Sissy Training (2,924)

Sissy Training - Suck and Swallow Close-up

Sissy Training - Suck and Swallow Close-up

FapHouse 2 weeks ago

IT A Latex Halloween Story Stage 3 (WMV)

66% HD 0:33 / 9:56

IT A Latex Halloween Story Stage 3 (WMV)

Clips4sale 1 week ago

Sissy Gooning training part 6

HD 0:25 / 10:11

Sissy Gooning training part 6

Clips4sale 2 weeks ago

Brenda Karter Private Show

HD 2:00 / 14:54

Brenda Karter Private Show

Flirt4Free 1 week ago

Trained for Sissy

Trained for Sissy

XHamster 4 weeks ago

Anal Training and Stretching for Good Submissives - Follow along

Anal Training and Stretching for Good Submissives - Follow along

XHamster 3 weeks ago

Bad Tinder Hookup Turns Into Sissy Pegging Session With Big Latina Boobs

Bad Tinder Hookup Turns Into Sissy Pegging Session With Big Latina Boobs

Wankado 1 week ago

Step-stepmommy's Secret Sissy (full) Sissy Slut Exposed and Punished with Femdom Pegging, Anal Fisting & Humiliating Spankings

Step-stepmommy's Secret Sissy (full) Sissy Slut Exposed and Punished with Femdom Pegging, Anal Fisting & Humiliating Spankings

XHamster 1 week ago

You're Not a Real Man! You're My Sissy Slut!

You're Not a Real Man! You're My Sissy Slut!

XHamster 6 days ago

Femdom Pegging Gangbang Slave Kassie

Femdom Pegging Gangbang Slave Kassie

XHamster 3 weeks ago

Amelia Sweety Private Show

HD 2:00 / 10:52

Amelia Sweety Private Show

Flirt4Free 2 weeks ago

Make Me Bi Stories #34: My Copper Crown and the Sissy Maid Party

HD 0:25 / 16:18

Make Me Bi Stories #34: My Copper Crown and the Sissy Maid Party

Clips4sale 1 week ago

Training sissy husband for enjoyment

Training sissy husband for enjoyment

PornoXO 4 weeks ago

Sissy Training Gushing Pantyhose Femdom Mistress POV Redhead

Sissy Training Gushing Pantyhose Femdom Mistress POV Redhead

Wankado 2 weeks ago

Amber Greyy Private Show

Amber Greyy Private Show

Camster 1 day ago

Stepmom Teaches Her Stepson Anal, and Then Takes a DP with Her Husband

61% 1:01 / 30:18

Stepmom Teaches Her Stepson Anal, and Then Takes a DP with Her Husband

FapHouse 2 weeks ago

Zoey Evans Private Show

Zoey Evans Private Show

Flirt4Free 2 weeks ago

Mistress Maxima - Sissy Training For My Bf

Mistress Maxima - Sissy Training For My Bf

WinPorn 3 weeks ago

Ruined Orgazm for Cum eating Cage Slave

Ruined Orgazm for Cum eating Cage Slave

XHamster 2 weeks ago

Sissy Gets used and milked by headmistress

Sissy Gets used and milked by headmistress

SortPorn 4 weeks ago

Hot Gilf PoV Thick Curvy Sissy Training With Nylons And Sheer Pantyhose

Hot Gilf PoV Thick Curvy Sissy Training With Nylons And Sheer Pantyhose

Wankado 2 weeks ago

Brenda Karter Private Show

HD 2:00 / 15:17

Brenda Karter Private Show

Camster 1 week ago

femdom bi sissy conditioning - anal humiliation & fisting my slave

femdom bi sissy conditioning - anal humiliation & fisting my slave

PornBox 2 weeks ago

Reven Mayers Private Show

HD 2:00 / 13:40

Reven Mayers Private Show

Flirt4Free 1 week ago

Step Mommy Catches You Wearing Panties

Step Mommy Catches You Wearing Panties

FapHouse 1 week ago

The StepMom Turned the Femboy into a Sissy — Chap Screws in Anal Stepmom Then the Femboy

