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

    Chastity Anal Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Chastity
    Anal
    Anal Chastity
    Anal Orgasm Chastity
    Anal Machine Chastity Sissy
    Sissy Crossdresser Anal Fucking Chastity
    Chastity Sissy Having Anal Orgasm
    Sissy Smoking Anal Faggot in Chastity
    Sissy Chastity
    Femboy Anal
    Anal Orgasm
    Sissy Anal
    Anal Creampies
    Crossdresser Anal
    Shemale Anal
    Trans Anal
    Double Anal
    Anal Masturbation
    Anal Sissygasm
    Chastity Cum
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Sissy Accidentally cums while rubbing her clit in the little chastity cage
      01:41
      Sissy Accidentally cums while rubbing her clit in the little chastity cage
      KiraszaSissy
      176.2K views
    • Asian Sissy Chastity Anal Cumshot
      07:41
      Asian Sissy Chastity Anal Cumshot
      CuteAsianSissy
      86.5K 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
      215.9K views
    • Trans Girl Lactating Her Milky Tits While in Chastity + Anal Toying
      02:19
      Trans Girl Lactating Her Milky Tits While in Chastity + Anal Toying
      Princesszoey
      105.5K 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
      93.5K views
    • Sissy Haileydoll In Chastity Anal Training And Gapes
      01:12
      Sissy Haileydoll In Chastity Anal Training And Gapes
      Sissy Haileydoll
      73.1K 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
      113.4K views
    • Trans Mistress Hands Free Chastity Anal Cum
      00:35
      Trans Mistress Hands Free Chastity Anal Cum
      CD Mandi
      3K views
    • Sissy chastity training
      08:23
      Sissy chastity training
      234.3K views
    • Sissy Merve Rose Chastity Anal Plug Double Anal Gangbang Big White Cock Tattoo Catgirl Blonde Baby Sexy Stockings Blacked
      05:15
      Sissy Merve Rose Chastity Anal Plug Double Anal Gangbang Big White Cock Tattoo Catgirl Blonde Baby Sexy Stockings Blacked
      TSMerve
      14.8K views
    • Tranny Babe in Chasity Cage Gets Fucked by large Dildo
      11:37
      Tranny Babe in Chasity Cage Gets Fucked by large Dildo
      982.4K views
    • Femboy Sissy in Chastity, Anal Gape by Fuckmachine Dildo and Pighole Butt Plug
      10:30
      Femboy Sissy in Chastity, Anal Gape by Fuckmachine Dildo and Pighole Butt Plug
      G8pess
      16.5K views
    • fufu clip sissy anal dildo squirt
      05:56
      fufu clip sissy anal dildo squirt
      Juahlovely
      72.2K views
    • Sissy Slut Haileydoll In Chastity Anal Training BBC Dildo
      01:21
      Sissy Slut Haileydoll In Chastity Anal Training BBC Dildo
      Sissy Haileydoll
      59.9K views
    • Chastity Never Ends
      07:57
      Chastity Never Ends
      Ts Lucy Morningstar
      75.6K views
    • Sissy in chastity anal orgasm
      02:43
      Sissy in chastity anal orgasm
      Sissy Paige
      909 views
    • TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
      01:19
      TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
      Princesszoey
      93.8K views
    • sissygasm caged Compilation
      03:17
      sissygasm caged Compilation
      boobyb0y
      276.6K views
    • Negative Cage hardcore Cumload
      02:12
      Negative Cage hardcore Cumload
      boobyb0y
      112.8K views
    • 16" BBC vs Sissy Slut Jessica Bloom Balls Deep
      07:55
      16" BBC vs Sissy Slut Jessica Bloom Balls Deep
      Jessica Bloom
      19.4K views
    • Anal Sissygasms In The Woods Chastity Slut Jessica Bloom
      05:17
      Anal Sissygasms In The Woods Chastity Slut Jessica Bloom
      Jessica Bloom
      39.6K views
    • Relevant Short videos

