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

    Sissy Virgin Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Virgin
    Feminized BBC Virgin Sissy
    First Time Pegging for Virgin Sissy
    Sissy Virgin Bred for the First Time
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Sissy Slave
    Amateur Sissy
    Sissy Blowjob
    Sissy Cuckold
    Sissy Gangbang
    Submissive Sissy
    Best Videos
    By clicking the content you will also see an ad. AD
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.6M views
    Horny fem crossdresser sissy virgin Lanalovebums first anal dildo play in stockings
    01:56
    Horny fem crossdresser sissy virgin Lanalovebums first anal dildo play in stockings
    Mrlovebums
    7.8K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    Sissy virgin Lindsey Mai needs a mistress??
    00:23
    Sissy virgin Lindsey Mai needs a mistress??
    826 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
    Sissy virgin showing off again
    06:05
    Sissy virgin showing off again
    Wannit al
    1.5K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    737.5K views
    Turning a straight man into a passive little whore by passionately fucking him with my big cock
    06:15
    Turning a straight man into a passive little whore by passionately fucking him with my big cock
    DotadaSP
    1.4M views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.2M views
    Innocent trans passionately rides and sucks cock
    05:37
    Innocent trans passionately rides and sucks cock
    Ashley Roze
    483.9K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.1M views
    Promo: Scottish virgin gets railed by Katie Fox
    07:32
    Promo: Scottish virgin gets railed by Katie Fox
    Katie Fox
    93.1K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.3M views
    Sissy College Twink Alexis Loses her Virginity
    01:29
    Sissy College Twink Alexis Loses her Virginity
    476.7K views
    Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    279.3K views
    Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson
    05:29
    Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson
    651.2K views
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    29:33
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    Ria_Bentley
    2.5M views
    FN039 Innocent high school student
    13:31
    FN039 Innocent high school student
    Fampfy Nana
    617.7K views
    Daddy's Good Girl!
    08:12
    Daddy's Good Girl!
    Pure Ts
    901.5K views
    Cute Virginal Clit Cumshot
    08:17
    Cute Virginal Clit Cumshot
    Cindy Belfast
    67.7K views

