Sissy Instructions (14,017)

The best and newest sissy instructions videos

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 3 weeks ago

Swallow Your Cum, Sperm Slut!

Swallow Your Cum, Sperm Slut!

xHamster 3 months ago

Jhanne Cherry Private Show

50% 4K 2:00 / 23:18

Jhanne Cherry Private Show

Flirt4Free 8 months ago

Sissy Training Part 2 - Oral

57% 4K 0:39 / 38:08

Sissy Training Part 2 - Oral

FapHouse 2 months ago

Jhanne Cherry Private Show

49% 4K 2:00 / 22:26

Jhanne Cherry Private Show

Flirt4Free 8 months ago

Betty Watkins Private Show

62% 4K 2:00 / 14:26

Betty Watkins Private Show

Flirt4Free 3 months ago

Caged Clitty Ruined

Caged Clitty Ruined

xHamster 2 weeks ago

BEST RUINED ORGASM JOI

BEST RUINED ORGASM JOI

Pornfact 3 weeks ago

Abril Newton Private Show

73% HD 2:00 / 6:54

Abril Newton Private Show

Flirt4Free 6 months ago

Jhanne Cherry Private Show

67% 4K 2:00 / 4:55

Jhanne Cherry Private Show

Flirt4Free 8 months ago

Mommy Enouragement CEI

Mommy Enouragement CEI

Eporner 2 months ago

Kate Rhoades Private Show

61% 4K 2:00 / 4:18

Kate Rhoades Private Show

Flirt4Free 4 months ago

Big Breasted MILF Gives Jerk off Instructions and humiliates Small cock

Big Breasted MILF Gives Jerk off Instructions and humiliates Small cock

Pornfact 3 days ago

Jhanne Cherry Private Show

54% 4K 2:00 / 4:09

Jhanne Cherry Private Show

Flirt4Free 8 months ago

POV JOI vol 3

xHamster 2 years ago

Jhanne Cherry Private Show

51% HD 2:00 / 14:54

Jhanne Cherry Private Show

Flirt4Free 6 months ago

Jhanne Cherry Private Show

48% HD 2:00 / 22:11

Jhanne Cherry Private Show

Flirt4Free 7 months ago

EDGING JOI WITH KEGEL WEIGHTLIFTING + BONUS - DAY #4

EDGING JOI WITH KEGEL WEIGHTLIFTING + BONUS - DAY #4

xHamster 3 years ago

Ava Maddison Private Show

58% 4K 2:00 / 29:24

Ava Maddison Private Show

Flirt4Free 4 weeks ago

POV Pegging JOI CEI Sissy Training - Eat Your Sissy Cream

POV Pegging JOI CEI Sissy Training - Eat Your Sissy Cream

xHamster 4 months ago

Jhanne Cherry Private Show

64% 4K 2:00 / 14:24

Jhanne Cherry Private Show

Flirt4Free 8 months 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 2 weeks ago

