PornPorn Transgender • US
  • Videos
  • Short videos
  • photos
  • Users
    Forgot password
    Sign in with Google
    Sign in with X
    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
    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
    • Sissy
    • Shemale Fucks Girl
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Big Black Cock
    • Cum In Mouth
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Holland Of Chicago Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Chicago
    Chicago Tranny
    Best of
    Chicago Street
    Holland Femboy
    Black Chicago
    Lots of Precum
    Lots of Cum
    Out of Control
    Prison of Sissy
    Queen of Spades
    Freaks of Nature
    Best of 1542
    In Front of
    Fountains of Cum
    Mouthful of Cum
    Pussy of Man
    Full of Cum
    The Best of
    Best of Shemale
    Best Videos
    By clicking the content you will also see an ad. AD
    Lovely young girl is a shemale with big cock
    08:11
    Lovely young girl is a shemale with big cock
    10.6M views
    Gay Encouragement and Cumdump Fantasies - Worship Holland Of Chicago
    02:41
    Gay Encouragement and Cumdump Fantasies - Worship Holland Of Chicago
    Holland Of Chicago
    215.3K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M views
    Soft Gay Whispers Encouragement by Holland Of Chicago - You Can't Deny Your Love of Cock and Cum From A Trans Domme
    00:59
    Soft Gay Whispers Encouragement by Holland Of Chicago - You Can't Deny Your Love of Cock and Cum From A Trans Domme
    Holland Of Chicago
    59.4K views
    Latin Mature Tranny Predator with Monster Cock Fuck a Slave
    09:21
    Latin Mature Tranny Predator with Monster Cock Fuck a Slave
    8M views
    Worship Holland Of Chicago - Jerk Off To A Hot Lingerie and Leather Goddess and Go Gay For Me
    02:43
    Worship Holland Of Chicago - Jerk Off To A Hot Lingerie and Leather Goddess and Go Gay For Me
    Holland Of Chicago
    133.5K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3.1M views
    Holland Of Chicago Urges You To Worship Cock and Indulge In Your Leather, Lingerie, Pantyhose, and Cum Fetishes
    02:12
    Holland Of Chicago Urges You To Worship Cock and Indulge In Your Leather, Lingerie, Pantyhose, and Cum Fetishes
    Holland Of Chicago
    21.1K 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
    Sexgodpicasso Fucks Chicago Tranny Ashleycreamssss Missionary
    11:25
    Sexgodpicasso Fucks Chicago Tranny Ashleycreamssss Missionary
    SexGodPicasso
    246K 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
    Fucks Chicago Tranny
    20:19
    Fucks Chicago Tranny
    SexGodPicasso
    248.5K views
    JockPussy - Petite trans hottie Joey Michaels cumdumps for hung jocks
    10:10
    JockPussy - Petite trans hottie Joey Michaels cumdumps for hung jocks
    Jock Pussy
    2.1M views
    SexGodPicasso Fucks Chicago Tranny AshleyCreamssss Bareback Reverse Cowgirl
    11:48
    SexGodPicasso Fucks Chicago Tranny AshleyCreamssss Bareback Reverse Cowgirl
    SexGodPicasso
    1.2M views
    He Tears His Cute Trans Roommate's Pantyhose To Bang Her
    10:54
    He Tears His Cute Trans Roommate's Pantyhose To Bang Her
    Devils tgirls
    6.1M views
    Sexgodpicasso Destroys Chicago Tranny TS Ashleycreamssss
    23:04
    Sexgodpicasso Destroys Chicago Tranny TS Ashleycreamssss
    SexGodPicasso
    143.2K views
    This happened to me leaving school
    19:20
    This happened to me leaving school
    ELIZABETH LARA
    4.3M views
    2 Chicago trannies goin at it
    01:58
    2 Chicago trannies goin at it
    1.1M views
    travesti amateur
    04:25
    travesti amateur
    1.7M views
    SexGodPicasso Fucks Chicago Tranny AshleyCreamssss Missionary Dick Down
    07:59
    SexGodPicasso Fucks Chicago Tranny AshleyCreamssss Missionary Dick Down
    SexGodPicasso
    815K views
    My Husband Fucked My Trans Friend and I Watched and Got Horny! Am I a Cuckquean?
    08:12
    My Husband Fucked My Trans Friend and I Watched and Got Horny! Am I a Cuckquean?
