PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    WINTER MAGIC SALE ❄️☃️ Snowy discounts, hot deals!
    0

    Cuckold boss Porn Pics

    Free Videos
    Short videos
    Premium Videos
    Photos
    By clicking the content you will also see an ad. AD
    TGIRLS.XXX: Managing Expectations
    7

    TGIRLS.XXX: Managing Expectations

    Grooby_Girls
    Grooby_Girls
    1.5K views
    GROOBYGIRLS: Managing Livi
    7

    GROOBYGIRLS: Managing Livi

    Grooby_Girls
    Grooby_Girls
    4.7K views
    FEMOUT: The Band Manager
    7

    FEMOUT: The Band Manager

    Grooby_Girls
    Grooby_Girls
    5.8K views
    sissy in office cloths
    17

    sissy in office cloths

    KatkieLane212
    KatkieLane212
    6.5K views
    GROOBYGIRLS: Your Dream Boss
    7

    GROOBYGIRLS: Your Dream Boss

    Grooby_Girls
    Grooby_Girls
    8.6K views
    Please, sit, we'll help you out with that Baldur's Gate boss
    1

    Please, sit, we'll help you out with that Baldur's Gate boss

    AcrylicCloud
    AcrylicCloud
    3.1K views
    BLACKTGIRLS HARDCORE: Sassy is Da Boss
    9

    BLACKTGIRLS HARDCORE: Sassy is Da Boss

    Grooby_Girls
    Grooby_Girls
    7.9K views
    Slutty sissy secretary
    45

    Slutty sissy secretary

    Emma Huntcock
    Emma Huntcock
    12.4K views
    I am your girl boss
    24

    I am your girl boss

    Anna Rios
    Anna Rios
    64.7K views
    Boss pics
    10

    Boss pics

    Cassandra Lovit
    Cassandra Lovit
    51.3K views
    Boss or Secretary
    9

    Boss or Secretary

    Nikki_Licious
    Nikki_Licious
    29.5K views
    Boss wants to know why I'm so distracted at work lately
    12

    Boss wants to know why I'm so distracted at work lately

    Tasha Tarte
    Tasha Tarte
    58.8K views
    TGIRLS.XXX: Boss Bitch Training
    7

    TGIRLS.XXX: Boss Bitch Training

    Grooby_Girls
    Grooby_Girls
    10.3K views
    TGIRLS.XXX: Social Media Management
    7

    TGIRLS.XXX: Social Media Management

    Grooby_Girls
    Grooby_Girls
    3.7K views
    Boss Bitch
    5

    Boss Bitch

    TaffyCabrera95
    TaffyCabrera95
    19.1K views
    Red dress three
    42

    Red dress three

    R
    Roni Swallows
    6.1K views
    Sissy secret  in the office
    28

    Sissy secret in the office

    KatkieLane212
    KatkieLane212
    8.4K views
    nasty sissy (devil's lil gurl)
    8

    nasty sissy (devil's lil gurl)

    jessysky723
    jessysky723
    3.7K views
    Tiny Clitty Sissy Gurl
    5

    Tiny Clitty Sissy Gurl

    Michaela Pink
    Michaela Pink
    804 views
    Pumped sissyclit
    8

    Pumped sissyclit

    pervdev39
    pervdev39
    851 views
    Sissy
    23

    Sissy

    S
    SissyAmyy
    2.2K views
    Trinity CUMSLUT #trinitycumslut
    67

    Trinity CUMSLUT #trinitycumslut

    Maidsevice420
    Maidsevice420
    4.1K views
    Silky Silver Cum
    2

    Silky Silver Cum

    B
    Bstick100
    1.8K views
    Silky Silver Panty
    5

    Silky Silver Panty

    B
    Bstick100
    2.5K views
    Locked sissy
    4

    Locked sissy

    suckyoudry76
    suckyoudry76
    1.3K views
    Deepthroat practice
    23

    Deepthroat practice

    PorchaeTS
    PorchaeTS
    2.2K views
    Sissy crossdresser
    11

    Sissy crossdresser

    Daisysiss
    Daisysiss
    4.2K views
    I am a pathetic sissy cuckold
    2

    I am a pathetic sissy cuckold

    PrincessFifi
    PrincessFifi
    1.2K views
    Sissy Daniella Best of....
    36

    Sissy Daniella Best of....

