PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels

    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
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • The sissy pain whore Alina show her skills in self-humiliation and deep throating with dildo
      02:55
      The sissy pain whore Alina show her skills in self-humiliation and deep throating with dildo
      alinanightsky
      28.4K views
    • 30cm long MrHankeys XXXcalibur monster dildo is long-legged femboy best remedy for solitude and cock crave
      04:32
      30cm long MrHankeys XXXcalibur monster dildo is long-legged femboy best remedy for solitude and cock crave
      Misha Purple
      3.4K views
    • Deep vibrating sound to tickle my prostate
      05:28
      Deep vibrating sound to tickle my prostate
      Vulva Cock Jez
      54.4K views
    • Another Shoulder Deep Fisting! Such a Good Time and so Many Fresh Fists!
      00:32
      Another Shoulder Deep Fisting! Such a Good Time and so Many Fresh Fists!
      Jasmine_dlight
      44.1K views
    • shemale deep throats and rides her toy till she cums
      06:28
      shemale deep throats and rides her toy till she cums
      pandascutiet
      16.4K views
    • Anal Stretching and Gape with a Dilator - Extreme Anal Insertions
      03:55
      Anal Stretching and Gape with a Dilator - Extreme Anal Insertions
      Jasmine_dlight
      45.1K views
    • Deep throat training in a tight black satin dress, stockings, satin opera gloves, blonde, lipstick, glasses, frustrated in chast
      04:41
      Deep throat training in a tight black satin dress, stockings, satin opera gloves, blonde, lipstick, glasses, frustrated in chast
      JessicaXD
      1.3K views
    • Gigi and Dave - Sex and Tease on a Nudist Beach. Extra Edition. Shemale Dogging Outdoor
      01:00:09
      Gigi and Dave - Sex and Tease on a Nudist Beach. Extra Edition. Shemale Dogging Outdoor
      Gigi and David
      65K views
    • Shemale Monisa Vanboc sucking hung French deep throat cum in mouth
      04:53
      Shemale Monisa Vanboc sucking hung French deep throat cum in mouth
      Monisa Vanboc
      15.3K views
    • mistress roleplay i fuck u hard like my little sissy toy and cum deep inside you
      03:05
      mistress roleplay i fuck u hard like my little sissy toy and cum deep inside you
      Nadja Cox
      72.5K views
    • Futa Dickgirl Extreme Deepthroating A Hot Blonde Girl
      08:48
      Futa Dickgirl Extreme Deepthroating A Hot Blonde Girl
      Wraith931
      2.7K views
    • Céline Laffite back based as she likes
      02:22
      Céline Laffite back based as she likes
      Celine LAFFITE
      104K views
    • Sexy sissy fisted while sliding a sounding rod deep in her chastity locked clit until squirting everywhere
      05:48
      Sexy sissy fisted while sliding a sounding rod deep in her chastity locked clit until squirting everywhere
      Cannagurlshredz
      23.1K views
    • Giant Strap-on!
      04:22
      Giant Strap-on!
      Lola Spais
      1.6K views
    • Lot requested outfit and toy - Going deep in to anal
      09:42
      Lot requested outfit and toy - Going deep in to anal
      Ylvis88
      105.2K views
    • Two Trans Having Fun 37 Part 1
      05:45
      Two Trans Having Fun 37 Part 1
      Royats
      2.1K views
    • BBC Ken Fucks Me on My Back in Missionary with Verbal Dom Sissification - Candy Ass Sissy in Chastity Cage
      06:51
      BBC Ken Fucks Me on My Back in Missionary with Verbal Dom Sissification - Candy Ass Sissy in Chastity Cage
      Candy Ass Sissy
      21.8K views
    • Sexy Mature Crossdressing sissy slut Takes It Deep
      23:51
      Sexy Mature Crossdressing sissy slut Takes It Deep
      Shystockings
      1.5K views
    • Old friend comes over for reconciliation sex - More on Onlyfans Veronica Sanders
      05:11
      Old friend comes over for reconciliation sex - More on Onlyfans Veronica Sanders
      Veronica Sanders
      13K views
    • hot ass sissy. riding big long toy deep and good whilst vibrating cage
      01:15
      hot ass sissy. riding big long toy deep and good whilst vibrating cage
      Lisa Rhea Deville
      1.4K views
    • Brie Meets Thad (feat. Thad Maxxx)
      08:12
      Brie Meets Thad (feat. Thad Maxxx)
      Brie Lovely
      1K views
    • Sissy Monika CD in Chastity cumming on a Huge black Dildo
      06:11
      Sissy Monika CD in Chastity cumming on a Huge black Dildo
      M MonikaCD
      29.9K views
    • Davine gets a deep fisting after having a ride on a huge toy.
      15:30
      Davine gets a deep fisting after having a ride on a huge toy.
      Davine
      44.8K views
    • What a deep throat my Sissy Blaire_18 has. Strapon fucking in the mouth
      06:15
      What a deep throat my Sissy Blaire_18 has. Strapon fucking in the mouth
      Dominatrix Nika
      16.1K views
    • Being Both #63-i’m at and on the New Dildo Again! How Exquisite It Is! - Being Both
      08:34
      Being Both #63-i’m at and on the New Dildo Again! How Exquisite It Is! - Being Both
      Being Both
      2.2K views
