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

    Sissy Dressing Up Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Dress
    Dress up
    Sissy Dress up JOI
    Sissy Instructions JOI Dress up
    Sissy Faggot Playing Dress up
    Sissy Maid Dress up for Mistress
    Dominatrix Dresses up Sissy in Dress
    Sissy Crossdresser
    Sissy Training
    Sissy Feminization
    Sissy BBC
    Sissy Chastity
    Sissy Husband
    Sissy Compilation
    Sissy Fucked
    Sissy Blowjob
    Amateur Sissy
    Sissy Gangbang
    Sissy Slave
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Gothic Sissy Slut In Pink Dress Workouts With Her BBC Dildo
      09:16
      Gothic Sissy Slut In Pink Dress Workouts With Her BBC Dildo
      Vane03_siss
      21.8K views
    • Sexy TS Lucia Maya in mini dress and heels FUCKS HER ASS UNTIL SHE CUMS
      24:59
      Sexy TS Lucia Maya in mini dress and heels FUCKS HER ASS UNTIL SHE CUMS
      Lucia Maya
      112.2K views
    • Trans dresses as teacher, cosplay, wants to play with his students
      05:35
      Trans dresses as teacher, cosplay, wants to play with his students
      Letany Ponny
      232.9K views
    • kinky gothic slut outdoor exploring the city center.
      01:17:08
      kinky gothic slut outdoor exploring the city center.
      emy4all
      11.1K views
    • green style shemale with big dick cumshot in your face
      03:11
      green style shemale with big dick cumshot in your face
      Nadja Cox
      148.7K views
    • skinny white shemale black latex strips outfit ride bbc dildo much precum
      03:05
      skinny white shemale black latex strips outfit ride bbc dildo much precum
      Nadja Cox
      80.3K views
    • Sissy Femboy wears various sexy women clothes
      05:11
      Sissy Femboy wears various sexy women clothes
      36.9K views
    • Fucking in Sexy Dress with Stepbrother
      06:33
      Fucking in Sexy Dress with Stepbrother
      Crystal Phoenix
      8K views
    • Loooove my new red thigh high pvc boots ️ x
      02:32
      Loooove my new red thigh high pvc boots ️ x
      JessicaXD
      5.7K views
    • Larissa1sexdoll. Into the black hole.  Mega gape. Double ass piercing.
      10:11
      Larissa1sexdoll. Into the black hole. Mega gape. Double ass piercing.
      Larissa1sexdoll
      249.3K views
    • Playing in a gorgeous dress and lingerie!
      05:42
      Playing in a gorgeous dress and lingerie!
      Rachel_biTV_uk
      30.7K views
    • Sissy jerks off cock and fucks toy, wearing a short dress
      06:32
      Sissy jerks off cock and fucks toy, wearing a short dress
      Bbrgurl
      25.5K views
    • Sexy sissy in pink lingerie loves playing with her toys. cross dressing femboy fucks ass riding dildo
      06:21
      Sexy sissy in pink lingerie loves playing with her toys. cross dressing femboy fucks ass riding dildo
      Marcus Domes
      8.9K views
    • Man Dressed as Woman and Fucked by Dominatrix
      06:11
      Man Dressed as Woman and Fucked by Dominatrix
      Bailey Wilde
      215.9K views
    • skinny pale slut with pink outfit and lips big cumshot self facial
      02:36
      skinny pale slut with pink outfit and lips big cumshot self facial
      Nadja Cox
      7.9K views
    • Redhead bitch in a white dress loves anal
      01:16
      Redhead bitch in a white dress loves anal
      Kenny White
      67.3K views
    • Fucked Doggy in a Cute Little Outfit
      08:12
      Fucked Doggy in a Cute Little Outfit
      FapHouse
      26.1K views
    • Mistress Gives Her Caged Sissy a little Spanking – Obedience and Discipline Lesson
      05:13
      Mistress Gives Her Caged Sissy a little Spanking – Obedience and Discipline Lesson
      Lucy Dee
      10.1K views
    • How to wear a flat chastity cage
      05:16
      How to wear a flat chastity cage
      Andreina Naty
      60.4K views
    • Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm
      13:54
      Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm
      FapHouse
      42.1K views
    • Tranny Girl slipless under summer dress! Shameless public wanking in the city!
      00:37
      Tranny Girl slipless under summer dress! Shameless public wanking in the city!
      Mydirtyhobby
      196.1K views
    • Playing in my lovely blue dress and lingerie - Part 3
      05:15
      Playing in my lovely blue dress and lingerie - Part 3
      Rachel_biTV_uk
      41.5K views
    • Exhibition of my big cock in the public woods in slut outfit wanks and cumshots
      05:50
      Exhibition of my big cock in the public woods in slut outfit wanks and cumshots
      FapHouse
      72.7K views
    • My girlfriend made me dress like a slutty sissy and film it for my Grindr
