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
    ICE MELTING SALE — 50% OFF 🧊🔥 Limited-time deal
    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
    • Big Black Cock
    • Cum In Mouth
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Maid Anal Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Anal
    Maid
    Sissy Maid
    Anal Sissy
    Maid Sissy
    Sissy Crossdresser
    Sissy Training
    Sissy Feminization
    Sissy BBC
    Sissy Chastity
    Sissy Husband
    Sissy Compilation
    Sissy Fucked
    Sissy Blowjob
    Amateur Sissy
    Sissy Gangbang
    Sissy Cuckold
    Sissy Boy
    Sissy Femdom
    Best Videos
    By clicking the content you will also see an ad. AD
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    FapHouse
    2.2M views
    Sissy maid - anal play pt1
    02:42
    Sissy maid - anal play pt1
    FapHouse
    636 views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    2M views
    Sissy Maid Anal Training
    01:05
    Sissy Maid Anal Training
    SubmissiveFetish
    6K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.5M views
    Sissy Slut Maid - Anal Toys
    13:57
    Sissy Slut Maid - Anal Toys
    Alinatgirl
    814 views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    2M views
    Sissy maid services
    10:20
    Sissy maid services
    1.4M views
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    29:33
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    FapHouse
    2.6M views
    Daddy fucks his sissy maid
    10:01
    Daddy fucks his sissy maid
    127.1K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.7M views
    Sissy Maid Gets Locked in Bondage and Chastity to Be Fucked by Her Sex Doll
    23:36
    Sissy Maid Gets Locked in Bondage and Chastity to Be Fucked by Her Sex Doll
    FapHouse
    34.7K views
    Rented Out by His Mistress
    06:12
    Rented Out by His Mistress
    Pure Ts
    81.8K views
    Sissy Maid Is so Sensual and Sexy
    07:42
    Sissy Maid Is so Sensual and Sexy
    Pure Ts
    8.9K views
    Sissy cums too early and gets punished with rough fucking
    02:35
    Sissy cums too early and gets punished with rough fucking
    2.2M views
    Sissy Maid Struggling in new Armbinder and Steel Chastity Belt with 7" Dildo Locked inside
    10:50
    Sissy Maid Struggling in new Armbinder and Steel Chastity Belt with 7" Dildo Locked inside
    Derek6699
    66.3K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    851.2K views
    Sissy Maid Is Not Done with Her Chores
    08:26
    Sissy Maid Is Not Done with Her Chores
    Pure Ts
    40.1K views
    Daddy's Good Girl!
    08:12
    Daddy's Good Girl!
    Pure Ts
    970.7K views
    sissy maid cleans up your cock
    08:43
    sissy maid cleans up your cock
    Pure Ts
    14.5K views
    Shemale Anatomy
    03:06
    Shemale Anatomy
    2.9M views
    Sissy Maid Testing Buttplugs and Outfits
    08:19
    Sissy Maid Testing Buttplugs and Outfits
    FapHouse
    96.3K views
    Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    304.6K views
    Sissy Maid Is Taught Proper Manners
    06:12
    Sissy Maid Is Taught Proper Manners
    Pure Ts
    7.8K views
    Daddy Milks Trans Girl Prostate
    05:06
    Daddy Milks Trans Girl Prostate
    Gray Perrier
    360.7K views
    Sissy maid Lilith gets out of trouble with a guest
    08:12
    Sissy maid Lilith gets out of trouble with a guest
    Pure Ts
    30K views
    Teen Sissy Already Knows Her Place
    08:12
    Teen Sissy Already Knows Her Place
    Pure Ts
    76.2K views
    Transformed into Sissy Maid to Get Job
    12:49
    Transformed into Sissy Maid to Get Job
    Bailey Wilde
    155.1K views
    You Are Just a Hole - Variety Itsol
    10:46
    You Are Just a Hole - Variety Itsol
    Rodrigo Amor
    1.9M views
    Sissy Maid Service Practicing on a Dildo at Her Fake Glory Hole
    18:20
    Sissy Maid Service Practicing on a Dildo at Her Fake Glory Hole
    FapHouse
    23.3K views
    Turned into a good girl and used for his pleasure
    08:12
    Turned into a good girl and used for his pleasure
    Pure Ts
    142K views
    Sissy Maid Pegged for Job
    05:22
    Sissy Maid Pegged for Job
    Bailey Wilde
    83.5K views
    CD TRAP SISSY EDUCATION TRAINING 101
    01:27:33
    CD TRAP SISSY EDUCATION TRAINING 101
    944.3K views
    Sissy Maid Self Bondage Electro Punishment
    36:35
    Sissy Maid Self Bondage Electro Punishment
    Derek6699
    104.5K views
    2 Mommies Training Their TS Slut - Lucy Hart - Penny Barber - Mira Maven
    15:07
    2 Mommies Training Their TS Slut - Lucy Hart - Penny Barber - Mira Maven
    Lucy Hart
    403.7K views
    Sissy Maid Has the Best Boipussy
    08:12
    Sissy Maid Has the Best Boipussy
    Pure Ts
    37.3K views
    Sissy Joyce - A real life sissy slave
    01:16
    Sissy Joyce - A real life sissy slave
    FapHouse
    703.4K views
    Isabella Sissy Maid Diarys
    19:57
    Isabella Sissy Maid Diarys
    181.3K views
    mistress cages sissy
    12:29
    mistress cages sissy
    955.7K views
    Stunning Sissy Maid Looks so Feminine and Sexy
    08:12
    Stunning Sissy Maid Looks so Feminine and Sexy
    Pure Ts
    22.4K views
    How to Train Your Sissy Boyfriend
    08:12
    How to Train Your Sissy Boyfriend
    Brat Perversions
    124.5K views
    Sissy Maid Is Taught Proper Manners
    06:12
    Sissy Maid Is Taught Proper Manners
    Pure Ts
    3.1K views
    Lovely young girl is a shemale with big cock
    08:11
    Lovely young girl is a shemale with big cock
    10.8M views
    Do you need a Sissy Maid? I clean the house and something else - Veronica Sanders
    05:45
    Do you need a Sissy Maid? I clean the house and something else - Veronica Sanders
    Onlyfans
    58.8K views
    Completely Submitted and Feminized
    08:12
    Completely Submitted and Feminized
    Pure Ts
    53.8K views
    Fed My Own Cum Strapped to Fucking Machine Chair in Chastity - Sissy Maid
    14:36
    Fed My Own Cum Strapped to Fucking Machine Chair in Chastity - Sissy Maid
    Derek6699
    74.7K views
    Bound sissy in chastity gets BBC
    07:46
    Bound sissy in chastity gets BBC
    959K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Maid Anal

    • Beautiful Sissy Anal
    • Fuck My Ass Please Dirty Talk
    • Femboy Gangbang
    • Fucked Like a Girl
    • Secret Sissyboy
    • Extreme Rough Sex Brutal Hardcore
    • Sissypink Boy
    • Traps Femboys and Sissys
    • Ladyboy Butt
    • Trap Pounded
    • Maid Spanking
    • Uncensored Japanese Bukkake
    • Sissyslut Harley
    • School Teacher XXX
    • Big Poop Holes
    • Kinky Shemale Bareback
    • Pretty Pretty Pretty
    • All the Way Through
    • Submissive Tranny Slut
    • Rectal Prolapse
    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