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
    • 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
    ICE MELTING SALE — 50% OFF 🧊🔥 Limited-time deal
    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
    • Sissy
    • Shemale Fucks Girl
    • 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

    How To Be Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Beyonce Knowles (Be)
    Beyonce Knowles (Be)
    Subscribe
    3.2K
    Sissy
    Sissy Crossdresser
    Sissy Training
    Sissy Feminization
    Sissy BBC
    Sissy Chastity
    Sissy Husband
    Sissy Compilation
    Sissy Fucked
    Sissy Blowjob
    Amateur Sissy
    Sissy Gangbang
    Sissy Slave
    Sissy Cuckold
    Sissy Femdom
    Sissy Boy
    Sissy Slut
    Sissy Faggot
    Sissy Cum
    Submissive Sissy
    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
    2.2M views
    HOW TO BE A BETTER SISSY!
    10:42
    HOW TO BE A BETTER SISSY!
    436.6K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3.1M views
    Learning How to Be a Good Sissy
    08:12
    Learning How to Be a Good Sissy
    Pure Ts
    52.1K views
    A guide to sissication: Beginner - Am I a sissy?
    23:32
    A guide to sissication: Beginner - Am I a sissy?
    765.3K views
    Step Mommy Trains You How to Be A Sissy Cock Sucker (Humiliation)
    10:07
    Step Mommy Trains You How to Be A Sissy Cock Sucker (Humiliation)
    Jessica Bloom
    188.6K views
    How to train your sissy ass
    17:41
    How to train your sissy ass
    667.6K views
    learning how to be a good girl
    06:48
    learning how to be a good girl
    Pure Ts
    14.5K views
    CD TRAP SISSY EDUCATION TRAINING 101
    01:27:33
    CD TRAP SISSY EDUCATION TRAINING 101
    943.3K views
    I can teach you how to be a total sissy
    15:59
    I can teach you how to be a total sissy
    Sissy Instruction
    39.8K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.5M views
    You need to learn how to suck cock if you are going to be a
    08:19
    You need to learn how to suck cock if you are going to be a
    Sissy Instruction
    5.1K views
    Sissyfication
    43:09
    Sissyfication
    1.1M views
    I can teach you how to be a real sissy girl
    13:39
    I can teach you how to be a real sissy girl
    Sissy Instruction
    33K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.7M views
    If you are going to be a sissy you have to learn how to suck
    05:12
    If you are going to be a sissy you have to learn how to suck
    Sissy Instruction
    34.7K views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.3M views
    I can teach you how to be a real sissy girl
    15:18
    I can teach you how to be a real sissy girl
    Sissy Instruction
    15.1K views
    shemale dresses sissy to fuck
    16:14
    shemale dresses sissy to fuck
    2.1M views
    I will show you how to be a real sissy girl
    08:21
    I will show you how to be a real sissy girl
    Sissy Instruction
    10.4K views
    Male to female gender transformation smoking whore
    16:00
    Male to female gender transformation smoking whore
    705K views
    If you want to be a sissy you have to learn how to suck cock
    09:06
    If you want to be a sissy you have to learn how to suck cock
    Sissy Instruction
    24.6K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    2M views
    "How to be 💦 weak, obedient and hot |
    05:16
    "How to be 💦 weak, obedient and hot |
    2K views
    How to Train Your Sissy Boyfriend
    08:12
    How to Train Your Sissy Boyfriend
    Brat Perversions
    123.4K views
    I will show you how to be a real sissy
    08:13
    I will show you how to be a real sissy
    Sissy Instruction
    6.4K views
    Tv is for Sissies (Full Video)
    56:35
    Tv is for Sissies (Full Video)
    629.2K views
    You should know how to suck a cock if you are going to be a
    07:27
    You should know how to suck a cock if you are going to be a
    Sissy Instruction
    10.7K views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    2M views
    For Sissies  How to obtain past your oral fixating
    14:15
    For Sissies How to obtain past your oral fixating
    239.4K views
    Shemale Anatomy
    03:06
    Shemale Anatomy
    2.9M views
    This little bitch knows how to ride a big cock like mine.
    07:28
    This little bitch knows how to ride a big cock like mine.
    MrNastyXavier
    185.3K views
    My wife told me to play this
    11:13
    My wife told me to play this
    974.6K views
    I’m still learning how to suck a dick, he’s my first and he’s huge.
    05:43
    I’m still learning how to suck a dick, he’s my first and he’s huge.
    Calm
    84.6K views
    The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)
    07:20
    The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)
    Sonechka25
    43.1K views
    sissy How To Suck Cock
    11:30
    sissy How To Suck Cock
    241.1K views
    Trust The Fucking Process
    52:41
    Trust The Fucking Process
    1M views
    How to Swallow Your Own Cum - Sissy Training Guide
    08:54
    How to Swallow Your Own Cum - Sissy Training Guide
    Jessica Bloom
    127.9K views
    Feminization Positivity Trainer
    03:20
    Feminization Positivity Trainer
    717.8K views
    Step-Mommy Jessica Bloom Shows You How to Cum From AnalStep-Mommy Jessica Bloom Shows You How to Cum From Anal Like a Good Sissy
    05:17
    Step-Mommy Jessica Bloom Shows You How to Cum From AnalStep-Mommy Jessica Bloom Shows You How to Cum From Anal Like a Good Sissy
    linktree
    40.3K views
    Sissy Joyce - A real life sissy slave
    01:16
    Sissy Joyce - A real life sissy slave
    Sissy Joyce
    703.4K views
    Tranny Ria Bentley Shows How to Suck a 10" Massive Cock Instructional Video
    07:07
    Tranny Ria Bentley Shows How to Suck a 10" Massive Cock Instructional Video
    Ria_Bentley
    124.7K views
    My step sister turned me into her trans wife
    05:13
    My step sister turned me into her trans wife
    linktree
    112.4K views
    How To Self Suck - Yoga Training With Jessica Bloom
    09:59
    How To Self Suck - Yoga Training With Jessica Bloom
    linktree
    116K views
    Sissy Feminization
    07:42
    Sissy Feminization
    430.1K views
    Sissy Jessica Bloom Teaches You How To Suck Cock And Swallow Cum
    07:28
    Sissy Jessica Bloom Teaches You How To Suck Cock And Swallow Cum
    linktree
    61.6K views
    Sissy #2: Becoming A Cock Slut
    15:35
    Sissy #2: Becoming A Cock Slut
    879.6K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to How To Be Sissy

    • Sissy Being Used by Verbal BBC
    • Crossdresser First Time With a Man
    • Male to Female Transformation Fantasy
    • The Sissy's Future
    • Secret Sissyboy
    • Boy Dressed as Girl
    • White Femboys Are so Submissive
    • Fuck My Ass Please Dirty Talk
    • Sissification Process
    • Sissyslut
    • Degraded Sissies
    • Spinner Trans
    • Crossdress POV
    • Too Tight
    • Sissys Get Blacked
    • Tranny Leather Skirt
    • Feminization Training
    • Feminized and Fucked
    • Slut Trainer
    • Instruction for Crossdressers
    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