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
    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 Boyfriend Strapon Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Degraded Sissies
    Indian Sissy
    Sissy Handjob
    Sissy Kissing
    Sissy CD
    Goon Sissy
    Sissy Bride
    Sissy Milking
    Sissy Interracial
    Skinny Sissy
    Sissy Outdoor
    Sissy Secrets
    Sissy Feet
    Arab Sissy
    Sissy Submission
    Sissy Pussy
    Bi Sissy
    Sissy Torture
    Sissy Dress
    Sissy Destroyed
    Best Videos
    By clicking the content you will also see an ad. AD
    Being a good little sissy maid, all dressed up in her black satin French maid dress, fishnet stockings, 6 strap suspenders
    07:12
    Being a good little sissy maid, all dressed up in her black satin French maid dress, fishnet stockings, 6 strap suspenders
    JessicaXD
    910 views
    Latex sissy in chastity and fucked by Mistress
    05:31
    Latex sissy in chastity and fucked by Mistress
    Abby Kitty
    71.6K views
    Welcome to Our Live Show!
    05:44
    Welcome to Our Live Show!
    FrinaXXX
    7.5K views
    Lola Cumming Cunt
    02:14
    Lola Cumming Cunt
    FrinaXXX
    4.4K views
    compilation where I fuck the big ass of my sissy slut who loves cock a real slut
    05:19
    compilation where I fuck the big ass of my sissy slut who loves cock a real slut
    Nady-So
    4.3K views
    Balltorture with fuckmachine
    21:58
    Balltorture with fuckmachine
    Niceguy_1991
    22.6K views
    Woman Puts Nails on Crossdresser
    05:02
    Woman Puts Nails on Crossdresser
    Bailey Wilde
    2.8K views
    Trans slut fucked and fisted until her tight hole gapes & Anal and femdom - Cyberpunk cosplay
    05:10
    Trans slut fucked and fisted until her tight hole gapes & Anal and femdom - Cyberpunk cosplay
    CutePinkUnicorn
    27.2K views
    Sissy Charlotte licks Lisas pussy then gets pegged with a strapon
    12:48
    Sissy Charlotte licks Lisas pussy then gets pegged with a strapon
    Lisa Essex
    31.4K views
    I Test Dildos From the Smallest to the Biggest Until Orgasm
    11:18
    I Test Dildos From the Smallest to the Biggest Until Orgasm
    Nady-So
    1.2K views
    Part 3:- Domina Satana, Mistress Carrie does a Double Domme session
    06:04
    Part 3:- Domina Satana, Mistress Carrie does a Double Domme session
    Aaexperiencesltd
    1K views
    Sissy gets fucked dildo anal toy strap
    09:02
    Sissy gets fucked dildo anal toy strap
    Sasha Earth
    17.1K views
    Sitting on My Sissy GF's Face
    00:46
    Sitting on My Sissy GF's Face
    Brat Perversions
    11K views
    Belyla Bradley Puts Nails on Sissy Bailey Wilde
    05:06
    Belyla Bradley Puts Nails on Sissy Bailey Wilde
    Bailey Wilde
    2.5K views
    Sweet Sissygasm Riding a Bb Strapon
    00:51
    Sweet Sissygasm Riding a Bb Strapon
    Lola Spais
    4.5K views
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 3
    20:06
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 3
    Bailey Wilde
    1K views
    Sissy Charlotte fucks post op trans girl Lisa with strap on
    07:05
    Sissy Charlotte fucks post op trans girl Lisa with strap on
    Lisa Essex
    51.6K views
    Cumshot on Huge Black Strapon Dick!!
    01:02
    Cumshot on Huge Black Strapon Dick!!
