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
    Dating
    Subscriptions
    • Upload
    WINTER MAGIC SALE ❄️☃️ Snowy discounts, hot deals!
    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
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Stretched Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Sissy Gets Stretched to the Max
    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
    Sissy Femdom
    Sissy Boy
    Sissy Slut
    Best Videos
    By clicking the content you will also see an ad. AD
    Butt Girl Anal Asmr Anal Satisfaction of Tiffany Ciskiss
    21:20
    Butt Girl Anal Asmr Anal Satisfaction of Tiffany Ciskiss
    Tiffany Ciskiss
    8.4K views
    Anal Destruction for Human Ashtray Loren Aprile
    02:22
    Anal Destruction for Human Ashtray Loren Aprile
    Loren Aprile
    120.2K views
    Sexy Shemale Secretary Opens Her Big Ass in the Bathroom of a Gas Station
    07:19
    Sexy Shemale Secretary Opens Her Big Ass in the Bathroom of a Gas Station
    fermerino
    9K views
    Pool Girl Lina lost tons of Balls in her Ass and pushes them out
    01:20
    Pool Girl Lina lost tons of Balls in her Ass and pushes them out
    Lina Free
    22.7K views
    German Femboy HUGE ANAL GAPE and FIRST PROLAPSE
    05:08
    German Femboy HUGE ANAL GAPE and FIRST PROLAPSE
    typischjayy
    31.7K views
    Spinning dildo on fucking machine
    01:15
    Spinning dildo on fucking machine
    AmandaKnight
    22.2K views
    Jasmine Dlight & Hannah Blake & Miss Lolalu - Double Dom Anal Fuckslut Destruction - DP Strapons and Double Fisting
    08:11
    Jasmine Dlight & Hannah Blake & Miss Lolalu - Double Dom Anal Fuckslut Destruction - DP Strapons and Double Fisting
    Jasmine_dlight
    31.1K views
    Extreme Anal Fisting From Valentina Rosa Part 2, Taking It Deeper
    00:31
    Extreme Anal Fisting From Valentina Rosa Part 2, Taking It Deeper
    Jasmine_dlight
    363.1K views
    Sporty femboy with great ass fucks doggystyle
    03:56
    Sporty femboy with great ass fucks doggystyle
    Kenny White
    127.1K views
    Spandexfemboy - My BBC Dildo Filled Out My Hole
    17:10
    Spandexfemboy - My BBC Dildo Filled Out My Hole
    3.9K views
    cumwhore latex Susan and giant dildo
    12:44
    cumwhore latex Susan and giant dildo
    kinkylatex cd
    28.2K views
    Skinny Ladyboy Anal Casting, Slave Training and Cream Enema
    01:02
    Skinny Ladyboy Anal Casting, Slave Training and Cream Enema
    FilmmakerDiaries
    59.2K views
    Being Both #70-living Fantasies - Intense Cock Worship, Deepthroating and Ass-fucking
    08:12
    Being Both #70-living Fantasies - Intense Cock Worship, Deepthroating and Ass-fucking
    Being Both
    4K views
    Melinda Jamescd in a Fucking Hot Butplug Session Stretching Her Cunt
    05:27
    Melinda Jamescd in a Fucking Hot Butplug Session Stretching Her Cunt
    Melinda James
    31.1K views
    Enema play in the bathroom
    05:07
    Enema play in the bathroom
    Magnum-dildo
    54.3K views
    Adorable Trans Hucow Stuffs Her Ass with a Huge Dildo
    13:32
    Adorable Trans Hucow Stuffs Her Ass with a Huge Dildo
    Melodyfluffington
    39.2K views
    A Slut in a Grove (june 29, 2025) Looking for Sperm. French Transvestite Exhibition Vanessabitchx
    25:22
    A Slut in a Grove (june 29, 2025) Looking for Sperm. French Transvestite Exhibition Vanessabitchx
    Allmylinks
    36.2K views
    Adorable Trans-wife Strips, Milks Her Tits, Plugs Her Ass, and Jerks Until She Cums
    10:38
    Adorable Trans-wife Strips, Milks Her Tits, Plugs Her Ass, and Jerks Until She Cums
    Melodyfluffington
    25.1K views
    fucking machine squirt
    21:48
    fucking machine squirt
    Juahlovely
    95.2K views
    With patience, everything happens! Two big cocks endered my ass together..
    07:24
    With patience, everything happens! Two big cocks endered my ass together..
    covo_sissy_cross
    49.1K views
    Big Girls Playing Big Black Toys
    02:49
    Big Girls Playing Big Black Toys
    Melinda James
    14K views
    Forged3dx Intense Anal Sex Delicious Hot Big Ass Tasty Tight Ass Anus Gaping Cum Dripping
    16:30
    Forged3dx Intense Anal Sex Delicious Hot Big Ass Tasty Tight Ass Anus Gaping Cum Dripping
    Hatanoxxxmiwa
    83.1K views
    Beauties of Anal Delights for the Female Superiority Society (part 2).
    23:53
    Beauties of Anal Delights for the Female Superiority Society (part 2).
    TvTs Isabella Coupe
    80.6K views
    Bang my ass with your fat dick - Chantal needs it hard
    04:26
    Bang my ass with your fat dick - Chantal needs it hard
    Sissy Slut Chantal Sweet
    8.4K views
