PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    LET IT SNOW, LET IT SAVE! ☃️ Faphouse Discounts – Winter Edition

    Crying Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Sissy Crying
    Sissy Crossdresser
    Sissy Training
    Sissy Feminization
    Sissy BBC
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Sissy Blowjob
    Sissy Slave
    Sissy Gangbang
    Amateur Sissy
    Sissy Cuckold
    Sissy Femdom
    Sissy Slut
    Sissy Boy
    Sissy Faggot
    Submissive Sissy
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Sluttiest Sissy CD Cumpilation
      18:35
      Sluttiest Sissy CD Cumpilation
      1.1M views
    • SexGodPicasso Fucks Chicago Tranny AshleyCreamssss Bareback Reverse Cowgirl
      11:48
      SexGodPicasso Fucks Chicago Tranny AshleyCreamssss Bareback Reverse Cowgirl
      SexGodPicasso
      1.2M views
    • I Cum on Morgane Marks' Breasts
      22:32
      I Cum on Morgane Marks' Breasts
      Mamou5891
      194K views
    • Little bitch loves to feel my hot cum inside her dirty pussy
      05:27
      Little bitch loves to feel my hot cum inside her dirty pussy
      MrNastyXavier
      468.4K views
    • She Is a Feminization Academy Graduate
      08:12
      She Is a Feminization Academy Graduate
      Pure Ts
      71.8K views
    • tranny with a fat dick cum compilation
      05:09
      tranny with a fat dick cum compilation
      Sissy_Sasha_Q
      51.6K views
    • My Cock in Her Ass to This Big Femboy Slut
      37:14
      My Cock in Her Ass to This Big Femboy Slut
      Trans and Co
      681.6K views
    • 2 Guys fucking amateur sissy outdoors part 2
      31:00
      2 Guys fucking amateur sissy outdoors part 2
      675.1K views
    • Neighbor Fills Me with Milk
      15:38
      Neighbor Fills Me with Milk
      Valera Toro
      78.6K views
    • classy crossdresser handles the cock with ease
      08:12
      classy crossdresser handles the cock with ease
      Pure Ts
      100.5K views
    • Sucking Her Cum off His Cock and Overflowing Anal Creampies  Compilation
      05:23
      Sucking Her Cum off His Cock and Overflowing Anal Creampies Compilation
      Melodyfluffington
      290.1K views
    • Sexy Shemale Server Gets Extra Cream!! from BBC!
      12:52
      Sexy Shemale Server Gets Extra Cream!! from BBC!
      Big Dick RJxxx
      521.8K views
    • Cum eating instructions hung tgirl eats her own cum to show you how it's done, humiliation feminization JOI
      13:19
      Cum eating instructions hung tgirl eats her own cum to show you how it's done, humiliation feminization JOI
      Holly unt
      80.1K views
    • I fuck a funny sex doll Monica moments
      08:46
      I fuck a funny sex doll Monica moments
      fansly
      275.8K views
    • Slide into Sissy Girlfriend
      02:22
      Slide into Sissy Girlfriend
      1.9M views
    • Daddy loves to wreck my asshole in chastity
      06:24
      Daddy loves to wreck my asshole in chastity
      missangell_
      482.4K views
    • Sissy Lesbians
      07:37
      Sissy Lesbians
      1.3M views
    • Sexy hot naughty Sissy Crossdresser
      10:25
      Sexy hot naughty Sissy Crossdresser
      FapHouse
      732.5K views
    • Sissy Mind Alteration Video!
      04:45
      Sissy Mind Alteration Video!
      399.1K views
    • Tgirl Riley offers her little ass in the hallway
      20:16
      Tgirl Riley offers her little ass in the hallway
      Tgirl Riley
      103.4K views
    • NO LONGER A MAN! SISSY LOVES COCK NOW!
      07:58
      NO LONGER A MAN! SISSY LOVES COCK NOW!
      718.9K views
    • Cross Dressing Student and Tutor Playing with Each Other
      08:12
      Cross Dressing Student and Tutor Playing with Each Other
      Crossdressing Amateurs
      306.6K views
    • Jenny, a Pretty French Trans, Gets Fucked in the Ass by a Big Black Cock
      31:16
