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Sissy Transformation (12,226)

Sissy Slobs a Fat Rod and Swallows a Load

Sissy Slobs a Fat Rod and Swallows a Load

Jizzberry 4 years ago

One last cigarette before hitting the bedroom

One last cigarette before hitting the bedroom

XHamster 8 months ago

Miss Lilly, the Lady of the Manor, along with Miss Bella Bouvier and Miss Lola Milk, the two devoted governesses, embark on a full makeover sissy transformation of the new boy in the manor. Watch as he begins his journey to become a pretty girl, collared

60% HD 0:29 / 23:10

Miss Lilly, the Lady of the Manor, along with Miss Bella Bouvier and Miss Lola Milk, the two devoted governesses, embark on a full makeover sissy transformation of the new boy in the manor. Watch as he begins his journey to become a pretty girl, collared

Clips4sale 8 months ago

AI Generated Storm Tranny Babe rides enemy monster cock

AI Generated Storm Tranny Babe rides enemy monster cock

XHamster 7 months ago

Shemale Disney Princess, Gangbang Orgy Party Big Dicks Lots Of cum AI GENERATED

Shemale Disney Princess, Gangbang Orgy Party Big Dicks Lots Of cum AI GENERATED

XHamster 4 months ago

Sissy Mantras

65% HD 0:10 / 7:38

LoyalFans 7 months ago

November 2025 Video Trailers - Katy Churchill farting, pissing, balloons, simp, smoking, facesitting

November 2025 Video Trailers - Katy Churchill farting, pissing, balloons, simp, smoking, facesitting

XHamster 10 months ago

Bimbo rubber doll - Chastity and dick sucking

65% 0:30 / 9:47

Bimbo rubber doll - Chastity and dick sucking

Clips4sale 2 years ago

Total Sissy Amnesia

61% HD 0:30 / 13:15

Total Sissy Amnesia

Clips4sale 10 months ago

Trans Dr.Delora Veil : A Fetishist Bends Down for Luxurious Resort Pass

Trans Dr.Delora Veil : A Fetishist Bends Down for Luxurious Resort Pass

XHamster 7 months ago

Girl Transformation Complete: Sissy Breeding with Dommy Rose

57% HD 0:10 / 21:29

Girl Transformation Complete: Sissy Breeding with Dommy Rose

LoyalFans 10 months ago

Hotwife feminized and dominated small cock sissy husband

Hotwife feminized and dominated small cock sissy husband

XHamster 7 months ago

I'll fuckin' help you become the sissy mega-slut you were meant to be, you fuckin' pixie! I'll guide you thru your fuckin' transformation and make you my lil' sissy bi-atch, you fuckin' faggot! (FEMINIZATION ROLEPLAY - AI GENER

I'll fuckin' help you become the sissy mega-slut you were meant to be, you fuckin' pixie! I'll guide you thru your fuckin' transformation and make you my lil' sissy bi-atch, you fuckin' faggot! (FEMINIZATION ROLEPLAY - AI GENER

HentaiGem 1 year ago

Sissy Super Bowl Loser: Good Boi Pup's Humiliation

Sissy Super Bowl Loser: Good Boi Pup's Humiliation

XHamster 1 year ago

Erectile Dysfunction + estrogen = From Man to Mouth Whore (bimbofication) 18 min (maledom)

51% HD 0:30 / 18:16

Erectile Dysfunction + estrogen = From Man to Mouth Whore (bimbofication) 18 min (maledom)

Clips4sale 1 year ago

Alisons hotel room transformation

Alisons hotel room transformation

XHamster 1 year ago

Sissytraining BBC Sluts Training! Goddess with big tits makes you a slut

Sissytraining BBC Sluts Training! Goddess with big tits makes you a slut

XHamster 2 years ago

The Lust of Sissy Boy - Concerns About My Boy Friend

41% HD 1:01 / 11:35

The Lust of Sissy Boy - Concerns About My Boy Friend

FapHouse 1 year ago

Smelly Slipper Sniffer

58% HD 0:30 / 11:10

Smelly Slipper Sniffer

Clips4sale 1 year ago

The Transformation of Dakota Burns

The Transformation of Dakota Burns

Some.Porn 2 years ago

Jasmine_dlight & Peggy Deville & Bambi Brat - Impaling the Brat on Two Fuck Machines

