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

    Sissy Lessons Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy Punishment
    Bbw Sissy
    Ebony Sissy
    Sissy Used
    Fat Sissy
    Sissy Dreams
    Caged Sissies
    Ai Sissy
    Arab Sissy
    Sissy Crying
    Sissy Bitch
    Sissy Milking
    Sissy Hentai
    Sissy Caught
    Sissy Rough
    Sissy CEI
    Sissy Hardcore
    Sissy Handjob
    Sissy CD
    Sissy Instructions
    Best Videos
    By clicking the content you will also see an ad. AD
    Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
    01:17
    Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
    Allmylinks
    106.4K views
    Trans Teacher Gets Taught Lesson By Rebel Student
    11:09
    Trans Teacher Gets Taught Lesson By Rebel Student
    hothotfilms
    579 views
    I finally let my stepsis fuck my trans pussy
    05:30
    I finally let my stepsis fuck my trans pussy
    CutePinkUnicorn
    614.3K views
    Trans Teacher Gets Taught Lesson By Rebel Student
    11:42
    Trans Teacher Gets Taught Lesson By Rebel Student
    hothotfilms
    13.4K views
    Lily DeMure Blowjob & Doggy
    11:54
    Lily DeMure Blowjob & Doggy
    1.6M views
    Futa anal lesson for the teacher in a 3d animation
    02:03
    Futa anal lesson for the teacher in a 3d animation
    Affect3DStore
    9.3K views
    Sissies Guide for Loving Anal
    05:04
    Sissies Guide for Loving Anal
    184.9K views
    VRB TRANS Practice lesson with skinny ballerina VR Porn
    02:14
    VRB TRANS Practice lesson with skinny ballerina VR Porn
    VRbtrans
    25.8K views
    Skyrim - Amorous Adventures: Ysolda's Tough Lesson
    26:39
    Skyrim - Amorous Adventures: Ysolda's Tough Lesson
    16.6K views
    VRBTrans Private Playing Balls Lesson
    06:07
    VRBTrans Private Playing Balls Lesson
    VRbtrans
    59.2K views
    Shemale Lena Kelly Gives Handjob Lesson
    06:51
    Shemale Lena Kelly Gives Handjob Lesson
    Big Booty TGIRLS
    54.1K views
    Dressage lesson
    10:56
    Dressage lesson
    NikkyTrav
    40K views
    Patriotic Trans Kourtney Steel Wants A Bareback Lesson
    05:08
    Patriotic Trans Kourtney Steel Wants A Bareback Lesson
    hothotfilms
    155.7K views
    Mirella Bristol's trans lessons
    43:43
    Mirella Bristol's trans lessons
    Pinko TGirls
    126.9K views
    Trans Teacher Gets Taught Lesson by Rebel Student
    08:09
    Trans Teacher Gets Taught Lesson by Rebel Student
    Trans Roommates
    6.4K views
    Dream Tranny - Tgirls Teaching Men Good Lessons Compilation
    08:03
    Dream Tranny - Tgirls Teaching Men Good Lessons Compilation
    Dream Tranny
    20.5K views
    anal lessons
    02:15
    anal lessons
    Big Dick Bitch
    293.8K views
    Larissa Albuquerque gets fucked bareback after a billiard lesson
    26:43
    Larissa Albuquerque gets fucked bareback after a billiard lesson
    Pinko TGirls
    9.1K views
    VRB TRANS Private Cam Sex Lesson VR Porn
    01:37
    VRB TRANS Private Cam Sex Lesson VR Porn
    VRbtrans
    18K views
    Cock Sucking Lesson Part 3.
    06:33
    Cock Sucking Lesson Part 3.
    61.1K views
    Adriana Rodrigues fucks a petite girl's mouth Oral Lesson 1
    01:25
    Adriana Rodrigues fucks a petite girl's mouth Oral Lesson 1
    48.5K views
    Cock SUCKING lesson 2 of 5
    11:01
    Cock SUCKING lesson 2 of 5
    49K views
    Dominant TS Nurse Barbara Perez Teaches Her Patient a Hard Lesson
    08:04
    Dominant TS Nurse Barbara Perez Teaches Her Patient a Hard Lesson
    Dream Tranny
    15.2K views
    Prequel fisting lesson
    14:11
    Prequel fisting lesson
    NikkyTrav