    gorgeous t-girl Melody strips, oils her body, and plays with her tight hole
    10:55
    gorgeous t-girl Melody strips, oils her body, and plays with her tight hole
    Melodyfluffington
    65.7K views
    Melody Sluts Out with Her Dildos and Plug
    04:16
    Melody Sluts Out with Her Dildos and Plug
    Melodyfluffington
    4.9K views
    trans sissy slut with blue hair going crazy with big dildos - MercurySissy aka Mercury Montana  riding and training in chastity
    05:38
    trans sissy slut with blue hair going crazy with big dildos - MercurySissy aka Mercury Montana riding and training in chastity
    MercurySissy
    48.5K views
    Nuttytouch Intense Anal Sex Hot Pleasure Rough Sex Sweet Tasty Fuck Hot Hard Sex Ass Fuck Gaping Ass
    02:27
    Nuttytouch Intense Anal Sex Hot Pleasure Rough Sex Sweet Tasty Fuck Hot Hard Sex Ass Fuck Gaping Ass
    Hatanoxxxmiwa
    51K 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
    24K views
    Fuck me hard even though I'm small
    05:39
    Fuck me hard even though I'm small
    missangell_
    44.3K views
    Hottest anal moments with Melody's juicy trans bubble butt - Oiled ass - ass to mouth
    05:22
    Hottest anal moments with Melody's juicy trans bubble butt - Oiled ass - ass to mouth
    Melodyfluffington
    94.6K views
    White Sissy Bubble Butt Fucked by Machine and Huge Dildo
    05:55
    White Sissy Bubble Butt Fucked by Machine and Huge Dildo
    NKeyCD
    5.1K views
    Tgirl Riley & TgrilTrainerNL date #8 part I
    25:23
    Tgirl Riley & TgrilTrainerNL date #8 part I
    Tgirl Riley
    28.4K views
    Big Tits Asian American sissy tranny trap cum dump anal doggie bareback with tit fuck and facial
    52:14
    Big Tits Asian American sissy tranny trap cum dump anal doggie bareback with tit fuck and facial
    DaddyandLexa
    63.4K views
    Larissa1sexdoll. Into the black hole.  Mega gape. Double ass piercing.
    10:11
    Larissa1sexdoll. Into the black hole. Mega gape. Double ass piercing.
    Larissa1sexdoll
    248K views
    Full Session of Extreme Anal Destruction
    12:50
    Full Session of Extreme Anal Destruction
    Branquinha Large
    23.2K views
    This dirty ass is just for you Daddy
    06:13
    This dirty ass is just for you Daddy
    missangell_
    48.3K views
    After work guy fucks trans cute girl
    07:26
    After work guy fucks trans cute girl
    LittleVixenSlut
    5.4K views
    Sissy Evolution 2: Be Happy. Be a Bimbo
    06:08
    Sissy Evolution 2: Be Happy. Be a Bimbo
    Tiffany Cox
    4.8K views
    Extreme Anal Creampie Compilation Big Ass Femboy in Cosplay Ass Gaped
    19:59
    Extreme Anal Creampie Compilation Big Ass Femboy in Cosplay Ass Gaped
    fermerino
    31.8K views
    Slutty Fat Ass Melody Sucks, Rides, Gapes and Cums
    10:12
    Slutty Fat Ass Melody Sucks, Rides, Gapes and Cums
    Melodyfluffington
    41K views
    Exhibit P🚗U B L I C en Pute on a Parking Lot in the Forest, at La Faisanderie 91. Fanciful Tights, Thong [4sep25] Meet CoKiiNE! VaneSsaBiTCHx
    29:23
    Exhibit P🚗U B L I C en Pute on a Parking Lot in the Forest, at La Faisanderie 91. Fanciful Tights, Thong [4sep25] Meet CoKiiNE! VaneSsaBiTCHx
    Allmylinks
    36.2K views
    Sissy bf give me a hot blowjob
    07:58
    Sissy bf give me a hot blowjob
    Rozebell
    46.3K views
    Melody Stuffs Her Slutty Hole with Giant Anal Beads - Cumshot - Anal Destruction
    14:35
    Melody Stuffs Her Slutty Hole with Giant Anal Beads - Cumshot - Anal Destruction
    Melodyfluffington
    8.3K views
    Moaning Trans-Femboy Slut gets hole pounded hard by thick cock - prettyboi2000x
    15:22
    Moaning Trans-Femboy Slut gets hole pounded hard by thick cock - prettyboi2000x
    Prettyboi2000x
    4.6K views
    gaping my ass
    09:45
    gaping my ass
    i iacute
    28K views
    Beautiful Little Trans-Slut gets fucked in the ass and cum all over her - prettyboi2000x
    18:12
    Beautiful Little Trans-Slut gets fucked in the ass and cum all over her - prettyboi2000x
    Prettyboi2000x
    7.3K views
    • Back
    • 1
    • ...
    • 5
    • 6
    • 7
    • 8
    • 9
    • ...
    • 80
    • Next

    Searches Related to Sissy Stretched

    • Transvestite Fucking Transvestite
    • Skinny Hardcore
    • Limp Sissygasm
    • Femboys and Sissys
    • Kinky Kora
    • Girly Erectus Sm 379
    • Not Gay
    • Pimped
    • Stepbro Analed His Horny TS Stepsister
    • Slow Penetration
    • Bent Over
    • Slutty Slave
    • Bendochy
    • Shemale Flopping
    • Crossdresserlover Ladyboys
    • Cock Stroking Garter Belt
    • Feminine Beauty
    • Giving Him Backshots
    • Sissy-Cori
    • I Love You

    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