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 Anal Failed Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos

    Did you mean first time anal nailed?

    Brazilian Anal
    Pantyhose Anal
    Anal Licking
    Anal Curvy
    Anal Whore
    Anal Ball
    Anal Fingering
    Bi Anal
    Office Anal
    Submissive Anal
    Anal Training
    Taboo Anal
    Anal Domination
    French Anal
    Bisexual Anal
    Futanari Anal
    Missionary Anal
    Italian Anal
    Anal Humiliation
    Thailand Anal
    Best Videos
    By clicking the content you will also see an ad. AD
    Fucking the virgin ass of an 18 year old boy for the first time
    09:46
    Fucking the virgin ass of an 18 year old boy for the first time
    Dessietsa
    25.5K views
    VRB TRANS First Time TS Call Girl Experience
    05:01
    VRB TRANS First Time TS Call Girl Experience
    VRbtrans
    27.4K views
    I want an old man to fuck me in the ass for the first time
    10:40
    I want an old man to fuck me in the ass for the first time
    Dessietsa
    12.8K views
    Rookie TS Arielly Miller Has Machine Sex for the First Time
    08:05
    Rookie TS Arielly Miller Has Machine Sex for the First Time
    Dream Tranny
    12K views
    petite tranny undresses for the first time and shows what a horny cock she has
    13:24
    petite tranny undresses for the first time and shows what a horny cock she has
    Eroticonly
    28.1K views
    Sissi Young first time dildo  Assgasm
    04:26
    Sissi Young first time dildo Assgasm
    S Sissy Slut Nina
    6.7K views
    Crossdresser First Time Using Dildo
    02:06
    Crossdresser First Time Using Dildo
    13K views
    Roommate Feminized and in Chastity for First Time for Girls Night Out
    01:50
    Roommate Feminized and in Chastity for First Time for Girls Night Out
    Onlyfans
    7.9K views
    My first time fucking trans man
    05:33
    My first time fucking trans man
    Onlyfans
    140.5K views
    My Fat Trans Ass Gets Fucked by a Black Cock For the First Time.
    14:40
    My Fat Trans Ass Gets Fucked by a Black Cock For the First Time.
    fermerino
    6.1K views
    First time with a Shemale
    01:27
    First time with a Shemale
    56.7K views
    GROOBYDVD: Femout First Time Fuckers #2
    02:08
    GROOBYDVD: Femout First Time Fuckers #2
    Femout
    37.2K views
    Trans Girl plays with an 18 cm Dildo for the first time, Moans from pain but ends up liking it  Succubo16
    29:58
    Trans Girl plays with an 18 cm Dildo for the first time, Moans from pain but ends up liking it Succubo16
    LaRicura16
    11.2K views
    Chubby Teen Trans girl plays with her puffy nipples and Sits on a dildo for the first time
    05:12
    Chubby Teen Trans girl plays with her puffy nipples and Sits on a dildo for the first time
    fermerino
    15.8K views
    thai girl taste big shemale cock first time
    15:10
    thai girl taste big shemale cock first time
    Altmodelbox
    33.3K views
    Asian Crossdresser Turns Satanic Sissy Bitch First Time 1
    03:30
    Asian Crossdresser Turns Satanic Sissy Bitch First Time 1
    7.6K views
    BOYFRIEND GIVING HIS GIRFRIEND IN THE ASS FOR THE FIRST TIME
    05:40
    BOYFRIEND GIVING HIS GIRFRIEND IN THE ASS FOR THE FIRST TIME
    10.4K views
    GORGEOUS BRUNETTE WITH WET PUSSY TASTE SHEMALE COCK FIRST TIME
    23:12
    GORGEOUS BRUNETTE WITH WET PUSSY TASTE SHEMALE COCK FIRST TIME
    Altmodelbox
    10.7K views
    Shemale tries hollow anal plug, anal stretcher for the first time
    05:20
    Shemale tries hollow anal plug, anal stretcher for the first time
    Lucas Nathan King
    5.9K views
    Virgin Sissy Housewife Fucked with Dildo for the First Time
    12:44
    Virgin Sissy Housewife Fucked with Dildo for the First Time
    SissyHousewife
    3.2K views
    Big Dick Latino Fucks Ladyboy Anal for the First Time
    23:12
    Big Dick Latino Fucks Ladyboy Anal for the First Time
    FapHouse
    1.3K views
    My First Time as a Sissy
    06:12
    My First Time as a Sissy
    FapHouse
    just added
    Kawaii Anime Emo Trap Rides BBC Dildo for First Time
    00:34
    Kawaii Anime Emo Trap Rides BBC Dildo for First Time
