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

    Crossdresser Captions Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    You switched to shemale orientation. Do you want to keep searching in the gay section?
    Crossdresser
    Caption
    Sissy Crossdresser
    Amateur Crossdresser
    Mature Crossdresser
    Crossdresser Fucked
    Crossdresser Blowjob
    Japanese Crossdresser
    Crossdresser Sex
    Old Crossdresser
    Sissy Caption
    Crossdresser Gangbang
    Cd Crossdresser
    Crossdresser Lingerie
    Crossdresser BBC
    Crossdresser Anal
    Crossdresser Creampie
    French Crossdresser
    Beautiful Crossdresser
    Russian Crossdresser
    Best Videos
    By clicking the content you will also see an ad. AD
    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
    Crossdressing Cuck Husband gets fucked by wife's BBC Bull Lover CD Sissy Cuckold Fiona Fortune
    08:15
    Crossdressing Cuck Husband gets fucked by wife's BBC Bull Lover CD Sissy Cuckold Fiona Fortune
    Fiona Fortune
    245.9K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    Story of when daddy pimped me out. First week. Anal toy.
    08:50
    Story of when daddy pimped me out. First week. Anal toy.
    Sunaxfemiknulla
    18.3K views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.3M views
    Sissy Evolution- A Captioned Compilation
    05:53
    Sissy Evolution- A Captioned Compilation
    Tiffany Cox
    18.2K views
    POV - Straight Guy SEDUCED by Hung Blonde BWC Trans Girl - Cadence Caliber
    03:02
    POV - Straight Guy SEDUCED by Hung Blonde BWC Trans Girl - Cadence Caliber
    TS Cadence Caliber
    128.5K views
    Cuckhold gets Fucked by the Wife's Bull Fiona Fortune Sissy CD Cuck
    14:12
    Cuckhold gets Fucked by the Wife's Bull Fiona Fortune Sissy CD Cuck
    Fiona Fortune
    108.6K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.6M views
    WISH YOU HAPPY NEW YEAR 2026 GIFT FOR ALL MY FANS
    16:52
    WISH YOU HAPPY NEW YEAR 2026 GIFT FOR ALL MY FANS
    Indiansissychubby
    18.2K 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
    Sissy Brainwash Femboy Crossdresser Motivation Caption Slut
    03:13
    Sissy Brainwash Femboy Crossdresser Motivation Caption Slut
    ClosetPantyBoy
    53.9K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    777.1K views
    Sissy Juvia does some encouraging Sissyfication Training JOI
    10:08
    Sissy Juvia does some encouraging Sissyfication Training JOI
    JuviaJolie
    27K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.1M views
    Chastity Sissys Desperate Dildo Training Captivating Caption Story
    09:27
    Chastity Sissys Desperate Dildo Training Captivating Caption Story
    KiraszaSissy
    4.7K views
    Taking a straight guy home to turn him into my faggot - Elizabeth Stewart
    08:16
    Taking a straight guy home to turn him into my faggot - Elizabeth Stewart
    Elizabeth Stewart
    399.5K views
    Small White Cock Sissy creampies fleshlight
    02:53
    Small White Cock Sissy creampies fleshlight
    ItsASmallCockLife
    1.5K views
    POV housemate finds your panties and feminizes you JOI dominant trans girl
    11:53
    POV housemate finds your panties and feminizes you JOI dominant trans girl
    Holly unt
    164.9K views
    I show you my butt
    02:26
    I show you my butt
    Andreina Naty
    20.8K views

