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

    First Date With A Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    First
    Date
    First Date
    Sissy First
    Sissy Date
    Sissy Crossdresser
    Sissy Training
    Sissy Feminization
    First Time
    Sissy BBC
    Sissy Chastity
    Sissy Husband
    Sissy Compilation
    Sissy Fucked
    Amateur Sissy
    Sissy Blowjob
    Sissy Cuckold
    Sissy Gangbang
    Sissy Slave
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Guy loses bet turns into sissy CD giving blowjob
      04:52
      Guy loses bet turns into sissy CD giving blowjob
      1.3M views
    • First date with a pretty French trans girl, she sucks me and swallows in the kitchen.
      10:46
      First date with a pretty French trans girl, she sucks me and swallows in the kitchen.
      Kern Ostrova
      656.1K views
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3.2M views
    • POV After the First Date with a Trans
      05:23
      POV After the First Date with a Trans
      CaliFauna
      5.8K views
    • Girl forgot to tell her Tinder date that she’s Trans
      07:22
      Girl forgot to tell her Tinder date that she’s Trans
      JsseMontz
      692.2K views
    • I FUCK ON THE FIRST DATE
      07:37
      I FUCK ON THE FIRST DATE
      Third sex XXX
      2.4M views
    • Sissy identity
      08:50
      Sissy identity
      620.2K views
    • Ria Inseminates Ghost Park At Front Door On First Date
      07:05
      Ria Inseminates Ghost Park At Front Door On First Date
      Ria_Bentley
      38.8K views
    • Guy gets fooled into sex with a shemale
      06:15
      Guy gets fooled into sex with a shemale
      Love4TS
      2.7M views
    • Watch Transgirl Ria Bentley Fuck Her 9" Bull on Their First Date
      07:07
      Watch Transgirl Ria Bentley Fuck Her 9" Bull on Their First Date
      Ria_Bentley
      595.8K views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.4M views
    • Tgirl Riley anally used and pleasured on a first date
      01:12:51
      Tgirl Riley anally used and pleasured on a first date
      Tgirl Riley
      149.2K views
    • 3 anal orgasm and hot creampie for skinny trans whore
      16:52
      3 anal orgasm and hot creampie for skinny trans whore
      ActorFab
      2.3M views
    • Our First Date
      05:00
      Our First Date
      Cassandra Lovit
      14.4K views
    • Never Expecting to Be a Sexy Girl
      08:12
      Never Expecting to Be a Sexy Girl
      Pure Ts
      529.7K views
    • POV Taking Cute Sissy's Virginity on the First Date - full vid on LayneLovee Manyvids
      01:20
      POV Taking Cute Sissy's Virginity on the First Date - full vid on LayneLovee Manyvids
      Layne Love
      49.6K views
    • Femboy Crossdresser
      09:57
      Femboy Crossdresser
      1.1M views
    • Dating a mature crossdresser
      08:12
      Dating a mature crossdresser
      Pure Ts
      309.3K views
    • Trust The Fucking Process
      52:41
      Trust The Fucking Process
      1M views
    • Rented Out by His Mistress
      06:12
      Rented Out by His Mistress
      Pure Ts
      113K views
    • Sissy 6
      19:29
      Sissy 6
      1.4M views
    • Relevant Short videos

