PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels

    Chicago Milf Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Osha - Big Booty Busty Chicago Belizian Tranny Sucks
      02:17
      Osha - Big Booty Busty Chicago Belizian Tranny Sucks
      107.4K views
    • Osha - Big Booty Busty Chicago Belizian Tranny Fucked
      02:35
      Osha - Big Booty Busty Chicago Belizian Tranny Fucked
      108.5K views
    • Osha Big Booty Busty Chicago Belizian Tranny Fucked Behind
      00:41
      Osha Big Booty Busty Chicago Belizian Tranny Fucked Behind
      149K views
    • Osha - Big Booty Busty Chicago Belizian Tranny Mutual Stroke
      02:23
      Osha - Big Booty Busty Chicago Belizian Tranny Mutual Stroke
      48.9K 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
    • Sveta Melen. A monologue from Chicago-01
      09:11
      Sveta Melen. A monologue from Chicago-01
      2.7K views
    • Kinky inPink Sucks Kircedes Chicagos
      00:23
      Kinky inPink Sucks Kircedes Chicagos
      1.5K views
    • Sexgodpicasso Fucks Chicago Tranny Ashleycreamssss Missionary
      11:25
      Sexgodpicasso Fucks Chicago Tranny Ashleycreamssss Missionary
      SexGodPicasso
      246K views
    • Fucks Chicago Tranny
      20:19
      Fucks Chicago Tranny
      SexGodPicasso
      248.5K views
    • SexGodPicasso Fucks Chicago Tranny AshleyCreamssss Bareback Reverse Cowgirl
      11:48
      SexGodPicasso Fucks Chicago Tranny AshleyCreamssss Bareback Reverse Cowgirl
      SexGodPicasso
      1.2M views
    • Sexgodpicasso Destroys Chicago Tranny TS Ashleycreamssss
      23:04
      Sexgodpicasso Destroys Chicago Tranny TS Ashleycreamssss
      SexGodPicasso
      143.2K views
    • 2 Chicago trannies goin at it
      01:58
      2 Chicago trannies goin at it
      1.1M views
    • SexGodPicasso Fucks Chicago Tranny AshleyCreamssss Missionary Dick Down
      07:59
      SexGodPicasso Fucks Chicago Tranny AshleyCreamssss Missionary Dick Down
      SexGodPicasso
      815K 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
    • SexGodPicasso Fucks Chicago Tranny AshleyCreamssss
      09:08
      SexGodPicasso Fucks Chicago Tranny AshleyCreamssss
      SexGodPicasso
      397.7K views
    • Chicago tranny sucking a  mean dick
      01:22
      Chicago tranny sucking a mean dick
      213.7K views
    • BBC fucks a Trans model in Chicago
      08:51
      BBC fucks a Trans model in Chicago
      adventuresofbo
      28.9K 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
    • 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
    • Sexgodpicasso Meets Chicago Tranny TS Ashleycreamssss
      09:28
      Sexgodpicasso Meets Chicago Tranny TS Ashleycreamssss
      SexGodPicasso
      9.3K views
    • SexGodPicasso VonMadeHaNut Fucks Chicago Tranny TsAshleyCreamssss
      09:16
      SexGodPicasso VonMadeHaNut Fucks Chicago Tranny TsAshleyCreamssss
      SexGodPicasso
      411.2K views
    • Chicago baddie sucking big dick
      03:13
      Chicago baddie sucking big dick
      138.7K 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
    • Sexgodpicasso Meets Chicago Tranny Ashley Creams
      08:06
      Sexgodpicasso Meets Chicago Tranny Ashley Creams
      SexGodPicasso
      21.4K views
    • Aj180 Presents:christening Chicago
      05:40
      Aj180 Presents:christening Chicago
      AJ180
      51.9K views
    • Chicago Tranny Ashley Creams Riding Sexgodpicasso Dick
      09:45
      Chicago Tranny Ashley Creams Riding Sexgodpicasso Dick
      SexGodPicasso
      9.3K 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
    • Sexgodpicasso Breeds Chicago Tranny TS Ashleycreamssss Bareback Raw
      09:53
      Sexgodpicasso Breeds Chicago Tranny TS Ashleycreamssss Bareback Raw
      SexGodPicasso
      4.2K views
    • TGIRLS.XXX: Chicago’s Hottest New Girl
      03:12
      TGIRLS.XXX: Chicago’s Hottest New Girl
      Tgirls
      14.9K views
    • Chicago Baddie Getting Banged Out
      03:42
      Chicago Baddie Getting Banged Out
      66K views
    • Osha - Big Booty Busty Chicago Belizian Tranny HOT
      00:45
      Osha - Big Booty Busty Chicago Belizian Tranny HOT
      58.5K views
    • Jorden gets fucked by Chicago BBC Bareback
      04:42
      Jorden gets fucked by Chicago BBC Bareback
      40.3K views
    • Black tranny from Chicago
      06:14
      Black tranny from Chicago
      Transsexual Angel
      42.7K views
    • Fetlife chicago classified hook-up....FINALLY!!
      02:03
      Fetlife chicago classified hook-up....FINALLY!!
      49.1K views
    • My Friend Sabrina and I Fucked the Boss Non-stop and with Great Desire.
      10:09
      My Friend Sabrina and I Fucked the Boss Non-stop and with Great Desire.
      Tsdanisantos1
      955.6K views
    • Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time - Trans Angels
      10:25
      Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time - Trans Angels
      Trans Angels
      9.1M views
    • The Explosive Magaly Vaz Breaks His Ass and Cums in His Mouth
      11:12
      The Explosive Magaly Vaz Breaks His Ass and Cums in His Mouth
      Pinko TGirls
      645.6K 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
    • Two Sexy Shemales Love Anal Fuck
      01:58:19
      Two Sexy Shemales Love Anal Fuck
      Transsexuell and gay club
      651.9K views
    • I Give Lianna Lawson the Anal Fucking Her Tgirl Ass Craves
      08:12
      I Give Lianna Lawson the Anal Fucking Her Tgirl Ass Craves
      TGIRLPLAYHOUSE
      335.4K views
    • He Fucked Me for Over 30 Minutes and I Honestly Wanted Her to Keep Going
      08:12
      He Fucked Me for Over 30 Minutes and I Honestly Wanted Her to Keep Going
      Gray Perrier
      349.2K views
    • Illuxxxtrandy Hot Blonde with Big Ass Fucked Doggy Style by Huge Monster Cock in Public Bathroom - Intense, Dirty Sex with Tight
      02:15
      Illuxxxtrandy Hot Blonde with Big Ass Fucked Doggy Style by Huge Monster Cock in Public Bathroom - Intense, Dirty Sex with Tight
      sinsweethoneyasses
      2.2M views
    • Stacxxxs Presents: Booty Vs Football
      10:08
      Stacxxxs Presents: Booty Vs Football
      StacXXXs
      421.5K views
    • The TS Fucked Deco Tlover's Mouth and Ass Mercilessly. He Had Double Penetration
      08:12
      The TS Fucked Deco Tlover's Mouth and Ass Mercilessly. He Had Double Penetration
      D DecoTlover
      420.9K views
    • My First Flip Fuck with Mtf Giselle Driller
      08:12
      My First Flip Fuck with Mtf Giselle Driller
      Jason With Women - Masculine Jason
      204.1K views
    • Dating a mature crossdresser
      08:12
      Dating a mature crossdresser
      Pure Ts
      247.1K views
    • You Have to See What These Three Trans Women Did with This Hottie After the Party.
      22:24
      You Have to See What These Three Trans Women Did with This Hottie After the Party.
      Tsdanisantos1
      543.7K views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80

