Sissy School (497)

MISTRESS GAIA - I GOT YOU AND YOU ARE MINE - HD

52% HD 0:10 / 12:03

MISTRESS GAIA - I GOT YOU AND YOU ARE MINE - HD

LoyalFans 10 months ago

Live With Being Bullied

54% HD 0:10 / 4:58

Live With Being Bullied

LoyalFans 2 years ago

gf's feminization, chastity, and thick cock pegging for sissy bf - full video on Veggiebabyy Manyvids

gf's feminization, chastity, and thick cock pegging for sissy bf - full video on Veggiebabyy Manyvids

xHamster 2 years ago

Elite Sissification: Transform into a High-Class Slut under Mistress Bibianne & Mistress Elena

47% HD 0:10 / 11:00

Elite Sissification: Transform into a High-Class Slut under Mistress Bibianne & Mistress Elena

LoyalFans 1 year ago

Sissy finishing school, Alice’s Final Preparation. The full movie

62% HD 0:10 / 54:42

Sissy finishing school, Alice’s Final Preparation. The full movie

LoyalFans 6 months ago

GENDER REASSIGNMENT SURGERY 1080P

HD 0:10 / 12:49

GENDER REASSIGNMENT SURGERY 1080P

LoyalFans 2 months ago

BBC University

72% HD 0:10 / 12:23

LoyalFans 1 year ago

FINISHING SCHOOL FOR ASPIRING LADIES

HD 0:10 / 18:07

FINISHING SCHOOL FOR ASPIRING LADIES

LoyalFans 3 years ago

Sissy school part 1 - Chastity training

HD 0:10 / 10:15

Sissy school part 1 - Chastity training

LoyalFans 1 year ago

Sissification And Rope Bondage For Nosey Step-Brother (wmv)

49% HD 0:32 / 26:57

Sissification And Rope Bondage For Nosey Step-Brother (wmv)

Clips4sale 1 year ago

Matriarch Ezada Sinn, Mistress Kennya and Evil Woman humiliate the sissy and lock him in permanent chastity

57% HD 0:10 / 10:26

Matriarch Ezada Sinn, Mistress Kennya and Evil Woman humiliate the sissy and lock him in permanent chastity

LoyalFans 1 year ago

Melody licks Sissi

Melody licks Sissi

xHamster 6 years ago

Babydick Diapered at School

HD 0:10 / 14:14

Babydick Diapered at School

LoyalFans 1 month ago

Secretly Fucking Your Step-Brothers Big Cock-4K

4K 0:29 / 15:43

Secretly Fucking Your Step-Brothers Big Cock-4K

Clips4sale 1 year ago

Kinky Stepmom in nylon Stockings Seduces Chaste stepson Dilon - Stepmother in Silk Japan Robe Masturbates hairy Pussy, Rubbing his Cock on Shoe High Heels, small Feet on Big Dick, Female Domination, Cum on Feet, Sensual Domination 4k

61% 4K 0:25 / 16:22

Kinky Stepmom in nylon Stockings Seduces Chaste stepson Dilon - Stepmother in Silk Japan Robe Masturbates hairy Pussy, Rubbing his Cock on Shoe High Heels, small Feet on Big Dick, Female Domination, Cum on Feet, Sensual Domination 4k

Clips4sale 4 months ago

Strut & Slut Your Stuff! (1080p)

71% HD 0:23 / 12:11

Strut & Slut Your Stuff! (1080p)

Clips4sale 9 months ago

Sissy school part 1 - Chastity training | Evilwoman, Mistress Kennya, Ezada Sinn

68% 0:31 / 10:14

Sissy school part 1 - Chastity training | Evilwoman, Mistress Kennya, Ezada Sinn

Clips4sale 1 year ago

Pervy Principal - Sissy Exposed

Pervy Principal - Sissy Exposed

Clips4sale 1 year ago

Naughty Stepnephews Harsh Punishment

60% 0:14 / 7:38

Naughty Stepnephews Harsh Punishment

Clips4sale 5 months ago

Cage and Panties til Graduation

Cage and Panties til Graduation

Clips4sale 3 years ago

Interactive BJ queen

Interactive BJ queen

Clips4sale 2 years ago

Sissy school part 2 - Mouth-fucking training - [FHD MOV]

