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
    -60%
    Dating
    Subscriptions
    • Upload
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday 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 Trainer Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy POV
    Chastity Sissy
    Sissy Public
    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
    Best Videos
    By clicking the content you will also see an ad. AD
    Shape Of You PMV - Sissy Anal Trainer
    03:56
    Shape Of You PMV - Sissy Anal Trainer
    131.6K views
    Assisted Masturbation: A Personal Trainer's Naughty Lesson Plan
    06:48
    Assisted Masturbation: A Personal Trainer's Naughty Lesson Plan
    Crossdresserkitty
    1.7K views
    Sissy Slut Lisa Riding Toy Till Sissygasm
    04:02
    Sissy Slut Lisa Riding Toy Till Sissygasm
    Lisa Rhea Deville
    2.2K views
    Sexy Gym trainer get Fucked, Leggings Asian Hentai cosplay 5
    05:41
    Sexy Gym trainer get Fucked, Leggings Asian Hentai cosplay 5
    Haru
    14.3K views
    Master Trainer's Personal Training No. 30: Outdoor Restraint Vibrator Training
    06:18
    Master Trainer's Personal Training No. 30: Outdoor Restraint Vibrator Training
    megu2002
    1.2K views
    sissy transsexual dick trainer
    06:48
    sissy transsexual dick trainer
    84.2K views
    Mistress Christine - Chapter 1 - Chastity
    05:11
    Mistress Christine - Chapter 1 - Chastity
    ChristineWest120
    3.3K views
    Sissy Bitch Trainer gifs
    07:14
    Sissy Bitch Trainer gifs
    180.4K views
    Outdoor Public Slutwalk in Sexy Pink Outfit
    03:29
    Outdoor Public Slutwalk in Sexy Pink Outfit
    SusyTrav_AnalQueen
    3.5K views
    sissy training
    17:12
    sissy training
    41.7K views
    Lonely Trans Wife Strips In Bed & Play With Her Small Clit Squirting All Over Her Clit
    04:32
    Lonely Trans Wife Strips In Bed & Play With Her Small Clit Squirting All Over Her Clit
    Soloregin
    22.5K views
    best Sissy out there
    14:37
    best Sissy out there
    316.4K views
    Extreme Anal Training with Huge Inflatable Monster Dildo
    05:56
    Extreme Anal Training with Huge Inflatable Monster Dildo
    Jasmine_dlight
    17K views
    Sissy Shemale Cock Trainer
    06:31
    Sissy Shemale Cock Trainer
    916.6K views
    Ria Bentley Sissy Training For Giving Strangers Blowjobs
    07:04
    Ria Bentley Sissy Training For Giving Strangers Blowjobs
    Ria_Bentley
    6.4K views
    Sissy Crossdresser Pussy Tease
    00:52
    Sissy Crossdresser Pussy Tease
    littlemissbrat
    31.3K views
    BBC VS SISSY MMXXI PT1
    01:35
    BBC VS SISSY MMXXI PT1
    12.1K views
    Sissy Training
    05:11
    Sissy Training
    Juicybunnybuns
    2K views
    Indian Sissy Throat Trains for Daddy - Sissy Victoria
    03:06
    Indian Sissy Throat Trains for Daddy - Sissy Victoria
    Sissy Victoria
    77.2K views
    Jasmine Dlight - How to Keep a Mistress Happy with a Clean Session - Douching Guide
    01:28
    Jasmine Dlight - How to Keep a Mistress Happy with a Clean Session - Douching Guide
    Jasmine_dlight
    2.5K views

