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 First Time Dressing Up For Daddy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Daddy
    First
    Dress
    Time
    First Time Sissy
    Sissy Dress up
    First Time Dressed
    First Time
    Sissy Daddy
    Dress up
    Daddies Sissy
    Sissy Time
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Sissy Husband
    Sissy Chastity
    Young Sissy
    Best Videos
    By clicking the content you will also see an ad. AD
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.3M views
    Step dad ask me to seduce him
    05:46
    Step dad ask me to seduce him
    Buddy rider
    6.7K views
    Daddy's Good Girl!
    08:12
    Daddy's Good Girl!
    Pure Ts
    938.3K views
    Becoming a sissy Crossdressing When nobody is home (Angel Rios's First time on cam).
    02:48
    Becoming a sissy Crossdressing When nobody is home (Angel Rios's First time on cam).
    Angel Rios
    7.8K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.6M views
    Wife let me wear her clothes and sissygasm
    06:24
    Wife let me wear her clothes and sissygasm
    OneWhoHasFun
    28.3K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3.1M views
    Sexy sissy in pink lingerie loves playing with her toys. cross dressing femboy fucks ass riding dildo
    06:21
    Sexy sissy in pink lingerie loves playing with her toys. cross dressing femboy fucks ass riding dildo
    Marcus Domes
    6.2K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.2M 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
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    1.9M views
    Trans Verbal Demands   -Elegant Look With Glove And Sweet Dress
    13:00
    Trans Verbal Demands -Elegant Look With Glove And Sweet Dress
    Syn Thetic
    68.5K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    798.4K views
    Asian femboy seeking attention in short dress
    05:06
    Asian femboy seeking attention in short dress
    Niya_cd
    10K 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
    638.7K views
    Big Butt Booty Slut Crossdresser Sissy Gay White Ass Sexy Dress
    05:26
    Big Butt Booty Slut Crossdresser Sissy Gay White Ass Sexy Dress
    Crossdresserkitty
    81K views
    dominant stepmom helps out her sissy slave
    05:59
    dominant stepmom helps out her sissy slave
    Pure Ts
    371.3K views
    White nylon Fantasy in blue polka dress
    06:32
    White nylon Fantasy in blue polka dress
    MTFXXXVIDS
    2K views
    Never Expecting to Be a Sexy Girl
    08:12
    Never Expecting to Be a Sexy Girl
    Pure Ts
    476.2K views
    Guy Decides to Dress as Woman for the First Time
    02:21
    Guy Decides to Dress as Woman for the First Time
    Bailey Wilde
    4.1K views