    Relevant Short videos

    Please suck my little trans dick🥺
    Please suck my little trans dick🥺
    SissyGurl_Autumn
    19.9K views
    Hmmm more?
    Hmmm more?
    Anneyxx
    2.9K views
    reverse cowgirl on a BIG BLACK....microphone
    reverse cowgirl on a BIG BLACK....microphone
    Rita Kitty
    6.6K views
    Fucking my little hole with a dildo for the first time
    Fucking my little hole with a dildo for the first time
    samsesang
    7.4K views
    Trans Taking an Anal Virginity
    Trans Taking an Anal Virginity
    Mistress Jodie May
    4.2K views
    Desi sissy boy PRIYA naked outdoor
    Desi sissy boy PRIYA naked outdoor
    Priya sexy
    4K 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
    Your futa friend wants to fuck your virgin ass until you beg for her cum - AI
    05:33
    Your futa friend wants to fuck your virgin ass until you beg for her cum - AI
    Melissa Wet Tales
    27.1K views
    My wife told me to play this
    11:13
    My wife told me to play this
    953.3K views
    POV Taking Cute Sissy's Virginity on the First Date - full vid on LayneLovee Manyvids
    01:20
    POV Taking Cute Sissy's Virginity on the First Date - full vid on LayneLovee Manyvids
    Layne Love
    44.5K views
    Male to female gender transformation smoking whore
    16:00
    Male to female gender transformation smoking whore
    684.1K views
    sexy and sissy Thai femboy masturbating her cock and she cum
    09:54
    sexy and sissy Thai femboy masturbating her cock and she cum
    Nikki Ladyboys
    297.2K views
    I got on Grindr got fucked and had multiple sissygasms
    04:09
    I got on Grindr got fucked and had multiple sissygasms
    OneWhoHasFun
    156.8K views
    ''True Story''- My 1st Fuck- Crossdresser Vid diary on the day she 1st got fucked
    02:03
    ''True Story''- My 1st Fuck- Crossdresser Vid diary on the day she 1st got fucked
    JessieBlack
    97.7K views
    dominant stepmom helps out her sissy slave
    05:59
    dominant stepmom helps out her sissy slave
    Pure Ts
    352.8K views
    A mature man takes the innocence of an effeminate young transvestite  boy
    05:16
    A mature man takes the innocence of an effeminate young transvestite boy
    MTFXXXVIDS
    4K views
    My stepmom is a tranny
    16:46
    My stepmom is a tranny
    Combat zone transsexual barebacking
    1.1M views
    The Sound of the SIssy
    09:23
    The Sound of the SIssy
    Laserhands
    43.6K views
    Sissy cums too early and gets punished with rough fucking
    02:35
    Sissy cums too early and gets punished with rough fucking
    2.1M views
    Analing The Virgin Teen Boy's Virgin Ass
    07:52
    Analing The Virgin Teen Boy's Virgin Ass
    Asura
    41.2K 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
    623.1K views
    Young Hairy Virgin Cums In Bed
    08:09
    Young Hairy Virgin Cums In Bed
    Khatara Shikiku
    32K views
    BBC Fucks a Slutty Crossdresser Without Limits
    32:44
    BBC Fucks a Slutty Crossdresser Without Limits
    Trans and Co
    367.4K views
    # Full Duo Video 08:57 - Virgin Riding in Today's Video, I'm Wearing a Virgin Sweater and Sit on Top of Trappybay
    04:43
    # Full Duo Video 08:57 - Virgin Riding in Today's Video, I'm Wearing a Virgin Sweater and Sit on Top of Trappybay
    LalaThePala
    54.6K views
    Never Expecting to Be a Sexy Girl
    08:12
    Never Expecting to Be a Sexy Girl
    Pure Ts
    457K views
    Hazelnut Latte: Sissy Co-worker Loosing Virginity and Got Introduced to Juicy Cock for the First Time - Episode 8
    08:12
    Hazelnut Latte: Sissy Co-worker Loosing Virginity and Got Introduced to Juicy Cock for the First Time - Episode 8
    Dirty GamesxXx
    1K views
    Many crossdressers fucked scrnrs
    01:09:02
    Many crossdressers fucked scrnrs
    1.4M views
    Beautiful 18 year old Virgin Shemale
    10:05
    Beautiful 18 year old Virgin Shemale
    Dessietsa
    145.6K views
    Sissy Femboy Fucked From Behind
    05:20
    Sissy Femboy Fucked From Behind
    2.7M views
    The Secret of an Innocent High School Girl...masturbation with Her Butt
    01:15:20
    The Secret of an Innocent High School Girl...masturbation with Her Butt
    KANAe
    5.3K 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
    212.5K views
    Beta Male Ruined for Life: Sissification, Anal Virginity Taken
    06:27
    Beta Male Ruined for Life: Sissification, Anal Virginity Taken
    Rozebella
    1K views
    Dating a mature crossdresser
    08:12
    Dating a mature crossdresser
    Pure Ts
    220.5K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Virgin

    • Sissy First Time Fucked
    • Virgin Crossdresser
    • Femboy Schoolgirl
    • Secret Sissyboy
    • Caught Crossdressing by Mom
    • A Pretty Boy Gets Feminized
    • Feminine Boys
    • Dirty Crossdressers Slut
    • Traps Femboys and Sissys
    • Transvestites Sissies
    • Crossboy With Mommy Clothes
    • Fucking Cheap Whore
    • Femboy Hookers
    • Crossdressing Daddies
    • Cross Dressing Faggot
    • Crossdress Fuck
    • Boy Dressed as Girl
    • Very Girly Ladyboys
    • Man Transformed Into Woman
    • Femboygirlfriend

    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