The StepMom Turned the Femboy into a Sissy — Chap Screws in Anal Stepmom Then the Femboy

SortPorn 5 days ago

Domina helps serf to get fanal sexed pt2 HD

Domina helps serf to get fanal sexed pt2 HD

BigTitsLust 2 weeks ago

Sissy Chanel Has Blas Exam at Ladylena Xxl Dildo

Sissy Chanel Has Blas Exam at Ladylena Xxl Dildo

XHamster 4 weeks ago

You're a Pathetic Sissy Cuck Not Worthy of Me, Matthew

67% 0:30 / 8:43

You're a Pathetic Sissy Cuck Not Worthy of Me, Matthew

Clips 2 weeks ago

Witch Reads Your Mind and Discovers You're a Secret Sissy

65% 0:30 / 8:55

Witch Reads Your Mind and Discovers You're a Secret Sissy

Clips 2 weeks ago

Shock therapy

XHamster 3 weeks ago

Deepthroat Training for the Bitch

Deepthroat Training for the Bitch

FapHouse 2 weeks ago

Amelia Sweety Private Show

65% HD 2:00 / 6:19

Amelia Sweety Private Show

Flirt4Free 6 days ago

Femboy Sorority (5) - Toys in Femboys Ass

Femboy Sorority (5) - Toys in Femboys Ass

XHamster 3 weeks ago

IT A Latex Halloween Story Stage 1 (MP4)

HD 0:33 / 19:10

IT A Latex Halloween Story Stage 1 (MP4)

Clips4sale 3 weeks ago

Sol Monterosso Party on Oct 21, 2026 - Part 6

63% HD 2:00 / 1:13:30

Sol Monterosso Party on Oct 21, 2026 - Part 6

Flirt4Free 3 weeks ago

Brenda Karter Private Show

HD 2:00 / 15:47

Brenda Karter Private Show

Flirt4Free 3 weeks ago

SUBMISSIVE HUSBAND-She instructs her cuckold to take it to the balls!

SUBMISSIVE HUSBAND-She instructs her cuckold to take it to the balls!

XHamster 3 weeks ago

SUBMISSIVE HUSBAND-Cuck takes big knuckle dick

SUBMISSIVE HUSBAND-Cuck takes big knuckle dick

XHamster 2 weeks ago

Maid in the Making - Service Training Part1

HD 0:47 / 11:29

Maid in the Making - Service Training Part1

Clips4sale 3 weeks ago

Perverted Slave Loves Ass Fisting (MP4)

Perverted Slave Loves Ass Fisting (MP4)

Clips4sale 6 days ago

Salome Salvi Strapon Fucked by Dominafire and Mssaintlawrance Asian Femdom Lesbian Gangbang

Salome Salvi Strapon Fucked by Dominafire and Mssaintlawrance Asian Femdom Lesbian Gangbang

XHamster 3 weeks ago

Darsy Pearly Private Show

55% 4K 2:00 / 11:20

Darsy Pearly Private Show

Flirt4Free 2 weeks ago

SISSY PRISON - Prisoner Foot Servitude

SISSY PRISON - Prisoner Foot Servitude

Clips4sale 6 days ago

Ariah Stone Private Show

Ariah Stone Private Show

Camster 1 week ago

Slutty Sissy Summer

Slutty Sissy Summer

FapHouse 2 weeks ago

Sissy Slut - Dance to the Rhythm of My Single Tail - Real Time Session Recording

Sissy Slut - Dance to the Rhythm of My Single Tail - Real Time Session Recording

XHamster 2 weeks ago

Feminization Sissification Sissy Training - Dude Bangs in Anal Stepmom Then the Femboy

Feminization Sissification Sissy Training - Dude Bangs in Anal Stepmom Then the Femboy

