Sissy Dress Up (5,157)

The best and newest sissy dress up videos

Shivering and Leaking of Lust and Frustration! - Chastity, Sissy Training, Pantyhose and Orgasm Denial with Miss Adrastea

68% HD 1:01 / 11:28

Shivering and Leaking of Lust and Frustration! - Chastity, Sissy Training, Pantyhose and Orgasm Denial with Miss Adrastea

FapHouse 2 months ago

Turning You Into My Sissy Slut

Turning You Into My Sissy Slut

XHamster 2 weeks ago

Dominant Girlfriend Turns You Into a Proper Sissy Slut Whore

Dominant Girlfriend Turns You Into a Proper Sissy Slut Whore

XHamster 3 months ago

Femboy and Vilu Vidish Compilation

68% HD 0:39 / 1:05:58

Femboy and Vilu Vidish Compilation

FapHouse 2 months ago

Milking the Sissy

Milking the Sissy

XHamster 5 months ago

Girls Night In: Dressing My Sissy Up & Talking About Boys

51% HD 0:10 / 6:13

Girls Night In: Dressing My Sissy Up & Talking About Boys

LoyalFans 3 months ago

Husband Gets Sissified

58% HD 0:10 / 26:36

Husband Gets Sissified

LoyalFans 4 months ago

Sissified by Step-Mommy

59% HD 0:15 / 13:28

Sissified by Step-Mommy

IWantClips 2 months ago

I want to make you my satin slut sissy

55% 0:19 / 22:49

I want to make you my satin slut sissy

Clips4sale 1 year ago

Fucked Like A Girl

65% HD 0:10 / 14:43

Fucked Like A Girl

LoyalFans 3 years ago

Boyfriend to Girlfriend Pt. 2: Sissified

56% HD 1:01 / 13:47

Boyfriend to Girlfriend Pt. 2: Sissified

FapHouse 4 years ago

Sissy bride chastity- Wedding night tease

67% HD 0:15 / 12:31

Sissy bride chastity- Wedding night tease

IWantClips 2 years ago

POV Cuckold volume 60

POV Cuckold volume 60

XHamster 1 month ago

Baby Boy No More! - Goddess Amber

56% HD 0:10 / 11:50

Baby Boy No More! - Goddess Amber

LoyalFans 2 years ago

Humiliating the sissy slut

60% HD 0:10 / 21:30

Humiliating the sissy slut

LoyalFans 2 months ago

I will transform you into the perfect sissy girl

I will transform you into the perfect sissy girl

XHamster 3 years ago

1st Sissy Experience With Miss Shell

53% HD 0:10 / 23:00

1st Sissy Experience With Miss Shell

LoyalFans 4 months ago

Girls Night In: Dressing My Sissy Up & Talking About Boys

69% HD 0:29 / 6:13

Girls Night In: Dressing My Sissy Up & Talking About Boys

IWantClips 2 months ago

Male to Feminized Sissy Bondage Transformation

59% 0:12 / 12:32

Male to Feminized Sissy Bondage Transformation

Clips4sale 2 years ago

Spanksgiving With The Family

70% 4K 1:56 / 36:00

Spanksgiving With The Family

TeamSkeet 9 years ago

Hot Wife Kissing & Stripping With Hot Sissy Tongue Sucking

Hot Wife Kissing & Stripping With Hot Sissy Tongue Sucking

XHamster 4 years ago

Pink Dressed Cucked Tight Femdom Sissy ASMR JOI BINAURAL BRAINWAVES

Pink Dressed Cucked Tight Femdom Sissy ASMR JOI BINAURAL BRAINWAVES

XHamster 1 week ago

BBC Cuckolding and C*oerced Bi Humiliation

54% HD 0:10 / 49:03

BBC Cuckolding and C*oerced Bi Humiliation

LoyalFans 2 years ago

I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI

I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI

Lesbian8 1 year ago

Blonde Teen and Black Bull

Blonde Teen and Black Bull

Some.Porn 2 years ago

Cuckold sissys wife all clothed up in underware and heels

Cuckold sissys wife all clothed up in underware and heels

Lesbian8 4 weeks ago

Your Bully Bimbotized Us WMV - MILF StepMom Lacey Royce Has Been Turned Into A Slutty Bimbo By Your Bully - Mesmerizing Mind Fuck Transformation Slut Training Fantasy

4K 1:00 / 25:12

Your Bully Bimbotized Us WMV - MILF StepMom Lacey Royce Has Been Turned Into A Slutty Bimbo By Your Bully - Mesmerizing Mind Fuck Transformation Slut Training Fantasy

Clips4sale 1 year ago

Trained To Be My Rubber Sissy Slut (WMV)

71% 0:30 / 12:45

Trained To Be My Rubber Sissy Slut (WMV)

Clips4sale 2 years ago

Training My Sissy Into Taking REAL COCK

HD 0:10 / 30:28

Training My Sissy Into Taking REAL COCK

LoyalFans 1 year ago

Pretty Sissy Spitroast with Elle Eros Hasmik JOI and Clara Dee POV

HD 0:14 / 12:22

Pretty Sissy Spitroast with Elle Eros Hasmik JOI and Clara Dee POV

IWantClips 2 years ago

Making My Husband into a Cuckold Sissy!

