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
    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 Session Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy Interracial
    Sissy Bride
    Sissy Boyfriend
    Degraded Sissies
    Femboy Sissy
    Sissy Pussy
    Sissy Feet
    Sissy Confusion
    Bi Sissy
    Sissy Outdoor
    Sissy Submission
    Sissy Torture
    Goon Sissy
    Sissy Dress
    Skinny Sissy
    British Sissy
    Sissy Secrets
    Sissy Hotel
    Sissy Sex
    Sissy Destroyed
    Best Videos
    By clicking the content you will also see an ad. AD
    Red Lingerie Fuck Chair Solo Horny Session - Extreme Insertion, Gape and Sounding Extreme Anal
    11:12
    Red Lingerie Fuck Chair Solo Horny Session - Extreme Insertion, Gape and Sounding Extreme Anal
    Jasmine_dlight
    4.9K views
    Sissy Skype Session - School uniform
    01:48
    Sissy Skype Session - School uniform
    robbietest
    56.6K views
    Please Make Me Your Obedient Sissy, Jerk off Session.
    05:57
    Please Make Me Your Obedient Sissy, Jerk off Session.
    Apple00001
    2.3K views
    Solo Trans Tease Session, Pure Confidence & Self-Love
    35:50
    Solo Trans Tease Session, Pure Confidence & Self-Love
    Reynaldo6
    just added
    Cam session pt5 : Sissy pig humiliation
    04:55
    Cam session pt5 : Sissy pig humiliation
    11.9K views
    Full Session Anal Big Dildo
    12:28
    Full Session Anal Big Dildo
    Branquinha Large
    7.3K views
    Sissy Chastity Fuck Machine Session
    01:05
    Sissy Chastity Fuck Machine Session
    6.2K views
    Last Part of a Long Purple Pvc Fuck Session, the Last Round of Massive Xl Extreme Anal Toys
    03:08
    Last Part of a Long Purple Pvc Fuck Session, the Last Round of Massive Xl Extreme Anal Toys
    Jasmine_dlight
    4.4K views
    Session with a Can of Monster Energy Drink Complete with Blows to the Ass
    03:47
    Session with a Can of Monster Energy Drink Complete with Blows to the Ass
    Branquinha Large
    8K views
    Corporal Punishment Session with Mistress Jamie & Diaper Sis
    01:06:07
    Corporal Punishment Session with Mistress Jamie & Diaper Sis
    10.7K views
    Lovely Estim and cum session
    02:07
    Lovely Estim and cum session
    5K views
    Anoniema Rose's slutschool - Totally butt naked session
    10:44
    Anoniema Rose's slutschool - Totally butt naked session
    Anoniema Rose
    1.9K views
    Sexy Crossdresser Solo Playtime  Naughty Self-pleasure Session
    03:20
    Sexy Crossdresser Solo Playtime Naughty Self-pleasure Session
    690 views
    Babe Ladyboy Model on Photo Session Cute Sexy Hot Shemale
    06:46
    Babe Ladyboy Model on Photo Session Cute Sexy Hot Shemale
    Crossdresserkitty
    4.3K views
    Perverted masseuse rubs shemale woman (sexy massage session)
    12:32
    Perverted masseuse rubs shemale woman (sexy massage session)
    victoriamanaure43
    2.9K views
    Perverted masseuse rubs transsexual woman (massage session)
    10:12
    Perverted masseuse rubs transsexual woman (massage session)
    victoriamanaure43
    2.1K views
    Tgirl Camelia - large dildo session
    06:22
    Tgirl Camelia - large dildo session
    Beacons
    12.1K views
    Cam session pt7 : Garbage sissy pig humiliation
    43:37
    Cam session pt7 : Garbage sissy pig humiliation
    8.2K views
    Sexy Crossdresser kellycd2022 cum in my seamless pantyhose after a cam session
    04:31
    Sexy Crossdresser kellycd2022 cum in my seamless pantyhose after a cam session
    Kellycd2022
    4.3K views
    Happythinkins video - Another Trap Fap Session With Outfit Change - Part 1.
    17:44
    Happythinkins video - Another Trap Fap Session With Outfit Change - Part 1.
    Ms Tallpalenpretty
    6.2K views

