PornPorn Gay • US
  • Live Sex
    -50%
  • Premium Premium Videos
  • Pornstars
  • Channels
xHamsterLive Annual Ultimate: 50% OFF Our 10th b’day special

Sissy Transformation Porn Videos

Free Videos
Short Videos
Premium Videos
Photos
4K
HD
Full HD
VR
Best Videos
By clicking the content you will also see an ad. AD
  • STRAIGHT FUCKS HIS CUTE TRANS SECRETARY BAREBACK AND CUMS INSIDE HER CREAMPIE ASS
    10:24
    STRAIGHT FUCKS HIS CUTE TRANS SECRETARY BAREBACK AND CUMS INSIDE HER CREAMPIE ASS
    Dilan Castro
    79.3K views
  • From Boy to Sissy 💋 – Part 1: My Transformation and First Steps
    06:33
    From Boy to Sissy 💋 – Part 1: My Transformation and First Steps
    BECKY CROSS
    6.5K views
  • Hot Crossdresser in Female Body Suit Rubs Pussy with Dildo
    04:48
    Hot Crossdresser in Female Body Suit Rubs Pussy with Dildo
    Bailey Wilde
    12.9K views
  • Tan Pantyhose Show
    05:58
    Tan Pantyhose Show
    Dani Leg
    10.2K views
  • From Boy to Sissy - Part 1: My Transformation and First Steps
    03:29
    From Boy to Sissy - Part 1: My Transformation and First Steps
    BECKY CROSS
    4.9K views
  • The whore wants sex
    21:10
    The whore wants sex
    13dangerous
    1.8K views
  • Deep dildo in my sissy ass, would you go deeper?
    01:12
    Deep dildo in my sissy ass, would you go deeper?
    ManMoth1
    1.8K views
  • Filling my ass with 8 inch dildo
    01:51
    Filling my ass with 8 inch dildo
    ManMoth1
    1.8K views
  • Santa Fucks Sexy Tgirl
    01:33
    Santa Fucks Sexy Tgirl
    Jake Grand
    2.8K views
  • 10 inch Loki in the dirt
    01:47
    10 inch Loki in the dirt
    BabyJaan
    6.2K views
  • Hot Blonde Crossdresser Self Spankind and Smoking
    00:26
    Hot Blonde Crossdresser Self Spankind and Smoking
    Crossdresserkitty
    3K views
  • Dr. Dantee's Magic Cock Therapy: Shy Guy's Transformation
    06:12
    Dr. Dantee's Magic Cock Therapy: Shy Guy's Transformation
    The XXX Therapist
    5.1K views
  • Dr. Dantee's Magic Cock Therapy: Shy Guy's Transformation
    06:12
    Dr. Dantee's Magic Cock Therapy: Shy Guy's Transformation
    The XXX Therapist
    1K views
  • Fitness Transformation: Skinny Boy to Athletic Guy Chasing Ab 2025 New Years Resolution!
    01:58
    Fitness Transformation: Skinny Boy to Athletic Guy Chasing Ab 2025 New Years Resolution!
    Blacked_Hippie
    4.3K views
  • The Attraction Distance Technique: Transform Your Dating Life!
    01:30
    The Attraction Distance Technique: Transform Your Dating Life!
    Bighomie 20
    3.9K views
  • Which soldier owns this dick?
    01:03
    Which soldier owns this dick?
    ladyboyArmyOfficial
    2.6K views
  • Daddy transforms his thick cock into a delicious and creamy Yule log dessert.
    08:09
    Daddy transforms his thick cock into a delicious and creamy Yule log dessert.
    newatthisbutnaughty
    1.4K views
  • My Straight Friend Asks Me to Give Him Anal Until I Cum
    08:02
    My Straight Friend Asks Me to Give Him Anal Until I Cum
    Andrews Perverts
    756.1K views
  • HETERO FUCKS HIS TRANS SECRETARY BAREBACK AND CUMS INSIDE HER CREAMPIE ASS
    11:32
    HETERO FUCKS HIS TRANS SECRETARY BAREBACK AND CUMS INSIDE HER CREAMPIE ASS
    Dilan Castro
    553.4K views
  • Carnaval 2026 - Big Booty Brazilian Gets Fucked by Daddyblackxxl
    21:31
    Carnaval 2026 - Big Booty Brazilian Gets Fucked by Daddyblackxxl
    DADDYBLACKXXX
    202.2K views
  • Addicted to sucking strangers' dicks
    08:29
    Addicted to sucking strangers' dicks
    deepthroatec
    58.5K views
  • Swallowing Huge Cock Until I Drown
    06:12
    Swallowing Huge Cock Until I Drown
    Charlieduardd
    565.7K views
  • A Straight Guy Keeps Fucking My Mouth, I Just Do What He Wants
    05:08
    A Straight Guy Keeps Fucking My Mouth, I Just Do What He Wants
    deepthroatec
    117.1K views
  • A milky femboy student screams from daddy's big dick from the buzz in his ass without a condom!
    06:07
    A milky femboy student screams from daddy's big dick from the buzz in his ass without a condom!
