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
    • Sissy
    • Shemale Fucks Girl
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Cum In Mouth
    • Big Black Cock
    • Big Ass
    • Bareback
    • Creampie
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Crossdressing Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Crossdressing Husband
    Sissy POV
    Chastity Sissy
    Sissy Public
    Cute Sissy
    French Sissy
    Sissy Orgasm
    Sissy Spanking
    Sissy Moaning
    Sissy Orgy
    Sissy School
    Sissy Mistress
    Sissy Swallow
    Little Sissy
    Sissy Bnwo
    Sissy Story
    Sissy Fisting
    Japanese Sissy
    Sissy Trap
    Sissy Punishment
    Best Videos
    By clicking the content you will also see an ad. AD
    Secret crossdresser rendezvous
    08:12
    Secret crossdresser rendezvous
    Pure Ts
    64.7K views
    Big daddy fuck 19 years old sissy
    06:34
    Big daddy fuck 19 years old sissy
    Crystal Phoenix
    125.3K views
    Black Sissy Cuck fucked by the Wife's White BWC Bull Lover
    10:42
    Black Sissy Cuck fucked by the Wife's White BWC Bull Lover
    Fiona Fortune
    113.4K 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
    573.2K views
    Precum Explosion Inside the Pantyhose
    05:11
    Precum Explosion Inside the Pantyhose
    MTFXXXVIDS
    19.8K 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
    233.3K views
    Would you like to feel my bulge in my dress
    05:15
    Would you like to feel my bulge in my dress
    Hollycd1
    16.1K views
    Shemale fucked on the couch
    14:44
    Shemale fucked on the couch
    Elwadeoh
    729.8K views
    Big load from femcock Monstercock from a cute girl
    00:58
    Big load from femcock Monstercock from a cute girl
    Samantha Sissy World
    647.4K views
    Cindy Sissygasms Her Pretty Clit in Pink Panties
    05:10
    Cindy Sissygasms Her Pretty Clit in Pink Panties
    Cindy Belfast
    244.9K views
    Shemale gets shared with massive dick from BBC compilation
    18:46
    Shemale gets shared with massive dick from BBC compilation
    DaddyandLexa
    225.4K views
    Kitty tranny maid Victoria Grant bareback deep fucking
    06:41
    Kitty tranny maid Victoria Grant bareback deep fucking
    TS Playground
    223.8K views
    Asian Femboy goes black..
    05:25
    Asian Femboy goes black..
    Lola Femme
    1.2M views
    shemale cum sissy slut cums Trans cumming
    16:14
    shemale cum sissy slut cums Trans cumming
    SissyGirlTs
    36.8K views
    Big Dick Femboy Cumshot Compilation 4 - alizevert
    07:25
    Big Dick Femboy Cumshot Compilation 4 - alizevert
    alizevert
    898K views
    Much Sexier Than Most Women
    08:12
    Much Sexier Than Most Women
    Pure Ts
    224K 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
    Veronica Sanders
    184.1K views
    Stepdaddy fuck trans 20yo stepdaughter
    08:53
    Stepdaddy fuck trans 20yo stepdaughter
    Crystal Phoenix
    370.6K views
    Wife Videos Sissy Cuckol Being Fucked By Crossdressing stran
    02:44
    Wife Videos Sissy Cuckol Being Fucked By Crossdressing stran
    495.8K 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
    261.8K views