63% 0:24 / 8:03

Sissy school part 2 - Mouth-fucking training - [FHD MOV]

Clips4sale 1 year ago

Sissy School for Sluts (720p)

HD 0:19 / 18:34

Sissy School for Sluts (720p)

Clips4sale 10 months ago

Lady Sara Borgia's Sissy School (1080p)

67% HD 0:25 / 15:27

Lady Sara Borgia's Sissy School (1080p)

Clips4sale 11 months ago

Sissy School 01: Sissy Maid, Hair, Make Up & Fashion (WMV)

63% HD 0:47 / 14:30

Sissy School 01: Sissy Maid, Hair, Make Up & Fashion (WMV)

Clips4sale 3 years ago

School Bullys Thick Cock-1080p

HD 0:28 / 11:48

School Bullys Thick Cock-1080p

Clips4sale 1 year ago

Two Sissies Captured for Lady Sara Borgia's Sissy School

55% 0:11 / 11:25

Two Sissies Captured for Lady Sara Borgia's Sissy School

Clips4sale 3 years ago

Sissy School for Sluts (1080p)

51% HD 0:19 / 18:34

Sissy School for Sluts (1080p)

Clips4sale 10 months ago

Dirty Little Secret

66% HD 0:10 / 10:49

Dirty Little Secret

LoyalFans 2 years ago

Bad Boy Turned into a Good Girl
- By the Headmistress
- Spankings, humiliations, feminization and a touch of Cane

HD 0:10 / 27:31

Bad Boy Turned into a Good Girl - By the Headmistress - Spankings, humiliations, feminization and a touch of Cane

LoyalFans 1 month ago

A sissy adventure with MistressVictoria (SISSY TRAINING) (CROSSDRESSING) (BISEXUAL ENCOURAGMENT)

64% HD 0:10 / 16:32

A sissy adventure with MistressVictoria (SISSY TRAINING) (CROSSDRESSING) (BISEXUAL ENCOURAGMENT)

LoyalFans 4 months ago

SISSY HOE SCHOOL - BBC WORSHIP

SISSY HOE SCHOOL - BBC WORSHIP

LoyalFans 5 months ago

Prissy Princess Make Up: The Prissy Princess Program 02

Prissy Princess Make Up: The Prissy Princess Program 02

Clips4sale 4 years ago

HIJABI STEP-MA GOT PREGNANT FROM STEP-SON - SISSY PAYS FOR GFE EXPENSIVE PRICE

HIJABI STEP-MA GOT PREGNANT FROM STEP-SON - SISSY PAYS FOR GFE EXPENSIVE PRICE

Clips4sale 2 years ago

Ruined & Denied: Chastity Training 05

57% HD 0:55 / 20:07

Ruined & Denied: Chastity Training 05

Clips4sale 4 years ago

You'll become a real woman and Whore for Me

55% 1:00 / 5:48

You'll become a real woman and Whore for Me

Clips4sale 8 months ago

Cuckold part 2

HD 0:10 / 13:41

LoyalFans 1 year ago

Sissy School Beginners Class Chastity (1080p)

62% HD 0:25 / 14:39

Sissy School Beginners Class Chastity (1080p)

Clips4sale 10 months ago

Turning You From A Panty Salesman Into A Panty Sissy Slut

51% HD 0:25 / 12:29

Turning You From A Panty Salesman Into A Panty Sissy Slut

Clips4sale 3 years ago

Rubberdoll sissification part 2: Rubberdoll Sissification

58% HD 0:30 / 13:47

Rubberdoll sissification part 2: Rubberdoll Sissification

Casting For Sissies

Casting For Sissies

Clips4sale 3 years ago

Welcome to Sissy School

HD 0:10 / 11:57

Welcome to Sissy School

LoyalFans 4 months ago

Sissy School: Lesson One

HD 0:28 / 10:58

Sissy School: Lesson One

Clips4sale 2 years ago

Feminization School 001:Sissy That Walk!

Feminization School 001:Sissy That Walk!

