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

    Romantic Sissy Affair Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Romantic
    Affair
    Romantic Sissy
    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
    Anal Sex - Romantic Fuck with an incredible French Trans Girl, i cum inside her.
    21:16
    Anal Sex - Romantic Fuck with an incredible French Trans Girl, i cum inside her.
    Kern Ostrova
    115.8K views
    Gorgeous petite Tranny girl sucks cock with a passion, gets verbal and kinky
    03:18
    Gorgeous petite Tranny girl sucks cock with a passion, gets verbal and kinky
    JsseMontz
    126K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.1M views
    Sucking some dudes cock while my boyfriend is at work
    05:18
    Sucking some dudes cock while my boyfriend is at work
    JsseMontz
    563.5K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.6M views
    Slutty trans girl sucks a straight college guy with a HUGE BBC in a hotel.
    07:20
    Slutty trans girl sucks a straight college guy with a HUGE BBC in a hotel.
    JsseMontz
    32.5K views
    Sensual Shower with a Transgender Goddess - Hard Fist Anal & Sucking
    11:15
    Sensual Shower with a Transgender Goddess - Hard Fist Anal & Sucking
    Maxime horns
    137.7K views
    Turning a straight man into a passive little whore by passionately fucking him with my big cock
    06:15
    Turning a straight man into a passive little whore by passionately fucking him with my big cock
    DotadaSP
    1.4M views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.3M views
    Trans Girl Stroking in Pantyhose - Lazy Afternoon Pleasure
    05:36
    Trans Girl Stroking in Pantyhose - Lazy Afternoon Pleasure
    Medi Voi
    22.1K views
    Brunette makes love
    02:37
    Brunette makes love
    815.7K views
    I cock worshipped some dudes huge cock on his birthday
    08:43
    I cock worshipped some dudes huge cock on his birthday
    JsseMontz
    81.3K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    Josie Blade all the good stuff
    31:14
    Josie Blade all the good stuff
    Josie Blade
    390.5K views
    How A Real Transgender Masseuse Works
    13:02
    How A Real Transgender Masseuse Works
    FantasyMassageOfficial
    1.4M views
    I'm Full of Passion
    05:10
    I'm Full of Passion
    Evehamphy
    115.5K views
    Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    291.2K views
    Sensual Sex with His Gorgeous Trans-wife - Facial
    07:18
    Sensual Sex with His Gorgeous Trans-wife - Facial
    Melodyfluffington
    272.9K views
    shemale dresses sissy to fuck
    16:14
    shemale dresses sissy to fuck
    2.1M views
    A passionate beauty was very excited by a BIG COCK
    30:59
    A passionate beauty was very excited by a BIG COCK
    Adultunes
    312.2K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    788.3K views

