PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    WINTER MAGIC SALE ❄️☃️ Snowy discounts, hot deals!

    First Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy Anal
    Sissy Caption
    Sissy Bondage
    Sissy Trainer
    Transvestites Sissies
    Asian Sissy
    Homemade Sissy
    Sissy JOI
    Sissy BDSM
    Sissy Daddy
    Sissy Pegging
    Sissy Femboy
    Black Sissy
    Russian Sissy
    Sissy Maker
    Sissy Dildo
    Mature Sissy
    Sissy Brainwash
    Mommy Sissy
    Sissy Deepthroat
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Sissy 6
      19:29
      Sissy 6
      1.4M views
    • Hot trans loves big cocks. Full movie
      40:56
      Hot trans loves big cocks. Full movie
      PalmasRecordsMen
      265.7K views
    • I got on Grindr got fucked and had multiple sissygasms
      04:09
      I got on Grindr got fucked and had multiple sissygasms
      OneWhoHasFun
      158.6K views
    • Fucking with Dragon Dildo First Time
      04:43
      Fucking with Dragon Dildo First Time
      PrincessKitti3
      99.6K views
    • travesti amateur
      04:25
      travesti amateur
      1.7M views
    • I give a good fuck to my friend pro her pussy pro first sight
      08:21
      I give a good fuck to my friend pro her pussy pro first sight
      Mariaa
      498.9K views
    • Roomie likes to fuck my ass til he fill it with cum
      05:59
      Roomie likes to fuck my ass til he fill it with cum
      missangell_
      751.9K views
    • Daddy's FIRST Blowjob from A Sissy Crossdresser on Grindr
      01:08
      Daddy's FIRST Blowjob from A Sissy Crossdresser on Grindr
      383.8K views
    • Male to female gender transformation smoking whore
      16:00
      Male to female gender transformation smoking whore
      695K views
    • Hardcore Throat and Ass Fucking: TS Gray Perrier Takes a Rough Pounding from Big Danny
      07:25
      Hardcore Throat and Ass Fucking: TS Gray Perrier Takes a Rough Pounding from Big Danny
      Gray Perrier
      19.7K views
    • Hot tranny loves married cock
      05:08
      Hot tranny loves married cock
      LittleVixenSlut
      86.8K views
    • GROOBYGIRLS: Valencia's First Hardcore!
      03:00
      GROOBYGIRLS: Valencia's First Hardcore!
      Grooby Girls
      677.1K views
    • I can't believe i'm posting this! BBC Fucks Sissy
      00:50
      I can't believe i'm posting this! BBC Fucks Sissy
      Sissy Joyce
      443.3K views
    • German amateur 18yo tranny next door do homemade anal porn
      07:45
      German amateur 18yo tranny next door do homemade anal porn
      Transen-von-Nebenan
      716.7K views
    • Sissy's first fuck on video
      06:39
      Sissy's first fuck on video
      150.9K views
    • Mommy Holy - JOI CEI - First Time Cum Eating
      11:15
      Mommy Holy - JOI CEI - First Time Cum Eating
      Holy
      142.1K views
    • Me getting fucked in heels
      13:34
      Me getting fucked in heels
      Johanne95
      1.4M views
    • FIRST BBC FUCKS CUM OUT OF HER & CUMS ON KylieKissesXXX FACE
      12:32
      FIRST BBC FUCKS CUM OUT OF HER & CUMS ON KylieKissesXXX FACE
      KylieKissesXXX
      118.4K views
    • 19 year old trans fucked hard by stranger in hotel room
      05:38
      19 year old trans fucked hard by stranger in hotel room
      Crystal Phoenix
      128.5K views
    • TGirl Charlotte's first orgy.
      22:54
      TGirl Charlotte's first orgy.
      Lisa Essex
      456.1K views
    • Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
      18:27
      Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
      Vane03_siss
      222.4K views
    • Relevant Short videos