HD 0:39 / 16:24

Jasmine_dlight & Peggy Deville & Bambi Brat - Impaling the Brat on Two Fuck Machines

FapHouse 3 months ago

Horny Sissy For Halloween - Extended Preview

Horny Sissy For Halloween - Extended Preview

XHamster 2 years ago

Bimbofied fuck doll

Bimbofied fuck doll

Clips4sale 5 years ago

Wear Sexy Dress Premium Esition

Wear Sexy Dress Premium Esition

XHamster 1 year ago

Sissy Cuckold Transformation

Sissy Cuckold Transformation

Dafreeporn 6 years ago

30 Days to Become a Barbie - Sissy Transformation

60% HD 0:24 / 12:54

30 Days to Become a Barbie - Sissy Transformation

Clips4sale 2 months ago

Feminization Sissification Sissy training - RESIGNED SISSY FAG

Feminization Sissification Sissy training - RESIGNED SISSY FAG

BigTitsLust 2 years ago

Sissy Humiliation Cum Eating Instructions Give It up You Are Gay

Sissy Humiliation Cum Eating Instructions Give It up You Are Gay

XHamster 2 weeks ago

LucyyLux fuels wild bareback anal blitz

LucyyLux fuels wild bareback anal blitz

ShemaleSex 1 month ago

Emasculated & Sissified

70% 0:16 / 12:52

Emasculated & Sissified

Clips4sale 1 year ago

The Wedding Night SIssification

The Wedding Night SIssification

Clips4sale 8 months ago

Amateur Texas Trans Sissy Molly Jade - Full Body Showcase, Chastity, Underware & Closeups Transgirlmolly731

Amateur Texas Trans Sissy Molly Jade - Full Body Showcase, Chastity, Underware & Closeups Transgirlmolly731

ShemaleSin 1 week ago

Kelly Michaels transformed and fucking

Kelly Michaels transformed and fucking

Tranny.one 3 years ago

Sissy Transformation Training – Miss Lilly & Sir Claire Turn You Into Their Pretty Doll and Footstool

64% HD 0:10 / 15:54

Sissy Transformation Training – Miss Lilly & Sir Claire Turn You Into Their Pretty Doll and Footstool

LoyalFans 6 months ago

Wife Makes You Her Mtf Sissy Slut Camwhore & Lesbian Lover

Wife Makes You Her Mtf Sissy Slut Camwhore & Lesbian Lover

XHamster 8 months ago

Becoming a sissy

Becoming a sissy

Dafreeporn 6 years ago

A Sissy's Perspective Ep.2 - BBstories - Sissy Caption Stories

A Sissy's Perspective Ep.2 - BBstories - Sissy Caption Stories

Eporner 1 year ago

Bimbo Transformation: Dominant Woman Takes Control

Bimbo Transformation: Dominant Woman Takes Control

XXXShake 3 years 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-Erziehung: So wurdest du noch nie gefickt!

Premium HD 9:47

Sissy-Erziehung: So wurdest du noch nie gefickt!

Clips4sale 2 months ago

Sissy prepared and transformed to serve shlong

Sissy prepared and transformed to serve shlong

ShemaleSin 5 years ago

Shaving and balls busting part 2

Shaving and balls busting part 2

XHamster 1 year ago

Sissy Slut Training CEI Goddess Patricia

Sissy Slut Training CEI Goddess Patricia

FapHouse 5 months ago

Roommate Helps Me Out - Sissy Caption Story

Roommate Helps Me Out - Sissy Caption Story

BigTitsLust 5 years ago

Lilly Benz transforms you into a hot and horny girl and fucks you hard in sissification POV

Lilly Benz transforms you into a hot and horny girl and fucks you hard in sissification POV

TrannyMovs 10 months ago

Sissy Compilation How Sissies Behave

Sissy Compilation How Sissies Behave

XHamster 2 months ago

U've been Transformed

U've been Transformed

Amateur8 4 years ago

Deep anal dildo riding by a big cock Tgirl

Deep anal dildo riding by a big cock Tgirl

XHamster 1 month ago

BNWO: EVOLVE OR BECOME EXTINCT - MistressRavenFD explains what life will be like for a little white boi sissy now that the BNWO has arrived

