PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    ICE MELTING SALE — 50% OFF 🧊🔥 Limited-time deal

    Sissy Date Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Date
    First Date With a Sissy
    Sissy Boy Gets Fucked Tinder Date
    Sissy Crossdresser
    Sissy Training
    Sissy Feminization
    Sissy BBC
    Sissy Chastity
    Sissy Husband
    Sissy Compilation
    Sissy Fucked
    Sissy Blowjob
    Amateur Sissy
    Sissy Gangbang
    Sissy Slave
    Sissy Cuckold
    Sissy Boy
    Sissy Femdom
    Sissy Slut
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Latina Shemale Masturbates During a Date Tight Asshole of Guys with Toy
      10:36
      Latina Shemale Masturbates During a Date Tight Asshole of Guys with Toy
      FapHouse
      618 views
    • Fantasy Dating: Futa Ladyboy With Big Cock Fucks Is Having Sex With Sexy MILF For The First Time Part 6
      08:12
      Fantasy Dating: Futa Ladyboy With Big Cock Fucks Is Having Sex With Sexy MILF For The First Time Part 6
      FapHouse
      1.1K views
    • Cute Trannys Sex on the First Date
      22:13
      Cute Trannys Sex on the First Date
      83.4K views
    • Torrid Date With Redhead Trans Beauty Bianca Ruiva
      08:26
      Torrid Date With Redhead Trans Beauty Bianca Ruiva
      Dream Tranny
      31.8K views
    • Dream date
      01:39
      Dream date
      20.2K views
    • Lunch Date 5-8-19
      01:02
      Lunch Date 5-8-19
      10.9K views
    • Dinner is served, hot date with Tina Torride in the kitchen
      00:52
      Dinner is served, hot date with Tina Torride in the kitchen
      6.2K views
    • Michele Is Waiting For A Date POV
      04:00
      Michele Is Waiting For A Date POV
      Michele Thompson
      8K views
    • First minutes of a sex date
      06:26
      First minutes of a sex date
      13.3K views
    • Shemale date gives a head and then getting drilled
      06:16
      Shemale date gives a head and then getting drilled
      4K views
    • Hot date with XHamster Tgirl Kim Latino
      00:44
      Hot date with XHamster Tgirl Kim Latino
      5.9K views
    • Shemale having anal sex with her new date
      05:24
      Shemale having anal sex with her new date
      2.7K views
    • Prep Sex Date with My Giant Soldier Owner of 24 Cm Bwc Feeding My Mouth and Later My Bubble Ass Bare Backing
      06:59
      Prep Sex Date with My Giant Soldier Owner of 24 Cm Bwc Feeding My Mouth and Later My Bubble Ass Bare Backing
      FapHouse
      2K views
    • Slim blond ts loves deep anal with her date
      05:35
      Slim blond ts loves deep anal with her date
      2.7K views
    • Ebony ts has cock 2 cock and anal with her date
      07:13
      Ebony ts has cock 2 cock and anal with her date
      2.4K views
    • Iyuton daw ko unya hinig human og ligo para fresh ang dating
      27:10
      Iyuton daw ko unya hinig human og ligo para fresh ang dating
      Reynaldo6
      3.2K views
    • Fucm my date has an little cock
      39:51
      Fucm my date has an little cock
      FapHouse
      2.1K views
    • Lizzy Yum VR - JUST BEFORE DATE BF Post-op Orgasm Pussy Clit Masturbation Teasing Orgasm
      14:43
      Lizzy Yum VR - JUST BEFORE DATE BF Post-op Orgasm Pussy Clit Masturbation Teasing Orgasm
      FapHouse
      5.3K views
    • Dating fantasy gameplay part 1
      05:28
      Dating fantasy gameplay part 1
      Amaran
      2.1K views
    • Dating fantasy gameplay part 4
      06:53
      Dating fantasy gameplay part 4
      Amaran
      1.1K views
    • Fantasy Dating: Futanari On The Bed Part 7
      06:02
      Fantasy Dating: Futanari On The Bed Part 7
      FapHouse
      584 views
    • Cute Tgurl goes on a date
