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
    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
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Pain Anal Dildo Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.3M views
    Ass to mouth: painful naked anal dildo masturbation
    16:11
    Ass to mouth: painful naked anal dildo masturbation
    4K views
    why do I suddenly love trannys?
    12:46
    why do I suddenly love trannys?
    1.2M views
    116 min degrading of bdsm sissy pain whore Alina
    02:20
    116 min degrading of bdsm sissy pain whore Alina
    alinanightsky
    79.4K views
    handz free shemale cumming while getting fucked
    13:40
    handz free shemale cumming while getting fucked
    2.4M views
    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    18:39
    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    Derek6699
    101.1K views
    Shemale Anatomy
    03:06
    Shemale Anatomy
    2.8M views
    Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots
    17:38
    Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots
    Derek6699
    74K views
    Veronica Leal Surprises Stacy Cruz with Her FUTA Dick and Gets Her Tight Ass Destroyed - FULL SCENE
    12:33
    Veronica Leal Surprises Stacy Cruz with Her FUTA Dick and Gets Her Tight Ass Destroyed - FULL SCENE
    Futanari XXX
    21.3M views
    The sissy pain whore Alina show her skills in self-humiliation and deep throating with dildo
    02:55
    The sissy pain whore Alina show her skills in self-humiliation and deep throating with dildo
    alinanightsky
    27.6K views
    Fisting Double Sissygasm Cumshots
    01:38
    Fisting Double Sissygasm Cumshots
    Lola Spais
    156.4K 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.
    Denise Humain
    42.4K views
    He Screams For Shemeat Compilation 2020 (TS TOPS)
    15:53
    He Screams For Shemeat Compilation 2020 (TS TOPS)
    2.9M views
    Up Close Painful Femboy Dildo Practice
    01:04
    Up Close Painful Femboy Dildo Practice
    Khatara Shikiku
    5.8K views
    Sissy cums too early and gets punished with rough fucking
    02:35
    Sissy cums too early and gets punished with rough fucking
    2.1M views
    Extreme Anal Insertion Two Foot Long XXL Anal Slink
    10:11
    Extreme Anal Insertion Two Foot Long XXL Anal Slink
    TheToxicTwins
    45.1K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    Young Goth Trans Does Painful Anal
    06:12
    Young Goth Trans Does Painful Anal
    Khatara Shikiku
    8.8K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    1.9M views
    Newest Scene Compilation (with new Stuff) incl. Anal, Gaping, Nipple Pain, Humiliation, Sissy, BDSM, Trans, Denise Humain
    13:53
    Newest Scene Compilation (with new Stuff) incl. Anal, Gaping, Nipple Pain, Humiliation, Sissy, BDSM, Trans, Denise Humain
    Denise Humain
    3K views
    Compilation: Trannies Cum While they get Fucked
    13:29
    Compilation: Trannies Cum While they get Fucked
    3.8M views
    A naughty housemaid with ripped black pantyhose tried the thickest dildo into her sissy pussy and moaned with pain and joy
    07:15
    A naughty housemaid with ripped black pantyhose tried the thickest dildo into her sissy pussy and moaned with pain and joy
    Harinni
    3.2K views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    1.8M views
    Another weekend - Same result, nipples hurt, asshole is destroyed, still i wish i dont had to do it by myself.
    14:21
    Another weekend - Same result, nipples hurt, asshole is destroyed, still i wish i dont had to do it by myself.
    Denise Humain
    13.7K views
    He Tears His Cute Trans Roommate's Pantyhose To Bang Her
    10:54
    He Tears His Cute Trans Roommate's Pantyhose To Bang Her
    Devils tgirls
    6M views
    Synnz & Mistress Cy "50 Shades of Fucked Up" Shemale Tattoo BDSM Kink Fuck Session (FULL RELEASE)
    01:29:00
    Synnz & Mistress Cy "50 Shades of Fucked Up" Shemale Tattoo BDSM Kink Fuck Session (FULL RELEASE)
    Cyanide Mistress Of Darkness
    28.5K views
    21 inches in my ass! BULGE. I'm cumming while a dildo stirs my stomach
    07:08
    21 inches in my ass! BULGE. I'm cumming while a dildo stirs my stomach
    Starlightfemboy
    482.3K views
    Rebeccas Maso Perversions
    22:12
    Rebeccas Maso Perversions
    Rebeccafuxx
    14K views
    Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie
    03:38
    Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie
    Melodyfluffington
    32.4K views
    Fifty Shades of FUCKED UP!! Advance Preview Trailer!!
