Sissy Instructions (102,327)

The best and newest sissy instructions videos

Monroe Fox Begs Her New Bull to Fuck Her Better Than Her Cuckold Ever Did

Monroe Fox Begs Her New Bull to Fuck Her Better Than Her Cuckold Ever Did

XHamster 1 year ago

Reena Sky Brings a Black Stud Home for Her Cuckold to See

64% HD 1:01 / 33:15

Reena Sky Brings a Black Stud Home for Her Cuckold to See

FapHouse 2 months ago

The Biggest Sissy Load and Snowball

52% HD 0:15 / 13:49

The Biggest Sissy Load and Snowball

IWantClips 2 years ago

Tia Cyrus Has a Cuckold That Just Wants to Watch

Tia Cyrus Has a Cuckold That Just Wants to Watch

XHamster 10 months ago

Kate Rhoades Private Show

57% 4K 2:00 / 10:43

Kate Rhoades Private Show

Flirt4Free 11 months ago

Size Queen Sissy Boy Training with CEI

Size Queen Sissy Boy Training with CEI

XHamster 2 months ago

Soft Cock Training By Doctor Nicole (Prone Masturbation JOI)

Soft Cock Training By Doctor Nicole (Prone Masturbation JOI)

Clips4sale 10 months ago

Nazanin Hunter Private Show

53% HD 2:00 / 8:38

Nazanin Hunter Private Show

Flirt4Free 3 years ago

Hazel Moore Decides She Likes Black Dick Better Than Her White Cuckold Husband's

Hazel Moore Decides She Likes Black Dick Better Than Her White Cuckold Husband's

XHamster 2 weeks ago

Electra Joness Party on Apr 13, 2026 - Part 3

58% 4K 2:00 / 1:00:15

Electra Joness Party on Apr 13, 2026 - Part 3

Flirt4Free 6 months ago

Allie Addison Has Always Had a Dream for Her Husband to Turn Into a Cuckold. Her Husband Gets a Snowball Full of Cum.

Allie Addison Has Always Had a Dream for Her Husband to Turn Into a Cuckold. Her Husband Gets a Snowball Full of Cum.

XHamster 1 month ago

NEW - Training You to Suck Cock So I Can Whore You Out, Phillip

71% HD 0:10 / 9:20

NEW - Training You to Suck Cock So I Can Whore You Out, Phillip

LoyalFans 2 months ago

Bi Humiliation & Cum Clean up with a Female Audience

51% 1:01 / 8:42

Bi Humiliation & Cum Clean up with a Female Audience

FapHouse 1 year ago

Gina Valentina's Cuckold Brings Home a Famous Artist and She Wants to Fuck Him While Her Cuckold Watches

Gina Valentina's Cuckold Brings Home a Famous Artist and She Wants to Fuck Him While Her Cuckold Watches

XHamster 5 months ago

Amai Liu Tells Her Cuckold Suck Together to Stay Together

Amai Liu Tells Her Cuckold Suck Together to Stay Together

XHamster 4 days ago

Sissy Cum Bucket Training: Arse fucked by Matriarch Ezada Sinn with his own cum as lube

66% HD 0:25 / 15:04

Sissy Cum Bucket Training: Arse fucked by Matriarch Ezada Sinn with his own cum as lube

Clips4sale 2 months ago

Natalie Monroe's Cuckold Faces the Small Sad Truth

Natalie Monroe's Cuckold Faces the Small Sad Truth

XHamster 3 months ago

Callie Cobra's Cuckold Never Has What It Takes to Go the Distance

Callie Cobra's Cuckold Never Has What It Takes to Go the Distance

XHamster 11 months ago

Reena Sky Brings a Black Stud Home for Her Cuckold to See

59% HD 0:39 / 33:15

Reena Sky Brings a Black Stud Home for Her Cuckold to See

FapHouse 2 months ago

Sissified and pegged - Ebony Goddess Luna Law humiliates, teases and turns this chastity slave into a sissy slut, takes pictures of her and gives her a hot pegging ounding against the window, Female Domination, Sissy Slut training, Strap-on

