PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
      -60%
    • Pornstars
    • Channels
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday Sale

    Sissy Milf Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Milf
    Milf Sissy Strapon
    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
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Sissy Milf Rileydix wearing a nighty and shaking her Big Ass
      07:39
      Sissy Milf Rileydix wearing a nighty and shaking her Big Ass
      RileyDix
      308.4K views
    • Sissy MILF Fantasy
      07:06
      Sissy MILF Fantasy
      Pure Ts
      17.8K views
    • Sissy milf feels horny, poses and squirts her cum 🫦
      05:04
      Sissy milf feels horny, poses and squirts her cum 🫦
      Orchidee35
      9.6K views
    • Trans sissy MILF Karolina electro torture
      13:55
      Trans sissy MILF Karolina electro torture
      T Transmilfkarolina
      109.8K views
    • Sissy Milf Rileydix double orgasm riding BBC
      18:09
      Sissy Milf Rileydix double orgasm riding BBC
      RileyDix
      26.3K views
    • Sissy Milf Rileydix is Ready to be Naughty Together!
      20:49
      Sissy Milf Rileydix is Ready to be Naughty Together!
      RileyDix
      28.4K views
    • Sopa enema for sissy MILF slut
      05:54
      Sopa enema for sissy MILF slut
      T Transmilfkarolina
      39.9K views
    • Horny sissy MILF poses and squirts her load
      05:04
      Horny sissy MILF poses and squirts her load
      Orchidee35
      1.4K views
    • Great Ass Sissy MILF Fuicking Her Ass with a Black Massive Dildo
      03:21
      Great Ass Sissy MILF Fuicking Her Ass with a Black Massive Dildo
      JenniferStarTS
      428 views
    • The Tiniest Dick Sissy MILF Destroying Her Ass with a Black Massive Dildo
      03:24
      The Tiniest Dick Sissy MILF Destroying Her Ass with a Black Massive Dildo
      JenniferStarTS
      just added
    • Great Legs and Feet Sissy MILF Fucking Her Ass with Big Toys
      26:24
      Great Legs and Feet Sissy MILF Fucking Her Ass with Big Toys
      JenniferStarTS
      679 views
    • Sissy MILF
      01:05
      Sissy MILF
      Tatiana Zorrita
      3.6K views
    • Sissy MILF Tranny Destroying Her Ass Until Cum Like a Girl
      12:54
      Sissy MILF Tranny Destroying Her Ass Until Cum Like a Girl
      JenniferStarTS
      1.4K views
    • Karolina sissy MILF behind scenes
      13:44
      Karolina sissy MILF behind scenes
      T Transmilfkarolina
      5.8K views
    • Dildo Fucking - Sissy MILF Tranny Big Ass
      06:30
      Dildo Fucking - Sissy MILF Tranny Big Ass
      JenniferStarTS
      2.3K views
    • Best sissy milf stockings hotel video yet
      03:31
      Best sissy milf stockings hotel video yet
      2.5K views
    • Tiny Dick Shemales Sissy MILF
      00:56
      Tiny Dick Shemales Sissy MILF
      JenniferStarTS
      2.1K views
    • Amazing Sissy MILF, Streching Her Ass for Real Cocks - Sissification
      23:26
      Amazing Sissy MILF, Streching Her Ass for Real Cocks - Sissification
      JenniferStarTS
      529 views
    • Sissy MILF
      01:22
      Sissy MILF
      Tatiana Zorrita
      2.6K views
    • facefucking sissy milf with balaclava
      00:26
      facefucking sissy milf with balaclava
      4K views
    • Fuck my ass with many great toy and cum - huge dildos cumshot sissy milf tranny
      12:27
      Fuck my ass with many great toy and cum - huge dildos cumshot sissy milf tranny
      JenniferStarTS
      3.1K views
    • Huge Ass Sissy MILF Training Her Ass with Big Toys
      03:32
      Huge Ass Sissy MILF Training Her Ass with Big Toys
      JenniferStarTS
      846 views
    • Destroying My Sissy Ass off - Big Ass, Sissy, MILF
      02:50
      Destroying My Sissy Ass off - Big Ass, Sissy, MILF
      JenniferStarTS
      819 views
    • Big Ass Sissy MILF Training Her Ass - Sissification
      23:57
