PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    LET IT SNOW, LET IT SAVE! ☃️ Faphouse Discounts – Winter Edition

    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 Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Sissy Blowjob
    Sissy Slave
    Sissy Gangbang
    Amateur Sissy
    Sissy Cuckold
    Sissy Femdom
    Sissy Slut
    Sissy Boy
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • TS TRAP SISSY DATE HIKE
      06:16
      TS TRAP SISSY DATE HIKE
      1.3M views
    • White Sissy Date with BBC
      01:25
      White Sissy Date with BBC
      17K views
    • MsMarcy sissy date night
      00:50
      MsMarcy sissy date night
      Msmarcy
      3.9K views
    • Little black dress sissy date night
      00:50
      Little black dress sissy date night
      964 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
      643.5K views
    • Dating a mature crossdresser
      08:12
      Dating a mature crossdresser
      Pure Ts
      254K 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
      615.1K views
    • I FUCK ON THE FIRST DATE
      07:37
      I FUCK ON THE FIRST DATE
      Third sex XXX
      2.3M views
    • German anal tranny date outdoor on holiday in Mallorca
      17:26
      German anal tranny date outdoor on holiday in Mallorca
      EroCom
      466.8K views
    • Date Night with Mature Crossdresser
      08:12
      Date Night with Mature Crossdresser
      Pure Ts
      215.5K 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
      575.7K views
    • Ria Bentley Gets Impregnated by Her 10" Bull Date
      21:12
      Ria Bentley Gets Impregnated by Her 10" Bull Date
      FapHouse
      210.1K views
    • Intense Passionate Kissing & Makeout Foreplay on Date Night with this GORGEOUS Black Trans Girl Eros Orisha
      08:13
      Intense Passionate Kissing & Makeout Foreplay on Date Night with this GORGEOUS Black Trans Girl Eros Orisha
      K KirkRyner
      170.3K views
    • Our First Date
      05:00
      Our First Date
      Cassandra Lovit
      11.6K 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
      135.8K views
    • Sissy Doll Fucking in a Pegging Date
      07:00
      Sissy Doll Fucking in a Pegging Date
      Brat Perversions
      19.1K views
    • Humiliating Date Story by a Pathetic Piggy
      14:11
      Humiliating Date Story by a Pathetic Piggy
      FapHouse
      18.5K views
    • Sexy Tgirl shoots a lot of cum while getting fucked bare on date #5
      01:02:22
      Sexy Tgirl shoots a lot of cum while getting fucked bare on date #5
      Tgirl Riley
      152.1K views
    • German amateur homemade anal creampie sex date with teen shemale
      12:18
      German amateur homemade anal creampie sex date with teen shemale
      EroCom
      831.6K views
    • Tgirl Riley getting fucked bare in Date #6 PartII
      55:16
      Tgirl Riley getting fucked bare in Date #6 PartII
      Tgirl Riley
      166.1K views
    • Gina ́s New Year's Date
      09:40
      Gina ́s New Year's Date
      Strapsex
      114.3K views
    • Relevant Short videos