    Relevant Short videos

    Sissy crossdressing Madison CD rides a BBC dildo as she Crossdresser in lingerie  and stockings | Clip 1
    Sissy crossdressing Madison CD rides a BBC dildo as she Crossdresser in lingerie and stockings | Clip 1
    MadisonCD2025
    just added
    Cumming hard with butthole twitching
    Cumming hard with butthole twitching
    Zoeqt
    189K views
    cumming like crazy
    cumming like crazy
    boobyb0y
    252.6K views
    Surprise Cumshot
    Surprise Cumshot
    Zoeqt
    284.6K views
    Hardcore negative chastity
    Hardcore negative chastity
    boobyb0y
    266.1K views
    Gerudo Link cumming like a bitch
    Gerudo Link cumming like a bitch
    Zoeqt
    79.1K 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
    218.3K views
    Fucking my trans stepdaughter bareback like the bitch she is
    15:00
    Fucking my trans stepdaughter bareback like the bitch she is
    Smoker Master
    92.3K 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
    308.2K views
    My stepbrother fucks my ass in the kitchen. Part 1
    10:06
    My stepbrother fucks my ass in the kitchen. Part 1
    PalmasRecordsMen
    436.6K views
    Sex before breakfast
    10:32
    Sex before breakfast
    Elwadeoh
    907.9K views
    Thick Cock with New Morning Coat
    06:40
    Thick Cock with New Morning Coat
    Sonitchka
    35.9K views
    extreme masturbation
    11:11
    extreme masturbation
    TSquennAna
    149.9K 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)
    Veronica Sanders
    618.7K views
    Super Sexy Goth Femboy Jade Madison Sucking and Fucking - Compilation 2
    08:12
    Super Sexy Goth Femboy Jade Madison Sucking and Fucking - Compilation 2
    Bailey Wilde
    97.6K 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
    178.7K views
    Threesome of young trans with a hung BBC cock
    07:31
    Threesome of young trans with a hung BBC cock
    Crystal Phoenix
    212.1K views
    Sweet 18yo Trans Girl Anal Mastrubation
    06:34
    Sweet 18yo Trans Girl Anal Mastrubation
    Fembaby
    44.7K views
    Cumshots 2024 Part II
    05:19
    Cumshots 2024 Part II
    Strapsex
    347.6K 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
    234.8K views
    Sissy crossdress anal slut gets thick uncut dick bare in her little ass
    53:14
    Sissy crossdress anal slut gets thick uncut dick bare in her little ass
    Tgirl Riley
    152.9K views
    BF demolishes my young femboy bussy (2025 Remaster)
    12:36
    BF demolishes my young femboy bussy (2025 Remaster)
    Prettyboi2000x
    69.9K views
    Stroking my throbbing dick for you
    01:27
    Stroking my throbbing dick for you
    barbiebelladollz
    67.6K views
    Chubby crossdresser getting fucked by BBC bareback
    01:30
    Chubby crossdresser getting fucked by BBC bareback
    472K views
    Total Sissy Amnesia
    13:20
    Total Sissy Amnesia
    Natalie Napoli
    28.1K 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_
    235.8K views
    Extreme Anal Gape Xxxl Dildo & Fuck Machine
    05:56
    Extreme Anal Gape Xxxl Dildo & Fuck Machine
    Elvi Lynx
    64.6K views
    Tranny dominates you at work
    07:05
    Tranny dominates you at work
    Kymmy Harper
    706.3K views
    Petite bitch begs for this huge cock deep inside her dirty asshole
    05:12
    Petite bitch begs for this huge cock deep inside her dirty asshole
    MrNastyXavier
    246K views
    Mature Trans Gets Fucked by a Black Guy
    36:38
    Mature Trans Gets Fucked by a Black Guy
    Trans and Co
    360.7K views
    Trans Girl Masturbating and Cums All Over Her Self
    03:44
    Trans Girl Masturbating and Cums All Over Her Self
    Bellaroar
    154.3K views
    Sucking My Own Cock Til I Cum
    05:50
    Sucking My Own Cock Til I Cum
    Emily Meadows
    142.7K views
    Petite bitch loves to fuck in pantyhose with her roommate
    06:23
    Petite bitch loves to fuck in pantyhose with her roommate
    MrNastyXavier
    198.3K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Crossdressing

    • 2 Sissies Playing
    • Femme Girls
    • Tgirltrainernl
    • Sissycdmish
    • Sissie
    • Emo Goth TS
    • See Through Lingerie
    • Cross Dressers
    • Shemales in Skirts
    • Successful Transition Mtf
    • Transvestite Party UK
    • Nude Belly Dance
    • Fem Boys
    • Bare Bottom Spanking
    • Teen Femboys
    • Feminize
    • Tranny Gangbanged
    • Pantys
    • Black Tgirls
    • Chastity Maid

    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