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 Date Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Date
    First Date With a Sissy
    Ts Trap Sissy Date Hike
    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
    Sissy Gangbang
    Submissive Sissy
    Sissy Femdom
    Best Videos
    By clicking the content you will also see an ad. AD
    Transsexual Date Ends Up In The Bed
    06:13
    Transsexual Date Ends Up In The Bed
    48.9K views
    Date in Hotel and Cum
    03:02
    Date in Hotel and Cum
    Milady Silvia Helena
    9.1K views
    GenderX - Hot Blonde Gives Date His First Trans Experience
    11:56
    GenderX - Hot Blonde Gives Date His First Trans Experience
    GenderX
    94.3K views
    ADULT TIME - Pristine Edge Begs For More As Her Trans Date Goes To TOWN ON HER PUSSY!
    13:02
    ADULT TIME - Pristine Edge Begs For More As Her Trans Date Goes To TOWN ON HER PUSSY!
    AdultTime
    144K views
    MILF Love Spa Date Demo - a Futa Who Gets Blown by Glasses MILF
    11:12
    MILF Love Spa Date Demo - a Futa Who Gets Blown by Glasses MILF
    Gameland77
    just added
    Cinthia Piu: Sheila Dantas and Cinthia Piu Discover Transsexual Pleasures in Coffee Date Twist
    08:12
    Cinthia Piu: Sheila Dantas and Cinthia Piu Discover Transsexual Pleasures in Coffee Date Twist
    MMM100 TS
    5.2K views
    Hot Blonde Big Tit Shemale Gets Anal Fucked by Strangers on Their First Date
    17:46
    Hot Blonde Big Tit Shemale Gets Anal Fucked by Strangers on Their First Date
    Shemale TS Collection
    1.2K views
    Getting to Know Each Other - Closely! Fucking on the First Date
    00:41
    Getting to Know Each Other - Closely! Fucking on the First Date
    Emily Adaire
    8.4K views
    Daddy date night part 2
    00:55
    Daddy date night part 2
    78.3K views
    Hardcore Date with a Bored Student Ladyboy
    08:00
    Hardcore Date with a Bored Student Ladyboy
    TRANS in Asia
    4.6K views
    My first date with Adele, part 4...
    01:34
    My first date with Adele, part 4...
    76K views
    Jammi Cummings on Grindr date gone wild
    23:03
    Jammi Cummings on Grindr date gone wild
    17.3K views
    She fucks on first date
    26:13
    She fucks on first date
    105.1K views
    Latina Ladyboy From Tinder Date Fucked in Tight Asshole Outdoors
    23:31
    Latina Ladyboy From Tinder Date Fucked in Tight Asshole Outdoors
    Shemale TS Collection
    1.6K views
    Futa Dating Simulator 6 Gloria Is a Lawyer Who Love Fucking but Not Getting Fucked
    28:36
    Futa Dating Simulator 6 Gloria Is a Lawyer Who Love Fucking but Not Getting Fucked
    Johannesgaming
    1.1K views
    MissRose TS - The Unexpected WILD Shemale eXXXperience - Lady In Black After Dinner Date - Her Big Surprise Cumshot HOT
    03:36
    MissRose TS - The Unexpected WILD Shemale eXXXperience - Lady In Black After Dinner Date - Her Big Surprise Cumshot HOT
    MissRose TS
    29.1K views
    OOPSIE - We Had An Amazing Bisexual Threesome In An Empty Movie Theater Room During A Throuple Date
    10:05
    OOPSIE - We Had An Amazing Bisexual Threesome In An Empty Movie Theater Room During A Throuple Date
    AdultTime
    13.6K views
    VRBTRans Hot Date With Alyssa And Her Naughty Sex Games
    06:01
    VRBTRans Hot Date With Alyssa And Her Naughty Sex Games
    VRbtrans
    97.9K views
    fuck with a date
    00:34
    fuck with a date
    37.8K views
    Crossdresser Getting Ready for Date with Hot Man
    01:25
    Crossdresser Getting Ready for Date with Hot Man
    Bailey Wilde
    53.4K views

