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 Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Crossdresser
    Sissy
    Sissy Crossdresser Fucked
    Sissy Crossdresser Slut
    Sissy Crossdresser Blowjob
    Amateur Sissy Crossdresser
    Sissy Crossdresser BBC
    Sissy Crossdresser Gangbang
    Sissy Crossdresser Husband
    Sissy Crossdresser Compilation
    Old Sissy Crossdresser
    Asian Sissy Crossdresser
    Verbal Sissy Crossdresser
    Cute Sissy Crossdresser
    Sissy Crossdresser Training
    Humiliated Sissy Crossdresser
    Sissy Crossdresser Solo
    Sissy Crossdresser Faggot
    Sissy Crossdresser Cuckold
    Pegging Sissy Crossdresser
    Best Videos
    By clicking the content you will also see an ad. AD
    SPB Fan Ramble 6-ish
    25:05
    SPB Fan Ramble 6-ish
    Mistress Jodie May
    28.1K views
    Sugardaddy Suck my Sissy Hard Cock
    08:57
    Sugardaddy Suck my Sissy Hard Cock
    Cditalia
    56.7K views
    Sissy Sex Slave
    07:00
    Sissy Sex Slave
    Kapri Sun
    40.8K views
    space_emma cumpilation, femboy, twink, sissy, ruined orgasm and a lot of cum
    03:15
    space_emma cumpilation, femboy, twink, sissy, ruined orgasm and a lot of cum
    space_emma
    24.3K views
    Neighbor Fills Me with Milk
    15:38
    Neighbor Fills Me with Milk
    Valera Toro
    71.1K views
    Mature couple tease tattoo sissy Charlotte with a dildo and magic wand vibrator
    13:27
    Mature couple tease tattoo sissy Charlotte with a dildo and magic wand vibrator
    Spike Essex
    8K views
    Big Ass Trans Latina Sucking and Getting Fucked - Compilation 3
    08:12
    Big Ass Trans Latina Sucking and Getting Fucked - Compilation 3
    Bailey Wilde
    35.4K views
    POV: You are fucking me!!
    07:02
    POV: You are fucking me!!
    Sexy Luke
    24.7K views
    Sissy Self Facial and Cum Swallow compilation
    09:52
    Sissy Self Facial and Cum Swallow compilation
    Mariana Taylor
    45.9K views
    The sissy slut gets cum in her throat during deepthroating and humiliation
    02:05
    The sissy slut gets cum in her throat during deepthroating and humiliation
    alinanightsky
    189.9K views
    Playing with my uncut cock
    02:30
    Playing with my uncut cock
    Olivia-H
    69.3K views
    Transform-process in a hotel in Berlin
    18:02
    Transform-process in a hotel in Berlin
    devdwt_7x_47nrw
    63.3K views
    Double Fuck for Sissy Hole
    08:58
    Double Fuck for Sissy Hole
    FrinaXXX
    4.4K views
    Total Sissy Amnesia
    13:20
    Total Sissy Amnesia
    Natalie Napoli
    23.2K views
    He can't resist digging deep in this creamy tight pussy
    05:55
    He can't resist digging deep in this creamy tight pussy
    missangell_
    110.6K views
    Huge Cock TGirl Lucy anal fucking sexy MILF Lisa
    11:25
    Huge Cock TGirl Lucy anal fucking sexy MILF Lisa
    Spike Essex
    128.6K views
    Being Both #52-#54 Cumpilation
    08:12
    Being Both #52-#54 Cumpilation
    Being Both
    18.8K views
    Warm and creamy
    04:23
    Warm and creamy
    Marcela Cdslut
    89.8K views
    Big ass crossdresser moans while drilled & gaped by trucker
    03:31
    Big ass crossdresser moans while drilled & gaped by trucker
    108.9K views
    Big Anal Pounding for a Sissy on the Couch
    13:29
    Big Anal Pounding for a Sissy on the Couch
    Trans and Co
    37.7K views
    I Heard You Might be Gay
    12:51
    I Heard You Might be Gay
    Natalie Napoli
    139.5K views
    2 sissy latex nurses getting pegged in Chastity by MILF Lisa
    11:47
    2 sissy latex nurses getting pegged in Chastity by MILF Lisa
    Lisa Essex
    116.6K views
    Anal Dildo Blowjob and Cum
    05:02
    Anal Dildo Blowjob and Cum
    Alexalovesit
    1.2K views
    Coffee break
    10:19
    Coffee break
    g geraldinelonginlove