Clips4sale 1 year ago

Sissy At Work PT2 Brush The Mistress’s hair

Sissy At Work PT2 Brush The Mistress’s hair

Clips4sale 1 year ago

Little Stepbro Gets Bullied

Little Stepbro Gets Bullied

Clips4sale 2 years ago

My Humiliated Sissy Project (1080 HD)

My Humiliated Sissy Project (1080 HD)

Clips4sale 4 years ago

Three Dommes vs A Sissy Ass!

65% HD 0:10 / 16:51

Three Dommes vs A Sissy Ass!

LoyalFans 1 year ago

Mom's Bull / Your Bully: Sissy Cuck Son

Mom's Bull / Your Bully: Sissy Cuck Son

APClips 11 months ago

Ruining Your Asshole (FHD)

68% HD 0:10 / 8:34

Ruining Your Asshole (FHD)

LoyalFans 11 months ago

Hubby Pamper Punishment

51% 0:20 / 12:03

Hubby Pamper Punishment

Clips4sale 2 years ago

Outing You as a Sissy With Matron Kay & Making You Suck Our Strap-On

63% HD 0:25 / 16:30

Outing You as a Sissy With Matron Kay & Making You Suck Our Strap-On

Clips4sale 3 years ago

✨ Intro to Being a Sissy | Lesson One: Panties ✨W/ Sissy Panty Task

✨ Intro to Being a Sissy | Lesson One: Panties ✨W/ Sissy Panty Task

LoyalFans 5 months ago

Sissi anus whip - 0309

74% 0:30 / 3:11

Sissi anus whip - 0309

Clips4sale 5 months ago

New Sissy Maid Inspection And Training Stage 1 (MP4)

New Sissy Maid Inspection And Training Stage 1 (MP4)

Clips4sale 1 year ago

Sissy Sleepover | Closed Captions

28% HD 0:10 / 8:42

Sissy Sleepover | Closed Captions

LoyalFans 8 months ago

1080P I made my nerdy teacher cum inside of me MULTI CAMERA

65% 4K 0:11 / 19:20

1080P I made my nerdy teacher cum inside of me MULTI CAMERA

Clips4sale 1 year ago

Matriarch Ezada Sinn, Mistress Kennya and Evil Woman train the sissy how to suck cocks

Premium HD 8:04

Matriarch Ezada Sinn, Mistress Kennya and Evil Woman train the sissy how to suck cocks

Clips4sale 1 year ago

MISTRESS GAIA - I GOT YOU AND YOU ARE MINE - HD

47% HD 0:25 / 12:03

MISTRESS GAIA - I GOT YOU AND YOU ARE MINE - HD

Clips4sale 1 year ago

Using Sissy's Holes

61% 0:10 / 14:57

Using Sissy's Holes

Clips4sale 5 months ago

School Bully Visit-4K

4K 0:29 / 23:22

School Bully Visit-4K

Clips4sale 2 years ago

Sissy School Panty Check

61% 0:10 / 7:23

Sissy School Panty Check

Clips4sale 1 year ago

Sissi caning- 1802

Sissi caning- 1802

Clips4sale 2 years ago

Step-Sister Fucks Your Bully

HD 0:27 / 10:30

Step-Sister Fucks Your Bully

Clips4sale 3 years ago

Rubberdoll sissification & strap-on training

HD 0:10 / 25:25

Rubberdoll sissification & strap-on training

LoyalFans 3 years ago

full movie ADULT school ROLE play about a sissy slut who needs a lesson from mistress Tirza

full movie ADULT school ROLE play about a sissy slut who needs a lesson from mistress Tirza

Clips4sale 2 years ago

Sissy At Work CPT2 I - Why it so hard to use a vacuum cleaner?

Sissy At Work CPT2 I - Why it so hard to use a vacuum cleaner?

