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

    Milf Date Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Milf and Shemale
    Shemale MILF Cum
    MILF Trans Porn
    Big Ass MILF
    Sexy Trans MILF
    Porn Trans MILF
    Horny MILF Fucks
    Busty MILF Fucked
    Tranny Fucks MILF
    Milf Gets Massage
    Milf Sissy Strapon
    Crossdresser MILF Stockings
    Super Hot MILF
    Dirty Talking MILF
    Trans MILF Lesbians
    Horny Busty MILF
    Ava Addams Hottest MILF
    Horny MILF Joanna Jet
    High Class MILF
    Happy Ending MILF
    Best Videos
    By clicking the content you will also see an ad. AD
    Hot Thai ladyboy fucks guy on their first date after sucking
    07:05
    Hot Thai ladyboy fucks guy on their first date after sucking
    Ladyboy Gold
    113.6K views
    GenderFlux Grinder Fluid Date with Viktor Belmont and Shay Bares
    06:50
    GenderFlux Grinder Fluid Date with Viktor Belmont and Shay Bares
    DaringSex
    189K views
    My Chinese Date with a suprise in her panty
    18:29
    My Chinese Date with a suprise in her panty
    XMeliX
    64.9K views
    After a Failed Blind Date, Trans Roommates Share an Intimate Encounter
    11:05
    After a Failed Blind Date, Trans Roommates Share an Intimate Encounter
    hothotfilms
    15.7K views
    Ladyboystar - Memie - My First Date with the Girly Beauty Fucking Each Other
    08:12
    Ladyboystar - Memie - My First Date with the Girly Beauty Fucking Each Other
    Ladyboy Star
    107K views
    A fuck date with SIssy Lora
    06:38
    A fuck date with SIssy Lora
    129.7K views
    Date Night - BBC Cock Hardcore Pussy Creampie ( Animated )
    08:39
    Date Night - BBC Cock Hardcore Pussy Creampie ( Animated )
    J JrShic
    13.4K 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
    5.1K views
    Grindr Date with Trans Beauties Isa Laurence, Keite Fernandes for HotTS
    06:37
    Grindr Date with Trans Beauties Isa Laurence, Keite Fernandes for HotTS
    Hot TS
    92.5K views
    Blind Date with a Horny Thai Ladyboy Rnd in a Bangfest
    08:00
    Blind Date with a Horny Thai Ladyboy Rnd in a Bangfest
    TRANS in Asia
    12.3K views
    German Shemale ... Secret hotel date
    04:57
    German Shemale ... Secret hotel date
    Kim Wagner
    610.6K views
    Trans roommates hook up after a bad blind date
    26:49
    Trans roommates hook up after a bad blind date
    Trans Roommates
    64.2K views
    tranny girl surprises her date with a bulge in her pants, he doesn't care and sucks her cock and fucks her in the ass
    18:04
    tranny girl surprises her date with a bulge in her pants, he doesn't care and sucks her cock and fucks her in the ass
    onlyvidz
    136.3K views
    My first date with an Asian girl! She surprised me with a cock!
    40:25
    My first date with an Asian girl! She surprised me with a cock!
    NCPORNO
    131.4K views
    Things get wild after date with horny femboy... chilloutvr
    05:04
    Things get wild after date with horny femboy... chilloutvr
    LuxxiLunar
    36.9K views
    TrannyPros Kendall Penny Fucks on the FIRST Date!
    10:01
    TrannyPros Kendall Penny Fucks on the FIRST Date!
    Devils tgirls
    333.1K views
    TS dates Biogirl
    06:15
    TS dates Biogirl
    TS Factor
    178.5K views
    Tranny Girlfriend Gets Ready Before Big Date
    04:03
    Tranny Girlfriend Gets Ready Before Big Date
    Janice Renee
    21.4K views
    REALTGIRLS: Date Night Dungeon
    03:11
    REALTGIRLS: Date Night Dungeon
    Real Tgirls
    60.7K views
    FEMOUT XXX - Date Night With Horny Brunette Kawaii Fiona
    03:11
    FEMOUT XXX - Date Night With Horny Brunette Kawaii Fiona
    Femout
    55.6K views
    My Grindr BBC Date fucks my sissy crossdresser ass good!
    01:10
    My Grindr BBC Date fucks my sissy crossdresser ass good!
    157.9K views
    Ladyboy Rebeca Fucks Stranger in the Ass on First Date
    32:21
    Ladyboy Rebeca Fucks Stranger in the Ass on First Date
    Shemale TS Collection
    14.1K views
    First Date w Alicia Cream & Mistress Cy's House of Whorrors
    13:26
    First Date w Alicia Cream & Mistress Cy's House of Whorrors
    Cyanide Mistress Of Darkness
    114.9K views
    Getting ready for a lunch date and I couldn’t help but touch my bulge.
    01:31
    Getting ready for a lunch date and I couldn’t help but touch my bulge.
