Sissy Transformation (3,503)

The Sissygasm

47% 1:01 / 12:01

FapHouse 8 months ago

Episode 2: Part 1: a Transformed Life: New Sissy Sexuality - Maitresse Julia

76% HD 1:01 / 13:19

Episode 2: Part 1: a Transformed Life: New Sissy Sexuality - Maitresse Julia

FapHouse 1 year ago

Sissy Training - Teaching My Friend How to Give a Blowjob

68% HD 1:01 / 29:53

Sissy Training - Teaching My Friend How to Give a Blowjob

FapHouse 1 year ago

Transforming You into My Sweet, Short, Pantiless Maid

52% HD 0:10 / 22:16

Transforming You into My Sweet, Short, Pantiless Maid

LoyalFans 1 year ago

Lady boss transforms you into sissy secretary part 1

47% HD 1:01 / 9:51

Lady boss transforms you into sissy secretary part 1

FapHouse 6 years ago

Sissy Training Part 2 - Oral

58% 4K 1:01 / 38:08

Sissy Training Part 2 - Oral

FapHouse 4 weeks ago

Sissy & cuckold training

51% HD 1:01 / 11:45

Sissy & cuckold training

FapHouse 5 years ago

Fun Feminization

49% HD 0:10 / 5:34

Fun Feminization

LoyalFans 7 months ago

Made to Be a Slut and Feminized by the Birthday Girl

58% HD 1:01 / 11:17

Made to Be a Slut and Feminized by the Birthday Girl

FapHouse 4 months ago

Sissy Stash Discovered

51% HD 0:10 / 6:14

Sissy Stash Discovered

LoyalFans 1 day ago

Poor Cuckold: the Wedding Anniversary

56% HD 0:39 / 36:28

Poor Cuckold: the Wedding Anniversary

FapHouse 2 years ago

Boy to Girl - Permanent Transformation

50% HD 1:01 / 8:47

Boy to Girl - Permanent Transformation

FapHouse 1 year ago

1st Sissy Experience With Miss Shell

57% HD 0:10 / 23:00

1st Sissy Experience With Miss Shell

LoyalFans 2 years ago

Erotic Humiliation

63% HD 1:01 / 51:56

Erotic Humiliation

FapHouse 2 months ago

Your Lesbian Wife Turns You Into a Woman - Clara Dee POV Virtual Sex Sissy Pegging

Your Lesbian Wife Turns You Into a Woman - Clara Dee POV Virtual Sex Sissy Pegging

xHamster 1 year ago

Dominatrix Mistress April, getting real boobs

50% HD 1:01 / 22:22

Dominatrix Mistress April, getting real boobs

FapHouse 3 years ago

Sissy Boyfriend Found Out and Pegged

50% HD 0:10 / 18:38

Sissy Boyfriend Found Out and Pegged

LoyalFans 3 years ago

Your Lesbian Wife Turns You Into a Woman - Clara Dee POV Virtual Sex Sissy Pegging

53% HD 1:01 / 22:02

Your Lesbian Wife Turns You Into a Woman - Clara Dee POV Virtual Sex Sissy Pegging

