PornPorn Transgender • US
  • 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
    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
    • Sissy
    • Shemale Fucks Girl
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Cum In Mouth
    • Big Black Cock
    • Big Ass
    • Bareback
    • Creampie
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Crossdresser Chastity Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Crossdresser
    Chastity
    Crossdresser in Chastity
    Hot Crossdresser Cums Chastity
    Sissy Crossdresser Locked Chastity
    Crossdresser Plugged Chastity Outdoors
    Sissy Crossdresser Anal Fucking Chastity
    Sissy Crossdresser
    Amateur Crossdresser
    Mature Crossdresser
    Crossdresser Fucked
    Sissy Chastity
    Crossdresser Blowjob
    Japanese Crossdresser
    Crossdresser Sex
    Old Crossdresser
    Crossdresser Gangbang
    Cd Crossdresser
    Crossdresser Lingerie
    Crossdresser BBC
    Best Videos
    By clicking the content you will also see an ad. AD
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.6M views
    Sexy Crossdresser Chastity Dildo Orgasm
    08:01
    Sexy Crossdresser Chastity Dildo Orgasm
    80.3K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    1.9M views
    Hot Blonde Crossdresser Chastity Bailey Wilde Photoshoot
    00:45
    Hot Blonde Crossdresser Chastity Bailey Wilde Photoshoot
    Bailey Wilde
    2K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.2M views
    Crossdresser chastity slave outdoor
    06:32
    Crossdresser chastity slave outdoor
    SissySimran
    4.6K 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
    222.4K views
    japanese crossdresser Chastity belt bdsm
    01:23
    japanese crossdresser Chastity belt bdsm
    RayAyanashi
    3.1K views
    Sissy Sex Slave
    07:00
    Sissy Sex Slave
    Kapri Sun
    51.6K views
    Sissy Slut Sucks Cock For Huge Load of Cum Twice in a Row - Jessica Bloom
    08:41
    Sissy Slut Sucks Cock For Huge Load of Cum Twice in a Row - Jessica Bloom
    Jessica Bloom
    46.7K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    798.4K views
    Video editing session turns into a kinky bi and trans foursome orgy
    40:50
    Video editing session turns into a kinky bi and trans foursome orgy
    Spike Essex
    1.2M views
    Sissy Joyce - A real life sissy slave
    01:16
    Sissy Joyce - A real life sissy slave
    Sissy Joyce
    691.4K views
    POV: You are fucking me!!
    07:02
    POV: You are fucking me!!
    Sexy Luke
    31.8K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3.1M views
    Total Sissy Amnesia
    13:20
    Total Sissy Amnesia
    Natalie Napoli
    28.1K views
    Daddy loves to wreck my asshole in chastity
    06:24
    Daddy loves to wreck my asshole in chastity
    missangell_
    479.4K 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
    Lola Sissification 2 Part 1 - G018
    07:29
    Lola Sissification 2 Part 1 - G018
    Lola Femme
    709.1K views
    Asian Sissy Chastity Anal Cumshot
    07:41
    Asian Sissy Chastity Anal Cumshot
    CuteAsianSissy
    71.8K views

    Relevant Short videos

    cumming like crazy
    cumming like crazy
    boobyb0y
    252.6K views
    Hardcore negative chastity
    Hardcore negative chastity
    boobyb0y
    266.1K views
    Squirting like a bitch
    Squirting like a bitch
    boobyb0y
    155.5K views
    Soft limp dick fastest cum ever
    Soft limp dick fastest cum ever
    boobyb0y
    37.1K views
    just showing off my clit
    just showing off my clit
    Jade Sissy
    44.4K views
    removing negative chastity
    removing negative chastity
    boobyb0y
    20.6K views
    Degraded and bound Alina learns that her pleasure is on the secon place during exhausting bdsm session
    11:20
    Degraded and bound Alina learns that her pleasure is on the secon place during exhausting bdsm session
    alinanightsky
    308.2K views
    Sissy Chastity Maid Service Training With Ria Bentley
    07:07
    Sissy Chastity Maid Service Training With Ria Bentley
    Ria_Bentley
    40.6K views
    BBC Fucks a Slutty Crossdresser Without Limits
    32:44
    BBC Fucks a Slutty Crossdresser Without Limits
    Trans and Co
    384.7K 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
    37.4K views
    Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot
    05:27
    Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot
    ActorFab
    236.1K 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
    Leanne Summers
    04:40
    Leanne Summers
    Leanne summers
    40.7K 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
    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
    Catgirl rides a dick, fists and cums
    08:03
    Catgirl rides a dick, fists and cums
    Starlightfemboy
    448.1K views
    Caught in the electric penis cage and piss me on my seam stockings with boots
    10:00
    Caught in the electric penis cage and piss me on my seam stockings with boots
    Loreleyadd
    138.9K 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
    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
    Submissive femboy is feminized and fucked
    08:30
    Submissive femboy is feminized and fucked
    Crystal Phoenix
    299.7K views
    Sissy chastity cage hardcore anal playplay
    02:44
    Sissy chastity cage hardcore anal playplay
    Lexi Faith
    122.2K 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
    I turned my straight roommate intro trans wife
    05:20
    I turned my straight roommate intro trans wife
    CutePinkUnicorn
    510.2K views
    Super sexy sissy crossdresser in chastity fucked in park
    11:06
    Super sexy sissy crossdresser in chastity fucked in park
    443.8K views
    I can't believe i'm posting this! BBC Fucks Sissy
    00:50
    I can't believe i'm posting this! BBC Fucks Sissy
    Sissy Joyce
    443.3K views
    Standing Squirt
    02:43
    Standing Squirt
    XiangYan
    76.5K views
    Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
    01:17
    Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
    Allmylinks
    109.8K views
    sam_cdsissy sissy crossdresser cums on cam
    24:49
    sam_cdsissy sissy crossdresser cums on cam
    S Sam_cdsissy
    17.9K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M views
    Granny tranny Holly riding a BBC dildo and cums in her chastity cage
    03:22
    Granny tranny Holly riding a BBC dildo and cums in her chastity cage
    Hollycd1
    86.8K views
    Tgirl Riley offers her little ass in the hallway
    20:16
    Tgirl Riley offers her little ass in the hallway
    Tgirl Riley
    98.4K views
    chastity cum and squirt and cum again
    05:09
    chastity cum and squirt and cum again
    Juahlovely
    44.7K views
    Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
    44:10
    Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
    alinanightsky
    234.8K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Crossdresser Chastity

    • Sissy Chastity Fucked
    • Femdom With Crossdresser
    • Crossdressing Husband Wear Lingerie
    • Caged Sissies
    • Crossdressers in Pretty Dresses
    • Submissive Femboy
    • Shemale Sissygasm
    • Secret Sissyboy
    • Feminization BDSM
    • Sissy Chastity
    • Cocks Under Skirt
    • Cumming When Tied up
    • Permanent Sissification
    • Maximum Perversum Extrem Pervers
    • Mistress Cuckolding Slave
    • Crossdress Bondage
    • Sissykanisa
    • Bareback Creampie Gangbang
    • Young Transsexual Slut
    • Extreme Rough Sex Brutal Hardcore

    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