BigTitsLust 1 week ago

Compilation of hard femdom pegging scenes with cum on chest

Compilation of hard femdom pegging scenes with cum on chest

Cumzie 4 weeks ago

SISSY PRISON - Cuckold Torment - Part 2

HD 0:28 / 15:45

SISSY PRISON - Cuckold Torment - Part 2

Clips4sale 1 week ago

Step Mommy Catches You Wearing Panties

Step Mommy Catches You Wearing Panties

XHamster 1 week ago

Strict femdom sissy training turns into intense prostate pegging session

Strict femdom sissy training turns into intense prostate pegging session

Yesvids 3 days ago

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femdom sex orgasms pegging reverse anal pegging - anal strapon tease & denial

AnalVids 1 week ago

Princess Kali and Saba

Princess Kali and Saba

FapHouse 3 weeks ago

Deepthroat Training for the Bitch

53% 1:01 / 6:44

Deepthroat Training for the Bitch

FapHouse 2 weeks ago

Long Pegging Session With My Humiliated Sissy | Mistress Kaira

HD 0:25 / 36:44

Long Pegging Session With My Humiliated Sissy | Mistress Kaira

Shopping Trip

58% HD 0:25 / 12:40

Rewarding My Best Slutty Secretary! - Sissy Training with Cum in Chastity and Pantyhose Domination with Miss Adrastea

70% HD 1:01 / 22:57

Rewarding My Best Slutty Secretary! - Sissy Training with Cum in Chastity and Pantyhose Domination with Miss Adrastea

FapHouse 6 days ago

Total Sissification & PEGGING

65% HD 0:46 / 13:38

Total Sissification & PEGGING

C4S 2 weeks ago

Latex Slut Gets Fucked by 3 Dommes with Strap-on

Latex Slut Gets Fucked by 3 Dommes with Strap-on

XHamster 1 week ago

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

XHamster 1 week ago

Sissy Training: Accept Your New Life - Blowjob Close Up POV

Sissy Training: Accept Your New Life - Blowjob Close Up POV

XHamster 3 weeks ago

Sissy Training: Turn Your Mouth Into a Pussy - Close Up POV

Sissy Training: Turn Your Mouth Into a Pussy - Close Up POV

XHamster 3 weeks ago

Playing with my toy

Playing with my toy

XHamster 6 days ago

Your Recent Serf Life 24/7 EP 4 : Chastity Release : Your Fresh Wife is a Doll - Mistresse Julia

Your Recent Serf Life 24/7 EP 4 : Chastity Release : Your Fresh Wife is a Doll - Mistresse Julia

SortPorn 1 week ago

Tonight I Push My Sissy Slut to the Next Level

HD 1:01 / 17:18

Tonight I Push My Sissy Slut to the Next Level

FapHouse 2 weeks ago

Princess Kali and Saba

Princess Kali and Saba

XHamster 3 weeks ago

You Picked My Outfit - Latex & Leather Femdom with Denied Ending

HD 1:01 / 16:18

You Picked My Outfit - Latex & Leather Femdom with Denied Ending

FapHouse 2 weeks ago

How to Play with Your Ass (standard Definition)

56% 1:01 / 16:08

How to Play with Your Ass (standard Definition)

FapHouse 1 week ago

Latex Slut Gets Fucked by 3 Dommes with Strap-on

Latex Slut Gets Fucked by 3 Dommes with Strap-on

FapHouse 1 week ago

Pegging Caged Sissy

72% HD 0:22 / 7:37

Pegging Caged Sissy

C4S 2 weeks ago

Amida Chris Party on Oct 29, 2026 - Part 3

66% 4K 2:00 / 34:10

Amida Chris Party on Oct 29, 2026 - Part 3

Flirt4Free 2 weeks ago

Micro dick sissy loser maid gets pegged by Mistress Stefany

HD 0:25 / 17:01

Micro dick sissy loser maid gets pegged by Mistress Stefany

Clips4sale 1 week ago

Ladybug Training by tnt tanita #983 pegging and rimming PT3

Ladybug Training by tnt tanita #983 pegging and rimming PT3

XHamster 2 days ago

Sissy Slut's Favourite Halloween - (teaser) - by FemBunnyKatie

Sissy Slut's Favourite Halloween - (teaser) - by FemBunnyKatie

XHamster 2 weeks ago

Your Turn to be Kaidence King

HD 0:45 / 14:45

Your Turn to be Kaidence King

Clips4sale 1 week ago

Amida Chris Party on Nov 4, 2026 - Part 3

64% 4K 2:00 / 17:21

Amida Chris Party on Nov 4, 2026 - Part 3

Flirt4Free 1 week ago

Amida Chris Party on Nov 3, 2026 - Part 7

4K 2:00 / 34:56

Amida Chris Party on Nov 3, 2026 - Part 7

Flirt4Free 1 week ago

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part 1: shut up, get plugged & cum in the vacuum - real femdom cbt- mistress julia

