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 Preparation Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.6M views
    Sissy Preparation
    00:47
    Sissy Preparation
    littlemissbrat
    15K 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
    The bitch was tied up and prepared for ass fucking
    16:40
    The bitch was tied up and prepared for ass fucking
    IskraElectrical49
    178.1K views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    1.9M views
    Vlogmas #2: I'm preparing a special photoshoot for Christmas - Veronica Sanders
    05:32
    Vlogmas #2: I'm preparing a special photoshoot for Christmas - Veronica Sanders
    Veronica Sanders
    8.6K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.1M views
    A tempting secretary changed her stocking after work and inserted anal plug without panty to prepare for the secret nightwork.
    13:59
    A tempting secretary changed her stocking after work and inserted anal plug without panty to prepare for the secret nightwork.
    Harinni
    6.3K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M views
    A horny slut with perfect body in tight dress and black pantyhose tries new sex toys alone and prepares to go out.
    14:30
    A horny slut with perfect body in tight dress and black pantyhose tries new sex toys alone and prepares to go out.
    Harinni
    13.2K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    A naughty college girl with big tits cut off her underwear, put on a leash with chain on her neck and prepared for school.
    09:05
    A naughty college girl with big tits cut off her underwear, put on a leash with chain on her neck and prepared for school.
    Harinni
    19.1K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    789.9K views
    Teen Sisiy, who is still preparing for the landlord to pay the rent on her new house, stretches her ass with a dildo
    05:52
    Teen Sisiy, who is still preparing for the landlord to pay the rent on her new house, stretches her ass with a dildo
    Usaberilx
    3.1K views
    Never Expecting to Be a Sexy Girl
    08:12
    Never Expecting to Be a Sexy Girl
    Pure Ts
    473K views
    I prepared a little gift for the pizza boy
    05:07
    I prepared a little gift for the pizza boy
    cd_aysemmm
    4K views
    Dating a mature crossdresser
    08:12
    Dating a mature crossdresser
    Pure Ts
    238.2K views
    Pampering In Satin Nightwear - just preparing for further use
    02:03
    Pampering In Satin Nightwear - just preparing for further use
    Chantal Fouet
    70.3K views
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    29:33
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    Ria_Bentley
    2.5M views
    Preparing for cum eating
    01:00
    Preparing for cum eating
    Dockanlatex
    21.9K views
    Daddy Milks Trans Girl Prostate
    05:06
    Daddy Milks Trans Girl Prostate
    Gray Perrier
    330.9K views

