PornPorn Transgender • US
  • Videos
  • photos
  • Users
    Forgot password
    google
    Sign in with Google
    Sign in with Twitter
    Sign up for free
    Videos
    • Best Videos
    • Moments
    • Watch History
    • American
    • Amateur
    • Shemale Fucks Guy
    • Shemale Fucks Girl
    • Big Cock
    • All categories
    Live Sex
    Categories
    • Shemale Fucks Guy
    • Black
    • Big Cock
    • Amateur
    • Shemale Fucks Shemale
    • All categories
    Pornstars
    • Pornstars
    • By Countries
    • xHamster Creators
    Creators
    • Top Creators
    • Top Creator Videos
    • Awards 2024
    • All xHamster Creators
    • By Countries
    • Become a Creator
    Channels
    Photos
    • Ladyboy
    • Tranny
    • Big Cock
    • Thai
    • Blowjob
    • All categories
    Faphouse
    Premium Videos
    Dating
    Free VPN
    Free VPN
    Sex Game
    Sex Game
    AI Friend
    AI Friend
    Subscriptions
    • Upload
    CELEBRATE PRIDE MONTH 🏳️‍⚧️ Unlock Your Savings Now!
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Black
    • Big Cock
    • Amateur
    • Shemale Fucks Shemale
    • Sissy
    • Shemale Fucks Girl
    • Compilation
    • Blowjob
    • Bareback
    • Guy Fucks Shemale
    • Ladyboy
    • Big Ass
    • Mature
    • Big Black Cock
    • Cum In Mouth
    • Creampie
    • Cumshot
    • Teen
    • Anal
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Hot Crossdresser Cums Chastity Porn Videos

