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
    • 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
    ICE MELTING SALE — 50% OFF 🧊🔥 Limited-time deal
    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
    • 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
    Little Sissy
    Caged Sissies
    Sissy Instructions
    Sissy Hentai
    Ai Sissy
    Ebony Sissy
    Sissy Bitch
    Fat Sissy
    Indian Sissy
    Sissy CEI
    Sissy Hardcore
    Sissy Handjob
    Femboy Sissy
    Japanese Sissy
    Old Sissy
    Sissy Suck
    Sissy Rough
    Sissy Trap
    Sissy Interracial
    Arab Sissy
    Best Videos
    By clicking the content you will also see an ad. AD
    What Happened Here Was More Than a Fetish, I Fucked a Lot with My Friend, This Naughty Slut
    10:47
    What Happened Here Was More Than a Fetish, I Fucked a Lot with My Friend, This Naughty Slut
    Tsdanisantos1
    90.8K views
    Radroachhd Intense Deepthroat: Hot Big-booty Raven Swallows Cum, Craving a Massive Monster Cock
    02:14
    Radroachhd Intense Deepthroat: Hot Big-booty Raven Swallows Cum, Craving a Massive Monster Cock
    FapHouse
    140.5K views
    Sex before breakfast
    10:32
    Sex before breakfast
    Elwadeoh
    920.3K 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
    318.6K views
    A Show From a Japanese Queen for You
    05:32
    A Show From a Japanese Queen for You
    FapHouse
    173K views
    Date Night with Mature Crossdresser
    08:12
    Date Night with Mature Crossdresser
    Pure Ts
    218.8K views
    She was cumming all on my big dick and kept on riding
    05:25
    She was cumming all on my big dick and kept on riding
    MrNastyXavier
    259.6K views
    tgirl sits and rides on massive dildo - Hankey's Toys XXXCALIBUR
    01:52
    tgirl sits and rides on massive dildo - Hankey's Toys XXXCALIBUR
    amyy_babyy_x
    1M views
    Fuck machine anal orgasm
    03:04
    Fuck machine anal orgasm
    Sissy-boys
    112.2K views
    Horny sissy slut! Nude in public and ass fuck at the swimming lake!
    01:17
    Horny sissy slut! Nude in public and ass fuck at the swimming lake!
    Mydirtyhobby
    106.6K views
    Femboy Fucked by this rascal with a bbc
    23:38
    Femboy Fucked by this rascal with a bbc
    Travsexysensuel
    290.2K views
    Much Sexier Than Most Women
    08:12
    Much Sexier Than Most Women
    Pure Ts
    232.6K views
    A collection of hot trans girl Sasha_Q's orgasms
    05:18
    A collection of hot trans girl Sasha_Q's orgasms
    Sissy_Sasha_Q
    33.3K views
    Big Dick Femboy Cumshot Compilation 4 - alizevert
    07:25
    Big Dick Femboy Cumshot Compilation 4 - alizevert
    alizevert
    910.1K views
    Big Black Ass Pounded In The Backseat By Big Black Cock
    03:10
    Big Black Ass Pounded In The Backseat By Big Black Cock
    Big Dick RJxxx
    238.7K views
    Getting Ready for my man to fuck my Ass Bareback - More on FapHouse, Onlyfans Veronica Sanders
    06:39
    Getting Ready for my man to fuck my Ass Bareback - More on FapHouse, Onlyfans Veronica Sanders
    Onlyfans
    199.7K views
    Asian Femboy goes black..
    05:25
    Asian Femboy goes black..
    Lola Femme
    1.2M views
    She likes the doggy style position because it goes deeper into her dirty ass
    05:22
    She likes the doggy style position because it goes deeper into her dirty ass
    MrNastyXavier
    271.9K views
    Riding dildo on bike in public - caught
    04:05
    Riding dildo on bike in public - caught
    Asiansissypublic
    77.3K views
    POV: Your Life as a Human Urinal - 2 Cumahots
    06:12
    POV: Your Life as a Human Urinal - 2 Cumahots
    FapHouse
    31.7K views
    Big daddy fuck 19 years old sissy
    06:34
    Big daddy fuck 19 years old sissy
    FapHouse
    134.8K views
    Sissy Self Facial and Cum Swallow compilation
    09:52
    Sissy Self Facial and Cum Swallow compilation
    Mariana Taylor
    59.8K views
    A dress, heels and a chastity cage. Trying a huge dildo and cumming in my tights!
    03:09
    A dress, heels and a chastity cage. Trying a huge dildo and cumming in my tights!
