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

    Sissy Deep Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Deep
    Sissy Deep Throat
    Deep Anal Sissy
    Fuck Sissy Deep
    Sissy Deep Throat Training
    Crossdresser Sissy BBC Deep Throat
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Sissy Slave
    Amateur Sissy
    Sissy Blowjob
    Sissy Cuckold
    Best Videos
    By clicking the content you will also see an ad. AD
    Davine in latex stockings gets fist fucked till she cums hard
    08:50
    Davine in latex stockings gets fist fucked till she cums hard
    Davine
    15.7K views
    Hot sissy anal dildo deep passionate smooth wet trans girl
    03:49
    Hot sissy anal dildo deep passionate smooth wet trans girl
    CindieLove
    1.7K views
    Deep Throating Dildos Like a Good Trans Slut
    02:08
    Deep Throating Dildos Like a Good Trans Slut
    Gray Perrier
    1.3K views
    Davine gets caught fucking outdoor and has to blow deep, fuck doggystyle and swallow own cum
    14:02
    Davine gets caught fucking outdoor and has to blow deep, fuck doggystyle and swallow own cum
    Davine
    37.4K views
    Nun fuck sissy sinner hard and deep
    06:51
    Nun fuck sissy sinner hard and deep
    Saranji
    15.9K views
    My tight tiny sissy pussy fucked with huge alien style dildo machine
    49:48
    My tight tiny sissy pussy fucked with huge alien style dildo machine
    Ylvis88
    24.8K views
    Big, thick, dick in my fat ass. Anal machine is banging my booty nice and deep.
    27:56
    Big, thick, dick in my fat ass. Anal machine is banging my booty nice and deep.
    Bootyanal
    10.5K views
    Disturbing The Neighbors With Loud Deep Anal
    01:04
    Disturbing The Neighbors With Loud Deep Anal
    Khatara Shikiku
    6.3K views
    "Trans mechanic" photo shoot ends with the photographer's foot deep in the model's ass
    09:25
    "Trans mechanic" photo shoot ends with the photographer's foot deep in the model's ass
    Marie CD
    16.9K views
    Sissy Puppet Cumming Toy!
    00:45
    Sissy Puppet Cumming Toy!
    Lola Spais
    11K views
    obeyladymk & jadestorm8 Deep Fisting jasmine_dlight & Huge Strapon - Shemale Anal Slut
    02:45
    obeyladymk & jadestorm8 Deep Fisting jasmine_dlight & Huge Strapon - Shemale Anal Slut
    Jasmine_dlight
    17.4K views
    Sex Show Stripchat, Nudist Beach, Shemale and Guy, Gigi and Dave 17-05-2025, P1
    26:42
    Sex Show Stripchat, Nudist Beach, Shemale and Guy, Gigi and Dave 17-05-2025, P1
    Gigi and David
    8.6K views
    He fucked my Throat so deep and came inside
    15:45
    He fucked my Throat so deep and came inside
    Davine
    19.3K views
    My leaking clit from the side with balls deep 12 inch dildo
    54:07
    My leaking clit from the side with balls deep 12 inch dildo
    Ylvis88
    9.7K views
    Deep Throat’s Queen Monisa Serving Giant Belgian Man
    01:37
    Deep Throat’s Queen Monisa Serving Giant Belgian Man
    Monisa Vanboc
    6.6K views
    Fucking my ass deep in cute sundress
    05:21
    Fucking my ass deep in cute sundress
    RedLili
    21.6K views
    Femboy loud moaning and deep impaling
    05:17
    Femboy loud moaning and deep impaling
    Cheeky_Fem
    11.6K views
    Chastity Sissy training her pussy with BBC dildo
    02:05
    Chastity Sissy training her pussy with BBC dildo
    M MommyOwnsMe
    9K views
    Futa Shemale Deepthroat Face Fucking
    08:24
    Futa Shemale Deepthroat Face Fucking
    Wraith931
    3.5K views
    It's SO Big! Huge Dildo Deep Bussy Pounding with Fuck Machine - full video on LayneLovee Manyvids
    01:11
    It's SO Big! Huge Dildo Deep Bussy Pounding with Fuck Machine - full video on LayneLovee Manyvids
    Layne Love
    23.4K views
    Warming up with 17 inch giant dildo
    02:18
    Warming up with 17 inch giant dildo
    Ylvis88
    6.4K views
    Sissy Slut Deep Anal 40cm Dildo and Cum
    03:20
    Sissy Slut Deep Anal 40cm Dildo and Cum
    Alinatgirl
    1.6K views
    Redhead trans schoolgirl, rich, deep throat oral sex
    05:09
    Redhead trans schoolgirl, rich, deep throat oral sex
    Sexytransjordana25
    2.5K views
    CD with big fake tits deep throat’s bbc dildo
    02:07
    CD with big fake tits deep throat’s bbc dildo
    Sparx134
    5.4K views
    Sex Show Stripchat, Nudist Beach, Shemale and Guy, Gigi and Dave 17-05-2025, P2
