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 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
    Best Videos
    By clicking the content you will also see an ad. AD
    BBC Two Huge Cocks for Tight Little European Trans Ass
    08:12
    BBC Two Huge Cocks for Tight Little European Trans Ass
    Trans and Co
    251.8K views
    Story of when daddy pimped me out. First week. Anal toy.
    08:50
    Story of when daddy pimped me out. First week. Anal toy.
    Sunaxfemiknulla
    18.3K views
    Tgirl Riley offers her little ass in the hallway
    20:16
    Tgirl Riley offers her little ass in the hallway
    Tgirl Riley
    94.1K 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
    129.9K views
    I Fuck a Beautiful 19-year-old Trans Girl with a Big Dick
    08:12
    I Fuck a Beautiful 19-year-old Trans Girl with a Big Dick
    barbanegrazponto1onepov
    2.1M views
    Sissy's first fuck on video
    06:39
    Sissy's first fuck on video
    149.5K views
    A Prostitute Offering Herself on the Street
    02:29
    A Prostitute Offering Herself on the Street
    Wesley Fudedor
    332.8K views
    I’m still learning how to suck a dick, he’s my first and he’s huge.
    05:43
    I’m still learning how to suck a dick, he’s my first and he’s huge.
    Calm
    80.8K views
    I had my first sex, he came inside me :(
    05:08
    I had my first sex, he came inside me :(
    cd_aysemmm
    109.3K views
    gorgeous crossdresser takes her first real dick
    08:12
    gorgeous crossdresser takes her first real dick
    Pure Ts
    121.2K views
    Sissy Joyce - A real life sissy slave
    01:16
    Sissy Joyce - A real life sissy slave
    Sissy Joyce
    687.7K views
    My first self facial
    01:25
    My first self facial
    AsianSissy_Joey
    308.5K views
    Daddy loves to wreck my asshole in chastity
    06:24
    Daddy loves to wreck my asshole in chastity
    missangell_
    475.7K views
    Straight First Time Explode in Sissy Mouth
    08:34
    Straight First Time Explode in Sissy Mouth
    740.2K views
    Lily DeMure Blowjob & Doggy
    11:54
    Lily DeMure Blowjob & Doggy
    1.6M views
    First Time Feminized Means First Time Fucked in the Ass
    12:21
    First Time Feminized Means First Time Fucked in the Ass
    Bailey Wilde
    87K views
    CD TRAP SISSY EDUCATION TRAINING 101
    01:27:33
    CD TRAP SISSY EDUCATION TRAINING 101
    927.7K views
    Let Me Be Your First Femboy
    04:39
    Let Me Be Your First Femboy
    mothplayboy
    98.5K views
    You Are Just a Hole - Variety Itsol
    10:46
    You Are Just a Hole - Variety Itsol
    Rodrigo Amor
    1.8M views
    Hot trans loves big cocks. Full movie
    40:56
    Hot trans loves big cocks. Full movie
    PalmasRecordsMen
    264.7K views
    shemale dresses sissy to fuck
    16:14
    shemale dresses sissy to fuck
    2.1M 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
    493.9K views
    Fucking like a little bitch
    15:52
    Fucking like a little bitch
    Piou_Sissy
    121.8K views
    Fucking with Dragon Dildo First Time
    04:43
    Fucking with Dragon Dildo First Time
    PrincessKitti3
    99.6K views
    Lola Sissification 2 Part 1 - G018
    07:29
    Lola Sissification 2 Part 1 - G018
    Lola Femme
    707K views
    Femboy Gets Bred by Savino Black
    06:56
    Femboy Gets Bred by Savino Black
    mothplayboy
    9.8K views
    Mature Sissy Gets Her Slutty Ass Fucked Hard
    18:54
    Mature Sissy Gets Her Slutty Ass Fucked Hard
    Trans and Co
    54.1K views
    Daddy's FIRST Blowjob from A Sissy Crossdresser on Grindr
    01:08
    Daddy's FIRST Blowjob from A Sissy Crossdresser on Grindr
    382.8K views
    2 femboys with puffy nipples make love
    04:27
    2 femboys with puffy nipples make love
    4M 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
    715.7K views
    How to train your sissy ass
    17:41
    How to train your sissy ass
    655.9K views
    GROOBYGIRLS: Valencia's First Hardcore!
    03:00
    GROOBYGIRLS: Valencia's First Hardcore!
    Grooby Girls
    675.3K views
    Sissy Dressup Party with Sasha De sade Goes wrong
    01:10
    Sissy Dressup Party with Sasha De sade Goes wrong
    Sissy Joyce
    109.8K 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
    117.2K 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_
    741.3K views
    Mommy Holy - JOI CEI - First Time Cum Eating
    11:15
    Mommy Holy - JOI CEI - First Time Cum Eating
    Holy
    141.1K views
    Lover fucked Vika Tverskaya rough
    06:04
    Lover fucked Vika Tverskaya rough
    vika_sissy
    73.2K views
    TGirl Charlotte's first orgy.
    22:54
    TGirl Charlotte's first orgy.
    Lisa Essex
    454.7K views
    Sissy #2: Becoming A Cock Slut
    15:35
    Sissy #2: Becoming A Cock Slut
    864.4K 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
    7.4K views
    Two Sexy Sissy Do Deep Throat BlowJob
    08:25
    Two Sexy Sissy Do Deep Throat BlowJob
    IskraElectrical49
    126.4K 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
    Sissy Dreams 3
    26:07
    Sissy Dreams 3
    1.2M views
    Gfe First Machine Fuck
    18:45
    Gfe First Machine Fuck
    PrincessKitti3
    115.6K views
    Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
    01:17
    Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
    Allmylinks
    100.6K 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
    12K views
    Behind the Scenes of a Porn Video Featuring a Beautiful European Trans Woman.
    01:13:48
    Behind the Scenes of a Porn Video Featuring a Beautiful European Trans Woman.
    Trans and Co
    156.7K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy First

    • Men Dressed as Women
    • Transgender Twink
    • Successful Transition Mtf
    • Femboys and Sissys
    • Crossdressers Hardcore
    • Innocent Teen
    • Becoming Femme
    • Feminized Husband
    • Short Skirt No Panties
    • Caught in My Wife's Clothes
    • Femboy Getting Fucked
    • Amateur Crossdress
    • Begging for Creampie
    • Gay Sissy
    • Strict Lady
    • Bi Curious Husbands First Time
    • Giving Him an Experience
    • Fem Boys
    • Become Shemale
    • Feminine Guys

    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