AnalVids 3 weeks ago

Sissy Academy - After Hours Part 5 - The Guest - Sissy Training Audio

HD 0:25 / 40:36

Sissy Academy - After Hours Part 5 - The Guest - Sissy Training Audio

Stretch Your Ass for Me

HD 1:01 / 12:26

Stretch Your Ass for Me

FapHouse 3 weeks ago

Part 1: Shut Up, Get Plugged & Cum in the Vacuum - Real Femdom CBT- Mistress Julia

Premium HD 17:56

Part 1: Shut Up, Get Plugged & Cum in the Vacuum - Real Femdom CBT- Mistress Julia

Sheer 3 weeks ago

sissy assfucking cocksucking training

sissy assfucking cocksucking training

DrTuber 3 weeks ago

FULL feminised & fucked HARD

HD 0:25 / 11:25

FULL feminised & fucked HARD

C4S 2 weeks ago

Sissy Husband BBC Training: Mistress Stellina Obscura Trains Sissy Slut with Humiliating Wedgies, Spankings, Double Anal Pegging

Sissy Husband BBC Training: Mistress Stellina Obscura Trains Sissy Slut with Humiliating Wedgies, Spankings, Double Anal Pegging

XHamster 3 weeks ago

Sissy Gets Jerked with a Ass-plug in Her Butt and Has to Drink Jizm

Sissy Gets Jerked with a Ass-plug in Her Butt and Has to Drink Jizm

PornDR 2 weeks ago

Dominafire Pegging Sissy Slut

Dominafire Pegging Sissy Slut

FapHouse 3 days ago

Sissys Little Oopsie

60% HD 0:13 / 5:38

Sissys Little Oopsie

Ariah Stone Party on Nov 3, 2026 - Part 3

4K 2:00 / 1:45:03

Ariah Stone Party on Nov 3, 2026 - Part 3

Flirt4Free 1 week ago

how u gonna make me squirt? #Lush #Domi #SexMachine #AnalPlug 💋💦👙 - Part 3

59% HD 2:00 / 5:48

how u gonna make me squirt? #Lush #Domi #SexMachine #AnalPlug 💋💦👙 - Part 3

Flirt4Free 3 weeks ago

New Sissy Maid Inspection And Training Stage 1

New Sissy Maid Inspection And Training Stage 1

Clips 1 week ago

Humiliated, Sissified And Sucking Tatiana Vex's Strap-on - Sissification and Dildo Facefucking - Wolfgang White Femdom

HD 0:25 / 23:00

Humiliated, Sissified And Sucking Tatiana Vex's Strap-on - Sissification and Dildo Facefucking - Wolfgang White Femdom

Clips4sale 2 weeks ago

SISSY TRAINING Part 3

SISSY TRAINING Part 3

Clips4sale 5 days ago

Locktober 2026 Sissy Cage Makeup Femdom Training Amateur Exclusive HD

Locktober 2026 Sissy Cage Makeup Femdom Training Amateur Exclusive HD

AveXXX 1 week ago

Findom Goddess Kate Monroe / FemDom Fetisch Chastity Keyholding Sissification Domina Mistress

Findom Goddess Kate Monroe / FemDom Fetisch Chastity Keyholding Sissification Domina Mistress

XHamster 5 days ago

What Do You Think?

What Do You Think?