      06:32
      Cute Tgurl goes on a date
      55.7K views
    • Date with a Schwyzer T-Girl
      24:01
      Date with a Schwyzer T-Girl
      41.7K views
    • Hot dates
      12:55
      Hot dates
      48.1K views
    • Nice date with mature sexy slut.
      00:57
      Nice date with mature sexy slut.
      35.7K views
    • MY FIRST EXCITING DATE
      01:08
      MY FIRST EXCITING DATE
      32K views
    • Hot Thai tsgirl anal with her horny date
      06:08
      Hot Thai tsgirl anal with her horny date
      15.9K views
    • horny date! Betty B
      01:53
      horny date! Betty B
      7.6K views
    • Hot date with XHamster Tgirl Kim Latino
      00:53
      Hot date with XHamster Tgirl Kim Latino
      12.4K views
    • A date with Victoria huge cock
      01:27
      A date with Victoria huge cock
      7.4K views
    • Busty latina TS analed her fat guy date
      10:06
      Busty latina TS analed her fat guy date
      4.2K views
    • Date with Meli Melicious (The Beginning)
      00:32
      Date with Meli Melicious (The Beginning)
      5.8K views
    • Latin shemale punishes her submissive date in the ass
      04:06
      Latin shemale punishes her submissive date in the ass
      10.5K views
    • Hoseman Date Night time to go and suck & fuck!
      05:10
      Hoseman Date Night time to go and suck & fuck!
      5.5K views
    • Savannah's bad date night
      00:34
      Savannah's bad date night
      5.3K views
    • Just up-to-date dressing & playing on cam
      07:57
      Just up-to-date dressing & playing on cam
      12.4K views
    • Busty Blonde Shemale Casey Kisses date with a dick suck
      05:20
      Busty Blonde Shemale Casey Kisses date with a dick suck
      4.3K views
    • GROOBYVR: Lunch Date with Nikki Vicious
      00:30
      GROOBYVR: Lunch Date with Nikki Vicious
      Grooby VR
      8.9K views
    • Young tranny has her ass stretched by her date
      05:20
      Young tranny has her ass stretched by her date
      4.3K views
    • I dressed as a hot girl for a hot date
      00:47
      I dressed as a hot girl for a hot date
      Onlyfans
      6.4K views
    • Something requested of me on a dating app.
      03:26
      Something requested of me on a dating app.
      5.2K views
    • Cam Date
      03:54
      Cam Date
      1.8K views
    • Transsexual Lorena Lopes Has a Date With a Machine
      15:10
      Transsexual Lorena Lopes Has a Date With a Machine
      Dream Tranny
      1.8K views
    • What a nice date
      00:46
      What a nice date
      1.6K views
    • The Girl Really Waits When Daddy Dates Because He Will Have Hard Sex
      51:17
      The Girl Really Waits When Daddy Dates Because He Will Have Hard Sex
      FapHouse
      2.3K views
    • Tranny blowing her date and fucked in her ass
      05:29
      Tranny blowing her date and fucked in her ass
      2.4K views
    • Crossdressing Cindy getting ready for her first date
      01:16
      Crossdressing Cindy getting ready for her first date
      Cindylov
      2K views
    Previous page
    Next page
    1
    1. 1
    2. ...
    3. 5
    4. ...
    5. 8
    6. 9
    7. 10
    8. 11
    9. 12
    10. ...
    11. 45
    12. ...
    13. 80
    80

    Searches Related to Sissy Date

    • Thigh Gap
    • Role Reversal
    • Spy
    • Transsexuals
    • Bullied
    • Familyxxx HD
    • Humiliated
    • Sweet Sissy87
    • White Lingerie
    • Fainting Orgasms
    • Pure TS List
    • School Uniform
    • Dating
    • Lovely Lovely
    • Hot Mom Doggy
    • Sissychristine
    • Barebacked
    • Sissyjay
    • Hotel Room
    • French Kissing
    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