49% 0:11 / 9:49

Making My Husband into a Cuckold Sissy!

Clips4sale 2 years ago

Our New Toy - Part 3

60% HD 0:25 / 22:05

Our New Toy - Part 3

Clips4sale 3 years ago

Sissy Tutorial

HD 0:25 / 16:56

Clips4sale 3 years ago

1st Sissy Experience With Miss Shell

65% HD 0:10 / 23:00

1st Sissy Experience With Miss Shell

LoyalFans 2 years ago

SISSY DRESS UP

65% 0:30 / 9:04

Clips4sale 1 year ago

1st Sissy Experience With Miss Shell 4k

1st Sissy Experience With Miss Shell 4k

Clips4sale 3 years ago

Sissy bride chastity - Wedding night tease

HD 0:10 / 12:32

Sissy bride chastity - Wedding night tease

LoyalFans 1 year ago

ACT ON YOUR SISSY FAGGOT FANTASIES 1080P - ELLIE IDOL

ACT ON YOUR SISSY FAGGOT FANTASIES 1080P - ELLIE IDOL

LoyalFans 1 week ago

You are going to be my new sissy boy slut

You are going to be my new sissy boy slut

XHamster 11 years ago

Dressing up Sissy

55% HD 0:39 / 10:15

Dressing up Sissy

FapHouse 1 year ago

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

64% HD 0:10 / 9:57

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

LoyalFans 1 year ago

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

44% HD 1:01 / 10:01

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

FapHouse 1 year ago

JOI Echo in Latex with My Big Black Strapon - Luna Doll

58% 0:39 / 25:09

JOI Echo in Latex with My Big Black Strapon - Luna Doll

FapHouse 10 months ago

From Ugly Boy to Pretty Girl: A Total Sissy Transformation

62% HD 0:10 / 34:44

From Ugly Boy to Pretty Girl: A Total Sissy Transformation

LoyalFans 4 weeks ago

Girls Night Out

Girls Night Out

XHamster 5 months ago

INEEDAMOMMY Diapered, Sissified and PEGGED by Ginary and Bailey!

INEEDAMOMMY Diapered, Sissified and PEGGED by Ginary and Bailey!

Clips4sale 2 years ago

[F4A] Doll's Don't Move ~ Cruel Femdom Dollification and Hyper Feminization Audio Roleplay

[F4A] Doll's Don't Move ~ Cruel Femdom Dollification and Hyper Feminization Audio Roleplay

