PornPorn Transgender • US
  • Straight
  • Gay
  • Transgender
  • Videos
  • Short videos
  • photos
  • Users
    Forgot password
    Sign in with Google
    Sign in with X
    Sign up for free
    Videos
    • Best Videos
    • Short Videos
    • Watch History
    • American
    • Amateur
    • Shemale Fucks Guy
    • Shemale Fucks Girl
    • Big Cock
    • All categories
    Live Sex
    Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • All categories
    Pornstars
    • Pornstars
    • By Countries
    • xHamster Creators
    Creators
    • Top Creators
    • Top Creator Videos
    • Awards 2025
    • All xHamster Creators
    • By Countries
    • Become a Creator
    Channels
    Photos
    • Ladyboy
    • Tranny
    • Big Cock
    • Thai
    • Blowjob
    • All categories
    Faphouse
    Premium Videos
    Dating
    Subscriptions
    • Upload
    Subscriptions Liked Watch History
    Newest Videos Best Videos Short Videos Top Creators Awards 2025
    • American
    • 4K Porn
    • HD Videos
    • VR Porn
    • Amateur
    • Anal
    • Anal Masturbation
    • Anal Toy
    • Asian
    • Babysitter
    • Bareback
    • BBW
    • BDSM
    • Behind The Scenes
    • Big Ass
    • Big Black Cock
    • Big Cock
    • Big Tits
    • Black
    • Blowjob
    • Bondage
    • Brazilian
    • British
    • Cartoon
    • Chinese
    • Colombian
    • Compilation
    • Couple
    • Creampie
    • Cuckold
    • Cum In Mouth
    • Cumshot
    • Dildo
    • Domination
    • Double Penetration
    • English
    • Fetish
    • FTM
    • Gangbang
    • German
    • Group Sex
    • Guy Fucks Shemale
    • Handjob
    • Hentai
    • Homemade
    • Indian
    • Interracial
    • Japanese
    • Ladyboy
    • Lingerie
    • Massage
    • Masturbation
    • Mature
    • Mexican
    • MILF
    • Outdoor
    • Petite
    • Pissing
    • POV
    • Public
    • Role Play
    • Rough Sex
    • SFW
    • Shemale Fucks Girl
    • Shemale Fucks Guy
    • Shemale Fucks Shemale
    • Sissy
    • Small Cock
    • Small Tits
    • Solo
    • Stockings
    • Teen
    • Thai
    • Threesome
    • Trans Man
    • Trans Woman
    • Transgender
    • Vintage
    • All categories