      05:10
      My girlfriend made me dress like a slutty sissy and film it for my Grindr
      OneWhoHasFun
      10.8K views
    • Dress like a Sissy Slut
      04:33
      Dress like a Sissy Slut
      62.3K views
    • Sissy embarrassing education with cock puppet dress
      04:37
      Sissy embarrassing education with cock puppet dress
      164.5K views
    • Sexy Japanese tgirl in Bimbo dress playing with dildo
      04:20
      Sexy Japanese tgirl in Bimbo dress playing with dildo
      Letany Ponny
      116.6K views
    • cute skinny shemale summer dress huge dildo dirty ride intense cum
      02:20
      cute skinny shemale summer dress huge dildo dirty ride intense cum
      Onlyfans
      91.2K views
    • I'm Not Wearing - Pai-chan, the Pervert's Fully-Naked Bottom - Japanese Sissy dressed in Black
      06:22
      I'm Not Wearing - Pai-chan, the Pervert's Fully-Naked Bottom - Japanese Sissy dressed in Black
      Pai-chan
      67.2K views
    • Maximum punishment for chaste loser slave: fuck rubber doll with cage!
      01:17
      Maximum punishment for chaste loser slave: fuck rubber doll with cage!
      Mydirtyhobby
      50.3K views
    • Cute Housewife Ladyboy Sweet Cock Shemale Hot Short Dress Blonde Sissy Femboy Crossdresser
      04:31
      Cute Housewife Ladyboy Sweet Cock Shemale Hot Short Dress Blonde Sissy Femboy Crossdresser
      Crossdresserkitty
      116.4K views
    • Beril, who combines with her lover for a date, has a hard time deciding what to wear.
      05:32
      Beril, who combines with her lover for a date, has a hard time deciding what to wear.
      Usaberilx
      6.1K views
    • Reina Hanno White Pearl Themed Dress & Sounding
      01:02
      Reina Hanno White Pearl Themed Dress & Sounding
      Reina Hanno
      3.4K views
    • Trans girl in a very short dress rubs his big cock to squeeze out all his cum
      15:11
      Trans girl in a very short dress rubs his big cock to squeeze out all his cum
      Kayndrift 0wtis
      2.4K views
    • Teen Femboy Sissy White Dress Anal Masturbation
      08:44
      Teen Femboy Sissy White Dress Anal Masturbation
      FapHouse
      16.7K views
    • A redhead getting butt-fucked from behind
      12:26
      A redhead getting butt-fucked from behind
      Sabrina Iu
      60.5K views
    • Finger My Ass and Swallow My Cum
      02:24
      Finger My Ass and Swallow My Cum
      FapHouse
      10.1K views
    • Crossdresser in very short dresses & skirts outside
      05:10
      Crossdresser in very short dresses & skirts outside
      24.8K views
    • Christmas party dress bulge
      03:18
      Christmas party dress bulge
      Hollycd1
      3K views
    • Josie Blade sensual session in my fuck me dress
      19:55
      Josie Blade sensual session in my fuck me dress
      Josie Blade
      267K views
    • Sexy femboy in sexy dress on high heels
      05:42
      Sexy femboy in sexy dress on high heels
      Letany Ponny
      62.2K views
    • Red Dress Crossdresser Fucks Red Lingerie Petite Trans Woman
      06:03
      Red Dress Crossdresser Fucks Red Lingerie Petite Trans Woman
      Onlyfans
      29.2K views
    • Denim Girl
      08:12
      Denim Girl
      Melinda James
      16.8K views
    • Sissy in teal dress and pantyhose cums hard with prostate machine
      04:55
      Sissy in teal dress and pantyhose cums hard with prostate machine
      Nylonizer
      2.9K views
    • Little Blonde Doll Teases You in a Tight Mini Dress (without Panties?)
      01:17
      Little Blonde Doll Teases You in a Tight Mini Dress (without Panties?)
      FapHouse
      12.2K views
    • Sissy getting fucked in wedding dress
      01:31
      Sissy getting fucked in wedding dress
      148.8K views
    • My new short. tight dress turns me on so much i can't hold back my erection, so I decided to fuck and jerk off until I cum
      20:41
      My new short. tight dress turns me on so much i can't hold back my erection, so I decided to fuck and jerk off until I cum
      Bbrgurl
      34.3K views
    Previous page
    Next page
    1
    1. 1
    2. ...
    3. 6
    4. 7
    5. 8
    6. 9
    7. 10
    8. ...
    9. 44
    10. ...
    11. 80
    80

    Searches Related to Sissy Dressing Up

    • Pure TS List
    • Crossdreser Sex
    • Real First Time
    • Tgirl Slave
    • Instagram Models Leaked
    • See Through Panties
    • Feminine Beauty
    • Fucked Machine Chastity
    • X Rated
    • Sissyslut Harley
    • 18 Xx
    • Sissyfreya
    • Transvestite Restaurant
    • Shy Trap
    • Cross Dressers
    • Funny Accident
    • Nylonizer
    • Sundress
    • Boys Will Be Girls
    • Little Sluttb
    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