PornPorn Transgender • 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
    • Amateur
    • Shemale Fucks Guy
    • Shemale Fucks Girl
    • Big Cock
    • All categories
    Live Sex
    Categories
    • Shemale Fucks Guy
    • Black
    • Big Cock
    • 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
    LET IT SNOW, LET IT SAVE! ☃️ Faphouse Discounts – Winter Edition
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Black
    • Big Cock
    • Shemale Fucks Shemale
    • Amateur
    • Sissy
    • Shemale Fucks Girl
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Big Black Cock
    • Cum In Mouth
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Crossdressing Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Skinny crossdressing sissy cum dump
    05:47
    Skinny crossdressing sissy cum dump
    Skinnyminxx_xd
    868.3K views
    Skinny crossdressing sissy bareback
    07:20
    Skinny crossdressing sissy bareback
    Skinnyminxx_xd
    204.6K views
    Public Crossdressing... Sissy in very short dresses outside
    05:07
    Public Crossdressing... Sissy in very short dresses outside
    19.4K views
    Sexy Mature Crossdressing sissy slut Takes It Deep
    23:51
    Sexy Mature Crossdressing sissy slut Takes It Deep
    Shystockings
    2K views
    Crossdressing sissy tanyacdmodel in white lingerie masturbating
    04:23
    Crossdressing sissy tanyacdmodel in white lingerie masturbating
    Tanyacdmodel
    7.5K views
    Sexy Mature Crossdressing Sissy Slut in yellow lingerie and limp dick in chastity rides some of her dildos
    07:05
    Sexy Mature Crossdressing Sissy Slut in yellow lingerie and limp dick in chastity rides some of her dildos
    Shystockings
    4.5K views
    Mature Crossdressing sissy slut getting fucked by sex machine
    05:21
    Mature Crossdressing sissy slut getting fucked by sex machine
    Shystockings
    2.8K views
    Crossdressing sissy nikki blows on dildo
    05:00
    Crossdressing sissy nikki blows on dildo
    Skinnyminxx_xd
    29K views
    Sexy Mature limp dick Crossdressing sissy slut removes large butt plug and rides hand dildo
    06:31
    Sexy Mature limp dick Crossdressing sissy slut removes large butt plug and rides hand dildo
    Shystockings
    2.4K views
    Crossdressing Sissy Gina Wanking, Pissing, Posing and Cumming
    12:15
    Crossdressing Sissy Gina Wanking, Pissing, Posing and Cumming
    Ginaxtgirl
    1.9K views
    Mature Crossdressing Sissy Slut Wanking a Perthetic Limp Cock
    03:19
    Mature Crossdressing Sissy Slut Wanking a Perthetic Limp Cock
    Shystockings
    1.4K views
    Mature Crossdressing Sissy Slut Dildo Training
    14:10
    Mature Crossdressing Sissy Slut Dildo Training
    Shystockings
    8.5K views
    Crossdressing sissy cosplay school swimsuit and fuck herself
    02:50
    Crossdressing sissy cosplay school swimsuit and fuck herself
    Bitchmoe
    7.6K views
    Sexy Mature Crossdressing Sissy Slut
    04:11
    Sexy Mature Crossdressing Sissy Slut
    Shystockings
    1.7K views
    Sexy Mature Crossdressing sissy slut in black body stocking ride black dildo on fucking machine
    07:03
    Sexy Mature Crossdressing sissy slut in black body stocking ride black dildo on fucking machine
    Shystockings
    1.8K views
    Mature Crossdressing Sissy Goth Slut
    02:13
    Mature Crossdressing Sissy Goth Slut
    Shystockings
    1.2K views
    Crossdressing sissy in stockings riding dildo cums hard from anal orgasm
    03:18
    Crossdressing sissy in stockings riding dildo cums hard from anal orgasm
    Mysterion
    2.7K views
    crossdressing sissy slut jerking off
    07:52
    crossdressing sissy slut jerking off
    2.8K views
    Crossdressing sissy horny wet pussy
    11:34
    Crossdressing sissy horny wet pussy
    J Jasmine Sub
    1.5K views
    Riding My Toy Crossdressing Sissy
    01:31
    Riding My Toy Crossdressing Sissy
    Sissy_Alice
    749 views
    Crossdressing sissy playing with Sex machine
    07:50
    Crossdressing sissy playing with Sex machine
    Bitchmoe
    41.6K views
    Sissy Anal Training with Fist and Dildo stretching crossdressing sissy Kiraszasissy
    11:17
    Sissy Anal Training with Fist and Dildo stretching crossdressing sissy Kiraszasissy
    KiraszaSissy
    5.6K views
    Solo Crossdressing Sissy Fucking Tight Anal
    05:30
    Solo Crossdressing Sissy Fucking Tight Anal
    Your Toy
    2.7K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    2M views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.2M views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    822K views
    Dating a mature crossdresser
    08:12
    Dating a mature crossdresser
    Pure Ts
    247.1K views
    You Have to See What These Three Trans Women Did with This Hottie After the Party.