    Lola Spais
    4.9K views
    Live Megafuck Cumshot on Bb Free Hands
    00:38
    Live Megafuck Cumshot on Bb Free Hands
    Lola Spais
    5.5K views
    Sexy British MILF Lisa Femdom Pegging Horny TGirl Gigi
    12:00
    Sexy British MILF Lisa Femdom Pegging Horny TGirl Gigi
    Lisa Essex
    15.2K views
    MILF Mistress Fucks and Peggs Her Polish Sissy
    10:57
    MILF Mistress Fucks and Peggs Her Polish Sissy
    Margo-apollo
    14.3K views
    Pegging Strapon Fuck
    03:11
    Pegging Strapon Fuck
    FrinaXXX
    5.6K views
    Man Dressed as Woman in Chastity and Strapon Fucked
    02:24
    Man Dressed as Woman in Chastity and Strapon Fucked
    Bailey Wilde
    37.2K views
    Sexy Sissy in Chastity Strapon Fucked by Dominatrix
    08:19
    Sexy Sissy in Chastity Strapon Fucked by Dominatrix
    Bailey Wilde
    30.8K views
    Girl destroys my fat pussy
    08:52
    Girl destroys my fat pussy
    Moitsex
    22.5K views
    I fuck my stepsister for her pussy and she likes it a lot
    08:22
    I fuck my stepsister for her pussy and she likes it a lot
    brenda paola rojas villasmil
    35.8K views
    Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 8
    08:12
    Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 8
    Bailey Wilde
    9.9K views
    Pegging sissy TGirl until she sissygasms on her own face
    04:30
    Pegging sissy TGirl until she sissygasms on her own face
    Lisa Essex
    37.6K views
    Webcam Depraved Fun Trans Couples
    11:12
    Webcam Depraved Fun Trans Couples
    Lola Spais
    4.6K views
    3mins BBC Riding 28cm
    01:28
    3mins BBC Riding 28cm
    LanaSherin
    3.6K views
    Sissy Slut's Use of BBC
    11:12
    Sissy Slut's Use of BBC
    Lola Spais
    14.7K views
    Sissy in harness have sex anal with toy dildo
    05:42
    Sissy in harness have sex anal with toy dildo
    Sasha Earth
    36.8K views
    Stroking with analplug sissy maid
    05:25
    Stroking with analplug sissy maid
    Zoeycdgirl
    11.5K views
    Strapon fuck
    01:32
    Strapon fuck
    Lola Spais
    just added
    A Bad Girl
    05:23
    A Bad Girl
    Emily Rossi
    27.1K views
    Sissy Gothic in Chastity on a Strapon on Her Pillow
    12:29
    Sissy Gothic in Chastity on a Strapon on Her Pillow
    Vane03_siss
    3.8K views
    Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 11
    08:12
    Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 11
    Bailey Wilde
    6.5K views
    Watching Porn and Frotting with your FtM Roommate Jaq Quicksilver - POV JOI
    11:58
    Watching Porn and Frotting with your FtM Roommate Jaq Quicksilver - POV JOI
    Jaq Quicksilver
    6K views
    Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 19
    20:06
    Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 19
    Bailey Wilde
    893 views
    Sub Cums Between valentinarosa89 and I - Mistress and Shemale Double Top a Sub Slut
    03:12
    Sub Cums Between valentinarosa89 and I - Mistress and Shemale Double Top a Sub Slut
    Jasmine_dlight
    8.4K views
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 16
    08:12
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 16
    Bailey Wilde
    8.1K views
    The nee toy to enjoy. Mistress Monoca fucks her sissys slave Aliska With a big dildo.
    04:18
    The nee toy to enjoy. Mistress Monoca fucks her sissys slave Aliska With a big dildo.
    Aliska
    9.9K views
    Armbinder tied to Chastity Cage Sissy Maid Self Bondage
    47:08
    Armbinder tied to Chastity Cage Sissy Maid Self Bondage
    Derek6699
    17K views
    Hot Crossdresser Riding HUGE Strapon
    04:44
    Hot Crossdresser Riding HUGE Strapon
    Bailey Wilde
    3.6K views
    Fucking My Anal Vagina
    15:52
    Fucking My Anal Vagina
    LastWhore7
    1.1K views
    Contraband - Part 2 - Heathrow Dungeon Come to Punish for Her Smuggling
    01:35
    Contraband - Part 2 - Heathrow Dungeon Come to Punish for Her Smuggling
    Jasmine_dlight
    10.2K views
    Femdom Pegging sexy TGirl Lisa with huge depth training dildo
    12:22
    Femdom Pegging sexy TGirl Lisa with huge depth training dildo
    Lisa Essex
    20.4K views
    • Back
    • 1
    • ...
    • 4
    • 5
    • 6
    • 7
    • 8
    • ...
    • 80
    • Next

    Searches Related to Sissy Boyfriend Strapon

    • Silky Sindy
    • Oh No No No No
    • See Through Lingerie
    • Vintage Transsexual Movie
    • Karley Sonata Cums
    • Girl's Body Xxxxx Xxxxx Video
    • Girls Xxxx
    • Fem Katey
    • Crossdresserkitty
    • Pinky Susy
    • Inserting Large Objects
    • Sissyjay
    • Girlcock Brainwashing
    • Crossdresser Love
    • Gorgeous Femboy
    • Bathroom Gloryhole
    • Guy Rides Shemale Cock
    • Femdom Emasculation
    • Sissy-Cori
    • Sis Swap
    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