Andi James MILF Black Balling With Cuckold

Andi James MILF Black Balling With Cuckold

xHamster 1 month 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

Andi James MILF Black Balling With Cuckold

63% HD 1:01 / 25:52

Andi James MILF Black Balling With Cuckold

FapHouse 2 years ago

Emily & Stesha Private Show

53% 4K 2:00 / 5:53

Emily & Stesha Private Show

Flirt4Free 3 months ago

Jhanne Cherry Private Show

56% 4K 2:00 / 6:21

Jhanne Cherry Private Show

Flirt4Free 8 months ago

Abril Newton Private Show

58% HD 2:00 / 16:26

Abril Newton Private Show

Flirt4Free 8 months ago

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

66% HD 0:39 / 10:37

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

FapHouse 1 year ago

Jhanne Cherry Private Show

56% HD 2:00 / 40:31

Jhanne Cherry Private Show

Flirt4Free 6 months ago

Turned Out Sissy Interactive Toy Experience

Turned Out Sissy Interactive Toy Experience

LoyalFans 10 months ago

Sissy Training Part 2 - Oral

43% 4K 1:01 / 38:08

Sissy Training Part 2 - Oral

FapHouse 2 months ago

Cassie Flexen Private Show

61% HD 2:00 / 15:45

Cassie Flexen Private Show

Flirt4Free 1 week ago

Emily & Stesha Private Show

58% 4K 2:00 / 5:57

Emily & Stesha Private Show

Flirt4Free 3 months ago

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

61% 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

Helena Red Private Show

70% HD 2:00 / 10:43

Helena Red Private Show

Flirt4Free 3 years ago

Caged Clitty Ruined

Caged Clitty Ruined

FapHouse 2 weeks ago

Angelica Swiss Party on Jan 21, 2026 - Part 2

63% 4K 2:00 / 4:00:00+

Angelica Swiss Party on Jan 21, 2026 - Part 2

Flirt4Free 2 months ago

Jhanne Cherry Private Show

66% 4K 2:00 / 4:59

Jhanne Cherry Private Show

Flirt4Free 8 months ago

Camilla Polls Private Show

65% 4K 2:00 / 25:57

Camilla Polls Private Show

Flirt4Free 7 months ago

Betty Sandra Private Show

59% HD 2:00 / 14:37

Betty Sandra Private Show

Flirt4Free 4 years ago

Amy Bllossom Private Show

59% HD 2:00 / 17:28

Amy Bllossom Private Show

Flirt4Free 7 months ago

Abril Newton Private Show

56% HD 2:00 / 19:22

Abril Newton Private Show

Flirt4Free 7 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 3 years ago

Emily & Stesha Private Show

54% 4K 2:00 / 4:08

Emily & Stesha Private Show

Flirt4Free 2 months ago

Emily & Stesha Private Show

51% 4K 2:00 / 29:40

Emily & Stesha Private Show

Flirt4Free 3 months ago

Emily & Stesha Private Show

64% 4K 2:00 / 8:54

Emily & Stesha Private Show

Flirt4Free 1 week ago

Panty Wearing SPH - Clara Dee JOI

Panty Wearing SPH - Clara Dee JOI

xHamster 3 years ago

Jhanne Cherry Private Show

50% HD 2:00 / 27:22

Jhanne Cherry Private Show

Flirt4Free 6 months ago

Pegging Keeps You Obedient - Femdom Sub Training JOI

HD 1:01 / 11:01

Pegging Keeps You Obedient - Femdom Sub Training JOI

FapHouse 8 months ago

Emily & Stesha Private Show

65% 4K 2:00 / 11:42

Emily & Stesha Private Show

Flirt4Free 1 day ago

Jhanne Cherry Private Show

60% HD 2:00 / 8:06

Jhanne Cherry Private Show

Flirt4Free 6 months ago

Emily & Stesha Private Show

62% 4K 2:00 / 8:48

Emily & Stesha Private Show

Flirt4Free 3 months ago

Anal Training, Learning

Anal Training, Learning

xHamster 2 months ago

Angelica Swiss Party on Oct 21, 2025

71% 4K 2:00 / 2:03:16

Angelica Swiss Party on Oct 21, 2025

Flirt4Free 5 months ago

Barbara Xoxox Private Show

61% 4K 2:00 / 11:32

Barbara Xoxox Private Show

Flirt4Free 1 month 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 1:01 / 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 3 weeks ago

Jhanne Cherry Private Show

50% HD 2:00 / 5:01

Jhanne Cherry Private Show

Flirt4Free 6 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 3 weeks ago

Emily & Stesha Private Show

49% 4K 2:00 / 12:53

Emily & Stesha Private Show

Flirt4Free 1 month ago

JOI Cuck Anal Training CEI Next Level - Luna Doll

JOI Cuck Anal Training CEI Next Level - Luna Doll

xHamster 8 months ago

Viuda Nagra Private Show

59% HD 2:00 / 9:51

Viuda Nagra Private Show

Flirt4Free 3 years ago

Emily & Stesha Private Show

55% 4K 2:00 / 4:07

Emily & Stesha Private Show

Flirt4Free 3 months ago

Jhanne Cherry Private Show

58% HD 2:00 / 6:41

Jhanne Cherry Private Show

Flirt4Free 6 months ago

Mistress Olivia trains you little slut to be a sissy whore! German mistress with huge titsDirtytalk