    22:24
    You Have to See What These Three Trans Women Did with This Hottie After the Party.
    Tsdanisantos1
    569K views
    Bring Us Holes, Silkbone. or We'll Fuck Yours!
    08:12
    Bring Us Holes, Silkbone. or We'll Fuck Yours!
    Mistress Jodie May
    128.1K views
    She loves to be my favorite fucktoy in bareback
    05:36
    She loves to be my favorite fucktoy in bareback
    MrNastyXavier
    2M views
    Swallow My Cum
    15:15
    Swallow My Cum
    TSRyley
    260K views
    Crossdressing superstar visits the site
    06:40
    Crossdressing superstar visits the site
    Pure Ts
    63.6K views
    Shemale and guy fuck till both cum
    13:31
    Shemale and guy fuck till both cum
    TSLuxylux
    1.9M views
    Submissive Sissy crossdresser fucked by BBC - she is a bitch4
    09:55
    Submissive Sissy crossdresser fucked by BBC - she is a bitch4
    Rozebella
    725.2K views
    Samantha Sass & Tenn Strokes
    08:12
    Samantha Sass & Tenn Strokes
    Pretty She Stick
    73.2K views
    I ended up in this sissy hole. I love fucking and sucking a big dick and showing them what a real blowjob part4
    05:59
    I ended up in this sissy hole. I love fucking and sucking a big dick and showing them what a real blowjob part4
    Rozebella
    171.3K views
    I fuck my roommate and fills my butthole full of cum while i'm in chastity
    05:45
    I fuck my roommate and fills my butthole full of cum while i'm in chastity
    missangell_
    680.2K views
    Her ass can fit all my big black cock so good
    06:21
    Her ass can fit all my big black cock so good
    MrNastyXavier
    1.8M views
    Your little bitch wants hot cum inside her tight and dirty asshole
    06:50
    Your little bitch wants hot cum inside her tight and dirty asshole
    missangell_
    776.1K views
    Big Dick Hot Cumshot Compilation 3 - alizevert
    05:10
    Big Dick Hot Cumshot Compilation 3 - alizevert
    alizevert
    4.9M views
    My Neighbor Fuck Me in Bedroom
    08:12
    My Neighbor Fuck Me in Bedroom
    Emmy Angeles
    346.9K views
    BBC Fucks a Slutty Crossdresser Without Limits
    32:44
    BBC Fucks a Slutty Crossdresser Without Limits
    Trans and Co
    390.1K views
    Roomie likes to fuck my ass til he fill it with cum
    05:59
    Roomie likes to fuck my ass til he fill it with cum
    missangell_
    764.3K views
    Fucking on the last day of summer, in a cornfield
    03:39
    Fucking on the last day of summer, in a cornfield
    vika_sissy
    385.8K views
    Ejaculation collection. Look at me masturbating a lot
    07:54
    Ejaculation collection. Look at me masturbating a lot
    harucoco
    234.1K views
    On My Knees and They Fill My Mouth with Lots of Milk
    14:18
    On My Knees and They Fill My Mouth with Lots of Milk
    Valera Toro
    507.9K views
    Imagine You Are Fucking a Boy!
    06:15
    Imagine You Are Fucking a Boy!
    KinkyHome
    86.4K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Crossdressing Sissy

    • Mature Crossdresser With Straight Guy
    • First Time Crossdressing for Friend
    • Fucking a Sissy Femboy
    • Dirty Crossdressers Slut
    • Crossdress Fucked
    • Boy Dressed as Girl
    • Cross Dressing Faggot
    • Femboys in Lingerie
    • Crossdreser Sex
    • Transvestites Sissies
    • Secret Sissyboy
    • Sissyslut Harley
    • Shemale Miniskirt
    • Tranny Whores
    • Transgender Taboo Porn
    • Very Girly Ladyboys
    • British Bareback
    • Beautiful Dress Trans
    • Sissymeike
    • Caught Wearing Sisters Clothes
    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