      Powerful moment from "First date with a pretty French trans girl, she sucks me and swallows in the kitchen."
      Powerful moment from "First date with a pretty French trans girl, she sucks me and swallows in the kitchen."
      Kern Ostrova
      1.1K views
      Emotional moment from "Tgirl Riley anally used and pleasured on a first date"
      Emotional moment from "Tgirl Riley anally used and pleasured on a first date"
      Tgirl Riley
      1.9K views
      Iconic moment from "Tgirl Riley anally used and pleasured on a first date"
      Iconic moment from "Tgirl Riley anally used and pleasured on a first date"
      Tgirl Riley
      1.8K views
      Key moment from "Tgirl Riley anally used and pleasured on a first date"
      Key moment from "Tgirl Riley anally used and pleasured on a first date"
      Tgirl Riley
      1.1K views
      Our First Date
      Our First Date
      Cassandra Lovit
      783 views
      Hazelnut Latte: Got Caught Cheating and Fucking Trans in the Mouth on the First Date - Episode 2
      Hazelnut Latte: Got Caught Cheating and Fucking Trans in the Mouth on the First Date - Episode 2
      Dirty GamesxXx
      453 views
    • Sissyfication
      43:09
      Sissyfication
      1.1M views
    • Taking a straight guy home to turn him into my faggot - Elizabeth Stewart
      08:16
      Taking a straight guy home to turn him into my faggot - Elizabeth Stewart
      Elizabeth Stewart
      451K views
    • shemale dresses sissy to fuck
      16:14
      shemale dresses sissy to fuck
      2.2M views
    • Daddy's Good Girl!
      08:12
      Daddy's Good Girl!
      Pure Ts
      1M views
    • Loser Boyfriend Gets Feminized and Fucked
      08:12
      Loser Boyfriend Gets Feminized and Fucked
      Pure Ts
      328.5K views
    • dominant stepmom helps out her sissy slave
      05:59
      dominant stepmom helps out her sissy slave
      Pure Ts
      420.6K views
    • First Date and First Scene
      06:12
      First Date and First Scene
      Pure Ts
      193.6K views
    • How to Train Your Sissy Boyfriend
      08:12
      How to Train Your Sissy Boyfriend
      Brat Perversions
      149.5K views
    • My stepmom is a tranny
      16:46
      My stepmom is a tranny
      Combat zone transsexual barebacking
      1.3M views
    • crossdresser
      17:56
      crossdresser
      554.8K views
    • Sissy cum dump compilation
      28:49
      Sissy cum dump compilation
      2.8M views
    • shemale
      12:05
      shemale
      2.8M views
    • Sissy CD sucks and is fucked
      08:25
      Sissy CD sucks and is fucked
      1.5M views
    • Bring Us Holes, Silkbone. or We'll Fuck Yours!
      08:12
      Bring Us Holes, Silkbone. or We'll Fuck Yours!
      Mistress Jodie May
      200.5K views
    • He Used to Be the Boss but Not Anymore
      08:12
      He Used to Be the Boss but Not Anymore
      Pure Ts
      527.2K views
    • surprise she has dick
      07:34
      surprise she has dick
      264.8K views
    • Feminization Positivity Trainer
      03:20
      Feminization Positivity Trainer
      729.8K views
    • family fun 1.mp4
      13:05
      family fun 1.mp4
      1.8M views
    • Hot T GIRL with college boy.
      29:02
      Hot T GIRL with college boy.
      3M views
    • Dads Bestmate Bangs Femboy
      05:11
      Dads Bestmate Bangs Femboy
      mothplayboy
      936.9K views
    • CD TRAP SISSY EDUCATION TRAINING 101
      01:27:33
      CD TRAP SISSY EDUCATION TRAINING 101
      975.7K views
    • A guide to sissication: Beginner - Am I a sissy?
      23:32
      A guide to sissication: Beginner - Am I a sissy?
      798.2K views
    • I turned my straight roommate intro trans wife
      05:20
      I turned my straight roommate intro trans wife
      CutePinkUnicorn
      616.1K views
    • He filled my ass with it, his drips a lot
      07:53
      He filled my ass with it, his drips a lot
      Piou_Sissy
      360.7K views
    • Crossdressing superstar visits the site
      06:40
      Crossdressing superstar visits the site
      Pure Ts
      118.8K views
    • Sissy Slut Motel
      58:39
      Sissy Slut Motel
      760.1K 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 Date With A Sissy

    First Time Crossdressing for Friend
    Crossdresser Seducing a Straight Guy
    First Time Sissy
    First Time Tranny
    Fucking a Sissy Femboy
    Mature Crossdresser With Straight Guy
    Cute Sissy Femboy
    First Time With Trans
    Sissy Femboy Fucked
    Straight Guys Fuck Crossdresser
    Straight Guys Fantasy
    Straight Guy Tricked by Tranny
    Traps Femboys and Sissys
    Femboy Schoolgirl
    First Trans Experience
    Secret Sissyboy
    Crossdresser With Her Grindr Date
    Cute Sissy
    Trans Teen in Tiny Skirt
    My First Shemale
    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