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
    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

    Painful Anal Insertion Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3.1M views
    FtM stuffed and whipped painfully
    07:06
    FtM stuffed and whipped painfully
    1.1K views
    Teen Gets Her 1st Painful Screaming Anal But Let Her Finish
    10:28
    Teen Gets Her 1st Painful Screaming Anal But Let Her Finish
    101.7K views
    fucking my femboy slave sissy slut painful anal
    01:33
    fucking my femboy slave sissy slut painful anal
    132.1K views
    Totally destroyed ass
    11:01
    Totally destroyed ass
    761.1K views
    HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-
    31:02
    HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-
    108.9K views
    Blond angel tranny can't take this painal anymore
    07:11
    Blond angel tranny can't take this painal anymore
    93.7K views
    Young Goth Trans Does Painful Anal
    06:12
    Young Goth Trans Does Painful Anal
    Khatara Shikiku
    9.2K views
    Tranny Barbie can't take the BBC and tries to get away but he keeps fucking my ass hard - amateur shemale - Candy Ass Sissy
    06:08
    Tranny Barbie can't take the BBC and tries to get away but he keeps fucking my ass hard - amateur shemale - Candy Ass Sissy
    Candy Ass Sissy
    66.4K views
    Painful Anal Stretching With Facial
    06:53
    Painful Anal Stretching With Facial
    Chantal Fouet
    5K views
    Sissy's asshole is filled up to a meter deep
    17:25
    Sissy's asshole is filled up to a meter deep
    Drift3-4
    726.2K views
    Desi painful anal sex poojakichut
    05:55
    Desi painful anal sex poojakichut
    RoZestyBypass99
    14.9K views
    Extreme Painanal large dildo with chilli sauce pushes Denise to her limits and makes her cry.
    14:26
    Extreme Painanal large dildo with chilli sauce pushes Denise to her limits and makes her cry.
    FapHouse
    43.9K views
    Painful Anal Training On My Sissy Bitch Outdoors with 8inch Dildo
    09:57
    Painful Anal Training On My Sissy Bitch Outdoors with 8inch Dildo
    32.1K views
    Prolapse Fucking with Fingers, Double Ender and Cock
    08:30
    Prolapse Fucking with Fingers, Double Ender and Cock
    FapHouse
    165.8K views
    CdTina painful anal
    01:37
    CdTina painful anal
    3.3K views
    How to stay clean during anal (Toy Review)
    01:29
    How to stay clean during anal (Toy Review)
    FapHouse
    72.4K views
    Painful Anal with a huge vegetable
    01:01
    Painful Anal with a huge vegetable
    12.2K views
    Strong in her ass without condom
    08:12
    Strong in her ass without condom
    She-Male X
    2.6M views
    Morning Procedures - bathing in sheer lingerie and painful anal stretching
    06:36
    Morning Procedures - bathing in sheer lingerie and painful anal stretching
    Chantal Fouet
    5.9K views