Mistress Olivia trains you little slut to be a sissy whore! German mistress with huge titsDirtytalk

xHamster 2 months ago

Emmalee Jones Private Show

Emmalee Jones Private Show

Flirt4Free 3 weeks ago

Camilla Polls Private Show

56% 4K 2:00 / 5:37

Camilla Polls Private Show

Flirt4Free 8 months ago

Reven Mayers Private Show

HD 2:00 / 10:30

Reven Mayers Private Show

Flirt4Free 1 week ago

Abril Newton Private Show

57% 4K 2:00 / 11:48

Abril Newton Private Show

Flirt4Free 8 months ago

Emily & Stesha Private Show

61% 4K 2:00 / 1:15:29

Emily & Stesha Private Show

Flirt4Free 2 months ago

Pussy Eating Sissy (with CEI)

Pussy Eating Sissy (with CEI)

xHamster 11 months ago

Audrey Royal Creampie Cuckold

Audrey Royal Creampie Cuckold

xHamster 9 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

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

xHamster 3 weeks ago

Charlotte Flexes Naked

68% HD 2:00 / 3:51

Charlotte Flexes Naked

Flirt4Free 9 years ago

Bondage Show

53% HD 2:00 / 36:00

Flirt4Free 2 years ago

Emily & Stesha Private Show

59% 4K 2:00 / 4:11

Emily & Stesha Private Show

Flirt4Free 3 months ago

Sissy Anal JOI

66% HD 0:39 / 7:41

FapHouse 2 years ago

Audrey Royal Creampie Cuckold

69% HD 1:01 / 30:52

Audrey Royal Creampie Cuckold

FapHouse 9 months ago

Sarah Flower Private Show

66% HD 2:00 / 14:40

Sarah Flower Private Show

Flirt4Free 3 years 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 9 months ago

Camilla Polls Private Show

57% 4K 2:00 / 6:05

Camilla Polls Private Show

Flirt4Free 8 months ago

U'll Be Her Faggot Bitch

U'll Be Her Faggot Bitch

FreePorn8 1 year ago

Amazing Blowjob

64% HD 2:00 / 10:58

Amazing Blowjob

Flirt4Free 1 year ago

Jhanne Cherry Private Show

54% 4K 2:00 / 5:30

Jhanne Cherry Private Show

Flirt4Free 8 months ago

Isadora Dunkan Private Show

4K 2:00 / 2:16:17

Isadora Dunkan Private Show

Flirt4Free 1 day ago

Chelsea Roset Private Show

60% HD 2:00 / 26:30

Chelsea Roset Private Show

Flirt4Free 2 years ago

Ares & Adara Private Show

55% HD 2:00 / 9:20

Ares & Adara Private Show

Flirt4Free 1 year ago

Sissy Feminization, Taping and Tucking Instruction.

Sissy Feminization, Taping and Tucking Instruction.

