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
    -50%
    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
    50% OFF Tokens for XXXmas Warm up your nights on xHamsterLive with someone special!
    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
    • Bareback
    • Creampie
    • Cumshot
    • Homemade
    • Mature
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    First Time Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    First
    Time
    First Time
    Sissy Time
    Sissy First Time Anal
    Sissy Crossdresser First Time Anal
    Sissy Sucking Cock for First Time
    First Time Pegging for Virgin Sissy
    Sissy Take Dildo First Time Video
    Sissy Virgin Bred for the First Time
    Sissy Crossdresser
    Sissy Training
    Sissy Feminization
    Bbc Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Fucked
    Young Sissy
    Sissy Compilation
    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
    2.9M 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
    5.3K views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.2M views
    First Time Sissy
    00:49
    First Time Sissy
    Danja41
    2.3K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    1.7M views
    First Time Anal
    08:41
    First Time Anal
    Pure Ts
    54.6K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2M views
    Straight First Time Explode in Sissy Mouth
    08:34
    Straight First Time Explode in Sissy Mouth
    736.1K 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
    593.7K views
    Fucking with Dragon Dildo First Time
    04:43
    Fucking with Dragon Dildo First Time
    PrincessKitti3
    93.2K views
    19 year old trans fucked hard by stranger in hotel room
    05:38
    19 year old trans fucked hard by stranger in hotel room
    Crystal Phoenix
    115.4K views
    Mommy Holy - JOI CEI - First Time Cum Eating
    11:15
    Mommy Holy - JOI CEI - First Time Cum Eating
    Holy
    137.5K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    668.9K views
    Cute Fat Ass Trans First Time Fuck-machine and Self Footjob
    01:30
    Cute Fat Ass Trans First Time Fuck-machine and Self Footjob
    Melodyfluffington
    83.6K views
    Never Expecting to Be a Sexy Girl
    08:12
    Never Expecting to Be a Sexy Girl
    Pure Ts
    437.6K views
    Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson
    05:29
    Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson
    640.8K views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    1.7M 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
    18.2K views
    Moaning heaps while He came so deep inside me nothing comes
    02:56
    Moaning heaps while He came so deep inside me nothing comes
    Littlemapleberry
    1.6M views
    A slutty college girl wearing date outfits and black pantyhose moans loudly while trying deep anal fingering for the first time
    11:35
    A slutty college girl wearing date outfits and black pantyhose moans loudly while trying deep anal fingering for the first time
    Harinni
    10.8K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.2M views
    SLUTTY TRANNY JSSEMONTZ puts on LINGERIE and sucks a huge bbc for her first time
    02:36
    SLUTTY TRANNY JSSEMONTZ puts on LINGERIE and sucks a huge bbc for her first time
    JsseMontz
    103.9K views
    Sissy Femboy Fucked From Behind
    05:20
    Sissy Femboy Fucked From Behind
    2.6M views
    Sissy Training After First Time Feminization
    12:20
    Sissy Training After First Time Feminization
    Bailey Wilde
    294.2K views
    I turned my straight roommate intro trans wife
    05:20
    I turned my straight roommate intro trans wife
    CutePinkUnicorn
    424.6K views
    FEMOUT XXX: Lemmi's First Time!
    03:01
    FEMOUT XXX: Lemmi's First Time!
    Femout
    232.9K 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
    Sissy Sucking Cock First Time on Video
    01:18
    Sissy Sucking Cock First Time on Video
    49K views
    Sissy CD sucks and is fucked
    08:25
    Sissy CD sucks and is fucked
    1.4M views
    Onlyfans fan fucks me for the first time
    07:08
    Onlyfans fan fucks me for the first time
    SLU77Y
    10.4K views
    Stepdaddy fuck trans 20yo stepdaughter
    08:53
    Stepdaddy fuck trans 20yo stepdaughter
    Crystal Phoenix
    357K views
    First Time Taste Drink My Own Cum. Handjob And Double Cum
    08:19
    First Time Taste Drink My Own Cum. Handjob And Double Cum
    MaureenNadh
    107.4K views
    Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
    08:12
    Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
    nbnabunny
    1.6M views
    First Time trying Split Screen with the Endoscope in my Dick - Full Video on manyvids and Fansly
    01:18
    First Time trying Split Screen with the Endoscope in my Dick - Full Video on manyvids and Fansly
    Lina Free
    20.2K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.5M views
    What's Russian for Suck My Cock? First Time Girl Fucked by TS Teacher
    06:12
    What's Russian for Suck My Cock? First Time Girl Fucked by TS Teacher
    TS Pussy Hunters by Kink
    2K views
    Boys will be girls and all white trash will be smash
    10:34
    Boys will be girls and all white trash will be smash
    Latina Tranny
    1.2M views
    Sissy Crossdresser Fucks Dildo Doggystyle (first time)
    04:25
    Sissy Crossdresser Fucks Dildo Doggystyle (first time)
    161.6K views
    Daddy's Good Girl!
    08:12
    Daddy's Good Girl!
    Pure Ts
    866.8K views
    His first time with a transgender
    31:09
    His first time with a transgender
    EmmaInkTrans
    2.7K 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
    barbanegrazponto1onepov
    2M views
    Femboy first time anal dildo
    03:26
    Femboy first time anal dildo
    Vejenity
    21.1K 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
    271.9K views
    It's This Sissy Milkboy's First Time
    07:50
    It's This Sissy Milkboy's First Time
    Wraith931
    26.6K views
    Don't do this to me! I do not like it!
    03:01
    Don't do this to me! I do not like it!
    718.3K views
    (Part 2) First Time Tasting My Own Cum And Drinking Piss, Cum On Food Fetish, Asian Transgender Trap Shemale
    08:14
    (Part 2) First Time Tasting My Own Cum And Drinking Piss, Cum On Food Fetish, Asian Transgender Trap Shemale
    MaureenNadh
    76.8K views
    Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    263.6K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to First Time Sissy

    • First Time Being Fucked as Crossdresser
    • Daddy Fucking Sissy Femboy
    • Secret Sissyboy
    • Fuck Me Like a Slut
    • Crossdressing Boy to Girl
    • Tricked Older Straight Man
    • Feminine Boys
    • Homemade Virgin
    • Beautiful Trans Sex
    • Traps Femboys and Sissys
    • Tight Dresses
    • Submissive Transvestite Training
    • Breeding Cds From the Top Position
    • Becoming Femme
    • Taking Virginity
    • Cute Trap
    • Amateur CD
    • Real First Time
    • Sissies in Chastity
    • Sexy Young Crossdressers

    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 - 2025, 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