Porn Porn Transgender • US
  • Live Sex
  • Premium Premium Videos
  • Categories
  • Pornstars
  • Channels
  • photos
HALLOWEEN SALE – 50% OFF! 👻🎃 Limited Time, Big Thrills!

Sissy Fun Porn Videos

4160 Results

Free Videos
Short Videos
Sissy Fun
Premium Videos
Photos
HD
A Sissy's Life
Horny Shemale Slut
Sissy-Virgin
Crossdressing Humiliation
Sweet Sissy87
Amateur Wife Sloppy Seconds
Tranny Tube TV
Slutty Stepmom
Sissyboilucy
Bimbo Doll
Naughty Girl
Extreme Heels
Prissy
Horny Slut
Teen Mistress
Sissyalicia
Sissy-Cori
Fucking Machine Bondage
Dirty Roulette
A Sissy's Purpose
Full HD
4K
VR
Best Videos
By clicking the content you will also see an ad. AD
  • Sissy Really Pleasure with BBC
    03:57
    Sissy Really Pleasure with BBC
    2.9M views
  • I Was Hired, and While Attending to the Client, I Also Had the Pleasure of Meeting His She Arrived and Caught Us in the Act
    36:16
    I Was Hired, and While Attending to the Client, I Also Had the Pleasure of Meeting His She Arrived and Caught Us in the Act
    Tsdanisantos1
    343.7K views
  • EAT SHEMALE CUM CEI TRAINER
    11:13
    EAT SHEMALE CUM CEI TRAINER
    882.7K views
  • Breaking in Another Sissy Ass for Your Viewing Pleasure.
    01:12
    Breaking in Another Sissy Ass for Your Viewing Pleasure.
    36.5K views
  • Breaking in Another Sissy Ass for Your Viewing Pleasure.
    01:12
    Breaking in Another Sissy Ass for Your Viewing Pleasure.
    25.2K views
  • Sissy #1: Accepting Your Destiny
    11:37
    Sissy #1: Accepting Your Destiny
    656.8K views
  • Emasculate your mind
    13:52
    Emasculate your mind
    616.9K views
  • Watch A Man Use His Transgender Wife For His Pleasure!
    07:34
    Watch A Man Use His Transgender Wife For His Pleasure!
    SmoleGirlTrans
    67.7K views
  • TRAIN YOUR SISSY PUSSY, BE A BUTTSLUT
    09:06
    TRAIN YOUR SISSY PUSSY, BE A BUTTSLUT
    669.2K views
  • Accept Who You Are Part 2
    03:54
    Accept Who You Are Part 2
    320.3K views
  • SISSYALINE TRAIN YOUR SISSY PUSSY
    09:06
    SISSYALINE TRAIN YOUR SISSY PUSSY
    587.2K views
  • Turned into a good girl and used for his pleasure
    08:12
    Turned into a good girl and used for his pleasure
    Pure Ts
    281K views
  • The Penalty for Theft
    09:52
    The Penalty for Theft
    Pure Ts
    76.1K views
  • Facial Fun
    07:08
    Facial Fun
    TSRyley
    16.2K views
  • Sissy Caption - Pranking your straight roommate
    00:50
    Sissy Caption - Pranking your straight roommate
    631.2K 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
    809.9K views
  • Sissy Caption - Bullied into enjoying his cock.
    01:00
    Sissy Caption - Bullied into enjoying his cock.
    567.9K views
  • Sissy Caption - He's going to pump your ass full of cum.
    01:00
    Sissy Caption - He's going to pump your ass full of cum.
    717.7K views
  • Sexy Brides Have Fun with a Double Dildo
    05:27
    Sexy Brides Have Fun with a Double Dildo
    FrinaXXX
    29.2K views
  • 2026 World Cup at Tsdanisantos-a True Pleasure and a Seductive Experience.
    34:36
    2026 World Cup at Tsdanisantos-a True Pleasure and a Seductive Experience.
    Tsdanisantos1
    166.8K views
  • How You Became A Sissy
    05:20
    How You Became A Sissy
    602.9K views
  • Krissy & Max Quiet Fun
    04:24
    Krissy & Max Quiet Fun
    Grooby_Girls
    50.4K views
  • Nyl Intense Hard Sex Tasty Hot Orgy Sweet Pleasure Buttocks Thirsty for Cock Sweet Hot Ass Fucked Intense Sex Sweet Tasty
    02:19
    Nyl Intense Hard Sex Tasty Hot Orgy Sweet Pleasure Buttocks Thirsty for Cock Sweet Hot Ass Fucked Intense Sex Sweet Tasty
    377.8K views
  • Sissy Caption - Sissy caught by roommate
    01:00
    Sissy Caption - Sissy caught by roommate
    337.7K views
  • You are a woman -sissy trainer
    04:12
    You are a woman -sissy trainer
    423.1K views
  • Sissy Caption - Why jerk off when you can become a sissy?
    01:00
    Sissy Caption - Why jerk off when you can become a sissy?
    397.8K views
  • Sissy Caption - This is who you are now, sissy.
    01:00
