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

    Chubby First Date Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Chubby sissy cd fucks ass with dildo
    01:09
    Chubby sissy cd fucks ass with dildo
    27.8K views
    Fat Sissy Goes For A Ride
    08:39
    Fat Sissy Goes For A Ride
    7K views
    trying out a new dildo for the first time in my wet pussy - verbal ftm amateur pussy gets fucked
    09:39
    trying out a new dildo for the first time in my wet pussy - verbal ftm amateur pussy gets fucked
    JonaFTM
    7.3K views
    Chubby White Lady Boy Big Butt Shemale Big Ass Sissy Booty Slut
    06:05
    Chubby White Lady Boy Big Butt Shemale Big Ass Sissy Booty Slut
    Crossdresserkitty
    3.4K views
    Chubby White Lady Boy Big Butt Shemale Big Ass Sissy Booty Slut
    05:26
    Chubby White Lady Boy Big Butt Shemale Big Ass Sissy Booty Slut
    Crossdresserkitty
    3K views
    BBW Shemale Pinky Doggystyles Giant Dildo for First Time
    05:03
    BBW Shemale Pinky Doggystyles Giant Dildo for First Time
    PinkyLikes2Play
    9.9K views
    Chubby sissycd
    05:52
    Chubby sissycd
    Milaya_yulia
    4.9K views
    First video
    01:27
    First video
    Milaya_yulia
    2.2K views
    Crossdresser Vanessa twerking first attempt
    03:10
    Crossdresser Vanessa twerking first attempt
    1.3K 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
    Dating a mature crossdresser
    08:12
    Dating a mature crossdresser
    Pure Ts
    234.8K views
    Dollie Date Nite!
    11:04
    Dollie Date Nite!
    AgentRedGirl
    1.8M views
    Sue Lightning wants to suck cock before her date
    07:26
    Sue Lightning wants to suck cock before her date
    Pure Ts
    806.5K views
    The Perfect Date
    07:26
    The Perfect Date
    Futanari XXX
    344.8K views
    TRANSFIXED - Disastrous Dinner Ended In A Delicious Creampie Between Trans Jade Venus And Her Date
    16:56
    TRANSFIXED - Disastrous Dinner Ended In A Delicious Creampie Between Trans Jade Venus And Her Date
    Transfixed
    68.7K views
    A date with a transgender girl from Tijuana in her beloved dad's car until she was given milk
    11:10
    A date with a transgender girl from Tijuana in her beloved dad's car until she was given milk
    Alli0419
    241K views
    German anal tranny date outdoor on holiday in Mallorca
    17:26
    German anal tranny date outdoor on holiday in Mallorca
    EroCom
    447.6K views
    Passionate Date Night
    06:12
    Passionate Date Night
    Pure Ts
    39K views
    huge cock TS Patra Von Tesse fucks her date
    10:01
    huge cock TS Patra Von Tesse fucks her date
    Pure Ts
    2.1M views
    Date Night with Mature Crossdresser
    08:12
    Date Night with Mature Crossdresser
    Pure Ts
    209.1K views
    TRANSFIXED - Caught Horny Zariah Aura CREAMPIES Roommate Tomie Tang's Hot Date Nicole Kitt! 3-WAY
    16:32
    TRANSFIXED - Caught Horny Zariah Aura CREAMPIES Roommate Tomie Tang's Hot Date Nicole Kitt! 3-WAY
    Transfixed
    168.1K views
    Would you still date me even my cock is bigger than yours?
    07:32
    Would you still date me even my cock is bigger than yours?
