PornPorn Transgender • US
  • Straight
  • Gay
  • Transgender
  • Videos
  • Short videos
  • photos
  • Users
    Forgot password
    Sign in with Google
    Sign in with X
    Sign up for free
    Videos
    • Best Videos
    • Short Videos
    • Watch History
    • American
    • Amateur
    • Shemale Fucks Guy
    • Shemale Fucks Girl
    • Big Cock
    • All categories
    Live Sex
    Categories
    • Shemale Fucks Guy
    • Black
    • Big Cock
    • Shemale Fucks Shemale
    • Amateur
    • All categories
    Pornstars
    • Pornstars
    • By Countries
    • xHamster Creators
    Creators
    • Top Creators
    • Top Creator Videos
    • Awards 2025
    • All xHamster Creators
    • By Countries
    • Become a Creator
    Channels
    Photos
    • Ladyboy
    • Tranny
    • Big Cock
    • Thai
    • Blowjob
    • All categories
    Faphouse
    Premium Videos
    Dating
    Subscriptions
    • Upload
    LET IT SNOW, LET IT SAVE! ☃️ Faphouse Discounts – Winter Edition
    Subscriptions Liked Watch History
    Newest Videos Best Videos Short Videos Top Creators Awards 2025
    • American
    • 4K Porn
    • HD Videos
    • VR Porn
    • Amateur
    • Anal
    • Anal Masturbation
    • Anal Toy
    • Asian
    • Babysitter
    • Bareback
    • BBW
    • BDSM
    • Behind The Scenes
    • Big Ass
    • Big Black Cock
    • Big Cock
    • Big Tits
    • Black
    • Blowjob
    • Bondage
    • Brazilian
    • British
    • Cartoon
    • Chinese
    • Colombian
    • Compilation
    • Couple
    • Creampie
    • Cuckold
    • Cum In Mouth
    • Cumshot
    • Dildo
    • Domination
    • Double Penetration
    • English
    • Fetish
    • FTM
    • Gangbang
    • German
    • Group Sex
    • Guy Fucks Shemale
    • Handjob
    • Hentai
    • Homemade
    • Indian
    • Interracial
    • Japanese
    • Ladyboy
    • Lingerie
    • Massage
    • Masturbation
    • Mature
    • Mexican
    • MILF
    • Outdoor
    • Petite
    • Pissing
    • POV
    • Public
    • Role Play
    • Rough Sex
    • SFW
    • Shemale Fucks Girl
    • Shemale Fucks Guy
    • Shemale Fucks Shemale
    • Sissy
    • Small Cock
    • Small Tits
    • Solo
    • Stockings
    • Teen
    • Thai
    • Threesome
    • Trans Man
    • Trans Woman
    • Transgender
    • Vintage
    • All categories