    Starlightfemboy
    446.2K views
    Sissy secretary fucked hard bent over the table
    06:50
    Sissy secretary fucked hard bent over the table
    Ashley Roze
    943K views
    Amazing Hot Sex with Shemale Friend! Indian Reality Sex
    32:04
    Amazing Hot Sex with Shemale Friend! Indian Reality Sex
    indianXworld
    6.8M views
    A mature man takes the innocence of an effeminate young transvestite  boy
    05:16
    A mature man takes the innocence of an effeminate young transvestite boy
    MTFXXXVIDS
    27.5K views
    Ass Cunt of a Slut
    11:10
    Ass Cunt of a Slut
    Martinatrans85
    144.6K views
    Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
    44:10
    Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
    alinanightsky
    244.2K views
    Big load from femcock Monstercock from a cute girl
    00:58
    Big load from femcock Monstercock from a cute girl
    fansly
    655.8K views
    Watch Transgirl Ria Bentley Fuck Her 9" Bull on Their First Date
    07:07
    Watch Transgirl Ria Bentley Fuck Her 9" Bull on Their First Date
    Ria_Bentley
    582.5K views
    Rubbing My Feet on the Guy's Cock and Licking My Feet and Sucking His Cock (foot Fetish) Creamy Cock. (valeria Toro)
    16:07
    Rubbing My Feet on the Guy's Cock and Licking My Feet and Sucking His Cock (foot Fetish) Creamy Cock. (valeria Toro)
    FapHouse
    101.2K views
    Masturbation Time
    22:58
    Masturbation Time
    Roni Swallows
    75.7K views
    Thai-Malaysian student cosplay EP2: SisK suck Reina
    06:28
    Thai-Malaysian student cosplay EP2: SisK suck Reina
    FapHouse
    1.4M views
    Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune
    13:12
    Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune
    Fiona Fortune
    222.9K views
    BF demolishes my young femboy bussy (2025 Remaster)
    12:36
    BF demolishes my young femboy bussy (2025 Remaster)
    Prettyboi2000x
    81.9K views
    Stepdaddy fuck trans 20yo stepdaughter
    08:53
    Stepdaddy fuck trans 20yo stepdaughter
    FapHouse
    375.1K views
    Tranny dominates you at work
    07:05
    Tranny dominates you at work
    Kymmy Harper
    715.4K views
    extreme masturbation
    11:11
    extreme masturbation
    FapHouse
    163K views
    I love to ride your dick hard like a good bitch
    05:19
    I love to ride your dick hard like a good bitch
    missangell_
    246.7K views
    Wife Videos Sissy Cuckol Being Fucked By Crossdressing stran
    02:44
    Wife Videos Sissy Cuckol Being Fucked By Crossdressing stran
    500.2K views
    Going Outside to ask a guy to let me give him a blowjob (English subtitles)
    05:39
    Going Outside to ask a guy to let me give him a blowjob (English subtitles)
    Onlyfans
    631.2K views
    Jerk Off For Your Hot Trans Friend
    05:49
    Jerk Off For Your Hot Trans Friend
    FapHouse
    29.3K views
    This little bitch knows how to ride a big cock like mine.
    07:28
    This little bitch knows how to ride a big cock like mine.
    MrNastyXavier
    188.5K views
    Mature Trans Gets Fucked by a Black Guy
    36:38
    Mature Trans Gets Fucked by a Black Guy
    FapHouse
    370.1K views
    My stepbrother fucks my ass in the kitchen. Part 1
    10:06
    My stepbrother fucks my ass in the kitchen. Part 1
    FapHouse
    467K views
    Threesome of young trans with a hung BBC cock
    07:31
    Threesome of young trans with a hung BBC cock
    FapHouse
    217.1K views
    What Stepmommy Wants
    08:12
    What Stepmommy Wants
    Cassandra Lovit
    13.9K views
    • Back
    • 1
    • ...
    • 4
    • 5
    • 6
    • 7
    • 8
    • ...
    • 80
    • Next

    Searches Related to Crossdressing Sissy

    • Feminine Guys
    • Uncontrollable Intense Shaking Orgasm
    • Flip Siss
    • Shemale Leggings
    • Slutwife Secrets
    • Bisexual Domination
    • When She Bigger Than You
    • Granny Striptease
    • Female Mask
    • Sissynikki
    • Sub Tranny
    • 2 Sissies Playing
    • Lolla-Sissy
    • Sloppy Toppy
    • Sissybi Anal Huge Dildo
    • Tgirl Finishes Him off Top
    • Japanese Uncensored
    • Cum Hungry Cds
    • Accidentally Cumming
    • Virginie Crossdesir
    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