    PixieglitchTS
    80.9K views
    Cumming Together After Our Date
    24:21
    Cumming Together After Our Date
    WetZemu
    78.7K views
    Shiri gets loved up and fucked after her date
    08:12
    Shiri gets loved up and fucked after her date
    Pure Ts
    78.2K views
    Trans Ariel Demure Bangs Her Neighbor To Get Over A Date
    12:29
    Trans Ariel Demure Bangs Her Neighbor To Get Over A Date
    Devils tgirls
    1.2M views
    Ria Bentley Gets Impregnated by Her 10" Bull Date
    21:12
    Ria Bentley Gets Impregnated by Her 10" Bull Date
    Ria_Bentley
    206.3K views
    tinder date sex
    19:43
    tinder date sex
    1.2M views
    Jessica Host, Prince Blind Date
    08:12
    Jessica Host, Prince Blind Date
    TS Seduction by Kink
    94.2K views
    Intense Passionate Kissing & Makeout Foreplay on Date Night with this GORGEOUS Black Trans Girl Eros Orisha
    08:13
    Intense Passionate Kissing & Makeout Foreplay on Date Night with this GORGEOUS Black Trans Girl Eros Orisha
    K KirkRyner
    166.1K views
    TRANSFIXED - Gorgeous Kasey Kei’s Speed Dating Turns Into Wild TRANS GANGBANG With HUGE FACIAL
    15:43
    TRANSFIXED - Gorgeous Kasey Kei’s Speed Dating Turns Into Wild TRANS GANGBANG With HUGE FACIAL
    Transfixed
    147K views
    DATE & SWITCH - Sneaky Trans Babe Tricks Hunk & Trans Cutie
    12:04
    DATE & SWITCH - Sneaky Trans Babe Tricks Hunk & Trans Cutie
    GenderX
    90.8K views
    Romantic date of hot CD Tiffany in Paris
    37:35
    Romantic date of hot CD Tiffany in Paris
    1M views
    TRANS ANGELS - Sweet Babe Domino Presley Commands Her Date To Put His Cock In Her Mouth & Ass
    23:09
    TRANS ANGELS - Sweet Babe Domino Presley Commands Her Date To Put His Cock In Her Mouth & Ass
    Trans Angels
    341.4K views
    TRANSFIXED - Trans Ariel Demure Is Caught Having Sex With Siri Dahl In Theater During A Double Date
    12:05
    TRANSFIXED - Trans Ariel Demure Is Caught Having Sex With Siri Dahl In Theater During A Double Date
    Transfixed
    1.6M views
    German shemale surprised date partner
    01:09
    German shemale surprised date partner
    Kim Wagner
    1.1M views
    Why Straight Guys date Trans Girls
    06:41
    Why Straight Guys date Trans Girls
    1.2M views
    The Perfect Date
    17:50
    The Perfect Date
    383.5K views
    The Perfect End to the Perfect Date
    08:12
    The Perfect End to the Perfect Date
    Pure Ts
    32.2K views
    Venus Is Joshua's Dream Date
    08:12
    Venus Is Joshua's Dream Date
    Venus Lux
    62.6K views
    Sissy Doll Fucking in a Pegging Date
    07:00
    Sissy Doll Fucking in a Pegging Date
    Brat Perversions
    16.4K views
    SHEMALE GRINDR DATE LOVE
    01:01
    SHEMALE GRINDR DATE LOVE
    630K views
    Sexy young trans girl moans loudly when we fuck on our second date.
    17:26
    Sexy young trans girl moans loudly when we fuck on our second date.
    542.9K views
    Trans On Trans Raw Anal Date - Ariel Demure, Eva Maxim
    11:30
    Trans On Trans Raw Anal Date - Ariel Demure, Eva Maxim
    Transsexual Angel
    607.1K views
    GenderFlux Grinder Date with Viktor Belmont and Shay Bares
    07:19
    GenderFlux Grinder Date with Viktor Belmont and Shay Bares
    DaringSex
    281.4K views
    Busty big cock tgirl Aspen Brooks fuck milf date Lisey Sweet
    06:10
    Busty big cock tgirl Aspen Brooks fuck milf date Lisey Sweet
    GenderX
    570.7K views
    Humiliating Date Story by a Pathetic Piggy
    14:11
    Humiliating Date Story by a Pathetic Piggy
    JessicaLynn15
    17.3K views
    Blonde Skinny Tranny Fucks with Big Cock Tinder Date Anal
    41:16
    Blonde Skinny Tranny Fucks with Big Cock Tinder Date Anal
    Shemale TS Collection
    19.8K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    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