FapHouse 1 year ago

Total Transformation - HD

39% HD 0:10 / 5:28

Total Transformation - HD

LoyalFans 7 months ago

Feminization, Crossdressing & Sissification

63% HD 0:39 / 57:20

Feminization, Crossdressing & Sissification

FapHouse 1 month ago

Cheerleader Femdom: Peeping Tom's Sissy Makeover Punishment

51% HD 0:10 / 11:26

Cheerleader Femdom: Peeping Tom's Sissy Makeover Punishment

LoyalFans 3 months ago

Transformation complete, time to train the sissy slut hole

52% HD 0:10 / 15:18

Transformation complete, time to train the sissy slut hole

LoyalFans 5 months 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 Step 5

49% HD 0:10 / 17:04

LoyalFans 1 year ago

Feminization, Crossdressing & Sissification

60% HD 1:01 / 57:20

Feminization, Crossdressing & Sissification

FapHouse 1 month ago

Sissy Maid Makeover feat Domina Monica

HD 0:10 / 15:55

Sissy Maid Makeover feat Domina Monica

LoyalFans 1 week ago

(Preview) Sissies Dungeon Play

67% HD 0:10 / 1:10

(Preview) Sissies Dungeon Play

LoyalFans 3 months ago

Be My Pegging Bitch

56% HD 1:01 / 15:56

Be My Pegging Bitch

FapHouse 4 months ago

Magic Fantasy: I Transform You Into a Real Sissy Slave Girl

63% HD 0:07 / 0:40

Magic Fantasy: I Transform You Into a Real Sissy Slave Girl

FapHouse 3 months ago

Boy to Girl - Permanent Transformation

57% HD 0:08 / 0:40

Boy to Girl - Permanent Transformation

FapHouse 3 months ago

Baby Boy No More! - Goddess Amber

60% HD 0:10 / 11:50

Baby Boy No More! - Goddess Amber

LoyalFans 1 year ago

Your Sissy Resolutions - 383

HD 0:10 / 10:16

Your Sissy Resolutions - 383

LoyalFans 2 days ago

German Sissy Becomes Whore Fatma a True Transformation

64% HD 0:07 / 0:40

German Sissy Becomes Whore Fatma a True Transformation

FapHouse 3 months ago

Poor Cuckold: the Wedding Anniversary

58% HD 1:01 / 36:28

Poor Cuckold: the Wedding Anniversary

FapHouse 2 years ago

Sissy Step 7

48% HD 0:10 / 21:22

LoyalFans 1 year ago

Latex Sissy Reprogrammed Into Cock Drone! Ft Miss Roper

63% HD 0:10 / 9:10

Latex Sissy Reprogrammed Into Cock Drone! Ft Miss Roper

LoyalFans 1 year ago

Sissy Anal JOI

52% HD 1:01 / 7:41

FapHouse 2 years ago

Suck Your Friends Cock with Me

Suck Your Friends Cock with Me

FapHouse 2 days ago

AFTERNOON PEGGING: feminized boyfriend gets his ass pounded by mommy

AFTERNOON PEGGING: feminized boyfriend gets his ass pounded by mommy

xHamster 8 months ago

Lingerie Try on, Sissification, Underwear Drawer

HD 1:01 / 10:29

Lingerie Try on, Sissification, Underwear Drawer

FapHouse 3 months ago

Two Sissies Love to Suck Mistress's Strap-on and Love to Be Used!

56% HD 1:01 / 13:27

Two Sissies Love to Suck Mistress's Strap-on and Love to Be Used!

FapHouse 1 year ago

Role Reversal: Gender Swap

Role Reversal: Gender Swap

FapHouse 1 year ago

Sissy Institution 3 (4K)

4K 0:10 / 12:11

Sissy Institution 3 (4K)

LoyalFans 1 week ago

Lady boss transforms you into sissy secretary part 2

56% HD 0:24 / 9:48

Lady boss transforms you into sissy secretary part 2

FapHouse 6 years ago

My Husband Sissified: A Female Latex Slave Doll Pegged - Mistress Julia feat. Sukeban

58% 4K 0:10 / 20:46

My Husband Sissified: A Female Latex Slave Doll Pegged - Mistress Julia feat. Sukeban

LoyalFans 5 months ago

30 Days Mtf Complete Transformation - Slut Training - Crossdressing - Bimbofication - Femdom POV

47% HD 1:01 / 10:01

30 Days Mtf Complete Transformation - Slut Training - Crossdressing - Bimbofication - Femdom POV

FapHouse 9 months ago

FULL LIVE - Sissification Slumber Party & Beta Bullying - Featuring Goddess Jay

55% HD 0:10 / 2:40:24

FULL LIVE - Sissification Slumber Party & Beta Bullying - Featuring Goddess Jay

LoyalFans 2 weeks ago

Skater Boy to Sissy Slut Transformation! with Ruby Onyx

49% HD 0:10 / 12:47

Skater Boy to Sissy Slut Transformation! with Ruby Onyx

LoyalFans 3 years ago

From man to sissy, a full feminisation transformation, the full journey from male to female, undergoing makeup application to make her pretty for the cocks she's going to service! (HD)

53% 4K 0:20 / 20:02

From man to sissy, a full feminisation transformation, the full journey from male to female, undergoing makeup application to make her pretty for the cocks she's going to service! (HD)

Clips4sale 2 years ago

Sissy Academy Part 1

Sissy Academy Part 1

xHamster 4 months ago

Pretty Obedience

HD 1:01 / 13:38

Pretty Obedience

FapHouse 1 week ago

Wasser aus meinem Mund (deutsches video)/Water from my mouth for the Rubbersluts

59% HD 0:10 / 14:39

Wasser aus meinem Mund (deutsches video)/Water from my mouth for the Rubbersluts

LoyalFans 2 years ago

No, Please!

