Porn Porn Transgender • US
  • Live Sex
  • Premium Premium Videos
  • Categories
  • Pornstars
  • Channels
  • photos
GOAL! World Cup Mega Sale ⚽🏆 Play Hard. Save Hard

Boss Lesson Porn Videos

824 Results

Free Videos
Short Videos
Premium Videos
Photos
HD
Full HD
4K
VR
Best Videos
By clicking the content you will also see an ad. AD
  • Patriotic trans Kourtney Steel wants a bareback lesson
    08:12
    Patriotic trans Kourtney Steel wants a bareback lesson
    Trans Roommates
    34.3K views
  • wow3
    45:59
    wow3
    sss735
    365.4K views
  • Trans Babysitter Gets taught a lesson by HOT milf
    08:21
    Trans Babysitter Gets taught a lesson by HOT milf
    Erica Cherry
    1.7M views
  • Blow that Bitch.
    02:36
    Blow that Bitch.
    Ronnie142
    594.1K views
  • naughty college girl gets taught a hard lesson
    08:12
    naughty college girl gets taught a hard lesson
    Pure Ts
    173.7K views
  • ioioioioi
    08:39
    ioioioioi
    K Kondoo
    902.3K views
  • Threesome Lesson: Big-assed Trans Turned the School Into an Elite Orgy!
    08:12
    Threesome Lesson: Big-assed Trans Turned the School Into an Elite Orgy!
    LukasZaad
    61.6K views
  • TRANS ANGELS - Seductive Boss Chanel Santini Gives Her Employee Tony A Fuck Lesson For Being Naughty
    39:33
    TRANS ANGELS - Seductive Boss Chanel Santini Gives Her Employee Tony A Fuck Lesson For Being Naughty
    Trans Angels
    1.2M views
  • Transangels - a Lesson in D Major - Kate England, Jessica Foxx
    06:12
    Transangels - a Lesson in D Major - Kate England, Jessica Foxx
    Trans Angels
    297.1K views
  • Cop's doom
    17:43
    Cop's doom
    J JLash
    249.3K views
  • Billiards lessons for the explosive Raphaella Ferrari
    31:49
    Billiards lessons for the explosive Raphaella Ferrari
    Pinko TGirls
    479.2K views
  • CD TRAP SISSY EDUCATION TRAINING 101
    01:27:33
    CD TRAP SISSY EDUCATION TRAINING 101
    AZNSWAGDADDY
    1.1M views
  • Blake Lovely's Lingerie Trans Anal Lesson with Mia Macana
    08:12
    Blake Lovely's Lingerie Trans Anal Lesson with Mia Macana
    Trans Roommates
    43.5K views
  • good bitch
    02:37
    good bitch
    281K views
  • I Caught a Trans Exposing Herself and Taught Her a Lesson
    02:35
    I Caught a Trans Exposing Herself and Taught Her a Lesson
    WesleyBull
    74.4K views
  • feminisation training
    09:58
    feminisation training
    I IndirectInitiator50
    774K views
  • Busty Jade Nyxxx Gives A Creampie Lesson
    13:53
    Busty Jade Nyxxx Gives A Creampie Lesson
    Trans Roommates
    777.1K views
  • Teaching a Fag his place
    13:47
    Teaching a Fag his place
    Kimberhaven
    949.1K views
  • TRANSFIXED - Korra Del Rio Gets Fucked In Front Of Her Cuckold Husband To Teach Him A Lesson
    12:58
    TRANSFIXED - Korra Del Rio Gets Fucked In Front Of Her Cuckold Husband To Teach Him A Lesson
    Transfixed
    566K views
  • Sissy #3: Feminize Yourself
    16:07
    Sissy #3: Feminize Yourself
    softboixladyathena
    781.6K views
  • training
    07:56
    training
    chastitygurl
    158.4K views
  • Relevant Short videos