    Relevant Short videos

    Ria Bentley Gets Impregnated by Her 10" Bull Date
    Ria Bentley Gets Impregnated by Her 10" Bull Date
    Ria_Bentley
    6.2K views
    Sissy cuckold Delilah humping pillows while her wife is dating
    Sissy cuckold Delilah humping pillows while her wife is dating
    Delilah Quint
    11.2K views
    Must-see moment from "German anal tranny date outdoor on holiday in Mallorca"
    Must-see moment from "German anal tranny date outdoor on holiday in Mallorca"
    EroCom
    2.3K views
    Cum after Date
    Cum after Date
    Katha Vika
    2.5K views
    Emotional moment from "Tgirl Riley anally used and pleasured on a first date"
    Emotional moment from "Tgirl Riley anally used and pleasured on a first date"
    Tgirl Riley
    1.5K views
    Let's play before our date!
    Let's play before our date!
    Cassandra Lovit
    581 views
    Dakota: Speed Date: Mind If I..
    02:58
    Dakota: Speed Date: Mind If I..
    Iamtrantastic
    18.4K views
    After the date ended
    02:14
    After the date ended
    Nancy Rose
    8K views
    Hot Anal Date With Gorgeous Ts Foxxy And With
    04:51
    Hot Anal Date With Gorgeous Ts Foxxy And With
    9.2K views
    Guy Fucks Blonde Skinny Shemale on First Date Outdoors
    26:04
    Guy Fucks Blonde Skinny Shemale on First Date Outdoors
    Shemale TS Collection
    898 views
    Futa Dating Simulator 11 Ava Is a Prison Bitch Will She Fuck You or Will You Fuck Her
    32:17
    Futa Dating Simulator 11 Ava Is a Prison Bitch Will She Fuck You or Will You Fuck Her
    Johannesgaming
    1.2K views
    Shemale humping her male date at home
    07:07
    Shemale humping her male date at home
    10.8K views
    Going Over 9 Date with Mai
    10:55
    Going Over 9 Date with Mai
    Johannesgaming
    3.6K views
    Fantasy Dating: The Girl With The Cock Between Her Legs Part 1
    11:12
    Fantasy Dating: The Girl With The Cock Between Her Legs Part 1
    Dirty GamesxXx
    680 views
    TrannyPros Candy Marie Wants to Fuck her Man B4 Date Night!
    10:01
    TrannyPros Candy Marie Wants to Fuck her Man B4 Date Night!
    Devils tgirls
    101.1K views
    Following a Disappointing Blind Date, Trans Roommates Connect in a Passionate Moment
    13:05
    Following a Disappointing Blind Date, Trans Roommates Connect in a Passionate Moment
    hothotfilms
    3.2K views
    Going Over 8 Riley and Jane Hit It off so Well They Went on VR Date
    39:55
    Going Over 8 Riley and Jane Hit It off so Well They Went on VR Date
    Johannesgaming
    1.6K views
    Futa Dating Simulator 2 Tina Have the Biggest Cock Ive Ever Seen.
    25:12
    Futa Dating Simulator 2 Tina Have the Biggest Cock Ive Ever Seen.
    Johannesgaming
    1.2K views
    Futa Dating Simulator 10 Jessica Is Really a Tough One She Just Dont Want to Give in but I Did Fuck Her
    30:52
    Futa Dating Simulator 10 Jessica Is Really a Tough One She Just Dont Want to Give in but I Did Fuck Her
    Johannesgaming
    1.3K views
    Tinder date with shemale!
    34:56
    Tinder date with shemale!
    SweetOlivia
    55.8K views
    SHEMALE DATE NIGHT
    01:29
    SHEMALE DATE NIGHT
    134K views
    TGIRLS XXX - Jade Nyxxx Looking For A Date To Get Fucked
    03:11
    TGIRLS XXX - Jade Nyxxx Looking For A Date To Get Fucked
    Tgirls
    8.7K views
    Horny Big Titted Tranny Fucked in Her Tight Asshole on Their First Date
    08:12
    Horny Big Titted Tranny Fucked in Her Tight Asshole on Their First Date
    Shemale TS Collection
    970 views
    Date With A Posh Tranny
    24:25
    Date With A Posh Tranny
    47.3K views
    Beautiful trans Chanel Santini rides cock on the first date
    06:15
    Beautiful trans Chanel Santini rides cock on the first date
    Transsensual
    120K views
    Lexx stripping for CL date
    01:50
    Lexx stripping for CL date
    31.7K views
    GenderX - Casey Kisses Tied Up & Fucked On First Date
    12:48
    GenderX - Casey Kisses Tied Up & Fucked On First Date
    GenderX
    32.8K views
    Hot date with Hollie 2
    01:00
    Hot date with Hollie 2
    13.4K views
    Blonde Big Tit Tranny Teen Giselly Gets Fucked by Tinder Date
    24:09
    Blonde Big Tit Tranny Teen Giselly Gets Fucked by Tinder Date
    Shemale TS Collection
    2.9K views
    Blonde Skinny Tranny Outdoor From Tinder Date Anal Fucked
    28:45
    Blonde Skinny Tranny Outdoor From Tinder Date Anal Fucked
    Shemale TS Collection
    568 views
    TransSensual Casey Kisses Tops her Blind Date's Butthole
    10:01
    TransSensual Casey Kisses Tops her Blind Date's Butthole
    Transsensual
    81.3K views
    Two hot shemales having a romantic date.
    12:25
    Two hot shemales having a romantic date.
    43.8K views
    White tranny and her black date having some fun
    09:20
    White tranny and her black date having some fun
    5.2K views
    • Back
    • 1
    • ...
    • 5
    • 6
    • 7
    • 8
    • 9
    • ...
    • 80
    • Next

    Searches Related to Sissy Date

    • Lossing Virginity
    • Trap Cutie
    • Trans Stepsister
    • Surprise Throatpie
    • Pantyhose Couple
    • Lot Lizard Trucker
    • Dirty Slut
    • Triple XXX Private Full Movie
    • Friends Sleepover
    • Trailer Park Trash
    • Streetwalker
    • Trick
    • Non Passable Crossdressers
    • Filthy
    • Sneaky
    • Melbourne Aussie Sluts
    • Lovers of Transexual 01
    • First Time
    • Watching Porn Together
    • Wedding Day

    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