    Free Porn Videos
    Paid Videos
    Photos
    Chastity
    Hot
    Crossdresser
    Cum
    Hot Crossdresser Sucking and Swallowing Cum
    Hot Crossdresser With Big Boobs Tits Masturbation Cum
    Crossdresser Chastity
    Crossdresser in Chastity
    Sissy Crossdresser Anal Fucking Chastity
    Sissy Crossdresser Locked Chastity
    Chastity Cum
    Chastity Cum Compilation
    Chastity Cage Cum
    Chastity Mistress Sissy Allowed Cum
    Cum in Chastity
    Sissy Chastity Cum
    Sissy Chastity Swallow Cum
    Cum in Chastity Cage
    Shemale Chastity Cum
    Sissy Chastity Cum Compilation
    Best Videos
    By clicking the content you will also see an ad.
    More Trans Chat with xHamsterLive trans now!
    chastity sissy slut vibrator cum
    08:16
    chastity sissy slut vibrator cum
    Juahlovely
    91.6K views
    Hot crossdresser cums in chastity
    00:43
    Hot crossdresser cums in chastity
    42.2K views
    Lola Sissification 2 Part 1 - G018
    07:29
    Lola Sissification 2 Part 1 - G018
    LolaCD
    489.5K views
    Dominatrix Fucks Hot Crossdresser in Chastity
    08:50
    Dominatrix Fucks Hot Crossdresser in Chastity
    Bailey Wilde
    76.9K views
    Sissy chastity cage hardcore anal playplay
    02:44
    Sissy chastity cage hardcore anal playplay
    Lexi Faith
    69.3K views
    I fuck my roommate and fills my butthole full of cum while i'm in chastity
    05:45
    I fuck my roommate and fills my butthole full of cum while i'm in chastity
    missangell_
    150.8K views
    Cum Dripping Out of Me While He Makes Me Cum
    08:12
    Cum Dripping Out of Me While He Makes Me Cum
    Josie Blade
    535K 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
    149.2K 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
    70.1K views
    BBC Fucks a Slutty Crossdresser Without Limits
    32:44
    BBC Fucks a Slutty Crossdresser Without Limits
    parisjango
    14K 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
    100.3K views
    Step-Mom's Secret Surrender 🖤
    16:10
    Step-Mom's Secret Surrender 🖤
    Nancy Rose
    23.5K 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
    99.7K views
    Sissy Slut Strap on Fucked By Femdom Mistress - Jessica Bloom & Polieana Pegging
    07:28
    Sissy Slut Strap on Fucked By Femdom Mistress - Jessica Bloom & Polieana Pegging
    Jessica Bloom
    3K views
    Sissy Maid Testing Buttplugs and Outfits
    08:19
    Sissy Maid Testing Buttplugs and Outfits
    Sissy Joyce
    63.1K views
    Sissy Guide - How to Anal Orgasm in Chastity Cage - Jessica Bloom
    06:14
    Sissy Guide - How to Anal Orgasm in Chastity Cage - Jessica Bloom
    Jessica Bloom
    69.6K views
    Amateur bottom CD Jennifer tag teamed
    03:53
    Amateur bottom CD Jennifer tag teamed
    170.6K views
    Hot Blonde Sissy Bailey Wilde in Chastity Fucked Missionary
    07:15
    Hot Blonde Sissy Bailey Wilde in Chastity Fucked Missionary
    Bailey Wilde
    14.7K 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
    348.5K views
    Chastity Sissy Anal Training Jessica Bloom Anal Instructions
    08:23
    Chastity Sissy Anal Training Jessica Bloom Anal Instructions
    Jessica Bloom
    27.5K 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
    76.5K views
    20 Inches Deep! Sissy Maid Extreme Deep Anal Training Jessica Bloom
    09:08
    20 Inches Deep! Sissy Maid Extreme Deep Anal Training Jessica Bloom
    Jessica Bloom
    4.6K views
    chastity locked sissy squirting on a dildo while thinking about her daddy
    12:23
    chastity locked sissy squirting on a dildo while thinking about her daddy
    Juahlovely
    70.3K views
    Fucking Machine Sissy Anal Orgasm And Cum Play
    09:05
    Fucking Machine Sissy Anal Orgasm And Cum Play
    Jessica Bloom
    4.4K views
    Sissy Candy's Dildo Post Compilation!
    09:24
    Sissy Candy's Dildo Post Compilation!
    Sissy Candy
    34K views
    fucking machine squirt
    21:48
    fucking machine squirt
    Juahlovely
    47.3K views
    Ride Dildo with Thorns
    04:09
    Ride Dildo with Thorns
    XiangYan
    65.7K views
    Dominatrix Makes Hot Blonde Sissy Wear Chastity and Get Fucked
    04:17
    Dominatrix Makes Hot Blonde Sissy Wear Chastity and Get Fucked
    Bailey Wilde
    37.2K views
    Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom
    08:11
    Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom
    Jessica Bloom
    83.7K views
    Sissy taniax cum in the streets
    06:17
    Sissy taniax cum in the streets
    Taniaxtorres
    4K views
    A dress, heels and a chastity cage. Trying a huge dildo and cumming in my tights!
    03:09
    A dress, heels and a chastity cage. Trying a huge dildo and cumming in my tights!
    Starlightfemboy
    290.1K views
    Chastity Sissy Slut Anal Training Dice Game Jessica Bloom
    10:06
    Chastity Sissy Slut Anal Training Dice Game Jessica Bloom
    Jessica Bloom
    2.7K views
    Hot sexy Mistress pegging trans sissy joyce
    01:18
    Hot sexy Mistress pegging trans sissy joyce
    Sissy Joyce
    406.9K views
    Sissy Foot Slave Trampled in High Heel Then Licks Up Cum Jessica Bloom & Polieana
    05:21
    Sissy Foot Slave Trampled in High Heel Then Licks Up Cum Jessica Bloom & Polieana
    Jessica Bloom
    34.2K views
    Moaning femboy  fucked with creampie cum deep inside
    11:43
    Moaning femboy fucked with creampie cum deep inside
    Rozebella
    303.3K views
    Tgirl in Sexy outfit takes off chastity cage, jerks off and finish with a Self Facial
    07:21
    Tgirl in Sexy outfit takes off chastity cage, jerks off and finish with a Self Facial
    Mariana Taylor
    2K views
    Fucked again
    06:09
    Fucked again
    Johanne95
    62.4K views
    Jessica Bloom Riding Monster Dildos Multiple Anal Orgasms in Chastity
    10:15
    Jessica Bloom Riding Monster Dildos Multiple Anal Orgasms in Chastity
    Jessica Bloom
    168.1K views
    2 Sissies 1 Chastity Cage
    01:09
    2 Sissies 1 Chastity Cage
    Sissy Joyce
    152.3K views
    Femboy Fucks Crossdresser in Chastity Doggystyle
    02:05
    Femboy Fucks Crossdresser in Chastity Doggystyle
    Bailey Wilde
    51.8K views
    Cute sissy chastity cage try on - 6 different cages for you FULL VID on LayneLovee Manyvids
    01:39
    Cute sissy chastity cage try on - 6 different cages for you FULL VID on LayneLovee Manyvids
    Layne Love
    43.9K views
    Coral's sissygasm and cum unload
    02:31
    Coral's sissygasm and cum unload
    Coral Blue
    134.4K views
    Sissy Hailey Doll gets her holes ruined by BBC😈
    02:05
    Sissy Hailey Doll gets her holes ruined by BBC😈
    Sissy Haileydoll
    499.5K views
    Sexy Blonde Sissy Bailey Wilde in Chastity Fucked
    10:05
    Sexy Blonde Sissy Bailey Wilde in Chastity Fucked
    Bailey Wilde
    55K views
    Anal sex with sissymaid Kitsy in chastity and bunny ears
    08:10
    Anal sex with sissymaid Kitsy in chastity and bunny ears
    Kitsy Meow
    224.4K views
    Anal Slut Jessica Bloom Rides 11 Inch Qutoys Didlo Balls Deep - Chastity Sissygasm Cumswallow
    05:47
    Anal Slut Jessica Bloom Rides 11 Inch Qutoys Didlo Balls Deep - Chastity Sissygasm Cumswallow
    Jessica Bloom
    11.7K views
    Jessica Bloom Plapping - Ball Busting Chastity Orgasm Sissy Cumslut
    07:27
    Jessica Bloom Plapping - Ball Busting Chastity Orgasm Sissy Cumslut
    Jessica Bloom
    14K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Hot Crossdresser Cums Chastity

