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
    -60%
    Dating
    Subscriptions
    • Upload
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday Sale
    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
    • Homemade
    • Mature
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    First Time Cuckolding Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Cuckold
    First
    Time
    First Time
    Sissy Cuckold
    Young First Time
    Crossdresser First Time
    First Time Shemale
    Shemale Cuckold
    First Time Virgin
    Homemade First Time
    First Time Anal
    Cuckold Crossdresser
    Cd First Time
    First Date
    First Time Ladyboy
    First BBC
    First Time Sucking
    Cuckold Humiliation
    First Time Trans
    Best Videos
    By clicking the content you will also see an ad. AD
    GenderX - Wife Wants Husband To Fuck Her Trans Friend
    12:54
    GenderX - Wife Wants Husband To Fuck Her Trans Friend
    GenderX
    2.7M views
    MY FIRST TIME FUCK BEAUTIFUL SHEMALE ON UPSTAIRS
    19:58
    MY FIRST TIME FUCK BEAUTIFUL SHEMALE ON UPSTAIRS
    Altmodelbox
    22.9K views
    SISSY CUCKOLD
    04:24
    SISSY CUCKOLD
    178K views
    Hot BlackSharon tries her masturbator for the first time on her live cam
    05:37
    Hot BlackSharon tries her masturbator for the first time on her live cam
    Blacksharon
    15.4K views
    Surprise! She has a cock!
    00:49
    Surprise! She has a cock!
    301.5K views
    It's getting horny. For the first time I took my ass a little harder.2024
    08:50
    It's getting horny. For the first time I took my ass a little harder.2024
    7.4K views
    Unexpected Cock Surprise - Trannybizarre
    05:12
    Unexpected Cock Surprise - Trannybizarre
    Tranny Bizarre
    306.9K views
    My first time fucking trans man
    05:33
    My first time fucking trans man
    Nathalia Fontes
    139.4K views
    SHEMALE fucks HUSBAND & WIFE
    04:44
    SHEMALE fucks HUSBAND & WIFE
    1.1M views
    GORGEOUS BRUNETTE WITH WET PUSSY TASTE SHEMALE COCK FIRST TIME
    23:12
    GORGEOUS BRUNETTE WITH WET PUSSY TASTE SHEMALE COCK FIRST TIME
    Altmodelbox
    10.4K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    First time cuck sissy record for her mistress
    46:52
    First time cuck sissy record for her mistress
    Assexploringmachin
    2.2K views
    Myself and a couple
    03:16
    Myself and a couple
    526.2K views
    Wife let me wear her clothes and sissygasm
    06:24
    Wife let me wear her clothes and sissygasm
    OneWhoHasFun
    26.5K views
    Sissy hubby with wife.
    19:05
    Sissy hubby with wife.
    133K views
    Shemale world gameplay part 13
    07:20
    Shemale world gameplay part 13
    Amaran
    11.3K views
    surprise she has dick
    07:34
    surprise she has dick
    254.3K views
    Instinct Unleashed gameplay parte 1
    35:13
    Instinct Unleashed gameplay parte 1
    jackyxxx
    9.6K 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
    388.7K views
    TOY TIME FIRST THING IN THE MORNING
    01:52
    TOY TIME FIRST THING IN THE MORNING
    TWERKINGBOYS
    2.8K views
    Wife Catches Husband With TS Girl, Makes Him Sucks Her Dick
    12:52
    Wife Catches Husband With TS Girl, Makes Him Sucks Her Dick
    GenderX
    1.3M views
    Double Deep Throat Blowjob Training With Olivia with Huge Plastic Dildo
    06:30
    Double Deep Throat Blowjob Training With Olivia with Huge Plastic Dildo
    Asura
    5.5K views
    Jerk Husband Has Nasty Affair Behind Wife's Back!
    06:16
    Jerk Husband Has Nasty Affair Behind Wife's Back!
