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

    Cnc Roleplay First Date Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    You switched to shemale orientation. Do you want to keep searching in the gay section?
    First
    Date
    Roleplay
    First Date
    First Time
    First BBC
    First Anal
    First Sissygasm
    First Trans
    First Blowjob
    Tinder Date
    Ladyboy Date
    Trans Date
    First Creampie
    First Shemale
    Blind Date
    Shemale Roleplay
    Grindr Date
    Straight First
    Sissy Date
    Best Videos
    By clicking the content you will also see an ad. AD
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    POV Taking Cute Sissy's Virginity on the First Date - full vid on LayneLovee Manyvids
    01:20
    POV Taking Cute Sissy's Virginity on the First Date - full vid on LayneLovee Manyvids
    Layne Love
    45.8K views
    Girl forgot to tell her Tinder date that she’s Trans
    07:22
    Girl forgot to tell her Tinder date that she’s Trans
    JsseMontz
    634.4K views
    Victoria Lecherri's first date fantasy (with you?)
    14:09
    Victoria Lecherri's first date fantasy (with you?)
    Victoria Lecherri
    8.7K views
    Guy gets fooled into sex with a shemale
    06:15
    Guy gets fooled into sex with a shemale
    Love4TS
    2.6M 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
    Taking a straight guy home to turn him into my faggot - Elizabeth Stewart
    08:16
    Taking a straight guy home to turn him into my faggot - Elizabeth Stewart
    Elizabeth Stewart
    399.5K views
    Fantasy Dating: Futa Ladyboy With Big Cock Fucks Is Having Sex With Sexy MILF For The First Time Part 6
    08:12
    Fantasy Dating: Futa Ladyboy With Big Cock Fucks Is Having Sex With Sexy MILF For The First Time Part 6
    Dirty GamesxXx
    996 views
    Lovely young girl is a shemale with big cock
    08:11
    Lovely young girl is a shemale with big cock
    10.5M views
    First Date and First Scene
    06:12
    First Date and First Scene
    Pure Ts
    121.8K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.1M views
    First date with a pretty French trans girl, she sucks me and swallows in the kitchen.
    10:46
    First date with a pretty French trans girl, she sucks me and swallows in the kitchen.
    Kern Ostrova
    604.1K views
    Sexy Trans Girl Tricks Straight Boy and Fucks His Holes
    08:12
    Sexy Trans Girl Tricks Straight Boy and Fucks His Holes
    Elizabeth Stewart
    295.6K views
    my first date with a transgender girl.
    18:03
    my first date with a transgender girl.
    660.8K views
    Your First Time Getting Fucked by a Trans Girl: First Date GFE POV Femdom
    06:31
    Your First Time Getting Fucked by a Trans Girl: First Date GFE POV Femdom
    Melissa Masters
    576.2K views
    I FUCK ON THE FIRST DATE
    07:37
    I FUCK ON THE FIRST DATE
    Third sex XXX
    2.3M views
    NEW TEENY TRANNY TS-Emily Adaire FIRST ANAL CREAMPIE
    10:44
    NEW TEENY TRANNY TS-Emily Adaire FIRST ANAL CREAMPIE
    Andy Star
    204.4K views
    Hina's First Date - Futanari Public Cum, Public Piss, Anal Sex, Backshots, and More!
    04:48
    Hina's First Date - Futanari Public Cum, Public Piss, Anal Sex, Backshots, and More!
    AgentRedGirl
    566.7K views
    Your Very First Time - Trans Femdom GFE with Melissa Masters
    03:40
    Your Very First Time - Trans Femdom GFE with Melissa Masters
    Melissa Masters
    367.4K views
    BOBSTGIRLS - Lovely Amanda Riley’s First Date Turns Wild
    03:12
    BOBSTGIRLS - Lovely Amanda Riley’s First Date Turns Wild
    Bobs TGirls
    201.1K views