    • Beautiful Crossdresser Showing off
    • Caught Crossdressing and Fucked
    • Sissy Forced to Cum
    • Crossdressers Kirsty in an Orgy
    • Fuck Me Like a Whore
    • Beautiful Crossdresser Rubbing Cock
    • Sissy Bondage Dominated and Fucked
    • Colombian Crossdresser Sucks and Fucks
    • Two Crossdressers Cum Kisses
    • First Time Crossdressing for Friend
    • Sissy Crossdresser First Time Anal
    • Shemale Fucks Virgin Boy
    • Sissy Dominated by Master and Mistress
    • Crossdresser Hard Fuck
    • Shemale Fucks Guy in Chastity
    • Cums on Her Own Face
    • First Time With My Transvestite Friend
    • Femboy Lesbian Sex
    • Lesbian Sex With a Trans Woman
    • Femboy Sissy Gets Fucked Public Restroom
    Chat with xHamsterLive trans now! More Trans

    xHamster

    • xHamster Shop
    • Press
    • Blog
    • Creator's Blog
    • Advertising
    • xHamster NFT
    • xHamster Awards 2024

    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 - 2025, xHamster.com
    Mobile Version
    18 U.S.C. 2257 Record-Keeping Requirements Compliance Statement
    RTA Restricted To AdultsRTA Restricted To Adults