Sissy Instruction Videos (22,713)

Sissy Instructing Part two

Sissy Instructing Part two

TrannyGem 4 years ago

New explosion to conclude the spell, Halloween Jerk Off Instructions

New explosion to conclude the spell, Halloween Jerk Off Instructions

TrannyGem 1 week ago

Liam Jacobson Private Show

62% HD 2:00 / 11:24

Liam Jacobson Private Show

Flirt4Free 10 months ago

7 MIN BOOTY WORKOUT with Equipment. Chantal Sweet

7 MIN BOOTY WORKOUT with Equipment. Chantal Sweet

xHamster 2 years ago

Luke Hardy & Cristian Ford Private Show

4K 2:00 / 19:32

Luke Hardy & Cristian Ford Private Show

Flirt4Free 3 weeks ago

Mommy Holy - Feminization - Time For Your First Chastity

Mommy Holy - Feminization - Time For Your First Chastity

xHamster 11 months ago

Maxx & Luccas & Jhordy & Brayan Private Show

HD 2:00 / 1:15:47

Maxx & Luccas & Jhordy & Brayan Private Show

Flirt4Free 4 weeks ago

Jessica Bloom Big Trans Cock Tease JOI CEI Edging with Fleshlight Self Suck and Cumplay

HD 1:01 / 24:46

Jessica Bloom Big Trans Cock Tease JOI CEI Edging with Fleshlight Self Suck and Cumplay

FapHouse 1 year ago

Huge cock shemale Cum eating instructions & JOI

Huge cock shemale Cum eating instructions & JOI

xHamster 11 months ago

Keisy Royce Private Show

HD 2:00 / 10:22

Keisy Royce Private Show

Flirt4Free 1 year ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 1 year ago

Ashly Chloe Private Show

HD 2:00 / 15:45

Ashly Chloe Private Show

Flirt4Free 3 years ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 9 months ago

Keisy Royce Private Show

HD 2:00 / 15:22

Keisy Royce Private Show

Flirt4Free 1 year ago

Fufu pin. Feminization. Sissification.

Fufu pin. Feminization. Sissification.

TrannyGem 9 months ago

Sissy Gender Lecture from Hate Cunt University

Sissy Gender Lecture from Hate Cunt University

Tranny.one 3 years ago

Transsexual sex toy hero - Try not to cum with innocent

Transsexual sex toy hero - Try not to cum with innocent

Love4Porn 4 years ago

The Gay Awakening Podcast Episode #15

48% HD 0:24 / 15:16

The Gay Awakening Podcast Episode #15

Clips4sale 2 years ago

Gabriella Bruni Private Show

Gabriella Bruni Private Show

Flirt4Free 3 weeks ago

Semi-public Sissy task

Semi-public Sissy task

Clips4sale 3 years ago

Mrs Lovings Sissy Instructing

Mrs Lovings Sissy Instructing

TrannyGem 3 years ago

Keisy Royce Private Show

HD 2:00 / 11:33

Keisy Royce Private Show

Flirt4Free 1 year ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 1 year ago

Condoms Full of My Cum

48% 4K 0:29 / 20:10

Condoms Full of My Cum

Clips4sale 5 months ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 2 months ago

Sophia Loreen Private Show

55% HD 2:00 / 4:44

Sophia Loreen Private Show

Flirt4Free 1 month ago

Anal Plug Instruction By Hannah to Spend Time With Futanaris

Anal Plug Instruction By Hannah to Spend Time With Futanaris

xHamster 4 months ago

CEI Jerk Off Instructions - Self Facial cumshot Directions With Jizm Munching

CEI Jerk Off Instructions - Self Facial cumshot Directions With Jizm Munching

TransTube.tv 8 months ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 2 years ago

Feelipe & Adara Private Show

HD 2:00 / 12:15

Feelipe & Adara Private Show

Flirt4Free 4 days ago

Roommate transformed you in a sissy and fucked your virgin ass with a strap on (FEMINIZATION ROLEPLAY - AI GENERATED)

Roommate transformed you in a sissy and fucked your virgin ass with a strap on (FEMINIZATION ROLEPLAY - AI GENERATED)

xHamster 6 months ago

Luke Hardy & Cristian Ford Private Show

48% 4K 2:00 / 6:57

Luke Hardy & Cristian Ford Private Show

Flirt4Free 2 months ago

[FayGrey] [Makise Kurisu's Catboy slut] (femdom, joi, cei, futanari, catboy)