HD 0:30 / 17:41

BNWO: EVOLVE OR BECOME EXTINCT - MistressRavenFD explains what life will be like for a little white boi sissy now that the BNWO has arrived

IWantClips 3 months ago

Sissy Whore Transformation Machine

Sissy Whore Transformation Machine

Tranny.one 4 years ago

Boy feminized to a Sissy by shemale and hard fucked

Boy feminized to a Sissy by shemale and hard fucked

AShemaleTube 2 years ago

SISSIFICATION & Dude becomes BIG BLACK COCK's SLUT

SISSIFICATION & Dude becomes BIG BLACK COCK's SLUT

HentaiGem 1 year ago

Petite Trans Teen Fucks Cute Blonde Femboy Clip 1

Petite Trans Teen Fucks Cute Blonde Femboy Clip 1

XHamster 5 months ago

Your Owner Gives You Surgical Body Modifications

Your Owner Gives You Surgical Body Modifications

XHamster 5 days ago

Sissy Slut Gangbang Training

Sissy Slut Gangbang Training

XHamster 1 month ago

Fvr - 63 - Feminize Him 2 - Date 1 - Voyeur - Alex

44% VR 0:08 / 12:57

Fvr - 63 - Feminize Him 2 - Date 1 - Voyeur - Alex

FapHouse 2 weeks ago

becomingfemme - jenny kennedy tranny trained to be a good slut

becomingfemme - jenny kennedy tranny trained to be a good slut

TransDoe 2 years ago

Hot Muscular Futa Poilice and prisoner Public Sex AI Generated Clip 1

Hot Muscular Futa Poilice and prisoner Public Sex AI Generated Clip 1

XHamster 5 months ago

German Mistress Transforms Amateur into Sissy Slave

German Mistress Transforms Amateur into Sissy Slave

Jizzberry 5 years ago

wife crossdressing spouse

wife crossdressing spouse

FreePorn8 1 year ago

Sissy Training - Feminization

Sissy Training - Feminization

BigTitsLust 2 years ago

Crossdresser Chronicles: Embracing the Art of Transformation and Celebrating Individuality

Crossdresser Chronicles: Embracing the Art of Transformation and Celebrating Individuality

XHamster 1 year ago

Pimping You Out - Miss Faith Rae's Femdom POV Sissy Training Findom Debt Contract - HD 1080p MP4

Pimping You Out - Miss Faith Rae's Femdom POV Sissy Training Findom Debt Contract - HD 1080p MP4

XHamster 2 years ago

AI Generated Storm Tranny Babe rides enemy monster cock Clip 3

AI Generated Storm Tranny Babe rides enemy monster cock Clip 3

XHamster 7 months ago

1st Sissy Experience With Miss Shell

66% HD 0:10 / 23:00

1st Sissy Experience With Miss Shell

LoyalFans 2 years ago

Transform-process in a hotel in Berlin

Transform-process in a hotel in Berlin

FapHouse 2 months ago

Amateur Texas Treasure Trans Sissy Molly Jade - Full Body Showcase, Chastity, Underware & Closeups Transgirlmolly731

Amateur Texas Treasure Trans Sissy Molly Jade - Full Body Showcase, Chastity, Underware & Closeups Transgirlmolly731

ShemaleSin 5 days ago

Sissy UwU solo masturbation 39 mtf British Anal Masturbation Trans flat chastity cages toys

Sissy UwU solo masturbation 39 mtf British Anal Masturbation Trans flat chastity cages toys

XHamster 1 month ago

How I Destroyed My Cock (REAL Soft Cock Training) [MOV Format]

50% 1:00 / 10:40

How I Destroyed My Cock (REAL Soft Cock Training) [MOV Format]

Clips4sale 6 months ago

Foot Worship Feminization

Foot Worship Feminization

LoyalFans 10 months ago

Hose beauty full encased in hose feminizes and sissifies her hunk ally to nylon doxy

Hose beauty full encased in hose feminizes and sissifies her hunk ally to nylon doxy

Amateur8 4 years ago

Transforming you into my girlfriend - Miss Honour May - MP4 HD

55% HD 0:16 / 13:24

Transforming you into my girlfriend - Miss Honour May - MP4 HD

Clips4sale 2 years ago

For the Hesitant/Beginner Sissy

55% HD 0:15 / 11:36

For the Hesitant/Beginner Sissy

IWantClips 3 months ago

Great Tia Tizzianni Femboy Mtof Transformation & Feminization with Sissy Help Factors