      Jenny, a Pretty French Trans, Gets Fucked in the Ass by a Big Black Cock
      FapHouse
      444.6K views
    • Sissy Slut Motel
      58:39
      Sissy Slut Motel
      731.8K views
    • EAT SHEMALE CUM CEI TRAINER
      11:13
      EAT SHEMALE CUM CEI TRAINER
      674.5K views
    • You're Straight Right- - Sissy Hypno Training
      03:07
      You're Straight Right- - Sissy Hypno Training
      926.8K views
    • Gorgeous Alt Trans-girl Suck and Fucks
      12:24
      Gorgeous Alt Trans-girl Suck and Fucks
      Melodyfluffington
      192.7K views
    • German anal tranny date outdoor on holiday in Mallorca
      17:26
      German anal tranny date outdoor on holiday in Mallorca
      EroCom
      466.8K views
    • Trans Slut With Big Ass Gets Fucked By Trans Beauty - prettyboi2000x
      20:30
      Trans Slut With Big Ass Gets Fucked By Trans Beauty - prettyboi2000x
      Prettyboi2000x
      94.4K views
    • Ai Gerou Femboyzinha Linda Masturbating the Ass of a Naughty Girl
      01:25
      Ai Gerou Femboyzinha Linda Masturbating the Ass of a Naughty Girl
      NumbCroft
      72.3K views
    • Turning a straight man into a passive little whore by passionately fucking him with my big cock
      06:15
      Turning a straight man into a passive little whore by passionately fucking him with my big cock
      DotadaSP
      1.4M views
    • Submission Sissy Trainer
      03:23
      Submission Sissy Trainer
      1.2M views
    • Sissy Joyce - A real life sissy slave
      01:16
      Sissy Joyce - A real life sissy slave
      Sissy Joyce
      697.4K views
    • A White Boys Purpose
      23:50
      A White Boys Purpose
      Kimberhaven
      606.4K views
    • Daddy's little sissy slut
      08:34
      Daddy's little sissy slut
      942.6K views
    • Bi Sissy Confusion
      04:42
      Bi Sissy Confusion
      1.2M views
    • mature crossdresser enjoys her big dick alpha
      08:12
      mature crossdresser enjoys her big dick alpha
      Pure Ts
      233.5K views
    • Sissy: A slut documentary
      08:12
      Sissy: A slut documentary
      Brat Perversions
      37.2K views
    • My Moans, My Pulse, My Climax, Better with Headphones
      06:14
      My Moans, My Pulse, My Climax, Better with Headphones
      Lavala
      110.5K views
    • Kinkyist Sissy Compilation
      06:57
      Kinkyist Sissy Compilation
      506.6K views
    • Fuck Us Both Billy
      08:12
      Fuck Us Both Billy
      TSRyley
      97.2K views
    • Mrs Lovings Sissy Training
      10:13
      Mrs Lovings Sissy Training
      2.3M views
    • SISSY TEST CHECK HOW NAUGHTY SLUT YOU ARE
      07:22
      SISSY TEST CHECK HOW NAUGHTY SLUT YOU ARE
      712.4K views
    • Ts Teen Tranny Gets Fucked Raw BareBack By BBC
      22:06
      Ts Teen Tranny Gets Fucked Raw BareBack By BBC
      SexGodPicasso
      1.1M views
    • Feminization Positivity Trainer
      03:20
      Feminization Positivity Trainer
      714.7K views
    • Fucking in all positions
      05:15
      Fucking in all positions
      Celine LAFFITE
      101.9K views
    • The Shortest Time! I've Ever Lasted Rubbing My Prostate with a Dildo in My Bare Feet
      02:55
      The Shortest Time! I've Ever Lasted Rubbing My Prostate with a Dildo in My Bare Feet
      XiangYan
      319.8K views
    Previous page
    Next page
    1
    1. 1
    2. ...
    3. 5
    4. 6
    5. 7
    6. 8
    7. 9
    8. ...
    9. 44
    10. ...
    11. 80
    80

    Searches Related to Crying Sissy

    • Sissymeike
    • Tushy
    • Your-Sissyslut
    • When She Bigger Than You
    • Sissyboy-5
    • Bisexual Slave
    • Funny Accident
    • Blindfolded
    • Punishing
    • Don't Tell
    • Tied up Gangbang
    • Whore
    • Bimbo
    • Sissy_tammy
    • Role Reversal
    • Barely Legal
    • Bratty Sis
    • Cant Hold
    • Bullied
    • Crossdressing Daddies
    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