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

    Boyfriend In Chastity 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
    • 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
      225.1K views
    • Sissy in chastity and monster fuck machine
      07:41
      Sissy in chastity and monster fuck machine
      yourprettykate
      38.5K views
    • Hot Sissygasm Cumpilation - 13 Cumshots in a Row! - full video on LayneLovee Manyvids
      01:13
      Hot Sissygasm Cumpilation - 13 Cumshots in a Row! - full video on LayneLovee Manyvids
      Layne Love
      178K views
    • Cumming after a week in chastity
      05:03
      Cumming after a week in chastity
      Kymmy Harper
      282.2K views
    • Bound sissy in chastity gets BBC
      07:46
      Bound sissy in chastity gets BBC
      949.6K views
    • Sissy locked in chastity and fucks her self hard trying to cum.
      06:27
      Sissy locked in chastity and fucks her self hard trying to cum.
      Lexa Styles
      11.6K views
    • Smash cracks open caged beta sissy kristiscageleaks
      17:26
      Smash cracks open caged beta sissy kristiscageleaks
      Kristi-Jo
      49.1K views
    • Slutty maid training feminization Holly Hunt turns you into a sissy maid in chastity!
      07:34
      Slutty maid training feminization Holly Hunt turns you into a sissy maid in chastity!
      Holly unt
      28.6K views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.2M views
    • Anal sex with sissymaid Kitsy in chastity and bunny ears
      08:10
      Anal sex with sissymaid Kitsy in chastity and bunny ears
      Kitsy Meow
      270K views
    • Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage
      10:16
      Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage
      Jessica Bloom
      72.8K views
    • sissy in chastity swallow cum
      19:06
      sissy in chastity swallow cum
      431K views
    • Girl forgot to tell her Tinder date that she’s Trans
      07:22
      Girl forgot to tell her Tinder date that she’s Trans
      JsseMontz
      638.7K views
    • best slut ever anal in chastity device
      42:13
      best slut ever anal in chastity device
      418.5K views
    • Sissy chastity cage hardcore anal playplay
      02:44
      Sissy chastity cage hardcore anal playplay
      Lexi Faith
      122.2K views
    • Femboy Fucks Crossdresser in Chastity Doggystyle
      02:05
      Femboy Fucks Crossdresser in Chastity Doggystyle
      Bailey Wilde
      66.8K views
    • Trans girl is locked up in chastity, but still giving ass - Emily Adaire ts
      10:34
      Trans girl is locked up in chastity, but still giving ass - Emily Adaire ts
      Emily Adaire
      102K views
    • Sissy Bride in Chastity
      05:48
      Sissy Bride in Chastity
      Pure Ts
      6.7K views
    • Sissy clitty leaking in its flat chastity cage from bareback anal pleasure
      09:30
      Sissy clitty leaking in its flat chastity cage from bareback anal pleasure
      Traviezisha
      108.2K views
    • BBC Fucking Machine Makes Sissy Cum Hard in Chastity!
      06:47
      BBC Fucking Machine Makes Sissy Cum Hard in Chastity!
      Jessica Bloom
      5K views
    • Sissy Dressup Party with Sasha De sade Goes wrong
      01:10
      Sissy Dressup Party with Sasha De sade Goes wrong
      Sissy Joyce
      112.5K views
    • POV: Your gothic trans mistress puts you in chastity and makes fun of you, putting handcuffs on you and making you worship her feet.
      07:37
      POV: Your gothic trans mistress puts you in chastity and makes fun of you, putting handcuffs on you and making you worship her feet.
      Vane03_siss
      27.6K views
    • Caged Trans Rachael Belle Takes BBC with Joy
      08:12
      Caged Trans Rachael Belle Takes BBC with Joy
      Trans Roommates
      188.9K views
    • Sissy Maid Spanked and Whipped in Chastity Bondage
      05:25
      Sissy Maid Spanked and Whipped in Chastity Bondage
      Derek6699
      75.7K views
    • Black and White
