PornPorn Gay • 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
    • Old & Young
    • Daddy
    • Amateur
    • Bear
    • All categories
    Live Sex
    Categories
    • Big Cock
    • Bareback
    • Crossdresser
    • Daddy
    • Black
    • 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
    • Twink
    • Young
    • Bareback
    • Ass
    • Bear
    • All categories
    Faphouse
    Premium Videos
    Dating
    Subscriptions
    • Upload
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Big Cock
    • Bareback
    • Crossdresser
    • Daddy
    • Black
    • Amateur
    • Blowjob
    • Old & Young
    • Straight Guy
    • Twink
    • Femboy
    • Homemade
    • BBC
    • Mexican
    • Grandpa
    • Interracial
    • Cum Swallowing
    • American
    • Compilation
    • Masturbation
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Train Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Gay Sissy Training
    BBC Sissy Training
    Best Videos
    By clicking the content you will also see an ad. AD
    Jason receives merciless and painful slaps while being humiliated
    02:24
    Jason receives merciless and painful slaps while being humiliated
    Pete Knight
    115.5K views
    Sissy Training Verbal For UNCUT LOVER
    04:13
    Sissy Training Verbal For UNCUT LOVER
    Onlyfans
    180K views
    REAL SISSY TRAINING BY A REAL BBC MASTER
    01:13
    REAL SISSY TRAINING BY A REAL BBC MASTER
    85.6K views
    Dirty Insults and Domination to Make You Swallow Your Own Cum
    07:22
    Dirty Insults and Domination to Make You Swallow Your Own Cum
    Kinkymah
    7.6K views
    Ass to Mouth
    05:06
    Ass to Mouth
    FapHouse
    9.1K views
    Blonde Sissy Slut Riding Her Dildo
    09:48
    Blonde Sissy Slut Riding Her Dildo
    Snuskis80
    18.4K views
    Real deep and very sloppy deepthroat
    10:11
    Real deep and very sloppy deepthroat
    Michael Freeman
    6.8K views
    Anal training with big dildos from Mr hankeys
    18:45
    Anal training with big dildos from Mr hankeys
    Big Bat
    22.9K views
    using my sub slave, spank, golden shower, cbt, gagging, sub trainning
    11:27
    using my sub slave, spank, golden shower, cbt, gagging, sub trainning
    Dirty Dog
    43.5K views
    Black Guy Jerking Off, While Cumming & Moaning, Dirty Talking (Shooting A Load & Busting A Nut)
    03:11
    Black Guy Jerking Off, While Cumming & Moaning, Dirty Talking (Shooting A Load & Busting A Nut)
    Jamdown26
    30.6K views
    Sissy POV follow me around like a good boy.
    01:11
    Sissy POV follow me around like a good boy.
    Onlyfans
    24.4K views
    Blonde Sissy Slut Riding Her Dildo
    02:46
    Blonde Sissy Slut Riding Her Dildo
    Snuskis80
    5.7K views
    Sissy In A Green Bikini Riding A Black Dildo
    03:10
    Sissy In A Green Bikini Riding A Black Dildo
    Snuskis80
    7.5K views
    Blonde Sissy Riding Her Black Dildos
    07:36
    Blonde Sissy Riding Her Black Dildos
    Snuskis80
    13.3K views
    Sissy Riding Dildos In High Heels
    03:18
    Sissy Riding Dildos In High Heels
    Snuskis80
    9.6K views
    Going Deep DEEP ft David Anderson
    11:53
    Going Deep DEEP ft David Anderson
    Dirty David
    16.6K views
    Just a open hole ft David Anderson
    33:36
    Just a open hole ft David Anderson
    FapHouse
    6.4K views
    FFantastic FFun with GK128 4 inch diameter butt plug
    04:24
    FFantastic FFun with GK128 4 inch diameter butt plug
    Opalou
    814 views
    Bubble butt twink sissy rides dildos in the bathroom  anal training big dildoa
    05:34
    Bubble butt twink sissy rides dildos in the bathroom anal training big dildoa
    Marcus Domes
    7.7K views
    Cute femboy having sex with a fuck machine
    11:41
    Cute femboy having sex with a fuck machine
    Sasha Earth
    2.6K views
    Sissy In Black Riding Her Dildos
    10:36
    Sissy In Black Riding Her Dildos
    Snuskis80
    828 views
    Sissy training turning him into a cock loving slut
    07:15
    Sissy training turning him into a cock loving slut
    BiHowRu
    17.9K views
    Sissy Riding Two Different Dildos
    03:52
