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
    -60%
    Dating
    Subscriptions
    • Upload
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday Sale
    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
    • Homemade
    • Mature
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Chastity Orgasm Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Chastity
    Orgasm
    Sissy Chastity
    Chastity Sissy
    Chastity Sissy Having Anal Orgasm
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Compilation
    Sissy Fucked
    Sissy Slave
    Amateur Sissy
    Sissy Blowjob
    Sissy Cuckold
    Sissy Gangbang
    Submissive Sissy
    Best Videos
    By clicking the content you will also see an ad. AD
    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
    174.4K views
    Jessica Bloom Plapping - Ball Busting Chastity Orgasm Sissy Cumslut
    07:27
    Jessica Bloom Plapping - Ball Busting Chastity Orgasm Sissy Cumslut
    Jessica Bloom
    26.1K views
    Best Caged Only orgasms compilation
    06:42
    Best Caged Only orgasms compilation
    boobyb0y
    112.8K views
    F Machine Alpha Fucks Sissy Asshole - Jessica Bloom Chastity Orgasm And Cum In Mouth
    07:23
    F Machine Alpha Fucks Sissy Asshole - Jessica Bloom Chastity Orgasm And Cum In Mouth
    Jessica Bloom
    30.7K views
    handz free shemale cumming while getting fucked
    13:40
    handz free shemale cumming while getting fucked
    2.4M views
    SissyMindy Sissy Anal toying chastity orgasm and cum eating
    05:26
    SissyMindy Sissy Anal toying chastity orgasm and cum eating
    SissyMindy10
    2.1K views
    why do I suddenly love trannys?
    12:46
    why do I suddenly love trannys?
    1.2M views
    Sissy Holly Sph Chastity Orgasm
    03:01
    Sissy Holly Sph Chastity Orgasm
    slinnkee
    1.5K 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
    165.1K views
    Chastity Orgasm
    05:59
    Chastity Orgasm
    4.2K views
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    01:19
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    Princesszoey
    74.9K views
    Webcam humiliation Reginaferguson in chastity orgasm
    01:49
    Webcam humiliation Reginaferguson in chastity orgasm
    1.8K views
    Hands Free Sissy Orgasms Vol 5
    14:52
    Hands Free Sissy Orgasms Vol 5
    406.3K views
    Chastity Orgasm by Sissy Mindy
    16:05
    Chastity Orgasm by Sissy Mindy
    SissyMindy10
    2K 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
    65.1K views
    anal plugged sissy chastity vibrator cum
    10:10
    anal plugged sissy chastity vibrator cum
    Juahlovely
    14.7K views
    Compilation: Trannies Cum While they get Fucked
    13:29
    Compilation: Trannies Cum While they get Fucked
    3.8M views
    Sissy Chastity JOI - Unlock and Ruin your Orgasm with Me
    01:34
    Sissy Chastity JOI - Unlock and Ruin your Orgasm with Me
    Layne Love
    11.6K views
    sissygasm caged Compilation
    03:17
    sissygasm caged Compilation
    boobyb0y
    265.7K views
    Sissy Chastity Sissygasm Drinking - Trans Cumslut Jessica Bloom
    10:11
    Sissy Chastity Sissygasm Drinking - Trans Cumslut Jessica Bloom
    Jessica Bloom
    27.8K views
    Handsfree Sissygasm Compilation Vol. 3
    15:12
    Handsfree Sissygasm Compilation Vol. 3
    551.2K views
    Skyler Storm sissy chastity dildo machine
    04:25
    Skyler Storm sissy chastity dildo machine
    2.2K 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
    29.5K views
    Sissy Chastity Cage Orgasm cuming in my chastity cage
    01:39
    Sissy Chastity Cage Orgasm cuming in my chastity cage
    SissyMindy10
    6.8K views
    Tranny Babe in Chasity Cage Gets Fucked by large Dildo
    11:37
    Tranny Babe in Chasity Cage Gets Fucked by large Dildo
    939.6K views
    How I've made my boyfriend into a anal slut
    04:39
    How I've made my boyfriend into a anal slut
    Trinit Noir
    55K views
    Sissy cums too early and gets punished with rough fucking
    02:35
    Sissy cums too early and gets punished with rough fucking
    2.1M views
    Standing Squirt
    02:43
    Standing Squirt
    XiangYan
    69.5K views
    The Shortest Time! I've Ever Lasted Rubbing My Prostate with a Dildo in My Bare Feet
    02:55
    The Shortest Time! I've Ever Lasted Rubbing My Prostate with a Dildo in My Bare Feet
    XiangYan
    298.2K views
    Tranny Girl PUBLIC with a dominant guy! After facial cumshot she continues walking through the city!