LoyalFans 1 month ago

Full Doll Transformation (FHD)

61% HD 0:10 / 18:19

Full Doll Transformation (FHD)

LoyalFans 1 year ago

Sissy Birthday Surprise

66% HD 0:39 / 15:09

Sissy Birthday Surprise

FapHouse 3 weeks ago

Feminine Hair Spell

HD 0:10 / 22:45

Feminine Hair Spell

LoyalFans 1 week ago

Two dommes and the delivery boy - The Restraint

48% HD 0:10 / 7:58

Two dommes and the delivery boy - The Restraint

LoyalFans 1 year ago

Locktober - Cage 7: Business guy transformed into Sissy bimbo by hawt Headmistress in Leather Leggings

Locktober - Cage 7: Business guy transformed into Sissy bimbo by hawt Headmistress in Leather Leggings

PornFreeNow 1 month ago

Fuck Me Sensei 1 Mrs. Sissy's Deep-fist Treatment

Fuck Me Sensei 1 Mrs. Sissy's Deep-fist Treatment

FapHouse 1 month ago

Worship This Goddess Cock

62% HD 0:10 / 19:25

Worship This Goddess Cock

LoyalFans 1 year ago

Locktober - Cage 7: Business man transformed into Sissy bimbo slut by hot Mistress in Leather Leggings

Locktober - Cage 7: Business man transformed into Sissy bimbo slut by hot Mistress in Leather Leggings

xHamster 1 year ago

Gender Transform Bundle

70% HD 0:10 / 1:02:26

Gender Transform Bundle

LoyalFans 2 weeks ago

The Bimbo Diagnosis - Your Fate as a Sissy Slut Is Sealed! Chastity, Strap On, Tied Up in Bondage and BRED Like A WHORE-POV

HD 0:10 / 25:02

The Bimbo Diagnosis - Your Fate as a Sissy Slut Is Sealed! Chastity, Strap On, Tied Up in Bondage and BRED Like A WHORE-POV

LoyalFans 2 days ago

Humiliating My Sissy’s Tiny Cock Whilst Dominating His Boipussy

66% HD 0:39 / 16:26

Humiliating My Sissy’s Tiny Cock Whilst Dominating His Boipussy

FapHouse 5 months ago

30 Days Mtf Complete Transformation - Slut Training - Crossdressing - Bimbofication - Femdom POV

56% HD 0:39 / 10:01

30 Days Mtf Complete Transformation - Slut Training - Crossdressing - Bimbofication - Femdom POV

FapHouse 9 months ago

MILF1885 - Stepson to Sissy: A Femdom Transformation

64% HD 0:10 / 11:28

MILF1885 - Stepson to Sissy: A Femdom Transformation

LoyalFans 9 months ago

Trapped in my Body FOREVER

HD 0:10 / 19:50

Trapped in my Body FOREVER

LoyalFans 2 months ago

Sissy Humiliation: POV I do your nails

HD 0:10 / 15:07

Sissy Humiliation: POV I do your nails

LoyalFans 1 day ago

JOI Bwc Strapon Sph Transformation Sissification

JOI Bwc Strapon Sph Transformation Sissification

xHamster 1 year ago

No More Man! - Goddess Amber

65% HD 0:10 / 11:50

No More Man! - Goddess Amber

LoyalFans 4 months ago

Mistress Alexa's Sissy Academy

61% HD 1:01 / 8:17

Mistress Alexa's Sissy Academy

FapHouse 6 months ago

BISEXUAL BIMBOFICATION - Encouraged Bi Slut Training Transformation

46% HD 0:10 / 15:41

BISEXUAL BIMBOFICATION - Encouraged Bi Slut Training Transformation

LoyalFans 10 months ago

Sissy Training Part 2 - Oral

4K 0:39 / 38:08

Sissy Training Part 2 - Oral

FapHouse 4 weeks ago

Suck Your Friends Cock with Me

Suck Your Friends Cock with Me

FapHouse 2 days ago

Locktober - Cage 7: Businessman Transformed into Sissy by Seductive Mistress in Stylish Leather

Locktober - Cage 7: Businessman Transformed into Sissy by Seductive Mistress in Stylish Leather

JuicyVid 3 weeks ago

Gender Transformation Protocol

55% HD 0:10 / 12:02

Gender Transformation Protocol

LoyalFans 3 weeks ago

Your New Life as My Free Use Sissy

HD 1:01 / 16:13

Your New Life as My Free Use Sissy

FapHouse 1 week ago

The Happy Wife - After the Great Shift

The Happy Wife - After the Great Shift

XVideos 1 month ago

Transformation of the Sissy Gimp (HD)

