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 NY Ring in 2026 with the right company on xHamsterLive!
    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 Shemale Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Sissy Husband
    Sissy Chastity
    Young Sissy
    Sissy Fucked
    Sissy Compilation
    Amateur Sissy
    Sissy Blowjob
    Sissy Slave
    Sissy Cuckold
    Submissive Sissy
    Sissy Gangbang
    Sissy Femdom
    Sissy Faggot
    Sissy Boy
    Sissy Slut
    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
    sissy Shemale Dildo Trainer
    34:16
    sissy Shemale Dildo Trainer
    505.4K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2M views
    sissy shemale chastity poppertrainer
    18:18
    sissy shemale chastity poppertrainer
    208.8K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    Sissy Shemale Rileydix Rides a Big Black Cock with her Big Fat Yummy Ass!
    10:57
    Sissy Shemale Rileydix Rides a Big Black Cock with her Big Fat Yummy Ass!
    RileyDix
    99.6K 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
    Sissy shemale encouragement
    08:01
    Sissy shemale encouragement
    204K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.2M views
    Sissy shemale tiny penis compilation
    14:42
    Sissy shemale tiny penis compilation
    SissySimran
    799.6K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    706.7K views
    RileyDix sissy shemale takes a bbc in her big ass
    07:52
    RileyDix sissy shemale takes a bbc in her big ass
    RileyDix
    78.7K views
    A guide to sissication: Beginner - Am I a sissy?
    23:32
    A guide to sissication: Beginner - Am I a sissy?
    729.1K views
    Sissy shemale in chastity rides dildo on her pillow with passion and gives him a nice deepthroat
    13:48
    Sissy shemale in chastity rides dildo on her pillow with passion and gives him a nice deepthroat
    Vane03_siss
    5.2K views
    Sissy #2: Becoming A Cock Slut
    15:35
    Sissy #2: Becoming A Cock Slut
    850.6K views
    sissy Shemale PMV 2017
    03:19
    sissy Shemale PMV 2017
    117.5K 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
    Amateur Homemade - White Sissy Shemale BBW Takes a Hard BBC Quickie and Loves It - Candy Ass Sissy
    01:02
    Amateur Homemade - White Sissy Shemale BBW Takes a Hard BBC Quickie and Loves It - Candy Ass Sissy
    Candy Ass Sissy
    19.1K views
    I turned my straight roommate intro trans wife
    05:20
    I turned my straight roommate intro trans wife
    CutePinkUnicorn
    450.5K views
    Femboy cumshot compilation - sissy, shemale, cosplay
    06:43
    Femboy cumshot compilation - sissy, shemale, cosplay
    CutePinkUnicorn
    40.6K views
    SissyFace Sissy Captions Hypno Compilation
    11:18
    SissyFace Sissy Captions Hypno Compilation
    514.7K views
    Little Miss Riding Cock - Beautiful Sissy Shemale With a Hard Little Cock Talks Dirty
    02:17
    Little Miss Riding Cock - Beautiful Sissy Shemale With a Hard Little Cock Talks Dirty
    Ana Keel
    58.3K views
    Sissyfication
    43:09
    Sissyfication
    1M views
    Hot Passionate Love Making With A Sissy Shemale
    05:09
    Hot Passionate Love Making With A Sissy Shemale
    Fat Goddes
    9.9K views
    Male to female gender transformation smoking whore
    16:00
    Male to female gender transformation smoking whore
    674.4K views
    Sissy Shemale sucks Dildo and uses Cum as lube to fuck her ass
    09:08
    Sissy Shemale sucks Dildo and uses Cum as lube to fuck her ass
    Mariana Taylor
    3.1K views
    Lovely young girl is a shemale with big cock
    08:11
