PornPorn Transgender • US
  • Straight
  • Gay
  • Transgender
  • Videos
  • Short videos
  • photos
  • Users
    Forgot password
    Sign in with Google
    Sign in with X
    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
    Subscriptions Liked Watch History
    Newest Videos Best Videos Short Videos Top Creators Awards 2025
    • American
    • 4K Porn
    • HD Videos
    • VR Porn
    • Amateur
    • Anal
    • Anal Masturbation
    • Anal Toy
    • Asian
    • Babysitter
    • Bareback
    • BBW
    • BDSM
    • Behind The Scenes
    • Big Ass
    • Big Black Cock
    • Big Cock
    • Big Tits
    • Black
    • Blowjob
    • Bondage
    • Brazilian
    • British
    • Cartoon
    • Chinese
    • Colombian
    • Compilation
    • Couple
    • Creampie
    • Cuckold
    • Cum In Mouth
    • Cumshot
    • Dildo
    • Domination
    • Double Penetration
    • English
    • Fetish
    • FTM
    • Gangbang
    • German
    • Group Sex
    • Guy Fucks Shemale
    • Handjob
    • Hentai
    • Homemade
    • Indian
    • Interracial
    • Japanese
    • Ladyboy
    • Lingerie
    • Massage
    • Masturbation
    • Mature
    • Mexican
    • MILF
    • Outdoor
    • Petite
    • Pissing
    • POV
    • Public
    • Role Play
    • Rough Sex
    • SFW
    • Shemale Fucks Girl
    • Shemale Fucks Guy
    • Shemale Fucks Shemale
    • Sissy
    • Small Cock
    • Small Tits
    • Solo
    • Stockings
    • Teen
    • Thai
    • Threesome
    • Trans Man
    • Trans Woman
    • Transgender
    • Vintage
    • All categories