    Sissy Riding Two Different Dildos
    Snuskis80
    14.3K views
    Anal Gape Training in chastity cage
    10:24
    Anal Gape Training in chastity cage
    Selfspanker
    947 views
    Training my hole so deep I love it
    05:56
    Training my hole so deep I love it
    Qiyizhongzi
    8K views
    Fucked by huge, hard cock until i reach a sissygasm
    05:31
    Fucked by huge, hard cock until i reach a sissygasm
    Michael Freeman
    1.7K views
    Cum and Squirt from Anal Dildo Riding
    07:46
    Cum and Squirt from Anal Dildo Riding
    FapHouse
    659 views
    Prison of Sissy 5 - Adam Is Training to Become a Sissy... the Prison Boss Got a Blowjob
    15:38
    Prison of Sissy 5 - Adam Is Training to Become a Sissy... the Prison Boss Got a Blowjob
    Johannesgaming
    1.1K views
    Black Cock Jerking Off Big Load While Cumming & Moaning (Dirty Talking) (Crossdresser) Daddy Shooting A Load (Panty Cum)
    04:31
    Black Cock Jerking Off Big Load While Cumming & Moaning (Dirty Talking) (Crossdresser) Daddy Shooting A Load (Panty Cum)
    Jamdown26
    32.1K views
    Black Guy Jerking Off Black Cock & Wearing Wife Pretty Panty & Nightie (Cumming & Moaning) (Dirty Talking) Shooting Load
    05:21
    Black Guy Jerking Off Black Cock & Wearing Wife Pretty Panty & Nightie (Cumming & Moaning) (Dirty Talking) Shooting Load
    Jamdown26
    11.1K views
    Just a Gaping Hole Ft David Anderson
    08:08
    Just a Gaping Hole Ft David Anderson
    Dirty David
    11.7K views
    This is what it looks like when I unleash the slut inside me.
    14:44
    This is what it looks like when I unleash the slut inside me.
    Michael Freeman
    1.4K views
    Sissy Wearing Tartan Riding Dildos
    09:50
    Sissy Wearing Tartan Riding Dildos
    Snuskis80
    4.1K views
    Sissy Playing With Some Dildos
    04:53
    Sissy Playing With Some Dildos
    Snuskis80
    772 views
    Sissy In Blue Riding Her Dildos
    03:55
    Sissy In Blue Riding Her Dildos
    Snuskis80
    582 views
    Sissy Playing With A Black Dildo
    07:16
    Sissy Playing With A Black Dildo
    Snuskis80
    8.2K views
    Obedience Training - Body and Muscle Worship
    12:19
    Obedience Training - Body and Muscle Worship
    linktree
    11.6K views
    Anal Training In Chastity Cage
    06:05
    Anal Training In Chastity Cage
    Selfspanker
    569 views
    Boots Lick Training for Mistress Asura
    01:13
    Boots Lick Training for Mistress Asura
    Sissyemilynutte
    5.7K views
    Training
    01:06
    Training
    Bound_Sissy
    624 views
    Hard Self Spanking On Hairy Ass While Wearing Chastity Cage
    15:06
    Hard Self Spanking On Hairy Ass While Wearing Chastity Cage
    Selfspanker
    3K views
    A little femboy stretches his ass and receives a double anal penetration
    03:02
    A little femboy stretches his ass and receives a double anal penetration
    Kamizila
    948 views
    Sissy Riding Her Favorite Dildo
    04:50
    Sissy Riding Her Favorite Dildo
    Snuskis80
    7.9K views
    Power bottom pleasantly torments cock with mouth!
    05:34
    Power bottom pleasantly torments cock with mouth!
    staxus
    22.4K views
    Femboy Sounding in Chastity
    09:44
    Femboy Sounding in Chastity
    FapHouse
    12.1K views
    I think someone here likes to tease men, don't you think?
    05:08
    I think someone here likes to tease men, don't you think?
    Michael Freeman
    530 views
    White High Heels And A Black Dildo
    05:23
    White High Heels And A Black Dildo
    Snuskis80
    3.1K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Train

    • Sissy Feminization
    • Treat Me Like a Woman
    • Twink Trainer
    • Feminized and Fucked
    • Femboy Training
    • P Train
    • White CD BBC
    • Cute Feminine Boys
    • Slut Destroyed
    • Boy to Girl Transformation
    • Dirty Talk English Subtitles
    • Sissification
    • Crossing the Line
    • Chaste Boi
    • 10 Loads in 1 Dumpster
    • Black Sex Digital
    • Faggot Brainwashing
    • Beautiful XXX
    • Secret Sissyboy
    • First Time Wearing Women's Panties
    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