    52.8K views
    VERY oily Watch me CUM 2 times huge SHE-COCK sexy Tiffany Kitten HOT Tgirl CD
    10:01
    VERY oily Watch me CUM 2 times huge SHE-COCK sexy Tiffany Kitten HOT Tgirl CD
    Tiffany Kitten
    7.9K views
    Femboy Fucking Redhead Trans Woman Raw - Compilation 4
    08:12
    Femboy Fucking Redhead Trans Woman Raw - Compilation 4
    Bailey Wilde
    19.3K views
    Sissy Fucker
    04:33
    Sissy Fucker
    FrinaXXX
    3.2K views
    Amateur Couple and Trans - Train
    22:45
    Amateur Couple and Trans - Train
    MySchoolLife
    1M views
    Sissy crossdresser swallows her own cum
    15:27
    Sissy crossdresser swallows her own cum
    S Sam_cdsissy
    1K views
    Crossdreser housekeepers have sex in their boss's room
    09:41
    Crossdreser housekeepers have sex in their boss's room
    WanidaCrossdresser
    33.9K views
    He stretched my asshole wide open!
    06:00
    He stretched my asshole wide open!
    missangell_
    208K views
    Sloppy Blowjobs Daddy and Beautiful Sissy Huge Cumload
    10:48
    Sloppy Blowjobs Daddy and Beautiful Sissy Huge Cumload
    Viper Fierce
    29K views
    Wealthy Daddy Calls Bellboy and Fucks Him in the Mouth with His Big Cock
    12:03
    Wealthy Daddy Calls Bellboy and Fucks Him in the Mouth with His Big Cock
    Mark Lugaev
    67.6K views
    Wife Videos Sissy Cuckol Being Fucked By Crossdressing stran
    02:44
    Wife Videos Sissy Cuckol Being Fucked By Crossdressing stran
    491.6K views
    Swallow My Cum
    15:15
    Swallow My Cum
    TSRyley
    240.6K views
    Short Satin Dress with Tights
    03:28
    Short Satin Dress with Tights
    Sarahsatinslut
    3.1K views
    Daddy's FIRST Blowjob from A Sissy Crossdresser on Grindr
    01:08
    Daddy's FIRST Blowjob from A Sissy Crossdresser on Grindr
    381.7K views
    Crossdresser Car Blowjob
    02:27
    Crossdresser Car Blowjob
    151.5K views
    My crossdresser friend and I had sex in the room.
    14:14
    My crossdresser friend and I had sex in the room.
    WanidaCrossdresser
    50.8K views
    Petra,s 6th training
    16:42
    Petra,s 6th training
    PetraTVsletje
    71.4K views
    Cute Virginal Clit Cumshot
    08:17
    Cute Virginal Clit Cumshot
    Cindy Belfast
    67.7K views
    Trans Girl Forced Orgasm
    08:12
    Trans Girl Forced Orgasm
    Mistress Jodie May
    105K views
    Gigi and David, recording of sex live show, integral, unedited, uncut. POV, behind the scene, webcam 11.03.2025 - part 4
    30:07
    Gigi and David, recording of sex live show, integral, unedited, uncut. POV, behind the scene, webcam 11.03.2025 - part 4
    Gigi and David
    98.4K views
    Sissy Heelya gets assfucked bareback, slurps & swallows cum
    02:44
    Sissy Heelya gets assfucked bareback, slurps & swallows cum
    240K views
    Too Feminine to Be a Man, Too Dirty to Be a Woman
    05:27
    Too Feminine to Be a Man, Too Dirty to Be a Woman
    MTFXXXVIDS
    29.2K views
    ́At night in hold-ups and orgasm
    10:15
    ́At night in hold-ups and orgasm
    sweetfeet29
    3.4K views
    Throated, Fucked and Bred
    07:33
    Throated, Fucked and Bred
    Mistress Jodie May
    258.9K views
    • Back
    • 1
    • ...
    • 5
    • 6
    • 7
    • 8
    • 9
    • ...
    • 285
    • Next

    Searches Related to Sissy Crossdresser

    • The Sissy's Future
    • Pansexual Orgy
    • Extrem Crossdressers
    • Panty Fetish
    • Boys Wearing High Heels
    • Transgender Pantyhose
    • Caught Crossdressing
    • Traps Fuck
    • Hotel Hooker
    • Bisexual Gloryhole
    • Bitch
    • Pornstar
    • Sissynikky
    • Feminization Bondage
    • Old Transvestites
    • Sissies
    • Cuckold Eunuch
    • Sissynikki
    • Crossdress
    • Permanent Sissification

    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