Sissy Instruction (29,430)

The best and newest sissy instruction videos

Isadora Dunkan Private Show

4K 2:00 / 13:39

Isadora Dunkan Private Show

Camster 2 weeks ago

Bi Domination: Not Entirely Straight

57% HD 1:01 / 21:14

Bi Domination: Not Entirely Straight

FapHouse 2 months ago

Jhanne Cherry Private Show

59% HD 2:00 / 6:41

Jhanne Cherry Private Show

Flirt4Free 10 months ago

Angelica Swiss Party on Jul 4, 2026 - Part 3

65% HD 2:00 / 29:10

Angelica Swiss Party on Jul 4, 2026 - Part 3

Flirt4Free 5 days ago

Jhanne Cherry Private Show

51% 4K 2:00 / 5:43

Jhanne Cherry Private Show

Flirt4Free 11 months ago

Jhanne Cherry Private Show

52% HD 2:00 / 27:22

Jhanne Cherry Private Show

Flirt4Free 9 months ago

Jhanne Cherry Private Show

55% HD 2:00 / 8:06

Jhanne Cherry Private Show

Flirt4Free 10 months ago

POV JOI vol 3

XHamster 2 years ago

Andi James MILF Black Balling With Cuckold

Andi James MILF Black Balling With Cuckold

XHamster 5 months ago

... - Part 3

55% 4K 2:00 / 4:53

Camster 2 weeks ago

Don't Play This Video, if You're Into Vanilla or Velvet BDSM

Don't Play This Video, if You're Into Vanilla or Velvet BDSM

XHamster 1 week ago

Femdom POV: Sissification, Dirty Talk, Sph, CEI, JOI. Arya Grander and Mistress Priest

Femdom POV: Sissification, Dirty Talk, Sph, CEI, JOI. Arya Grander and Mistress Priest

XHamster 1 year ago

Femdom POV Sissy Training Pleasure Him

51% HD 1:01 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 3 months ago

Femdom POV Sissy Training Pleasure Him

49% HD 0:39 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 3 months ago

Emily & Stesha Private Show

52% 4K 2:00 / 5:57

Emily & Stesha Private Show

Flirt4Free 6 months ago

Jhanne Cherry Private Show

HD 2:00 / 40:31

Jhanne Cherry Private Show

Camster 9 months ago

Jhanne Cherry Private Show

51% 4K 2:00 / 23:18

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Holly Michaels Wants a Lazy with a Hard Cock but Not Her Cuckold's Tiny Penis Is Not What She Had in Mind

Holly Michaels Wants a Lazy with a Hard Cock but Not Her Cuckold's Tiny Penis Is Not What She Had in Mind