[FayGrey] [Makise Kurisu's Catboy slut] (femdom, joi, cei, futanari, catboy)

HentaiGem 2 years ago

Keisy Royce Private Show

HD 2:00 / 16:59

Keisy Royce Private Show

Flirt4Free 2 years ago

Anal instructions for skinny bitch

Anal instructions for skinny bitch

aShemaleTube 3 months ago

Chinese dominatrix set your sissy goals to embrace feminization - Jerk Off Instructions ROLEPLAY

Chinese dominatrix set your sissy goals to embrace feminization - Jerk Off Instructions ROLEPLAY

HentaiGem 1 week ago

Ashly Chloe Private Show

HD 2:00 / 14:17

Ashly Chloe Private Show

Flirt4Free 3 years ago

Liam & Jacob Private Show

64% HD 2:00 / 5:51

Liam & Jacob Private Show

Flirt4Free 11 months ago

Keisy Royce Private Show

HD 2:00 / 11:09

Keisy Royce Private Show

Flirt4Free 1 year ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 1 year ago

Master & Ithan & Aleex Private Show

68% HD 2:00 / 34:42

Master & Ithan & Aleex Private Show

Flirt4Free 3 weeks ago

Dimitri Caruso Private Show

63% HD 2:00 / 9:59

Dimitri Caruso Private Show

Flirt4Free 2 years ago

Pink Pixie CD Sissy Tied & Bound 1 mov

38% 0:08 / 10:28

Pink Pixie CD Sissy Tied & Bound 1 mov

Clips4sale 8 months ago

Full Feminization and Tucking Teen Sissy Crossdresser

HD 1:01 / 40:05

Full Feminization and Tucking Teen Sissy Crossdresser

FapHouse 1 year ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 1 year ago

CEI transsexual domme Holly Hunt blows a load and turns you into a jism gobbling sissy Jerk Off Instructions

CEI transsexual domme Holly Hunt blows a load and turns you into a jism gobbling sissy Jerk Off Instructions

TrannyGem 6 months ago

William Raven Private Show

66% HD 2:00 / 35:56

William Raven Private Show

Flirt4Free 4 years ago

Master & Ithan Private Show

60% HD 2:00 / 13:43

Master & Ithan Private Show

Flirt4Free 2 months ago

Dimitri Caruso Private Show

4K 2:00 / 18:52

Dimitri Caruso Private Show

Flirt4Free 10 months ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 3 years ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 11 months ago

Dimitri Caruso Private Show

HD 2:00 / 21:31

Dimitri Caruso Private Show

Flirt4Free 2 years ago

Troy & Kiros Private Show

HD 2:00 / 23:31

Troy & Kiros Private Show

Flirt4Free 1 year ago

Paul Walkers Private Show

Paul Walkers Private Show

Flirt4Free 1 month ago

Maria Saint Private Show

Maria Saint Private Show

Flirt4Free 2 weeks ago

Feelipe & Adara Private Show

HD 2:00 / 25:52

Feelipe & Adara Private Show

Flirt4Free 4 weeks ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 1 year ago

The FAUX-COCK Jerk Off Instructions CEI Be so pulverizing Homosexual every Poking Day Game

The FAUX-COCK Jerk Off Instructions CEI Be so pulverizing Homosexual every Poking Day Game

TrannyGem 3 months ago

Sophia Loreen Private Show

66% HD 2:00 / 29:15

Sophia Loreen Private Show

Flirt4Free 2 years ago

Elix & Elias & Paulo Private Show

63% HD 2:00 / 5:20

Elix & Elias & Paulo Private Show

Flirt4Free 1 month ago

Gabriella Bruni Private Show

Gabriella Bruni Private Show

Flirt4Free 1 week ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 1 year ago

Fag Instructing 8

Fag Instructing 8

TransTube.tv 1 day ago

Sissy Instructing Part two

Sissy Instructing Part two

4Gay 2 weeks ago

[FayGrey] [Deceived and Sissified by Futa Bowsette] (Joi Cei Sissification Sissygasm AssDestruction E

[FayGrey] [Deceived and Sissified by Futa Bowsette] (Joi Cei Sissification Sissygasm AssDestruction E

