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 Hookups Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Hookup
    Sissy Hotel Hookup
    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
    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
    Ria's Home Workout with Caramel God
    28:52
    Ria's Home Workout with Caramel God
    Ria_Bentley
    230.3K 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
    634.4K views
    Sissy CD get creampied by a online hookup
    09:28
    Sissy CD get creampied by a online hookup
    153.5K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    777.1K views
    Skinny White Sissy Devours Giant BBC
    00:31
    Skinny White Sissy Devours Giant BBC
    Ria_Bentley
    64.9K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    Huge BBC Fucks Cute Sissy Transgirl From Grindr Hookup
    03:55
    Huge BBC Fucks Cute Sissy Transgirl From Grindr Hookup
    Ria_Bentley
    344.7K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    1.9M views
    TS Ria Bentley and Kyla Keys Octane Fucking in Hotel
    08:12
    TS Ria Bentley and Kyla Keys Octane Fucking in Hotel
    Ria_Bentley
    97.9K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.1M views
    TGIRLS HOOKUP: Adorable Fuck Doll Gets Used and Destroyed
    02:00
    TGIRLS HOOKUP: Adorable Fuck Doll Gets Used and Destroyed
    Tgirls Hookup
    143K views
    Dating a mature crossdresser
    08:12
    Dating a mature crossdresser
    Pure Ts
    234.8K views
    TGIRLS HOOKUP: Fuck Me Like a Piece of Fucking Meat!
    01:21
    TGIRLS HOOKUP: Fuck Me Like a Piece of Fucking Meat!
    Tgirls Hookup
    133.4K views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.3M views
    TGIRLS HOOKUP: Insatiable Slut Gets Drilled
    01:08
    TGIRLS HOOKUP: Insatiable Slut Gets Drilled
    Tgirls Hookup
    79K views
    Never Expecting to Be a Sexy Girl
    08:12
    Never Expecting to Be a Sexy Girl
    Pure Ts
    466.7K views
    TGIRLS HOOKUP: Waxed, Vaxxed, and Prolapsed
    02:00
    TGIRLS HOOKUP: Waxed, Vaxxed, and Prolapsed
    Tgirls Hookup
    124.7K 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
    Hot TS Mikah Gives LUCKY FAN A Blowjob  Grindr Sissy Hookup
    01:53
    Hot TS Mikah Gives LUCKY FAN A Blowjob Grindr Sissy Hookup
    32K views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    1.9M views
    Petite Allumeuse En Foret. Cumslut P U B L I C
    19:19
    Petite Allumeuse En Foret. Cumslut P U B L I C
    Allmylinks
    40.4K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M views
    TGIRLS HOOKUP: Well Oiled Slut Machine is Desperate For Dick!
    01:59
    TGIRLS HOOKUP: Well Oiled Slut Machine is Desperate For Dick!
    Tgirls Hookup
    25.9K views
    INTIMATE SEXTAPE WITH A GORGEOUS FRENCH TRANS WOMAN WHO FUCKS ME AND GETS FILLED
    11:38
    INTIMATE SEXTAPE WITH A GORGEOUS FRENCH TRANS WOMAN WHO FUCKS ME AND GETS FILLED
    Maxime horns
    142.4K views
    TGIRLS HOOKUP: Rougher, Harder, Nastier: The Return of Pixi Lust!
    01:59
    TGIRLS HOOKUP: Rougher, Harder, Nastier: The Return of Pixi Lust!