    03:41
    Fifty Shades of FUCKED UP!! Advance Preview Trailer!!
    Cyanide Mistress Of Darkness
    10.3K views
    Hung Transgirl Deep Anal Prostate Orgasms 11 Inch Dildo Riding Jessica Bloom
    05:53
    Hung Transgirl Deep Anal Prostate Orgasms 11 Inch Dildo Riding Jessica Bloom
    Jessica Bloom
    125.4K views
    School Uniform Painful Dragon Dildo Fuck
    07:15
    School Uniform Painful Dragon Dildo Fuck
    PrincessKitti3
    just added
    Daddy Milks Trans Girl Prostate
    05:06
    Daddy Milks Trans Girl Prostate
    Gray Perrier
    319.7K views
    Selfuking
    04:12
    Selfuking
    Papiricoo
    38.5K views
    Hands Free Sissy Orgasms Vol 11
    18:15
    Hands Free Sissy Orgasms Vol 11
    330.2K views
    MissRose TS -Preview BBC GIANT XXXL Dildo Painal Moan Outdoors - Shemale Got Caught Anal Stretching - Big Cock Pumping M
    01:29
    MissRose TS -Preview BBC GIANT XXXL Dildo Painal Moan Outdoors - Shemale Got Caught Anal Stretching - Big Cock Pumping M
    MissRose TS
    18.8K views
    Illuxxxtrandy Hot Blonde with Big Ass Fucked Doggy Style by Huge Monster Cock in Public Bathroom - Intense, Dirty Sex with Tight
    02:15
    Illuxxxtrandy Hot Blonde with Big Ass Fucked Doggy Style by Huge Monster Cock in Public Bathroom - Intense, Dirty Sex with Tight
    sinsweethoneyasses
    2.1M views
    Rebecca's painful Orgasm
    10:49
    Rebecca's painful Orgasm
    Rebeccafuxx
    9.4K views
    Sissy Cums Too Early And Gets Punished With Rough Fucking.
    03:20
    Sissy Cums Too Early And Gets Punished With Rough Fucking.
    959.5K views
    Painful Anal Stretching With Facial
    06:53
    Painful Anal Stretching With Facial
    Chantal Fouet
    4.8K views
    Big Tits Asian Nurse Finds Out Her Disabled Patient Has A Cock
    11:07
    Big Tits Asian Nurse Finds Out Her Disabled Patient Has A Cock
    Futanari XXX
    7.5M views
    Tabasco Dildo Punishment for forgetting my butt plug today...
    02:50
    Tabasco Dildo Punishment for forgetting my butt plug today...
    Sissy-Hinata
    3.5K views
    Amateur Tgirls Destroying Their Holes with GIANT Dildos
    22:40
    Amateur Tgirls Destroying Their Holes with GIANT Dildos
    614K views
    Anal sensation, shemale fucks ass without dilating, an exciting pain, ladyboy evenya beautiful
    08:59
    Anal sensation, shemale fucks ass without dilating, an exciting pain, ladyboy evenya beautiful
    femboyass469
    4.8K views
    Shemale dildo hero - Try not to cum with pure anal pleasure
    54:39
    Shemale dildo hero - Try not to cum with pure anal pleasure
    1.1M views
    got a new toy with electro shock and vibrating function
    08:24
    got a new toy with electro shock and vibrating function
    8.7K views
    shemale dildo hero - inflatable training
    37:16
    shemale dildo hero - inflatable training
    163.8K 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