PornPorn Transgender • US
    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
    • Big Cock
    • Black
    • 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
    WINTER MAGIC SALE ❄️☃️ Snowy discounts, hot deals!
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • Shemale Fucks Girl
    • Sissy
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Cum In Mouth
    • Big Black Cock
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy First Time Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    French Sissy
    Sissy Orgasm
    Sissy Spanking
    Sissy Moaning
    Sissy Orgy
    Sissy School
    Sissy Mistress
    Sissy Swallow
    Little Sissy
    Sissy Bnwo
    Sissy Story
    Sissy Fisting
    Japanese Sissy
    Sissy Trap
    First BBC
    Sissy Punishment
    Adult Time
    Bbw Sissy
    Homemade First Time
    Ebony Sissy
    Best Videos
    By clicking the content you will also see an ad. AD
    He Turned 18 and Came to Get the Gift. I Enjoyed Giving
    08:12
    He Turned 18 and Came to Get the Gift. I Enjoyed Giving
    Agatha Lyra
    515.6K views
    Blonde Sissy Riding Her Dildo In Her Latex Suit For The First Time
    14:03
    Blonde Sissy Riding Her Dildo In Her Latex Suit For The First Time
    LoLiLights
    11.6K views
    Sucking some dudes cock while my boyfriend is at work
    05:18
    Sucking some dudes cock while my boyfriend is at work
    JsseMontz
    566.2K views
    Sissi Young first time dildo  Assgasm
    04:26
    Sissi Young first time dildo Assgasm
    S Sissy Slut Nina
    6.5K views
    The first time I take a dick in my ass
    02:55
    The first time I take a dick in my ass
    352.5K views
    My First Time Fisting My Trans Ass with Hand Dildo
    08:12
    My First Time Fisting My Trans Ass with Hand Dildo
    fermerino
    638 views
    Destroyed the fucking ass of the Russian trance
    03:03
    Destroyed the fucking ass of the Russian trance
    vika_sissy
    33.2K views
    Crossdresser Daisy's first time out in the open .
    03:42
    Crossdresser Daisy's first time out in the open .
    Daisywam
    7.3K views
    I want an old man to fuck me in the ass for the first time
    10:40
    I want an old man to fuck me in the ass for the first time
    Dessietsa
    12.5K views
    Virgin Sissy Housewife Fucked with Dildo for the First Time
    12:44
    Virgin Sissy Housewife Fucked with Dildo for the First Time
    SissyHousewife
    3K views
    Trans Girl plays with an 18 cm Dildo for the first time, Moans from pain but ends up liking it  Succubo16
    29:58
    Trans Girl plays with an 18 cm Dildo for the first time, Moans from pain but ends up liking it Succubo16
    LaRicura16
    10.9K views
    Sissy Tries Butt Plug and Chastity For The First Time - Sissy Housewife
    18:40
    Sissy Tries Butt Plug and Chastity For The First Time - Sissy Housewife
    SissyHousewife
    5.6K views
    My First Time with a Shemale: a Raw and Passionate Audio Journey
    00:32
    My First Time with a Shemale: a Raw and Passionate Audio Journey
    Kathai Neram
    1.1K views
    Sissy Schoolgirl my First time Fucking my Ass with a Sex Machine BBC Dildo
    10:23
    Sissy Schoolgirl my First time Fucking my Ass with a Sex Machine BBC Dildo
    Mariana Taylor
    5.4K views
    Asian Crossdresser Turns Satanic Sissy Bitch First Time 1
    03:30
    Asian Crossdresser Turns Satanic Sissy Bitch First Time 1
    7.5K views
    I Receive New Boots and Walk in Them for the First Time
    01:10
    I Receive New Boots and Walk in Them for the First Time
    MicziCD
    9.6K views
    Sissy tries bigger toy for first time, gets surprised
    08:06
    Sissy tries bigger toy for first time, gets surprised
    Jana the Great
    1.8K views
    sissy boy riding black thunder for the first time sisygasm x
    05:46
    sissy boy riding black thunder for the first time sisygasm x
    174K views
    Ruby Stars cute girl, a little bit naughty but heavenly. Shy blonde teen girl first time on webcam kissing a pink dildo.
    16:34
    Ruby Stars cute girl, a little bit naughty but heavenly. Shy blonde teen girl first time on webcam kissing a pink dildo.