      My First Sissy Vlog
      My First Sissy Vlog
      AveloraVioleta
      905 views
      Thrilling moment from "The first sissy superhero is there for you whenever you get horny"
      Thrilling moment from "The first sissy superhero is there for you whenever you get horny"
      cd_aysemmm
      363 views
      Stunning moment from "First sissy clip try! My subscriber sent me a huge dildo and fufu clip so I had trouble putting on as"
      Stunning moment from "First sissy clip try! My subscriber sent me a huge dildo and fufu clip so I had trouble putting on as"
      Harinni
      615 views
      The First Sissy _ Michael Got Rough & Hard Sloppy Blowjob from Me Before Taking Shower | Clip 1
      The First Sissy _ Michael Got Rough & Hard Sloppy Blowjob from Me Before Taking Shower | Clip 1
      Asura
      155 views
      First time going out like a sissy slut !
      First time going out like a sissy slut !
      MommyThongs
      65.4K views
      6 orgasms in 15 secs,Compilation
      6 orgasms in 15 secs,Compilation
      boobyb0y
      25.3K views
    • Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson
      05:29
      Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson
      654.6K views
    • POV Anal Sex Cute Femboy Trans - Nightsisterlil1 Girlcock Boobs Feet
      05:33
      POV Anal Sex Cute Femboy Trans - Nightsisterlil1 Girlcock Boobs Feet
      NightSisterLil1
      403.1K views
    • What's Russian for Suck My Cock? First Time Girl Fucked by TS Teacher
      06:12
      What's Russian for Suck My Cock? First Time Girl Fucked by TS Teacher
      TS Pussy Hunters by Kink
      8.5K views
    • Lover fucked Vika Tverskaya rough
      06:04
      Lover fucked Vika Tverskaya rough
      vika_sissy
      77.6K views
    • Veronica Sanders' Casting: Taking her first Big Black Cock
      05:06
      Veronica Sanders' Casting: Taking her first Big Black Cock
      Veronica Sanders
      10.8K views
    • First Date and First Scene
      06:12
      First Date and First Scene
      Pure Ts
      125K views
    • Gfe First Machine Fuck
      18:45
      Gfe First Machine Fuck
      PrincessKitti3
      116.6K views
    • BF demolishes my young femboy bussy (2025 Remaster)
      12:36
      BF demolishes my young femboy bussy (2025 Remaster)
      Prettyboi2000x
      69.9K views
    • Bulge Worship Tease - Just Enough to Drive You Crazy
      08:31
      Bulge Worship Tease - Just Enough to Drive You Crazy
      Medi Voi
      11.5K views
    • Daddy loves to wreck my asshole in chastity
      06:24
      Daddy loves to wreck my asshole in chastity
      missangell_
      478.3K views
    • Sexy Crossdresser sucks and talks to Daddy
      06:41
      Sexy Crossdresser sucks and talks to Daddy
      MadisonCD2025
      10.9K views
    • Fuck my throat as hard as possible as deep as you can, daddy
      05:51
      Fuck my throat as hard as possible as deep as you can, daddy
      missangell_
      150.3K views
    • Cute Fat Ass Trans First Time Fuck-machine and Self Footjob
      01:30
      Cute Fat Ass Trans First Time Fuck-machine and Self Footjob
      Melodyfluffington
      90.8K views
    • Many crossdressers fucked scrnrs
      01:09:02
      Many crossdressers fucked scrnrs
      1.4M views
    • Alysons First Shoot with Thad Maxxx
      06:56
      Alysons First Shoot with Thad Maxxx
      Thad Maxxx
      81.9K views
    • Sissy Slut Motel
      58:39
      Sissy Slut Motel
      727K views
    • My first man
      01:07
      My first man
      Fruk
      129.8K views
    • Guy gets fooled into sex with a shemale
      06:15
      Guy gets fooled into sex with a shemale
      Love4TS
      2.6M views
    • Sissy Training After First Time Feminization
      12:20
      Sissy Training After First Time Feminization
      Bailey Wilde
      300.8K views
    • Tgirl Riley offers her little ass in the hallway
      20:16
      Tgirl Riley offers her little ass in the hallway
      Tgirl Riley
      97.3K views
    • Paula Rainbow takes her first spin on a fucking machine
      07:06
      Paula Rainbow takes her first spin on a fucking machine
      Paula Rainbow
      9.7K views
    • Tgirl Squirting Literally Flashing Ass and Doing a Lot of Squirting
      08:12
      Tgirl Squirting Literally Flashing Ass and Doing a Lot of Squirting
      barbanegrazponto1onepov
      620.8K views
    • Onlyfans fan fucks me for the first time
      07:08
      Onlyfans fan fucks me for the first time
      SLU77Y
      21.5K views
    • Completely Submitted and Feminized
      08:12
      Completely Submitted and Feminized
      Pure Ts
      49.6K views
    • Man fucks crossdresser in studio
      16:23
      Man fucks crossdresser in studio
      WanidaCrossdresser
      56.6K views
    • Sissy secretary fucked hard bent over the table
      06:50
      Sissy secretary fucked hard bent over the table
      Ashley Roze
      934K views
    Previous page
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 42
    9. ...
    10. 80
    80

    Searches Related to First Sissy

    • Crossboy With Mommy Clothes
    • Guy Moans
    • Loud Moaning
    • Nasty Amateurs
    • Tight Virgin Pussy
    • Pinned Against Wall
    • Sissykanisa
    • Crossdressers Hardcore
    • The Sissy's Future
    • Crossdresser Riding
    • Intense Anal Orgasm
    • Breeding Slave
    • Sissysubkrystal
    • Hands Free Sissygasm
    • Innocent Dickgirl
    • Alpha Male
    • Balls Deep Penetration
    • So Sweet
    • Losing Virginity
    • I Love You
    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