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 Crossdresser And Mistress Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    You switched to shemale orientation. Do you want to keep searching in the gay section?
    Crossdresser
    Sissy
    Mistress
    Sissy Crossdresser
    Sissy Mistress
    Sissy Training
    Amateur Crossdresser
    Mature Crossdresser
    Crossdresser Fucked
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Sissy Slave
    Amateur Sissy
    Crossdresser Blowjob
    Sissy Blowjob
    Best Videos
    By clicking the content you will also see an ad. AD
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.6M views
    Dominant crossdresser and British MILF on the fucking machine
    13:16
    Dominant crossdresser and British MILF on the fucking machine
    Spike Essex
    5.6K views
    Male to female gender transformation smoking whore
    16:00
    Male to female gender transformation smoking whore
    684.1K views
    Mistress Pegs Emo Crossdresser and Makes Her Swallow Cum
    00:29
    Mistress Pegs Emo Crossdresser and Makes Her Swallow Cum
    Bailey Wilde
    4K views
    shemale dresses sissy to fuck
    16:14
    shemale dresses sissy to fuck
    2M views
    Sissy Lucy gets tied teased and tickled by femdom MILF Lisa and Mistress Jodie May
    06:39
    Sissy Lucy gets tied teased and tickled by femdom MILF Lisa and Mistress Jodie May
    Spike Essex
    41.1K views
    Feminized for Girls Night Out (Full Movie)
    23:39
    Feminized for Girls Night Out (Full Movie)
    Bailey Wilde
    544.8K views
    Crossdresser gay tranny in wide leg bootcut flare jeans and crop top and high heels dancing for his master and mistress
    04:12
    Crossdresser gay tranny in wide leg bootcut flare jeans and crop top and high heels dancing for his master and mistress
    Lakshmi Trans
    10.5K views
    family fun 1.mp4
    13:05
    family fun 1.mp4
    1.7M views
    How a Sissy should Masturbate - Sissy Watching Hypno - Crossdresser slut - Chastity with Vibrator - Sissy Joanna
    06:55
    How a Sissy should Masturbate - Sissy Watching Hypno - Crossdresser slut - Chastity with Vibrator - Sissy Joanna
    Joanna CD
    18K views
    Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    284.4K views
    Sissy Crossdresser Pussy Tease
    00:52
    Sissy Crossdresser Pussy Tease
    littlemissbrat
    31.3K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.1M views
    A sissy crossdresser likes to lick mistress ass
    00:23
    A sissy crossdresser likes to lick mistress ass
    14K views
    Degraded and bound Alina learns that her pleasure is on the secon place during exhausting bdsm session
    11:20
    Degraded and bound Alina learns that her pleasure is on the secon place during exhausting bdsm session
    alinanightsky
    301.3K views
    Swallow My Cum
    15:15
    Swallow My Cum
    TSRyley
    240.6K views
    Many crossdressers fucked scrnrs
    01:09:02
    Many crossdressers fucked scrnrs
    1.4M views
    extreme masturbation
    11:11
    extreme masturbation
    TSquennAna
    141.5K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    1.8M views
    Arab Femboy Fucked Anal With Cucumber
    05:07
    Arab Femboy Fucked Anal With Cucumber
    SmolBoimimi
    96.2K views
    Submissive arab crossdresser
    39:32
    Submissive arab crossdresser
    1.5M views
    What Stepmommy Wants
    08:12
    What Stepmommy Wants
    Cassandra Lovit
    5.9K views
    I finally let my stepsis fuck my trans pussy
    05:30
    I finally let my stepsis fuck my trans pussy
    CutePinkUnicorn
    598.5K views
    Trans and TV CD Fuckfest
    11:12
    Trans and TV CD Fuckfest
    Mistress Jodie May
    92.8K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    The Interrogation
