PornPorn US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
      -60%
    • Sex Chat Nude Chat
    • Pornstars
    • Channels
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday Sale

    First Time Pain Anal Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Anal
    First
    Pain
    Time
    First Time Anal
    First Time Pain
    First Time
    First Anal
    Anal Pain
    Anal First
    Anal Time
    First Pain
    First Time Indian Anal Pain
    Asian First Time Anal Pain
    First Time Monster Cock Anal Pain
    Virgin First Time
    Mature Anal
    Amateur Anal
    Granny Anal
    Teen Anal
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • painful anal
      05:26
      painful anal
      1.4M views
    • New bitch hard-core backhole sex rapidly after doggy style first time pain coming
      07:47
      New bitch hard-core backhole sex rapidly after doggy style first time pain coming
      Riya babe
      94.2K views
    • First time anal fucking compilation
      10:57
      First time anal fucking compilation
      Ben Dover Movies
      5.7M views
    • Shy Girlfriend First Time Anal Experience
      06:49
      Shy Girlfriend First Time Anal Experience
      Kingsizedevil
      508.5K views
    • Blackmailed Crying Anal
      05:14
      Blackmailed Crying Anal
      912.8K views
    • Amateur wife gets fucked in anal first time - Homemade painal
      17:08
      Amateur wife gets fucked in anal first time - Homemade painal
      JadeKink.com
      298.2K views
    • Penetrate her ass for the first time
      04:24
      Penetrate her ass for the first time
      702K views
    • Stepsister and Stepbrother hard Anal fuck, first time painful anal sex
      09:56
      Stepsister and Stepbrother hard Anal fuck, first time painful anal sex
      Billogulnaz
      3.8M views
    • Jasmin Aviafan's First Anal Adventure
      09:34
      Jasmin Aviafan's First Anal Adventure
      Anal Coach
      183K views
    • Step Daddy Prepares Me For The First Time Anal
      09:30
      Step Daddy Prepares Me For The First Time Anal
      AmyHi
      15.7M views
    • Extreme Squirting, FIRST ANAL FUCK too painful
      15:07
      Extreme Squirting, FIRST ANAL FUCK too painful
      NickyGold
      1.2M views
    • Viral Pakistani 18 year Tiktoker pathani girl first time Anal sex her big ass pain'
      07:46
      Viral Pakistani 18 year Tiktoker pathani girl first time Anal sex her big ass pain'
      Kingsizedevil
      608.3K views
    • Real Extreme – Most Painful First Anal Sex Of Cute Teen Girl
      24:47
      Real Extreme – Most Painful First Anal Sex Of Cute Teen Girl
      Stacy Starando
      1.2M views
    • BedPost Fetishes. First Time Anal Bed Post Insertion for Super Tight Anal
      09:28
      BedPost Fetishes. First Time Anal Bed Post Insertion for Super Tight Anal
      Toystest
      172.1K views
    • Extremely painful first time anal sex for a teen. This way it really hurts, this is not the right way to deflower an asshole.
      11:31
      Extremely painful first time anal sex for a teen. This way it really hurts, this is not the right way to deflower an asshole.
      Fucktotum
      3.4M views
    • mega squirt through first time anal sex
      05:16
      mega squirt through first time anal sex
      littlejolieroux
      2.7M views
    • Anal so painful it made her literally cry - a bad girl needed to be punished
      04:31
      Anal so painful it made her literally cry - a bad girl needed to be punished
      Jack smith
      762.6K views
    • Desi step Brother and step Sister first time painful Sex
      07:05
      Desi step Brother and step Sister first time painful Sex
      BD_Village_couple
      5.3M views
    • Oh no!!!! That's the my asshole, please don't put it in there!!! it Hurts!!!!
      06:38
      Oh no!!!! That's the my asshole, please don't put it in there!!! it Hurts!!!!
      Sex_associates
      1.5M views
    • When I fucked her ass first time, she was crying.
      16:24
      When I fucked her ass first time, she was crying.
      Topxxxcouple
      9.7M views
    • Painful anal fuck - scream and cry
      04:40
      Painful anal fuck - scream and cry
      2.7M views
    • Teen step Sister gets her Ass and Pussy Fucked by bro, first time painful anal sex
      07:02
      Teen step Sister gets her Ass and Pussy Fucked by bro, first time painful anal sex
      Billogulnaz
      9.5M views
    • Innocent teen cutie gets her virgin ass pounded first time.
      13:43
      Innocent teen cutie gets her virgin ass pounded first time.
      First Anal Quest
      3.4M views
    • First time anal. Real suffering and real pleasure! AnnAngle and AmateurSphere in action.
      08:00