    Relevant Short videos

    Sissy Captions Waiting For Daddy Cock Feminized Crossdresser
    Sissy Captions Waiting For Daddy Cock Feminized Crossdresser
    ClosetPantyBoy
    9.1K views
    Memorable moment from "Vladasexytrans leaks from anal"
    Memorable moment from "Vladasexytrans leaks from anal"
    Vladasexytrans
    2.5K views
    Memorable moment from "Sissy Evolution- A Captioned Compilation"
    Memorable moment from "Sissy Evolution- A Captioned Compilation"
    Tiffany Cox
    1.1K views
    WISH YOU HAPPY NEW YEAR 2026 GIFT FOR ALL MY FANS | Clip 1
    WISH YOU HAPPY NEW YEAR 2026 GIFT FOR ALL MY FANS | Clip 1
    Indiansissychubby
    91 views
    Epic moment from "Chastity Sissys Desperate Dildo Training Captivating Caption Story"
    Epic moment from "Chastity Sissys Desperate Dildo Training Captivating Caption Story"
    KiraszaSissy
    535 views
    Spectacular moment from "Chastity Sissys Desperate Dildo Training Captivating Caption Story"
    Spectacular moment from "Chastity Sissys Desperate Dildo Training Captivating Caption Story"
    KiraszaSissy
    469 views
    Your Very First Time - Trans Femdom GFE with Melissa Masters
    03:40
    Your Very First Time - Trans Femdom GFE with Melissa Masters
    Melissa Masters
    366K views
    Be Mine Only Mine
    03:24
    Be Mine Only Mine
    Stripchat official
    1K views
    Many crossdressers fucked scrnrs
    01:09:02
    Many crossdressers fucked scrnrs
    1.4M views
    Vladasexytrans leaks from anal
    03:13
    Vladasexytrans leaks from anal
    Vladasexytrans
    15.5K views
    Sissy Caption - It's not gay if you dress up like a girl
    01:00
    Sissy Caption - It's not gay if you dress up like a girl
    646.7K views
    Slutt Crossdresser tells bbc cuckold story and plays it out. The bbc fucks his hot white wife
    06:52
    Slutt Crossdresser tells bbc cuckold story and plays it out. The bbc fucks his hot white wife
    MadisonCD2025
    824 views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M views
    Sissy Slutty Crossdresser with little cock  cuckold by wife and BBC BBC
    06:52
    Sissy Slutty Crossdresser with little cock cuckold by wife and BBC BBC
    MadisonCD2025
    1.1K views
    Sissy Caption - Would you give him an assjob?
    01:00
    Sissy Caption - Would you give him an assjob?
    283.6K views
    #sissyboy #sissyslut #femboy
    01:44
    #sissyboy #sissyslut #femboy
    ryan98
    2K views
    My wife told me to play this
    11:13
    My wife told me to play this
    961.5K views
    Brainwashed Feminized Sissy Using Step Moms BBC Dildo To Cum While On Her Bed
    00:41
    Brainwashed Feminized Sissy Using Step Moms BBC Dildo To Cum While On Her Bed
    ClosetPantyBoy
    18K views
    I got on Grindr got fucked and had multiple sissygasms
    04:09
    I got on Grindr got fucked and had multiple sissygasms
    OneWhoHasFun
    158.6K views
    TG Caption: Santa Brought Me a Sissy For Christmas.
    05:22
    TG Caption: Santa Brought Me a Sissy For Christmas.
    Sissy Shelby Kiss
    6.2K views
    Cum eating instructions hung tgirl eats her own cum to show you how it's done, humiliation feminization JOI
    13:19
    Cum eating instructions hung tgirl eats her own cum to show you how it's done, humiliation feminization JOI
    Holly unt
    73.3K views
    Feminized Sissy Has A Sissygasm From Huge Dildo
    00:22
    Feminized Sissy Has A Sissygasm From Huge Dildo
    ClosetPantyBoy
    49.9K views
    Persuaded into a Shemale Relationship - Part 1
    09:12
    Persuaded into a Shemale Relationship - Part 1
    1.4M views
    Play Wlth My Pussie Ass Nipples Dont Play with My Heart
    03:16
    Play Wlth My Pussie Ass Nipples Dont Play with My Heart
    Stripchat official
    3K views
    Sissy Caption - Bullied into enjoying his cock.
    01:00
    Sissy Caption - Bullied into enjoying his cock.
    486.2K views
    White Sissy Femboy Rides Big Dildo
    01:12
    White Sissy Femboy Rides Big Dildo
    JessicaLovesBBC
    2K views
    Lovely young girl is a shemale with big cock
    08:11
    Lovely young girl is a shemale with big cock
    10.5M views
    Sissy delicious
    54:38
    Sissy delicious
    Assexploringmachin
    1.5K views
    Shemale Anatomy
    03:06
    Shemale Anatomy
    2.8M views
    Brainwashed Feminized Sissy Ass Playing Dress Up Need Spanking
    00:13
    Brainwashed Feminized Sissy Ass Playing Dress Up Need Spanking
    ClosetPantyBoy
    12.1K views
    Your First Time Getting Fucked by a Trans Girl: First Date GFE POV Femdom
    06:31
    Your First Time Getting Fucked by a Trans Girl: First Date GFE POV Femdom
    Melissa Masters
    576.2K views
    sissy maid doris in action (polish language speaking with english captions)
    09:51
    sissy maid doris in action (polish language speaking with english captions)
    Dorisstar
    4.1K views
    Fucking on the last day of summer, in a cornfield
    03:39
    Fucking on the last day of summer, in a cornfield
    vika_sissy
    342.8K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Crossdresser Captions

    • Gender Transformation Captions
    • Sissy Caption Stories
    • Fuck My Ass Please Dirty Talk
    • Cd Captions
    • Turning Cuck Husband Into Faggot
    • Sissy Caption Stories BBC
    • Cum Like a Girl
    • Shemale Cumming While Fucked
    • Femboy Big Cock
    • Crossdresser Caught Fucking Dildo
    • Bi Confusion
    • Accidentally Dick Slip
    • The Sissy's Future
    • In Front of Friends
    • Straight Friend Loses Bet
    • Chicks With Dicks Compilation
    • Begging to Get Pregnant
    • Male Feminization Hentai
    • Make Him Scream
    • First Time Sex Very Hard

    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