      02:03
      Black and White
      226.2K views
    • SISSIES IN CHASTITY
      02:34
      SISSIES IN CHASTITY
      220.8K 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
    • Cute Sissygasms in Chastity Cage Anal Cumslut Jessica Bloom
      07:48
      Cute Sissygasms in Chastity Cage Anal Cumslut Jessica Bloom
      Jessica Bloom
      7K views
    • Sissy Hailey Doll gets her holes ruined by BBC😈
      02:05
      Sissy Hailey Doll gets her holes ruined by BBC😈
      Sissy Haileydoll
      666K views
    • POV Trans Femdom, Suck My Dick While in Chastity You Sissy Slut!
      08:04
      POV Trans Femdom, Suck My Dick While in Chastity You Sissy Slut!
      Jessica Bloom
      4K 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
    • Cute femboy in chastity ride my big cock
      08:06
      Cute femboy in chastity ride my big cock
      Saranji
      112.9K views
    • Lovely young girl is a shemale with big cock
      08:11
      Lovely young girl is a shemale with big cock
      10.6M views
    • SissyJoyce in chastity fucks herself
      01:12
      SissyJoyce in chastity fucks herself
      Sissy Joyce
      15.8K 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
    • Sissy in Chastity takes BBC
      08:45
      Sissy in Chastity takes BBC
      79.6K views
    • I turned my straight roommate intro trans wife
      05:20
      I turned my straight roommate intro trans wife
      CutePinkUnicorn
      510.2K views
    • trans sissy slut with blue hair going crazy with big dildos - MercurySissy aka Mercury Montana  riding and training in chastity
      05:38
      trans sissy slut with blue hair going crazy with big dildos - MercurySissy aka Mercury Montana riding and training in chastity
      MercurySissy
      48.5K views
    • Inverted Chastity Off, Itty Bitty Clitty Gets Sounded, Pushed Back in & Locked up Again!
      07:37
      Inverted Chastity Off, Itty Bitty Clitty Gets Sounded, Pushed Back in & Locked up Again!
      MJ
      202.9K views
    • Sissy Lucy gets Pegged in Chastity whilst trying to wash up
      02:06
      Sissy Lucy gets Pegged in Chastity whilst trying to wash up
      Spike Essex
      82.3K views
    • Sissy Joyce - A real life sissy slave
      01:16
      Sissy Joyce - A real life sissy slave
      Sissy Joyce
      691.4K views
    • sissy slut riding like a champ in chastity - MercurySissy trans anal solo
      02:21
      sissy slut riding like a champ in chastity - MercurySissy trans anal solo
      MercurySissy
      67.7K views
    • Dominated by a couple
      01:11
      Dominated by a couple
      195.8K views
    • Sexy TS Kitty Lucia Maya LEAKS CUM in Chastity While FUCKING HER ASS Then Unlocks Cage & CUMS HARD
      19:03
      Sexy TS Kitty Lucia Maya LEAKS CUM in Chastity While FUCKING HER ASS Then Unlocks Cage & CUMS HARD
      Lucia Maya
      58.8K views
    • sissygasm caged Compilation
      03:17
      sissygasm caged Compilation
      boobyb0y
      267.3K views
    • Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm
      13:54
      Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm
      Sissy Candy
      41K 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
      408.1K views
    Previous page
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80

    Searches Related to Boyfriend In Chastity

    • Sissy-Virgin
    • One Girls Many Boys
    • White Femboys Are so Submissive
    • Bbc Sissygasm
    • Bi Cuckold Sissy Husband
    • Transexual Couple Fucking Like Dogs
    • Tranny Boyfriend
    • New Cumpilation Best Handsfree Orgasms
    • Amateur Threesome FFM Homemade Mature
    • Bareback Creampie
    • Ts Mistresses Dominate
    • Young Transsexual Slut
    • Multiple Loads Swallowing
    • Transgender BDSM
    • Ladyboy Cum Compilation
    • 2 Sissies 1 Chastity Cage
    • Crossdresser Housewife Fantasy
    • Lingerie Solo
    • Sissykanisa
    • Intense Faggot Verbal Humiliation Tgirl
    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