      Trans Mistress Hands Free Chastity Anal Cum
      Trans Mistress Hands Free Chastity Anal Cum
      CD Mandi
      823 views
      Femboy Sissy in Chastity, Anal Gape by Fuckmachine Dildo and Pighole Butt Plug
      Femboy Sissy in Chastity, Anal Gape by Fuckmachine Dildo and Pighole Butt Plug
      G8pess
      2.3K views
      Asian Sissy Chastity Anal Cumshot
      Asian Sissy Chastity Anal Cumshot
      CuteAsianSissy
      957 views
      cumming like crazy
      cumming like crazy
      boobyb0y
      255.1K views
      Hardcore negative chastity
      Hardcore negative chastity
      boobyb0y
      268.8K views
      Squirting like a bitch
      Squirting like a bitch
      boobyb0y
      156.5K views
    • Bound sissy in chastity gets BBC
      07:46
      Bound sissy in chastity gets BBC
      978.7K views
    • Hot sissy in chastity is fucked by machine
      12:25
      Hot sissy in chastity is fucked by machine
      Jasmine904x
      7.4K views
    • Chasity cage
      03:55
      Chasity cage
      NikkyTrav
      157.5K views
    • sissy clitty chastity
      07:26
      sissy clitty chastity
      540.6K views
    • Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot
      05:27
      Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot
      ActorFab
      271.8K views
    • Sissy in flat chastity cage opening her legs and ass for his male to fuck her bareback
      10:56
      Sissy in flat chastity cage opening her legs and ass for his male to fuck her bareback
      Traviezisha
      140.6K views
    • Shemale Anatomy
      03:06
      Shemale Anatomy
      2.9M views
    • Cute tranny fucked in tiny chastity bareback
      02:11
      Cute tranny fucked in tiny chastity bareback
      Trinit Noir
      52.8K views
    • She Is a Feminization Academy Graduate
      08:12
      She Is a Feminization Academy Graduate
      Pure Ts
      89.9K views
    • Best Caged Only orgasms compilation
      06:42
      Best Caged Only orgasms compilation
      boobyb0y
      124.4K views
    • TGirl Puts on Chastity Cage, Locking Away her Tiny Penis
      01:11
      TGirl Puts on Chastity Cage, Locking Away her Tiny Penis
      Princesszoey
      63K views
    • Chastity Guide : A review of all metal chastity cages!! - By Sissy Joyce
      17:39
      Chastity Guide : A review of all metal chastity cages!! - By Sissy Joyce
      Sissy Joyce
      142.4K views
    • Sissy Training by Queen Daralis Part 3
      03:52
      Sissy Training by Queen Daralis Part 3
      Sissy Joyce
      10.3K views
    • 2 Sissies 1 Chastity Cage
      01:09
      2 Sissies 1 Chastity Cage
      Sissy Joyce
      285.3K views
    • 3 anal orgasm and hot creampie for skinny trans whore
      16:52
      3 anal orgasm and hot creampie for skinny trans whore
      ActorFab
      2.2M views
    • Caged Trans Rachael Belle Takes BBC with Joy
      08:12
      Caged Trans Rachael Belle Takes BBC with Joy
      Trans Roommates
      195.4K views
    • All sissy should be loked in chastity
      03:26
      All sissy should be loked in chastity
      350.4K views
    • How to Put on Flat Chastity Cage Guide (Jessica Bloom)
      06:08
      How to Put on Flat Chastity Cage Guide (Jessica Bloom)
      Jessica Bloom
      37.4K views
    • Paula Rainbow takes her first spin on a fucking machine
      07:06
      Paula Rainbow takes her first spin on a fucking machine
      Paula Rainbow
      19.6K views
    • Tranny with chastity cage fucked deep
      02:28
      Tranny with chastity cage fucked deep
      LittleVixenSlut
      27.3K views
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.7M 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
      190.5K views
    • TGirl Lucy in Chastity is fucked by 10 inch BBC at SheWorld
      12:24
      TGirl Lucy in Chastity is fucked by 10 inch BBC at SheWorld
      Spike Essex
      465.9K views
    • Down the Sissy Rabbit Hole - My Story
      00:44
      Down the Sissy Rabbit Hole - My Story
      Sissy Joyce
      22.8K views
    • chastity sissy slut vibrator cum
      08:16
      chastity sissy slut vibrator cum
      Juahlovely
      166K views
    • Urethral Tube Stimulation with Chastity Cage
      07:00
      Urethral Tube Stimulation with Chastity Cage
      Reina Hanno
      55.9K 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 Chastity Anal

    Anal Orgasm Chastity
    Sissy Cum in Cage
    Chastity Orgasm
    Caged Anal
    Sissy Dildo Training
    Chastity Pee
    Fucking Machine Bondage Anal
    Hands Free Sissygasm
    Transvestite Spanking Maid
    Ass Trainer
    Trans Prostate Orgasm
    Submissive Wife
    Sissy Sex Slave Anime
    Hentai Shemale
    Chastity Fuck
    Outdoor Humiliation
    Bimbo Cum
    Cuckold Humiliation
    Chasity Cage
    Feminization Cartoon
    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