    11.9K views
    Trans Nurse Barbara Perez Teaches His Ass a Lesson
    15:10
    Trans Nurse Barbara Perez Teaches His Ass a Lesson
    Dream Tranny
    10.5K views
    VRB TRANS Piano Lesson With Silicone Dildo VR Porn
    02:01
    VRB TRANS Piano Lesson With Silicone Dildo VR Porn
    VRbtrans
    14.1K views
    I was helping my stepson with his lessons. I don't know why we did something like this. I'm so sorry.
    05:07
    I was helping my stepson with his lessons. I don't know why we did something like this. I'm so sorry.
    cd_aysemmm
    3.7K views
    How to clean your glasses (lesson 1)
    01:56
    How to clean your glasses (lesson 1)
    63.8K views
    Billiards lessons with Raphaella Ferrari! by Andrea Nobili
    00:46
    Billiards lessons with Raphaella Ferrari! by Andrea Nobili
    Pinko TGirls
    140.5K views
    notorious daddy gives a lesson
    02:15
    notorious daddy gives a lesson
    26K views
    The Piano Lesson!
    04:45
    The Piano Lesson!
    9K views
    Monika to takes lessons rides  in big  dildo.
    02:55
    Monika to takes lessons rides in big dildo.
    3.5K views
    My teacher wife helps me with my lessons.
    05:07
    My teacher wife helps me with my lessons.
    cd_aysemmm
    6.1K views
    Sub Jackie's Lesson 3
    39:17
    Sub Jackie's Lesson 3
    34.2K views
    a lesson on deep throating
    04:28
    a lesson on deep throating
    19.7K views
    Swimming Lesson for Tgirl Gabrielly Ferraz Turns Into a Bareback Flip Fuck
    12:05
    Swimming Lesson for Tgirl Gabrielly Ferraz Turns Into a Bareback Flip Fuck
    Dream Tranny
    2.5K views
    Gorgeous Tbabe Solo Stroking Lesson For Viewers
    10:15
    Gorgeous Tbabe Solo Stroking Lesson For Viewers
    2.8K views
    SweetDollx Samba Lesson 1
    14:30
    SweetDollx Samba Lesson 1
    66K views
    japanese shemale instructor yuki Lesson Sportsstyle sex
    05:53
    japanese shemale instructor yuki Lesson Sportsstyle sex
    79.6K views
    Comfortable  Private lesson For Analia
    20:07
    Comfortable Private lesson For Analia
    13K views
    andrea the problematic student need a lesson
    20:27
    andrea the problematic student need a lesson
    Pinko TGirls
    2.4K views
    Guitar lesson
    03:14
    Guitar lesson
    PinkoTGirl
    188.1K views
    Dance lesson part two
    03:08
    Dance lesson part two
    Lizz_ss25
    12.3K views
    Anna's hard lesson in good behavior Part 2
    21:18
    Anna's hard lesson in good behavior Part 2
    42.9K views
    A Lesson in D major TransAngels
    00:47
    A Lesson in D major TransAngels
    Trans Angels
    4.4K views
    I love to Jerk my mouth off... Lumi, the Tranny Slag teen loves to drool waiting for her next facefuck lesson...
    01:36
    I love to Jerk my mouth off... Lumi, the Tranny Slag teen loves to drool waiting for her next facefuck lesson...
    Lumi Estrela
    3.8K views
    Hot shemale in red needs a good lesson of cock
    08:12
    Hot shemale in red needs a good lesson of cock
    Shemale World
    1.8K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Lessons

    • Stockings Bareback
    • Step Sister XXX
    • Cross Dresser Cum
    • Bi Confusion Compilation
    • Sis Bro
    • Femboy Getting Fucked
    • Anal Train
    • Truth or Dare
    • Sissie
    • Feminine Ladyboy
    • Feminized
    • Early Hormone Treatment Results
    • Feminization
    • Instruction
    • Ts Undergoes Satanic Possession Ritual
    • Crossdresser Housewife Fantasy
    • Samantha Nylons
    • Femboygirlfriend
    • Guy Gets Transformed Into Drag Queen
    • Family Rules

    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