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
    -50%
    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
    -60%
    Dating
    Subscriptions
    • Upload
    +14 MONTHS FREE 😱 🍾 🥂 Happy New Year Sale
    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
    • Homemade
    • Mature
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Slave Training Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    You switched to shemale orientation. Do you want to keep searching in the straight section?
    Sissy
    Slave
    Training
    Sissy Slave
    Slave Training
    Sissy Crossdresser
    Bbc Sissy
    Sissy Feminization
    Sissy Husband
    Sissy Chastity
    Young Sissy
    Sissy Fucked
    Sissy Compilation
    Amateur Sissy
    Sissy Blowjob
    Sissy Cuckold
    Submissive Sissy
    Sissy Gangbang
    Sissy Femdom
    Sissy Faggot
    Best Videos
    By clicking the content you will also see an ad. AD
    Sissy Joyce - A real life sissy slave
    01:16
    Sissy Joyce - A real life sissy slave
    Sissy Joyce
    673.9K views
    Sissy Slave Training
    15:45
    Sissy Slave Training
    1.5M views
    Sissyfication
    43:09
    Sissyfication
    1M views
    Sissy sloppy Deepthroat Training for real men. Just another white sissy slave training her throat for BBC
    04:14
    Sissy sloppy Deepthroat Training for real men. Just another white sissy slave training her throat for BBC
    5.1K views
    Sissy Cuckold Fed Creampie And Cum Foot Worship - Jessica Bloom ft Polieana
    05:11
    Sissy Cuckold Fed Creampie And Cum Foot Worship - Jessica Bloom ft Polieana
    Jessica Bloom
    271.2K views
    Submissive Ladyboy Anal Casting, Creampie & Slave Training
    01:25
    Submissive Ladyboy Anal Casting, Creampie & Slave Training
    FilmmakerDiaries
    7.7K views
    family fun 1.mp4
    13:05
    family fun 1.mp4
    1.7M views
    Skinny Ladyboy Anal Casting, Slave Training and Cream Enema
    01:02
    Skinny Ladyboy Anal Casting, Slave Training and Cream Enema
    FilmmakerDiaries
    55.4K views
    mistress cages sissy
    12:29
    mistress cages sissy
    933K views
    Skinny Ladyboy Anal Casting & Slave Training
    00:48
    Skinny Ladyboy Anal Casting & Slave Training
    FilmmakerDiaries
    6K views
    Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
    44:10
    Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
    alinanightsky
    219.2K views
    Submissive Ladyboy Anal Casting & Slave Training
    00:57
    Submissive Ladyboy Anal Casting & Slave Training
    FilmmakerDiaries
    4.2K views
    Degraded and bound Alina learns that her pleasure is on the secon place during exhausting bdsm session
    11:20
    Degraded and bound Alina learns that her pleasure is on the secon place during exhausting bdsm session
    alinanightsky
    294.3K views
    Submissive Asian Ladyboy Anal Casting & Slave Training
    00:31
    Submissive Asian Ladyboy Anal Casting & Slave Training
    FilmmakerDiaries
    13K views
    Jessica Bloom Dominates Her new Pig Fuck Toy Jenby Doll
    06:23
    Jessica Bloom Dominates Her new Pig Fuck Toy Jenby Doll
    Jessica Bloom
    231.2K views
    Big Cock Ladyboy Anal Casting and Slave Training
    00:49
    Big Cock Ladyboy Anal Casting and Slave Training
    FilmmakerDiaries
    2.8K views
    Sissy in Training
    01:27:33
    Sissy in Training
    378.7K views
    Skinny Submissive Ladyboy Self Anal Fisting and Slave Training
    00:30
    Skinny Submissive Ladyboy Self Anal Fisting and Slave Training
    FilmmakerDiaries
    6.8K views
    How to train your sissy ass
    17:41
    How to train your sissy ass
    646.5K views
    Sissy submissive slave training
    01:11
    Sissy submissive slave training
    3.5K views
    A guide to sissication: Beginner - Am I a sissy?
    23:32
    A guide to sissication: Beginner - Am I a sissy?