PornFreeNow 1 year ago

Mature MILF Try On Haul From Demure to Red Hot Dresses

Mature MILF Try On Haul From Demure to Red Hot Dresses

XHamster 1 year ago

Sissy training and feminisation: A Feminine makeover for Miss Dayana’s chattel

57% HD 0:10 / 8:50

Sissy training and feminisation: A Feminine makeover for Miss Dayana’s chattel

LoyalFans 2 months ago

Sissy sluts swirlies and pegging humiliation

63% HD 0:10 / 11:43

Sissy sluts swirlies and pegging humiliation

LoyalFans 11 months ago

Moan for Mommy like a good girl 💜Eye Contact, Dress-Up & Slut Fingering

HD 0:10 / 10:20

Moan for Mommy like a good girl 💜Eye Contact, Dress-Up & Slut Fingering

LoyalFans 3 months ago

Dildo Dolly 2

Clips4sale 3 years ago

Becoming My Sissy Maid

HD 0:24 / 16:07

Becoming My Sissy Maid

IWantClips 2 months ago

Sissy Maid Holds His Hot Wife Mibby Legs Wide Open For Alpha Bull Action

HD 0:31 / 16:41

Sissy Maid Holds His Hot Wife Mibby Legs Wide Open For Alpha Bull Action

Clips4sale 1 month ago

Mommy Domme in Leather Loans Out Her Sissy Boy Role Play

Mommy Domme in Leather Loans Out Her Sissy Boy Role Play

XHamster 3 weeks ago

No More Man! - Goddess Amber

64% HD 0:10 / 11:50

No More Man! - Goddess Amber

LoyalFans 10 months ago

divinebitches - penny barber marcelo pretty sissy slave in pink

divinebitches - penny barber marcelo pretty sissy slave in pink

BDSMShip 2 years ago

JOI Echo With My Big Black Dick - Luna Doll

JOI Echo With My Big Black Dick - Luna Doll

XHamster 10 months ago

Caught with a Camera

Caught with a Camera

XHamster 2 years ago

JOI Echo in Latex with My Big Black Strapon - Luna Doll

JOI Echo in Latex with My Big Black Strapon - Luna Doll

XHamster 9 months ago

Eat It Sissy - Audio Humiliation

Eat It Sissy - Audio Humiliation

FapHouse 2 months ago

Made to Be a Slut and Feminized by the Birthday Girl

54% HD 1:01 / 11:17

Made to Be a Slut and Feminized by the Birthday Girl

FapHouse 10 months ago

Call me Daddy Domme

62% HD 0:10 / 11:54

Call me Daddy Domme

LoyalFans 2 years ago

Cuck Confessions Part 9! The Sissy Cuck : Adreena Winters Convinces Russian QOS She Needs A Real Man!

59% HD 0:33 / 35:28

Cuck Confessions Part 9! The Sissy Cuck : Adreena Winters Convinces Russian QOS She Needs A Real Man!

Clips4sale 9 months ago

Sissy Training Compilation

57% HD 0:10 / 27:19

Sissy Training Compilation

LoyalFans 6 months ago

Take Your Cum Facial - Sissy Bi Encouragement - Cumslut Training

Take Your Cum Facial - Sissy Bi Encouragement - Cumslut Training

XHamster 6 months ago

WVM - PART 194 - Skye Opens Up By MissKitty2K

WVM - PART 194 - Skye Opens Up By MissKitty2K

HentaiGem 1 year ago

NEW - Witch Reads Your Mind and Discovers You're a Secret Sissy

61% HD 0:10 / 8:56

NEW - Witch Reads Your Mind and Discovers You're a Secret Sissy

LoyalFans 4 months ago

Up Sissys dress

Up Sissys dress

XHamster 2 weeks ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

XHamster 2 years ago

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

59% HD 0:39 / 16:47

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

FapHouse 1 month ago

Confess that you are a sissy to your best friend!

Confess that you are a sissy to your best friend!

XHamster 1 month ago

Exposing My Sissy Best Friend- Goddess Rosie Reed Exposes Her Sissy Best Friend- Ebony Femdom Sissy Training

75% HD 1:01 / 5:45

Exposing My Sissy Best Friend- Goddess Rosie Reed Exposes Her Sissy Best Friend- Ebony Femdom Sissy Training

FapHouse 3 months ago

Cow Girl for Sissy

61% HD 1:01 / 15:40

Cow Girl for Sissy

FapHouse 2 months ago

Sissy Phoenix Marie fills Aubrey Kate's mouth with cum

Sissy Phoenix Marie fills Aubrey Kate's mouth with cum

MegaTube 5 years ago

Dildo Dolly 2

58% HD 1:01 / 15:31

FapHouse 3 years ago

Shivering and Leaking of Lust and Frustration! - Chastity, Sissy Training, Pantyhose and Orgasm Denial with Miss Adrastea

50% HD 0:39 / 11:28

Shivering and Leaking of Lust and Frustration! - Chastity, Sissy Training, Pantyhose and Orgasm Denial with Miss Adrastea

