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
    -50%
    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
    -60%
    Dating
    Subscriptions
    • Upload
    14 MONTHS FREE or 50% OFF LIFETIME 🎉🥂 Faphouse End-of-Year Sale
    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
    • Homemade
    • Mature
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Lipstick Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Lipstick
    Lipstick Trainer for Sissy Faggots
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Sissy Husband
    Sissy Chastity
    Young Sissy
    Sissy Fucked
    Sissy Compilation
    Amateur Sissy
    Sissy Blowjob
    Sissy Slave
    Sissy Cuckold
    Submissive Sissy
    Sissy Gangbang
    Sissy Femdom
    Sissy Faggot
    Best Videos
    By clicking the content you will also see an ad. AD
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2M views
    elegant skinny mistress with blue dress and lipstick huge cock cumshot
    02:49
    elegant skinny mistress with blue dress and lipstick huge cock cumshot
    Nadja Cox
    155K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.6M views
    Feminization Makeover - Mascara, Fake Lashes, Lipstick
    18:30
    Feminization Makeover - Mascara, Fake Lashes, Lipstick
    Bailey Wilde
    16.2K views
    Male to female gender transformation smoking whore
    16:00
    Male to female gender transformation smoking whore
    674.4K views
    Drag Queen and Woman Makeover Transformation  - Mascara, Fake Lashes, Lipstick
    19:11
    Drag Queen and Woman Makeover Transformation - Mascara, Fake Lashes, Lipstick
    Bailey Wilde
    3K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    Deep throat training in a tight black satin dress, stockings, satin opera gloves, blonde, lipstick, glasses, frustrated in chast
    04:41
    Deep throat training in a tight black satin dress, stockings, satin opera gloves, blonde, lipstick, glasses, frustrated in chast
    JessicaXD
    652 views
    I turned my straight roommate intro trans wife
    05:20
    I turned my straight roommate intro trans wife
    CutePinkUnicorn
    450.5K views
    POV sloppy double headed lipstick blowjob for big cock TGirl Lucy
    07:50
    POV sloppy double headed lipstick blowjob for big cock TGirl Lucy
    Spike Essex
    28.8K views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.2M views
    Drag Queen and Woman Putting on Lipliner and Lipstick
    09:08
    Drag Queen and Woman Putting on Lipliner and Lipstick
    Bailey Wilde
    6.1K views
    Never Expecting to Be a Sexy Girl
    08:12
    Never Expecting to Be a Sexy Girl
    Pure Ts
    447.6K views
    I was hired to serve a customer at the motel, he asked for red lipstick and black lingerie. I was pretty pissed off, and did eve
    05:43
    I was hired to serve a customer at the motel, he asked for red lipstick and black lingerie. I was pretty pissed off, and did eve
    Nathalia Fontes
    27.8K views
    Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    271.7K views
    Man and Woman Putting on Lipliner and Lipstick
    09:01
    Man and Woman Putting on Lipliner and Lipstick
    Bailey Wilde
    3.4K views
    My wife told me to play this
    11:13
    My wife told me to play this
    946.8K views
    sissy slut niclo hot red lipstick waiting sex on bed
    04:52
    sissy slut niclo hot red lipstick waiting sex on bed
    19K views
    dominant stepmom helps out her sissy slave
    05:59
    dominant stepmom helps out her sissy slave
    Pure Ts
    342.5K views
    Lipstick and lashes
    02:17
    Lipstick and lashes
    35.1K views
    Teaching a Fag his place
    13:47
    Teaching a Fag his place
    Kimberhaven
    797.3K views
    New Sissy Crossdresser Lara White putting lipstick, make up on cute face, sexy body. Hot Femboy, shemale, tranny.
    02:30
    New Sissy Crossdresser Lara White putting lipstick, make up on cute face, sexy body. Hot Femboy, shemale, tranny.
    LaraWhiteSissy
    9.8K views
    Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
    08:12
    Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
    nbnabunny
    1.6M views
    Crossdresser and Woman Putting on Lipliner and Lipstick
    09:00
    Crossdresser and Woman Putting on Lipliner and Lipstick
    Bailey Wilde
    2.2K views
    How to Train Your Sissy Boyfriend
    08:12
    How to Train Your Sissy Boyfriend
    Brat Perversions
    91.5K views
    Nikkimontero - London tgirl mirror fun with a good lipstick
    01:10
    Nikkimontero - London tgirl mirror fun with a good lipstick
    Nikki Montero
    3.3K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    706.7K views
    FreeView Pure Red Lipstick Sissy Giving  a Blow Job
    00:32
    FreeView Pure Red Lipstick Sissy Giving a Blow Job
    5.6K views
    Daddy's Good Girl!