HD 0:17 / 13:16

Sissified and pegged - Ebony Goddess Luna Law humiliates, teases and turns this chastity slave into a sissy slut, takes pictures of her and gives her a hot pegging ounding against the window, Female Domination, Sissy Slut training, Strap-on

Clips4sale 1 month ago

Humiliating Tasks for Diaper Sissies! POV Instructions

73% HD 0:51 / 16:14

Humiliating Tasks for Diaper Sissies! POV Instructions

Clips4sale 11 months ago

Sissy feminization, anal training, CEI cum eating instruction (Arya Grander) - FemDom

Sissy feminization, anal training, CEI cum eating instruction (Arya Grander) - FemDom

XHamster 2 months ago

Bella Brookz Private Show

50% HD 2:00 / 44:00

Bella Brookz Private Show

Flirt4Free 3 years ago

Brittney Banxxx, Only Wants to Hear, "as You Wish", From Her Cuckold

Brittney Banxxx, Only Wants to Hear, "as You Wish", From Her Cuckold

XHamster 7 months ago

Eden Adams Has a Cuckold That Is Broke, so Now He Has to Pay in a Different Way

62% HD 1:01 / 27:43

Eden Adams Has a Cuckold That Is Broke, so Now He Has to Pay in a Different Way

FapHouse 7 months ago

Bella Brookz Private Show

52% HD 2:00 / 11:32

Bella Brookz Private Show

Flirt4Free 3 years ago

you'll do anything for Me! remastered: A POV with Matriarch Ezada Sinn

62% HD 0:11 / 14:57

you'll do anything for Me! remastered: A POV with Matriarch Ezada Sinn

Clips4sale 1 year ago

Your roomate makes you her slut (Femdom anal joi, assplay,ass fingering, feminization) - Sammy altham

Your roomate makes you her slut (Femdom anal joi, assplay,ass fingering, feminization) - Sammy altham

XHamster 3 months ago

Bella Brookz Private Show

56% HD 2:00 / 16:09

Bella Brookz Private Show

Flirt4Free 3 years ago

You're Now A Girl Like Me | Female POV JOI [MP4 Format]

You're Now A Girl Like Me | Female POV JOI [MP4 Format]

Clips4sale 8 months ago

Jen Holly Private Show

55% HD 2:00 / 8:35

Jen Holly Private Show

Flirt4Free 1 year ago

The bed squeaks cuckold

The bed squeaks cuckold

XHamster 1 month ago

Avery Cristy's cuckold surprise

Avery Cristy's cuckold surprise

XHamster 2 months ago

Bella Brookz Private Show

49% HD 2:00 / 5:11

Bella Brookz Private Show

Flirt4Free 2 years ago

Cuckold saw his lovely wife gagging on a humongous black dick

Cuckold saw his lovely wife gagging on a humongous black dick

XHamster 2 months ago

Ares & Adara Private Show

48% HD 2:00 / 20:07

Ares & Adara Private Show

Flirt4Free 2 years ago

Red Lips Tease and Pussyplay

61% 4K 2:00 / 10:06

Red Lips Tease and Pussyplay

Flirt4Free 3 years ago

Big-dicked sissy takes it up the ass and swallows his own cum

Big-dicked sissy takes it up the ass and swallows his own cum

XXXShake 3 years ago

Bella Brookz Private Show

66% HD 2:00 / 4:24

Bella Brookz Private Show

Camster 3 years ago

Mommy Encouragement CEI

Mommy Encouragement CEI

Eporner 9 months ago

Sissy feminization, anal training, CEI cum eating instruction (Arya Grander) - FemDom

Sissy feminization, anal training, CEI cum eating instruction (Arya Grander) - FemDom

XHamster 1 month ago

Ciara Bunny Private Show

Ciara Bunny Private Show

Camster 3 days ago

Chelsea Fost Private Show

55% 4K 2:00 / 4:24

Chelsea Fost Private Show

Camster 5 days ago

Kate England Hot Wife Cuckolding and Gives Husband a Snowball

Kate England Hot Wife Cuckolding and Gives Husband a Snowball

XHamster 4 weeks ago

Roommate transformed you in a sissy and fucked your virgin ass with a strap on (FEMINIZATION

Roommate transformed you in a sissy and fucked your virgin ass with a strap on (FEMINIZATION