XHamster 4 months ago

Angelica Swiss Party on Jul 4, 2026

HD 2:00 / 1:44:09

Angelica Swiss Party on Jul 4, 2026

Camster 6 days ago

Isadora Dunkan Private Show

65% 4K 2:00 / 10:17

Isadora Dunkan Private Show

Camster 5 days ago

JOI for Anal CEI Ashley Sinclair

53% HD 1:01 / 7:03

JOI for Anal CEI Ashley Sinclair

FapHouse 2 months ago

Jhanne Cherry Private Show

54% HD 2:00 / 40:31

Jhanne Cherry Private Show

Flirt4Free 9 months ago

The Honey Pot Part 2

The Honey Pot Part 2

LoyalFans 4 months ago

Helena Red Private Show

65% HD 2:00 / 10:43

Helena Red Private Show

Flirt4Free 3 years ago

Size Queen Sissy Boy Training with CEI

HD 0:39 / 20:55

Size Queen Sissy Boy Training with CEI

FapHouse 2 days ago

Abril Newton Private Show

57% 4K 2:00 / 11:48

Abril Newton Private Show

Camster 11 months ago

Size Queen Sissy Boy Training with CEI

HD 1:01 / 20:55

Size Queen Sissy Boy Training with CEI

FapHouse 1 day ago

Audrey Royal Creampie Cuckold

Audrey Royal Creampie Cuckold

XHamster 1 year ago

Abril Newton Private Show

55% HD 2:00 / 19:22

Abril Newton Private Show

Flirt4Free 10 months ago

989 Perverted Stepdaddy, Panty Sniffer Turned Into Sissy Slut - CEI, Ruined Orgasm, Step-daughter in a College Outfit

66% HD 1:01 / 10:37

989 Perverted Stepdaddy, Panty Sniffer Turned Into Sissy Slut - CEI, Ruined Orgasm, Step-daughter in a College Outfit

FapHouse 1 year ago

Camilla Polls Private Show

58% 4K 2:00 / 11:32

Camilla Polls Private Show

Camster 2 weeks ago

Jhanne Cherry Private Show

46% HD 2:00 / 22:11

Jhanne Cherry Private Show

Flirt4Free 11 months ago

Camilla Polls Private Show

46% 4K 2:00 / 6:56

Camilla Polls Private Show

Camster 2 weeks ago

Audrey Royal Creampie Cuckold

61% HD 0:39 / 30:52

Audrey Royal Creampie Cuckold

FapHouse 1 year ago

Sissy Feminization, Taping and Tucking Instruction.

Sissy Feminization, Taping and Tucking Instruction.

VivaTube 3 years ago

Amber Fletcher Private Show

61% HD 2:00 / 5:43

Amber Fletcher Private Show

Flirt4Free 2 years ago

Abril Newton Private Show

58% HD 2:00 / 16:26

Abril Newton Private Show

Flirt4Free 11 months ago

... - Part 3

55% 4K 2:00 / 4:53

Flirt4Free 2 weeks ago

PaintedRose.Live - FemDom MILF Rosie In 'A Proper Spanking' Bad Little Pervert Need A Lesson On Behaving

PaintedRose.Live - FemDom MILF Rosie In 'A Proper Spanking' Bad Little Pervert Need A Lesson On Behaving

NewBestPorn 6 months ago

Step Mommy's Little Panty Boy: Teaching My Sissy Boy - Sissification & Panty Fetish Domina Andrea Rosu 4K

60% 4K 0:10 / 12:03

Step Mommy's Little Panty Boy: Teaching My Sissy Boy - Sissification & Panty Fetish Domina Andrea Rosu 4K

LoyalFans 1 year ago

Andi James MILF Black Balling With Cuckold

68% HD 1:01 / 25:52

Andi James MILF Black Balling With Cuckold

FapHouse 3 years ago

Emily & Stesha Private Show

58% 4K 2:00 / 8:48

Emily & Stesha Private Show

Flirt4Free 6 months ago

Sissy Summer

LoyalFans 1 month ago

Anal Training, Learning

HD 0:39 / 19:30

Anal Training, Learning

FapHouse 6 months ago

Emily & Stesha Private Show

49% 4K 2:00 / 5:53

Emily & Stesha Private Show

Flirt4Free 6 months ago

Sissy Cum in Chastity - Suspended by Hook

63% HD 0:39 / 7:21

Sissy Cum in Chastity - Suspended by Hook

FapHouse 2 weeks ago

Jhanne Cherry Private Show

49% 4K 2:00 / 22:26

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Emily & Stesha Private Show

75% 4K 2:00 / 8:54

Emily & Stesha Private Show

Flirt4Free 3 months ago

Kate Rhoades Private Show

63% 4K 2:00 / 10:43

Kate Rhoades Private Show

Flirt4Free 8 months ago

Ares & Adara Private Show

47% HD 2:00 / 20:07

Ares & Adara Private Show

Flirt4Free 1 year ago

Vends-ta-culotte - Gorgeous luscious French brunette gives you a good lesson of anal training

Vends-ta-culotte - Gorgeous luscious French brunette gives you a good lesson of anal training

XHamster 3 months ago

Miss Lylith's college for sissies - JOI

Miss Lylith's college for sissies - JOI

FapHouse 5 years ago

Beta Male Training Initiation

HD 0:10 / 34:22

Beta Male Training Initiation

LoyalFans 1 week ago

Amy Bllossom Private Show

61% HD 2:00 / 17:28

Amy Bllossom Private Show

Flirt4Free 11 months ago

Mommy Enouragement CEI

Mommy Enouragement CEI

Eporner 6 months ago

Betty Watkins Private Show

60% 4K 2:00 / 14:26

Betty Watkins Private Show

Flirt4Free 6 months ago

Emmalee Jones Party on Oct 30, 2025 - Part 2

4K 2:00 / 21:37

Emmalee Jones Party on Oct 30, 2025 - Part 2

Camster 8 months ago

I love dressing you like a girl. Jerk Off Instructions - StepMomFun

Premium HD 9:17

I love dressing you like a girl. Jerk Off Instructions - StepMomFun

XNXXGold 4 years ago

Lauren Newton Private Show

HD 2:00 / 11:08

Lauren Newton Private Show

Camster 5 months ago

Whore's Whore

HD 1:01 / 10:01

FapHouse 3 months ago

Emily & Stesha Private Show

61% 4K 2:00 / 11:42

Emily & Stesha Private Show

Camster 3 months ago

Jhanne Cherry Private Show

62% HD 2:00 / 4:58

Jhanne Cherry Private Show

Flirt4Free 9 months ago

Eye-Contact Pegging JOI Sissification POV - I Make My Sissy Princess Cum Like a Good Girl