    08:12
    Daddy's Good Girl!
    Pure Ts
    883.3K views
    EXTREME NIPPLE PIERCING RED LIPSTICK SISSY BLONDE PIGTAILS P
    04:18
    EXTREME NIPPLE PIERCING RED LIPSTICK SISSY BLONDE PIGTAILS P
    10.3K views
    Many crossdressers fucked scrnrs
    01:09:02
    Many crossdressers fucked scrnrs
    1.4M views
    Sissy Way of Life Crossdresser Lifestyle Femboy Mindset Shemale Mindfuck Tranny Brainwash Make up Lipstick Fetish
    05:32
    Sissy Way of Life Crossdresser Lifestyle Femboy Mindset Shemale Mindfuck Tranny Brainwash Make up Lipstick Fetish
    LaraWhiteSissy
    6.4K views
    Sydney Summers and Princess Emmy Give Up On Men
    13:14
    Sydney Summers and Princess Emmy Give Up On Men
    hothotfilms
    1.4M views
    Lady Alice compilation 03 big dildo and deepthroat and glamour fetish session. lingerie, pantyhose, high heels, lipstick
    06:18
    Lady Alice compilation 03 big dildo and deepthroat and glamour fetish session. lingerie, pantyhose, high heels, lipstick
    Mesmeriza
    5.4K views
    My step sister turned me into her trans wife
    05:13
    My step sister turned me into her trans wife
    CutePinkUnicorn
    75.1K views
    Ruin this lipstick
    00:26
    Ruin this lipstick
    Zoeycdgirl
    2.2K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.2M views
    Lara White Sissy putting lipstick. Crossdresser. Cross. Transvestite. Femboy. Tgirl. Trap. Trans. Shemale.
    00:33
    Lara White Sissy putting lipstick. Crossdresser. Cross. Transvestite. Femboy. Tgirl. Trap. Trans. Shemale.
    LaraWhiteSissy
    2.7K views
    Suck It Down Smoking JOI
    06:27
    Suck It Down Smoking JOI
    Darkfetish2k
    6.4K views
    EXTREME NIPPLE PIERCING RED LIPSTICK SISSY BLONDE PIGTAILS S
    00:12
    EXTREME NIPPLE PIERCING RED LIPSTICK SISSY BLONDE PIGTAILS S
    2.5K views
    Two Sexy Sissy Do Deep Throat BlowJob
    08:25
    Two Sexy Sissy Do Deep Throat BlowJob
    IskraElectrical49
    103.4K views
    ALLXTREME NIPPLE PIERCING RED LIPSTICK SISSY BLONDE PIGTAILS
    00:55
    ALLXTREME NIPPLE PIERCING RED LIPSTICK SISSY BLONDE PIGTAILS
    1.8K views
    Dating a mature crossdresser
    08:12
    Dating a mature crossdresser
    Pure Ts
    199.7K views
    Petite TS Babe Jerks off in Fishnets & Red Lipstick Eris Jolie
    14:14
    Petite TS Babe Jerks off in Fishnets & Red Lipstick Eris Jolie
    Eris Jolie
    91K views
    shemale dresses sissy to fuck
    16:14
    shemale dresses sissy to fuck
    2M views
    Brunette ladyboy with red lipstick gets fucked by a stud in
    06:38
    Brunette ladyboy with red lipstick gets fucked by a stud in
    Extreme Ladyboys
    140.1K views
    Sucking and Jerking Each Other off Until Completion
    06:36
    Sucking and Jerking Each Other off Until Completion
    Crossdressing Amateurs
    245.8K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Lipstick

    • Sissy Mouth
    • Lipstick Fetish
    • Crossdresser Makeup
    • Crossdressing Slut
    • Tranny Swallow Cum
    • Sexy CD Stephanie
    • Sissy Pimped Out
    • Trap Fuck Tumblr
    • Femboy Makeup
    • Heavy Make up Trannies
    • Beautiful Teen Trans
    • Very Old Tranny Blowjob Cum Swallow
    • Pink Lingerie Crossdresser
    • Nylon Sam
    • Shemale Makeup
    • Jen Phantasy
    • Kissing Lipstick
    • Dirty and Kinky Crossdressers
    • Drag Queen
    • Sissycross Anna

    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 - 2025, 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