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

    Pegging Crossdresser Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Extreme Cock for Sissy Hole!!
    05:24
    Extreme Cock for Sissy Hole!!
    Lola Spais
    266.9K views
    Sissy Doll Fucking in a Pegging Date
    07:00
    Sissy Doll Fucking in a Pegging Date
    Brat Perversions
    13.8K views
    Sissy Maid Pegged for Job
    05:22
    Sissy Maid Pegged for Job
    Bailey Wilde
    79.9K views
    Sissy Training - Dominatrix Pegs Goth Sissy and Makes Her Swallow Cum
    10:08
    Sissy Training - Dominatrix Pegs Goth Sissy and Makes Her Swallow Cum
    Bailey Wilde
    46.2K views
    Sissification and Fucked for Job
    03:04
    Sissification and Fucked for Job
    Bailey Wilde
    88.2K views
    Double Fuck for Sissy Hole
    08:58
    Double Fuck for Sissy Hole
    FrinaXXX
    4.4K views
    Transgirl Transformed as a Human Sexdoll
    02:20
    Transgirl Transformed as a Human Sexdoll
    Emmy Angeles
    6.7K views
    Feminization and Pegged to Get Maid Job
    03:04
    Feminization and Pegged to Get Maid Job
    Bailey Wilde
    76.8K views
    Lesbian Shemale Making Love in Japanese School Uniform
    04:58
    Lesbian Shemale Making Love in Japanese School Uniform
    SissyKanisa
    54.5K views
    Sissy Maid Worships Boss Feet and Pegged
    06:08
    Sissy Maid Worships Boss Feet and Pegged
    Bailey Wilde
    24.2K views
    Man Feminized by Roommate as Discipline
    10:41
    Man Feminized by Roommate as Discipline
    Bailey Wilde
    36.4K views
    Sissygasm From Pegging
    01:53
    Sissygasm From Pegging
    FrinaXXX
    8.1K views
    My Pussy Will Fuck You with a Huge Dildo
    02:52
    My Pussy Will Fuck You with a Huge Dildo
    FrinaXXX
    4.5K views
    Dominatrix Feminizes Sissy into Maid
    05:01
    Dominatrix Feminizes Sissy into Maid
    Bailey Wilde
    56.5K views
    Homemade Pegging Sissy
    02:29
    Homemade Pegging Sissy
    FrinaXXX
    6.5K views
    Guy Feminized into Goth Girl Gets Fucked by Dominatrix
    04:22
    Guy Feminized into Goth Girl Gets Fucked by Dominatrix
    Bailey Wilde
    26.9K views
    POV BBC Pegging
    01:28
    POV BBC Pegging
    Lola Spais
    5.1K views
    A Trans Fucked on the Couch
    01:58
    A Trans Fucked on the Couch
    Emmy Angeles
    5.6K views
    Pegging Strapon Fuck
    03:11
    Pegging Strapon Fuck
    FrinaXXX
    5.4K views
    Woman Puts Nails on Crossdresser
    05:02
    Woman Puts Nails on Crossdresser
    Bailey Wilde
    2.6K views
    TS SexyBrody in Fist Fuck SexyBrodys Hungry Hole
    01:22
    TS SexyBrody in Fist Fuck SexyBrodys Hungry Hole
    SexyFunCoupleNearU
    14.8K views
    Belyla Bradley Puts Nails on Sissy Bailey Wilde
    05:06
    Belyla Bradley Puts Nails on Sissy Bailey Wilde
    Bailey Wilde
    2.3K views
    Lola Cumming Cunt
    02:14
    Lola Cumming Cunt
    FrinaXXX
    4.1K views
    Lesbo Nun Get Fucktd
    02:02
    Lesbo Nun Get Fucktd
    FrinaXXX
    3K views
    Sissy Training - Dominatrix Pegs Sissy
    05:16
    Sissy Training - Dominatrix Pegs Sissy
    Bailey Wilde
    8.7K views
    Sissification and Pegged to Get Maid Job
    04:28
    Sissification and Pegged to Get Maid Job
    Bailey Wilde
    7.6K views
    Hot Crossdressing Babe Reverse Cowgirl Pegged