    Sissy Boy Training Trans Porn Videos

    All Short videos
    Newest
    Best Videos
    Premium Videos
    By Rating
    • By Rating
    • By Views
    • By Comments
    Date
    • All
    • 1 Day
    • 7 Days
    • 30 Days
    • Year 2026
    • Year 2025
    Quality
    • All
    • 720p+
    • 1080p+
    • 2160p+
    FPS
    • All
    • 30 FPS
    • 60 FPS
    Duration
    • All
    • 0~2 min
    • 2~5 min
    • 5~10 min
    • 10~30 min
    • 30+ min
    • Full Video
    Production
    • All
    • Producers
    • xHamster Creators
    Sissy
    Sissy Boys
    Sissy Trained
    Teen Sissy Boy
    Young Sissy
    Sissy Feminization
    Amateur Sissy
    Sissy Crossdresser
    Sissy Fuck
    Submissive Sissy
    Sissy Blowjob
    Sissy Lingerie
    Sissy Chastity
    Russian Sissy
    Sissy Gangbang
    Homemade Sissy
    Sissy Compilation
    Fuck Boy
    By clicking the content you will also see an ad. AD
    A White Boys Purpose
    23:50
    A White Boys Purpose
    Kimberhaven
    603.2K views
    Sissy Boy Training
    04:08
    Sissy Boy Training
    784.6K views
    Sissy Boy Training Video: Surrender to Black Cocks
    04:20
    Sissy Boy Training Video: Surrender to Black Cocks
    855.6K views
    Nylon Sissy Slut Michelle Wakeup Training for the Show at Beijing Hotel
    42:40
    Nylon Sissy Slut Michelle Wakeup Training for the Show at Beijing Hotel
    Michael Ernandes
    16.9K views
    Sissy Boi Training
    02:42
    Sissy Boi Training
    55.1K views
    Sexy sissy Ponyboy Showing his nude body and high heels
    05:45
    Sexy sissy Ponyboy Showing his nude body and high heels
    Letany Ponny
    169.3K views
    Dirty talking sissy boy fat dildo fuck POV
    02:15
    Dirty talking sissy boy fat dildo fuck POV
    Viper Fierce
    22.9K views
    Sissy Trainnig at Home
    02:21
    Sissy Trainnig at Home
    Lola Spais
    35.2K views
    Cute trap boy gets big dildo. Cock POV video
    03:15
    Cute trap boy gets big dildo. Cock POV video
    hjohny66
    42.3K views
    Homemade Sex Compilation: Girl Fucks Shemale and She Cums Hands Free
    02:27
    Homemade Sex Compilation: Girl Fucks Shemale and She Cums Hands Free
    Lola Spais
    26.1K views
    Your sissy boy training your sloppy ass to fisting
    07:10
    Your sissy boy training your sloppy ass to fisting
    Sofi_elfqueen
    just added
    Horny Sissy Toying Her Ass with Transparent Dildo in the Supermarket Parking Lot While Cars Pass by
    01:07
    Horny Sissy Toying Her Ass with Transparent Dildo in the Supermarket Parking Lot While Cars Pass by
    Traviezisha
    1.2K views
    Mini noisy buttslut compilation
    06:00
    Mini noisy buttslut compilation
    Phluff2
    10.3K views
    New tattoo same slut
    03:27
    New tattoo same slut
    Emma fey
    5.7K views
    Sissy Lana in chastity trains her holes
    06:03
    Sissy Lana in chastity trains her holes
    Sissy Lana
    9.9K views
    BBC destroyed white boypussy
    02:50
    BBC destroyed white boypussy
    5.1K views
    Awesome Sissygasm
    01:36
    Awesome Sissygasm
    Lola Spais
    5.8K views
    Sissy Online Training Class- How Sissys Use Their Dicks
    02:00
    Sissy Online Training Class- How Sissys Use Their Dicks
    Apple00001
    4.6K views
    dildo training (sissy boy in action)
    01:01
    dildo training (sissy boy in action)
    65.7K views
    Sissy Faggot slut moaning
    04:11
    Sissy Faggot slut moaning
    Sissy Cindy Slut
    5.1K views
    sissyboy training
    05:14
    sissyboy training
    Boycho Atanasov
    12.1K views
    Sissy Boy: Deepthroat Training
    02:30
    Sissy Boy: Deepthroat Training
    108.1K views
    Crossdressing boy bitch Transformation to tranny Girl
    06:07
    Crossdressing boy bitch Transformation to tranny Girl
    11.3K views
    In the elevator
    02:47
    In the elevator
    Simone Xdressing
    2.5K views
    Sissy Whore Cindy Moan and cum
    02:47
    Sissy Whore Cindy Moan and cum
    Sissy Cindy Slut
    2.8K views
    Riding a dildo, Me Emma, crossdresser sissy boy
    02:18
    Riding a dildo, Me Emma, crossdresser sissy boy
    Twokisses
    3.5K views
    Sissy Ass Fucked Right Over the Camera Compilation
    00:49
    Sissy Ass Fucked Right Over the Camera Compilation
    Lola Spais
    4.6K views
    Mistress Fucking Slave Crossdresser Cumshot Handsfree
    00:26
    Mistress Fucking Slave Crossdresser Cumshot Handsfree
    Lola Spais
    4.6K views
    Pierce My Ass Babe Anal Sissy Training
    00:59
    Pierce My Ass Babe Anal Sissy Training
    Lola Spais
    2.2K views
    Girl and Trans Double Fuck
    00:38
    Girl and Trans Double Fuck
    Lola Spais
    4.2K views
    Wonderful Reality
    01:27
    Wonderful Reality
    Lola Spais
    2.3K views
    Stretching my boi pussy
    01:28
    Stretching my boi pussy
    2.2K views
    Ballet boy is trained to be a sissy whore
    06:47
    Ballet boy is trained to be a sissy whore
    Sissy_Boy_Anna
    4.4K views
    Girl Fucks Sissy with Spiked Vibro Cock Outdoor
    01:09
    Girl Fucks Sissy with Spiked Vibro Cock Outdoor
    Lola Spais
    3.8K views
    Nylon Slut Michelle Web Show From Beijing Hotel - Episode Ii
    01:14:55
    Nylon Slut Michelle Web Show From Beijing Hotel - Episode Ii
    Michael Ernandes
    2.2K views
    Boi-Pussy Training
    00:39
    Boi-Pussy Training
    Sissy Christiane
    3.3K views
    Another dance show off of me
    06:27
    Another dance show off of me
    Simone Xdressing
    2.3K views
    Sissy Boy Lovelaska - My ass dancing 27
    04:52
    Sissy Boy Lovelaska - My ass dancing 27
    Lovelaska
    4.3K views
    Sissy hoe dancing
    01:03
    Sissy hoe dancing
    Elizabeth
    2.3K views
    SISSY PISSY BOY IN TRAINING
    07:07
    SISSY PISSY BOY IN TRAINING
    LiveNLove
    2.9K views
    Sissy femboy anal training with plug, vibrator and dildo
    05:55
    Sissy femboy anal training with plug, vibrator and dildo
    CrazyBoy95
    3.6K views
    New year’s model Sissy trans Boy
    01:23
    New year’s model Sissy trans Boy
    Artur_Angel
    2.4K views
    The sissy and a dance
    07:19
    The sissy and a dance
    Simone Xdressing
    2.1K views
    sissy boy anal training with dildo
    02:07
    sissy boy anal training with dildo
    Jordyn
    2.1K views
    Anny Sex 44
    01:02
    Anny Sex 44
    Annyfist
    1.2K views
    Doggy anal training session with big dildo
    01:22
    Doggy anal training session with big dildo
    CrazyBoy95
    2.5K views

    Categories Related to Sissy Boy Training

    • Young Sissy Boy
    • First Time With Trans Woman
    • Teen Traps and Sissy Femboys
    • Sissy Training Joi
    • Male to Female Transformation
    • Sissy Slut Trainer
    • Femdom Sissy Training
    • Step Mom Sex
    • Sissy Whore Training
    • Shemale Fucks Guy First Time

    Searches Related to Sissy Boy Training

    • Sissy Boy Training
    • Sissy Gloryhole Training
    • Extreme Sissy BBC Trainer
    • Shemale Sissy Training
    • Femboy Punished
    • Trans Dogging
    • Bratty Sis
    • High Class MILF
    • Sissy-Boys
    • Sissy Whiteboy Training
    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