HD 0:30 / 25:25

Transformation of the Sissy Gimp (HD)

Clips4sale 2 months ago

Ex Boyfriend to Sissy Girlfriend COMPLETE SERIES | Sissy Feminisation Transformation | Sophia Truee

50% HD 0:10 / 27:16

Ex Boyfriend to Sissy Girlfriend COMPLETE SERIES | Sissy Feminisation Transformation | Sophia Truee

LoyalFans 3 months ago

Te Transform in Tarfa Mea

63% HD 0:39 / 10:02

Te Transform in Tarfa Mea

FapHouse 10 months ago

Sissy bastinado in the medieval prison

Sissy bastinado in the medieval prison

xHamster 1 month ago

Reject you and transforming into my reward-pig cuck!

HD 1:01 / 10:03

Reject you and transforming into my reward-pig cuck!

FapHouse 3 years ago

Gender Transformation Bundle

Gender Transformation Bundle

Clips4sale 2 weeks ago

Sissification and Submission: Tormenting with the Vacuum Pump and Emasculating Control

43% HD 0:10 / 20:17

Sissification and Submission: Tormenting with the Vacuum Pump and Emasculating Control

LoyalFans 1 year ago

Foot Worship Feminization

Foot Worship Feminization

LoyalFans 2 months ago

Milked & Bred: Mistress Stellina Obscura Humiliates Husband with Sissy Hucow Transformation, Milking, Pegging & Toilet Play

69% HD 0:10 / 1:01:27

Milked & Bred: Mistress Stellina Obscura Humiliates Husband with Sissy Hucow Transformation, Milking, Pegging & Toilet Play

LoyalFans 11 months ago

Domestic Servitude - Part 1 **MOV**

4K 0:38 / 10:33

Domestic Servitude - Part 1 **MOV**

Clips4sale 2 years ago

Recapture : The FemDom New World Order : English Mistress In Military Latex Describes The NWO Female Supremacy FemDom Female Domination Milking Punish

57% HD 0:10 / 9:39

Recapture : The FemDom New World Order : English Mistress In Military Latex Describes The NWO Female Supremacy FemDom Female Domination Milking Punish

LoyalFans 10 months ago

Day 4 of Sissy Training - Lips for Sucking Not Talking

HD 0:39 / 23:03

Day 4 of Sissy Training - Lips for Sucking Not Talking

FapHouse 1 month ago

Gender transformation humiliation tease (1080p wmv)

50% HD 0:11 / 13:13

Gender transformation humiliation tease (1080p wmv)

Clips4sale 3 years ago

Sissy Date Night Makeover

Sissy Date Night Makeover

LoyalFans 1 week ago

Sissy Secretary: Mistress Gets Slut Ready for Job Interview with Feminization, Pegging & **** FULL-LENGTH

58% HD 0:10 / 47:44

Sissy Secretary: Mistress Gets Slut Ready for Job Interview with Feminization, Pegging & **** FULL-LENGTH

LoyalFans 1 year ago

Zur Sissy-Nutte abgerichtet

53% HD 0:10 / 6:43

Zur Sissy-Nutte abgerichtet

LoyalFans 1 year ago

U're a Floozy: feminization pov with sex therapist

U're a Floozy: feminization pov with sex therapist

Lesbian8 3 weeks ago

Your Last Ejaculation Ever! After? You Become My Latex Object Wife - Mistress Julia feat. Sukeban

59% 4K 0:10 / 17:52

Your Last Ejaculation Ever! After? You Become My Latex Object Wife - Mistress Julia feat. Sukeban

LoyalFans 5 months ago

Girlfriend Whitney Morgan Transforms YOU In To A Woman

58% HD 0:10 / 16:12

Girlfriend Whitney Morgan Transforms YOU In To A Woman

LoyalFans 4 years ago

YOU're a Whore: feminization pov with sex therapist

YOU're a Whore: feminization pov with sex therapist

PornFreeNow 3 weeks ago

Transformation Into Big Red Lips Bimbo

Transformation Into Big Red Lips Bimbo

xHamster 1 year ago

30 days MTF complete transformation - Faggot training - Crossdressing - Bimbofication - Femdom pov - Sissy slut - blonde - Mistress