    Lovely young girl is a shemale with big cock
    10.3M views
    Sweet Sissy Shemale Rileydix wants you to cum in her fat ass
    10:28
    Sweet Sissy Shemale Rileydix wants you to cum in her fat ass
    RileyDix
    11.6K views
    shemale dresses sissy to fuck
    16:14
    shemale dresses sissy to fuck
    2M views
    Hijab Asian Trap Sissy Shemale
    07:07
    Hijab Asian Trap Sissy Shemale
    MaureenNadh
    45.9K views
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    29:33
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    Ria_Bentley
    2.4M views
    Horny small cock sissy shemale deep throat and anal fuck
    06:43
    Horny small cock sissy shemale deep throat and anal fuck
    SissySimran
    160.2K views
    Tgirl gets Fucked in Anal while talking to a barmaid
    19:04
    Tgirl gets Fucked in Anal while talking to a barmaid
    MySchoolLife
    639.3K views
    Sissy shemale cosplay, enjoys sucking cocks, playing with vibrator and licking pussies while in chastity and self bondage
    14:26
    Sissy shemale cosplay, enjoys sucking cocks, playing with vibrator and licking pussies while in chastity and self bondage
    Vane03_siss
    3K views
    Sissy CD sucks and is fucked
    08:25
    Sissy CD sucks and is fucked
    1.4M views
    Sissy Shemale Rileydix Front View little Chat and then Twerks to help you CUM!
    12:43
    Sissy Shemale Rileydix Front View little Chat and then Twerks to help you CUM!
    RileyDix
    8.1K views
    My wife told me to play this
    11:13
    My wife told me to play this
    946.8K views
    Sissy Shemale Rileydix Talking Dirty and Playing With Her Sexy Ass
    14:21
    Sissy Shemale Rileydix Talking Dirty and Playing With Her Sexy Ass
    RileyDix
    14.6K views
    SISSY TEST CHECK HOW NAUGHTY SLUT YOU ARE
    07:22
    SISSY TEST CHECK HOW NAUGHTY SLUT YOU ARE
    698.4K views
    Never Expecting to Be a Sexy Girl
    08:12
    Never Expecting to Be a Sexy Girl
    Pure Ts
    447.6K views
    MissRose TS - BEG FOR IT SISSY -  SHEMALE MODEL Domina Fetish ROSE - SHINY pVC OUTFIT - DANCE Seduction pOSE tease
    05:14
    MissRose TS - BEG FOR IT SISSY - SHEMALE MODEL Domina Fetish ROSE - SHINY pVC OUTFIT - DANCE Seduction pOSE tease
    MissRose TS
    11.7K views
    Sissy #3: Feminize Yourself
    16:07
    Sissy #3: Feminize Yourself
    646.6K views
    Desi sissy shemale wearing saree and strip tease
    08:37
    Desi sissy shemale wearing saree and strip tease
    SissySimran
    149.3K views
    Sissy Summer House Dreams 3
    16:29
    Sissy Summer House Dreams 3
    296.8K views
    The most beautiful cumshot i have ever recorded of myself, i am a ladyboy, sissy, shemale and crossdresser model
    03:08
    The most beautiful cumshot i have ever recorded of myself, i am a ladyboy, sissy, shemale and crossdresser model
    Crossdresserkitty
    28.4K views
    family fun 1.mp4
    13:05
    family fun 1.mp4
    1.7M views
    Sissy Shemale Cock Trainer
    06:31
    Sissy Shemale Cock Trainer
    916.5K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Shemale

    • Feminization Male to Crossdresser
    • Sissy Is Becoming a Shemale
    • Feminized and Fucked
    • First Time Crossdressing
    • Shemales Sissification
    • Secret Sissyboy
    • Transvestites Sissies
    • Tranny Femboy
    • Feminine Boys
    • Crossdressers Fucking
    • Feminized
    • Men Dressed as Women
    • Sissyslut
    • Feminize Yourself
    • Femboy Fuck Femboy
    • Beautiful Passable Crossdressers
    • Sissys Get Blacked
    • Crossdreser Sex
    • Become Shemale
    • Femdom Crossdress

    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