    Relevant Short videos

    Would You Suck Me Passionately?
    Would You Suck Me Passionately?
    jiannalust
    4.4K views
    passionate riding
    passionate riding
    Juahlovely
    2.9K views
    Femboy Cums on Stockings
    Femboy Cums on Stockings
    mothplayboy
    2.4K views
    Sensual dance
    Sensual dance
    Freshbunz
    2.9K views
    Blowjob Is One Of The Most Intimate Thing
    Blowjob Is One Of The Most Intimate Thing
    Lola Femme
    1.3K views
    Red Passion
    Red Passion
    Athena Apollonia
    796 views
    Sissy Maid Is so Sensual and Sexy
    07:42
    Sissy Maid Is so Sensual and Sexy
    Pure Ts
    7.8K views
    Never Expecting to Be a Sexy Girl
    08:12
    Never Expecting to Be a Sexy Girl
    Pure Ts
    473K views
    The best and most sensual orgasm from a tranny
    10:28
    The best and most sensual orgasm from a tranny
    yourprettykate
    61.9K views
    Trans lovers
    29:46
    Trans lovers
    Ladyboy Paradise
    162.1K views
    Intimate Gentle Toy Fuck
    09:38
    Intimate Gentle Toy Fuck
    PrincessKitti3
    45.7K views
    TransSensual Sexy Hunk Fucks His TS Girlfriend
    10:01
    TransSensual Sexy Hunk Fucks His TS Girlfriend
    Transsensual
    397.9K views
    Passion, P N P , and interracial
    07:43
    Passion, P N P , and interracial
    Rayrayto420
    48.3K views
    Sissyfication
    43:09
    Sissyfication
    1M views
    Massaging Brown Sunbathing Futa led To Romantic Anal Creampie
    10:48
    Massaging Brown Sunbathing Futa led To Romantic Anal Creampie
    Asura
    37.4K views
    dominant stepmom helps out her sissy slave
    05:59
    dominant stepmom helps out her sissy slave
    Pure Ts
    369.2K views
    Trans Audio Porn 1 - Sensual, Erotic, Asmr Jerk off with Me
    04:28
    Trans Audio Porn 1 - Sensual, Erotic, Asmr Jerk off with Me
    Gray Perrier
    3.8K views
    INTIMATE SEXTAPE WITH A GORGEOUS FRENCH TRANS WOMAN WHO FUCKS ME AND GETS FILLED
    11:38
    INTIMATE SEXTAPE WITH A GORGEOUS FRENCH TRANS WOMAN WHO FUCKS ME AND GETS FILLED
    Maxime horns
    150.4K views
    Ladyboy in intimate rodeo she bounces and keeps you well inside her
    05:14
    Ladyboy in intimate rodeo she bounces and keeps you well inside her
    MTFXXXVIDS
    7.2K views
    Sloppy blowjob and intense penetration with a FRENCH trans goddess
    08:36
    Sloppy blowjob and intense penetration with a FRENCH trans goddess
    Maxime horns
    148.1K views
    Trans Girl Sensual Ejaculation
    03:23
    Trans Girl Sensual Ejaculation
    CaliFauna
    139.3K views
    Male to female gender transformation smoking whore
    16:00
    Male to female gender transformation smoking whore
    693.8K views
    Cute Ladyboy Moaning While Getting Fucked Hard in her Sissy Ass
    08:11
    Cute Ladyboy Moaning While Getting Fucked Hard in her Sissy Ass
    Veronica Sanders
    247.3K views
    Making Out & Kissing FEMBOY Eros Orisha and Her BBC POP OUT from Under Her Skirt
    08:42
    Making Out & Kissing FEMBOY Eros Orisha and Her BBC POP OUT from Under Her Skirt
    K KirkRyner
    150.6K views
    Mamou with Loren Aprile Part 2: Shivers and Trembling Before a Passionate Fuck
    15:12
    Mamou with Loren Aprile Part 2: Shivers and Trembling Before a Passionate Fuck
    Mamou5891
    38.6K views
    Intense Passionate Kissing & Makeout Foreplay on Date Night with this GORGEOUS Black Trans Girl Eros Orisha
    08:13
    Intense Passionate Kissing & Makeout Foreplay on Date Night with this GORGEOUS Black Trans Girl Eros Orisha
    K KirkRyner
    166.1K views
    Would You Suck Me Passionately?
    04:40
    Would You Suck Me Passionately?
    jiannalust
    29.9K views
    husband bends over and fucks the femboy
    05:07
    husband bends over and fucks the femboy
    Diamond Wolfie
    262.5K views
    Romantic Date with a Client
    13:52
    Romantic Date with a Client
    Stripchat official
    58.7K views
    Girl forgot to tell her Tinder date that she’s Trans
    07:22
    Girl forgot to tell her Tinder date that she’s Trans
    JsseMontz
    634.4K views
    Sissy Femboy personal intimate solo bedroom scene
    02:06
    Sissy Femboy personal intimate solo bedroom scene
    Viper Fierce
    17.6K views
    I turned my straight roommate intro trans wife
    05:20
    I turned my straight roommate intro trans wife
    CutePinkUnicorn
    505.2K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Romantic Sissy Affair

    • Crossdresser First Time With a Man
    • Wife and Crossdressing Husband Make Love
    • Shemale Seduces Straight Guy
    • Femboy Cumming While Fucked
    • Cross Dressing Sissy Loses His Virginity
    • Romantic Trans Sex
    • Seduced in Hotel
    • Secret Sissyboy
    • Femboys Kissing
    • Homemade Seduction
    • Beautiful Lady Boy
    • Amateur Traps
    • Feminine Boys
    • Men Dressed as Women
    • Tranny Surprises Her Date
    • Two Crossdressers Cum Kisses
    • Ladyboy Threesome
    • Ladyboys Surprise
    • Male to Female Transformation Fantasy
    • Crossdress Blackmail

    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