FapHouse 2 months ago

Lost The Bet Sissy Dress Up

Lost The Bet Sissy Dress Up

Eporner 5 months ago

Simply Sensual Evening Sex in Vintage Lingerie Ended with Bukkake

Simply Sensual Evening Sex in Vintage Lingerie Ended with Bukkake

XHamster 3 years ago

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

65% HD 1:01 / 16:47

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

FapHouse 1 month ago

Romantic Evening Nylon Sex in White Lingerie

Romantic Evening Nylon Sex in White Lingerie

XHamster 3 years ago

amber blank - bi cuck sissy

amber blank - bi cuck sissy

PornOne 6 years ago

Becoming a sissy

Becoming a sissy

FreePorn8 6 years ago

Girls Night Out

50% HD 0:39 / 25:52

Girls Night Out

FapHouse 6 months ago

Sissy Date Night

Sissy Date Night

FapHouse 1 month ago

Long Minet and Creampie In Black Nylon Lingerie

Long Minet and Creampie In Black Nylon Lingerie

XHamster 4 years 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

Rosies Sissification

59% HD 1:01 / 11:09

Rosies Sissification

FapHouse 1 year ago

Therapist-Fantasy Dresses Sissy Part 1

61% HD 0:10 / 12:31

Therapist-Fantasy Dresses Sissy Part 1

LoyalFans 5 months ago

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

XHamster 1 month ago

POV Cuckold volume 60

POV Cuckold volume 60

SortPorn 1 month ago

Secret Sissy Fantasy- Mistress Kendra, femdom, chastity, make me bi

HD 0:37 / 11:26

Secret Sissy Fantasy- Mistress Kendra, femdom, chastity, make me bi

IWantClips 1 year ago

A Hole Fucking Reward for My Sissy Maid- Dominatrix Goddess Rosie Reed- 1080p HD

50% HD 0:39 / 8:02

A Hole Fucking Reward for My Sissy Maid- Dominatrix Goddess Rosie Reed- 1080p HD

FapHouse 2 months ago

Sissy Training in the Dungeon

55% HD 0:10 / 13:29

Sissy Training in the Dungeon

LoyalFans 2 years ago

Sissy Slut made ready for Mistress (4K)

4K 0:10 / 12:06

Sissy Slut made ready for Mistress (4K)

LoyalFans 1 month ago

Petite Ma'am fucking her pink sissy maid in chastity

Petite Ma'am fucking her pink sissy maid in chastity

XHamster 3 years ago

Sissy Transformation and Training Go Girly and suck cock! Goddess Vivien guides you to get dressed in a frilly pink sissy outfit and suck dick

53% HD 0:10 / 15:31

Sissy Transformation and Training Go Girly and suck cock! Goddess Vivien guides you to get dressed in a frilly pink sissy outfit and suck dick

LoyalFans 1 year ago

Lick this mans cum off my pussy, cuckold

Lick this mans cum off my pussy, cuckold

3Movs 1 year ago

you in My nightgown

56% HD 0:15 / 8:54

you in My nightgown

IWantClips 2 months ago

Cucked & Feminized by a Hot Alpha Couple Sissy Humiliation Fantasy

64% HD 1:01 / 10:53

Cucked & Feminized by a Hot Alpha Couple Sissy Humiliation Fantasy

FapHouse 5 months ago

Chaste & Sissified

43% HD 0:10 / 7:19

Chaste & Sissified

LoyalFans 2 months ago

Your Lesbian Wife Sissifies and Pegs You

HD 0:10 / 21:51

Your Lesbian Wife Sissifies and Pegs You

LoyalFans 1 week ago

I will dress you up like one of my dolls

I will dress you up like one of my dolls

XHamster 4 years ago

My very own sissy maid!

My very own sissy maid!

XHamster 3 months ago

Eat From a Bowl, Lick My Boots, Suck Cock

Eat From a Bowl, Lick My Boots, Suck Cock

XHamster 2 weeks ago

I will prepare you for a night out as a sissy

I will prepare you for a night out as a sissy

XHamster 3 years ago

I am a Dirty Slut: Foot Licking & Sissification

I am a Dirty Slut: Foot Licking & Sissification

IWantClips 2 months ago

Compilation of tied up man getting fisted and pegged

Compilation of tied up man getting fisted and pegged

XGroovy 1 year ago

Milking the Sissy

Milking the Sissy

XHamster 4 months ago

Pegging and Glove Fissting Latex Sissy

HD 0:10 / 31:45

Pegging and Glove Fissting Latex Sissy

LoyalFans 3 years ago

Catsuit Teaches Sissy Maid

Catsuit Teaches Sissy Maid

BDSMX 4 years ago

Stepmom Takes A Bath in Stockings and Sexy Lingerie, Wet Big Ass

Stepmom Takes A Bath in Stockings and Sexy Lingerie, Wet Big Ass

XHamster 1 month ago

JOI Echo in Latex with My Big Black Strapon - Luna Doll

64% 1:01 / 25:09

JOI Echo in Latex with My Big Black Strapon - Luna Doll

FapHouse 10 months ago

Dressed up for the Gangbang

HD 0:10 / 20:20

Dressed up for the Gangbang

LoyalFans 1 week ago

Best of Sissy Slut Pegging: Strapon Fucking Compilation

Best of Sissy Slut Pegging: Strapon Fucking Compilation

XHamster 2 years ago

Custom Clip: You Become the Office Bitch

Custom Clip: You Become the Office Bitch

XHamster 2 years ago

Sissy cuckold in chastity sharing his wife. Cuckold confession with Adreena Winters

HD 0:31 / 35:47

Sissy cuckold in chastity sharing his wife. Cuckold confession with Adreena Winters

IWantClips 2 months ago

Dressed to Be My Dirty Girl

61% HD 0:39 / 10:10

Dressed to Be My Dirty Girl

FapHouse 1 week ago

Sissy Cumslut Training - Take Your Cum Facial

Sissy Cumslut Training - Take Your Cum Facial

FapHouse 1 year ago

Sissy dressing up

Sissy dressing up

PornFreeNow 1 week ago

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5,157 results found

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