    ArchiRusik
    1.6M views
  • Lingerie Slut Gets Fucked in Heels by 10" BBC
    36:17
    Lingerie Slut Gets Fucked in Heels by 10" BBC
    DADDYBLACKXXX
    209.9K views
  • Let Him Swallow and Endure
    05:24
    Let Him Swallow and Endure
    fullgag
    201.8K views
  • Mouth fucked mercilessly
    07:09
    Mouth fucked mercilessly
    deepthroatec
    67.4K views
  • 8 Hung Twinks Gangbang a Sissy Hardcore
    50:30
    8 Hung Twinks Gangbang a Sissy Hardcore
    FWBigDick
    779.6K views
  • My roomie likes to destroy my dirty and tight ass as deep as he can
    05:26
    My roomie likes to destroy my dirty and tight ass as deep as he can
    angeldiaz17x
    2M views
  • Amazing Anal Orgasm in Close-up Charlieduard
    05:52
    Amazing Anal Orgasm in Close-up Charlieduard
    Charlieduardd
    248.9K views
  • I FUCKED THE SLUTTIEST TRANS IN THE NEIGHBORHOOD BAREBACK, I FILLED HER HUGE ASS SWALLOWER WITH CUM. CREAMPIE
    20:53
    I FUCKED THE SLUTTIEST TRANS IN THE NEIGHBORHOOD BAREBACK, I FILLED HER HUGE ASS SWALLOWER WITH CUM. CREAMPIE
    Dilan Castro
    116.5K views
  • Wild Blowjob, Headfirst, with a Straight Guy
    05:06
    Wild Blowjob, Headfirst, with a Straight Guy
    deepthroatec
    141.7K views
  • Total Submission: Black Sissy Hole Broken and Bred by Superior BWC
    06:48
    Total Submission: Black Sissy Hole Broken and Bred by Superior BWC
    SergiaDiorSissy
    191.8K views
  • STRAIGHT MARRIED FUCKS CUTE TWINK FEMBOY AND CUMS INSIDE HER ASS ANAL CREAMPIE
    11:37
    STRAIGHT MARRIED FUCKS CUTE TWINK FEMBOY AND CUMS INSIDE HER ASS ANAL CREAMPIE
    Dilan Castro
    714.6K views
  • Lingerie Slut Gets Fucked in Heels by 10" BBC
    36:17
    Lingerie Slut Gets Fucked in Heels by 10" BBC
    DADDYBLACKXXX
    76.3K views
  • Young White Twinks Gets My Big Black Dick and Hot Creamy Cum
    01:06
    Young White Twinks Gets My Big Black Dick and Hot Creamy Cum
    Vision X Studios
    45.9K views
  • Throat Smashing 3. Cumshot
    04:06
    Throat Smashing 3. Cumshot
    fullgag
    90.3K views
  • Passionate oral sex
    08:15
    Passionate oral sex
    deepthroatec
    64.4K views
  • Huge Cumshot! Brazilian Big Booty Slut Part 2 - the Finale!
    15:34
    Huge Cumshot! Brazilian Big Booty Slut Part 2 - the Finale!
    DADDYBLACKXXX
    8K views
  • Virgin Ass Full of Cum Drenched in Daddy's Big Dick Fountains!
    08:12
    Virgin Ass Full of Cum Drenched in Daddy's Big Dick Fountains!
    Dinar
    1.9M views
  • Sexy Crossdresser kellycd2022 in black pantyhose and boots out for an afternoon drive
    01:09:49
    Sexy Crossdresser kellycd2022 in black pantyhose and boots out for an afternoon drive
    Kellycd2022
    52.5K views
  • Massive Dick Penetration Fuck
    02:52
    Massive Dick Penetration Fuck
    YungthugM
    885.5K views
  • STRAIGHT STEPDAD CUMS INSIDE HIS STEPSON'S ASS GAY CREAMPIE ANAL WITHOUT CONDOM
    17:01
    STRAIGHT STEPDAD CUMS INSIDE HIS STEPSON'S ASS GAY CREAMPIE ANAL WITHOUT CONDOM
    Dilan Castro
    92.2K views
  • Cute schoolboy cheered up with big cock and delicious cum!
    16:31
    Cute schoolboy cheered up with big cock and delicious cum!
    Dinar
    1.3M views
  • Deep, Messy & Out of Control
    07:55
    Deep, Messy & Out of Control
    deepthroatec
    56.3K views
  • A straight man fucked and poured fountains of a young Sissy Femboy !
    14:27
    A straight man fucked and poured fountains of a young Sissy Femboy !
    ArchiRusik
    781.5K views
  • The Sissy Crossdresser bareback 6!
    11:12
    The Sissy Crossdresser bareback 6!
    Jason Collins
    57.1K views
Next page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. ...
  8. 38
  9. ...
  10. 74
74
Crossdresser Transformation
Boy to Girl Transformation
Feminization Sissy Crossdressing
Crossdressing Sissy Femboy First Time
Crossdresser Feminization
Mature Crossdressers and Sissys
Boy Dressed as Girl
Cute Sissy Femboy
Femboys in Lingerie
Twink Sissy Femboy
Sissy CD
Gay Femboys Crossdressing
Crossdresser Breeding
Fem Twink Slut
Crossdresser Schoolgirl
Homemade Crossdresser Sex
Sissy Feminization
Cross Dress
Sissy Gets Fucked
Cross Dressing
Monetize your content
Become a creator
xHamster
  • About us
  • 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
Earn money with us
  • Camgirls Wanted
  • Creator Contest
  • Сontent Creators Program
© 2026 xHamster - Free porn videos.
Desktop 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