PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels

    Milf Date Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Tranny Surprises Her Date
    Shemale and MILF Threesome
    Shemale Fucks MILF Anal
    Shemale Fucks Lesbian MILF
    Milf Shemale Big Cock
    Milf Shemale Fucks Guy
    Big Boobs MILF Milk
    Milf Pegging Her Trans
    Dating With a Black Shemale
    First Date With a Sissy
    Mature Crossdresser Hotel Sex Date
    Crossdresser With Her Grindr Date
    Ts Trap Sissy Date Hike
    Tinder Date Crossdress Top Guy
    Transgender Dates in Orlando Backpage
    Pattaya Ladyboy Ae Hotel Date
    Milf Sucks Tranny's Cock
    Trap Web Series Indian MILF
    Sexy Kashmiri MILF Mishal Malik
    I Fuck on the First Date
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • BLACK-TGIRLS: Date Night With Akaya Prime
      03:11
      BLACK-TGIRLS: Date Night With Akaya Prime
      Black Tgirls
      40.1K views
    • Pretty tranny gets her mouth fucked by Grindr Date
      02:04
      Pretty tranny gets her mouth fucked by Grindr Date
      69.6K views
    • Busty shemale throat fucking her date
      06:04
      Busty shemale throat fucking her date
      61.1K views
    • VRB Trans Isabella Fontanelli fuck date with a tranny from the app VR Porn
      06:11
      VRB Trans Isabella Fontanelli fuck date with a tranny from the app VR Porn
      VRbtrans
      42.8K views
    • Come Inside If You Really Wanna Date Me
      12:55
      Come Inside If You Really Wanna Date Me
      Devils tgirls
      119.6K views
    • Crossdresser Getting Ready for Date with Hot Man
      01:25
      Crossdresser Getting Ready for Date with Hot Man
      Bailey Wilde
      35K views
    • We're Talking about Our Neighbours and Dates
      07:30
      We're Talking about Our Neighbours and Dates
      Asura
      6.4K views
    • My big ass fucked by grindr date
      01:58
      My big ass fucked by grindr date
      49.9K views
    • Date with Super Skinny Ig Ladyboy Ends up with Horny Banging
      08:00
      Date with Super Skinny Ig Ladyboy Ends up with Horny Banging
      TRANS in Asia
      8.9K views
    • Hot sex with a Tinder date
      12:52
      Hot sex with a Tinder date
      154.9K views
    • Sissy slut sissygasm and plays with Ai waiting for grindr date
      07:24
      Sissy slut sissygasm and plays with Ai waiting for grindr date
      OneWhoHasFun
      6.6K views
    • First Shemale Date Ends Up Deep Anal Sex
      06:15
      First Shemale Date Ends Up Deep Anal Sex
      87.3K views
    • Hot Big Tit Tranny Fucked Hard Anally in a Hotel on a Date
      08:37
      Hot Big Tit Tranny Fucked Hard Anally in a Hotel on a Date
      Shemale TS Collection
      1.8K views
    • Ladyboystar - Hot Date with a Cute Ladyboy Who Loves Makeup and Changing Clothes
      02:24
      Ladyboystar - Hot Date with a Cute Ladyboy Who Loves Makeup and Changing Clothes
      Ladyboy Star
      2.1K views
    • Date with a Watermelon
      05:11
      Date with a Watermelon
      268.7K views
    • TSVirtualLovers - Dating a Tranny
      06:58
      TSVirtualLovers - Dating a Tranny
      TS Virtual Lovers
      119.4K views
    • Hot Blonde Shemale Fucked Outdoors in Tight Asshole During Date
      27:34
      Hot Blonde Shemale Fucked Outdoors in Tight Asshole During Date
      Shemale TS Collection
      1.3K views
    • Tinder Date Gets Anal Fucked Outdoors by a Naughty Tranny and Receives a Cumshot
      22:39
      Tinder Date Gets Anal Fucked Outdoors by a Naughty Tranny and Receives a Cumshot
      Shemale TS Collection
      1.7K views
    • Masturbating after date with trans woman
      10:06
      Masturbating after date with trans woman
      1.1K views
    • Thick shemale loves anal sex with her date
      07:10
      Thick shemale loves anal sex with her date
      48.4K views
    • Sergeant Miles enjoys his first TRANS date with inked hottie
      06:16
      Sergeant Miles enjoys his first TRANS date with inked hottie
      99K views
    • date
      10:40
      date
      36.3K views
    • trio date.
      06:36
      trio date.
      40.3K views
    • Tinder date-stranger-BB- creamppie CD
      09:41
      Tinder date-stranger-BB- creamppie CD
      165.9K views
    • GenderX - Hot Blonde Gives Date His First Trans Experience