    261K views
    Olivia Puts Chastity Cage on My Cock
    05:23
    Olivia Puts Chastity Cage on My Cock
    Asura
    3.7K 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
    623.1K views
    Futanari Stepmom Worries About Stepson Max's Appointment
    05:43
    Futanari Stepmom Worries About Stepson Max's Appointment
    Asura
    7.1K views
    Amateur married couple invites stunning transsexual whore
    08:49
    Amateur married couple invites stunning transsexual whore
    2.8M views
    Trip Of A Life Time
    10:56
    Trip Of A Life Time
    Asura
    2.6K views
    Hostel Surprise
    37:09
    Hostel Surprise
    3.1M views
    Slutt Crossdresser tells bbc cuckold story and plays it out. The bbc fucks his hot white wife
    06:52
    Slutt Crossdresser tells bbc cuckold story and plays it out. The bbc fucks his hot white wife
    MadisonCD2025
    582 views
    cuckold swap his wife for a shemale and his wife got fucked
    10:38
    cuckold swap his wife for a shemale and his wife got fucked
    Borntrans
    3.3M views
    When Sera and Beril are alone at home, they have sex and get caught!
    06:08
    When Sera and Beril are alone at home, they have sex and get caught!
    Usaberilx
    1K views
    Wife Surprises Hesitant Husband With Trans Sex Worker
    12:55
    Wife Surprises Hesitant Husband With Trans Sex Worker
    GenderX
    428.4K views
    What A Convenient Trick by Futanari Kate
    05:14
    What A Convenient Trick by Futanari Kate
    Asura
    2.9K views
    Another straight guy getting tricked by this hot tgirl
    26:17
    Another straight guy getting tricked by this hot tgirl
    1.1M views
    Horse cock in big white virgin asshole, first try, lubed and ready, but still virgin pussy is tight but juicy
    06:02
    Horse cock in big white virgin asshole, first try, lubed and ready, but still virgin pussy is tight but juicy
    20.3K views
    I want to watch my boyfriend railing a shemale
    16:19
    I want to watch my boyfriend railing a shemale
    Shemales Fuck Couples
    1.9M views
    Crossdresser Cdmichelle putting on Lace Panties & Lingerie
    06:02
    Crossdresser Cdmichelle putting on Lace Panties & Lingerie
    CdMichelleX
    1.4K views
    Wife Videos Sissy Cuckol Being Fucked By Crossdressing stran
    02:44
    Wife Videos Sissy Cuckol Being Fucked By Crossdressing stran
    491.6K views
    Eruption imminent gameplay part 19
    06:16
    Eruption imminent gameplay part 19
    Amaran
    4.1K views
    Wife with strap on swaps
    01:08
    Wife with strap on swaps
    726.9K views
    19 Years Old Blonde Girl Fucked Hard by Grey Hair Futanari in Public Alley
    05:36
    19 Years Old Blonde Girl Fucked Hard by Grey Hair Futanari in Public Alley
    Asura
    3.9K views
    Husband lends wife to tranny fucks her
    27:29
    Husband lends wife to tranny fucks her
    854.4K views
    The thickening game play part 21
    06:49
    The thickening game play part 21
    Amaran
    1K views
    Guy Surprised That She Has a Dick
    26:24
    Guy Surprised That She Has a Dick
    3.6M views
    Eruption imminent gameplay part 20
    05:59
    Eruption imminent gameplay part 20
    Amaran
    2.7K views
    BBC Addiction - MY wife lovec big black cock
    15:05
    BBC Addiction - MY wife lovec big black cock
    tattooedb
    41.9K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to First Time Cuckolding

    • Step Brother Cum Inside Step Sister
    • Japanese Mother in Law Uncensored
    • Beautiful Girl Very Hard Fucking
    • Caught Crossdressing by Mom
    • Younger Schoolgirl Getting Fucked
    • Wife Sharing
    • Stepmoms Trans Stepsister Surprise Visit
    • First Time With Stepmom
    • Boy and Older Women
    • Homemade Cuckold Humiliation
    • Pretty
    • Gorgeous Shemale
    • Shy Wife Shared
    • Love Sexxxx
    • Hot Sex
    • Turning Cuck Husband Into Faggot
    • Bad Mommy
    • Virgin Teen 18 Girlfriend Ki Chudai
    • Hotel Room XXX
    • Just Let's Keep This a Secret Okay

    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