    729.1K views
    AB106 Conpletely domesticated kinky sissy slave- face sitting cumshot edging
    03:20
    AB106 Conpletely domesticated kinky sissy slave- face sitting cumshot edging
    Abby Kitty
    154.4K views
    How to Train Your Sissy Boyfriend
    08:12
    How to Train Your Sissy Boyfriend
    Brat Perversions
    91.5K views
    AB085 Lustful Abby Kitty be Master's sissy slave -chastity (Chinese and English subtitles)
    03:09
    AB085 Lustful Abby Kitty be Master's sissy slave -chastity (Chinese and English subtitles)
    Abby Kitty
    78.8K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    1.8M views
    PREVIEW BEST SISSY SLAVE REAL TRAINING BY TS GODDESS OF MILK BAREBACK DEEPTHROAT CUM SPANKING GAG USE FULL ON ONLYFANS
    02:43
    PREVIEW BEST SISSY SLAVE REAL TRAINING BY TS GODDESS OF MILK BAREBACK DEEPTHROAT CUM SPANKING GAG USE FULL ON ONLYFANS
    TsGoddessofMilk
    58.6K views
    CD TRAP SISSY EDUCATION TRAINING 101
    01:27:33
    CD TRAP SISSY EDUCATION TRAINING 101
    916.1K views
    Sissy slave fuck and piss comp.
    32:44
    Sissy slave fuck and piss comp.
    Bound_Sissy
    6.6K views
    Bound Sissy Gets Cock Milked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana
    07:35
    Bound Sissy Gets Cock Milked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana
    Jessica Bloom
    47.1K views
    Skinny Asian Sissy Slave Anal Training Until Squirt Wearing Chastity Cage
    23:57
    Skinny Asian Sissy Slave Anal Training Until Squirt Wearing Chastity Cage
    MaureenNadh
    5.5K views
    Male to female gender transformation smoking whore
    16:00
    Male to female gender transformation smoking whore
    674.4K views
    Feminized Sissy Slave Dildo Anal Training and Sissygasm in Chastity
    08:40
    Feminized Sissy Slave Dildo Anal Training and Sissygasm in Chastity
    Joanna CD
    4.9K views
    dominant stepmom helps out her sissy slave
    05:59
    dominant stepmom helps out her sissy slave
    Pure Ts
    342.5K views
    BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
    07:34
    BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
    Denise Humain
    5.3K views
    anal destruction and face slapping for maso whore
    10:41
    anal destruction and face slapping for maso whore
    ActorFab
    84.3K views
    Sissy slave Oksana gets sissygasm with her hands free from anal training while riding a dildo
    01:02
    Sissy slave Oksana gets sissygasm with her hands free from anal training while riding a dildo
    Oksana2021
    7.8K views
    Real sissy hypnotic
    24:43
    Real sissy hypnotic
    218.2K views
    BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys
    08:00
    BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys
    Denise Humain
    5.9K views
    Training to become a sissy cuckold
    03:26
    Training to become a sissy cuckold
    amatorxxx
    612K views
    My Master made me do it and I am obedient to Him, because I am his sissy slave. Thanks to my Master.
    09:10
    My Master made me do it and I am obedient to Him, because I am his sissy slave. Thanks to my Master.
    Oksana2021
    6.9K views
    sissy clitty chastity
    07:26
    sissy clitty chastity
    520.6K views
    Hooded Sissy Slave Deepthroats Cock and Takes It in Her Ass
    05:48
    Hooded Sissy Slave Deepthroats Cock and Takes It in Her Ass
    Elise Woods
    4.5K views
    Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor
    05:03
    Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor
    alinanightsky
    397.8K views
    Sissy slave Elise fucks herself with dildo
    07:50
    Sissy slave Elise fucks herself with dildo
    Elise Woods
    5.8K views
    TRANSEROTICA Sub TS Natalie Mars Bound by MILF Dee Williams
    12:05
    TRANSEROTICA Sub TS Natalie Mars Bound by MILF Dee Williams
    Trans Erotica
    435.8K views
    Sissy Whore Denise Humain Make Up is done but still hair struggle Sissy Slave Feminization Dress Up Training.
    09:53
    Sissy Whore Denise Humain Make Up is done but still hair struggle Sissy Slave Feminization Dress Up Training.
    Denise Humain
    6K views
    TS Sucking the Gimp
    13:38
    TS Sucking the Gimp
    Dark Films Trans
    21.1K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Slave Training

    • Brainwashing You Into Sissy Faggot
    • Feminization Training
    • Submissive Crossdresser and Master
    • Femboy Domination
    • Shemale Mistress Trains Slave
    • Femdom Humiliation
    • A Guide to Sissification Beginner
    • White Boy Becomes Bitch for BBC
    • Degrading Slaves
    • First Time Crossdressing
    • Tranny Dominatrix
    • Dominant Woman
    • Cum Eating Trainer
    • Shemales Spanking
    • Forced Orgasm BDSM
    • Ladyboy Punished
    • Women Pegging Men
    • The Sissy's Future
    • Feminize Yourself
    • Chastity Fucked

    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