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
    • Shemale Fucks Girl
    • Sissy
    • 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

    Crossdresser Pain Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Crossdresser
    Pain
    Sissy Crossdresser
    Amateur Crossdresser
    Mature Crossdresser
    Crossdresser Fucked
    Crossdresser Blowjob
    Japanese Crossdresser
    Crossdresser Gangbang
    Crossdresser Sex
    Old Crossdresser
    Crossdresser Lingerie
    Crossdresser BBC
    Crossdresser Anal
    Beautiful Crossdresser
    French Crossdresser
    Crossdresser Creampie
    Crossdresser Orgy
    Vintage Crossdresser
    Russian Crossdresser
    Best Videos
    By clicking the content you will also see an ad. AD
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    2M 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
    221.7K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M 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
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.7M views
    Compilation with Weekly Episodes from the pain whore Alina
    02:05
    Compilation with Weekly Episodes from the pain whore Alina
    alinanightsky
    65.7K 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
    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    18:39
    Spiked Chastity Cage Torment - Sissy Maids Self Bondage
    Derek6699
    102.2K views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    2M 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
    74.9K views
    Long Anal Session for Hurting Emma Tied to the Bench
    01:05:06
    Long Anal Session for Hurting Emma Tied to the Bench
    FapHouse
    278.1K views
    116 min degrading of bdsm sissy pain whore Alina
    02:20
    116 min degrading of bdsm sissy pain whore Alina
    alinanightsky
    80.1K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    840.1K views
    More maintenance spanking for Kitsy. OTK punishment.
    06:53
    More maintenance spanking for Kitsy. OTK punishment.
    Kitsy Meow
    24.4K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3.1M views
    Pathetic Maid Apology Riding Crop Self Punishment
    13:17
    Pathetic Maid Apology Riding Crop Self Punishment
    JessicaLynn15
    2.8K views
    Daddy Milks Trans Girl Prostate
    05:06
    Daddy Milks Trans Girl Prostate
    Gray Perrier
    348.8K views
    Slapping My Tits and Ass Like a Good Pain Slut
    08:55
    Slapping My Tits and Ass Like a Good Pain Slut
    FapHouse
    6.6K views
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    29:33
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    FapHouse
    2.6M 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
    28.9K views

