ultimatum
    07:49
    Boss' Ultimatum
    Kink
    142K views
    GROOBYGIRLS - Livi Doll Fucked By Her Socmed Manager
    03:12
    GROOBYGIRLS - Livi Doll Fucked By Her Socmed Manager
    Grooby Girls
    3.4K views
    GenderX - Boss TS Foxxy Expects More From Her Employee
    10:21
    GenderX - Boss TS Foxxy Expects More From Her Employee
    GenderX
    103.2K views
    Trans Maid Emma Ink Fucks Her Married Boss's Virgin Ass
    10:47
    Trans Maid Emma Ink Fucks Her Married Boss's Virgin Ass
    EmmaInkTrans
    40.6K views
    My Busty Fit tranny Boss owned my mouth - WickedWhims
    15:28
    My Busty Fit tranny Boss owned my mouth - WickedWhims
    SimsLust
    126.3K views
    Cute little asian maid  tranny fucks the bosses nice cock
    23:55
    Cute little asian maid tranny fucks the bosses nice cock
    1M views
    BIG BLACK BOSS SHEMALE
    00:31
    BIG BLACK BOSS SHEMALE
    373.6K views
    Transvestite Employee Ate the Boss's Ass
    06:12
    Transvestite Employee Ate the Boss's Ass
    Avantajadas
    4K 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
    Hot Shemale Franshesca Fucking her Boss s Ass on Webcam
    07:17
    Hot Shemale Franshesca Fucking her Boss s Ass on Webcam
    57.5K views
    I fuck my boss's pussy in the confrontation
    09:47
    I fuck my boss's pussy in the confrontation
    A ANDREINA
    12.7K 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
    CUSTOMER SERVICE - Huge Tits Futanari Babe Creampies Boss With Her Big Cock To Save Her Employees
    04:11
    CUSTOMER SERVICE - Huge Tits Futanari Babe Creampies Boss With Her Big Cock To Save Her Employees
    AdultTime
    25.5K views
    Tuck It Upp Underwear Show off
    04:11
    Tuck It Upp Underwear Show off
    MerlinMystique
    1.5K views
    Hannah Seduces Me into Funtari Boss Olivia
    09:26
    Hannah Seduces Me into Funtari Boss Olivia
    Asura
    32.2K views
    I fuck my boss's pussy when I left work
    08:32
    I fuck my boss's pussy when I left work
    brenda paola rojas villasmil
    20.9K views
    Shemales double team the boss at work
    08:12
    Shemales double team the boss at work
    Wonder Shemale
    3.5K views
    Shemale Trans Ellyn in Guided Punette with Enjoyed Gust
    09:06
    Shemale Trans Ellyn in Guided Punette with Enjoyed Gust
    Shemale Ellyn Trans
    25.4K views
    Submit To Your Boss!
    07:05
    Submit To Your Boss!
    Cassandra Lovit
    33.6K 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
    Demanding Job Interview
    08:12
    Demanding Job Interview
    Anna Rios
    24.2K views
    Kinky Manager Spitroasted By BIG COCKED Trans Hotties
    11:10
    Kinky Manager Spitroasted By BIG COCKED Trans Hotties
    GenderX
    140.2K views
    Horny shemale fucks her boss to keep her job
    07:37
    Horny shemale fucks her boss to keep her job
    Enter Tranz
    52K 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
    Teighjiana boss tgirl fantasy
    04:40
    Teighjiana boss tgirl fantasy
    Shemale Strokers
    931 views
    Small tits shemale maid Pixi Lust anal bareback by her boss
    06:10
    Small tits shemale maid Pixi Lust anal bareback by her boss
    GenderX
    110.2K views
    Sweet maid Natalie Mars loves tasting the cum of her boss
    09:42
    Sweet maid Natalie Mars loves tasting the cum of her boss
    Trans Erotica
    389.6K views
    Boss Excella
    03:46
    Boss Excella
    TiffanyWarmer
    7K views
    Trans Maid Pleasures Her New Boss
    08:12
    Trans Maid Pleasures Her New Boss
    Trans Roommates
    93.8K views
    • Back
    • 1
    • ...
    • 5
    • 6
    • 7
    • 8
    • 9
    • ...
    • 37
    • 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