    Ruby Stars
    12.3K views
    Asian Sissy Femboy enjoy Dildo Anal Play for the first time - Part 2
    09:40
    Asian Sissy Femboy enjoy Dildo Anal Play for the first time - Part 2
    KamenKnight
    3K views
    Karou Part 1: Cute sissy crossdresses for the first time
    06:15
    Karou Part 1: Cute sissy crossdresses for the first time
    33.6K views
    First time with my Hismith machine
    36:33
    First time with my Hismith machine
    19.5K views
    My Sissy Fat Ass Trying a Vibrator for the First time
    07:16
    My Sissy Fat Ass Trying a Vibrator for the First time
    fermerino
    2.3K views
    First time  ever taking a 14 inch
    03:10
    First time ever taking a 14 inch
    bott17
    1K views
    Sissy Supergirl First Time With Dildo
    16:04
    Sissy Supergirl First Time With Dildo
    Sissy Shelby Kiss
    4.7K views
    My first Time using my fuck machine
    01:37
    My first Time using my fuck machine
    Alice Wonderland
    3.9K views
    First Time Shaggy Fucks a Trans Woman
    01:25
    First Time Shaggy Fucks a Trans Woman
    Jake Grand
    12.2K views
    CindiCsissy eating my own cum for the first time
    15:08
    CindiCsissy eating my own cum for the first time
    CIndiCsissy
    7.7K views
    asian sissy dripping in chastity first time vibrator
    01:23
    asian sissy dripping in chastity first time vibrator
    Christine
    8.9K views
    Wearing Garter for the first time
    05:23
    Wearing Garter for the first time
    Your Toy
    5.8K views
    Guy Feminized and Strapon Fucked for First Time
    00:49
    Guy Feminized and Strapon Fucked for First Time
    Bailey Wilde
    3.4K views
    Pretty student Shemale girl masturbates for the first time after school
    09:31
    Pretty student Shemale girl masturbates for the first time after school
    Xblue-18
    22.9K views
    First Time Rapper Fucks Hot TS in Chastity
    01:41
    First Time Rapper Fucks Hot TS in Chastity
    Jake Grand
    4.6K views
    Fat enby wets their diaper on camera for the first time
    01:39
    Fat enby wets their diaper on camera for the first time
    Platinum Rain
    1.3K views
    Trying my first time doing anal with my dildo and lot of creampies
    05:37
    Trying my first time doing anal with my dildo and lot of creampies
    Ren Midorikawa
    7.6K views
    My first time i wearing high heels )
    01:56
    My first time i wearing high heels )
    Stripchat official
    6.3K views
    My face for the first time ladyboy princess of Pornhub
    06:16
    My face for the first time ladyboy princess of Pornhub
    Crossdresserkitty
    13K views
    Sissy Janine Machine Fuck First Time
    04:31
    Sissy Janine Machine Fuck First Time
    SubmissiveFetish
    12.7K views
    My first time peeing on camera.
    01:15
    My first time peeing on camera.
    9K views
    fucking my ass with my new dildo for the first time
    11:46
    fucking my ass with my new dildo for the first time
    i iacute
    3.2K views
    My First Time in Tights: Embracing My Crossdressing Journey!
    06:34
    My First Time in Tights: Embracing My Crossdressing Journey!
    Crossdresserkitty
    4.9K views
    Crossdresser first time on webcam
    06:32
    Crossdresser first time on webcam
    2.6K views
    my first time in soubrette sissy
    19:01
    my first time in soubrette sissy
    16.7K views
    My First Time
    29:38
    My First Time
    Ts Lucy Morningstar
    4.8K views
    First time being a sissy slut in public
    05:41
    First time being a sissy slut in public
    Christina Taylor
    10.7K 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
    4.8K views
    First Time Squirt
    05:07
    First Time Squirt
    Aashna
    4.5K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy First Time

    • Gorgeous Femboy
    • Sissykanisa
    • Cum Inside Crossdresser
    • Feminization Bondage
    • Role Reversal
    • Straight Friend
    • Hands Free Sissygasm
    • Daddy Issues
    • Sisy Boy
    • Emo Shemale
    • Secret
    • Schoolgirl Stepbrother
    • Feminize Yourself
    • Transformed Into Slut
    • Traps
    • Crossdresserkitty
    • Trans in Skirt
    • Bratty Sis
    • Convinced Roommate
    • Tranny Stepsister

    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