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
    • Black
    • Big Cock
    • 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
    • Black
    • Big Cock
    • Shemale Fucks Shemale
    • Amateur
    • Shemale Fucks Girl
    • Sissy
    • 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

    First Date With A Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy Transformation
    Sissy Panties
    Sissy POV
    Sissy Bukkake
    French Sissy
    Sissy Orgasm
    Sissy Whore
    Sissy Public
    Sissy Swallow
    Sissy Mistress
    Sissy Dominated
    Sissy School
    Sissy Spanking
    Cute Sissy
    Sissy Fisting
    Sissy Bnwo
    Sissy Orgy
    Sissy Moaning
    Sissy Story
    First BBC
    Best Videos
    By clicking the content you will also see an ad. AD
    NEW TEENY TRANNY TS-Emily Adaire FIRST ANAL CREAMPIE
    10:44
    NEW TEENY TRANNY TS-Emily Adaire FIRST ANAL CREAMPIE
    linktree
    207.7K views
    GenderX - Trans Hottie Casey Kisses Fucks On First Date
    12:54
    GenderX - Trans Hottie Casey Kisses Fucks On First Date
    GenderX
    145.6K 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
    FapHouse
    174.9K 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
    1.1K views
    Getting fucked for the first time
    01:25
    Getting fucked for the first time
    84K views
    first date right in the ass fucked tranny shows lover what a hard cock is
    17:58
    first date right in the ass fucked tranny shows lover what a hard cock is
    onlyvidz
    55.9K views
    2 femboys with puffy nipples make love
    04:27
    2 femboys with puffy nipples make love
    4M views
    Blonde Skinny Ladyboy Fucked Anally Outdoors on First Date
    08:12
    Blonde Skinny Ladyboy Fucked Anally Outdoors on First Date
    FapHouse
    1.3K views
    Cross Dressing Student and Tutor Playing with Each Other
    08:12
    Cross Dressing Student and Tutor Playing with Each Other
    Crossdressing Amateurs
    309.8K views
    Big Tranny fucks guy Dustin on first date
    02:00
    Big Tranny fucks guy Dustin on first date
    Trans 500
    73.1K views
    the PERFECT sissy TRAP gf YES
    17:36
    the PERFECT sissy TRAP gf YES
    1.5M views
    Cute Trannys Sex on the First Date
    22:13
    Cute Trannys Sex on the First Date
    83.4K views
    Shemale Anatomy
    03:06
    Shemale Anatomy
    2.8M views
    Crossdressing Cindy getting ready for her first date
    01:16
    Crossdressing Cindy getting ready for her first date
    Cindylov
    2K views
    Straight First Time Explode in Sissy Mouth
    08:34
    Straight First Time Explode in Sissy Mouth
    linktree
    741.2K views
    Daddy and Tina first date
    02:59
    Daddy and Tina first date
    11.4K views
    Lap Dance & Anal With Tgirl Stripper ABRIDGED
    09:54
    Lap Dance & Anal With Tgirl Stripper ABRIDGED
    Adam Castle
    385.4K views
    Asian tranny New in a first date fucking adventure
    02:04
    Asian tranny New in a first date fucking adventure
    Trans 500
    27.9K views
    Daddy Milks Trans Girl Prostate
    05:06
    Daddy Milks Trans Girl Prostate
    Gray Perrier
    348.8K views
    Date night with a granny tranny wife!
    11:39
    Date night with a granny tranny wife!
    Victoria Lecherri
    8.7K views