      First time anal. Real suffering and real pleasure! AnnAngle and AmateurSphere in action.
      AmateurSphere
      403.1K views
    • Brutal Anal Sex, Screaming & Begging, But Wont Stop Till Finish
      11:35
      Brutal Anal Sex, Screaming & Begging, But Wont Stop Till Finish
      Fat Goddes
      705K views
    • First Time Painful Tight Ass Fucking Step Sister and Step Brother, hindi anal sex
      11:05
      First Time Painful Tight Ass Fucking Step Sister and Step Brother, hindi anal sex
      Billogulnaz
      10.1M views
    • FIRST TIME PAINFUL ANAL for 18yo barely legal teen – ANAL DEFLORATION: it hurts like hell. Finally my gf lets me fuck he
      05:06
      FIRST TIME PAINFUL ANAL for 18yo barely legal teen – ANAL DEFLORATION: it hurts like hell. Finally my gf lets me fuck he
      Fucktotum
      2.8M views
    • Teen step Sister gets her Ass and Pussy Fucked by stepbrother, first time painful anal sex
      06:24
      Teen step Sister gets her Ass and Pussy Fucked by stepbrother, first time painful anal sex
      Billogulnaz
      4.4M views
    • Virgin Asshole is the BEST Asshole - I think she likes it!
      45:06
      Virgin Asshole is the BEST Asshole - I think she likes it!
      3.3M views
    • She Asked Me To Put My Big Dick In Her Ass First Time
      09:56
      She Asked Me To Put My Big Dick In Her Ass First Time
      408.4K views
    • 18yo girl squeals and sobs when a fat dick enters her anus!
      05:37
      18yo girl squeals and sobs when a fat dick enters her anus!
      270.8K views
    • Her first time fucked
      08:12
      Her first time fucked
      Kink
      380K views
    • Does it hurt - Yes. Do you want me to stop - No.
      12:13
      Does it hurt - Yes. Do you want me to stop - No.
      Sex_associates
      461.3K views
    • Old MILF stepmom gets a BIG Cock in the ass for the first time, she loved ANAL creampie
      11:03
      Old MILF stepmom gets a BIG Cock in the ass for the first time, she loved ANAL creampie
      Ciena
      779.4K views
    • Amateur first anal
      05:15
      Amateur first anal
      3.4M views
    • First time anal sex with her cousin started crying in pain cousin desixxx
      15:16
      First time anal sex with her cousin started crying in pain cousin desixxx
      wildDesipair
      3.3M views
    • Surprise Anal - She did not enjoy it!
      03:13
      Surprise Anal - She did not enjoy it!
      1.2M views
    • SensualBB2
      Online
      SensualBB2
    • Ivy Winterz FIRST Time doing Anal "ouch that Hurts!''
      19:39
      Ivy Winterz FIRST Time doing Anal "ouch that Hurts!''
      Ivy winterz
      1.6M views
    • Painal!! Real anal virgin.. 18+ teen first anal fuck at home by stepdad
      06:02
      Painal!! Real anal virgin.. 18+ teen first anal fuck at home by stepdad
      Skyy
      199.5K views
    • Virgin ass fucking first time, indian ass fucking,anal fucking painfull video
      05:41
      Virgin ass fucking first time, indian ass fucking,anal fucking painfull video
      Sexy_girl_nehu
      3.7M views
    • first time anal , painful anal sex, homemade
      09:47
      first time anal , painful anal sex, homemade
      FlorLex2022
      27.8K views
    • First time Anal fuck my new married girlfriend so Hard & painful crying my Girlfriend
      07:46
      First time Anal fuck my new married girlfriend so Hard & painful crying my Girlfriend
      CRAZY-XYZ
      2.7M views
    • TeensLoveAnal - Compilation Of Painful Anal Sex
      30:16
      TeensLoveAnal - Compilation Of Painful Anal Sex
      Team Skeet
      2.6M views
    • LoL butt plug painal first time deep anal creampie
      10:23
      LoL butt plug painal first time deep anal creampie
      Sparowdox
      336.1K views
    • Painal - Unboxing Teen’s Tight Asshole - Anal Creampie
      04:47
      Painal - Unboxing Teen’s Tight Asshole - Anal Creampie
      MaryCandy
      669.9K views
    • First time painful anal
      11:59
      First time painful anal
      Ebony Legeng
      471.8K views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80

    Searches Related to First Time Pain Anal

    • Pain Anal Amateur First Homemade
    • Not in My Ass Please It Hurts
    • Painful Assfuck of Wife
    • No Mercy Painal
    • Too Big Crying
    • Real Amateur First Time Anal
    • Very Tight Asshole
    • Omg Wrong Hole Fucking
    • It Feels so Good in My Ass
    • She Cant Handle the Dick She Cry
    • Broken Asshole
    • Wife Punished Anally
    • Sodomie Surprise
    • Huge Cock Hurts
    • Brutal Painal Surprise
    • Can T Pay
    • Old Woman Cry Rough
    • Painful Sex and Loud Moaning
    • Home Made Painal
    • Young Pain
    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