Clips4sale 1 year ago

Sissy School Advancement (720p)

HD 0:22 / 15:02

Sissy School Advancement (720p)

Clips4sale 11 months ago

Sissy in Chastity - Postural School high heels walking

67% HD 0:15 / 5:20

Sissy in Chastity - Postural School high heels walking

Clips4sale 4 years ago

Sissy Assfucks You and Diapers Too

Sissy Assfucks You and Diapers Too

Clips4sale 2 months ago

Blonde in catsuit pegging her sissy boy in school dress

61% 4K 0:14 / 12:54

Blonde in catsuit pegging her sissy boy in school dress

Clips4sale 2 years ago

Sissy Slut School: First Day - Sissy Training & Encouraged Feminization Fantasy with Femdom Mistress Mystique - WMV

Sissy Slut School: First Day - Sissy Training & Encouraged Feminization Fantasy with Femdom Mistress Mystique - WMV

Clips4sale 2 years ago

Popular Girl Trains A New Slut

Popular Girl Trains A New Slut

Clips4sale 2 years ago

Discipline in the kitchen

Discipline in the kitchen

Clips4sale 9 months ago

Headmistress & Student Eva Make You Their New Cock Sucking Sissy Slut

63% HD 0:26 / 14:59

Headmistress & Student Eva Make You Their New Cock Sucking Sissy Slut

Clips4sale 3 years ago

Day 22 Sissy training programme: Hair and makeup for sissies

HD 0:30 / 15:27

Day 22 Sissy training programme: Hair and makeup for sissies

Weekly Training for Sissies - Claim & Display, The Final Summer Assignment

Weekly Training for Sissies - Claim & Display, The Final Summer Assignment

Clips4sale 6 months ago

Sissy School : Lessons 1-5

Sissy School : Lessons 1-5

Clips4sale 1 year ago

Miela spanking - 0301

Miela spanking - 0301

Clips4sale 1 year ago

Pov Pegging Training

HD 0:29 / 12:33

Pov Pegging Training

Clips4sale 1 year ago

She Left The Silly Wannabe Hero Powerless And Humiliated In Tape Bondage! (low res mp4)

She Left The Silly Wannabe Hero Powerless And Humiliated In Tape Bondage! (low res mp4)

Clips4sale 7 months ago

Sissy Transformation - Cocksucking Practice

Sissy Transformation - Cocksucking Practice

Clips4sale 4 months ago

Sissy At Work CPT2 III - Mobile - Let’s Talk About The Prizes - 480p

Sissy At Work CPT2 III - Mobile - Let’s Talk About The Prizes - 480p

Clips4sale 1 year ago

Step-Mommy’s Your Step-Daddy Now

HD 0:10 / 10:08

Step-Mommy’s Your Step-Daddy Now

LoyalFans 1 year ago

The tawse the cane and the paddle

The tawse the cane and the paddle

Clips4sale 1 month ago

Bimbo Sissy School

Bimbo Sissy School

Clips4sale 2 years ago

STEP-SON CUCKOLDING! SCHOOL BULLY KNOCKED UP YOUR STEP-MOM

69% 4K 0:30 / 21:27

STEP-SON CUCKOLDING! SCHOOL BULLY KNOCKED UP YOUR STEP-MOM

Clips4sale 2 years ago

Sissy Bottom Slut for Valentines (HD) MP4

Sissy Bottom Slut for Valentines (HD) MP4

Clips4sale 3 years ago

Sissy At Work PT3 - Why she's so messy

Sissy At Work PT3 - Why she's so messy

Clips4sale 1 year ago

Adult school for a polish SiSSY BITCH needs lesson to behave as sissyslut and work for mistress Tirza

Adult school for a polish SiSSY BITCH needs lesson to behave as sissyslut and work for mistress Tirza

Clips4sale 2 years ago

POV Femdom: Sissy StepSon Wets Himself & Gets SPH Punished

HD 0:10 / 26:33

POV Femdom: Sissy StepSon Wets Himself & Gets SPH Punished

LoyalFans 11 months ago

4K I found stepdad giving himself wedgies with my panty

4K 0:20 / 11:00

4K I found stepdad giving himself wedgies with my panty

Clips4sale 2 years ago

School Bullys Thick Cock-720sd

HD 0:28 / 11:48

School Bullys Thick Cock-720sd

Clips4sale 1 year ago

720P I made my nerdy teacher cum inside of me MULTI CAMERA

4K 0:10 / 19:20

720P I made my nerdy teacher cum inside of me MULTI CAMERA

Clips4sale 1 year ago

Sissification And Rope Bondage For Nosey Step-Brother (high res mp4)