VivaTube 3 years ago

Empowering Submission: Goddess Hasmik's Ultimate Edging Challenge with JOI

Empowering Submission: Goddess Hasmik's Ultimate Edging Challenge with JOI

JuicyVid 4 months ago

Andi James MILF Black Balling With Cuckold

44% HD 0:39 / 25:52

Andi James MILF Black Balling With Cuckold

FapHouse 2 years ago

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

49% HD 2:00 / 4:52

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

Flirt4Free 1 year ago

Emmalee Jones Party on Mar 8, 2026 - Part 3

55% 4K 2:00 / 30:37

Emmalee Jones Party on Mar 8, 2026 - Part 3

Flirt4Free 3 weeks ago

JOI Cuck Anal Training CEI Next Level - Luna Doll

64% 1:01 / 15:22

JOI Cuck Anal Training CEI Next Level - Luna Doll

FapHouse 8 months ago

Emily & Stesha Private Show

54% 4K 2:00 / 7:00

Emily & Stesha Private Show

Flirt4Free 2 months ago

Jhanne Cherry Private Show

63% 4K 2:00 / 7:17

Jhanne Cherry Private Show

Flirt4Free 8 months ago

Jhanne Cherry Private Show

59% HD 2:00 / 4:58

Jhanne Cherry Private Show

Flirt4Free 5 months ago

I'll Make You a Sissy - You Won't Wear Boxer Shorts Anymore

I'll Make You a Sissy - You Won't Wear Boxer Shorts Anymore

FapHouse 1 year ago

Kate Rhoades Private Show

59% 4K 2:00 / 11:18

Kate Rhoades Private Show

Flirt4Free 4 months ago

Amber Fletcher Private Show

64% HD 2:00 / 5:43

Amber Fletcher Private Show

Flirt4Free 1 year ago

Jhanne Cherry Private Show

63% 4K 2:00 / 10:38

Jhanne Cherry Private Show

Flirt4Free 8 months ago

Naty Desiree & Evelyn Evy Private Show

68% 4K 2:00 / 4:03

Naty Desiree & Evelyn Evy Private Show

Flirt4Free 1 month ago

Emmalee Jones Sucks and Fucks in Fuzzy Socks

62% 4K 2:00 / 7:29

Emmalee Jones Sucks and Fucks in Fuzzy Socks

Flirt4Free 7 months ago

Emily & Stesha Private Show

60% 4K 2:00 / 56:10

Emily & Stesha Private Show

Flirt4Free 1 week ago

Sissy Anal JOI

47% HD 1:01 / 7:41

FapHouse 2 years ago

Jhanne Cherry Private Show

60% 4K 2:00 / 6:40

Jhanne Cherry Private Show

Flirt4Free 8 months ago

U'll Be Her Faggot Bitch

U'll Be Her Faggot Bitch

SortPorn 4 years ago

Eat It for Mistress - CEI

Eat It for Mistress - CEI

xHamster 1 year ago

Reven Mayers Private Show

Reven Mayers Private Show

Flirt4Free 1 week ago

Viuda Nagra Private Show

48% HD 2:00 / 9:57

Viuda Nagra Private Show

Flirt4Free 3 years ago

Camilla Polls Private Show

70% 4K 2:00 / 8:54

Camilla Polls Private Show

Flirt4Free 8 months 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

Pornfact 1 month ago

Amber Fletcher Private Show

56% HD 2:00 / 6:03

Amber Fletcher Private Show

Flirt4Free 1 year ago

Emmalee Jones Private Show

4K 2:00 / 11:21

Emmalee Jones Private Show

Flirt4Free 3 weeks ago

Abril Newton Private Show

67% 4K 2:00 / 8:57

Abril Newton Private Show

Flirt4Free 6 months ago

teasing - Part 2

teasing - Part 2

Flirt4Free 1 week ago

How About You Fill My Ass Hole with Milk?

58% HD 2:00 / 27:56

How About You Fill My Ass Hole with Milk?

Flirt4Free 2 years ago

Anal jerk off instructions for faggots. Femdom JOI.

Anal jerk off instructions for faggots. Femdom JOI.

xHamster 5 years ago

Abril Newton Private Show

53% HD 2:00 / 12:59

Abril Newton Private Show

Flirt4Free 7 months ago

Ares & Adara Private Show

47% HD 2:00 / 20:07

Ares & Adara Private Show

Flirt4Free 1 year ago

Tali Majid Private Show

4K 2:00 / 14:01

Tali Majid Private Show

Flirt4Free 1 week ago

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