    Lady Snow Brasil
    1.9M views
    Sexgodpicasso Fucks Bimbo Chicago Tranny TS Phuccphaame Raw Bareback
    15:47
    Sexgodpicasso Fucks Bimbo Chicago Tranny TS Phuccphaame Raw Bareback
    SexGodPicasso
    57.1K views
    Veronica Leal Surprises Stacy Cruz with Her FUTA Dick and Gets Her Tight Ass Destroyed - FULL SCENE
    12:33
    Veronica Leal Surprises Stacy Cruz with Her FUTA Dick and Gets Her Tight Ass Destroyed - FULL SCENE
    Futanari XXX
    21.5M views
    SexGodPicasso Fucks Chicago Tranny AshleyCreamssss
    09:08
    SexGodPicasso Fucks Chicago Tranny AshleyCreamssss
    SexGodPicasso
    397.7K views
    Beautiful Latine Trans Goddess cums riding ActorFab's big cock
    10:26
    Beautiful Latine Trans Goddess cums riding ActorFab's big cock
    ActorFab
    2.2M views
    Chicago tranny sucking a  mean dick
    01:22
    Chicago tranny sucking a mean dick
    213.7K views
    Most cute sissy trans cumshot a bigload
    05:24
    Most cute sissy trans cumshot a bigload
    Samantha Sissy World
    835.9K views
    BBC fucks a Trans model in Chicago
    08:51
    BBC fucks a Trans model in Chicago
    adventuresofbo
    28.9K views
    Black tgirl with giant tool fucking a white ass fat faggot
    11:38
    Black tgirl with giant tool fucking a white ass fat faggot
    Latina Tranny
    1.6M views
    TGIRLS XXX - Busty Chicago Beauty Has a Massive Cock!
    03:11
    TGIRLS XXX - Busty Chicago Beauty Has a Massive Cock!
    Tgirls
    447.3K views
    Hostel Surprise
    37:09
    Hostel Surprise
    3.1M views
    Sexgodpicasso Meets Chicago Tranny TS Ashleycreamssss
    09:28
    Sexgodpicasso Meets Chicago Tranny TS Ashleycreamssss
    SexGodPicasso
    9.3K views
    PANSEXUALX Big Dick Erica Cherry Bangs Out 2 College Cuties
    15:08
    PANSEXUALX Big Dick Erica Cherry Bangs Out 2 College Cuties
    PansexualX
    6.6M views
    SexGodPicasso VonMadeHaNut Fucks Chicago Tranny TsAshleyCreamssss
    09:16
    SexGodPicasso VonMadeHaNut Fucks Chicago Tranny TsAshleyCreamssss
    SexGodPicasso
    411.2K views
    Picking up a Sexy Tgirl off the Streets and Giving Her My BBC
    08:12
    Picking up a Sexy Tgirl off the Streets and Giving Her My BBC
    TGIRLPLAYHOUSE
    2.3M views
    Chicago baddie sucking big dick
    03:13
    Chicago baddie sucking big dick
    138.7K views
    I had a big cumshot in unkown hotel
    05:39
    I had a big cumshot in unkown hotel
    Samantha Sissy World
    1.6M views
    Osha - Big Booty Busty Chicago Belizian Tranny Sucks
    02:17
    Osha - Big Booty Busty Chicago Belizian Tranny Sucks
    107.4K views
    The Pizza Boy
    03:38
    The Pizza Boy
    Ftm
    8.3M views
    Osha - Big Booty Busty Chicago Belizian Tranny Fucked
    02:35
    Osha - Big Booty Busty Chicago Belizian Tranny Fucked
    108.5K views
    Trans Hotties Smash Sexy Hunk Soldier - GenderXFilms
    15:07
    Trans Hotties Smash Sexy Hunk Soldier - GenderXFilms
    GenderX
    2.8M views
    young chicago ts nuts in a guys mouth
    01:06
    young chicago ts nuts in a guys mouth
    157.1K views
    I have sex with my ex-boyfriend's transsexual crush
    09:25
    I have sex with my ex-boyfriend's transsexual crush
    NaughtyTrans
    4.3M views
    Aj180 Presents:christening Chicago
    05:40
    Aj180 Presents:christening Chicago
    AJ180
    51.9K 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
    2.1M views
    Sexgodpicasso Meets Chicago Tranny Ashley Creams
    08:06
    Sexgodpicasso Meets Chicago Tranny Ashley Creams
    SexGodPicasso
    21.4K views
    T-Girl cock surprise at the office Chanel Santini
    35:03
    T-Girl cock surprise at the office Chanel Santini
    Shemale World
    878.9K views
    • Back
    • 1
    • 2
    • 3
    • Next

    Searches Related to Holland Of Chicago

    • Big Dick Shemale Homemade
    • 12 Inch Cock
    • First Time Sex Very Hard
    • Please Don T Fuck Me
    • Japanese Cum in Mouth
    • School 18 Brazzers 18 XXX
    • Fucked Deep
    • Vietnamese Ladyboy
    • Filipino Lady Boy
    • Uncontrollable Intense Shaking Orgasm
    • Beautiful Cute
    • Extremely Large Penis
    • Hot 40 Plus
    • 1 Girl on 5 Boys
    • Losing My Virginity to a TS
    • Extreme Dilation Anal and Pee Hole
    • Saudi Arabia Xnxx
    • Japan Family Story
    • Bigger Than Husband
    • Ladyboys Shemales Cumming With Help
    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