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
    • Bareback
    • Creampie
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Cuckholding First Time Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    First
    Time
    First Time
    Young First Time
    Crossdresser First Time
    First Time Shemale
    First Time Virgin
    First Time Anal
    Homemade First Time
    Cd First Time
    First BBC
    First Date
    First Time Trans
    Sissy First Time
    First Time Ladyboy
    Adult Time
    First Trans
    First Time Sucking
    First Blowjob
    Straight First Time
    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
    Cuckhold gets Fucked by the Wife's Bull Fiona Fortune Sissy CD Cuck
    14:12
    Cuckhold gets Fucked by the Wife's Bull Fiona Fortune Sissy CD Cuck
    Fiona Fortune
    106.5K 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
    609K views
    Cuckhold's secrets
    18:11
    Cuckhold's secrets
    156.9K 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
    382.7K views
    Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time - Trans Angels
    10:25
    Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time - Trans Angels
    Trans Angels
    9M 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
    First Time Anal
    08:41
    First Time Anal
    Pure Ts
    62.7K views
    Guy gets fooled into sex with a shemale
    06:15
    Guy gets fooled into sex with a shemale
    Love4TS
    2.6M views
    Trap takes BWC for the first time from daddy
    00:54
    Trap takes BWC for the first time from daddy
    3M views
    surprise she has dick
    07:34
    surprise she has dick
    251.5K views
    My first time with a trans girl !!
    14:58
    My first time with a trans girl !!
    Lina Mila
    2.1M 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
    280.7K views
    HIS FIRST TIME FUCKED BY A LADYBOY AND HE CUM
    01:12
    HIS FIRST TIME FUCKED BY A LADYBOY AND HE CUM
    1M views
    Hostel Surprise
    37:09
    Hostel Surprise
    3.1M views
    First Time Glory Hole
    09:03
    First Time Glory Hole
    434.1K views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.2M views
    MY STEPBROTHER WANTS TO TRY FOR THE FIRST TIME WITH A TRANS GIRL
    20:51
    MY STEPBROTHER WANTS TO TRY FOR THE FIRST TIME WITH A TRANS GIRL
    yesid
    1.1M views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.3M views
    Blonde gurl's first time.
    04:01
    Blonde gurl's first time.
    1.3M views
    Ultimate cuckold tranny humiliation!
    05:36
    Ultimate cuckold tranny humiliation!
    Femdom Austria TS
    61.5K views
    First time with a tranny (shemale) and we enjoy tasty cock
    07:11
    First time with a tranny (shemale) and we enjoy tasty cock
    2.8M views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.1M views
    My first time with a real transsexual...
    08:12
    My first time with a real transsexual...
    She-Male X
    656.1K views
    family fun 1.mp4
    13:05
    family fun 1.mp4
    1.7M views
    TRANS ANGELS - Izzy Wilde Meets Her Stepbro Sage Roux For The First Time And In No Time Gets His Cock Out To Suck - TRANS ANGELS
    10:25
    TRANS ANGELS - Izzy Wilde Meets Her Stepbro Sage Roux For The First Time And In No Time Gets His Cock Out To Suck - TRANS ANGELS
    Trans Angels
    741.6K views
    Surprise! She has a cock!
    00:49
    Surprise! She has a cock!
    295.3K views
    FEMOUT - Cutie Pixie Pond First Time To Show Her Goodies
    03:12
    FEMOUT - Cutie Pixie Pond First Time To Show Her Goodies
    Femout
    14.7K views
    Tricking my neighbor and fucking his ass
    03:49
    Tricking my neighbor and fucking his ass
    Elizabeth Stewart
    587.1K views
    FEMOUT XXX - First Time Black Teen petite Tgirl masturbates
    03:11
    FEMOUT XXX - First Time Black Teen petite Tgirl masturbates
    Femout
    640K views
    My stepmom is a tranny
    16:46
    My stepmom is a tranny
    Combat zone transsexual barebacking
    1M views
    Goth trans girl gets fucked for the first time by a big cock and gets horny by being recorded
    08:05
    Goth trans girl gets fucked for the first time by a big cock and gets horny by being recorded
    Saranji
    62.6K views
    Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune
    13:12
    Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune
    Fiona Fortune
    209.8K views
    Beograd first time with transgirl
    01:59
    Beograd first time with transgirl
    389.9K 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
    first time taking BWC in ass and i like it. Part 2
    00:39
    first time taking BWC in ass and i like it. Part 2
    1M views
    Another straight guy getting tricked by this hot tgirl
    26:17
    Another straight guy getting tricked by this hot tgirl
    1.1M views
    Young guy fucked in the ass for the first time by a tranny
    17:25
    Young guy fucked in the ass for the first time by a tranny
    1M views
    You will never forget your first time with shemale babe Mel
    12:07
    You will never forget your first time with shemale babe Mel
    Tranny Newbies
    1M views
    First time with my TS stepsister
    01:37
    First time with my TS stepsister
    David Rey
    549.7K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    1.8M views
    M584G02 My son who has returned for the first time in a few years is a transcendental transsexual.
    01:29:57
    M584G02 My son who has returned for the first time in a few years is a transcendental transsexual.
    M MBM3988
    897.8K views
    Facefucking My Boy Til I Flood His Throat in My Girlcum
    05:48
    Facefucking My Boy Til I Flood His Throat in My Girlcum
    Elizabeth Stewart
    400.4K 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
    361.8K views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    1.8M views
    My First Time With a BBC
    08:45
    My First Time With a BBC
    381.1K views
    How I've made my boyfriend into a anal slut
    04:39
    How I've made my boyfriend into a anal slut
    Trinit Noir
    53.7K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Cuckholding First Time

    • Wife Taking Black Cock
    • Swallowing Strangers Cum
    • Sucking Very First BBC
    • Cumming in Guys Mouth
    • Surprise I Have a Dick
    • Shemale Surprises Guy
    • Cuckold Humiliation
    • Cuming While Being Fucked
    • My Wife's Boyfriend Fuck My Ass
    • Turning Cuck Husband Into Faggot
    • Crossdresser Caught Fucking Dildo
    • Maybe the Best Cocksucker
    • Giving Him an Experience
    • Reverse Cowgirl
    • Oral Domination
    • Cumdump
    • Unexpected Gangbang
    • White Femboys Are so Submissive
    • Extreme Dirty Talking
    • Married Straight Man Breeds Again

    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