PornPorn Transgender • US
    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
    WINTER MAGIC SALE ❄️☃️ Snowy discounts, hot deals!
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • Shemale Fucks Girl
    • Sissy
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Cum In Mouth
    • Big Black Cock
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Chastity Peg Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Chastity Fuck
    Chastity Cum
    Trap Pegging
    Pegging Threesome
    Mistress Pegging
    Chastity Sex
    Pegging Orgasm
    Crossdresser Chastity
    Pegging Femdom
    Ladyboy Chastity
    Pegging JOI
    Pegging Cartoon
    Cuckold Pegging
    Chastity Compilation
    Chastity Anal
    Anal Chastity
    Chastity BBC
    Bbc Chastity
    Latex Pegging
    Pegging Humiliation
    Best Videos
    By clicking the content you will also see an ad. AD
    How I've made my boyfriend into a anal slut
    04:39
    How I've made my boyfriend into a anal slut
    Trinit Noir
    61.2K views
    Total Sissy Amnesia
    13:20
    Total Sissy Amnesia
    Natalie Napoli
    28.1K views
    Asian Sissy Chastity Anal Cumshot
    07:41
    Asian Sissy Chastity Anal Cumshot
    CuteAsianSissy
    71.8K views
    Cute tranny in chastity playing with big dildos and anal fisting and fisting
    04:20
    Cute tranny in chastity playing with big dildos and anal fisting and fisting
    Trinit Noir
    23.3K views
    The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)
    07:20
    The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)
    Sonechka25
    36.1K views
    Sissy Chastity Maid Service Training With Ria Bentley
    07:07
    Sissy Chastity Maid Service Training With Ria Bentley
    Ria_Bentley
    40.6K views
    Sissy Merve Rose Chastity Bdsm Fucked DoggyStyle New Body Stockings Sexy Blonde Femboy Tgirl trans Tranny Anal Cum BBC Big Black
    05:10
    Sissy Merve Rose Chastity Bdsm Fucked DoggyStyle New Body Stockings Sexy Blonde Femboy Tgirl trans Tranny Anal Cum BBC Big Black
    TSMerve
    29K views
    Sissys in chastity
    03:40
    Sissys in chastity
    773.4K views
    2 Sissies 1 Chastity Cage
    01:09
    2 Sissies 1 Chastity Cage
    Sissy Joyce
    269.3K views
    sissy clitty chastity
    07:26
    sissy clitty chastity
    527.2K views
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    01:19
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    Princesszoey
    79.2K views
    Beautiful Sissy in chastity enjoys being fucked
    09:38
    Beautiful Sissy in chastity enjoys being fucked
    745K views
    AB094 Lustful teacher extreme trained -Milking 65cm dildo  (Chinese and English subtitles)
    03:52
    AB094 Lustful teacher extreme trained -Milking 65cm dildo (Chinese and English subtitles)
    Abby Kitty
    382.2K views
    mistress makes sissy fuck in chastity
    02:41
    mistress makes sissy fuck in chastity
    502.5K views
    Maskedloki BBC breed trans sissies (Compilation)
    10:06
    Maskedloki BBC breed trans sissies (Compilation)
    Maskedloki9
    378.9K views
    Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor
    05:03
    Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor
    alinanightsky
    409.7K views
    Catgirl rides a dick, fists and cums
    08:03
    Catgirl rides a dick, fists and cums
    Starlightfemboy
    448.1K views
    Sissy Girl getting fucked by BBC Daddy
    02:10
    Sissy Girl getting fucked by BBC Daddy
    Ericka Sprinkle
    17.1K views
    Tranny in chastity fucking her ass with dildos
    03:42
    Tranny in chastity fucking her ass with dildos
    Trinit Noir
    73.6K 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