    Patriotic trans Kourtney Steel wants a bareback lesson
    Patriotic trans Kourtney Steel wants a bareback lesson
    Trans Roommates
    2.7K views
    Sophie Ladder Teaches the Horny Maid a Lesson
    Sophie Ladder Teaches the Horny Maid a Lesson
    Trans Roommates
    5.6K views
    Blonde trans Lianna Lawson taught lesson by roommate
    Blonde trans Lianna Lawson taught lesson by roommate
    Trans Roommates
    5.1K views
    Strict Trans Teacher: Pissing & Deep Dildo Lesson
    Strict Trans Teacher: Pissing & Deep Dildo Lesson
    Medi Voi
    3.9K views
    Trans babe queen ivory teaches roommate bareback lesson
    Trans babe queen ivory teaches roommate bareback lesson
    Trans Roommates
    2.9K views
    Sexy Kelli Lox gives a lesson in jerking a guy off
    Sexy Kelli Lox gives a lesson in jerking a guy off
    Pure Ts
    3.4K views
  • Sissy #2: Becoming A Cock Slut
    15:35
    Sissy #2: Becoming A Cock Slut
    softboixladyathena
    1M views
  • TS got that good head
    02:56
    TS got that good head
    C CockADoodleDick69
    180.3K views
  • Sissifications (Animation)
    08:08
    Sissifications (Animation)
    parisgreen
    288.1K views
  • Sissification 1 (Animation)
    09:24
    Sissification 1 (Animation)
    parisgreen
    196K views
  • jefa y secretaria
    20:42
    jefa y secretaria
    f failos
    2.4M views
  • Sissy identity
    08:50
    Sissy identity
    S Scenedude
    1M views
  • You're a faggot
    05:50
    You're a faggot
    333.9K views
  • Sissy Brainwashing Training
    13:46
    Sissy Brainwashing Training
    s sguy263
    412K views
  • ts top mix
    42:12
    ts top mix
    654.5K views
  • girlcock brainwashing - sink even deeper
    17:10
    girlcock brainwashing - sink even deeper
    g gcslave1
    497.8K views
  • Sissyfication
    43:09
    Sissyfication
    merllin3
    1.4M views
  • Watch it often
    14:29
    Watch it often
    64.5K views
  • The exhibisionist
    01:37
    The exhibisionist
    avrix
    396.7K views
  • Sissy Study Session
    10:04
    Sissy Study Session
    pantycum666
    398.4K views
  • Shemale trainer
    13:03
    Shemale trainer
    dave1701a
    420.3K views
  • In the Bus
    12:46
    In the Bus
    NylonPetra
    1.9M views
  • Submission Sissy Trainer
    03:23
    Submission Sissy Trainer
    1.3M views
  • He Used to Be the Boss but Not Anymore
    08:12
    He Used to Be the Boss but Not Anymore
    Pure Ts
    639.3K views
  • Sissy #1: Accepting Your Destiny
    11:37
    Sissy #1: Accepting Your Destiny
    softboixladyathena
    572.6K views
  • sissy joi
    04:27
    sissy joi
    277.2K views
  • training
    07:28
    training
    chastitygurl
    165.2K views
  • Sissy bitch training
    04:02
    Sissy bitch training
    ita_sissywhore
    160.2K views
  • Magic Mask
    05:11
    Magic Mask
    Ed4u
    218K views
  • sissy training
    15:28
    sissy training
    sexobjekt
    446.7K views
  • you love men - lesson 44
    09:14
    you love men - lesson 44
    pipenpondle
    416.9K views
  • Boss' Ultimatum
    07:49
    Boss' Ultimatum
    Kink
    151.1K views
Next page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. ...
  8. 10
  9. ...
  10. 18
18
Categories
American
4K Porn
HD Videos
VR Porn
Shemale Fucks Guy
Big Cock
Shemale Fucks Shemale
Black
Amateur
Shemale Fucks Girl
Sissy
Ladyboy
Guy Fucks Shemale
Blowjob
Compilation
Big Black Cock
Cum In Mouth
Big Ass
Cumshot
Mature
Bareback
Creampie
Homemade
Masturbation
Anal
Domination
Teen
Asian
Solo
BBW
Vintage
Young
Transgender
Brazilian
Cartoon
Big Tits
Interracial
Mexican
Small Cock
Lingerie
Japanese
Threesome
Gangbang
Trans Woman
Trap
Thai
BDSM
Colombian
Public
Couple
MILF
Petite
Anal Masturbation
Dildo
Rough Sex
Cuckold
Pretty
Small Tits
Stockings
Outdoor
POV
Babysitter
Trans Man
Handjob
Group Sex
Hentai
Indian
Fetish
Futanari
English
Hardcore
Bondage
Nude
Massage
Ass Licking
Pissing
Chinese
SFW
All recommendations
Monetize your content
Become a creator
xHamster
  • About us
  • Blog
  • Creator's Blog
  • Advertising
  • xHamster Awards 2025
  • SEO Specialist Job
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