      Ria Bentley Gets Impregnated by Her 10" Bull Date
      Ria Bentley Gets Impregnated by Her 10" Bull Date
      Ria_Bentley
      6.2K views
      Sissy cuckold Delilah humping pillows while her wife is dating
      Sissy cuckold Delilah humping pillows while her wife is dating
      Delilah Quint
      11.3K views
      Must-see moment from "German anal tranny date outdoor on holiday in Mallorca"
      Must-see moment from "German anal tranny date outdoor on holiday in Mallorca"
      EroCom
      2.3K views
      Cum after Date
      Cum after Date
      Katha Vika
      2.6K 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
      1.5K views
      Let's play before our date!
      Let's play before our date!
      Cassandra Lovit
      668 views
    • When you feel horny, try dating a crossdresser like me.
      11:25
      When you feel horny, try dating a crossdresser like me.
      WanidaCrossdresser
      41.2K views
    • Mtf Big Tit Asian Redhead Impregnablelexa and Wolfdaddy901 Clean Their Pipes for Their Big Date with New Hottie
      58:36
      Mtf Big Tit Asian Redhead Impregnablelexa and Wolfdaddy901 Clean Their Pipes for Their Big Date with New Hottie
      DaddyandLexa
      25.6K 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
      45.8K views
    • Dating a Guy, I'm the Only One in the Camera.
      02:50
      Dating a Guy, I'm the Only One in the Camera.
      Taiwancdgirl
      18.4K views
    • A slutty college girl wearing date outfits and black pantyhose moans loudly while trying deep anal fingering for the first time
      11:35
      A slutty college girl wearing date outfits and black pantyhose moans loudly while trying deep anal fingering for the first time
      Harinni
      14.5K views
    • German amateur teen shemale get anal fuck in bathroom homemade
      12:54
      German amateur teen shemale get anal fuck in bathroom homemade
      Transen-von-Nebenan
      705.3K views
    • Femboy Cherry's date
      01:36
      Femboy Cherry's date
      188K views
    • Romantic Date with a Client
      13:52
      Romantic Date with a Client
      Stripchat official
      63K views
    • Tgirl Riley & TgrilTrainerNL date #8 part I
      25:23
      Tgirl Riley & TgrilTrainerNL date #8 part I
      Tgirl Riley
      28.4K views
    • POV me begging a stranger for a date
      06:30
      POV me begging a stranger for a date
      JessicaLynn15
      8.3K views
    • Dating Makes Me Horny
      10:48
      Dating Makes Me Horny
      Mistress Jodie May
      3.1K views
    • A fuck date with SIssy Lora
      06:38
      A fuck date with SIssy Lora
      129.7K views
    • Beril, who combines with her lover for a date, has a hard time deciding what to wear.
      05:32
      Beril, who combines with her lover for a date, has a hard time deciding what to wear.
      Usaberilx
      6.1K views
    • Let's play before our date!
      05:00
      Let's play before our date!
      Cassandra Lovit
      77.9K views
    • Tgirl Riley & Tgirl Trainer date #13 Part II
      12:51
      Tgirl Riley & Tgirl Trainer date #13 Part II
      Tgirl Riley
      3.1K views
    • Nylon Sissy Slut Michelle Wake up at the Hotel After a Date on Vacation in Turkey
      01:04:55
      Nylon Sissy Slut Michelle Wake up at the Hotel After a Date on Vacation in Turkey
      FapHouse
      18K views
    • Date night with a granny tranny wife!
      11:39
      Date night with a granny tranny wife!
      Victoria Lecherri
      8.3K views
    • Tranny Girlfriend Gets Ready Before Big Date
      04:03
      Tranny Girlfriend Gets Ready Before Big Date
      FapHouse
      21.4K views
    • Our First Date
      05:00
      Our First Date
      Cassandra Lovit
      1K views
    • My Grindr BBC Date fucks my sissy crossdresser ass good!
      01:10
      My Grindr BBC Date fucks my sissy crossdresser ass good!
      158.4K views
    • Date Night with Latina T-MILF shemale Janice Renee
      10:58
      Date Night with Latina T-MILF shemale Janice Renee
      Janice Renee
      36.2K views
    • Tgirl Riley and TgirlTrainerNL date #8 partII
      25:52
      Tgirl Riley and TgirlTrainerNL date #8 partII
      Tgirl Riley
      48.2K views
    • Date in Hotel Room with a Friend
      10:40
      Date in Hotel Room with a Friend
      Milady Silvia Helena
      11.5K views
    • My Handsome Futa Girlfriend Asking Me For A Date & Got Her Mobile Number to Keep in Touch Forever
      05:58
      My Handsome Futa Girlfriend Asking Me For A Date & Got Her Mobile Number to Keep in Touch Forever
      FapHouse
      11.1K views
    • Getting ready for a first date. He has a few special requests that I am fulfilling!
      10:21
      Getting ready for a first date. He has a few special requests that I am fulfilling!
      Victoria Lecherri
      34.7K views
    • Hazelnut Latte: Got Caught Cheating and Fucking Trans in the Mouth on the First Date - Episode 2
      10:13
      Hazelnut Latte: Got Caught Cheating and Fucking Trans in the Mouth on the First Date - Episode 2
      Dirty GamesxXx
      2.3K 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 Sissy Date

    • Crossdresser First Time With a Man
    • Sissy Femboy Fucked
    • Please Don T Fuck Me
    • Secret Sissyboy
    • Grindr Date
    • Lossing Virginity
    • Shemale Seduces Straight Guy
    • Dirty Crossdressers Slut
    • Homemade Trans Sex
    • Slutty Nasty Crossdressing Gurl
    • Real Caught on Camera
    • Sissyslut
    • Feminine Boys
    • Ruined
    • Sloppy Seconds
    • Futa Girls Transformed Into Shemales
    • When She Bigger Than You
    • Daddy's Girl
    • Stepsister XXX
    • Amateur Trap
    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