60% HD 0:10 / 9:57

30 days MTF complete transformation - Faggot training - Crossdressing - Bimbofication - Femdom pov - Sissy slut - blonde - Mistress

LoyalFans 9 months ago

Feminization, Crossdressing & Sissification

Feminization, Crossdressing & Sissification

xHamster 1 month ago

Sissy Secretary Part 3 of 3: Mistress Stellina Makes Sissy Whore Milk Hard with Pegging & ****

58% HD 0:10 / 8:27

Sissy Secretary Part 3 of 3: Mistress Stellina Makes Sissy Whore Milk Hard with Pegging & ****

LoyalFans 1 year ago

Sissy Fuck Doll Inhale

75% HD 1:01 / 16:32

Sissy Fuck Doll Inhale

FapHouse 1 year ago

Sissy Training - Teaching My Friend How to Give a Blowjob

57% HD 0:39 / 29:53

Sissy Training - Teaching My Friend How to Give a Blowjob

FapHouse 1 year ago

Transformation Into Big Red Lips Bimbo

46% HD 1:01 / 7:29

Transformation Into Big Red Lips Bimbo

FapHouse 1 year ago

Feminization Home Girl Summer

58% 0:14 / 12:58

Feminization Home Girl Summer

Clips4sale 2 years ago

“New Year, New Girl” - 2026 Feminization Guide

HD 0:10 / 13:43

“New Year, New Girl” - 2026 Feminization Guide

LoyalFans 3 weeks ago

Lady Scarlet - a Hard Sissy Training - Part 1 - Un Duro Allenamento Da Sissy - Parte 1

HD 0:39 / 22:46

Lady Scarlet - a Hard Sissy Training - Part 1 - Un Duro Allenamento Da Sissy - Parte 1

FapHouse 2 years ago

Episode 2: Part 1: a Transformed Life: New Sissy Sexuality - Maitresse Julia

61% HD 0:39 / 13:19

Episode 2: Part 1: a Transformed Life: New Sissy Sexuality - Maitresse Julia

FapHouse 1 year ago

MTF: Unleash your inner slut

60% 0:19 / 31:48

MTF: Unleash your inner slut

Clips4sale 2 years ago

The Lust of Sissy 3D Saga - Supportive Sugardaddy

47% HD 1:01 / 12:03

The Lust of Sissy 3D Saga - Supportive Sugardaddy

FapHouse 11 months ago

Caged Sissy Cuck in Training

HD 0:10 / 14:12

Caged Sissy Cuck in Training

LoyalFans 6 months ago

Day 4 of Sissy Training - Lips for Sucking Not Talking

57% HD 1:01 / 23:03

Day 4 of Sissy Training - Lips for Sucking Not Talking

FapHouse 1 month ago

Betamorphosissy

HD 1:01 / 32:22

Betamorphosissy

FapHouse 3 years ago

Teaching you to be the perfect sissy slut: A strap-on fucking demonstration with Matriarch Ezada Sinn, Giada da Vinci and Their fetish girl, Lilla Gra

HD 0:10 / 17:17

Teaching you to be the perfect sissy slut: A strap-on fucking demonstration with Matriarch Ezada Sinn, Giada da Vinci and Their fetish girl, Lilla Gra

LoyalFans 1 year ago

Turning you into my sissy slut

65% 4K 0:30 / 11:29

Turning you into my sissy slut

Clips4sale 4 years ago

TEASER - The Bimbo Diagnosis - Your Fate as a Sissy Whore Is Sealed! Chastity, Strap On, Tied Up in Slavery and BRED Like A BITCH-POV The Bimbo Diagnos

TEASER - The Bimbo Diagnosis - Your Fate as a Sissy Whore Is Sealed! Chastity, Strap On, Tied Up in Slavery and BRED Like A BITCH-POV The Bimbo Diagnos

Dafreeporn 6 days ago

ULTIMATE SISSY DIAPER SLUT TRAINING for step-Daddy Dick

50% HD 0:10 / 34:12

ULTIMATE SISSY DIAPER SLUT TRAINING for step-Daddy Dick

LoyalFans 1 month ago

Two Alien Dommes Using Their Newly Transformed Alien Rubber Doll Slut

64% HD 1:01 / 11:25

Two Alien Dommes Using Their Newly Transformed Alien Rubber Doll Slut

FapHouse 1 year ago

Diapered & Humilliated Sissy Glory Hole Whore

HD 0:10 / 14:22

Diapered & Humilliated Sissy Glory Hole Whore

LoyalFans 1 year ago

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