Eye-Contact Pegging JOI Sissification POV - I Make My Sissy Princess Cum Like a Good Girl

XHamster 1 year ago

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

66% HD 2:00 / 4:53

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

Flirt4Free 1 year ago

Amy Bllossom Private Show

63% HD 2:00 / 16:39

Amy Bllossom Private Show

Camster 11 months ago

Jhanne Cherry Private Show

61% 4K 2:00 / 6:56

Jhanne Cherry Private Show

Flirt4Free 11 months ago

Angelica Swiss Party on Jul 4, 2026 - Part 3

HD 2:00 / 29:10

Angelica Swiss Party on Jul 4, 2026 - Part 3

Camster 5 days ago

Emily & Stesha Private Show

55% 4K 2:00 / 22:27

Emily & Stesha Private Show

Flirt4Free 2 months ago

Charlotte Flexes Naked

69% HD 2:00 / 3:51

Charlotte Flexes Naked

Flirt4Free 9 years ago

Mandy Lov Private Show

Mandy Lov Private Show

Camster 5 days ago

Charlotte Texas Private Show

HD 2:00 / 13:28

Charlotte Texas Private Show

Flirt4Free 3 years ago

Camilla Polls Private Show

68% 4K 2:00 / 11:32

Camilla Polls Private Show

Flirt4Free 2 weeks ago

Do You Like Shaved Pussies?

Do You Like Shaved Pussies?

Camster 2 years ago

Sexy Asian Mistress Dominates You

Sexy Asian Mistress Dominates You

FapHouse 1 week ago

Be a good little sissy whore for Me! Rub your clit while fingering your pussy!

HD 1:01 / 10:51

Be a good little sissy whore for Me! Rub your clit while fingering your pussy!

FapHouse 5 years ago

Just Admit You Love Cock by Diane Andrews Make Me Bi Fishnet Cock Lust JOI

Just Admit You Love Cock by Diane Andrews Make Me Bi Fishnet Cock Lust JOI

Pornzona 2 months ago

Pussy Eating Sissy (POV with CEI)

Pussy Eating Sissy (POV with CEI)

LoyalFans 1 year ago

Abril Newton Private Show

54% 4K 2:00 / 11:48

Abril Newton Private Show

Flirt4Free 11 months ago

Holly Michaels Wants a Lazy with a Hard Cock but Not Her Cuckold's Tiny Penis Is Not What She Had in Mind

HD 0:39 / 44:07

Holly Michaels Wants a Lazy with a Hard Cock but Not Her Cuckold's Tiny Penis Is Not What She Had in Mind

FapHouse 4 months ago

Mandy Lov Private Show

4K 2:00 / 13:14

Mandy Lov Private Show

Flirt4Free 1 week ago

Isadora Dunkan Private Show

Isadora Dunkan Private Show

Camster 1 week ago

Pegging Keeps You Obedient - Femdom Sub Training JOI

57% HD 0:39 / 11:01

Pegging Keeps You Obedient - Femdom Sub Training JOI

FapHouse 1 year ago

Fucking My Pussy Hard

58% 4K 2:00 / 5:10

Fucking My Pussy Hard

Camster 2 years ago

Ares & Adara Private Show

53% HD 2:00 / 9:20

Ares & Adara Private Show

Flirt4Free 1 year ago

Emily & Stesha Private Show

40% 4K 2:00 / 7:33

Emily & Stesha Private Show

Flirt4Free 5 months ago

Jhanne Cherry Private Show

55% 4K 2:00 / 6:40

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Sissy Cum in Chastity - Suspended by Hook

Sissy Cum in Chastity - Suspended by Hook

FapHouse 2 weeks ago

Mandy Lov Private Show

4K 2:00 / 17:11

Mandy Lov Private Show

Camster 4 days ago

Emily & Stesha Private Show

Emily & Stesha Private Show

Camster 2 months ago

Pussy Eating Sissy (with CEI)

63% HD 0:39 / 10:01

Pussy Eating Sissy (with CEI)