    05:11
    The Interrogation
    Cassandra Lovit
    9.5K views
    2 Mommies Training Their TS Slut - Lucy Hart - Penny Barber - Mira Maven
    15:07
    2 Mommies Training Their TS Slut - Lucy Hart - Penny Barber - Mira Maven
    Lucy Hart
    366.4K views
    Mistress Sucks off Sissy Jessica Bloom And Spits Cum into Her Own Mouth
    07:15
    Mistress Sucks off Sissy Jessica Bloom And Spits Cum into Her Own Mouth
    Jessica Bloom
    68.5K views
    Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor
    05:03
    Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor
    alinanightsky
    400.7K views
    The latex sex doll suck and fucked by mistress
    02:26
    The latex sex doll suck and fucked by mistress
    Emmy Angeles
    62.3K views
    Black tgirl with giant tool fucking a white ass fat faggot
    11:38
    Black tgirl with giant tool fucking a white ass fat faggot
    Latina Tranny
    1.5M views
    Sissy Trainning by Mistress Kira
    04:17
    Sissy Trainning by Mistress Kira
    Lola Spais
    78.8K views
    Feminization of a Bad Roommate (Full Movie)
    50:07
    Feminization of a Bad Roommate (Full Movie)
    Bailey Wilde
    100.1K views
    Sissy training for your feminization
    03:56
    Sissy training for your feminization
    Allmylinks
    18.2K views
    Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
    18:27
    Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
    Vane03_siss
    204.5K views
    For My Return and Fuck Me My Little Anal Pussy Thoroughly Like the Good Slut I Am
    09:39
    For My Return and Fuck Me My Little Anal Pussy Thoroughly Like the Good Slut I Am
    Nady-So
    8.8K views
    Goodnight, Daniella
    22:23
    Goodnight, Daniella
    320.1K views
    Feminization JOI & Mistress DOM
    03:54
    Feminization JOI & Mistress DOM
    Kymmy Harper
    318.9K views
    Sissy Doll Fucking in a Pegging Date
    07:00
    Sissy Doll Fucking in a Pegging Date
    Brat Perversions
    13.8K views
    Trans Dom in Latex cei & joi
    14:01
    Trans Dom in Latex cei & joi
    Kymmy Harper
    140.2K views
    Trans Girl Tied and Teased
    06:46
    Trans Girl Tied and Teased
    Mistress Jodie May
    127.5K views
    Femboy Mistress Rimjob Facesitting
    02:11
    Femboy Mistress Rimjob Facesitting
    Sayuki
    305K views
    Guy Feminized and Fucked by Roommate (Full Movie)
    01:04:48
    Guy Feminized and Fucked by Roommate (Full Movie)
    Bailey Wilde
    104.5K views
    Daddy come play with me! 🥺
    07:29
    Daddy come play with me! 🥺
    Madelyn Emery
    68K views
    Sissy Joyce - A real life sissy slave
    01:16
    Sissy Joyce - A real life sissy slave
    Sissy Joyce
    680.5K views
    Mesmeriza 23 01 Mov Cinema Clip
    10:55
    Mesmeriza 23 01 Mov Cinema Clip
    Mesmeriza
    68.2K views
    Black Sissy Cuckold Husband Fucked by Wife's BWC White Bull Interracial
    10:32
    Black Sissy Cuckold Husband Fucked by Wife's BWC White Bull Interracial
    Fiona Fortune
    82.1K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Crossdresser And Mistress

    • Crossdressing Husband Caught by Wife
    • Sissy Femdom Humiliation Bisexual
    • Real Sexy Feminine Crossdresser
    • Made to Crossdress and Suck Cock
    • Crossdressers in Pretty Dresses
    • Femboy Domination
    • Men Dressed as Woman
    • Secret Sissyboy
    • Cross Dresser Fucked
    • Crossboy With Mommy Clothes
    • Feminization Bondage
    • Mistress Cuckolding Slave
    • Sissys Get Blacked
    • Sissy-Virgin
    • Crossdreser Sex
    • Crossdresserlover Ladyboys
    • Crossdressing Husband
    • Sissyslut
    • Shemale Sissification
    • Feminized

    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