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 Train Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Cute Sissy
    French Sissy
    Sissy Orgasm
    Sissy Spanking
    Sissy Moaning
    Sissy Orgy
    Sissy School
    Sissy Mistress
    Sissy Swallow
    Little Sissy
    Sissy Bnwo
    Sissy Story
    Sissy Fisting
    Japanese Sissy
    Sissy Trap
    Sissy Punishment
    Bbw Sissy
    Ebony Sissy
    Sissy Used
    Fat Sissy
    Best Videos
    By clicking the content you will also see an ad. AD
    training my sissy girl to take step daddys massive cock slow deep
    25:48
    training my sissy girl to take step daddys massive cock slow deep
    241.7K views
    Trained to be a sissy slut
    08:14
    Trained to be a sissy slut
    162.8K views
    AB121 Lustful succubus extreme training
    02:42
    AB121 Lustful succubus extreme training
    Abby Kitty
    156.6K views
    Gorgeous T-girl Sluts Out with Huge Dildo  Hard Anal, Gapes, Pushing Out Cum
    08:12
    Gorgeous T-girl Sluts Out with Huge Dildo Hard Anal, Gapes, Pushing Out Cum
    Melodyfluffington
    138.5K views
    Dirty Mistress Sissy JOI Training Jerk Off Instruction by Iskra Electrical
    08:05
    Dirty Mistress Sissy JOI Training Jerk Off Instruction by Iskra Electrical
    IskraElectrical49
    14K views
    Sissy Maid Service Practicing on a Dildo at Her Fake Glory Hole
    18:20
    Sissy Maid Service Practicing on a Dildo at Her Fake Glory Hole
    Sissy Candy
    20.9K views
    Sissy Training
    03:11
    Sissy Training
    Sissy Bambii
    80.3K views
    Sissy Poppers Hypnose Training IV
    20:31
    Sissy Poppers Hypnose Training IV
    144.5K views
    I fuck my stepbrother's pussy with my big cock
    09:27
    I fuck my stepbrother's pussy with my big cock
    yesid
    94.3K views
    POV Demon Futa Warps Your Subconscious to Worship Cock - Shapeshifting Giantess
    05:08
    POV Demon Futa Warps Your Subconscious to Worship Cock - Shapeshifting Giantess
    Vlad Eros
    41.4K views
    Prolapse Potty Training
    01:07:12
    Prolapse Potty Training
    Sissycdslc
    20.8K views
    Pink Sissy Maid Caught Dressing and Playing and Has a Sissygasm Riding Her Doll
    11:21
    Pink Sissy Maid Caught Dressing and Playing and Has a Sissygasm Riding Her Doll
    Sissy Candy
    51.8K views
    Slutty maid training feminization Holly Hunt turns you into a sissy maid in chastity!
    07:34
    Slutty maid training feminization Holly Hunt turns you into a sissy maid in chastity!
    Holly unt
    28.6K views
    Sissy training dreams
    26:14
    Sissy training dreams
    250.2K views
    Brat Perversions Mandatory BBC Sissy Training
    00:38
    Brat Perversions Mandatory BBC Sissy Training
    littlemissbrat
    44.8K views
    Your Trans BFF Wants to Make You Her Boyfriend's Mall Slut!
    08:12
    Your Trans BFF Wants to Make You Her Boyfriend's Mall Slut!
    Melissa Masters
    81K 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
    156.6K views
    Sissy Dildo Trainer (advanced)
    17:02
    Sissy Dildo Trainer (advanced)
    219.4K views
    Sissy Oksana cums very profusely during anal dildo training
    13:54
    Sissy Oksana cums very profusely during anal dildo training
    Oksana2021
    154.9K views
    blonde femboy fuck machine sissy training!
    13:20
    blonde femboy fuck machine sissy training!
    Cassie Coyote
    94.9K views
    sissy ladyboy shemale gets enema urine in the ass fucks comes in the effeminate ass
    06:37
    sissy ladyboy shemale gets enema urine in the ass fucks comes in the effeminate ass
    femboyass469
    111K views