    Relevant Short videos

    Sissy Session
    Sissy Session
    UrSissySlaveXXX
    798 views
    Sample on my live session, i just love this toy ❤️
    Sample on my live session, i just love this toy ❤️
    Ylvis88
    2.2K views
    I'm positively glowing while filming this session!
    I'm positively glowing while filming this session!
    Lola Femme
    2K views
    Deepthroat Training Session for Sissy Elodie
    Deepthroat Training Session for Sissy Elodie
    Elodiefrench
    3.4K views
    A sneak peek into my last play sessions
    A sneak peek into my last play sessions
    Kayla_Kandii
    1.5K views
    First Session with Giant Dildo (12")
    First Session with Giant Dildo (12")
    Ximena PA
    1.3K views
    Dildo and fucking machine session for sexy French Trans Camelia
    08:08
    Dildo and fucking machine session for sexy French Trans Camelia
    Beacons
    3.5K views
    Anal Session 2
    08:15
    Anal Session 2
    MaureenNadh
    6.6K views
    Lady Alice compilation 03 big dildo and deepthroat and glamour fetish session. lingerie, pantyhose, high heels, lipstick
    06:18
    Lady Alice compilation 03 big dildo and deepthroat and glamour fetish session. lingerie, pantyhose, high heels, lipstick
    Mesmeriza
    5.5K views
    Rebecca Farron - 2025.06.27 cam session part 2 - stripping and showing off for the camera
    12:50
    Rebecca Farron - 2025.06.27 cam session part 2 - stripping and showing off for the camera
    Rebecca Farron
    885 views
    Desperate Sissy training solo session
    07:05
    Desperate Sissy training solo session
    WanabeSissy Plz
    1K views
    Anal Inflatable Stretch Session in Lingerie
    04:10
    Anal Inflatable Stretch Session in Lingerie
    Jasmine_dlight
    3.6K views
    Dropping Cum up My Sissy Ass After a Fuck Session
    03:29
    Dropping Cum up My Sissy Ass After a Fuck Session
    JenniferStarTS
    981 views
    Petite femboy with plump bootyhole and big BBC jack off session
    05:22
    Petite femboy with plump bootyhole and big BBC jack off session
    SweetDWillie456
    1.9K views
    Anal Session - latex, nose mask, slink dildo, high heels
    47:20
    Anal Session - latex, nose mask, slink dildo, high heels
    Enyn
    17.3K views
    Latex Fetish Nurse edging during one of her cam sessions
    01:21
    Latex Fetish Nurse edging during one of her cam sessions
    JessicaXD
    437 views
    Rebecca Farron - 2025.06.27 cam session part 1 - dildo blowjob and deepthroat
    12:07
    Rebecca Farron - 2025.06.27 cam session part 1 - dildo blowjob and deepthroat
    Rebecca Farron
    690 views
    Sizzling POV Cum Session.
    10:13
    Sizzling POV Cum Session.
    Xshen Hunk
    1.9K views
    Mind the Gape Training Quickie Session - Membership Teaser
    01:24
    Mind the Gape Training Quickie Session - Membership Teaser
    Pussless
    just added
    session with my fuck machine
    06:13
    session with my fuck machine
    34.7K views
    Amazing Feet Tranny MILF Fucking Sex Session with Huge Toys
    14:21
    Amazing Feet Tranny MILF Fucking Sex Session with Huge Toys
    JenniferStarTS
    2.3K views
    Femboy Mika Kawaiii Public Trail Twerk Session (Preview)
    05:12
    Femboy Mika Kawaiii Public Trail Twerk Session (Preview)
    miikakawaiii
    3.6K views
    Part 2 of a Session with Some Huge Xl Toys
    05:55
    Part 2 of a Session with Some Huge Xl Toys
    Jasmine_dlight
    3.7K views
    Sissy Rubberdoll Vibrator session
    06:29
    Sissy Rubberdoll Vibrator session
    Miss Lacy Duval
    6.9K views
    tv lisa rhea dildo session
    02:59
    tv lisa rhea dildo session
    Lisa Rhea Deville
    2.3K views
    My Training Session
    09:33
    My Training Session
    J Jacky_CD
    1.5K views
    CD-Session 31.1.25, black heels, red dress, glass plug
    01:39
    CD-Session 31.1.25, black heels, red dress, glass plug
    UrSissySlaveXXX
    1.6K views
    kit restrained to the bed solo bdsm session
    13:22
    kit restrained to the bed solo bdsm session
    kit69lupin
    1.3K views
    Another long habit forming session
    10:58
    Another long habit forming session
    2.4K views
    Fat ass big dick thug jack off session
    05:22
    Fat ass big dick thug jack off session
    SweetDWillie456
    2K views
    CD Tranny Anal Slut Selena Wednesday fucking Session Clip 4
    03:42
    CD Tranny Anal Slut Selena Wednesday fucking Session Clip 4
    Selenahot
    2K views
    Subverse Sessions Doubts
    07:58
    Subverse Sessions Doubts
    Asura
    5.1K views
    Perverted masseuse rubs shemale woman (horny massage session)
    10:10
    Perverted masseuse rubs shemale woman (horny massage session)
    victoriamanaure43
    3.6K views
    • Back
    • 1
    • ...
    • 4
    • 5
    • 6
    • 7
    • 8
    • ...
    • 80
    • Next

    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