PornPorn Transgender • US
  • 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
    • Black
    • Big Cock
    • 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
    LET IT SNOW, LET IT SAVE! ☃️ Faphouse Discounts – Winter Edition
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Black
    • Big Cock
    • Shemale Fucks Shemale
    • Amateur
    • Shemale Fucks Girl
    • Sissy
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Big Black Cock
    • Cum In Mouth
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Training A Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Cute Sissy
    Chastity Sissy
    Sissy Dominated
    Sissy Domination
    Sissy Transformation
    Sissy Public
    Sissy Orgasm
    Sissy POV
    Sissy Swallow
    Sissy Spanking
    Japanese Sissy
    Sissy Orgy
    French Sissy
    Sissy School
    Sissy Moaning
    Degraded Sissies
    Bbw Sissy
    Arab Sissy
    Sissy Trap
    Sissy Story
    Best Videos
    By clicking the content you will also see an ad. AD
    Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson
    05:29
    Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson
    658.7K views
    I fuck my stepsister's busty for her big pussy
    07:14
    I fuck my stepsister's busty for her big pussy
    Yeison
    2.3M views
    Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage
    10:16
    Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage
    Jessica Bloom
    76.4K views
    Mistress Eudora's Anal Slut
    05:28
    Mistress Eudora's Anal Slut
    Loren Aprile
    151.8K views
    Sissy faggot fantasy
    29:49
    Sissy faggot fantasy
    293.9K views
    SISSY TRANSFORMATION
    11:07
    SISSY TRANSFORMATION
    655.7K views
    Sissy Poppers Trainer 1
    04:07
    Sissy Poppers Trainer 1
    316.9K views
    Admit That You Are a Slut For My Cum
    13:12
    Admit That You Are a Slut For My Cum
    Natalie Napoli
    337.5K views
    For Sissies  How to obtain past your oral fixating
    14:15
    For Sissies How to obtain past your oral fixating
    237.3K views
    Jerk off While I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI
    07:47
    Jerk off While I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI
    Jessica Bloom
    330K views
    Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
    18:27
    Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
    Vane03_siss
    231.7K views
    AB094 Lustful teacher extreme trained -Milking 65cm dildo  (Chinese and English subtitles)
    03:52
    AB094 Lustful teacher extreme trained -Milking 65cm dildo (Chinese and English subtitles)
    Abby Kitty
    388.3K views
    CD TRAP SISSY EDUCATION TRAINING 101
    01:27:33
    CD TRAP SISSY EDUCATION TRAINING 101
    936.7K views
    SissyAline - Train your sissy pussy, be a buttslut
    09:06
    SissyAline - Train your sissy pussy, be a buttslut
    427.7K views
    Feminize Yourself
    16:07
    Feminize Yourself
    449K views
    Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl
    05:43
    Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl
    alinanightsky
    346.4K views
    Sissy CD sucks and is fucked
    08:25
    Sissy CD sucks and is fucked
    1.4M views
    TS Cumslut Elf Fucked Hard By Santa - Ass to Mouth And Facial Jessica Bloom
    06:43
    TS Cumslut Elf Fucked Hard By Santa - Ass to Mouth And Facial Jessica Bloom
    linktree
    19.8K views
    Daddy's Good Girl!
    08:12
    Daddy's Good Girl!
    Pure Ts
    953.2K views
    POV housemate finds your panties and feminizes you JOI dominant trans girl
    11:53
    POV housemate finds your panties and feminizes you JOI dominant trans girl
    Holly unt
    168.1K views
    AMBERSIS SISSY CUM SLUT
    06:20
    AMBERSIS SISSY CUM SLUT
    473.8K views
    Kira caught during self-bondage
    02:45
    Kira caught during self-bondage
    Twistedrama
    50.3K views
    sissy Cock Worship
    04:53
    sissy Cock Worship
    570.8K views
    Anal orgasm, cumshots in my mouth, compilation of my hot cumshots
    05:49
    Anal orgasm, cumshots in my mouth, compilation of my hot cumshots
    LuziaTv
    22.9K views
    Anal training for experienced anal sluts
    27:27
    Anal training for experienced anal sluts
    231.2K views
    Petra,s day in the woods
    30:59
    Petra,s day in the woods
    PetraTVsletje
    92.9K views
    I turned my straight roommate intro trans wife
    05:20
    I turned my straight roommate intro trans wife
    linktree
    521.9K views
    Cum ride with me
    12:10
    Cum ride with me
    FapHouse
    453.8K views
    A White Boys Purpose
    23:50
    A White Boys Purpose
    Kimberhaven
    606.4K views
    Urethral Tube Stimulation with Chastity Cage
    07:00
    Urethral Tube Stimulation with Chastity Cage
    Reina Hanno
    47.8K views
    BBC Fucks a Slutty Crossdresser Without Limits
    32:44
    BBC Fucks a Slutty Crossdresser Without Limits
    Trans and Co
    390.1K views
    Sissy Cum Training
    12:16
    Sissy Cum Training
    139.8K views
    anal destruction and face slapping for maso whore
    10:41
    anal destruction and face slapping for maso whore
    ActorFab
    112K views
    Craving CockWhore - Joi Sissy train
    08:45
    Craving CockWhore - Joi Sissy train
    189.7K views
    You are a woman -sissy trainer
    04:12
    You are a woman -sissy trainer
    360.6K views
    Story of when daddy pimped me out. First week. Anal toy.
    08:50
    Story of when daddy pimped me out. First week. Anal toy.
    Sunaxfemiknulla
    19.3K views
    sissy feminization instructions
    07:22
    sissy feminization instructions
    256.5K views
    Submissive femboy is feminized and fucked
    08:30
    Submissive femboy is feminized and fucked
    Crystal Phoenix
    301.8K views
    Cocklust sissy trainer
    09:38
    Cocklust sissy trainer
    212.5K views
    I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI
    05:31
    I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI
    Melissa Wet Tales
    99.1K views
    Sissy Trainer Rus - Feminization Instruction
    05:01
    Sissy Trainer Rus - Feminization Instruction
    399.1K views
    Sissy in Training
    01:27:33
    Sissy in Training
    385.7K views
    Sissy Slut Motel
    58:39
    Sissy Slut Motel
    731.8K views
    Sissy 4: Cum Lover
    10:16
    Sissy 4: Cum Lover
    784.6K views
    Long Anal Session for Hurting Emma Tied to the Bench
    01:05:06
    Long Anal Session for Hurting Emma Tied to the Bench
    FapHouse
    278.1K views
    Will Sin Strips and Plays with Herself
    13:26
    Will Sin Strips and Plays with Herself
    Will__sin
    12.6K views
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    29:33
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    Ria_Bentley
    2.6M views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Training A Sissy

    • Drag Queen
    • Sissypop by Futah
    • Out of Control
    • Dress up
    • Masturbation Instructions
    • Rough Pounding
    • Jerk off Challenge
    • Erotic Audio
    • Grindr Bb CD
    • Nasty Amateurs
    • Men Dressed as Women
    • Naked Femboys
    • Standing Doggystyle
    • Youngster
    • Cuck Cleanup
    • Femboygirlfriend
    • Screaming Orgasms
    • Asshole Stretching
    • Farting on Dick
    • Remote Vibrator
    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