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

    Crossdressing Fantasy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Turned Crossdressing Cuckold
    Crossdressing Nylon Cock
    Crossdressing Skirt Masturbation
    Crossdressing Bridal Lingerie
    Crossdressing With Toys
    Crossdressing Feeling Girly
    Crossdressing the Couch
    Crossdressing Truck Driver
    Desi Tamil Crossdressing
    Crossdressing Velma Cosplay
    Crossdressing Stretching Anal
    Crossdressing Husband Videos
    Crossdressing Bondage Slut
    Crossdressing Boy to Girl
    Girlfriend Catches Me Crossdressing
    Slutty Nasty Crossdressing Gurl
    Crossdressing Sissy Faggot Transvestite
    Sissy Fantasies Crossdresser Captions
    Sissy Caught Crossdressing Hotel
    Caught Crossdressing Pegging Punishment
    Best Videos
    By clicking the content you will also see an ad. AD
    My stepbrother fucks my ass in the kitchen. Part 1
    10:06
    My stepbrother fucks my ass in the kitchen. Part 1
    PalmasRecordsMen
    429.3K views
    Crossdress cosplay as a sailor and get fucked
    10:05
    Crossdress cosplay as a sailor and get fucked
    WanidaCrossdresser
    48.1K views
    Tgirl gets Fucked in Anal while talking to a barmaid
    19:04
    Tgirl gets Fucked in Anal while talking to a barmaid
    MySchoolLife
    670.5K views
    Sissy Training for Hotel Housekeeping Job
    12:49
    Sissy Training for Hotel Housekeeping Job
    Bailey Wilde
    76.2K views
    Our first night as husband and wife
    06:55
    Our first night as husband and wife
    P PoloBigWin
    13.1K views
    Mommy Holy - JOI - Dinky Gets Attention - lots of Mommy talk
    06:41
    Mommy Holy - JOI - Dinky Gets Attention - lots of Mommy talk
    Holy
    18.8K views
    I had a big cumshot in unkown hotel
    05:39
    I had a big cumshot in unkown hotel
    Samantha Sissy World
    1.5M views
    Role Play JOI - Waiting for Daddy to Worship my Asshole FULL VID ON LAYNELOVEE MANYVIDS
    01:14
    Role Play JOI - Waiting for Daddy to Worship my Asshole FULL VID ON LAYNELOVEE MANYVIDS
    Layne Love
    55.2K views
    Transformed into Sissy Maid to Get Job
    12:49
    Transformed into Sissy Maid to Get Job
    Bailey Wilde
    151.5K views
    Sexy Shemale Secretary Opens Her Big Ass in the Bathroom of a Gas Station
    07:19
    Sexy Shemale Secretary Opens Her Big Ass in the Bathroom of a Gas Station
    fermerino
    9K views
    BNWO Snowbunny Party Costume Humiliation
    11:11
    BNWO Snowbunny Party Costume Humiliation
    Natalie Napoli
    11.7K views
    Roleplay crossdresser sissy get fucked
    01:28
    Roleplay crossdresser sissy get fucked
    Sebnem
    292.6K views
    Nancy is Becoming stepDaddy's Perfect Sissy Slut
    07:07
    Nancy is Becoming stepDaddy's Perfect Sissy Slut
    Nancy Rose
    1.9K views
    Naughty Wife 5
    07:21
    Naughty Wife 5
    Tina Samantha West
    56.9K views
    Fuck me in an office uniform, I'm your boss.
    12:37
    Fuck me in an office uniform, I'm your boss.
    WanidaCrossdresser
    33K views
    Jessica Bloom Edges Her Hard Cock And Begs For Your Dick - Dildo Riding Anal Orgasm
    07:17
    Jessica Bloom Edges Her Hard Cock And Begs For Your Dick - Dildo Riding Anal Orgasm
    Jessica Bloom
    56.1K views
    Sissification and Fucked for Job
    03:04
    Sissification and Fucked for Job
    Bailey Wilde
    89.3K views
    Tranny Barbie can't take the BBC and tries to get away but he keeps fucking my ass hard - amateur shemale - Candy Ass Sissy
    06:08
    Tranny Barbie can't take the BBC and tries to get away but he keeps fucking my ass hard - amateur shemale - Candy Ass Sissy
    Candy Ass Sissy
    65.5K views
    You Dont Need Your Annoying Girlfriend, Just my Girl Dick And CUM! Trans Roleplay POV Cumshot
    06:10
    You Dont Need Your Annoying Girlfriend, Just my Girl Dick And CUM! Trans Roleplay POV Cumshot
    Jessica Bloom
    39.7K views
    POV Cocksucker Instructions & Cumeating Countdown With Jessica Bloom
    10:29
    POV Cocksucker Instructions & Cumeating Countdown With Jessica Bloom
    Jessica Bloom
    171.7K views
    Trans dresses as teacher, cosplay, wants to play with his students
    05:35
    Trans dresses as teacher, cosplay, wants to play with his students
    Letany Ponny
    231.7K views
    Princess Bunnie: Naughty Maid Sneaks off to Masturbate
    13:04
    Princess Bunnie: Naughty Maid Sneaks off to Masturbate