    Relevant Short videos

    Fantasy Dating: Futa Ladyboy With Big Cock Fucks Is Having Sex With Sexy MILF For The First Time Part 6
    Fantasy Dating: Futa Ladyboy With Big Cock Fucks Is Having Sex With Sexy MILF For The First Time Part 6
    Dirty GamesxXx
    354 views
    Our first date went well
    Our first date went well
    AcrylicCloud
    6.8K views
    Hina's First Date - Futanari Public Cum, Public Piss, Anal Sex, Backshots, and More!
    Hina's First Date - Futanari Public Cum, Public Piss, Anal Sex, Backshots, and More!
    AgentRedGirl
    8.4K views
    Emotional moment from "Tgirl Riley anally used and pleasured on a first date"
    Emotional moment from "Tgirl Riley anally used and pleasured on a first date"
    Tgirl Riley
    1.5K views
    Iconic moment from "Tgirl Riley anally used and pleasured on a first date"
    Iconic moment from "Tgirl Riley anally used and pleasured on a first date"
    Tgirl Riley
    1.3K views
    First date magic
    First date magic
    Pure Ts
    1.7K views
    Hostel Surprise
    37:09
    Hostel Surprise
    3.1M views
    First date magic
    08:12
    First date magic
    Pure Ts
    276.9K views
    Surprise! She has a cock!
    00:49
    Surprise! She has a cock!
    304K views
    Watch Transgirl Ria Bentley Fuck Her 9" Bull on Their First Date
    07:07
    Watch Transgirl Ria Bentley Fuck Her 9" Bull on Their First Date
    Ria_Bentley
    572.1K views
    POV - Straight Guy SEDUCED by Hung Blonde BWC Trans Girl - Cadence Caliber
    03:02
    POV - Straight Guy SEDUCED by Hung Blonde BWC Trans Girl - Cadence Caliber
    TS Cadence Caliber
    132.4K views
    He Wants My Cock on the First Date?!
    01:03
    He Wants My Cock on the First Date?!
    Emily Adaire
    135K views
    surprise she has dick
    07:34
    surprise she has dick
    255.4K views
    Our First Date
    05:00
    Our First Date
    Cassandra Lovit
    10.6K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M 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
    132.3K views
    Veronica Leal Surprises Stacy Cruz with Her FUTA Dick and Gets Her Tight Ass Destroyed - FULL SCENE
    12:33
    Veronica Leal Surprises Stacy Cruz with Her FUTA Dick and Gets Her Tight Ass Destroyed - FULL SCENE
    Futanari XXX
    21.4M views
    TRANSFIXED - Whitney Wright Helps Hot Redhead Erica Cherry Explore New Pleasures On Their First Date
    13:59
    TRANSFIXED - Whitney Wright Helps Hot Redhead Erica Cherry Explore New Pleasures On Their First Date
    Transfixed
    1.2M views
    Emily Adaire TS surprises her one night stand in a trenchcoat
    13:02
    Emily Adaire TS surprises her one night stand in a trenchcoat
    Emily Adaire
    352.7K views
    First Date and First Scene
    06:12
    First Date and First Scene
    Pure Ts
    12.7K views
    Another straight guy getting tricked by this hot tgirl
    26:17
    Another straight guy getting tricked by this hot tgirl
    1.1M views
    No means yes on first date.
    03:04
    No means yes on first date.
    Ts Eve
    301.3K views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.3M views
    ADULT TIME - Best First Date Ever! Casey Calvert Gobbles Up T-Girl Leilani Li & Takes DEEP Creampie!
    15:26
    ADULT TIME - Best First Date Ever! Casey Calvert Gobbles Up T-Girl Leilani Li & Takes DEEP Creampie!
    AdultTime
    225.8K views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    1.9M views
    Shemale Fucks a Strong Big Man at His Home on the First Date
    37:27
    Shemale Fucks a Strong Big Man at His Home on the First Date
    Transsexuell and gay club
    315.9K views
    SURPRISE CUTE TRANNY GIRL ANAL FUCKED
    14:39
    SURPRISE CUTE TRANNY GIRL ANAL FUCKED
    Andy Star
    662.3K views
    Their First Date Ends Up In The Bed
    06:15
    Their First Date Ends Up In The Bed
    Transfixed
    1.3M views
    Hot T GIRL with college boy.
    29:02
    Hot T GIRL with college boy.
    2.9M views
    TRANSFIXED - Horny Babe Leilani Li CUMS In Casey Calvert's Mouth During Their First Date
    15:42
    TRANSFIXED - Horny Babe Leilani Li CUMS In Casey Calvert's Mouth During Their First Date
    Transfixed
    51.3K views
    Triss Futanari POV Creampie Dirty Talk
    02:42
    Triss Futanari POV Creampie Dirty Talk
    WaifuStuff
    44.9K views
    TGIRLS.PORN: Our First Date
    03:11
    TGIRLS.PORN: Our First Date
    TGirls Porn
    120.5K views
    GenderX - Wife Wants Husband To Fuck Her Trans Friend
    12:54
    GenderX - Wife Wants Husband To Fuck Her Trans Friend
    GenderX
    2.7M views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Cnc Roleplay First Date

    • Bi Curious Husbands First Time
    • Shemale Tricks Straight Guy
    • Please Don T Fuck Me
    • Suck My Sissy Cock Dirty Talking
    • Cute Femboy Cums While Riding Dick
    • Real Amateur Homemade
    • Giving Him an Experience
    • He Said He Was a Virgin
    • Ts Seducing Shy Men
    • Mature Crossdresser Hotel Sex Date
    • Tinder Meeting
    • Taking Virginity
    • Accidentally Cumming
    • Wife Watching Husband
    • Young Trans Gets Dominated
    • Breeding Boyfriend
    • One Night Stand
    • Tricked by Tranny
    • Nasty Amateurs
    • Innocent Teen

    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