    Tgirls Hookup
    40.8K views
    He filled my ass with it, his drips a lot
    07:53
    He filled my ass with it, his drips a lot
    Piou_Sissy
    243.3K views
    DeeDee Out for A Walk in White Boots Hoping to Hookup
    15:27
    DeeDee Out for A Walk in White Boots Hoping to Hookup
    DeeDeeSlut69
    11.3K views
    Blowing a Guy in His Car Till He Cums - Prettyboi2000x
    11:35
    Blowing a Guy in His Car Till He Cums - Prettyboi2000x
    Prettyboi2000x
    92.3K views
    Bareback Hotel Hookup with Sexy Sissy
    00:49
    Bareback Hotel Hookup with Sexy Sissy
    38.4K views
    Sissy Femboy Fucked From Behind
    05:20
    Sissy Femboy Fucked From Behind
    2.7M views
    TOTALLY 80s XXX: Post Aerobics BJ From Tgirl 2 Cum ABRIDGED
    07:27
    TOTALLY 80s XXX: Post Aerobics BJ From Tgirl 2 Cum ABRIDGED
    Adam Castle
    10.3K views
    Shemale Anatomy
    03:06
    Shemale Anatomy
    2.8M views
    Sissy Hookup Old Highschool Friend
    05:52
    Sissy Hookup Old Highschool Friend
    102.8K views
    A Prostitute Offering Herself on the Street
    02:29
    A Prostitute Offering Herself on the Street
    Wesley Fudedor
    332.8K views
    Thick Latina CD Throated and Twerks Her Big Brown Ass for Anon Grindr Hookup
    07:52
    Thick Latina CD Throated and Twerks Her Big Brown Ass for Anon Grindr Hookup
    B Brittney Bounce
    just added
    Many crossdressers fucked scrnrs
    01:09:02
    Many crossdressers fucked scrnrs
    1.4M views
    TGIRLS HOOKUP: Gaped And Disgraced!
    01:59
    TGIRLS HOOKUP: Gaped And Disgraced!
    Tgirls Hookup
    23K views
    Fucking like a little bitch
    15:52
    Fucking like a little bitch
    Piou_Sissy
    121.8K views
    TGIRLS HOOKUP: Goth Whore Next Door Nikki Jaee
    01:21
    TGIRLS HOOKUP: Goth Whore Next Door Nikki Jaee
    Tgirls Hookup
    58.9K views
    I turned my straight roommate intro trans wife
    05:20
    I turned my straight roommate intro trans wife
    CutePinkUnicorn
    493.8K views
    sissy cd hotel hookup
    01:13
    sissy cd hotel hookup
    9.9K views
    dominant stepmom helps out her sissy slave
    05:59
    dominant stepmom helps out her sissy slave
    Pure Ts
    364.9K views
    TS Ria Bentley Gives Sissification Sissy Slut Hookup Training
    08:12
    TS Ria Bentley Gives Sissification Sissy Slut Hookup Training
    Ria_Bentley
    6.9K views
    A guide to sissication: Beginner - Am I a sissy?
    23:32
    A guide to sissication: Beginner - Am I a sissy?
    745.4K views
    A Slut in a Grove (june 29, 2025) Looking for Cocks. French Transvestite Exhibition Vanessabitchx
    16:44
    A Slut in a Grove (june 29, 2025) Looking for Cocks. French Transvestite Exhibition Vanessabitchx
    Allmylinks
    10.5K views
    On My Knees and They Fill My Mouth with Lots of Milk
    14:18
    On My Knees and They Fill My Mouth with Lots of Milk
    Valera Toro
    493.3K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Hookups

    • Fucking a Sissy Femboy
    • Traps Femboys and Sissys
    • Submissive Crossdresser Fucked Hard
    • Secret Sissyboy
    • Trap Sucking Cock
    • Straight Guys Fantasy
    • Sissy-Virgin
    • Grindr Crossdressers
    • Young Ladyboy First Anal
    • Fuck My Ass Please Dirty Talk
    • Daddy Fucking Sissy Femboy
    • Cross Dresser Blowjob
    • Sisy Boy
    • Begging for Creampie
    • Nasty Amateurs
    • Cute Crossdresser Fucked
    • Crossdreser Sex
    • Amateur Pickup
    • Shemale Twink
    • Daddy's Girl

    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