63% HD 0:39 / 12:04

Great Tia Tizzianni Femboy Mtof Transformation & Feminization with Sissy Help Factors

FapHouse 1 year ago

Smoking JOI CEI

Smoking JOI CEI

XHamster 8 months ago

I Made You GAY for BBC Big Black Cock 30 minute AUDIO ASMR Encouraged bi

Premium HD 30:55

I Made You GAY for BBC Big Black Cock 30 minute AUDIO ASMR Encouraged bi

Clips4sale 1 year ago

Turning into a Girl! MTF TRANSformation Cock Fuck like Pussy

Turning into a Girl! MTF TRANSformation Cock Fuck like Pussy

XHamster 5 years ago

Vibrator & Anal JOI: Advanced Erectile Dysfunction Encouragement & Sissygasm Training

58% HD 0:10 / 30:21

Vibrator & Anal JOI: Advanced Erectile Dysfunction Encouragement & Sissygasm Training

LoyalFans 2 months ago

Make Him Bi Episode 5: Preparing His Holes For Real Cock With Sophia Sahara - Ultimate Bi Encouragement [UHD 4K]

73% 4K 0:29 / 15:35

Make Him Bi Episode 5: Preparing His Holes For Real Cock With Sophia Sahara - Ultimate Bi Encouragement [UHD 4K]

Clips4sale 1 year ago

Sissified and made to suck BBC - Ebony Goddess Luna Law feminises chastity sissy and orders her to give the muscled bull a sloppy blowjob,

HD 0:10 / 15:18

Sissified and made to suck BBC - Ebony Goddess Luna Law feminises chastity sissy and orders her to give the muscled bull a sloppy blowjob,

LoyalFans 3 weeks ago

Hubby Transformation Into Pink Shoes - Transformation Fantasy, Humiliation

50% HD 0:39 / 32:58

Hubby Transformation Into Pink Shoes - Transformation Fantasy, Humiliation

FapHouse 1 month ago

Checking Locked Dick and Strapon

Checking Locked Dick and Strapon

XHamster 2 years ago

Blake Fucking Young 18 Plus Sissy Gay Asshole Anal Sex

61% HD 0:39 / 7:04

Blake Fucking Young 18 Plus Sissy Gay Asshole Anal Sex

FapHouse 1 month ago

Cruel Threat Fantasy of Dominated Feminization and Beeing My Whore

74% HD 1:01 / 13:28

Cruel Threat Fantasy of Dominated Feminization and Beeing My Whore

FapHouse 2 years ago

Sissy Girl Mind Screw - Screw toy

Sissy Girl Mind Screw - Screw toy

KAMS 1 year ago

Dr Changes Your Gender – Wife-Signed Sissy Pussy Training

Premium HD 8:55

Dr Changes Your Gender – Wife-Signed Sissy Pussy Training

Clips4sale 2 weeks ago

Freaky gay boy

XHamster 4 months ago

Ken Prince Lets Himself Be Morbid with His College Classmate

56% HD 1:01 / 7:55

Ken Prince Lets Himself Be Morbid with His College Classmate

FapHouse 8 months ago

Watch Pornhub transform me into a hot, newbie, featuring shemale, music, and ass fucking machines!

Watch Pornhub transform me into a hot, newbie, featuring shemale, music, and ass fucking machines!

TrannyMovs 6 days ago

Femdom Gangbang: Sissy Boyfriend Feminization & Pegging (FULL)

60% HD 0:10 / 36:14

Femdom Gangbang: Sissy Boyfriend Feminization & Pegging (FULL)

LoyalFans 2 months ago

Vivienne L'amour - Suffer for Me Sissy

Vivienne L'amour - Suffer for Me Sissy

XHamster 1 month ago

The Cleaner: A Sissy Caption story

The Cleaner: A Sissy Caption story

Amateur8 4 years ago

Your Clitty Is Mine to Lock

Your Clitty Is Mine to Lock

FapHouse 10 months ago

Sissy CEI Suck your Panties Clean SLUT

52% HD 0:28 / 8:48

Sissy CEI Suck your Panties Clean SLUT

Clips4sale 2 years ago

Your Affirming Makeover (WMV)

Your Affirming Makeover (WMV)

Clips4sale 4 years ago

LGBTQ Couple New Apartment Blowjob Threesome with neighbour AI GENERATED Clip 1

LGBTQ Couple New Apartment Blowjob Threesome with neighbour AI GENERATED Clip 1

XHamster 4 months ago

FEMINIZED 1 month as my wife

FEMINIZED 1 month as my wife

Clips4sale 4 weeks ago

Femdom: Sissy Feminization!

