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 Pegging For Virgin Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Pegging
    First
    Virgin
    Time
    First Time Virgin
    First Time Sissy
    First Time
    Sissy Pegging
    Sissy Virgin
    Sissy Time
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Best Videos
    By clicking the content you will also see an ad. AD
    Please Help me!
    05:17
    Please Help me!
    Dly guy
    2.4K views
    Familyfuck- Full Sex girls gay and shemal fucking hardcore video
    11:20
    Familyfuck- Full Sex girls gay and shemal fucking hardcore video
    Xmama963
    3K views
    Guy Feminized and Fucked for First Time
    03:17
    Guy Feminized and Fucked for First Time
    Bailey Wilde
    39.7K views
    Sissy crossdressing Madison CD rides a BBC dildo as she Crossdresser in lingerie  and stockings
    05:27
    Sissy crossdressing Madison CD rides a BBC dildo as she Crossdresser in lingerie and stockings
    MadisonCD2025
    993 views
    Sissy Michaela playin
    10:31
    Sissy Michaela playin
    Michaela Pink
    1K views
    Asian Satanic Sissy - First Time BBC Fuck and Cum On Face
    06:04
    Asian Satanic Sissy - First Time BBC Fuck and Cum On Face
    52.3K views
    MY FIRST TIME FUCK BEAUTIFUL SHEMALE ON UPSTAIRS
    19:58
    MY FIRST TIME FUCK BEAUTIFUL SHEMALE ON UPSTAIRS
    Altmodelbox
    22.9K views
    Black Latina Trans Black Sharon plays with a strong erection on her big milky cock
    05:35
    Black Latina Trans Black Sharon plays with a strong erection on her big milky cock
    Blacksharon
    39.6K views
    skinny teen femboy getting fucked first time
    08:12
    skinny teen femboy getting fucked first time
    Fembaby
    25.8K views
    My pastor wife.
    06:12
    My pastor wife.
    Badman4606
    2.3K views
    Mommy Holy - JOI CEI - your first time cum eating - Red Light Green Light
    11:55
    Mommy Holy - JOI CEI - your first time cum eating - Red Light Green Light
    Holy
    15K views
    The first time Star GiGiMoon gets her beautiful ass fucked with t purple dildo and enjoys playing with her wonderful little hole
    05:25
    The first time Star GiGiMoon gets her beautiful ass fucked with t purple dildo and enjoys playing with her wonderful little hole
    GiGiMoon81
    18.9K views
    Amateur Dad And Boy First Time
    09:42
    Amateur Dad And Boy First Time
    Rose Andersen Lush
    7.1K views
    Sissy Crossdresser drips cum and taste and then talks dirty to the camera
    05:34
    Sissy Crossdresser drips cum and taste and then talks dirty to the camera
    MadisonCD2025
    just added
    Sissy plays with anal plug for the first time
    02:35
    Sissy plays with anal plug for the first time
    Vejenity
    11K views
    Slutty Crossdresser uses anal toy to masturbate her ass
    05:25
    Slutty Crossdresser uses anal toy to masturbate her ass
    MadisonCD2025
    1.2K views
    Sissy on the beach
    04:38
    Sissy on the beach
    Sissy Paige
    34.9K views
    My first time to try 15 inch King Cock with high speed fucking machine
    08:08
    My first time to try 15 inch King Cock with high speed fucking machine
    Ylvis88
    42.2K views
    Diva bitch-300 lovers in the future after this long wait!lol
    05:02
    Diva bitch-300 lovers in the future after this long wait!lol
    Karma Rainbow Smith D
    81.1K views
    Amateur Crossdress Madison CD drips cum from fet little clit onto a dildo and then sucks the dildo like the slut she is
    05:23
    Amateur Crossdress Madison CD drips cum from fet little clit onto a dildo and then sucks the dildo like the slut she is
    MadisonCD2025
    700 views
    Weard My Unclean Favorite Panties for Sissy PRO Test & Teacher Got Me Weird
    08:25
    Weard My Unclean Favorite Panties for Sissy PRO Test & Teacher Got Me Weird
    Asura
    4.2K views
    Sexy sexy sexy
    06:14
    Sexy sexy sexy
    Karma Rainbow Smith D
    41.6K views
    First BBC fucking me wearing chastity
    03:33
    First BBC fucking me wearing chastity
    34.2K views
    My first time hilting the Artemis 115
    08:03
    My first time hilting the Artemis 115
    Ylvis88
    2.4K views
    Wonder Woman into Reality and Wanna Be Treated as My Slut