    Princess Bunnie
    27.1K views
    Step Mommy Trains You How to Be A Sissy Cock Sucker (Humiliation)
    10:07
    Step Mommy Trains You How to Be A Sissy Cock Sucker (Humiliation)
    Jessica Bloom
    187.6K views
    New Year fairy tale about the Disobedient  Sissy girl and Santa that throat fucks the whore, anal and turned into a deer
    01:33
    New Year fairy tale about the Disobedient Sissy girl and Santa that throat fucks the whore, anal and turned into a deer
    alinanightsky
    4.9K views
    Step dad won't pay for my college unless I transform into sissy!
    02:15
    Step dad won't pay for my college unless I transform into sissy!
    Viper Fierce
    143.3K views
    I walk in my silikon body suite with different outfits
    08:58
    I walk in my silikon body suite with different outfits
    Loreleyadd
    5.8K views
    I was went into the wrong bathroom but I didn't care, I wanted a dick.
    06:17
    I was went into the wrong bathroom but I didn't care, I wanted a dick.
    WanidaCrossdresser
    24K views
    Sucking my little sisters boyfriends  big black cock
    08:20
    Sucking my little sisters boyfriends big black cock
    Anna Rios
    46.7K views
    Do you need a Sissy Maid? I clean the house and something else - Veronica Sanders
    05:45
    Do you need a Sissy Maid? I clean the house and something else - Veronica Sanders
    Veronica Sanders
    57.6K views
    Beautiful Blonde Sissy talks dirty and shows you her hard cock inside her satin boi panties
    03:13
    Beautiful Blonde Sissy talks dirty and shows you her hard cock inside her satin boi panties
    Ana Keel
    61.5K views
    Animal Instinct
    00:53
    Animal Instinct
    Twistedrama
    56.6K views
    Naughty naughty
    16:18
    Naughty naughty
    Shelly Robertss
    82.5K views
    Hot trans in sexy pink mini dress teasing
    08:22
    Hot trans in sexy pink mini dress teasing
    CuteCynthia
    19.4K views
    Trainer's Order No25 Anal 3 Outdoors
    15:45
    Trainer's Order No25 Anal 3 Outdoors
    megu2002
    8.4K views
    Ultra gay sissy faggot begs Daddy
    02:17
    Ultra gay sissy faggot begs Daddy
    JessicaLynn15
    74.9K views
    Sexy Satin Secretary Seals the Deal
    05:06
    Sexy Satin Secretary Seals the Deal
    KittyKaash
    82.9K views
    Streetwalker Roleplay
    06:39
    Streetwalker Roleplay
    Mistress Jodie May
    126.2K views
    POV me begging a stranger for a date
    06:30
    POV me begging a stranger for a date
    JessicaLynn15
    7.6K views
    Wife and Neighbour
    03:21
    Wife and Neighbour
    Tina Samantha West
    46.4K views
    Famous Japanese Crossdresser steal the scene of real sex at a Motel
    05:23
    Famous Japanese Crossdresser steal the scene of real sex at a Motel
    Haru
    195.7K views
    Naughty Wife with Chris again
    05:08
    Naughty Wife with Chris again
    Tina Samantha West
    16.1K views
    Your Sissy Destiny - Sissification Encouragement Affirmation
    01:47
    Your Sissy Destiny - Sissification Encouragement Affirmation
    Layne Love
    27.6K views
    Please come to my room so we can enjoy the inside and fuck so hard
    32:14
    Please come to my room so we can enjoy the inside and fuck so hard
    Reynaldo6
    36.3K views
    Naked under the dirndl
    02:33
    Naked under the dirndl
    CarinaDavid
    7.2K views
    Coach BBC Reconnects to Cum Breed My Ass After Seeing My Vids on Twitter - Camera 1 - Candy Ass Sissy
    06:36
    Coach BBC Reconnects to Cum Breed My Ass After Seeing My Vids on Twitter - Camera 1 - Candy Ass Sissy
    Candy Ass Sissy
    48.5K views
    Public Pissing on Sissy Slut
    01:44
    Public Pissing on Sissy Slut
    FrinaXXX
    10.5K views
    Horny Sissy For Halloween - Extended Preview
    02:53
    Horny Sissy For Halloween - Extended Preview
    Holland Of Chicago
    39.5K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Crossdressing Fantasy

    • Crossdress Halloween Costume
    • Sissys Get Blacked
    • Bisexual Creampie Orgy
    • Bodystocking
    • Roleplay
    • Cross Dresser Cum
    • Fashion Show Nude
    • Inverted Chastity
    • Vintage Transvestite Movies
    • Schoolgirl Uniform
    • Slutwife Secrets
    • Gorgeous Femboy
    • Feminize Yourself
    • British Bareback
    • Boy Becomes Girl
    • The Sissy's Future
    • Goth CD
    • Sissysubkrystal
    • Fishnets
    • Sissyslut

    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