    SissyDaniella
    SissyDaniella
    17.9K views
    Fiona and Mr Long May 2025
    29

    Fiona and Mr Long May 2025

    Fiona Fortune
    Fiona Fortune
    15K views
    June 2025
    7

    June 2025

    Jasmine904x
    Jasmine904x
    12.6K views
    Sissy Slave Lene
    2

    Sissy Slave Lene

    B
    Bekkslave
    3.4K views
    Sissy in rosa Unterwaesche
    6

    Sissy in rosa Unterwaesche

    Swissnylonsissy69
    Swissnylonsissy69
    4.7K views
    BLACK-TGIRLS: The Princess Arrives
    7

    BLACK-TGIRLS: The Princess Arrives

    Grooby_Girls
    Grooby_Girls
    4.2K views
    Homemade  cuck anal
    3

    Homemade cuck anal

    Uglycassanova27m
    Uglycassanova27m
    695 views
    Practice
    1

    Practice

    annaarang
    annaarang
    1.4K views
    Sissy cross dresser
    8

    Sissy cross dresser

    FumikoKatt
    FumikoKatt
    4.5K views
    Sissy cage
    1

    Sissy cage

    Sissyemmie69
    Sissyemmie69
    2K views
    Angewichst
    3

    Angewichst

    Srptzer2025
    Srptzer2025
    1.5K views
    I am Anal Queen
    1

    I am Anal Queen

    TSquennAna
    TSquennAna
    7.6K views
    Blue panties
    4

    Blue panties

    Aaaxoa
    Aaaxoa
    3.4K views
    Sissy Keuschheit
    3

    Sissy Keuschheit

    Sissy_Nadiene
    Sissy_Nadiene
    3K views
    ASIANTGIRL: Sugary Sweet Fun
    7

    ASIANTGIRL: Sugary Sweet Fun

    Grooby_Girls
    Grooby_Girls
    4.9K views
    GROOBYGIRLS: Going Nuts For Nuzzle
    7

    GROOBYGIRLS: Going Nuts For Nuzzle

    Grooby_Girls
    Grooby_Girls
    11.1K views
    Sissy Anna 2025
    3

    Sissy Anna 2025

    Sissy_Boy_Anna
    Sissy_Boy_Anna
    4.5K views
    White Sissy
    78

    White Sissy

    Nikki Snowbunny
    Nikki Snowbunny
    87.8K views
    Sophia Sissy Exposure 6
    23

    Sophia Sissy Exposure 6

    SophiaSissy69
    SophiaSissy69
    10.9K views
    Sophia Sissy Exposed 4
    13

    Sophia Sissy Exposed 4

    SophiaSissy69
    SophiaSissy69
    8K views
    Sophia Sissy Exposure 3
    23

    Sophia Sissy Exposure 3

    SophiaSissy69
    SophiaSissy69
    8.1K views
    Latest chastity cages
    9

    Latest chastity cages

    PorchaeTS
    PorchaeTS
    10.2K views
    sissy
    4

    sissy

    your-sissyslut
    your-sissyslut
    5K views
    FEMOUT.XXX: Xiomara D'Amore Debuts
    7

    FEMOUT.XXX: Xiomara D'Amore Debuts

    Grooby_Girls
    Grooby_Girls
    6.7K views
    Tonight
    16

    Tonight

    Sandy S Banks
    Sandy S Banks
    3.5K views
    Sissy maid
    4

    Sissy maid

    S
    sissyfaggotIt
    2.4K views
    Sissy Breast
    4

    Sissy Breast

    DWTNico
    DWTNico
    3.4K views
    thats me
    2

    thats me

    MGSissy
    MGSissy
    3.6K views
    Natali MiX
    20

    Natali MiX

    Natalicrossdresser91
    Natalicrossdresser91
    11K views
    FRANKS-TGIRLWORLD: Sassy Poy!
    7

    FRANKS-TGIRLWORLD: Sassy Poy!

    Grooby_Girls
    Grooby_Girls
    13.2K views
    Sissy4U
    5

    Sissy4U

    UrSissySlaveXXX
    UrSissySlaveXXX
    6.6K views
    Becoming a feminized sissy
    9

    Becoming a feminized sissy

    Jason Coxe
    Jason Coxe
    7K views
    Next page
    1. 1
    2. 2

    Categories

    American
    Ladyboy
    Amateur
    Bareback
    BDSM
    Big Ass
    Big Cock
    Big Tits
    Blowjob
    Creampie
    Gangbang
    Guy Fucks Shemale
    Interracial
    Latex
    Latina
    Lingerie
    Masturbation
    Outdoor
    POV
    Sex Toy
    Shemale Fucks Girl
    Small Tits
    Stockings
    Vintage
    Black
    Shemale Fucks Guy
    Mature
    Anal
    Ass
    Asian
    Cum
    Beautiful
    BBW
    Asshole
    Monster Cock
    Fat
    Blonde
    Hardcore
    Fetish
    Bikini
    Handjob
    Threesome
    Group Sex
    Tranny
    Brazilian
    Thai
    Cumshot
    69
    Babe
    Brutal Sex
    Close-up
    Nipples
    Old and Young
    Panties
    Striptease
    Cook
    All categories
    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