    Sissy First Trans Porn Videos

    All Short videos
    Newest
    Best Videos
    Premium Videos
    By Rating
    • By Rating
    • By Views
    • By Comments
    Date
    • All
    • 1 Day
    • 7 Days
    • 30 Days
    • Year 2026
    • Year 2025
    Quality
    • All
    • 720p+
    • 1080p+
    • 2160p+
    FPS
    • All
    • 30 FPS
    • 60 FPS
    Duration
    • All
    • 0~2 min
    • 2~5 min
    • 5~10 min
    • 10~30 min
    • 30+ min
    • Full Video
    Production
    • All
    • Producers
    • xHamster Creators
    Sissy
    Sissy First Time
    Sissy First Anal
    Sissy First Cock
    Sissy First Time Fucked
    Sissy First Time Anal
    Young Sissy
    Sissy Feminization
    Amateur Sissy
    Sissy Crossdresser
    Sissy Fuck
    Submissive Sissy
    Sissy Blowjob
    Sissy Lingerie
    Sissy Chastity
    Russian Sissy
    Sissy Gangbang
    Homemade Sissy
    By clicking the content you will also see an ad. AD
    Training to become a sissy cuckold
    03:26
    Training to become a sissy cuckold
    amatorxxx
    628.3K views
    Sissy's first fuck on video
    06:39
    Sissy's first fuck on video
    150.9K views
    Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson
    05:29
    Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson
    657.1K views
    sissy encaged fucked
    04:50
    sissy encaged fucked
    391K views
    Sissy Crossdresser Fucks Dildo Doggystyle (first time)
    04:25
    Sissy Crossdresser Fucks Dildo Doggystyle (first time)
    163.1K views
    Sissy life. First sex like a girl
    09:06
    Sissy life. First sex like a girl
    Color Space
    15.5K views
    We will dress you up before you suck your first cock
    07:42
    We will dress you up before you suck your first cock
    Sissy Instruction
    33.9K views
    Sissy Oksana tore her asshole with a huge bottle but got sissygasm
    09:07
    Sissy Oksana tore her asshole with a huge bottle but got sissygasm
    Oksana2021
    27K views
    Petra 1e training
    22:54
    Petra 1e training
    PetraTVsletje
    55.1K views
    Take this quiz for bottom sissies - ROLEPLAY JOI
    05:34
    Take this quiz for bottom sissies - ROLEPLAY JOI
    Melissa Wet Tales
    6.3K views
    First Stranger Creampie Sissy
    01:56
    First Stranger Creampie Sissy
    50.8K views
    Sissy get fucked fir the first time
    01:27
    Sissy get fucked fir the first time
    45.9K views
    Redhead Sissy First Using a Sex-machine This Is a Sweet Gift From a Fan
    04:01
    Redhead Sissy First Using a Sex-machine This Is a Sweet Gift From a Fan
    Sonechka25
    2.1K views
    Prison of Sissy: The First Friend
    06:43
    Prison of Sissy: The First Friend
    Asura
    34K views
    sissy tits and nipple play
    01:55
    sissy tits and nipple play
    Sissy_sarah69
    65.3K views
    Sissy Lisa tries her Hismith for the first time
    01:28
    Sissy Lisa tries her Hismith for the first time
    36.9K views
    Sissy Alicia having pleasure with a dildo
    11:07
    Sissy Alicia having pleasure with a dildo
    SissyAlicia
    24.6K views
    Sissy Big Booty First Time Anal Dildo
    04:28
    Sissy Big Booty First Time Anal Dildo
    Evelo
    15.7K views
    Our First Pegging Encounter (Sissy Training)
    01:21
    Our First Pegging Encounter (Sissy Training)
    littlemissbrat
    65.5K views
    My first sissygasm
    01:07
    My first sissygasm
    AliciaRose
    4.3K views