    Categories

    American
    4K Porn
    HD Videos
    VR Porn
    Shemale Fucks Guy
    Big Cock
    Black
    Shemale Fucks Shemale
    Amateur
    Sissy
    Shemale Fucks Girl
    Ladyboy
    Guy Fucks Shemale
    Compilation
    Blowjob
    Cum In Mouth
    Big Black Cock
    Big Ass
    Creampie
    Bareback
    Cumshot
    Mature
    Homemade
    Teen
    Masturbation
    Domination
    Anal
    Brazilian
    Solo
    Asian
    Transgender
    BBW
    Mexican
    Cartoon
    Interracial
    Vintage
    Big Tits
    Japanese
    Young
    Small Cock
    Thai
    Gangbang
    Trans Woman
    Lingerie
    Threesome
    Colombian
    Petite
    BDSM
    Public
    Couple
    Rough Sex
    MILF
    POV
    Anal Masturbation
    Dildo
    Cuckold
    Stockings
    Small Tits
    Babysitter
    Trans Man
    Handjob
    Indian
    Outdoor
    Hentai
    FTM
    Chinese
    Fetish
    Group Sex
    Massage
    Bondage
    Pissing
    British
    Double Penetration
    Role Play
    Behind The Scenes
    German
    Anal Toy
    SFW
    All categories
    Monetize your content
    Become a creator
    xHamster
    • About us
    • 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
    Earn money with us
    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    © 2026 xHamster - Free porn videos.
    Desktop 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