    Sissy Caption - This is who you are now, sissy.
    384.5K views
  • Kept by Jessica Blake Part 4
    02:12
    Kept by Jessica Blake Part 4
    Hot TS
    158.1K views
  • Degraded and bound Alina learns that her pleasure is on the secon place during exhausting bdsm session
    11:20
    Degraded and bound Alina learns that her pleasure is on the secon place during exhausting bdsm session
    alinanightsky
    459.8K views
  • Crossdresser taken in front of the window lets out hoarse moans of pleasure
    05:23
    Crossdresser taken in front of the window lets out hoarse moans of pleasure
    MTFXXXVIDS
    178.3K views
  • Fun with Gigi and Dave Archive, Tranny Girlfriend and Man Lovemaking, Another Raw Video
    17:03
    Fun with Gigi and Dave Archive, Tranny Girlfriend and Man Lovemaking, Another Raw Video
    Gigi and David
    453.3K views
  • GANGBANG FANTASY - SISSY SLUT
    03:08
    GANGBANG FANTASY - SISSY SLUT
    263.2K views
  • Anal pleasure and lots of cum
    06:06
    Anal pleasure and lots of cum
    Schokk077
    50K views
  • Sissy Caption - Would you give him an assjob?
    01:00
    Sissy Caption - Would you give him an assjob?
    335.9K views
  • Sissy Caption - Reward him for his work, sissy.
    00:58
    Sissy Caption - Reward him for his work, sissy.
    496K views
  • Amazonium Intense Anal Sex Hot Big Ass Tasty Swallows Huge Monster Cock Sweet Pleasure Tasty Intense Sex Fucked in the Ass Hot
    04:22
    Amazonium Intense Anal Sex Hot Big Ass Tasty Swallows Huge Monster Cock Sweet Pleasure Tasty Intense Sex Fucked in the Ass Hot
    619.5K views
  • He Thought He Was Just Trying on Panties for Fun
    06:32
    He Thought He Was Just Trying on Panties for Fun
    Rozebella
    71.5K views
  • Angeluka play with a Bbc
    14:48
    Angeluka play with a Bbc
    Angeluka
    84.6K views
  • Sissy Caption - Feel like helping your straight friend cum?
    01:00
    Sissy Caption - Feel like helping your straight friend cum?
    362.2K views
  • Fake Job Interview Bags a Crossdresser
    06:12
    Fake Job Interview Bags a Crossdresser
    Pure Ts
    111.3K views
  • Bobbie used by BBC!!
    07:12
    Bobbie used by BBC!!
    527.8K views
  • Trippy Sissy
    07:16
    Trippy Sissy
    202.4K views
  • an overbooked fun night
    18:48
    an overbooked fun night
    Kittykisses96
    208.3K views
  • cd sissy having fun with her boyfriend
    07:56
    cd sissy having fun with her boyfriend
    871.8K views
  • Sissy Caption - Your friends are horny, sissy.
    01:00
    Sissy Caption - Your friends are horny, sissy.
    287.4K views
  • Pretty Trap Black Pleasure
    13:08
    Pretty Trap Black Pleasure
    452.9K views
  • Sissy really pleasure with bbc - I can't have enough of this black cock  Sissy trans blow and fuck better than most women 4
    06:17
    Sissy really pleasure with bbc - I can't have enough of this black cock Sissy trans blow and fuck better than most women 4
    Rozebell
    307.9K views
Next page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. ...
  8. 41
  9. ...
  10. 80
80

Porn Related to Sissy Fun

Horny Sissy Boy
Crossdresser Leather Skirt Playing
First Sissy Orgasm
Torture Japanese Femboy
Sissygasm Sex
Kinky Girl
Sissyslut
Family Fun
Feminized Fucked
Homemade Lesbian Strapon
Sissypaula_
Sissysubkrystal
Sissy Girly Faggot
Schoolgirl Crossdresser
Your-Sissyslut
Role Play
Sensual Pegging
Sissyjay
2 Sissies Playing
Sissycdslc
Related Channels
  • #147
    Sissy Instruction
    Sissy Instruction
  • #179
    Kimberhaven
    Kimberhaven
  • #157
    The Crossdresser
    The Crossdresser
  • #59
    Brat Perversions
    Brat Perversions
  • #74
    Allmylinks
    Allmylinks
  • #409
    River Enza
    River Enza
  • #220
    Rough dildos TS
    Rough dildos TS
  • #204
    Sissy Princess
    Sissy Princess
  • View all
Monetize your content
Become a creator
xHamster
  • About us
  • Blog
  • Creator's Blog
  • Advertising
  • xHamster Awards 2025
  • SEO Specialist Job
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
U.S.C. 2257 Notice
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