HentaiGem 2 years ago

Dimitri Caruso Private Show

HD 2:00 / 41:02

Dimitri Caruso Private Show

Flirt4Free 2 years ago

Sophia Loreen Party on Aug 3, 2025 - Part 2

HD 2:00 / 59:42

Sophia Loreen Party on Aug 3, 2025 - Part 2

Flirt4Free 3 weeks ago

Sophia Loreen Private Show

59% HD 2:00 / 10:09

Sophia Loreen Private Show

Flirt4Free 1 month ago

Anthony Hard Private Show

HD 2:00 / 26:26

Anthony Hard Private Show

Flirt4Free 11 years ago

You never fuck a woman! Just a sexy pillow! LOL!!! JOI for real losers!

You never fuck a woman! Just a sexy pillow! LOL!!! JOI for real losers!

xHamster 11 months ago

Sophie Fantasy Private Show

38% HD 2:00 / 4:09

Sophie Fantasy Private Show

Flirt4Free 10 months ago

Jerk Off Instructions - Trans Queen Mellowditz Mistress Humiliatrix

Jerk Off Instructions - Trans Queen Mellowditz Mistress Humiliatrix

TrannyGem 7 months ago

Caught and sissified

60% HD 0:10 / 17:31

Caught and sissified

LoyalFans 4 years ago

R A L F

Flirt4Free 1 year ago

FETISH Game with my Sissy Hoe , Cum Eating Instruction

FETISH Game with my Sissy Hoe , Cum Eating Instruction

CrazyPorn 4 years ago

Jerking Off with Astolfo Part2(Hentai JOI) (Fate Grand Order JOI) (Fap the beat, breathplay, femboy)

Jerking Off with Astolfo Part2(Hentai JOI) (Fate Grand Order JOI) (Fap the beat, breathplay, femboy)

HentaiGem 3 years ago

Master & Ithan Private Show

43% HD 2:00 / 12:09

Master & Ithan Private Show

Flirt4Free 2 months ago

Dimitri Caruso Private Show

HD 2:00 / 27:30

Dimitri Caruso Private Show

Flirt4Free 3 years ago

Sophia Loreen Party on Oct 4, 2024 - Part 4

50% HD 2:00 / 59:33

Sophia Loreen Party on Oct 4, 2024 - Part 4

Flirt4Free 10 months ago

Seduced By Silk - Star Nine Mobile

66% 0:17 / 13:40

Seduced By Silk - Star Nine Mobile

Clips4sale 2 years ago

BIG LOVENSE IN HOLE

BIG LOVENSE IN HOLE

Flirt4Free 8 months ago

Mesmerized Tranny Sissy Instructing Compilation

Mesmerized Tranny Sissy Instructing Compilation

TrannyGem 6 years ago

Dimitri Caruso Private Show

HD 2:00 / 15:20

Dimitri Caruso Private Show

Flirt4Free 2 years ago

Femboy gets Jerk Off Instructions by Mistress Managing Masturbating Machine!

Femboy gets Jerk Off Instructions by Mistress Managing Masturbating Machine!

TrannyGem 1 year ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 1 year ago

$Jhordy Gets Fucked and Enjoys Luccas\' Tasty Semen$ 58% HD 2:00 / 27:28

Jhordy Gets Fucked and Enjoys Luccas\' Tasty Semen

Flirt4Free 3 weeks ago

Sissyfication Vol.4 by Sonechka25 (instructions on How to Achieve a Female Squirt for a Girl with a Penis).mp4

Sissyfication Vol.4 by Sonechka25 (instructions on How to Achieve a Female Squirt for a Girl with a Penis).mp4

xHamster 1 month ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 1 year ago

You were a bad boy! As a punishment, punch yourself while jerking off! JOI CBT GERMAN

You were a bad boy! As a punishment, punch yourself while jerking off! JOI CBT GERMAN

xHamster 11 months ago

How To Fit And JIZZ In A FuFu Pin (Step by Step Voice Guide)

How To Fit And JIZZ In A FuFu Pin (Step by Step Voice Guide)

TrannyGem 1 year ago

[FayGrey] [Futanari Harem - Horse cocked futas claim your ass] (Joi Cbt Roulette Ruin Sissification AnalTrainer Femdom)