      11:56
      GenderX - Hot Blonde Gives Date His First Trans Experience
      GenderX
      94.5K views
    • Transsexual Date Ends Up In The Bed
      06:13
      Transsexual Date Ends Up In The Bed
      48.9K views
    • Sexy Asian Shemale From Tinder Date Fucked Anally in a Hotel
      08:12
      Sexy Asian Shemale From Tinder Date Fucked Anally in a Hotel
      Shemale TS Collection
      763 views
    • Date in Hotel and Cum
      03:02
      Date in Hotel and Cum
      Milady Silvia Helena
      9.1K views
    • Hot Blonde Big Tit Shemale Gets Anal Fucked by Strangers on Their First Date
      17:46
      Hot Blonde Big Tit Shemale Gets Anal Fucked by Strangers on Their First Date
      Shemale TS Collection
      1.5K views
    • Shemale drills white guy on date
      06:10
      Shemale drills white guy on date
      17.1K views
    • Crossdresser Before and After Date
      01:00
      Crossdresser Before and After Date
      Bailey Wilde
      18.5K views
    • Getting to Know Each Other - Closely! Fucking on the First Date
      00:41
      Getting to Know Each Other - Closely! Fucking on the First Date
      Emily Adaire
      8.6K views
    • Hardcore Date with a Bored Student Ladyboy
      08:00
      Hardcore Date with a Bored Student Ladyboy
      TRANS in Asia
      4.6K views
    • Latina Ladyboy From Tinder Date Fucked in Tight Asshole Outdoors
      23:31
      Latina Ladyboy From Tinder Date Fucked in Tight Asshole Outdoors
      Shemale TS Collection
      1.6K views
    • Futa Dating Simulator 6 Gloria Is a Lawyer Who Love Fucking but Not Getting Fucked
      28:36
      Futa Dating Simulator 6 Gloria Is a Lawyer Who Love Fucking but Not Getting Fucked
      Johannesgaming
      1.1K views
    • VRBTRans Hot Date With Alyssa And Her Naughty Sex Games
      06:01
      VRBTRans Hot Date With Alyssa And Her Naughty Sex Games
      VRbtrans
      97.9K views
    • OOPSIE - We Had An Amazing Bisexual Threesome In An Empty Movie Theater Room During A Throuple Date
      10:05
      OOPSIE - We Had An Amazing Bisexual Threesome In An Empty Movie Theater Room During A Throuple Date
      AdultTime
      13.6K views
    • Jammi Cummings on Grindr date gone wild
      23:03
      Jammi Cummings on Grindr date gone wild
      17.4K views
    • TrannyPros Candy Marie Wants to Fuck her Man B4 Date Night!
      10:01
      TrannyPros Candy Marie Wants to Fuck her Man B4 Date Night!
      Devils tgirls
      101.1K views
    • fuck with a date
      00:34
      fuck with a date
      38.1K views
    • My first date with Adele, part 4...
      01:34
      My first date with Adele, part 4...
      76.2K views
    • Crossdresser Getting Ready for Date with Hot Man
      01:25
      Crossdresser Getting Ready for Date with Hot Man
      Bailey Wilde
      53.4K views
    • Sissy Slut Michelle in a New Lingerie Preparing Before a Date in a Hotel of Turkish Bodrum
      28:30
      Sissy Slut Michelle in a New Lingerie Preparing Before a Date in a Hotel of Turkish Bodrum
      Michael Ernandes
      5.1K views
    • She fucks on first date
      26:13
      She fucks on first date
      105.1K views
    • What should i wear for our date tonight?
      13:58
      What should i wear for our date tonight?
      Anna Rios
      25.2K views
    • Hot Anal Date With Gorgeous Ts Foxxy And With
      04:51
      Hot Anal Date With Gorgeous Ts Foxxy And With
      9.3K views
    • Guy Fucks Blonde Skinny Shemale on First Date Outdoors
      26:04
      Guy Fucks Blonde Skinny Shemale on First Date Outdoors
      Shemale TS Collection
      1.1K views
    Previous page
    Next page
    1
    1. 1
    2. ...
    3. 5
    4. 6
    5. 7
    6. 8
    7. 9
    8. ...
    9. 44
    10. ...
    11. 80
    80

    Searches Related to Milf Date

    • Shy Wife Shared
    • Milf
    • Stepson
    • Sisters
    • Mature Wife Shared
    • Ts Stepdaughter
    • Best Love
    • Lesbian Mom
    • First Time Sucking
    • Step Brother Cum Inside Step Sister
    • Milf 300
    • Chubby Mom Fucking
    • Family Sex
    • Milf With Young Couple
    • Sissy Fuck
    • Wife Fuck Husband
    • Sissy Daddy
    • Tattoo
    • Step Sister XXX
    • Fucks MILF
    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