    Relevant Short videos

    Full Nude Watching Sissy Trainer Vid
    Full Nude Watching Sissy Trainer Vid
    Zoeydoll
    950 views
    Watching Sissy Trainer Video
    Watching Sissy Trainer Video
    Zoeydoll
    1.3K views
    Sissy trainer
    Sissy trainer
    lekq41
    605 views
    Sissy Motivation 4: Sex Machine Sissy Trainer, Sissy Instruction, Sissification, Femboy
    Sissy Motivation 4: Sex Machine Sissy Trainer, Sissy Instruction, Sissification, Femboy
    Margo-apollo
    846 views
    Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune
    Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune
    Fiona Fortune
    466 views
    Hands free anal cum in chastity cage vladasexytrans
    Hands free anal cum in chastity cage vladasexytrans
    Vladasexytrans
    9.6K views
    Sissy Cocksucking Trainer
    03:51
    Sissy Cocksucking Trainer
    249.1K views
    THE WAY A SISSY SEES THE WORLD-Trainer
    04:45
    THE WAY A SISSY SEES THE WORLD-Trainer
    127.6K views
    DSP SISSY FETISH TRAINER
    03:30
    DSP SISSY FETISH TRAINER
    61.1K views
    Sissy Slut posing in high heels
    06:01
    Sissy Slut posing in high heels
    Orchidee35
    4.5K views
    TS Ria Bentley Gives Sissification Sissy Slut Hookup Training
    08:12
    TS Ria Bentley Gives Sissification Sissy Slut Hookup Training
    Ria_Bentley
    6.8K views
    Chastity Belt
    08:05
    Chastity Belt
    violet_bisex
    2K views
    Emma Stretching her Ass
    04:43
    Emma Stretching her Ass
    25.6K views
    Crossdresser slut gets fucked with dildo
    12:11
    Crossdresser slut gets fucked with dildo
    Sasha Earth
    36K views
    A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
    28:23
    A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
    Denise Humain
    11.9K views
    Material Sissy Girl
    04:24
    Material Sissy Girl
    14.5K views
    SISSY ANAL TRAINER - LINK'S SISSY AWAKENING (METRONOME)
    33:39
    SISSY ANAL TRAINER - LINK'S SISSY AWAKENING (METRONOME)
    47.6K views
    Sissy Training 2
    03:18
    Sissy Training 2
    KatyKoroleva
    4K views
    Cabalgata anal
    06:33
    Cabalgata anal
    LuziaTv
    just added
    Sissy Trance Trainer - Minimal Sound (PMV)
    02:54
    Sissy Trance Trainer - Minimal Sound (PMV)
    159K views
    Slave of Mr. Rodriguez
    09:36
    Slave of Mr. Rodriguez
    Anna Rios
    11.4K views
    Pansexual Sissy Slut Cam Whore Hypno Edging Trainer  One
    07:30
    Pansexual Sissy Slut Cam Whore Hypno Edging Trainer One
    67.9K views
    My New 12 Inch Toy
    08:57
    My New 12 Inch Toy
    Kimberhaven
    26.2K views
    Sissy Slut Trains her Throat on Big Purple Dildo
    02:16
    Sissy Slut Trains her Throat on Big Purple Dildo
    CumslutSasha
    3.6K views
    BIMBO
    01:10
    BIMBO
    Juicybunnybuns
    4.3K views
    Sissy Pussy Trainer
    02:30
    Sissy Pussy Trainer
    Brat Perversions
    2.1K views
    Hands free Cumies Trainer
    05:51
    Hands free Cumies Trainer
    48.6K views
    the sissy maid will..... sissyhypno trainer
    04:47
    the sissy maid will..... sissyhypno trainer
    15.7K views
    NEW SISSY GHANIYAH, AU Asian Crossdresser aroused by sissyfication, hypno trainer real homemade CD03
    01:51
    NEW SISSY GHANIYAH, AU Asian Crossdresser aroused by sissyfication, hypno trainer real homemade CD03
    Ghaniyah
    13.8K views
    Sissy training with KatyKoroleva
    16:46
    Sissy training with KatyKoroleva
    KatyKoroleva
    11.3K 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
    (Part - 1) Mystic Diva hijabi crossdresser geting coc k suc king training in niqab
    09:16
    (Part - 1) Mystic Diva hijabi crossdresser geting coc k suc king training in niqab
    Mystic Diva
    9.4K views
    SISSY PERFECT TRAINER
    05:13
    SISSY PERFECT TRAINER
    30.7K views
    • Back
    • 1
    • ...
    • 4
    • 5
    • 6
    • 7
    • 8
    • ...
    • 80
    • Next

    Searches Related to Sissy Trainer

    • Bbc Femboi Compilation
    • Instructions
    • Transgender Step Sister Porn
    • Take Like Bitch Boy
    • Role Play
    • Femboys Fucking
    • Faggot JOI
    • Sissy Motivation
    • Begging
    • Whored Out
    • Sissyboy-5
    • Chastity Cage
    • Cuckold Trainer
    • Guide
    • Bdsm Extreme
    • Ladyboystar
    • Fem Boys
    • Submissive
    • Transexual Cheerleader
    • Become Shemale

    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