[FayGrey] [Futanari Harem - Horse cocked futas claim your ass] (Joi Cbt Roulette Ruin Sissification AnalTrainer Femdom)

Eporner 2 years ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 1 year ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 1 year ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 1 year ago

Elvis & Alfonso & Master Private Show

39% HD 2:00 / 25:14

Elvis & Alfonso & Master Private Show

Flirt4Free 2 years ago

Keisy Royce Private Show

HD 2:00 / 21:20

Keisy Royce Private Show

Flirt4Free 1 year ago

Keisy Royce Private Show

HD 2:00 / 12:33

Keisy Royce Private Show

Flirt4Free 1 year ago

Dildo Hero - She Wants Some Fun

Dildo Hero - She Wants Some Fun

XVideos 2 years ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 1 year ago

Milking The Maid

70% HD 0:10 / 39:52

Milking The Maid

LoyalFans 7 months ago

Lovin’ Futa Petplay After A Rendezvous [Caboose-plow Futa Jerk Off Instructions]

Lovin’ Futa Petplay After A Rendezvous [Caboose-plow Futa Jerk Off Instructions]

TransTube.tv 11 months ago

Patric & Simon & Frederick Private Show

47% HD 2:00 / 11:22

Patric & Simon & Frederick Private Show

Flirt4Free 1 year ago

Amber Burnt Private Show

Amber Burnt Private Show

Flirt4Free 1 year ago

Luke Hardy & Cristian Ford Private Show

HD 2:00 / 22:48

Luke Hardy & Cristian Ford Private Show

Flirt4Free 2 months ago

Your futa friend grabs your hips and shoves her thick, hard cock deep into your virgin asshole, stretching it wide open. She pounds you hard and fast, fucking your ass like a dirty little whore until you&#039_re begging for her cum - AI

Your futa friend grabs your hips and shoves her thick, hard cock deep into your virgin asshole, stretching it wide open. She pounds you hard and fast, fucking your ass like a dirty little whore until you&#039_re begging for her cum - AI

XVideos 2 months ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 1 year ago

Mandy, Jerk Off Instructions en Español doll tu leche caliente en mi boca amor

Mandy, Jerk Off Instructions en Español doll tu leche caliente en mi boca amor

TrannyGem 2 years ago

Dimitri Caruso Private Show

HD 2:00 / 10:30

Dimitri Caruso Private Show

Flirt4Free 11 months ago

I promise I&#039_ll be gentle while fucking your tight butthole - SISSY FUTANARI ROLEPLAY JOI AI

I promise I&#039_ll be gentle while fucking your tight butthole - SISSY FUTANARI ROLEPLAY JOI AI

XVideos 1 month ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 1 year ago

Luke Hardy & Cristian Ford Private Show

57% HD 2:00 / 26:29

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 year ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 4 years ago

Mesmerized To Cum on Trans Feet - Ft: Goddess Marcy, Joey FeetGirls, Modestly Toasted (720p)

HD 0:25 / 10:30

Mesmerized To Cum on Trans Feet - Ft: Goddess Marcy, Joey FeetGirls, Modestly Toasted (720p)

Clips4sale 6 months ago

Luke Hardy & Cristian Ford Party on May 18, 2025 - Part 2

63% 4K 2:00 / 1:15:08

Luke Hardy & Cristian Ford Party on May 18, 2025 - Part 2

Flirt4Free 3 months ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 2 years ago

Lucie Taylor Private Show

Lucie Taylor Private Show

Flirt4Free 3 years ago

Luke Hardy & Cristian Ford Private Show

58% 4K 2:00 / 9:41

Luke Hardy & Cristian Ford Private Show

Flirt4Free 2 months ago

Luke Hardy & Cristian Ford Private Show

57% 4K 2:00 / 56:24

Luke Hardy & Cristian Ford Private Show

Flirt4Free 2 weeks ago

Keisy Royce Private Show

HD 2:00 / 11:37

Keisy Royce Private Show

Flirt4Free 1 year ago

Jerk Off Instructions (PUNHETA GUIDADA) ATÉ VOCÊ ENCHER EU CUZINHO DE LEITE

Jerk Off Instructions (PUNHETA GUIDADA) ATÉ VOCÊ ENCHER EU CUZINHO DE LEITE

Transvids.tv 1 month ago

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