    Sissy Chastity Anal Trans 720p HD Porn Videos

    All HD 4K
    Newest
    Best Videos
    Premium Videos
    Anal Tranny Cams
    By Rating
    • By Rating
    • By Views
    • By Comments
    Date
    • All
    • 1 Day
    • 7 Days
    • 30 Days
    • Year 2026
    • Year 2025
    720p+
    • All
    • 720p+
    • 1080p+
    • 2160p+
    FPS
    • All
    • 30 FPS
    • 60 FPS
    Duration
    • All
    • 0~2 min
    • 2~5 min
    • 5~10 min
    • 10~30 min
    • 30+ min
    • Full Video
    Production
    • All
    • Producers
    • xHamster Creators
    Clear filters
    Anal HD
    Sissy HD
    Sissy Chastity HD
    Anal Masturbation HD
    Anal Toy HD
    Young Anal HD
    Femboy Anal HD
    Young Sissy HD
    Anal Creampies HD
    Shemale Anal HD
    Sissy Feminization HD
    Sissy Crossdresser HD
    Amateur Sissy HD
    Anal Cumshot HD
    Tranny Anal HD
    Sissy Fuck HD
    Crossdresser Anal HD
    Ladyboy Anal HD
    By clicking the content you will also see an ad. AD
    Cute Shemale Fucks and Rides Big Dildo Cums from Anal Sissygasm
    08:19
    Cute Shemale Fucks and Rides Big Dildo Cums from Anal Sissygasm
    Mariana Taylor
    6.1K views
    Sissy Schoolgirl my First time Fucking my Ass with a Sex Machine BBC Dildo
    10:23
    Sissy Schoolgirl my First time Fucking my Ass with a Sex Machine BBC Dildo
    Mariana Taylor
    5.8K views
    A Lazy Sunday with Her Dildo. Camgurl Toy in Asspussy for Live Cam - Made with Clipchamp
    07:58
    A Lazy Sunday with Her Dildo. Camgurl Toy in Asspussy for Live Cam - Made with Clipchamp
    Sunaxfemiknulla
    1.2K views
    Cop Fucks Trans Woman in Chastity
    01:12
    Cop Fucks Trans Woman in Chastity
    Onlyfans
    4K views
    Sissy chastity training with big black dildo
    09:17
    Sissy chastity training with big black dildo
    Onlyfans
    7K views
    Pink Hair Sissy Slut Riding a Big Dildo
    12:18
    Pink Hair Sissy Slut Riding a Big Dildo
    LoLiLights
    4.5K views
    Sissy Anal Play at home
    12:22
    Sissy Anal Play at home
    SissyDaniella
    2.9K views
    Sissy Oksana 2021 rides a huge dildo and gets sissygasm in chastity_ 230518 _cam.2
    04:48
    Sissy Oksana 2021 rides a huge dildo and gets sissygasm in chastity_ 230518 _cam.2
    Oksana2021
    10.8K views
    Sissy Maids Spiked Chastity Cage Self Bondage in New Boots
    18:24
    Sissy Maids Spiked Chastity Cage Self Bondage in New Boots
    Derek6699
    4.7K views
    Sissy Hope Anal Training Teaser
    12:31
    Sissy Hope Anal Training Teaser
    Sissy Hope
    4.8K views
    Sissy in pink lingerie plays with her machine
    14:21
    Sissy in pink lingerie plays with her machine
    Jasmine904x
    564 views
    Sissy Alexas makes ass pussy stretching exercises in chastity 1 of 2
    05:47
    Sissy Alexas makes ass pussy stretching exercises in chastity 1 of 2
    A Alexa-CGN
    5.3K views
    Sissy Compilation 2024
    06:55
    Sissy Compilation 2024
    Ts Lucy Morningstar
    5.4K views
    Sissy Jannifer Masturbate in JK Uniform
    15:46
    Sissy Jannifer Masturbate in JK Uniform
    Sissy Jennifer
    1.3K views
    Sissy Aubrey Cum While Playing With Sex Machine
    12:05
    Sissy Aubrey Cum While Playing With Sex Machine
    Aubrey Nada
    just added
    Ice un the Ass
    08:52
    Ice un the Ass
    Ts Lucy Morningstar
    11.7K views
    We Fuck Lucy
    05:57
    We Fuck Lucy
    Ts Lucy Morningstar
    5.8K views
    Sissy anal table joi
    13:53
    Sissy anal table joi
    SissyDaniella
    8.6K views
    Twin Game
    21:19
    Twin Game
    Ts Lucy Morningstar
    13.7K views
    Sissy Merve Rose Chastity Ride First Double Anal Cum Gangbang Blonde Sexy Baby Stockings Red Blacked High Hells Tattoo Part 3
    05:41
    Sissy Merve Rose Chastity Ride First Double Anal Cum Gangbang Blonde Sexy Baby Stockings Red Blacked High Hells Tattoo Part 3
    TSMerve
    5.9K views
    Chubby Sissy gets fucked by fuck machine and squirts
    06:51
    Chubby Sissy gets fucked by fuck machine and squirts
    Ellie Ego
    1.2K views
    Sissy in black
    01:07
    Sissy in black
    Sissy Marissa
    1.1K views
    Getting fucked on my back by this machine is amazing. Made me clentch up so hard i pushed it up and nearly squirted