    03:55
    Hot Crossdressing Babe Reverse Cowgirl Pegged
    Bailey Wilde
    2.6K views
    Sissy Training - Dominatrix Pegs Sissy Cheerleader
    03:43
    Sissy Training - Dominatrix Pegs Sissy Cheerleader
    Bailey Wilde
    10K views
    Valentine’s Day sluts
    21:45
    Valentine’s Day sluts
    Shelly Robertss
    8.6K views
    Gorgeous Nuns Cum Pegging
    05:39
    Gorgeous Nuns Cum Pegging
    FrinaXXX
    5.9K views
    Prisoner Kanisa Get Punishment From Officer Wei and Officer Reina
    00:50
    Prisoner Kanisa Get Punishment From Officer Wei and Officer Reina
    SissyKanisa
    3.5K views
    Lady Alice (mobile View 9:16) 10 Part 07 Original Version
    06:35
    Lady Alice (mobile View 9:16) 10 Part 07 Original Version
    Mesmeriza
    9.1K views
    Hot Crossdresser Pegged with HUGE Strapon
    02:03
    Hot Crossdresser Pegged with HUGE Strapon
    Bailey Wilde
    2.3K views
    Hot Crossdressing Babe Pegged with HUGE Strapon
    05:59
    Hot Crossdressing Babe Pegged with HUGE Strapon
    Bailey Wilde
    2.2K views
    Hot Sissy Babe Pegged
    03:33
    Hot Sissy Babe Pegged
    Bailey Wilde
    1.8K views
    Pegged and Sissy Training
    03:02
    Pegged and Sissy Training
    Bailey Wilde
    3.9K views
    Sissy Pegged by Mistress Pixie
    02:23
    Sissy Pegged by Mistress Pixie
    Bailey Wilde
    2.3K views
    Hot Crossdressing Babe Pegged
    07:50
    Hot Crossdressing Babe Pegged
    Bailey Wilde
    1.9K views
    Crossdressing Blonde Babe Pegged
    06:50
    Crossdressing Blonde Babe Pegged
    Bailey Wilde
    2.2K views
    Lady Alice (mobile View 9:16) 10 Part 03
    08:12
    Lady Alice (mobile View 9:16) 10 Part 03
    Mesmeriza
    5.3K views
    Lady Alice (mobile View 9:16) 10 Part 01
    08:12
    Lady Alice (mobile View 9:16) 10 Part 01
    Mesmeriza
    4.4K views
    Hot Crossdressing Babe Cowgirl Pegged
    03:14
    Hot Crossdressing Babe Cowgirl Pegged
    Bailey Wilde
    1.5K views
    Hot Trans Babe Pegged
    04:55
    Hot Trans Babe Pegged
    Bailey Wilde
    3.5K views
    Lady Alice (mobile View 9:16) 10 Part 06
    08:12
    Lady Alice (mobile View 9:16) 10 Part 06
    Mesmeriza
    3.1K views
    SEXY TRANS VARIETYITSOL RECEIVES PUNISHMENT AND PEGGING FROM LIVIE BLAINN
    36:06
    SEXY TRANS VARIETYITSOL RECEIVES PUNISHMENT AND PEGGING FROM LIVIE BLAINN
    Livie Blainn
    49.4K views
    Divine Fucking Slutty Shakki
    15:06
    Divine Fucking Slutty Shakki
    Dark Films Trans
    14.9K views
    Pegged and Fisted by Ellie Shou(le)
    14:05
    Pegged and Fisted by Ellie Shou(le)
    Alyson Eclair
    49.4K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Pegging Crossdresser

    • Crossdresser Strapon
    • Crossdressing Husband Caught by Wife
    • British Mature Crossdressers
    • Femdom Pegging Sissy
    • Men Dressed as Woman
    • Crossdress Gangbang
    • Homemade Crossdresser
    • Secret Sissyboy
    • Feminized and Fucked
    • Crossdressing Husband
    • Russian Pegging
    • Crossdresserlover Ladyboys
    • Crossdresser First Time
    • Shemale Pegged
    • The Sissy's Future
    • Sissys Get Blacked
    • What Is a Sissygasm
    • Femboys in Lingerie
    • Mini Skirt Stockings Shemales
    • Femboy 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