    Relevant Short videos

    Memorable moment from "Chastity sub gets double anal penetration from big cock TGirl and strap-on MILF"
    Memorable moment from "Chastity sub gets double anal penetration from big cock TGirl and strap-on MILF"
    Spike Essex
    1.3K views
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 9
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 9
    Bailey Wilde
    1.1K views
    My Sissy Cums Again From the Huge BBC Oh, This Feels Amazing! I Hope You Can Do This Yourself?
    My Sissy Cums Again From the Huge BBC Oh, This Feels Amazing! I Hope You Can Do This Yourself?
    FrinaXXX
    115 views
    cumming like crazy
    cumming like crazy
    boobyb0y
    252.6K views
    Hardcore negative chastity
    Hardcore negative chastity
    boobyb0y
    266.1K views
    Locked in chastity
    Locked in chastity
    Sissypropertyuk2
    122.9K views
    Urethral Tube Stimulation with Chastity Cage
    07:00
    Urethral Tube Stimulation with Chastity Cage
    Reina Hanno
    45.1K views
    Sissy Cuckold Fed Creampie And Cum Foot Worship - Jessica Bloom ft Polieana
    05:11
    Sissy Cuckold Fed Creampie And Cum Foot Worship - Jessica Bloom ft Polieana
    Jessica Bloom
    278.4K views
    Piss Pump Evolution 05: The Fem Dom Station
    01:10
    Piss Pump Evolution 05: The Fem Dom Station
    Twistedrama
    119.1K views
    Cute tranny fucked in tiny chastity bareback
    02:11
    Cute tranny fucked in tiny chastity bareback
    Trinit Noir
    41.6K views
    Story of when daddy pimped me out. First week. Anal toy.
    08:50
    Story of when daddy pimped me out. First week. Anal toy.
    Sunaxfemiknulla
    19.3K views
    Submissive femboy is feminized and fucked
    08:30
    Submissive femboy is feminized and fucked
    Crystal Phoenix
    299.7K views
    So Strongly Fucked That I Was Wet Myself
    02:44
    So Strongly Fucked That I Was Wet Myself
    XiangYan
    81.9K views
    Dominant big cock TGirl Lucy bareback fucking her chastity sub
    18:54
    Dominant big cock TGirl Lucy bareback fucking her chastity sub
    Spike Essex
    191.3K views
    Sissy Bride in Chastity
    05:48
    Sissy Bride in Chastity
    Pure Ts
    15.8K views
    BBC Daemon Loki Breeds Femboy Trap Nun in Chastity
    03:25
    BBC Daemon Loki Breeds Femboy Trap Nun in Chastity
    Maskedloki9
    578.2K views
    Fucking Mtf Chastity Charlie 2
    08:12
    Fucking Mtf Chastity Charlie 2
    Jason With Women - Masculine Jason
    28K views
    Super sexy sissy crossdresser in chastity fucked in park
    11:06
    Super sexy sissy crossdresser in chastity fucked in park
    443.8K 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
    Standing Squirt
    02:43
    Standing Squirt
    XiangYan
    76.5K views
    The Bride has a Cock!
    09:06
    The Bride has a Cock!
    Tranny Bizarre
    196K views
    Sissy in chastity fucked by different people
    01:41
    Sissy in chastity fucked by different people
    Sissy Joyce
    530.5K views
    Transgender sissy joyce in chastity shows hormone progress
    05:16
    Transgender sissy joyce in chastity shows hormone progress
    Sissy Joyce
    86.3K views
    No Escaping Bondage - Sissy Maid Punishment - Steel Rigid Ankle-Wrist Spreader
    04:44
    No Escaping Bondage - Sissy Maid Punishment - Steel Rigid Ankle-Wrist Spreader
    Derek6699
    268.7K views
    Asian Sissy Mastubate in Chastity and Cum
    07:12
    Asian Sissy Mastubate in Chastity and Cum
    CuteAsianSissy
    80.5K views
    Best Caged Only orgasms compilation
    06:42
    Best Caged Only orgasms compilation
    boobyb0y
    115K views
    sam_cdsissy sissy crossdresser cums on cam
    24:49
    sam_cdsissy sissy crossdresser cums on cam
    S Sam_cdsissy
    17.9K views
    2 sexy slutty sissies and 1 BBC
    03:32
    2 sexy slutty sissies and 1 BBC
    Ericka Sprinkle
    174.4K views
    Surprise blindfold fuck with two tranny hotties
    10:03
    Surprise blindfold fuck with two tranny hotties
    Tranny Bizarre
    302.3K views
    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
    168.5K views
    Fucking my CAGED little tranny toy and CUMMING on her ass
    03:59
    Fucking my CAGED little tranny toy and CUMMING on her ass
    Freya Frostnymph
    112.1K views
    real sissy full in chastity
    13:34
    real sissy full in chastity
    637.2K views
    sissy shemale chastity poppertrainer
    18:18
    sissy shemale chastity poppertrainer
    212.2K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Chastity Peg

    • Anal Domination Stockings
    • Extreme Rubber
    • Hole Training
    • Latex Bondage Hood
    • Cd-Slut-Leana
    • Shemale Sasha
    • Cuckold Eunuch
    • Bound Sluts
    • Cd-Betina
    • Cd-Fun
    • Transgender Mistress
    • Silicone Vagina Panties
    • Hooded June
    • Holestrech
    • She Wrecks His Ass
    • Strapless Strap on
    • Lunara Kitten Leaked
    • Urethra Torture
    • Early Hormone Treatment Results
    • Shecock Compilation

    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