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 Compilation Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Doggystyle Compilation
    Bbw Compilation
    3D Compilation
    Pantyhose Compilation
    Gloryhole Compilation
    Flopping Compilation
    Bottom Compilation
    Shemaletube Compilation
    Rimming Compilation
    Interracial Compilation
    Bareback Compilation
    Rough Compilation
    Natalie Mars Compilation
    Ride Compilation
    Mixed Compilation
    Hardcore Compilation
    Edging Compilation
    Aubrey Kate Compilation
    Painful BBC
    Yasmin Lee Compilation
    Best Videos
    By clicking the content you will also see an ad. AD
    Playing in public woods pain and cum
    05:23
    Playing in public woods pain and cum
    63.3K views
    A sissy tortures her buttocks severely with nettles, ties up her balls, dildoes herself and makes herself cum with the vibrator
    18:03
    A sissy tortures her buttocks severely with nettles, ties up her balls, dildoes herself and makes herself cum with the vibrator
    MyLolaTrav
    8.5K views
    EXTREME NIPPLE IN PAIN PIERCING SISSY CAROLA SMIT DGB BIZAR
    05:41
    EXTREME NIPPLE IN PAIN PIERCING SISSY CAROLA SMIT DGB BIZAR
    9.1K views
    Hot Wax On Sissy Cock
    04:15
    Hot Wax On Sissy Cock
    SubmissiveFetish
    4.8K views
    sissy slut punishing herself with a paddle
    02:49
    sissy slut punishing herself with a paddle
    Emma Huntcock
    3.7K views
    FTM fucking a huge dildo and pin orgasm
    02:34
    FTM fucking a huge dildo and pin orgasm
    Ares FTM
    2.7K views
    Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 2 - 4
    02:02
    Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 2 - 4
    Denise Humain
    4.5K views
    Shemale cock and nipples pain...
    06:02
    Shemale cock and nipples pain...
    MyLolaTrav
    5.1K views
    Tight Ass Shemale Reign Swallow 12 Inch BBC Deep Up Her Ass
    00:40
    Tight Ass Shemale Reign Swallow 12 Inch BBC Deep Up Her Ass
    FapHouse
    3.7K views
    Carlee Impaled on HUGE BBC Dildo
    01:38
    Carlee Impaled on HUGE BBC Dildo
    Carlee Kummings
    2.6K views
    how to ride a dildo
    02:36
    how to ride a dildo
    Papiricoo
    3K views
    Sissy training Extreme CBT electric shock cock pain bdsm
    00:20
    Sissy training Extreme CBT electric shock cock pain bdsm
    iFetFuc
    84.6K views
    Spanking myself a bit!
    02:33
    Spanking myself a bit!
    Bambi Christa
    3.9K views
    A sexy Sissy ties her big cock with a rope and gives her pain with nettles before cuming
    08:15
    A sexy Sissy ties her big cock with a rope and gives her pain with nettles before cuming
    MyLolaTrav
    5.1K views
    Femmby painslut plays with spiked bracelet and ruins orgasm
    05:31
    Femmby painslut plays with spiked bracelet and ruins orgasm
    Onlyfans
    3.3K views
    Preview Video for Maledoms wanna see my Sissy Skills. Sexy Deepthroat Blowjob and extreme Ass gaping pussy.
    02:47
    Preview Video for Maledoms wanna see my Sissy Skills. Sexy Deepthroat Blowjob and extreme Ass gaping pussy.
    Denise Humain
    5.3K views
    Artist. Nithes (hard and Painful Sex, Big Thick and Milky Cock with Rich Testicles)
    00:46
    Artist. Nithes (hard and Painful Sex, Big Thick and Milky Cock with Rich Testicles)
    StrightAss
    3.1K views
    Hot CD loves the anal pain she's giving herself by destroying her ass with large dildo(WARNING HOT VIDEO!!)
    06:57
    Hot CD loves the anal pain she's giving herself by destroying her ass with large dildo(WARNING HOT VIDEO!!)