PornoXO 1 year ago

Valexie Lux Private Show

58% 4K 2:00 / 5:23

Valexie Lux Private Show

Flirt4Free 1 month ago

Lily LaBeau Get That Cock Wet

64% HD 0:39 / 38:13

Lily LaBeau Get That Cock Wet

FapHouse 4 years ago

Sissy Squeeze & Drip Masturbation Instructions

66% HD 0:10 / 20:53

Sissy Squeeze & Drip Masturbation Instructions

LoyalFans 1 year ago

Time out: Diapered and Tormented 720

52% HD 0:22 / 15:03

Time out: Diapered and Tormented 720

Clips4sale 3 years ago

Sissy Anal JOI

63% HD 0:39 / 7:41

FapHouse 2 years ago

Christie Nelson's Cuckold Has Reached Rock Bottom

HD 0:39 / 35:57

Christie Nelson's Cuckold Has Reached Rock Bottom

FapHouse 1 week ago

Nadia Nash Gives Her Cuckold a Dark Chocolate Treat

68% HD 0:39 / 41:37

Nadia Nash Gives Her Cuckold a Dark Chocolate Treat

FapHouse 2 months ago

Squirting Right at You!

67% HD 2:00 / 40:51

Squirting Right at You!

Flirt4Free 14 years ago

Sissy Wife Gets Facefucked with a Strapon POV

Sissy Wife Gets Facefucked with a Strapon POV

FapHouse 3 years ago

Jhanne Cherry Private Show

52% HD 2:00 / 8:21

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Alexa Grace Has a Cuckold That Is Curious, but When He Starts to Complain She Puts That Black Cock Right in His Mouth

53% HD 1:01 / 25:56

Alexa Grace Has a Cuckold That Is Curious, but When He Starts to Complain She Puts That Black Cock Right in His Mouth

FapHouse 9 months ago

Scarlett Fay's Cuckold Knows She Will Always Come Home

Scarlett Fay's Cuckold Knows She Will Always Come Home

XHamster 6 months ago

Jen Holly Private Show

53% HD 2:00 / 4:27

Jen Holly Private Show

Flirt4Free 1 year ago

Hailey Roses Private Show

57% HD 2:00 / 5:25

Hailey Roses Private Show

Flirt4Free 3 years ago

Nazanin Hunter Private Show

49% HD 2:00 / 19:16

Nazanin Hunter Private Show

Flirt4Free 2 years ago

Striptease, full nude, masturbation, tit play and ending with a deep blowjob - Part 2

61% HD 2:00 / 4:53

Striptease, full nude, masturbation, tit play and ending with a deep blowjob - Part 2

Flirt4Free 2 years ago

Betty Sandra Private Show

Betty Sandra Private Show

Flirt4Free 3 years ago

Nazanin Hunter Members-Only Show

HD 2:00 / 24:35

Nazanin Hunter Members-Only Show

Flirt4Free 2 years ago

Fallon West Gives Her Cuckold a Snowball He Will Not Forget

Fallon West Gives Her Cuckold a Snowball He Will Not Forget

XHamster 2 months ago

Strip Me Down and Tease My Pussy

70% HD 2:00 / 4:23

Strip Me Down and Tease My Pussy

Flirt4Free 3 years ago

Coralyn Jewel Private Show

58% HD 2:00 / 16:09

Coralyn Jewel Private Show

Flirt4Free 3 years ago

Suck my cock, sissy slut! - Sissy Training with Strap-On and Jerk Off Instruction with Miss Adrastea

HD 0:10 / 13:33

Suck my cock, sissy slut! - Sissy Training with Strap-On and Jerk Off Instruction with Miss Adrastea

LoyalFans 3 months ago

Spanish Quick masturbation challenge for submissive masochists. Can you overcome it?

Spanish Quick masturbation challenge for submissive masochists. Can you overcome it?

