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

    First Time Crossdressing Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Perversion Crossdressing
    Frist Time
    First BJ
    Beautiful First Time
    Crossdressing Party
    First Time Fisting
    Bearded Crossdressing
    Sissy Time
    His First
    Crossdressing Nun
    Shemale First
    First Time Breeding
    Crossdressing Orgy
    Sissy Crossdressing
    Sauna Crossdressing
    First Threesome
    Amateur First
    Crossdressing Heaven
    Crossdressing Threesome
    First Black
    Best Videos
    By clicking the content you will also see an ad. AD
    Trans Taking an Anal Virginity
    08:12
    Trans Taking an Anal Virginity
    Mistress Jodie May
    389.1K views
    Trans Slut With Big Ass Gets Fucked By Trans Beauty - prettyboi2000x
    20:30
    Trans Slut With Big Ass Gets Fucked By Trans Beauty - prettyboi2000x
    Prettyboi2000x
    89.8K views
    BF demolishes my young femboy bussy (2025 Remaster)
    12:36
    BF demolishes my young femboy bussy (2025 Remaster)
    Prettyboi2000x
    68.8K views
    Wife let me wear her clothes and sissygasm
    06:24
    Wife let me wear her clothes and sissygasm
    OneWhoHasFun
    28.3K views
    Hot trans loves big cocks. Full movie
    40:56
    Hot trans loves big cocks. Full movie
    PalmasRecordsMen
    264.7K views
    Sexy Crossdresser sucks and talks to Daddy
    06:41
    Sexy Crossdresser sucks and talks to Daddy
    MadisonCD2025
    10.9K views
    Compilation of anal fucking to the beautiful Karlita
    10:24
    Compilation of anal fucking to the beautiful Karlita
    PalmasRecordsMen
    27.2K views
    Trans Femboy Gets Ass Destroyed By College Teacher (2025 Remaster)
    11:27
    Trans Femboy Gets Ass Destroyed By College Teacher (2025 Remaster)
    Prettyboi2000x
    21.5K views
    Gay Sissy Crossdresser White Big Ass Big Butt Booty Girly Boy MTF LGBT Lady Boy Fem Boy Bottom Cute
    06:33
    Gay Sissy Crossdresser White Big Ass Big Butt Booty Girly Boy MTF LGBT Lady Boy Fem Boy Bottom Cute
    Crossdresserkitty
    146.2K views
    TRANS FEMALE GETS ANAL FUCKED WITH HARNESS BY TWO VERY HORNY LESBIANS
    11:35
    TRANS FEMALE GETS ANAL FUCKED WITH HARNESS BY TWO VERY HORNY LESBIANS
    TinaQueen_noa
    22.8K views
    Beautiful Femboy Astolfo gets pounded deeply and ass full of cum (2025 Remaster)
    16:20
    Beautiful Femboy Astolfo gets pounded deeply and ass full of cum (2025 Remaster)
    Prettyboi2000x
    10.9K views
    Sissy femboy solo dildo cum
    06:54
    Sissy femboy solo dildo cum
    Passivosucio
    6.3K views
    The sissy slut gets cum in her throat during deepthroating and humiliation
    02:05
    The sissy slut gets cum in her throat during deepthroating and humiliation
    alinanightsky
    191.1K views
    Crossdressing Madison CD compilation in lingerie and stockings and heels showing off
    05:48
    Crossdressing Madison CD compilation in lingerie and stockings and heels showing off
    MadisonCD2025
    8.3K views
    I need so much
    05:00
    I need so much
    Karma Rainbow Smith D
    215.7K views
    Solo Arab Sissy Masturbating, 9ahba Skhona
    11:23
    Solo Arab Sissy Masturbating, 9ahba Skhona
    SmolBoimimi
    39.4K views
    The First Sissy _ Michael Got Rough & Hard Sloppy Blowjob from Me Before Taking Shower
    06:21
    The First Sissy _ Michael Got Rough & Hard Sloppy Blowjob from Me Before Taking Shower
    Asura
    8.8K views
    Joanie - My Very First Video - Part 2
    32:48
    Joanie - My Very First Video - Part 2
    Joanie Blair
    52.1K views
    My roommate fucks cute little hole ts
    06:25
    My roommate fucks cute little hole ts
    AfryycaWendolynne
    32.4K views
    Moaning Femboy Slut Venti gets ass fucked and creampied (2025 Remaster)
    15:45
    Moaning Femboy Slut Venti gets ass fucked and creampied (2025 Remaster)
    Prettyboi2000x
    11.7K views
    Amateur Trans teen pornstar Jesse Montez gives sloppy blowjob to obnoxious straight white boy
    01:36
    Amateur Trans teen pornstar Jesse Montez gives sloppy blowjob to obnoxious straight white boy
    JsseMontz
    52.7K views
    Amazing soft tiny clit sissygasm
    05:59
    Amazing soft tiny clit sissygasm
    Cindy Belfast
    5.3K views
    Sydney Offers Her Ass to Max & Leaking Cum in School Library
    07:56