      Big Ass Sissy MILF Training Her Ass - Sissification
      JenniferStarTS
      452 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
      480.2K views
    • Dating a mature crossdresser
      08:12
      Dating a mature crossdresser
      Pure Ts
      214.7K views
    • Swallow My Cum
      15:15
      Swallow My Cum
      TSRyley
      240.6K views
    • TGirl Ria Bentley Gets TAKEN RAW By 9 Full Inches BBC POV
      07:05
      TGirl Ria Bentley Gets TAKEN RAW By 9 Full Inches BBC POV
      Ria_Bentley
      294.6K views
    • Bimbo Takes on BBC
      08:34
      Bimbo Takes on BBC
      TSRyley
      116.3K views
    • Submissive Sissy crossdresser fucked by BBC - she is a bitch4
      09:55
      Submissive Sissy crossdresser fucked by BBC - she is a bitch4
      Rozebella
      649.2K views
    • I ended up in this sissy hole. I love fucking and sucking a big dick and showing them what a real blowjob part4
      05:59
      I ended up in this sissy hole. I love fucking and sucking a big dick and showing them what a real blowjob part4
      Rozebella
      141.4K views
    • First Time Anal
      08:41
      First Time Anal
      Pure Ts
      68.2K views
    • Sucking His BBC
      08:55
      Sucking His BBC
      Tsdanisantos1
      238.7K views
    • He Used to Be the Boss but Not Anymore
      08:12
      He Used to Be the Boss but Not Anymore
      Pure Ts
      458.7K views
    • Crossdressing superstar visits the site
      06:40
      Crossdressing superstar visits the site
      Pure Ts
      42.7K views
    • Daddy Milks Trans Girl Prostate
      05:06
      Daddy Milks Trans Girl Prostate
      Gray Perrier
      305.9K views
    • The Bordello Calarel  Shemale Slave Have a Big Cock Big Cock Porn
      09:59
      The Bordello Calarel Shemale Slave Have a Big Cock Big Cock Porn
      PissOnAsshole
      157.4K views
    • Sexy Red Bone Tranny Fuck Guy In His Tight Ass
      07:29
      Sexy Red Bone Tranny Fuck Guy In His Tight Ass
      simon pole
      43.8K views
    • Loving up his secret crossdresser babe
      08:12
      Loving up his secret crossdresser babe
      Pure Ts
      324.8K views
    • Sucking and Jerking Each Other off Until Completion
      06:36
      Sucking and Jerking Each Other off Until Completion
      Crossdressing Amateurs
      251.3K views
    • Argentina Tranny Ts Perla Ate My Nut
      12:34
      Argentina Tranny Ts Perla Ate My Nut
      SexGodPicasso
      1.9M views
    • Sir Maxx Gets Great Service From Hot Housekeeper
      08:56
      Sir Maxx Gets Great Service From Hot Housekeeper
      Sir Maxximus
      145.7K views
    • Imagine You Are Fucking a Boy!
      06:15
      Imagine You Are Fucking a Boy!
      KinkyHome
      58.5K views
    • Tgirl Riley offers her little ass in the hallway
      20:16
      Tgirl Riley offers her little ass in the hallway
      Tgirl Riley
      85.1K views
    • Playtime 69
      27:02
      Playtime 69
      TSRyley
      64.8K views
    • Making My Cock Explode
      08:09
      Making My Cock Explode
      TSRyley
      46.7K views
    • Between the Lines & Between My Legs
      14:17
      Between the Lines & Between My Legs
      Gray Perrier
      84.2K views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80

    Searches Related to Sissy Milf

    • Daddy Fucking Sissy Femboy
    • Milf Crossdresser
    • British Mature Crossdressers
    • Caught Crossdressing by Mom
    • Feminized and Fucked
    • Secret Sissyboy
    • Tranny Slut
    • Femboys in Lingerie
    • Crossboy With Mommy Clothes
    • Transvestites Sissies
    • Homemade Sissy
    • Crossdress Fuck
    • Boy Dressed as Girl
    • Transvestite Secretary
    • Slutty Crossdresser
    • Breeding Cds From the Top Position
    • Crossdressing Daddies
    • Extreme Granny
    • Sexy Mature Trans
    • Femdom Feminization
    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