    Relevant Short videos

    Memorable moment from "Painful Anal Stretching With Facial"
    Memorable moment from "Painful Anal Stretching With Facial"
    Chantal Fouet
    544 views
    Must-share moment from "Painful Anal Stretching With Facial"
    Must-share moment from "Painful Anal Stretching With Facial"
    Chantal Fouet
    426 views
    Stunning moment from "Painful Anal Stretching With Facial"
    Stunning moment from "Painful Anal Stretching With Facial"
    Chantal Fouet
    375 views
    Easter Chocolate Egg Anal Insertion Sploshing
    Easter Chocolate Egg Anal Insertion Sploshing
    FapHouse
    1.8K views
    Anal insertion, anal gape, buttplug, dildo
    Anal insertion, anal gape, buttplug, dildo
    AssissySarah
    326 views
    Futuretist Immoralless Anal Insertion Hot Big Ass Slut Doggy Style Fucked by Two Huge Black Cocks
    Futuretist Immoralless Anal Insertion Hot Big Ass Slut Doggy Style Fucked by Two Huge Black Cocks
    FapHouse
    615 views
    Cute Tranny Gets Her Ass Rammed by a MILF with a Big Strapon After Licking Her Pierced Pussy
    08:12
    Cute Tranny Gets Her Ass Rammed by a MILF with a Big Strapon After Licking Her Pierced Pussy
    FapHouse
    123K views
    Xxxl Anal Dildo Slaming A Sexy Sissy Ass Extrem Anal Insertion
    10:42
    Xxxl Anal Dildo Slaming A Sexy Sissy Ass Extrem Anal Insertion
    Tiffany Ciskiss
    1M views
    When you Don't Want Anymore But Master Still Gives You
    02:20
    When you Don't Want Anymore But Master Still Gives You
    987.4K views
    Futuretist Immoralless Anal Insertion Hot Big Ass Slut Doggy Style Fucked by Two Huge Black Cocks
    02:09
    Futuretist Immoralless Anal Insertion Hot Big Ass Slut Doggy Style Fucked by Two Huge Black Cocks
    Hatanoxxxmiwa
    58.5K views
    BRUTAL Tgirl TOP Gives Guy Extreme Painal
    02:24
    BRUTAL Tgirl TOP Gives Guy Extreme Painal
    1M views
    FEMOUT - Butt Plug Anal Insertion With Lovely Lea Vibing
    03:12
    FEMOUT - Butt Plug Anal Insertion With Lovely Lea Vibing
    Femout
    4.8K views
    She fucks him so hard he can't take it, very dominant shemal
    04:08
    She fucks him so hard he can't take it, very dominant shemal
    315.9K views
    anal insertion gearstick
    00:51
    anal insertion gearstick
    32K views
    Black blow up spiked butt plug for my S&M Daddies!
    08:37
    Black blow up spiked butt plug for my S&M Daddies!
    Victoria Lecherri
    44.1K views
    Shemale Elizabeth breaks her ass with 1.5 liter bottle extreme anal insertion
    11:13
    Shemale Elizabeth breaks her ass with 1.5 liter bottle extreme anal insertion
    FapHouse
    57.9K views
    Thick Anal Viring Gets Her 1st Time Very PAinful & Begging
    17:02
    Thick Anal Viring Gets Her 1st Time Very PAinful & Begging
    59.2K views
    Anal insertion big bottle
    01:44
    Anal insertion big bottle
    Amanda lovetoys
    12.5K views
    Bitch boy can't take her monster cock but she doesn't stop
    01:51
    Bitch boy can't take her monster cock but she doesn't stop
    956.7K views
    Mini Basketball Anal Insertion Compilation Ft Sissy Kenzie Star
    06:57
    Mini Basketball Anal Insertion Compilation Ft Sissy Kenzie Star
    SissyKenzieStar
    1.3K views
    73 Straight boy curious fucked and fucking trans latina big cock trans
    43:43
    73 Straight boy curious fucked and fucking trans latina big cock trans
    Onlyfans
    2.3M views
    Nympho Trans Girl Rides Her Huge 8 Inch Cock and Multiple Creampies Her Ass - Extreme Anal Insertion
    13:28
    Nympho Trans Girl Rides Her Huge 8 Inch Cock and Multiple Creampies Her Ass - Extreme Anal Insertion
    KinkySky
    11.4K views
    He Couldn't Handle Her
    01:57
    He Couldn't Handle Her
    395.6K views
    Fucking Sissy Ass On Xxl Ribbed Dildo Extrem Anal Insertion
    14:20
    Fucking Sissy Ass On Xxl Ribbed Dildo Extrem Anal Insertion
    Tiffany Ciskiss
    19.2K views
    your first time: she will slowly stretch you and then fuck u
    02:20
    your first time: she will slowly stretch you and then fuck u
    725.5K views
    Huge anal insertion compilation
    11:18
    Huge anal insertion compilation
    FapHouse
    1.5K views
    Krystallcox with Sounding Rods Urethral Play
    24:15
    Krystallcox with Sounding Rods Urethral Play
    FapHouse
    59.3K views
    50cm Dildo Anal Insertion
    01:52
    50cm Dildo Anal Insertion
    SissyKenzieStar
    1.6K views
    Big Ass Blond TS Screams as Monster Cock BBC Daddy Destroys
    09:51
    Big Ass Blond TS Screams as Monster Cock BBC Daddy Destroys
    Candy Ass Sissy
    188.5K views
    Goth Trans Girl Self Fucking Leads To HUGE CREAMPIE - Extreme Anal Insertion
    10:29
    Goth Trans Girl Self Fucking Leads To HUGE CREAMPIE - Extreme Anal Insertion
    KinkySky
    30K views
    TRANSEROTICA Naughty TS Lianna Lawson Uses Metal Rod On Cock
    12:00
    TRANSEROTICA Naughty TS Lianna Lawson Uses Metal Rod On Cock
    Trans Erotica
    200.5K views
    transvestite elizabeth breaking her anus with extreme mega anal insertion with rare objects
    10:54
    transvestite elizabeth breaking her anus with extreme mega anal insertion with rare objects
    Elizabeth BDSM
    19.1K views
    DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
    02:37
    DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
    233.4K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next
    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