    Sydney Offers Her Ass to Max & Leaking Cum in School Library
    Asura
    6.8K views
    Sexy sissy in pink lingerie loves playing with her toys. cross dressing femboy fucks ass riding dildo
    06:21
    Sexy sissy in pink lingerie loves playing with her toys. cross dressing femboy fucks ass riding dildo
    Marcus Domes
    6.2K views
    Just me, in white panties, letting myself be done
    06:18
    Just me, in white panties, letting myself be done
    MTFXXXVIDS
    3.3K views
    Hot shower, do you get the hint?
    12:20
    Hot shower, do you get the hint?
    P PoloBigWin
    4K 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
    5.1K views
    Trans School Girl Gets Her Ass Fucked By Horny Roommate
    16:33
    Trans School Girl Gets Her Ass Fucked By Horny Roommate
    Prettyboi2000x
    5.7K views
    Trans girl likes anal toy
    03:31
    Trans girl likes anal toy
    Rana Katana
    107.7K views
    19 Years Old Cute Sissy Jude's Serves Her First Day in Gloryhole Handjob
    05:32
    19 Years Old Cute Sissy Jude's Serves Her First Day in Gloryhole Handjob
    Asura
    7.9K views
    Let it all OUT
    18:53
    Let it all OUT
    Karma Rainbow Smith D
    70.8K views
    Trans Cosplayer gets tight ass destroyed and moans in pleasure (2025 Remaster)
    14:23
    Trans Cosplayer gets tight ass destroyed and moans in pleasure (2025 Remaster)
    Prettyboi2000x
    4.8K views
    An Arab effeminate throws from behind
    05:21
    An Arab effeminate throws from behind
    SmolBoimimi
    14.6K views
    Sissy Crossdresser talks to Daddy and plays with herself
    07:34
    Sissy Crossdresser talks to Daddy and plays with herself
    MadisonCD2025
    1.8K views
    PetraTVsletje making her first porn movie with a very big dick
    08:05
    PetraTVsletje making her first porn movie with a very big dick
    TgirlTrainerNL
    54.3K views
    First to Cum Challenge - Veronica Sanders
    05:27
    First to Cum Challenge - Veronica Sanders
    Veronica Sanders
    34.4K views
    Fuck my ass with a big Cucumber until Cum
    06:36
    Fuck my ass with a big Cucumber until Cum
    SmolBoimimi
    5K views
    My Body Is A Canvas & Bon To Look Like A Girl
    12:44
    My Body Is A Canvas & Bon To Look Like A Girl
    Asura
    4.5K views
    Karla loves to feel a delicious cock inside her tight ass
    09:59
    Karla loves to feel a delicious cock inside her tight ass
    PalmasRecordsMen
    85.5K views
    Trans Verbal Demands   -Elegant Look With Glove And Sweet Dress
    13:00
    Trans Verbal Demands -Elegant Look With Glove And Sweet Dress
    Syn Thetic
    68.5K views
    A Tempting Offer - Ellie & Max Meets in Hospital
    05:48
    A Tempting Offer - Ellie & Max Meets in Hospital
    Asura
    11.5K views
    I Really Cheated on My Husband With His Futanari Sister Jade Yesterday
    09:32
    I Really Cheated on My Husband With His Futanari Sister Jade Yesterday
    Asura
    10.4K views
    Trans Couple Love Sex 2025 Latest Cartoon Sex Animation
    05:05
    Trans Couple Love Sex 2025 Latest Cartoon Sex Animation
    d dollysex
    5.7K views
    Miss me?
    03:24
    Miss me?
    Karma Rainbow Smith D
    75.4K views
    Sydney's Thrilling Tits Fuck Offer in The Library
    06:59
    Sydney's Thrilling Tits Fuck Offer in The Library
    Asura
    3.4K views
    IFYBO - Principal Fucks Hard Virgin Ass Student Chris and Creampied A Huge in The Hole
    10:15
    IFYBO - Principal Fucks Hard Virgin Ass Student Chris and Creampied A Huge in The Hole
    Asura
    6.7K views
    This is how I keep my ass after fucking hard with my stepdad
    06:02
    This is how I keep my ass after fucking hard with my stepdad
    Dessietsa
    33.6K views
    • Back
    • 1
    • ...
    • 4
    • 5
    • 6
    • 7
    • 8
    • ...
    • 80
    • Next

    Searches Related to First Time Crossdressing

    • Try on
    • Family Nudism Stories
    • 2 Sissies 1 Chastity Cage
    • Role Play
    • Slutwife Secrets
    • Sisy Boy
    • Bisexual Creampie Orgy
    • Gay Sissyboy
    • Trapped
    • Anonymous Motel
    • Fuck My Ass Please Dirty Talk
    • Shemale Undressing
    • Pantyhose Couple
    • Ladyboy Striptease
    • Boys Will Be Girls
    • Real CD
    • Hotel Whore
    • Feminization
    • Lesbian Panty
    • Transgirl

    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