    Relevant Short videos

    become obsessed with your goals
    become obsessed with your goals
    Starbutts
    36.6K views
    Sissy Anal Training
    Sissy Anal Training
    Sissy Slut Chantal Sweet
    22.4K views
    Anastasia Mistress sexy domina girl in black stockings with small tits dominates by sissy trap strapon
    Anastasia Mistress sexy domina girl in black stockings with small tits dominates by sissy trap strapon
    Anastasia Mistress
    18.9K views
    Stretched Out in Chastity
    Stretched Out in Chastity
    Roxie Black
    10.9K views
    AnitaGape anal training
    AnitaGape anal training
    AnitaGape
    8K views
    Adorable Trap, Strips, Plugs Her Fat Ass and Jerks off for You
    Adorable Trap, Strips, Plugs Her Fat Ass and Jerks off for You
    Melodyfluffington
    12.6K views
    Sissy Hypno Dildo Trainer for Cockcraving anal Sluts - featuring Chantal and the Hankeys Toys Thicky Nicky, Jackpot Monster Cock
    09:34
    Sissy Hypno Dildo Trainer for Cockcraving anal Sluts - featuring Chantal and the Hankeys Toys Thicky Nicky, Jackpot Monster Cock
    Sissy Slut Chantal Sweet
    103.8K views
    POV: Young Gothic Sissy Girl Comes Home And Takes Care Of Your Cock
    09:58
    POV: Young Gothic Sissy Girl Comes Home And Takes Care Of Your Cock
    Vane03_siss
    87.2K views
    Femboy Cumdump Pushes out Gallons of Cum
    07:45
    Femboy Cumdump Pushes out Gallons of Cum
    Gsoqt
    79.5K views
    Anal Fisting Compilation 1 Sissy TS CD
    03:25
    Anal Fisting Compilation 1 Sissy TS CD
    _Sissy
    8.4K views
    POV: Teen Horny Femboy Trains His Ass in Front of the Camera
    13:11
    POV: Teen Horny Femboy Trains His Ass in Front of the Camera
    Liza Femb
    55.8K views
    POV: Your gothic trans mistress puts you in chastity and makes fun of you, putting handcuffs on you and making you worship her feet.
    07:37
    POV: Your gothic trans mistress puts you in chastity and makes fun of you, putting handcuffs on you and making you worship her feet.
    Vane03_siss
    26.5K views
    Trans on a Fuckmachine for Her Neighbor
    06:44
    Trans on a Fuckmachine for Her Neighbor
    Emmy Angeles
    26.1K views
    Sissy Femboy Bondage Feminization Training
    07:36
    Sissy Femboy Bondage Feminization Training
    Wraith931
    39.3K views
    Sissy riding dildo outside
    10:45
    Sissy riding dildo outside
    SissyDaniella
    25.9K views
    Sissy Fuck Machine Training
    07:39
    Sissy Fuck Machine Training
    Mistress Jodie May
    79.9K views
    Sissy Elvi Lynx - Hardcore Big Anal Dildo Penetration
    09:45
    Sissy Elvi Lynx - Hardcore Big Anal Dildo Penetration
    Elvi Lynx
    8.4K views
    Feminization training for white faggot sissy sluts
    05:10
    Feminization training for white faggot sissy sluts
    113.4K views
    Poppers Anal trainning Sissy Slut
    04:18
    Poppers Anal trainning Sissy Slut
    Lola Spais
    342.9K views
    Gothic Sissy Slut In Pink Dress Workouts With Her BBC Dildo
    09:16
    Gothic Sissy Slut In Pink Dress Workouts With Her BBC Dildo
    Vane03_siss
    20.6K views
    PorchaeTS tries new homemade chastity Dick dildo to pleasure the Mrs. Total mind trip.
    04:42
    PorchaeTS tries new homemade chastity Dick dildo to pleasure the Mrs. Total mind trip.
    PorchaeTS
    89.1K views
    Trans Anal Training Cumming Twice From Monster Dildo Hard And Caged
    07:25
    Trans Anal Training Cumming Twice From Monster Dildo Hard And Caged
    Jessica Bloom
    3.4K views
    Feminized Fuck Toy 4 Life
    09:16
    Feminized Fuck Toy 4 Life
    Kimberhaven
    203.2K views
    Cocksuckers Delight
    04:39
    Cocksuckers Delight
    Kimberhaven
    110.1K views
    Sissy Training Volume 4 - Daddy's Home
    05:47
    Sissy Training Volume 4 - Daddy's Home
    302.2K views
    Sissy ladyboy training
    37:03
    Sissy ladyboy training
    410.8K views
    Trans Ria Bentley Trains Stepdaughter Eden Espi for Anal Sex
    08:12
    Trans Ria Bentley Trains Stepdaughter Eden Espi for Anal Sex
    Ria_Bentley
    64.7K views
    Saturday afternoon training
    19:26
    Saturday afternoon training
    H Helentrojan
    5.2K views
    Adorable sissy dildoes her throat and cummy asshole and goes ass to mouth
    10:05
    Adorable sissy dildoes her throat and cummy asshole and goes ass to mouth
    Melodyfluffington
    118.8K views
    AB105 Christmas Girl's Bondage Party-squiting cumshot
    03:23
    AB105 Christmas Girl's Bondage Party-squiting cumshot
    Abby Kitty
    208.5K views
    The best Sissy Trainer (Pop...s)
    12:46
    The best Sissy Trainer (Pop...s)
    226.6K views
    Chastity fox ninja cosplay and huge anal dildo destruction
    15:35
    Chastity fox ninja cosplay and huge anal dildo destruction
    AngelSissyWhore
    11.6K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Train

    • Confused
    • Amateur Young Femboys
    • Interracial Compilations BBC
    • Locked
    • Becoming a Girl
    • Dominated
    • Extreme Pain
    • Music Video
    • Sisy Boy
    • Vibrating Butt Plug
    • Jelqing Exercise Penis
    • Sissyfication Process
    • Male to Female Transformation Fantasy
    • Erotic Asmr
    • Asian Dominatrix
    • Mindfuck
    • Forced Orgasm
    • Transvestites Sissies
    • Sissy-Boys
    • Sissie

    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