XHamster 2 years ago

Katherine Dominates Your Cock

Katherine Dominates Your Cock

Flirt4Free 9 years ago

My Bull Called, He Wants Us Both to Prepare Our Asses

61% HD 0:39 / 19:18

My Bull Called, He Wants Us Both to Prepare Our Asses

FapHouse 10 months ago

Elizabeth Whiler Private Show

52% HD 2:00 / 13:22

Elizabeth Whiler Private Show

Flirt4Free 4 years ago

Earn My Fuck

HD 2:00 / 13:52

Flirt4Free 8 years ago

Aubrey & Isabella Private Show

Aubrey & Isabella Private Show

Flirt4Free 1 year ago

Betty Sandra Private Show

65% HD 2:00 / 5:02

Betty Sandra Private Show

Flirt4Free 2 years ago

Bi confusion sissy cock sucking trainer POV cum on face (whispers positive instructions no insults)

Bi confusion sissy cock sucking trainer POV cum on face (whispers positive instructions no insults)

Fapcat 4 years ago

Emily & Stesha Private Show

54% 4K 2:00 / 8:48

Emily & Stesha Private Show

Flirt4Free 10 months ago

INEEDAMOMMY IPOD Gentle GF Sushii turns you into slutty diaper girl

INEEDAMOMMY IPOD Gentle GF Sushii turns you into slutty diaper girl

Clips4sale 4 years ago

Sissy Swallows Eight Loads of Bull Cum [Full HD]

Premium 4K 13:08

Sissy Swallows Eight Loads of Bull Cum [Full HD]

Clips4sale 4 months ago

Viky & Mateo Private Show

57% HD 2:00 / 19:22

Viky & Mateo Private Show

Flirt4Free 9 months ago

Greisy & Rey Private Show

58% HD 2:00 / 35:48

Greisy & Rey Private Show

Flirt4Free 6 years ago

Avery Cristy's cuckold surprise

61% HD 1:01 / 31:10

Avery Cristy's cuckold surprise

FapHouse 4 years ago

Homewrecker Puts You At Her Mercy JOI

Homewrecker Puts You At Her Mercy JOI

Wankoz 4 years ago

Diapers and Cummies for Me!

Diapers and Cummies for Me!

BigTitsLust 5 months ago

Gina Valentina's Cuckold Brings Home a Famous Artist and She Wants to Fuck Him While Her Cuckold Watches

Gina Valentina's Cuckold Brings Home a Famous Artist and She Wants to Fuck Him While Her Cuckold Watches

XHamster 3 months ago

JOI with sexy blonde

JOI with sexy blonde

Some.Porn 1 year ago

Tight Pussies on Fucking Cum Swallowing Eating

54% 0:39 / 2:02:17

Tight Pussies on Fucking Cum Swallowing Eating

FapHouse 1 month ago

Viky & Mateo Private Show

56% HD 2:00 / 11:13

Viky & Mateo Private Show

Flirt4Free 9 months ago

Alison Rey taking big black cock

Alison Rey taking big black cock

XHamster 2 months ago

Nicole Ferrera's Cuckold Takes Her to Dinner but Soon He Realizes Cock Is on His Menu

51% HD 1:01 / 21:09

Nicole Ferrera's Cuckold Takes Her to Dinner but Soon He Realizes Cock Is on His Menu

FapHouse 5 months ago

Jada Doll Received a Meaty Black Dick and Then She Spit All the Cum in Her Cuckold's Mouth

Jada Doll Received a Meaty Black Dick and Then She Spit All the Cum in Her Cuckold's Mouth

XHamster 9 months ago

Nurse Ruby's Monthly Milking: Chastity Patient Drained, & Locked in Inverted Cage

58% HD 0:39 / 12:34

Nurse Ruby's Monthly Milking: Chastity Patient Drained, & Locked in Inverted Cage

FapHouse 1 month ago

Kate England Hot Wife Cuckolding and Gives Husband a Snowball

Kate England Hot Wife Cuckolding and Gives Husband a Snowball

XHamster 2 months ago

Tia Cyrus Has a Cuckold That Just Wants to Watch

Tia Cyrus Has a Cuckold That Just Wants to Watch

XHamster 9 months ago

Cum Like a Girl - Feminized for a Girls Only JOI

52% 4K 0:29 / 20:17

Cum Like a Girl - Feminized for a Girls Only JOI

Clips4sale 1 year ago

Angelina Chung Caught Her Cuckold Jerking off

Angelina Chung Caught Her Cuckold Jerking off

XHamster 1 month ago

let me take u to the place where ur deppest and darkest desire become reallity, my pussy its perfect to squirt my ass for the greatest anal eve r

