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

    Sissy Time Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Time
    First Time Sissy
    Sissy First Time Anal
    Sissy Crossdresser First Time Anal
    Sissy Sucking Cock for First Time
    Sissy Take Dildo First Time Video
    First Time Pegging for Virgin Sissy
    Sissy Crossdresser
    Sissy Training
    Sissy Feminization
    First Time
    Sissy BBC
    Sissy Chastity
    Sissy Husband
    Sissy Compilation
    Sissy Fucked
    Amateur Sissy
    Sissy Blowjob
    Sissy Gangbang
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Guy loses bet turns into sissy CD giving blowjob
      04:52
      Guy loses bet turns into sissy CD giving blowjob
      1.3M views
    • Kassie in sissy time.
      05:28
      Kassie in sissy time.
      98.7K views
    • Sissy identity
      08:50
      Sissy identity
      599.8K views
    • Sissy Time on BBC!
      01:15
      Sissy Time on BBC!
      Phluff2
      24.5K views
    • Never Expecting to Be a Sexy Girl
      08:12
      Never Expecting to Be a Sexy Girl
      Pure Ts
      512.6K views
    • Sissy time!
      00:32
      Sissy time!
      Sissy clitty 123
      553 views
    • Submission Sissy Trainer
      03:23
      Submission Sissy Trainer
      1.2M views
    • Bring Us Holes, Silkbone. or We'll Fuck Yours!
      08:12
      Bring Us Holes, Silkbone. or We'll Fuck Yours!
      Mistress Jodie May
      172.4K views
    • Sissy cum dump compilation
      28:49
      Sissy cum dump compilation
      2.7M views
    • teen trans
      25:13
      teen trans
      World Trany
      180.3K views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.3M views
    • Femboy Tries His First BBC
      03:36
      Femboy Tries His First BBC
      mothplayboy
      80.7K views
    • A guide to sissication: Beginner - Am I a sissy?
      23:32
      A guide to sissication: Beginner - Am I a sissy?
      781.1K views
    • Skinning her ass with big cock
      01:32:24
      Skinning her ass with big cock
      MundoAmador_
      114.3K views
    • How to Train Your Sissy Boyfriend
      08:12
      How to Train Your Sissy Boyfriend
      Brat Perversions
      135.7K views
    • Naughty college girl anal sex
      44:26
      Naughty college girl anal sex
      MundoAmador_
      209.8K views
    • Trust The Fucking Process
      52:41
      Trust The Fucking Process
      1M views
    • Sissy 6
      19:29
      Sissy 6
      1.4M views
    • Sissy #2: Becoming A Cock Slut
      15:35
      Sissy #2: Becoming A Cock Slut
      889.7K views
    • Rented Out by His Mistress
      06:12
      Rented Out by His Mistress
      Pure Ts
      98.4K views
    • Feminization Positivity Trainer
      03:20
      Feminization Positivity Trainer
      723.5K views
    • Sissy Slut Motel
      58:39
      Sissy Slut Motel
      749.4K views
    • Sissy Mind Alteration Video!
      04:45
      Sissy Mind Alteration Video!
      417K views
    • Turned into a good girl and used for his pleasure
      08:12
      Turned into a good girl and used for his pleasure
      Pure Ts
      149.9K views
    • Sissy Dreams 3
      26:07
      Sissy Dreams 3
      1.2M views
    • 3 anal orgasm and hot creampie for skinny trans whore
      16:52
      3 anal orgasm and hot creampie for skinny trans whore
      ActorFab
      2.1M views
    • Emasculate your mind
      13:52
      Emasculate your mind
      500.8K views
    • Turned Into A Cock Loving Sissy
      18:35
      Turned Into A Cock Loving Sissy
      831.2K views
    • Sissyfication
      43:09
      Sissyfication
      1.1M views
    • CD TRAP SISSY EDUCATION TRAINING 101
      01:27:33
      CD TRAP SISSY EDUCATION TRAINING 101
      960.8K views
    • Sissy #3: Feminize Yourself
      16:07
      Sissy #3: Feminize Yourself
      675.1K views
    • Submit to Daddy sissy trainer
      05:26
      Submit to Daddy sissy trainer
      441.5K views
    • Sissy CD sucks and is fucked
      08:25
      Sissy CD sucks and is fucked
      1.5M views
    • Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
      18:27
      Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
      Vane03_siss
      260.6K views
    • Loser Boyfriend Gets Feminized and Fucked
      08:12
      Loser Boyfriend Gets Feminized and Fucked
      Pure Ts
      316.9K views
    • Sissy Feminization
      07:42
      Sissy Feminization
      435.9K views
    • dominant stepmom helps out her sissy slave
      05:59
      dominant stepmom helps out her sissy slave
      Pure Ts
      403.8K views
    • How to train your sissy ass
      17:41
      How to train your sissy ass
      679.2K views
    • Sissy cums too early and gets punished with rough fucking
      02:35
      Sissy cums too early and gets punished with rough fucking
      2.2M views
    • Crossdressing superstar visits the site
      06:40
      Crossdressing superstar visits the site
      Pure Ts
      99.7K views
    • shemale dresses sissy to fuck
      16:14
      shemale dresses sissy to fuck
      2.1M views
    • Sissy Boy3
      33:27
      Sissy Boy3
      1.9M views
    • Tv is for Sissies (Full Video)
      56:35
      Tv is for Sissies (Full Video)
      639.5K views
    • Sauna sissy slut got deepthroated and anal fucking like a good sex slave for BDSM
      39:24
      Sauna sissy slut got deepthroated and anal fucking like a good sex slave for BDSM
      alinanightsky
      185.2K views
    • I turned my straight roommate intro trans wife
      05:20
      I turned my straight roommate intro trans wife
      CutePinkUnicorn
      577.7K views
    • My step sister turned me into her trans wife
      05:13
      My step sister turned me into her trans wife
      CutePinkUnicorn
      128.4K views
    • Sissy Acceptance
      03:53
      Sissy Acceptance
      108.2K 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 Time

    • Dirty Talking Sissy
    • Sissypink Boy
    • Crossdresser Pink Panties
    • Secret Sissyboy
    • The Sissy's Future
    • Femboy Transgirl Dom and Sub
    • Sissyslut Harley
    • Submissive 039 Chastity
    • Beautiful Trans Girl XXX
    • Transvestites Sissies
    • Crossdressers 80
    • Sissie
    • Male to Female Transformation Fantasy
    • Black Tranny Raw
    • Sissychristine
    • Trap Loves Cum
    • Vintage Shemale Bondage 1970 1980
    • Wife Turns Husband Into a Woman
    • Sissy-Slut-Jenny
    • Sissynikky
    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