    Relevant Short videos

    Sissy prepare for Daddy
    Sissy prepare for Daddy
    lovecrossdresserlove
    4.5K views
    Preparing before a big dick date
    Preparing before a big dick date
    Karpenter_S
    1.9K views
    Washing my boipussy. Preparing for a date.
    Washing my boipussy. Preparing for a date.
    JennaTraveler
    1.8K views
    Getting ready and prepared to go see Daddy!
    Getting ready and prepared to go see Daddy!
    Victoria Lecherri
    1.3K views
    Emotional moment from "A horny slut with perfect body in tight dress and black pantyhose tries new sex toys alone and prepares to go out."
    Emotional moment from "A horny slut with perfect body in tight dress and black pantyhose tries new sex toys alone and prepares to go out."
    Harinni
    995 views
    Spectacular moment from "A horny slut with perfect body in tight dress and black pantyhose tries new sex toys alone and prepares to go out."
    Spectacular moment from "A horny slut with perfect body in tight dress and black pantyhose tries new sex toys alone and prepares to go out."
    Harinni
    910 views
    Mister A prepares Clara's ass and gets sucked
    06:49
    Mister A prepares Clara's ass and gets sucked
    ClaraBCBG
    29.7K 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
    Sissy Prepares For A Good Night
    08:51
    Sissy Prepares For A Good Night
    Alyssa Mercury
    6.3K views
    Tgirls Closeup Cumshot Compilation for Sissy
    25:07
    Tgirls Closeup Cumshot Compilation for Sissy
    3.4M views
    Hot Sissy Brenda Prepares Dinner for You
    10:22
    Hot Sissy Brenda Prepares Dinner for You
    hotsissybrenda
    13.9K views
    Shemale Anatomy
    03:06
    Shemale Anatomy
    2.8M views
    Trans Christmas Elf Prepares Magic Candies for Santa Jessica Bloom
    11:21
    Trans Christmas Elf Prepares Magic Candies for Santa Jessica Bloom
    Jessica Bloom
    6.9K views
    dominant stepmom helps out her sissy slave
    05:59
    dominant stepmom helps out her sissy slave
    Pure Ts
    369.2K views
    Sissy Slut Michelle in a New Lingerie Preparing Before a Date in a Hotel of Turkish Bodrum
    28:30
    Sissy Slut Michelle in a New Lingerie Preparing Before a Date in a Hotel of Turkish Bodrum
    Michael Ernandes
    4.8K views
    Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    291.2K views
    Girl prepares to fuck sissy hard
    00:43
    Girl prepares to fuck sissy hard
    Sissy Joyce
    21.8K views
    I turned my straight roommate intro trans wife
    05:20
    I turned my straight roommate intro trans wife
    CutePinkUnicorn
    506.6K views
    TVMandySpencer showing off like a slut and preparing for a fucking.
    02:19
    TVMandySpencer showing off like a slut and preparing for a fucking.
    TvMandySpencer
    11K views
    Picking up a Sexy Tgirl off the Streets and Giving Her My BBC
    08:12
    Picking up a Sexy Tgirl off the Streets and Giving Her My BBC
    TGIRLPLAYHOUSE
    2.3M views
    Amateur  Beautiful Transgender Femboi Prepare Herself to Have you Inside
    16:04
    Amateur Beautiful Transgender Femboi Prepare Herself to Have you Inside
    Madam_Denise
    3.6K views
    He filled my ass with it, his drips a lot
    07:53
    He filled my ass with it, his drips a lot
    Piou_Sissy
    249.2K views
    Preparation of the comic book "Pink's story"
    02:23
    Preparation of the comic book "Pink's story"
    Do_and_co_art
    9.4K views
    I had a big cumshot in unkown hotel
    05:39
    I had a big cumshot in unkown hotel
    Samantha Sissy World
    1.5M views
    Katya Prepares His Ass in the Middle of the Night for Future Guys
    01:21
    Katya Prepares His Ass in the Middle of the Night for Future Guys
    Dimedrol01
    2.7K views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.3M views
    Preparing the food
    14:43
    Preparing the food
    g geraldinelonginlove
    4.5K 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
    636.6K views
    WOW - Carola Smit - preparation lots of extreme stretching
    03:21
    WOW - Carola Smit - preparation lots of extreme stretching
    3.4K views
    Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
    44:10
    Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
    alinanightsky
    233.7K views
    Dick craving denver shoemakers prepares for the real thing
    04:24
    Dick craving denver shoemakers prepares for the real thing
    15.5K views
    Sissy Femboy Fucked From Behind
    05:20
    Sissy Femboy Fucked From Behind
    2.7M views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Preparation

    • Sissy Femboy Fucked
    • Traps Femboys and Sissys
    • Sissygasm Training
    • Hot Crossdresser Cums Chastity
    • Sissification Process
    • Sissy Femboy Extreme
    • A Sissy's Purpose
    • Crossdressing Caught Dressed
    • Trap in Lingerie
    • Femdom Feminization
    • Anal Trans BDSM
    • Feminized Husband Turned Into Slave
    • Femboys and Sissys
    • Transvestites Sissies
    • Sisy Boy
    • Submissive Tranny
    • Sissykanisa
    • Crossdresser Rough
    • Tied to Bed
    • Feminine Ladyboy

    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