    Relevant Short videos

    Thrilling moment from "A sissy tortures her buttocks severely with nettles, ties up her balls, dildoes herself and makes herself cum with the vibrator"
    Thrilling moment from "A sissy tortures her buttocks severely with nettles, ties up her balls, dildoes herself and makes herself cum with the vibrator"
    MyLolaTrav
    443 views
    Sissy Whores Anal Seduction Comeback: Denise Humain as Pink Lingerie Cumslut – Begging for extreme gangbangs, deepthroat & gaping holes! | Clip 1
    Sissy Whores Anal Seduction Comeback: Denise Humain as Pink Lingerie Cumslut – Begging for extreme gangbangs, deepthroat & gaping holes! | Clip 1
    Denise Humain
    690 views
    Sissy Denise: Nipple torture with combination pliers – Live until the end | Clip 1
    Sissy Denise: Nipple torture with combination pliers – Live until the end | Clip 1
    Denise Humain
    263 views
    Epic moment from "Working on Sissy Slave Denise Humain Nipples for hours Part 1"
    Epic moment from "Working on Sissy Slave Denise Humain Nipples for hours Part 1"
    Denise Humain
    696 views
    Must-share moment from "Painful Anal Stretching With Facial"
    Must-share moment from "Painful Anal Stretching With Facial"
    Chantal Fouet
    409 views
    Memorable moment from "Painful Anal Stretching With Facial"
    Memorable moment from "Painful Anal Stretching With Facial"
    Chantal Fouet
    544 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
    241.9K views
    Crossdresser enjoys a very painful flogging session in the d
    21:10
    Crossdresser enjoys a very painful flogging session in the d
    eroticfemaledominati
    178.7K views
    Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
    08:09
    Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
    Kitsy Meow
    173.7K views
    Sissy Maid Icy Hot Wooden Pony Punishment 2
    23:29
    Sissy Maid Icy Hot Wooden Pony Punishment 2
    Derek6699
    39.8K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.2M views
    A desperate trap sissy pain whore asks a top man to take her as a sex slave and let him fuck her throat and ass
    01:34
    A desperate trap sissy pain whore asks a top man to take her as a sex slave and let him fuck her throat and ass
    alinanightsky
    41.7K views
    This is how you treat a sissy slut! Guy uses tranny brutally in public and cums on her face!
    01:16
    This is how you treat a sissy slut! Guy uses tranny brutally in public and cums on her face!
    TV_Helena
    555.2K 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
    Extreme Hard Spaking for the Maso Cunt
    08:02
    Extreme Hard Spaking for the Maso Cunt
    FapHouse
    203.5K views
    Sissy Nipple Cow Chastity Nipple Pump Electro Pain
    02:06
    Sissy Nipple Cow Chastity Nipple Pump Electro Pain
    Titten-Sau
    26.3K views
    Shemale Anatomy
    03:06
    Shemale Anatomy
    2.8M views
    Sissy Maids Punishment
    07:53
    Sissy Maids Punishment
    Derek6699
    28.1K views
    Mamou with Rachelle Karol I Dominate a Pretty Submissive Before Taking Her Part 2
    12:58
    Mamou with Rachelle Karol I Dominate a Pretty Submissive Before Taking Her Part 2
    Mamou5891
    77.6K views
    Icy Hot Wooden Pony Self Bondage Torture
    17:40
    Icy Hot Wooden Pony Self Bondage Torture
    Derek6699
    26.7K views
    Many crossdressers fucked scrnrs
    01:09:02
    Many crossdressers fucked scrnrs
    1.4M 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
    3.4K views
    anal destruction and face slapping for maso whore
    10:41
    anal destruction and face slapping for maso whore
    ActorFab
    116.2K views
    Working on Sissy Slave Denise Humain Nipples for hours Part 1
    10:01
    Working on Sissy Slave Denise Humain Nipples for hours Part 1
    Denise Humain
    70.9K views
    Lena Vesper Gets Fisted & Milked by MILF Bane Jane
    01:11
    Lena Vesper Gets Fisted & Milked by MILF Bane Jane
    FapHouse
    159.2K views
    Let her feel what Nipple Pain means. Let her suffer to her limit while we smile at her.
    13:59
    Let her feel what Nipple Pain means. Let her suffer to her limit while we smile at her.
    Denise Humain
    20.5K views
    You Are Just a Hole - Variety Itsol
    10:46
    You Are Just a Hole - Variety Itsol
    Rodrigo Amor
    1.9M views
    Sissy Whores Anal Seduction Comeback: Denise Humain as Pink Lingerie Cumslut – Begging for extreme gangbangs, deepthroat & gaping holes!
    05:13
    Sissy Whores Anal Seduction Comeback: Denise Humain as Pink Lingerie Cumslut – Begging for extreme gangbangs, deepthroat & gaping holes!
    Denise Humain
    3.2K 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
    43.1K 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
    3.5K views
    Hard Belting my sissy slave two
    01:36
    Hard Belting my sissy slave two
    116.9K views
    Sadistic vampire Mistress
    05:41
    Sadistic vampire Mistress
    Jazebel
    7.6K views
    Sauna sissy slut got deepthroated and anal fucking like a good sex slave for BDSM
    39:24
    Sauna sissy slut got deepthroated and anal fucking like a good sex slave for BDSM
    alinanightsky
    166.5K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Crossdresser Pain

    • Crossdresser Painful Anal
    • Fucking a Sissy Femboy
    • Extreme Pain
    • Brutal BBC Fucks CD
    • Shemale Crying
    • Beautiful Agony
    • No Mercy Fuck
    • Rough Hardcore Punishment
    • Body Swap Gender Transformation
    • Femdom Humiliation
    • Please Stop
    • Too Deep
    • Crossdressers Getting Fucked
    • Secret Sissyboy
    • Sisy Boy
    • Degraded Sissies
    • Ruined Ass
    • Traps Femboys and Sissys
    • Amateur Painal Compilation
    • Wife Humiliated
    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