    15:22
    Sex Show Stripchat, Nudist Beach, Shemale and Guy, Gigi and Dave 17-05-2025, P2
    Gigi and David
    7.5K views
    Deep Throat
    00:37
    Deep Throat
    Vlada Almazova
    1.4K views
    When Mara Jade's Ass Gets All Oiled Up, It Just Swallows Up the Cock
    02:36
    When Mara Jade's Ass Gets All Oiled Up, It Just Swallows Up the Cock
    MJ
    9.1K views
    Gigantic anal toy deep in my sissy ass, i think i'm in love with this toy
    13:38
    Gigantic anal toy deep in my sissy ass, i think i'm in love with this toy
    Ylvis88
    19K views
    Horny small cock sissy shemale deep throat and anal fuck
    06:43
    Horny small cock sissy shemale deep throat and anal fuck
    SissySimran
    162.5K views
    Taking it deep in both ends, I am an ATM machine!
    03:29
    Taking it deep in both ends, I am an ATM machine!
    Victoria Lecherri
    17.8K views
    Jasmine_dlight & Valentina Rosa - Big Dick Delivery Girl Gets a Tip - Giant Anal Dildo From Johnthomastoys
    00:31
    Jasmine_dlight & Valentina Rosa - Big Dick Delivery Girl Gets a Tip - Giant Anal Dildo From Johnthomastoys
    Jasmine_dlight
    12.1K views
    TvTs Isabella Coupe's Brutally wide dildo gushing after deep Penititration
    22:22
    TvTs Isabella Coupe's Brutally wide dildo gushing after deep Penititration
    TvTs Isabella Coupe
    32.3K views
    Amateur Sissy Millie practices for a deep throat
    05:20
    Amateur Sissy Millie practices for a deep throat
    Sissy Millie Lucy
    6K views
    Deep fisting
    01:07
    Deep fisting
    Lola Spais
    782 views
    Vikki Deeps gets her cock real hard, self sucks and cums for you!
    11:19
    Vikki Deeps gets her cock real hard, self sucks and cums for you!
    Cannagurlshredz
    6.1K views
    Horny Trans Girl Gets HARD Anal Pounding by Big Cock - Shadow Rick, Tskyliestar
    01:07
    Horny Trans Girl Gets HARD Anal Pounding by Big Cock - Shadow Rick, Tskyliestar
    TS Kylie Star
    4.1K views
    Deep Inside Ms. Grinch’s Tight grooty’ Hole
    03:12
    Deep Inside Ms. Grinch’s Tight grooty’ Hole
    Shy Boy
    4.1K views
    MASSIVE 10 Inch Dildo BALLS DEEP Makes me Cum Multiple Times - Jessica Bloom Anal Orgasm
    06:05
    MASSIVE 10 Inch Dildo BALLS DEEP Makes me Cum Multiple Times - Jessica Bloom Anal Orgasm
    Jessica Bloom
    28.6K views
    Fast and deep fuck with the giant anal toy
    09:49
    Fast and deep fuck with the giant anal toy
    Ylvis88
    15.6K views
    Sissygasm on huge deep toy in chastity
    05:12
    Sissygasm on huge deep toy in chastity
    Cannagurlshredz
    20.2K views
    Being Both #57-#60 Cumpilation
    08:12
    Being Both #57-#60 Cumpilation
    Being Both
    2.6K views
    Cross dressing sissy whore Trisha Trash stuffs her ass and practices deep throating
    04:14
    Cross dressing sissy whore Trisha Trash stuffs her ass and practices deep throating
    Trisha Trash
    1.3K views
    Majacumslut fuck doll loves to have the BBC deep in her slutty ass
    09:36
    Majacumslut fuck doll loves to have the BBC deep in her slutty ass
    MajaCumSlut
    17.6K views
    Tgirl gets deep fucking from sex machine - UKsexylegsTV
    04:23
    Tgirl gets deep fucking from sex machine - UKsexylegsTV
    UksexyLegsTV
    16.6K views
    Deep Slut 8 : MultiAudi (sissy)
    03:30
    Deep Slut 8 : MultiAudi (sissy)
    61.2K views
    Nyl Tasty Intense Blowjob Hot Deep Throat Sweet Hot Ass Getting Huge Cock in Her Tight Ass Sweet Pleasure
    10:17
    Nyl Tasty Intense Blowjob Hot Deep Throat Sweet Hot Ass Getting Huge Cock in Her Tight Ass Sweet Pleasure
    Hatanoxxxmiwa
    46.3K views
    Watch my whore ass struggle taking huge 13 inch dildo #painal
    03:34
    Watch my whore ass struggle taking huge 13 inch dildo #painal
    Linegirl94
    14.5K views
    • Back
    • 1
    • ...
    • 7
    • 8
    • 9
    • 10
    • 11
    • ...
    • 80
    • Next

    Searches Related to Sissy Deep

    • Midget Gangbanged
    • Cream Pie
    • Pegging Orgasm
    • Big Black XXX
    • Ladyboy Creampies
    • Messy
    • Backshots
    • Kinky
    • Stuck
    • Faye
    • Loose Asshole
    • Shemale Cry
    • Sissyslut
    • Danicooppss Porn
    • Full Nelson
    • From Behind
    • Trapitos Traps
    • Crossdressed Flight Attendant
    • Split Roast
    • Pantyhose Bulge

    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