53% HD 2:00 / 4:51

let me take u to the place where ur deppest and darkest desire become reallity, my pussy its perfect to squirt my ass for the greatest anal eve r

Flirt4Free 3 years ago

Brittney & Elvis Private Show

58% HD 2:00 / 6:22

Brittney & Elvis Private Show

Flirt4Free 3 years ago

All Your Orgasms Are Mine || Femdom Ruined Orgasms Control & Denial

All Your Orgasms Are Mine || Femdom Ruined Orgasms Control & Denial

LoyalFans 4 years ago

Katie Morgan cuckold hardcore

Katie Morgan cuckold hardcore

XHamster 1 month ago

Sissy Feminization, Taping and Tucking Instruction.

Sissy Feminization, Taping and Tucking Instruction.

VivaTube 4 years ago

Sissy takes subs virginity part 1

51% HD 1:01 / 7:47

Sissy takes subs virginity part 1

FapHouse 4 years ago

Eden Adams Has a Cuckold That Is Broke, so Now He Has to Pay in a Different Way

Eden Adams Has a Cuckold That Is Broke, so Now He Has to Pay in a Different Way

XHamster 1 month ago

Reena Sky Brings a Black Stud Home for Her Cuckold to See

Reena Sky Brings a Black Stud Home for Her Cuckold to See

XHamster 2 months ago

Kacey Villainess Gets Fucked by a Black Bull While Her Cuckold Jerks off in the Corner

Kacey Villainess Gets Fucked by a Black Bull While Her Cuckold Jerks off in the Corner

XHamster 1 month ago

Andi James MILF Black Balling With Cuckold

Andi James MILF Black Balling With Cuckold

XHamster 8 months ago

Brittney Banxxx, Only Wants to Hear, as You Wish, From Her Cuckold

57% HD 0:39 / 34:26

Brittney Banxxx, Only Wants to Hear, as You Wish, From Her Cuckold

FapHouse 9 months ago

Bella Brookz Private Show

46% HD 2:00 / 14:02

Bella Brookz Private Show

Flirt4Free 3 years ago

Chelsea Roset Private Show

57% HD 2:00 / 26:30

Chelsea Roset Private Show

Flirt4Free 3 years ago

Sissy feminization, anal training, CEI cum drinking instruction (Arya Grander) - FemDom

Sissy feminization, anal training, CEI cum drinking instruction (Arya Grander) - FemDom

Amateur8 1 month ago

Small cock humiliation for gimp

Small cock humiliation for gimp

FapHouse 4 years ago

Bella Brookz Private Show

51% HD 2:00 / 9:32

Bella Brookz Private Show

Flirt4Free 3 years ago

Big Black Shiny Cock Strapon Mandy Flores

Big Black Shiny Cock Strapon Mandy Flores

Porner.TV 6 years ago

POV JOI vol 3

XHamster 2 years ago

Latex Dommes call in Gimps for Strap On Worship

Latex Dommes call in Gimps for Strap On Worship

Clips4sale 4 years ago

Phoenix Askani Shows Her Cuckold the Best Part of Chugging a Cock

Phoenix Askani Shows Her Cuckold the Best Part of Chugging a Cock

XHamster 1 month ago

Bella Brookz Private Show

67% HD 2:00 / 5:57

Bella Brookz Private Show

Flirt4Free 3 years ago

Bella Brookz Private Show

53% HD 2:00 / 7:57

Bella Brookz Private Show

Flirt4Free 3 years ago

Bisexual Encouragement Fantasies #9B: Training My Eager Faggot to Beg for Raw Creampies (Animated)

59% 0:30 / 11:53

Bisexual Encouragement Fantasies #9B: Training My Eager Faggot to Beg for Raw Creampies (Animated)

Clips4sale 7 months ago

Real Tutorial on How to Eat a Pussy with Alpha Instructions

Real Tutorial on How to Eat a Pussy with Alpha Instructions

XHamster 3 months ago

Ela Darling Is in Total Control of Her Cuckold Husband

Ela Darling Is in Total Control of Her Cuckold Husband

XHamster 3 months ago

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102,327 results found

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