59% HD 0:32 / 26:57

Sissification And Rope Bondage For Nosey Step-Brother (high res mp4)

Clips4sale 1 year ago

Trained & Purged_

HD 0:52 / 13:02

Trained & Purged_

Clips4sale 4 years ago

Sissy graduation school

HD 0:18 / 13:04

Sissy graduation school

Clips4sale 4 years ago

Sissy Slut School HD

Sissy Slut School HD

Clips4sale 2 years ago

Sissification And Rope Bondage For Nosey Step-Brother (mp4)

HD 0:32 / 26:57

Sissification And Rope Bondage For Nosey Step-Brother (mp4)

Clips4sale 1 year ago

Sissy At Work PT4 Mobile - Fucked By My Louboutin Boot 480p

65% 0:15 / 9:57

Sissy At Work PT4 Mobile - Fucked By My Louboutin Boot 480p

Clips4sale 1 year ago

Humiliating The Sissy In The Closet HD 720p MP4

Humiliating The Sissy In The Closet HD 720p MP4

C4S 2 years ago

The Dick Shrink: Chastity Training 04

HD 0:50 / 14:45

The Dick Shrink: Chastity Training 04

Clips4sale 4 years ago

Strap-On Sissy Ass Maid In France - Brittany Andrews

HD 0:28 / 11:47

Strap-On Sissy Ass Maid In France - Brittany Andrews

Clips4sale 2 years ago

Sissy's first fuck POV phone

Premium HD 41:05

Sissy's first fuck POV phone

Clips4sale 1 year ago

BBC-Perverse Sissy Maid Schule 8. Lektion

BBC-Perverse Sissy Maid Schule 8. Lektion

Clips4sale 4 years ago

Hunter Wellies Sissyficating School

Hunter Wellies Sissyficating School

Clips4sale 3 years ago

BIG BLACK COCKS TAG TEAM YOUR LITTLE STEP-SISTER

55% 4K 0:28 / 10:35

BIG BLACK COCKS TAG TEAM YOUR LITTLE STEP-SISTER

Clips4sale 1 year ago

Sissy Academy

Clips4sale 3 years ago

Matriarch Ezada Sinn, Mistress Kennya and Evil Woman train the sissy to take cock up the arse

Premium HD 9:52

Matriarch Ezada Sinn, Mistress Kennya and Evil Woman train the sissy to take cock up the arse

Clips4sale 1 year ago

Sissy At Work CPT2 III - Let’s Talk About The Prizes

Sissy At Work CPT2 III - Let’s Talk About The Prizes

Clips4sale 1 year ago

STEPMOM MAKES A SISSY OUT OF YOU

HD 0:13 / 20:12

STEPMOM MAKES A SISSY OUT OF YOU

Clips4sale 4 years ago

Girl in catsuit pegging her sissy boy in school dress

57% 4K 0:14 / 12:54

Girl in catsuit pegging her sissy boy in school dress

Clips4sale 2 years ago

Feminized Sissy Just Like Step-Dad

HD 0:10 / 16:09

Feminized Sissy Just Like Step-Dad

LoyalFans 2 years ago

Sissi ass whipping 0906

Sissi ass whipping 0906

Clips4sale 2 years ago

Sissi strapping 0606

Sissi strapping 0606

Clips4sale 2 years ago

Stage 1 Chastity Challenge

Stage 1 Chastity Challenge

Clips4sale 4 years ago

Sissy Slut School

Sissy Slut School

Clips4sale 4 years ago

Sissi anus cane - 2201

Sissi anus cane - 2201

Clips4sale 4 years ago

High Protocol Slave Training by Maya Sinstress (720x 1280)

High Protocol Slave Training by Maya Sinstress (720x 1280)

Clips4sale 2 years ago

Clean Step-Mommys Cum Filled Dripping Pussy-1080p

4K 0:27 / 12:06

Clean Step-Mommys Cum Filled Dripping Pussy-1080p

Clips4sale 2 years ago

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