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 Dildo Trainer Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Dildo
    Trainer
    Sissy Trainer
    Sissy Dildo
    Sissy Anal Trainer Dildo Instructions
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Sissy Slave
    Amateur Sissy
    Sissy Blowjob
    Sissy Cuckold
    Sissy Gangbang
    Best Videos
    By clicking the content you will also see an ad. AD
    sissy dildo trainer - emma
    13:39
    sissy dildo trainer - emma
    111.5K views
    sissy dildo trainer 2019
    05:48
    sissy dildo trainer 2019
    108.6K views
    Sissy Dildo Trainer (advanced)
    17:02
    Sissy Dildo Trainer (advanced)
    219.4K views
    sissy dildo trainer vol 1
    17:12
    sissy dildo trainer vol 1
    72.6K views
    Sissy Dildo Trainer Compilation
    05:49
    Sissy Dildo Trainer Compilation
    26.1K views
    sissy Shemale Dildo Trainer
    34:16
    sissy Shemale Dildo Trainer
    506.7K 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
    102.7K views
    Sissy Anal Dildo Trainer B2 (advanced)
    11:25
    Sissy Anal Dildo Trainer B2 (advanced)
    48.3K views
    Emasculate your mind
    13:52
    Emasculate your mind
    484.9K views
    The real gape trainer with 100mm girth
    08:39
    The real gape trainer with 100mm girth
    Ylvis88
    12.3K views
    Petra,s graduation party
    01:14:05
    Petra,s graduation party
    PetraTVsletje
    10.2K views
    Sissy Oksana cums very profusely during anal dildo training
    13:54
    Sissy Oksana cums very profusely during anal dildo training
    Oksana2021
    153.5K views
    Big Girls Playing Big Black Toys
    02:49
    Big Girls Playing Big Black Toys
    Melinda James
    12K views
    Dildo Training for Sissies, Femboys, Anal Sluts and Other Cock-hungry Holes - Ride Your Dildo Full of Passion.
    06:11
    Dildo Training for Sissies, Femboys, Anal Sluts and Other Cock-hungry Holes - Ride Your Dildo Full of Passion.
    Sissy Slut Chantal Sweet
    22.6K views
    Seductive Redhead Slut Cums From Anal with Locked Clit
    04:43
    Seductive Redhead Slut Cums From Anal with Locked Clit
    Sonechka25
    3.7K views
    Double cumshot, in my mouth and anal orgasm with all my toys
    11:47
    Double cumshot, in my mouth and anal orgasm with all my toys
    LuziaTv
    1.8K views
    Sissy Sqwirt Trainning
    02:34
    Sissy Sqwirt Trainning
    FrinaXXX
    5.5K views
    Cream
    16:06
    Cream
    Kimberhaven
    62.8K views
    Sissy uses depth trainer
    01:03
    Sissy uses depth trainer
    42.6K views
    Sissy Slut Haileydoll In Chastity Anal Training BBC Dildo
    01:21
    Sissy Slut Haileydoll In Chastity Anal Training BBC Dildo
    Sissy Haileydoll
    58.8K views
    Jasmyne Jaye's Sissy Training Compilation Part 1 of 3
    04:06
    Jasmyne Jaye's Sissy Training Compilation Part 1 of 3
    Jasmyne Jaye
    3.8K views
    Can I do this to your cock or is this too much for you to handle?
    01:16
    Can I do this to your cock or is this too much for you to handle?
    Sissyvalerie69
    3.7K views
    Sissy Cindy faggot love bbc dildo
    05:34
    Sissy Cindy faggot love bbc dildo
    Sissy Cindy Slut
    12.2K views
    Sissy Slut Lisa Riding Toy Till Sissygasm
    04:02
    Sissy Slut Lisa Riding Toy Till Sissygasm
    Lisa Rhea Deville
    2.2K 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
    1.5K views
    Extreme Anal Training with Huge Inflatable Monster Dildo
    05:56
    Extreme Anal Training with Huge Inflatable Monster Dildo
    Jasmine_dlight
    17K views
    Indian Sissy Throat Trains for Daddy - Sissy Victoria
    03:06
    Indian Sissy Throat Trains for Daddy - Sissy Victoria
    Sissy Victoria
    77.2K views
    Sissy Training
    05:11
    Sissy Training
    Juicybunnybuns
    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
    Crossdresser slut gets fucked with dildo
    12:11
    Crossdresser slut gets fucked with dildo
    Sasha Earth
    36K views
    Cabalgata anal
    06:33
    Cabalgata anal
    LuziaTv
    just added
    Slave of Mr. Rodriguez
    09:36
    Slave of Mr. Rodriguez
    Anna Rios
    11.4K 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
    Sissy Pussy Trainer
    02:30
    Sissy Pussy Trainer
    Brat Perversions
    2.1K views
    My New 12 Inch Toy
    08:57
    My New 12 Inch Toy
    Kimberhaven
    26.2K 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
    SissyDoll Anal Sissy Hypno
    01:37
    SissyDoll Anal Sissy Hypno
    26.6K views
    Sissy Trainer Sissy Mindset Reaffirmation Porn Obsession Sissification Feminization Instructions Sissy Way of Life
    11:30
    Sissy Trainer Sissy Mindset Reaffirmation Porn Obsession Sissification Feminization Instructions Sissy Way of Life
    LaraWhiteSissy
    3.8K views
    Sissy Lisa Nale creamy sissy pussy bbc dildo riding
    01:53
    Sissy Lisa Nale creamy sissy pussy bbc dildo riding
    Devotanal
    7.7K views
    practice deep throating bitch
    03:23
    practice deep throating bitch
    Pandora Xysishe
    7.3K views
    Sissy Feminization Blowjob Training and Sissyslave is not allowed to let the Dildo slip out her Mouth for one Hour.
    16:15
    Sissy Feminization Blowjob Training and Sissyslave is not allowed to let the Dildo slip out her Mouth for one Hour.
    Denise Humain
    5.5K views
    CindiCsissy eating my own cum for the first time
    15:08
    CindiCsissy eating my own cum for the first time
    CIndiCsissy
    7.6K views
    Sissy Training Hankeys Big Daddy Medium Micro Chastity Cage
    02:33
    Sissy Training Hankeys Big Daddy Medium Micro Chastity Cage
    A Alexa-CGN
    13.8K views
    Lizz_ss25 anal sissy slut training
    06:00
    Lizz_ss25 anal sissy slut training
    Lizz_ss25
    4.5K views
    Sissy training with bigger dildo
    01:35
    Sissy training with bigger dildo
    Sissy Megan
    5.1K 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
    6.2K views
    Sonechka25 Showed Her Asshole to a Stranger for. Sissy Training 3.
    02:44
    Sonechka25 Showed Her Asshole to a Stranger for. Sissy Training 3.
    Sonechka25
    2.4K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Dildo Trainer

    • Shemale Dildo Trainer
    • Femdom Sissy Training
    • Chastity Machine
    • Japanese Crossdresser Slave BDSM Bondage
    • Kammy Sutra Leaked
    • Permanent Sissification
    • Trans Sister XXX
    • A Sissy's Purpose
    • Secret Sissyboy
    • White Sissies 4 Black Masters
    • Dirty Talk Radio
    • Bi Confusion Sissy Training
    • Turning Cuck Husband Into Faggot
    • Sissygasm Trainer
    • Sissyfication Process
    • Monster Dildos
    • Dildo Instruction
    • Domination Gangbang
    • Just Admit You Like Cock Captions
    • Mind Control

    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