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

    Cuckold Anal Training Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    SissyTask-Steel Clothes from neighbours and daily anal training
    11:16
    SissyTask-Steel Clothes from neighbours and daily anal training
    SissyDaniella
    3.6K views
    Sissy anal training
    08:21
    Sissy anal training
    FumikoKatt
    4.5K views
    Sissy anal training
    03:52
    Sissy anal training
    Sissyemilynutte
    1.6K views
    Sissy anal training part 2
    01:44
    Sissy anal training part 2
    FumikoKatt
    2.1K views
    Deeper Anal Training of a Femboy
    02:27
    Deeper Anal Training of a Femboy
    NAT0NYA
    2.2K views
    sissy Cuckold SLUT training
    05:15
    sissy Cuckold SLUT training
    164.8K views
    Slut Beril Who Trains At Home Goes For A Walk Outside Public +18 Coward
    05:07
    Slut Beril Who Trains At Home Goes For A Walk Outside Public +18 Coward
    Usaberilx
    15.2K views
    Come cum inside me black daddy
    01:16
    Come cum inside me black daddy
    Dirtysissywhore
    108.4K views
    Transsexual training - bukkake gokkun! Shemale anal fuck orgy 3
    37:55
    Transsexual training - bukkake gokkun! Shemale anal fuck orgy 3
    EAGLE_GLOBAL
    90.5K views
    Caged Sissy try get pleasure by anal dildo play
    11:54
    Caged Sissy try get pleasure by anal dildo play
    SissyDaniella
    30.5K views
    Sissy coming home from work
    16:12
    Sissy coming home from work
    SissyDaniella
    20K views
    Sissy fucking new pussy hole
    15:06
    Sissy fucking new pussy hole
    SissyDaniella
    12.3K views
    Sissy Intro at home and pleasing BBC Dildo
    13:05
    Sissy Intro at home and pleasing BBC Dildo
    SissyDaniella
    14.1K views
    Horny Sissy on Way Home
    14:02
    Horny Sissy on Way Home
    SissyDaniella
    12.3K views
    Sissy in Red playing with Sex Maschine
    12:40
    Sissy in Red playing with Sex Maschine
    SissyDaniella
    5.6K views
    Sissy get fucked by sex maschine on table again.png
    11:00
    Sissy get fucked by sex maschine on table again.png
    SissyDaniella
    3.8K views
    Sissy Compiliation
    12:49
    Sissy Compiliation
    SissyDaniella
    6.7K views
    Sissy Affirmation - learning my place
    02:15
    Sissy Affirmation - learning my place
    T TorontoBoyToy
    10.7K views
    Woman Puts Nails on Crossdresser
    05:02
    Woman Puts Nails on Crossdresser
    Bailey Wilde
    2.8K views
    Sissy dildo riding compilation
    10:34
    Sissy dildo riding compilation
    SissyDaniella
    12.1K views