FapHouse 1 year ago

Sissy Feminization, Anal Training, Cei Cum Eating Instruction - Femdom Pov Domination

Sissy Feminization, Anal Training, Cei Cum Eating Instruction - Femdom Pov Domination

Boobse.com 1 week ago

Amy Bllossom Private Show

HD 2:00 / 27:26

Amy Bllossom Private Show

Camster 8 months ago

PROFOUND BUTTHOLE TRAINING FemDom Bi Encouragement Non Humiliation Jerk Away Instruction Mommy Strap Upon POV

PROFOUND BUTTHOLE TRAINING FemDom Bi Encouragement Non Humiliation Jerk Away Instruction Mommy Strap Upon POV

KAMS 1 year ago

Mandy Lov Private Show

Mandy Lov Private Show

Camster 3 days ago

PaintedRose.Live - FemDom MILF Rosie In 'A Proper Spanking' Bad Little Pervert Need A Lesson On Behaving

PaintedRose.Live - FemDom MILF Rosie In 'A Proper Spanking' Bad Little Pervert Need A Lesson On Behaving

Juicexxx 6 months ago

Kandi More & Jamer Private Show

58% HD 2:00 / 56:41

Kandi More & Jamer Private Show

Flirt4Free 3 years ago

Martina Sweett Private Show

HD 2:00 / 43:18

Martina Sweett Private Show

Camster 1 year ago

Emmalee Jones Takes Bbc

Emmalee Jones Takes Bbc

Camster 9 months ago

Sissy Wife's First Anal JOI

HD 0:10 / 17:38

Sissy Wife's First Anal JOI

LoyalFans 3 weeks ago

Camilla Polls Private Show

4K 2:00 / 32:28

Camilla Polls Private Show

Camster 3 weeks ago

Jhanne Cherry Private Show

Jhanne Cherry Private Show

Camster 9 months ago

Jhanne Cherry Private Show

60% 4K 2:00 / 9:09

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Emily & Stesha Private Show

64% 4K 2:00 / 4:10

Emily & Stesha Private Show

Flirt4Free 6 months ago

Angelica Swiss Party on Oct 21, 2025

63% 4K 2:00 / 2:03:16

Angelica Swiss Party on Oct 21, 2025

Flirt4Free 8 months ago

Amber Fletcher Private Show

61% HD 2:00 / 5:11

Amber Fletcher Private Show

Camster 1 year ago

Abril Newton Private Show

70% 4K 2:00 / 8:57

Abril Newton Private Show

Flirt4Free 9 months ago

Mafe Flex & Sebastiaan Private Show

55% 4K 2:00 / 4:32

Mafe Flex & Sebastiaan Private Show

Flirt4Free 6 months ago

Sissy Wife's First Anal JOI - Clara Dee JOI

Sissy Wife's First Anal JOI - Clara Dee JOI

XHamster 2 years ago

Sissy Anal JOI

66% HD 0:39 / 7:41

FapHouse 2 years ago

Anal Training, Learning

Anal Training, Learning

XHamster 5 months ago

Do You Like It Better, Fingers in the Ass or a Big Toy?

59% HD 2:00 / 9:58

Do You Like It Better, Fingers in the Ass or a Big Toy?

Flirt4Free 2 years ago

Lauren Newton Private Show

Lauren Newton Private Show

Flirt4Free 2 days ago

Abril Newton Private Show

HD 2:00 / 32:13

Abril Newton Private Show

Camster 11 months ago

Lauren Newton Private Show

HD 2:00 / 44:35

Lauren Newton Private Show

Camster 2 weeks ago

Kate Rhoades Private Show

64% 4K 2:00 / 4:20

Kate Rhoades Private Show

Flirt4Free 8 months ago

Femdom Mommy Jerk Instructions For Sissies

Femdom Mommy Jerk Instructions For Sissies

UiPorn 6 years ago

Viuda Nagra Private Show

46% HD 2:00 / 9:57

Viuda Nagra Private Show

Flirt4Free 3 years ago

JOI Cuck Anal Training CEI Next Level - Luna Doll

JOI Cuck Anal Training CEI Next Level - Luna Doll

XHamster 11 months ago

EDGING JOI WITH KEGEL WEIGHTLIFTING + BONUS - DAY #4

EDGING JOI WITH KEGEL WEIGHTLIFTING + BONUS - DAY #4

XHamster 3 years ago

Audrey Royal Creampie Cuckold

65% HD 1:01 / 30:52

Audrey Royal Creampie Cuckold

FapHouse 1 year ago

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