PornPorn Transgender • US
  • Videos
  • Short videos
  • photos
  • Users
    Forgot password
    Sign in with Google
    Sign in with X
    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
    • Black
    • Big Cock
    • 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
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Black
    • Big Cock
    • Shemale Fucks Shemale
    • Amateur
    • Shemale Fucks Girl
    • Sissy
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Big Black Cock
    • Cum In Mouth
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    First Time Pegging Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    First Time Ladyboy
    Trans Pegging
    Femboy First Time
    Straight First Time
    Wife Pegging
    Pegging Femboy
    First Time Tranny
    First Time Lesbian
    First Creampie
    Amateur First Time
    First Ladyboy
    Pegging Cum
    Straight First
    First Time Sucking
    First Time Sex
    First Time BBC
    First Time Bottom
    First Cock
    Pegging Compilation
    Futa Pegging
    Best Videos
    By clicking the content you will also see an ad. AD
    Zoe and Jane strapon
    05:11
    Zoe and Jane strapon
    147.8K views
    First Time Anal
    08:41
    First Time Anal
    Pure Ts
    86.7K views
    He filled my ass with it, his drips a lot
    07:53
    He filled my ass with it, his drips a lot
    Piou_Sissy
    272.7K views
    My first time with a trans girl !!
    14:58
    My first time with a trans girl !!
    Lina Mila
    2.1M views
    Hardcore Pegging using my slave's ass to the limit
    02:21
    Hardcore Pegging using my slave's ass to the limit
    Revenge
    337.2K views
    First Time Glory Hole
    09:03
    First Time Glory Hole
    447.3K views
    boy first time with trans
    10:18
    boy first time with trans
    433.5K views
    Blonde gurl's first time.
    04:01
    Blonde gurl's first time.
    1.3M 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
    2.4M 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
    2.9M views
    POV Hard Pegging Jasmine Dlight From Mistress
    02:17
    POV Hard Pegging Jasmine Dlight From Mistress
    Jasmine_dlight
    157.4K views
    My first time with a real transsexual...
    08:12
    My first time with a real transsexual...
    She-Male X
    676.1K views
    Intense pegging at the hotel for Loren Aprile
    02:16
    Intense pegging at the hotel for Loren Aprile
    Loren Aprile
    156.9K views
    FEMOUT XXX - First Time Black Teen petite Tgirl masturbates
    03:11
    FEMOUT XXX - First Time Black Teen petite Tgirl masturbates
    Femout
    670.6K views
    I Fuck a Beautiful 19-year-old Trans Girl with a Big Dick
    08:12
    I Fuck a Beautiful 19-year-old Trans Girl with a Big Dick
    FapHouse
    2.1M 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
    Sissy Femboy Fucked From Behind
    05:20
    Sissy Femboy Fucked From Behind
    2.7M views
    FEMOUT - Cutie Pixie Pond First Time To Show Her Goodies
    03:12
    FEMOUT - Cutie Pixie Pond First Time To Show Her Goodies
    Femout
    22.1K views
    Anal Hike and Humiliation for TS Slave Loren Aprile
    02:09
    Anal Hike and Humiliation for TS Slave Loren Aprile
    Loren Aprile
    421.5K 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
    756.8K views
    your first time: she will slowly stretch you and then fuck u
    02:20
    your first time: she will slowly stretch you and then fuck u
    722.7K 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
    Fucking like a little bitch
    15:52
    Fucking like a little bitch
    Piou_Sissy
    146.4K 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.
    FapHouse
    928.6K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.7M views
    Beograd first time with transgirl
    01:59
    Beograd first time with transgirl
    402K views
    Guy Gets His Balls Tied up in Threesome and Gets Anal Fucked by Tranny
    24:55
    Guy Gets His Balls Tied up in Threesome and Gets Anal Fucked by Tranny
    Shemale TS Collection
    89K views
    Your Very First Time - Trans Femdom GFE with Melissa Masters
    03:40
    Your Very First Time - Trans Femdom GFE with Melissa Masters
    Many Vids
    369.7K views
    Her friends first time taking dick
    03:39
    Her friends first time taking dick
    500.1K views
    My First Time With a BBC
    08:45
    My First Time With a BBC
    388.9K views
    Sissy CUM Free Hands!! After HOT ANAL FUCK
    08:35
    Sissy CUM Free Hands!! After HOT ANAL FUCK
    Lola Spais
    328.1K 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
    Tricking my neighbor and fucking his ass
    03:49
    Tricking my neighbor and fucking his ass
    Elizabeth Stewart
    602.3K views
    FEMOUT - Introducing The Valentine Fox First Time Lust
    03:12
    FEMOUT - Introducing The Valentine Fox First Time Lust
    Femout
    18.5K 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
    First time with my TS stepsister
    01:37
    First time with my TS stepsister
    David Rey
    564.6K views
    I had my first sex, he came inside me :(
    05:08
    I had my first sex, he came inside me :(
    cd_aysemmm
    118.3K 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
    76.6K views
    Mistress Revenge Destroying my Ass in her hotel room
    01:51
    Mistress Revenge Destroying my Ass in her hotel room
    Loren Aprile
    232.4K 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
    Pegging by Monster BBC Strapon
    04:48
    Pegging by Monster BBC Strapon
    Many Vids
    7.4K views
    The first time I take a dick in my ass
    02:55
    The first time I take a dick in my ass
    355K views
    Trap takes BWC for the first time from daddy
    00:54
    Trap takes BWC for the first time from daddy
    3M views
    First Time Trans Alice Gets Wrecked
    08:12
    First Time Trans Alice Gets Wrecked
    FapHouse
    85.8K 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
    FapHouse
    365.9K views
    FEMOUT - Meet and Discover Taylor First Time
    03:12
    FEMOUT - Meet and Discover Taylor First Time
    Femout
    15.4K views
    Daddy Milks Trans Girl Prostate
    05:06
    Daddy Milks Trans Girl Prostate
    Gray Perrier
    348.8K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to First Time Pegging

    • Taking Virginity
    • Crossdresser Pegged by Woman
    • Multiple Continuous Cum 10 Times
    • Extreme Insertion
    • Destroying the Fag
    • Riding Until She Cums
    • Real Caught on Camera
    • Femdom Emasculation
    • In Front of Friends
    • Black Domination White Submissive
    • Permanent Sissification
    • Takes Condom off
    • Rough Pounding
    • Most Feminine Girl Ever
    • Swallow After Anal
    • No Going Back
    • Power Bottom
    • Edging Fail
    • 18 Yo Trap Unloads
    • Jerk From Behind
    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