FapHouse 2 days ago

Sissy Porn Mag - Miss Jessica Wood Spanks Her Naughty Sissy with Her Hand and Slipper with Otk Spanking

HD 1:01 / 10:12

Sissy Porn Mag - Miss Jessica Wood Spanks Her Naughty Sissy with Her Hand and Slipper with Otk Spanking

FapHouse 1 week ago

Sissy Academy - After Hours Part 8 - Her Name - Sissy Training Audio

HD 0:25 / 40:01

Sissy Academy - After Hours Part 8 - Her Name - Sissy Training Audio

Forest Femdom

XHamster 1 week ago

Zoey Evans Premiere Show

HD 2:00 / 10:07

Zoey Evans Premiere Show

Flirt4Free 1 week ago

Hot Moaning While Getting Pegged by Montreal Dominatrix Empress Galaxie - Wolfgang White

Hot Moaning While Getting Pegged by Montreal Dominatrix Empress Galaxie - Wolfgang White

XHamster 6 days ago

Fabienne Gets Double Penetration

Fabienne Gets Double Penetration

FapHouse 1 week ago

Isis Pouso Private Show

4K 2:00 / 25:21

Isis Pouso Private Show

Flirt4Free 4 days ago

Go Buy One, You Paying Whore!

Go Buy One, You Paying Whore!

FapHouse 1 week ago

Taking a latex female dog out for a walk 02

Taking a latex female dog out for a walk 02

Clips 1 week ago

femdom sph bi sissy conditioning for my slave in bondage

femdom sph bi sissy conditioning for my slave in bondage

AnalVids 2 days ago

A Sissy With No Autorisation to Cum &ndash_ He Cums Twice &amp_ Gets 3 Weeks Chastity | Mistress Julia

Premium HD 12:12

A Sissy With No Autorisation to Cum &ndash_ He Cums Twice &amp_ Gets 3 Weeks Chastity | Mistress Julia

XVideosRed 2 weeks ago

Anna gets Anal Fisting Training with Mistress Sophia

Anna gets Anal Fisting Training with Mistress Sophia

Clips4sale 1 week ago

Asian Mistress Dominafire Pegging Sissy

Asian Mistress Dominafire Pegging Sissy

FapHouse 3 days ago

Goddess May Turns Beta Mike Into A Chastity Locked Sissy Maid And Fucks His Ass With A BBC Strap-On: FULL VIDEO (1080p - EN sub - sissy maid - pegging - sph - anal - femdom)

HD 0:29 / 38:58

Goddess May Turns Beta Mike Into A Chastity Locked Sissy Maid And Fucks His Ass With A BBC Strap-On: FULL VIDEO (1080p - EN sub - sissy maid - pegging - sph - anal - femdom)

Clips4sale 3 days ago

Sissy Encouragement and Training

Sissy Encouragement and Training

XHamster 1 week ago

Dominafire Fucks Sissy Slut with Strapon

Dominafire Fucks Sissy Slut with Strapon

FapHouse 3 days ago

Male trainee in nylon and spandex submits to feminization tutorial by dominant instructor

Male trainee in nylon and spandex submits to feminization tutorial by dominant instructor

Yesvids 4 days ago

DESTROYING YOUR MASCULINITY ( Smartphone Version )

HD 0:34 / 11:46

DESTROYING YOUR MASCULINITY ( Smartphone Version )

Clips4sale 4 days ago

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femdom sex orgasms pegging reverse anal pegging - anal strapon tease & denial

PornBox 1 week ago

AMBERSIS SISSY HOLE TRAINING

AMBERSIS SISSY HOLE TRAINING

Eporner 5 days ago

Berlin femdom domme raw leather strapon 18-25 big ass

Berlin femdom domme raw leather strapon 18-25 big ass

AveXXX 1 day ago

Sissy Slut SPH

62% HD 0:18 / 8:28

Clips4sale 3 weeks ago

My Little Sissy Science Experiment

My Little Sissy Science Experiment

Clips4sale 2 weeks ago

a sissy with no autorisation to cum – he cums twice & gets 3 weeks chastity - mistress julia

a sissy with no autorisation to cum – he cums twice & gets 3 weeks chastity - mistress julia

AnalVids 1 week ago

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