Femdom: Sissy Feminization!

Amateur8 3 years ago

Turning You Into My Doll

58% 0:26 / 7:04

Turning You Into My Doll

Clips4sale 2 years ago

Cummy Classroom Sissy Slut Tgirl Panty Loads

58% 0:11 / 14:08

Cummy Classroom Sissy Slut Tgirl Panty Loads

Clips4sale 3 years ago

Sissy Voodoo Doll 2

Sissy Voodoo Doll 2

LoyalFans 1 week ago

Fat Piggy Activation Part 2

Fat Piggy Activation Part 2

XHamster 5 months ago

SISSYMAID CHASTITY MESMERIZE - Compelled Chastity Training [Chastity Device] [Chastity Belt] [Male Chastity] [Chastity Cage] [Locked] [Keyholder] [Chastity Keyholder] [Locktober] [Locked In Chastity]

SISSYMAID CHASTITY MESMERIZE - Compelled Chastity Training [Chastity Device] [Chastity Belt] [Male Chastity] [Chastity Cage] [Locked] [Keyholder] [Chastity Keyholder] [Locktober] [Locked In Chastity]

Clips4sale 2 years ago

Sissy Clitty Affirmations

49% HD 1:01 / 9:15

Sissy Clitty Affirmations

FapHouse 5 months ago

PREGNANT SISSY - MIND TRAINING

65% HD 0:10 / 16:21

PREGNANT SISSY - MIND TRAINING

LoyalFans 7 months ago

Sissification, Pegging, Licking Dirty Shoes and Smelly Armpits, Humiliation

Sissification, Pegging, Licking Dirty Shoes and Smelly Armpits, Humiliation

XHamster 2 months ago

Feminization: Your fresh life as Sissy - Ep4 Turning this Wanker into a Slave - Mistress Julia

Feminization: Your fresh life as Sissy - Ep4 Turning this Wanker into a Slave - Mistress Julia

MyTransfix 2 months ago

Sissy Boyfriend Found Out and Pegged

60% HD 0:10 / 18:38

Sissy Boyfriend Found Out and Pegged

LoyalFans 3 years ago

Midnight Chair: Barber’s Sissy Makeover Claim

Midnight Chair: Barber’s Sissy Makeover Claim

Clips4sale 5 days ago

Husband Gets Sissified

58% HD 0:10 / 26:36

Husband Gets Sissified

LoyalFans 5 months ago

Sissy Caption Story: Rare Mutation - More than a friend

Sissy Caption Story: Rare Mutation - More than a friend

Eporner 1 year ago

Sissy faggot husband gets fucked in his ass

Sissy faggot husband gets fucked in his ass

XHamster 1 year ago

Erotic Humiliation

46% HD 1:01 / 51:56

Erotic Humiliation

FapHouse 9 months ago

BODY SWAP into bound slut - part 2

41% HD 0:30 / 6:41

BODY SWAP into bound slut - part 2

Clips4sale 1 year ago

Sasha De Sade's BDSM training ends in a hot and heavy humiliation session

Sasha De Sade's BDSM training ends in a hot and heavy humiliation session

TrannyMovs 9 months ago

Strapon on the way home from the cinema

Strapon on the way home from the cinema

XHamster 2 years ago

1st Sissy Experience With Miss Shell 4k

1st Sissy Experience With Miss Shell 4k

Clips4sale 3 years ago

Hinako's First Female Suit Experience (Male Version)!

62% HD 0:11 / 15:17

Hinako's First Female Suit Experience (Male Version)!

Clips4sale 5 years ago

Bi Cuckold Transformation

Bi Cuckold Transformation

Clips4sale 1 year ago

Lexi Made Sissy - Lexi Luna

Lexi Made Sissy - Lexi Luna

XHamster 8 months ago

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