    Cristy Noir
    43.9K views
    Sissy Schoolgirl my First time Fucking my Ass with a Sex Machine BBC Dildo
    10:23
    Sissy Schoolgirl my First time Fucking my Ass with a Sex Machine BBC Dildo
    Mariana Taylor
    5.6K views
    Sissy Tries Butt Plug and Chastity For The First Time - Sissy Housewife
    18:40
    Sissy Tries Butt Plug and Chastity For The First Time - Sissy Housewife
    SissyHousewife
    5.8K views
    Be gentle this is my first time with a tranny
    16:11
    Be gentle this is my first time with a tranny
    Tranny Newbies
    13.9K views
    Guy Decides to Dress in Drag for the First Time
    02:20
    Guy Decides to Dress in Drag for the First Time
    Onlyfans
    3.5K views
    First time  ever taking a 14 inch
    03:10
    First time ever taking a 14 inch
    FapHouse
    1.1K views
    First Time Fembois with Thayane Beck for TrannyBizzare
    06:29
    First Time Fembois with Thayane Beck for TrannyBizzare
    Tranny Bizarre
    17K views
    RebeccaCD - First time a real cock in the ass
    05:21
    RebeccaCD - First time a real cock in the ass
    7.9K views
    Sissy Autumn first time with Daddy
    01:57
    Sissy Autumn first time with Daddy
    4.5K views
    Sissy tries bigger toy for first time, gets surprised
    08:06
    Sissy tries bigger toy for first time, gets surprised
    Jana the Great
    1.9K views
    Sissy First Time Big Dildo
    01:36
    Sissy First Time Big Dildo
    FapHouse
    1.8K views
    First time with my Hismith machine
    36:33
    First time with my Hismith machine
    19.6K views
    Blonde Sissy Riding Her Dildo In Her Latex Suit For The First Time
    14:03
    Blonde Sissy Riding Her Dildo In Her Latex Suit For The First Time
    LoLiLights
    11.7K views
    Hoping to experience my first time with Anal
    00:54
    Hoping to experience my first time with Anal
    22.5K views
    Wearing Garter for the first time
    05:23
    Wearing Garter for the first time
    Your Toy
    5.9K views
    My Sissy Fat Ass Trying a Vibrator for the First time
    07:16
    My Sissy Fat Ass Trying a Vibrator for the First time
    fermerino
    2.5K views
    This is our first time having a threesome with a shemale
    14:16
    This is our first time having a threesome with a shemale
    Shemales Fuck Couples
    27.7K views
    my first time in soubrette sissy
    19:01
    my first time in soubrette sissy
    16.9K views
    Slutypia rides first time ass wide open it hurts so good
    00:53
    Slutypia rides first time ass wide open it hurts so good
    10K views
    Sissy Supergirl First Time With Dildo
    16:04
    Sissy Supergirl First Time With Dildo
    Sissy Shelby Kiss
    4.8K views
    GLORIUS PUSSY TRY FIRST TIME GAINT SHEMALE COCK AND LOVE IT
    15:08
    GLORIUS PUSSY TRY FIRST TIME GAINT SHEMALE COCK AND LOVE IT
    Pleasure Fucktory
    15.4K views
    Being fisted for the first time in the woods
    00:44
    Being fisted for the first time in the woods
    8.9K views
    Guy Feminized and Strapon Fucked for First Time
    00:49
    Guy Feminized and Strapon Fucked for First Time
    Bailey Wilde
    3.5K views
    It is my First Time Fembois
    08:12
    It is my First Time Fembois
    Horny Shemales
    622 views
    First time in bondage
    20:49
    First time in bondage
    KANAe
    8.5K views
    • Back
    • 1
    • ...
    • 6
    • 7
    • 8
    • 9
    • 10
    • ...
    • 80
    • Next

    Searches Related to First Time Anal Failed

    • My Wife S Boyfriend Fuck My Ass
    • Monster Cock Shemale Makes Guy Scream
    • Leo Ahsoka Leaked
    • Boy First Time With Trans
    • Massage Parlor Surprise
    • Small Dick
    • Boy and Boy XXX
    • Shemale Cums in Guys Ass Compilation
    • Asian Tranny Enjoys Sex With Mike
    • Small Dick Cum in Mouth
    • Thai Teen Anal
    • Guy Sucking Shemale Cock and Eating Cum
    • Beautiful Ladyboy Stroking Her Big Cock
    • 18 Year Old Amateur
    • Thai Trans Massage
    • Sissy Cumming With Small Soft Cock
    • Best Blowjob Ever
    • Sissy Boy Getting Fucked Hard
    • Thai Hotel
    • Trans XXX Telegram
    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