    AJ180
    2.5K views
    Monster Fucking on First Date
    08:12
    Monster Fucking on First Date
    Kaitlyn Gender
    53.2K views
    VRB Trans Rough fuck before date with Gabby Ferraz VR Porn
    06:10
    VRB Trans Rough fuck before date with Gabby Ferraz VR Porn
    VRbtrans
    67.5K views
    Futa Dating Simulator 5 Agantha Is Not a Shy Teacher She Love to Fuck and Get Fucked
    32:17
    Futa Dating Simulator 5 Agantha Is Not a Shy Teacher She Love to Fuck and Get Fucked
    Johannesgaming
    2K views
    Date in Hotel Room with a Friend
    10:40
    Date in Hotel Room with a Friend
    Milady Silvia Helena
    11.5K views
    Blonde Shemale Gives Guys a Blowjob on First Date
    11:11
    Blonde Shemale Gives Guys a Blowjob on First Date
    Shemale TS Collection
    1.5K views
    Transexual dating show
    10:08
    Transexual dating show
    Tranny Bizarre
    40.9K views
    My Handsome Futa Girlfriend Asking Me For A Date & Got Her Mobile Number to Keep in Touch Forever
    05:58
    My Handsome Futa Girlfriend Asking Me For A Date & Got Her Mobile Number to Keep in Touch Forever
    Asura
    10.5K views
    Trans Hottie Kendall Penny Gives the Ultimate Date to Lucky
    13:02
    Trans Hottie Kendall Penny Gives the Ultimate Date to Lucky
    Devils tgirls
    140.3K views
    Girl forgot to tell her Tinder date that she’s Trans
    05:31
    Girl forgot to tell her Tinder date that she’s Trans
    Medline
    33K views
    Watch Transgirl Ria Bentley Fuck Her 9" Bull on Their First Date
    01:55
    Watch Transgirl Ria Bentley Fuck Her 9" Bull on Their First Date
    Ria_Bentley
    33.8K views
    Hazelnut Latte: Got Caught Cheating and Fucking Trans in the Mouth on the First Date - Episode 2
    10:13
    Hazelnut Latte: Got Caught Cheating and Fucking Trans in the Mouth on the First Date - Episode 2
    Dirty GamesxXx
    1.5K views
    Hardcore fuck date with ts porn star Isabela Fontanelli
    10:12
    Hardcore fuck date with ts porn star Isabela Fontanelli
    TS Playground
    37.8K views
    The blind date
    08:25
    The blind date
    Sabina Apfel
    68.5K views
    TRANSFIXED - Trans Kate Zoha & Lesbian Pristine Edge's Blind Date Turns Into Hard Sex In Lingerie
    13:20
    TRANSFIXED - Trans Kate Zoha & Lesbian Pristine Edge's Blind Date Turns Into Hard Sex In Lingerie
    Transfixed
    64.2K views
    Petra,s Valentine date ❤️
    31:18
    Petra,s Valentine date ❤️
    PetraTVsletje
    21.6K views
    Super Hot Thai Ladyboy Model Found on Dating App Blows Your Mind and Your Balls
    11:00
    Super Hot Thai Ladyboy Model Found on Dating App Blows Your Mind and Your Balls
    LadyboystarVR
    10.3K views
    karla bbc grindr date
    01:29
    karla bbc grindr date
    16.7K views
    My date is in the suitcase?! Fucking my tantaly doll as soon as I arrived!
    11:44
    My date is in the suitcase?! Fucking my tantaly doll as soon as I arrived!
    Emily Adaire
    70.9K views
    HA31 Japanese student paid dates after class, with vibrator ejaculated in the car !
    01:32
    HA31 Japanese student paid dates after class, with vibrator ejaculated in the car !
    Shinoda hakumi
    60.3K views
    BLACK-TGIRLS: Date Night With Akaya Prime
    03:11
    BLACK-TGIRLS: Date Night With Akaya Prime
    Black Tgirls
    40.1K views
    romantic date night with Britney leads to sex
    08:20
    romantic date night with Britney leads to sex
    Pure Ts
    347.4K views
    Pretty tranny gets her mouth fucked by Grindr Date
    02:04
    Pretty tranny gets her mouth fucked by Grindr Date
    69.3K views
    Busty shemale throat fucking her date
    06:04
    Busty shemale throat fucking her date
    60.9K views
    • Back
    • 1
    • ...
    • 4
    • 5
    • 6
    • 7
    • 8
    • ...
    • 80
    • Next

    Searches Related to Milf Date

    • First Date
    • Meet up
    • New Young Stepmom
    • Mature Mom Step Son
    • Big Cock Shemale Fucks Girl
    • Shemale MILF
    • Best Step Mom
    • Hot Mom Anal
    • Big Ass Stepmom
    • Japanese Mom
    • Hotwife With Young
    • Moms Sex
    • 18 Year Old
    • Daddy Fucking Sissy
    • Hard Fuck
    • Wife Shares
    • Huge Cock Shemale
    • Mommy Nessie
    • Dicks Shemales
    • Step Mom Fucks Sissy

    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