PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    ❄️ GOODBYE, WINTER! 🌞 Hello, Big Savings on Faphouse 🎉

    First Sex Pain Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Selfuking
      04:12
      Selfuking
      Papiricoo
      40.3K views
    • First experience
      51:56
      First experience
      3.1M views
    • Trans Girl plays with an 18 cm Dildo for the first time, Moans from pain but ends up liking it  Succubo16
      29:58
      Trans Girl plays with an 18 cm Dildo for the first time, Moans from pain but ends up liking it Succubo16
      LaRicura16
      12K views
    • First Time Glory Hole
      09:03
      First Time Glory Hole
      468.9K views
    • First try for new plug and a bit bigger
      01:28
      First try for new plug and a bit bigger
      Sanne
      9.7K views
    • My first sex with a Ladyboy
      20:22
      My first sex with a Ladyboy
      1.2M views
    • Hung Ts Aakosha Bentley makes her sub scream in pain
      02:03
      Hung Ts Aakosha Bentley makes her sub scream in pain
      937.3K views
    • Try something new
      01:00
      Try something new
      347.3K 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
      266.3K views
    • ioioioioi
      08:39
      ioioioioi
      501.6K views
    • The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded
      10:53
      The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded
      alinanightsky
      287.6K views
    • When she can't pull out
      01:26
      When she can't pull out
      505.1K views
    • Caning and choking Kitsy
      04:56
      Caning and choking Kitsy
      Kitsy Meow
      78.7K views
    • FIRST MEET
      19:38
      FIRST MEET
      312.1K views
    • Anal fist fuck faggot love to feel the pain in the ass
      18:18
      Anal fist fuck faggot love to feel the pain in the ass
      Nicole Montero
      146.8K views
    • First timer can't take it at first try, then he takes it all
      02:20
      First timer can't take it at first try, then he takes it all
      1.9M views
    • 25 min of abuse and hard use for the pain whore Alina
      03:04
      25 min of abuse and hard use for the pain whore Alina
      alinanightsky
      56.2K views
    • Her first time
      01:18
      Her first time
      313.7K views
    • HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-
      31:02
      HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-
      111.5K views
    • What Her Name Pls! thank
      05:00
      What Her Name Pls! thank
      1.5M views
    • Redhead Asian shemale all covered in pain gets fucked
      07:10
      Redhead Asian shemale all covered in pain gets fucked
      Extreme Ladyboys
      76.2K views
    • Losing my virginity to a TS
      03:53
      Losing my virginity to a TS
      3.8M views
    • 116 min degrading of bdsm sissy pain whore Alina
      02:20
      116 min degrading of bdsm sissy pain whore Alina
      alinanightsky
      82.5K views
    • Trust The Fucking Process
      52:41
      Trust The Fucking Process
      1.1M views
    • How a Tgirl severely punishs her big cock.
      10:29
      How a Tgirl severely punishs her big cock.
      MyLolaTrav
      45.1K views
    • Your First Time Getting Fucked by a Trans Girl: First Date GFE POV Femdom
      06:31
      Your First Time Getting Fucked by a Trans Girl: First Date GFE POV Femdom
      Melissa Masters
      602.2K 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
      30.4K views
    • First sex with trans
      04:51
      First sex with trans
      2M views
    • How to torture a beautiful sissy cock
      09:59
      How to torture a beautiful sissy cock
      MyLolaTrav
      28.7K views
    • my first date with a transgender girl.
      18:03
      my first date with a transgender girl.
      710.1K views
    • My patient was complaining of pain in his leg, so I treated him to butt tea at my office desk
      06:06
      My patient was complaining of pain in his leg, so I treated him to butt tea at my office desk
      Nathalia Fontes
      115.3K views
    • Mmmm x
      56:19
      Mmmm x
      1.2M views
    • First Date and First Scene
      06:12
      First Date and First Scene
      Pure Ts
      198.4K views
    • Ruthless TS turns guy into her little bitch
      03:44
      Ruthless TS turns guy into her little bitch
      2.7M views
    • Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time - Trans Angels
      10:25
      Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time - Trans Angels
      Trans Angels
      9.5M views
    • I had my first sex, he came inside me :(
      05:08
      I had my first sex, he came inside me :(
      cd_aysemmm
      141.5K views
    • Morning Surprise Wife Has a Dick and Knows How to Use It
      07:14
      Morning Surprise Wife Has a Dick and Knows How to Use It
      Marvellee
      15.2M views
    • First Time Anal
      08:41
      First Time Anal
      Pure Ts
      111.9K views
    • Long Anal Session for Hurting Emma Tied to the Bench
      01:05:06
      Long Anal Session for Hurting Emma Tied to the Bench
      ActorFab
      323.9K views
    • When preventive check-up gone wrong..
      01:13
      When preventive check-up gone wrong..
      Twistedrama
      24.6K views
    • premature
      01:41
      premature
      150.4K views
    • Fucked from behind
      02:24
      Fucked from behind
      512.6K views
    • kerri's 1st Grindr fuck (festival edition)
      05:54
      kerri's 1st Grindr fuck (festival edition)
      183.2K views
    • FEMBOYISH - FEMBOY JAKE WILD COMPILATION PART 1! WITH HARRISON FEELS, ETHAN CHASE, & PAPI SANTIAGO
      46:20
      FEMBOYISH - FEMBOY JAKE WILD COMPILATION PART 1! WITH HARRISON FEELS, ETHAN CHASE, & PAPI SANTIAGO
      ADULTTIMEGAY
      198.9K views
    • Futanaria - Bed
      24:52
      Futanaria - Bed
      9.8M views
    • Anal destruction for stupid maso whore
      35:04
      Anal destruction for stupid maso whore
      ActorFab
      768.7K views
    • my first experience with indian lady boy hardcore chudai with clear hindi audio
      20:12
      my first experience with indian lady boy hardcore chudai with clear hindi audio
      Raj00
      1.8M views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80
    Categories
    American
    4K Porn
    HD Videos
    VR Porn
    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
    Bareback
    Creampie
    Cumshot
    Mature
    Homemade
    Teen
    Anal
    Masturbation
    Domination
    Transgender
    Asian
    Solo
    BBW
    Brazilian
    Cartoon
    Mexican
    Interracial
    Vintage
    Big Tits
    Young
    Japanese
    Trans Woman
    Threesome
    Small Cock
    Lingerie
    Gangbang
    Thai
    Petite
    Colombian
    BDSM
    Public
    MILF
    Couple
    Rough Sex
    Anal Masturbation
    Stockings
    Dildo
    Babysitter
    POV
    Cuckold
    Small Tits
    Outdoor
    Trans Man
    Handjob
    Hentai
    FTM
    Group Sex
    Indian
    Fetish
    Chinese
    Massage
    Bondage
    Pissing
    Double Penetration
    English
    Role Play
    Behind The Scenes
    Anal Toy
    British
    SFW
    All categories
    Monetize your content
    Become a creator
    xHamster
    • About us
    • 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
    Earn money with us
    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    © 2026 xHamster - Free porn videos.
    Desktop 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