    Dope Slut
    3.2K views
    Lizzy Yum august 2024 dilate and masturbate #5 nipple pain fantasy bathing pussy clit boobs
    10:34
    Lizzy Yum august 2024 dilate and masturbate #5 nipple pain fantasy bathing pussy clit boobs
    FapHouse
    1.2K views
    Girl loves pain and cum
    10:00
    Girl loves pain and cum
    13.5K views
    Sister of Pain
    04:35
    Sister of Pain
    26.8K views
    Horny tranny threesome of fun and pain
    06:42
    Horny tranny threesome of fun and pain
    48.6K views
    Ladyboy Lisa 3 Pain And Pleasure
    06:12
    Ladyboy Lisa 3 Pain And Pleasure
    Ladyboy Gold
    24.3K views
    slave for pain 2
    00:10
    slave for pain 2
    9.4K views
    Goddess AllyCDTV Got Pain on Tap
    06:56
    Goddess AllyCDTV Got Pain on Tap
    20K views
    Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 1 - 4
    02:16
    Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 1 - 4
    Denise Humain
    2.9K views
    BDSM chopsticks's play
    03:16
    BDSM chopsticks's play
    MyLolaTrav
    2.1K views
    Slut taking pain
    00:29
    Slut taking pain
    2K views
    CD in pain...
    00:20
    CD in pain...
    3.3K views
    Painful nipple torture chains
    09:19
    Painful nipple torture chains
    2.3K views
    Pleasure and pain
    00:22
    Pleasure and pain
    863 views
    Pleasure and Pain in a Big Cock Anal Scene
    22:34
    Pleasure and Pain in a Big Cock Anal Scene
    Shemale World
    446 views
    The preparation for the female pain
    05:12
    The preparation for the female pain
    stephanie ka
    1.8K views
    Sissy and the tip
    00:08
    Sissy and the tip
    1.1K views
    Pain for pleasure
    00:25
    Pain for pleasure
    4.3K views
    Cock Punishment
    00:07
    Cock Punishment
    SubmissiveFetish
    1.8K views
    Sissy tortured with wax
    02:59
    Sissy tortured with wax
    Sissy_Nadiene
    1.2K views
    Lizzyyum  August 2024 Masturbate Nipple Pain fantasy bathing pussy clit boobs
    16:58
    Lizzyyum August 2024 Masturbate Nipple Pain fantasy bathing pussy clit boobs
    Lizzy Yum
    624 views
    Lizzyyum VR August 2024 Masturbate Nipple Pain fantasy bathing pussy clit boobs
    16:53
    Lizzyyum VR August 2024 Masturbate Nipple Pain fantasy bathing pussy clit boobs
    Lizzy Yum
    540 views
    Lizzy Yum august 2024 dilate and masturbate #5 nipple pain fantasy bathing pussy clit boobs
    10:12
    Lizzy Yum august 2024 dilate and masturbate #5 nipple pain fantasy bathing pussy clit boobs
    FapHouse
    521 views
    TRANSFIXED - BIG CUMSHOT COMPILATION! CUM SWALLOW, CUM ON FACE, CUM IN MOUTH, CUM ON DICK, & MORE!
    50:49
    TRANSFIXED - BIG CUMSHOT COMPILATION! CUM SWALLOW, CUM ON FACE, CUM IN MOUTH, CUM ON DICK, & MORE!
    Transfixed
    1.4M views
    TSFACTOR Hardcore Trans ANAL Compilation
    23:06
    TSFACTOR Hardcore Trans ANAL Compilation
    TS Factor
    1.2M views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.7M views
    Ladyboys Shemales Cumming With Help
    07:11
    Ladyboys Shemales Cumming With Help
    3.9M views
    Tgirls Closeup Cumshot Compilation for Sissy
    25:07
    Tgirls Closeup Cumshot Compilation for Sissy
    3.5M views
    Compilation: Trannies Cum While they get Fucked
    13:29
    Compilation: Trannies Cum While they get Fucked
    3.9M views
    why do I suddenly love trannys?
    12:46
    why do I suddenly love trannys?
    1.3M views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Painful Compilation

    • Tranny Pussy Tumblr
    • Nomadic Shifters
    • Wife Punishes Husband
    • Men Wearing Sheer Panties
    • Travesti Tocando Punheta Gozando
    • 2 Sissies 1 Chastity Cage
    • Vacuum Bag Bondage
    • Ftm Hairy Pussy Torture
    • Trans Femboy XXX
    • Lesbians Squirting
    • Dj Phuzzy
    • Indonesia Cewek Masturbasi
    • Femboys in Leggings
    • Chubby Crossdresser Spreading the Woods
    • Trap Group
    • Bizarre Extreme
    • Suck My Cock Bitch
    • Me Masturbating 3
    • Hot Mom Anal
    • Desperate to Cum
    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