    Relevant Short videos

    Powerful moment from "First date with a pretty French trans girl, she sucks me and swallows in the kitchen."
    Powerful moment from "First date with a pretty French trans girl, she sucks me and swallows in the kitchen."
    Kern Ostrova
    996 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
    1.6K views
    Iconic moment from "Tgirl Riley anally used and pleasured on a first date"
    Iconic moment from "Tgirl Riley anally used and pleasured on a first date"
    Tgirl Riley
    1.5K views
    Key moment from "Tgirl Riley anally used and pleasured on a first date"
    Key moment from "Tgirl Riley anally used and pleasured on a first date"
    Tgirl Riley
    951 views
    Our First Date
    Our First Date
    Cassandra Lovit
    439 views
    Powerful moment from "I never wear panties on a first date"
    Powerful moment from "I never wear panties on a first date"
    cd_aysemmm
    211 views
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    29:33
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    FapHouse
    2.6M views
    Date in Hotel Room with a Friend
    10:40
    Date in Hotel Room with a Friend
    Milady Silvia Helena
    11.7K views
    Another straight guy getting tricked by this hot tgirl
    26:17
    Another straight guy getting tricked by this hot tgirl
    1.1M views
    Emily's First Day with A Stange Lesbian Woman _ Dating Sex : Futanari Affairs
    09:19
    Emily's First Day with A Stange Lesbian Woman _ Dating Sex : Futanari Affairs
    Asura
    12K views
    GenderX - Wife Wants Husband To Fuck Her Trans Friend
    12:54
    GenderX - Wife Wants Husband To Fuck Her Trans Friend
    GenderX
    2.7M views
    Date Night with Mature Crossdresser
    08:12
    Date Night with Mature Crossdresser
    Pure Ts
    217.8K views
    Lily DeMure Blowjob & Doggy
    11:54
    Lily DeMure Blowjob & Doggy
    1.6M views
    Ria Bentley Gets Impregnated by Her 10" Bull Date
    21:12
    Ria Bentley Gets Impregnated by Her 10" Bull Date
    FapHouse
    211.5K views
    shemale dresses sissy to fuck
    16:14
    shemale dresses sissy to fuck
    2.1M 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
    172.1K views
    Teaching a Fag his place
    13:47
    Teaching a Fag his place
    Kimberhaven
    826.8K views
    Sissy Doll Fucking in a Pegging Date
    07:00
    Sissy Doll Fucking in a Pegging Date
    FapHouse
    19.1K views
    I fuck my stepmom's friend when she's at her house
    07:02
    I fuck my stepmom's friend when she's at her house
    yesid
    482.9K views
    Humiliating Date Story by a Pathetic Piggy
    14:11
    Humiliating Date Story by a Pathetic Piggy
    FapHouse
    18.5K views
    Fuck my throat as hard as possible as deep as you can, daddy
    05:51
    Fuck my throat as hard as possible as deep as you can, daddy
    missangell_
    156.5K views
    Sexy Tgirl shoots a lot of cum while getting fucked bare on date #5
    01:02:22
    Sexy Tgirl shoots a lot of cum while getting fucked bare on date #5
    Tgirl Riley
    152.1K views
    Sexy CD Fucks Cute White Guy
    12:27
    Sexy CD Fucks Cute White Guy
    439K views
    Tgirl Riley getting fucked bare in Date #6 PartII
    55:16
    Tgirl Riley getting fucked bare in Date #6 PartII
    Tgirl Riley
    166.1K views
    Fake Job Interview Bags a Crossdresser
    06:12
    Fake Job Interview Bags a Crossdresser
    Pure Ts
    39.7K views
    Gina ́s New Year's Date
    09:40
    Gina ́s New Year's Date
    Strapsex
    114.3K views
    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
    124.8K views
    When you feel horny, try dating a crossdresser like me.
    11:25
    When you feel horny, try dating a crossdresser like me.
    WanidaCrossdresser
    41.2K views
    Anna russian shemale suck cock outdoor
    07:07
    Anna russian shemale suck cock outdoor
    135.3K views
    Dating a Guy, I'm the Only One in the Camera.
    02:50
    Dating a Guy, I'm the Only One in the Camera.
    Taiwancdgirl
    19.6K views
    Surprise! She has a cock!
    00:49
    Surprise! She has a cock!
    308.7K views
    German amateur teen shemale get anal fuck in bathroom homemade
    12:54
    German amateur teen shemale get anal fuck in bathroom homemade
    Transen-von-Nebenan
    706.5K views
    Sissy's first fuck on video
    06:39
    Sissy's first fuck on video
    152.8K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to First Date With A Sissy

    • Perverted
    • Don't Tell
    • Taboo
    • Crazy Trannys
    • Uncensored
    • Humiliated
    • Transvestite Restaurant
    • Stiffie Surprise Under Dress
    • Beautiful Ladyboys Rapid Erection
    • Tight Dresses
    • Degraded
    • Drag Queen Show Drag Queen Show
    • Permanent Sissification
    • Used Hard
    • Relentless Pounding
    • Eye Contact
    • Trailer Park Trash
    • Bisexual Confusion
    • Femme Girls
    • Miss Lonely Kitty
    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