    • Full Set of Pool Balls Inserted & Pulled Out by valentinarosa89 stretch_events Extreme Anal, Deep Fisting Elbow and Shoulder
      00:32
      Full Set of Pool Balls Inserted & Pulled Out by valentinarosa89 stretch_events Extreme Anal, Deep Fisting Elbow and Shoulder
      Jasmine_dlight
      47.6K views
    • Little Sissy Crossdresser Love My Big Dick - BBC Fuck Me Deep and Hard Part1
      16:56
      Little Sissy Crossdresser Love My Big Dick - BBC Fuck Me Deep and Hard Part1
      Rozebella
      5.1K views
    • Sissy sounds deep her urethra, ties up his big cock and balls, and makes herself cum hard
      09:25
      Sissy sounds deep her urethra, ties up his big cock and balls, and makes herself cum hard
      MyLolaTrav
      33.5K 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
      18.3K views
    • Sissy TGirl Slut Lucy gets fucked deep by huge 9.5 inch BBC
      05:41
      Sissy TGirl Slut Lucy gets fucked deep by huge 9.5 inch BBC
      Spike Essex
      76.8K views
    • Cute Trans-Girl gets her ass barebacked deep and creampied - prettyboi2000x
      17:16
      Cute Trans-Girl gets her ass barebacked deep and creampied - prettyboi2000x
      Prettyboi2000x
      2K views
    • Fuck Machine Plows Sissy Asshole Deep And Hard - Anal Orgasm in Chastity
      07:27
      Fuck Machine Plows Sissy Asshole Deep And Hard - Anal Orgasm in Chastity
      Jessica Bloom
      6.4K views
    • Little shemale likes it rough and deep
      02:19
      Little shemale likes it rough and deep
      LittleVixenSlut
      6K views
    • Big Cock TGirl Lucy gets a deep throat blow job and fucks sexy MILF Lisa
      06:22
      Big Cock TGirl Lucy gets a deep throat blow job and fucks sexy MILF Lisa
      Spike Essex
      82.7K views
    • If you love your car.... Sissy Rides On Gear Knob Until Cumshot
      05:08
      If you love your car.... Sissy Rides On Gear Knob Until Cumshot
      Marie CD
      18.6K views
    • We take turns fucking deep into each other's asses
      05:10
      We take turns fucking deep into each other's asses
      ShemaleTSTiara
      28.6K views
    • Big dick TGirl Lucy hard anal bareback with Milf Lisa Essex
      14:25
      Big dick TGirl Lucy hard anal bareback with Milf Lisa Essex
      Spike Essex
      1K views
    • Fucking big ass femboy with bunny custome
      10:19
      Fucking big ass femboy with bunny custome
      Saranji
      24.8K views
    • Huge Dildo as a reward for beeing a good Slut.
      02:51
      Huge Dildo as a reward for beeing a good Slut.
      Davine
      20.2K views
    • Huge dildo is pushed deeper into the ass by rubber bands. BDSM TS self bondage torture. Huge Tits Cup-Z Anal Fuck Extreme deep
      06:07
      Huge dildo is pushed deeper into the ass by rubber bands. BDSM TS self bondage torture. Huge Tits Cup-Z Anal Fuck Extreme deep
      Endless Deeply
      54.7K views
    • Nudist Beach Stripchat Sex Show Gigindave Shemale Girlfriend Encounter Mobile
      28:29
      Nudist Beach Stripchat Sex Show Gigindave Shemale Girlfriend Encounter Mobile
      Gigi and David
      11.5K views
    • Black Sissy Dickgirl Eating Ass in Deep Rimjob
      08:34
      Black Sissy Dickgirl Eating Ass in Deep Rimjob
      Wraith931
      2.4K views
    • Deep Dildo Daddy Dirty Talk Sissy Cd Ts Anal Slut PART TWO
      10:57
      Deep Dildo Daddy Dirty Talk Sissy Cd Ts Anal Slut PART TWO
      CindieLove
      46.7K views
    • Chastity Sissy Cums From Big Black Cock Fucking Machine And Swallows Her Own Cum
      08:07
      Chastity Sissy Cums From Big Black Cock Fucking Machine And Swallows Her Own Cum
      Jessica Bloom
      11.2K views
    • More Locktober Frustrated Sissy Milking Jessica Bloom Chastity Slut
      05:20
      More Locktober Frustrated Sissy Milking Jessica Bloom Chastity Slut
      Jessica Bloom
      6.7K views
    • Femboy Gives Stepdad Blowjob Deepthroating
      11:58
      Femboy Gives Stepdad Blowjob Deepthroating
      Blackfemboygerman
      50.5K views
    • Christmas greetings from secret santa bunny Harin! Got dildos as a present and gave you a deep blowjob under the Christmas tree.
      09:58
      Christmas greetings from secret santa bunny Harin! Got dildos as a present and gave you a deep blowjob under the Christmas tree.
      Harinni
      2.2K views
    Previous page
    Next page
    1
    1. 1
    2. ...
    3. 5
    4. 6
    5. 7
    6. 8
    7. 9
    8. ...
    9. 44
    10. ...
    11. 80
    80

    Searches Related to Sissy Deep

    • Crossdreser
    • Ferro Network
    • Boypussy
    • Bully
    • Tight Assholes
    • Monster Cock Screaming
    • Xxxl
    • Barebacked
    • Transvestite Sluts
    • Alpha Male
    • Sheboy
    • Intense
    • Thigh Gap
    • Sloppy Hole
    • Cute Sissy Femboy
    • Destroyed
    • Cant Handle
    • Dildo Panties
    • Beautiful Agony
    • Public Buttplug
    Monetize your content
    Become a creator

    xHamster

    • About us
    • 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

    Earn money with us

    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    © 2026 xHamster - Free porn videos.
    Desktop 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