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

    The First Time Sex Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sex
    First
    Time
    First Time
    Sex Videos
    Shemale Sex
    Transgender Sex
    Crossdresser First Time
    Rough Sex
    Crossdresser Sex
    Group Sex
    First Time Shemale
    Young First Time
    Lesbians Sex
    Hijra Sex
    Indian Sex
    Best Sex
    Hot Sex
    Sex Xxxn
    Sex Pron
    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
    Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson
    05:29
    Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson
    654.6K views
    Lovely young girl is a shemale with big cock
    08:11
    Lovely young girl is a shemale with big cock
    10.6M views
    Ladyboy for first time sex - KimCock
    05:40
    Ladyboy for first time sex - KimCock
    891.7K views
    Hot T GIRL with college boy.
    29:02
    Hot T GIRL with college boy.
    2.9M views
    Teenage Ladyboy First Time Sex
    17:33
    Teenage Ladyboy First Time Sex
    Ladyboy Homeless
    22.8K views
    Guy gets fooled into sex with a shemale
    06:15
    Guy gets fooled into sex with a shemale
    Love4TS
    2.6M views
    18 years Old Couple First Time Sex When They Alone at Home Hardcore & Hardfuckig Sex
    05:47
    18 years Old Couple First Time Sex When They Alone at Home Hardcore & Hardfuckig Sex
    Peanut Girl
    33.2K views
    He Tears His Cute Trans Roommate's Pantyhose To Bang Her
    10:54
    He Tears His Cute Trans Roommate's Pantyhose To Bang Her
    Devils tgirls
    6.1M views
    First Time Sex Maschine 01 SandraCrossdy
    00:08
    First Time Sex Maschine 01 SandraCrossdy
    SandraCrossDy
    3.2K views
    REAL SHEMALE HOOKER VISIT - German homemade latina cum
    13:29
    REAL SHEMALE HOOKER VISIT - German homemade latina cum
    Transen-von-Nebenan
    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
    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
    636.6K 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
    JockPussy - Petite trans hottie Joey Michaels cumdumps for hung jocks
    10:10
    JockPussy - Petite trans hottie Joey Michaels cumdumps for hung jocks
    Jock Pussy
    2.1M 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
    71.4K views
    Hostel Surprise
    37:09
    Hostel Surprise
    3.1M views
    A curious woman tries a shemale's cock for the first time
    39:01
    A curious woman tries a shemale's cock for the first time
    Pinko TGirls
    1.6M 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
    21.5M views
    Shemale fucks Petite transgirl for the first time in the New Year
    26:23
    Shemale fucks Petite transgirl for the first time in the New Year
    Kapri Sun
    369.9K 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
    402K views
    Freya Frostnymph frotting for the first time
    04:25
    Freya Frostnymph frotting for the first time
    Freya Frostnymph
    271.4K views
    ladyboy teen shower with her daddy then eat her ass and suck her
    24:48
    ladyboy teen shower with her daddy then eat her ass and suck her
    HeShexxx
    2.3M views
    THIS WAS THE FIRST TIME I HAD SEX WITH THIS GUY WHO MADE ME FEEL TOO SENSUAL EVERY TIME HE PENETRATED ME UNTIL I WAS FULL
    11:05
    THIS WAS THE FIRST TIME I HAD SEX WITH THIS GUY WHO MADE ME FEEL TOO SENSUAL EVERY TIME HE PENETRATED ME UNTIL I WAS FULL
    NATALIASTARXXX
    87K views
    Masturbating my trans man's cock while sticking the head of a penis into my pussy
    07:24
    Masturbating my trans man's cock while sticking the head of a penis into my pussy
    TransmanDick
    455K views
    Getting fucked for the first time
    01:25
    Getting fucked for the first time
    81.9K 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
    mandy having sex for the first time
    17:31
    mandy having sex for the first time
    76K views
    2 femboys with puffy nipples make love
    04:27
    2 femboys with puffy nipples make love
    4M views
    Zmsfm & Lm19 Hard anal sex hot tasty slut swallowing huge cock in her tight ass tasty anus gaped for the first time hot ass
    05:12
    Zmsfm & Lm19 Hard anal sex hot tasty slut swallowing huge cock in her tight ass tasty anus gaped for the first time hot ass
    HatanoMiwa
    128.5K 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
    Perverted Couple Hires a Shemale for the First Time for a Threesome
    28:17
    Perverted Couple Hires a Shemale for the First Time for a Threesome
    Shemale TS Collection
    11.8K views
    This happened to me leaving school
    19:20
    This happened to me leaving school
    ELIZABETH LARA
    4.2M views
    My trans girlfriend fucks me for the first time. She loves how she fucks my ass
    28:17
    My trans girlfriend fucks me for the first time. She loves how she fucks my ass
    PalmasRecordsMen
    404.6K views
    Trying to fuck my trans pussy with a huge thick dick
    07:41
    Trying to fuck my trans pussy with a huge thick dick
    TransmanDick
    264K views
    Trans Starlette Throat and Ass Fucked for the first time by a real Porn Star
    07:41
    Trans Starlette Throat and Ass Fucked for the first time by a real Porn Star
    Gray Perrier
    148.5K views
    surprise she has dick
    07:34
    surprise she has dick
    255.4K views
    Boy gets to fuck a CD for the first time
    15:21
    Boy gets to fuck a CD for the first time
    315.4K 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
    Onlyfans fan fucks me for the first time
    07:08
    Onlyfans fan fucks me for the first time
    SLU77Y
    20.5K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M views
    Beautiful 18 year old trans girl fucking for the first time with her new sex toy
    10:10
    Beautiful 18 year old trans girl fucking for the first time with her new sex toy
    Dessietsa
    174.7K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.1M views
    I came twice for the first time Cosplay
    01:38
    I came twice for the first time Cosplay
    Twinkie Star
    261.8K views
    travesti amateur
    04:25
    travesti amateur
    1.7M views
    Trans sucking the cock of the first-time heterosexual in secret
    06:34
    Trans sucking the cock of the first-time heterosexual in secret
    Allison-Nopor
    21.6K views
    My stepmom is a tranny
    16:46
    My stepmom is a tranny
    Combat zone transsexual barebacking
    1.1M views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to The First Time Sex

    • Real Virgin Girl Sex With Boyfriend
    • First Time Getting Fucked
    • School 18 Brazzers 18 XXX
    • I Cum While You Fuck Me
    • Stop Please Stop Dick Too Big
    • Beautiful Teacher Fucks Her Student
    • Hot Sexy Young Woman Xxxxx Black White
    • 19 Year Old UK
    • 2020 Xxxx
    • Sri Lanka Visited Thai Lady Boy
    • Filipino Maid Singapore
    • Lossing Virginity
    • Vintage Classic Family Full Movie
    • Fucking Girlfriend Closeup
    • Retro 1900 1910 1920 1930 1940
    • The Hottest Thing I've Ever Seen
    • Cock so Good She Cums Hands Free
    • English Movies Love Story 2019
    • Princess of Your Dreams
    • Japanese Shemale Schoolgirl

    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