    Relevant Short videos

    Daddy is letting me wear panties this time!
    Daddy is letting me wear panties this time!
    Victoria Lecherri
    817 views
    Captivating moment from "Nightmare Horror Sexy Ladyboy Hot Night Dress Sexy Big Ass Booty Shemale"
    Captivating moment from "Nightmare Horror Sexy Ladyboy Hot Night Dress Sexy Big Ass Booty Shemale"
    Crossdresserkitty
    200 views
    Thrilling moment from "Nightmare Horror Sexy Ladyboy Hot Night Dress Sexy Big Ass Booty Shemale"
    Thrilling moment from "Nightmare Horror Sexy Ladyboy Hot Night Dress Sexy Big Ass Booty Shemale"
    Crossdresserkitty
    205 views
    Memorable moment from "Sexy Ladyboy Striptease Solo Performance Hot Short Dress Big Ass"
    Memorable moment from "Sexy Ladyboy Striptease Solo Performance Hot Short Dress Big Ass"
    Crossdresserkitty
    241 views
    Powerful moment from "Sexy Ladyboy Striptease Solo Performance Hot Short Dress Big Ass"
    Powerful moment from "Sexy Ladyboy Striptease Solo Performance Hot Short Dress Big Ass"
    Crossdresserkitty
    234 views
    Jaw-dropping moment from "Sexy Ladyboy Striptease Solo Performance Hot Short Dress Big Ass"
    Jaw-dropping moment from "Sexy Ladyboy Striptease Solo Performance Hot Short Dress Big Ass"
    Crossdresserkitty
    241 views
    Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    293.3K views
    Compilation of Crossdressing CD Madison who loves to dress slutty and crossdress
    07:10
    Compilation of Crossdressing CD Madison who loves to dress slutty and crossdress
    MadisonCD2025
    612 views
    Big daddy fuck 19 years old sissy
    06:34
    Big daddy fuck 19 years old sissy
    Crystal Phoenix
    125.3K views
    4K Shemale Cute Sissy Crossdresser 3 Hot Dresses White Gay Boy Slut Twink Big Butt Big Ass
    06:28
    4K Shemale Cute Sissy Crossdresser 3 Hot Dresses White Gay Boy Slut Twink Big Butt Big Ass
    Crossdresserkitty
    25.3K views
    Crossdresser shop owner gets fucked by a man in the shop
    13:00
    Crossdresser shop owner gets fucked by a man in the shop
    WanidaCrossdresser
    347.8K views
    Mom Crossdresser Madison dressing in sexy outfits with thigh high hose stockings and heels and walks around showing off teasing
    08:31
    Mom Crossdresser Madison dressing in sexy outfits with thigh high hose stockings and heels and walks around showing off teasing
    MadisonCD2025
    706 views
    I turned my straight roommate intro trans wife
    05:20
    I turned my straight roommate intro trans wife
    CutePinkUnicorn
    510.2K views
    Young sissy first time dressing
    00:47
    Young sissy first time dressing
    5.2K views
    Sissy cums too early and gets punished with rough fucking
    02:35
    Sissy cums too early and gets punished with rough fucking
    2.1M views
    Guy Decides to Dress in Drag for the First Time
    02:20
    Guy Decides to Dress in Drag for the First Time
    Bailey Wilde
    3.3K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M views
    Crossdressing tricks if you don't have a girl dresses don't worry you can make it from your own boy
    06:24
    Crossdressing tricks if you don't have a girl dresses don't worry you can make it from your own boy
    Crossdresserkitty
    5.8K views
    My stepmom is a tranny
    16:46
    My stepmom is a tranny
    Combat zone transsexual barebacking
    1.1M views
    I Receive New Boots and Walk in Them for the First Time
    01:10
    I Receive New Boots and Walk in Them for the First Time
    MicziCD
    9.6K views
    Cross Dressing Student and Tutor Playing with Each Other
    08:12
    Cross Dressing Student and Tutor Playing with Each Other
    Crossdressing Amateurs
    302.8K views
    Big Cumshot Cute Ladyboy Legs Hot Green Dress Sexy Body Pretty Style of Cumming
    06:12
    Big Cumshot Cute Ladyboy Legs Hot Green Dress Sexy Body Pretty Style of Cumming
    Crossdresserkitty
    6.9K views
    Dating a mature crossdresser
    08:12
    Dating a mature crossdresser
    Pure Ts
    241.5K views
    ladyboy naked in public with pantyhose and sandals very hot ass enjoy her
    10:11
    ladyboy naked in public with pantyhose and sandals very hot ass enjoy her
    Misaelechowski
    8.6K views
    19 year old trans fucked hard by stranger in hotel room
    05:38
    19 year old trans fucked hard by stranger in hotel room
    Crystal Phoenix
    128.5K views
    Big White Ass Sissy Crossdresser Lady Boy Purple Dress
    06:18
    Big White Ass Sissy Crossdresser Lady Boy Purple Dress
    Crossdresserkitty
    5K views
    Rented Out by His Mistress
    06:12
    Rented Out by His Mistress
    Pure Ts
    64K views
    Big White Sissy Ass Crossdresser Slut Twink Gay Fem Boy Lady Boy Emo Style Flowered Sexy Dress
    07:29
    Big White Sissy Ass Crossdresser Slut Twink Gay Fem Boy Lady Boy Emo Style Flowered Sexy Dress
    Crossdresserkitty
    10.7K views
    Male to female gender transformation smoking whore
    16:00
    Male to female gender transformation smoking whore
    695K views
    Friday flaunt
    01:25
    Friday flaunt
    Granttaylor0711
    3.9K views
    Lovely young girl is a shemale with big cock
    08:11
    Lovely young girl is a shemale with big cock
    10.6M views
    Sizzling Secretary Vibes: Kitty Stuns in a Blue Dress as the Ultimate Femboy Icon!
    06:05
    Sizzling Secretary Vibes: Kitty Stuns in a Blue Dress as the Ultimate Femboy Icon!
    Crossdresserkitty
    8.4K views
    Lily DeMure Blowjob & Doggy
    11:54
    Lily DeMure Blowjob & Doggy
    1.6M views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy First Time Dressing Up For Daddy

    • Crossdresser First Time With a Man
    • Sissy Boy for Daddy Use
    • Wife and Crossdressing Husband Make Love
    • Femboy Cum in Mouth
    • Fuck My Ass Please Dirty Talk
    • Mature Transvestite Fucked by 2 Men
    • White Femboys Are so Submissive
    • Two Crossdressers Sucking Cocks
    • Male to Female Transformation Fantasy
    • Secret Sissyboy
    • Crossdress Gangbang
    • Cross Dresser Blowjob
    • Hot Tgirl Self Facial While Analed
    • Do You Like Boys
    • Homemade Amateur Lingerie
    • Step Sister Fucks Virgin Step Brother
    • Most Beautiful Girl XXX Beauty Cute
    • Slutty Spun Shemale Blows Clouds
    • Caught Wearing Sisters Clothes
    • Giving Him an Experience

    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