    11:03
    Getting fucked on my back by this machine is amazing. Made me clentch up so hard i pushed it up and nearly squirted
    Ellie Ego
    819 views
    Nadalinda- anal training with my biggest toy
    14:16
    Nadalinda- anal training with my biggest toy
    Sunaxfemiknulla
    1.8K views
    Sissygasm Chastity Vibrator Machine Dildo Fucked Pulpyboy69
    07:50
    Sissygasm Chastity Vibrator Machine Dildo Fucked Pulpyboy69
    FapHouse
    420 views
    Sissy Humps Pillow
    08:18
    Sissy Humps Pillow
    Sissy Skylar
    2K views
    Trans Woman in Bondage and Chastity Fucked
    01:14
    Trans Woman in Bondage and Chastity Fucked
    Jake Grand
    2.8K views
    Shemale slut Ass to mouth Training
    07:49
    Shemale slut Ass to mouth Training
    Mariana Taylor
    1.6K views
    Sissy Marissa Plays with Herself
    12:12
    Sissy Marissa Plays with Herself
    Sissy Marissa
    4.3K views
    Sissy Femboy Riding Dildo untill Sissygasm Cum in Chastity
    08:26
    Sissy Femboy Riding Dildo untill Sissygasm Cum in Chastity
    Joanna CD
    3K views
    CD-Session 31.1.25, black heels, red dress, glass plug
    01:39
    CD-Session 31.1.25, black heels, red dress, glass plug
    FapHouse
    1.7K views
    Sissy Strips out of gold dress
    13:34
    Sissy Strips out of gold dress
    Sissy Skylar
    1.9K views
    Sissy Ride on Dildo Cum Twice and Eat This
    03:19
    Sissy Ride on Dildo Cum Twice and Eat This
    FapHouse
    1.2K views
    Sissy Francis Malice Fisted and Very Happy
    07:50
    Sissy Francis Malice Fisted and Very Happy
    FapHouse
    8.8K views
    Sissy riding Dildo in Public on Glas Door
    10:19
    Sissy riding Dildo in Public on Glas Door
    SissyDaniella
    3.8K views
    double time again
    14:25
    double time again
    Jade Sissy
    7.8K views
    I love getting slowly fucked by this machine on my side and back
    05:49
    I love getting slowly fucked by this machine on my side and back
    Ellie Ego
    592 views
    Sissy Marissa is hungry for cock
    06:56
    Sissy Marissa is hungry for cock
    Sissy Marissa
    6.6K views
    Dressed Sissy in Chastity Rides Mr. Hankey’s Seahorse XS
    02:55
    Dressed Sissy in Chastity Rides Mr. Hankey’s Seahorse XS
    15K views
    Femboi Sissyboi Riding Big Dildo in Micro cage Chastity
    02:12
    Femboi Sissyboi Riding Big Dildo in Micro cage Chastity
    Alesissyboi
    4.2K views
    Caged anal fun
    01:26
    Caged anal fun
    boobyb0y
    6.5K views
    Sissy Schoolgirl Ass to Mouth Training
    10:10
    Sissy Schoolgirl Ass to Mouth Training
    Mariana Taylor
    3K views
    Dirty sissy Dominates a Monster Dildo
    09:38
    Dirty sissy Dominates a Monster Dildo
    Ts Lucy Morningstar
    5.2K views
    First Time Rapper Fucks Hot TS in Chastity
    01:41
    First Time Rapper Fucks Hot TS in Chastity
    Onlyfans
    4.8K views
    19yo femboy fingering his tight ass
    05:17
    19yo femboy fingering his tight ass
    3.7K views
    Training my pussy for Daddy
    01:31
    Training my pussy for Daddy
    DaddysGirl
    5.5K views
    PVC Maid Sissy in chastity playing with large red plug
    01:22
    PVC Maid Sissy in chastity playing with large red plug
    TamaraTv
    4.5K views
    Back
    1
    1. 1
    2. ...
    3. 5
    4. 6
    5. 7
    6. 8
    7. 9
    8. 10
    Next

    Categories Related to Sissy Chastity Anal

    • Crossdresser Dildo HD
    • Crossdressing With Step Dad HD
    • Jerk off in Public HD
    • Outdoor Cum HD
    • Peeing Japanese HD
    • Sissy Dirty Talk HD
    • Blowjob Compilations HD
    • Brutal Shemale HD
    • Trans Mom HD
    • Tranny Whore HD

    Searches Related to Sissy Chastity Anal

    • Sissynat
    • 18 Inch Cock
    • Exotic Shemale
    • Caught Crossdressing Wife
    • Naughty at Home
    • Over 60 Granny Solo
    • Classic Rap Full Movie
    • Vintage Transvestite Movies
    • Daddy Femboy
    • Public Dogging
    xHamster
    • Press
    • 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
    Start making money with us
    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    Monetize your content
    Become a creator
    © 2007 - 2026, xHamster.com
    Mobile 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