    00:43
    Tranny Girl PUBLIC with a dominant guy! After facial cumshot she continues walking through the city!
    TV_Helena
    586.3K views
    Hands Free Sissy Orgasms Vol 2
    15:20
    Hands Free Sissy Orgasms Vol 2
    311.1K views
    Milky TGirl in Chastity has Handsfree Sissygasm + Shows her Lactating Tits
    01:38
    Milky TGirl in Chastity has Handsfree Sissygasm + Shows her Lactating Tits
    Princesszoey
    87.3K views
    Anal orgasm, Cumming while fucked, Sissygasm
    12:49
    Anal orgasm, Cumming while fucked, Sissygasm
    1.2M views
    TGirl in Chastity with Lactating Tits has Anal Orgasm Hands Free Sissygasm
    01:59
    TGirl in Chastity with Lactating Tits has Anal Orgasm Hands Free Sissygasm
    Princesszoey
    74.3K views
    SissyJoyce Sissygasm
    01:25
    SissyJoyce Sissygasm
    Sissy Joyce
    57.1K views
    Trans Girl Forced Orgasm
    08:12
    Trans Girl Forced Orgasm
    Mistress Jodie May
    105K views
    Mistress Lets Sissy Squirt In Cage
    01:52
    Mistress Lets Sissy Squirt In Cage
    Devotion1986
    11.4K views
    Chastity ass pounded sissy
    03:43
    Chastity ass pounded sissy
    Lockedupunicorn
    55.6K views
    chastity cum and squirt and cum again
    05:09
    chastity cum and squirt and cum again
    Juahlovely
    40.7K views
    Stepdaddies Little Chastity Slut - Fucking Machine Cumshot
    06:54
    Stepdaddies Little Chastity Slut - Fucking Machine Cumshot
    Jessica Bloom
    5K views
    cum handsfree while fucked by bbc
    00:38
    cum handsfree while fucked by bbc
    3M views
    Crazy fetish trannys! Chastity sex with a live rubber doll!
    01:16
    Crazy fetish trannys! Chastity sex with a live rubber doll!
    TV_Helena
    74K views
    fufu clip sissy anal dildo squirt
    05:56
    fufu clip sissy anal dildo squirt
    Juahlovely
    58.7K views
    Locked, Submissive Trans Sissy in Long Machine Play
    13:58
    Locked, Submissive Trans Sissy in Long Machine Play
    Paula Rainbow
    7.3K views
    chastity sissy slut vibrator cum
    08:16
    chastity sissy slut vibrator cum
    Juahlovely
    153.1K views
    Ass to Mouth With Over 100 Loads of CUM! Frozen Cum Play Sissy Jessica Bloom
    10:20
    Ass to Mouth With Over 100 Loads of CUM! Frozen Cum Play Sissy Jessica Bloom
    Jessica Bloom
    15.9K views
    slutty sissygasm compilation
    05:18
    slutty sissygasm compilation
    107.1K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Chastity Orgasm

    • Sissy Prostate Orgasm
    • Chastity Cum
    • Beautiful Shemale Can T Stop Cumming
    • Fainting Orgasms
    • Sissygasm Sex
    • Uncontrollable Intense Shaking Orgasm
    • Caged Anal
    • Cum in Chastity Cage
    • Sissy Cums While Being Fucked
    • Fucking Machine Bondage
    • First Sissygasm
    • Multiple Orgasms
    • Japanese Shemales Uncensored Ejaculation
    • Cums While Getting Fucked
    • So Deep He Came so Much
    • Extreme Milking
    • Handcuffed Crossdresser
    • Trap BDSM
    • Femboy Squirt
    • Cumming When Tied up

    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