    Best Sissy First Shemale Short Videos

    sissy's first sissygasm in flat chastity cage
    sissy's first sissygasm in flat chastity cage
    juergipron
    355 views
    Memorable moment from "Chastity Sissy Millie rides her new toy"
    Memorable moment from "Chastity Sissy Millie rides her new toy"
    Sissy Millie Lucy
    991 views
    Sissy Fun - First BWC
    Sissy Fun - First BWC
    Halls
    753 views
    Preview: first time wearing a chastity cage was intense
    Preview: first time wearing a chastity cage was intense
    Xxhotjanexx
    3.8K views
    Sissy clit first person view
    Sissy clit first person view
    Cassie Cross
    1.3K views
    trans girl jessiesissyadve being naughty
    trans girl jessiesissyadve being naughty
    jessiesissyadventures
    18.2K views
    young Sissy with g-cup breastform in public
    01:36
    young Sissy with g-cup breastform in public
    7.9K views
    my sexy sissy body for you baby
    03:10
    my sexy sissy body for you baby
    SandyPastime578
    just added
    Sissy very first anal masturbation video
    02:39
    Sissy very first anal masturbation video
    Chocolate sissy
    12.9K views
    Sissy first time anal
    02:01
    Sissy first time anal
    T Thick Shady
    12.7K views
    Sissy First Time Big Dildo
    01:36
    Sissy First Time Big Dildo
    S Sissy Slut Nina
    1.8K views
    sissy chav bimbo sucks her first BBC
    01:26
    sissy chav bimbo sucks her first BBC
    49.5K views
    Sissy Samantha first kornfield 2020
    04:42
    Sissy Samantha first kornfield 2020
    7K views
    Sissy Train, First Suckling Test
    06:14
    Sissy Train, First Suckling Test
    g geraldinelonginlove
    4.2K views
    Sissy sounding pathetic clitty for the first time
    02:58
    Sissy sounding pathetic clitty for the first time
    SissyNikki
    2.4K views
    Sissy in chastity plays with Dildo
    02:40
    Sissy in chastity plays with Dildo
    2.3K views
    Sissy jayci goes out in chastity again
    04:25
    Sissy jayci goes out in chastity again
    Sissy Jayci
    5K views
    sissy rubbermaid suck mistress's cock for the first time
    00:38
    sissy rubbermaid suck mistress's cock for the first time
    79.4K views
    First video - training for BBC
    02:53
    First video - training for BBC
    Davina Leggs
    1.7K views
    Femboy sissy does anal for the first time while watching hentai
    09:04
    Femboy sissy does anal for the first time while watching hentai
    Littlecapric
    4.9K views
    First recorded sissygasm
    03:36
    First recorded sissygasm
    9.8K views
    Crossdresser sissy training her thight ass
    17:32
    Crossdresser sissy training her thight ass
    3.7K views
    My First Time with a 24 Cm Dildo and Cumming Like a Sissy
    14:28
    My First Time with a 24 Cm Dildo and Cumming Like a Sissy
    Thipansex
    2.2K views
    Chastity Sissy Millie rides her new toy
    06:41
    Chastity Sissy Millie rides her new toy
    Sissy Millie Lucy
    2.1K views
    Sissy's Tender Hole Was Given a Dildo for the First Time.
    12:22
    Sissy's Tender Hole Was Given a Dildo for the First Time.
    Annyfist
    2.3K views
    Sissy mtf riding a dildo uk
    05:31
    Sissy mtf riding a dildo uk
    Sissyjarvis87
    1.2K views
    Giant Anal Plug
    01:45
    Giant Anal Plug
    4.3K views
    double time again
    14:25
    double time again
    Jade Sissy
    7.7K views
    Sissy Jessica Jay. First blowjob on camera
    01:01
    Sissy Jessica Jay. First blowjob on camera
    7.6K views
    Young sissy first time dressing
    00:47
    Young sissy first time dressing
    5.2K views
    Sissy Jenna having her first kiss with her new love : )
    00:08
    Sissy Jenna having her first kiss with her new love : )
    3.1K views
    My first sissygasm!
    00:31
    My first sissygasm!
    7.6K views
    My sissy joan first blowjob
    00:17
    My sissy joan first blowjob
    4.6K views
    1. 1
    2. 2
    Next

    Categories Related to Sissy First

    • First Time With Trans Woman
    • Shemale Fucks Guy First Time
    • Beautiful Shemales and Girls
    • First Time Shemale
    • Male to Female Transformation
    • Beautiful Lady Boy
    • First Time Trans
    • Teen Traps and Sissy Femboys
    • First Time Ladyboy
    • Shemale Stepmom

    Searches Related to Sissy First

    • Sissy Public
    • Femboy XXX
    • Sissy Exposed
    • Shemale Caught
    • Real Secret Sex
    • Super Feminine Trans Women
    • The Sissy's Future
    • Maximum Perversum Extreme Pervert
    • First Sissygasm
    • Sissy-Boys
    xHamster
    • Press
    • 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
    Start making money with us
    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    Monetize your content
    Become a creator
    © 2007 - 2026, xHamster.com
    Mobile 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