    05:08
    Wonder Woman into Reality and Wanna Be Treated as My Slut
    Asura
    7K views
    Eleanor's Girthier Cock Massages My Teen P-Spot Lead to Cum Leaking
    07:24
    Eleanor's Girthier Cock Massages My Teen P-Spot Lead to Cum Leaking
    Asura
    3.9K views
    Anal Training. First Time Using Big Dildo. I Give Up, That's Hurt
    01:52
    Anal Training. First Time Using Big Dildo. I Give Up, That's Hurt
    MaureenNadh
    37.1K views
    Big Butt Booty Slut Crossdresser Sissy Gay White Ass Sexy Dress
    05:26
    Big Butt Booty Slut Crossdresser Sissy Gay White Ass Sexy Dress
    Crossdresserkitty
    80.1K views
    Trans Fuck Girl in the Ass First Time
    01:15
    Trans Fuck Girl in the Ass First Time
    Lola Spais
    25.9K views
    Stepdad watches my gay ass
    05:29
    Stepdad watches my gay ass
    Buddy rider
    10.6K views
    The Pirate Queen's Personal Boytoy
    07:29
    The Pirate Queen's Personal Boytoy
    Asura
    3.5K views
    Handless cumshot cute ladyboy cock
    06:19
    Handless cumshot cute ladyboy cock
    Crossdresserkitty
    22K views
    Trip Of A Life Time
    10:56
    Trip Of A Life Time
    Asura
    2.6K views
    (Part 1) First Time Tasting My Own Cum And Drinking Piss, Cum On Food Fetish, Asian Transgender Trap Shemale
    09:06
    (Part 1) First Time Tasting My Own Cum And Drinking Piss, Cum On Food Fetish, Asian Transgender Trap Shemale
    MaureenNadh
    27.9K views
    My first and in my mouth.
    08:38
    My first and in my mouth.
    Veronika37vera
    18.8K views
    Crossdressing Confessions: Sharing My Personal Stories and Experiences!
    26:35
    Crossdressing Confessions: Sharing My Personal Stories and Experiences!
    Crossdresserkitty
    6K views
    Multiple Cumshots Skinny Crossdresser Sissy CD Cums Over Herself with Big Cock.
    01:48
    Multiple Cumshots Skinny Crossdresser Sissy CD Cums Over Herself with Big Cock.
    JazzabelleCD
    2.7K views
    Let's Go One More Than... Futanari Ashe Cumming A Lot After Getting Caught By Evelyn
    05:34
    Let's Go One More Than... Futanari Ashe Cumming A Lot After Getting Caught By Evelyn
    Asura
    4.4K views
    Males are Gentle Flowers! You Gotta Be Kind!
    05:51
    Males are Gentle Flowers! You Gotta Be Kind!
    Asura
    4.3K views
    Fucking my 18 year old girlfriend for the first time
    08:02
    Fucking my 18 year old girlfriend for the first time
    Dessietsa
    56.2K views
    First Time I Go 100% Balls Deep on This One 42cm, 16 Inch
    01:54
    First Time I Go 100% Balls Deep on This One 42cm, 16 Inch
    boobyb0y
    9K views
    Sissy precum for the first time
    10:27
    Sissy precum for the first time
    4.4K views
    my first time with a sex machine it can get my honey out but its the real cock i miss the most when im single
    05:08
    my first time with a sex machine it can get my honey out but its the real cock i miss the most when im single
    BCtranny
    27K views
    Redhead trans schoolgirl, rich, deep throat oral sex
    05:09
    Redhead trans schoolgirl, rich, deep throat oral sex
    Sexytransjordana25
    2.5K views
    Naughty Winterslut Sensual Spanking
    08:05
    Naughty Winterslut Sensual Spanking
    miikakawaiii
    826 views
    Sissy Lisa tries her Hismith for the first time
    01:28
    Sissy Lisa tries her Hismith for the first time
    36.6K views
    Stretch my asshole wide open
    06:33
    Stretch my asshole wide open
    Badman4606
    3K views
    • Back
    • 1
    • ...
    • 5
    • 6
    • 7
    • 8
    • 9
    • ...
    • 80
    • Next

    Searches Related to First Time Pegging For Virgin Sissy

    • New Crossdresser
    • Whore Training
    • Silver Daddies
    • Cant Handle
    • Aggressive Top
    • Take Like Bitch Boy
    • Lost Bet Blowjob
    • Bareback Hooker
    • Sissyfication Process
    • Sloppy Seconds
    • Love Making Sensual Slow Passionate
    • Free Trapped and Fucked
    • Pattaya Walking Street Ladyboy Bar Strip
    • Babydoll
    • Anonymous Motel
    • Grace Charis Nude Golf
    • No Mercy
    • Men Dressed as Women
    • Small Penis Massage
    • Make Him Moan

    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