    Relevant Short videos

    Preggo sissy slut wants to be fucked
    Preggo sissy slut wants to be fucked
    cheapslutfemke
    3.4K views
    Captivating moment from "Sissy get fucked by sex maschine on table again.png"
    Captivating moment from "Sissy get fucked by sex maschine on table again.png"
    SissyDaniella
    694 views
    Black Cuckold Sissy Gets Fucked by Wife's Lover
    Black Cuckold Sissy Gets Fucked by Wife's Lover
    Fiona Fortune
    1.9K views
    Spectacular moment from "Woman Puts Nails on Crossdresser"
    Spectacular moment from "Woman Puts Nails on Crossdresser"
    Bailey Wilde
    508 views
    Sonechka Stretches Her Anal Cunt for Future Fuckers
    Sonechka Stretches Her Anal Cunt for Future Fuckers
    Sonechka25
    593 views
    Unforgettable moment from "Sissy serving dominant hotwife mistress in video call PART 1"
    Unforgettable moment from "Sissy serving dominant hotwife mistress in video call PART 1"
    SissySimran
    644 views
    Sissy Compilation Chastity Forever
    12:54
    Sissy Compilation Chastity Forever
    SissyDaniella
    1.8K views
    Sissy exposing in public and playing with dildo
    07:55
    Sissy exposing in public and playing with dildo
    SissyDaniella
    11.7K views
    Horse cock in big white virgin asshole, first try, lubed and ready, but still virgin pussy is tight but juicy
    06:02
    Horse cock in big white virgin asshole, first try, lubed and ready, but still virgin pussy is tight but juicy
    21K views
    Ashley, a very slutty Mexican queer, is fucked by a huge black dildo
    06:05
    Ashley, a very slutty Mexican queer, is fucked by a huge black dildo
    Vkta77
    10.4K views
    Sissy serving dominant hotwife mistress in video call PART 1
    19:15
    Sissy serving dominant hotwife mistress in video call PART 1
    SissySimran
    20.6K views
    Sissy teasing and dildo riding on balcony
    15:21
    Sissy teasing and dildo riding on balcony
    SissyDaniella
    2.2K views
    Mesmeriza Compilation 12 Island of Oblivion
    12:10
    Mesmeriza Compilation 12 Island of Oblivion
    Mesmeriza
    3.8K views
    Sissy Intro at home and pleasing BBC Dildo 2
    06:04
    Sissy Intro at home and pleasing BBC Dildo 2
    SissyDaniella
    3.2K views
    Sissy anal table joi
    13:53
    Sissy anal table joi
    SissyDaniella
    8.3K views
    Locked Latex Sissy inflates plug to massage prostate
    01:03
    Locked Latex Sissy inflates plug to massage prostate
    Sissy Sidney
    12.3K views
    Jasmine cums hard dressed up as Snow White
    01:20
    Jasmine cums hard dressed up as Snow White
    Jasmine904x
    2K views
    Sissy frisky fucking BBC Dildo in Public Garage & Wasch Maschine
    06:30
    Sissy frisky fucking BBC Dildo in Public Garage & Wasch Maschine
    SissyDaniella
    9.7K views
    Sonechka Stretches Her Anal Cunt for Future Fuckers
    03:17
    Sonechka Stretches Her Anal Cunt for Future Fuckers
    Sonechka25
    1.8K views
    Sissy dildo riding outside
    11:07
    Sissy dildo riding outside
    SissyDaniella
    16.7K views
    Sissy in Red Dress and black Dildo ride
    05:27
    Sissy in Red Dress and black Dildo ride
    SissyDaniella
    12.3K views
    Sissy Baby prepares for Chastity and Pampering
    00:28
    Sissy Baby prepares for Chastity and Pampering
    M MommyOwnsMe
    10.4K views
    sissyeric crossdresser dildo training
    04:51
    sissyeric crossdresser dildo training
    4.3K views
    Sissy alone at home with Dildo
    14:37
    Sissy alone at home with Dildo
    SissyDaniella
    6.4K views
    Throne of Sissy Pleasures
    01:29
    Throne of Sissy Pleasures
    Sissy Slut Masha
    1K views
    Sissy Training 2
    13:08
    Sissy Training 2
    Z ZZ4
    3.3K views
    Sissy ass to mouth play with butt plug
    05:43
    Sissy ass to mouth play with butt plug
    SissySimran
    2.3K views
    Sissy training
    16:05
    Sissy training
    SissySimran
    11.9K views
    Brazilian cuck instructed to play with dildo and vibrator
    11:00
    Brazilian cuck instructed to play with dildo and vibrator
    Assexploringmachin
    1.9K views
    Sissy riding dildo in e appartment
    17:45
    Sissy riding dildo in e appartment
    SissyDaniella
    3.7K views
    Tunnel Plug  Sissy
    00:16
    Tunnel Plug Sissy
    ChastitySissyClit
    2.3K views
    Sissy dildo fuck training session 29
    09:50
    Sissy dildo fuck training session 29
    Assexploringmachin
    1.3K views
    Between the Lines & Between My Legs
    14:17
    Between the Lines & Between My Legs
    Gray Perrier
    88.5K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    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