Crossdressing (1,508)

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Transforming You into My Sweet, Short, Pantiless Maid

LoyalFans 1 year ago

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Do You Really Want to Fuck Your Mother?

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Do You Really Want to Fuck Your Mother?

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You Bet Your Ass

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Your Roommate Encourages You to Dress Up for Hot Play

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You Bet Your Ass

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LoyalFans 1 year ago

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PissVids 2 years ago

Let's Change Gender Roles and Spice Up Our Play

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xHamster 2 years ago

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APClips 11 months ago

Sissy Boyfriend Found Out and Pegged

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LoyalFans 1 month ago

I Can't Believe I'm Babysitting a 21-Year-Old Virgin

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LoyalFans 2 years ago

Sissy Boyfriend Found Out and Pegged

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Sissy Boyfriend Found Out and Pegged

LoyalFans 2 years ago

Your Roommate Encourages You to Dress Up for Hot Play

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LoyalFans 8 months ago

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LoyalFans 1 year ago

Humbled Sissy Gets a 72 Stroke Caning from Nikki Whiplash (WL1779)

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LoyalFans 3 weeks ago

Ladies Night - Part(y) 3

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Ladies Night - Part(y) 3

APClips 11 months ago

Pantyhose Pumping Pansy

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LoyalFans 11 months ago

New Year Of Sissy Training

65% HD 0:10 / 13:30

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LoyalFans 2 weeks ago

The hot girls next door - Encouraged sissy

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LoyalFans 1 day ago

Sissy Slut Task

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LoyalFans 2 years ago

Sissification School

66% HD 0:10 / 11:29

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LoyalFans 4 months ago

Therapy-Fantasy For Pussies

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LoyalFans 9 months ago

Sissy Husband In Satin

71% 0:10 / 10:25

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APClips 9 months ago

Mistress Jewell's Bound Hooker pt2

66% HD 0:10 / 12:50

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LoyalFans 2 years ago

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PissVids 3 years ago

7 Mini Skirts

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LoyalFans 2 years ago

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PornBox 2 years ago

Cruel Collar Party

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LoyalFans 2 years ago

Perfect Pink Wishes

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LoyalFans 8 months ago

Sadistic Sissy Training & Hardcore Ass Worship

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Dirty Little Secret

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LoyalFans 1 year ago

You Asked For It Peaches

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LoyalFans 2 years ago

My Adventures in Latex

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LoyalFans 11 months ago

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LoyalFans 3 years ago

Femboi Debut

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LoyalFans 2 years ago

Mommy's Pretty Girl: Caged ClittyGasm 4K

49% 4K 0:10 / 22:58

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LoyalFans 3 years ago

FEMINIZED AND PEGGED BY YOUR STEP BRAT POV CUSTOM

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LoyalFans 1 week ago

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KAMS 5 months ago

Mistress Jewell's Bound Hooker pt 1

69% HD 0:10 / 12:50

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LoyalFans 2 years ago

Louboutins, Standing CBT & Heavy Weights

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LoyalFans 8 months ago

Bullied Beta

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LoyalFans 1 year ago

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PornBox 2 years ago

Girl Transformation Complete: Sissy Breeding with Dommy Rose

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LoyalFans 2 months ago

We Like You Better as a Girl

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APClips 11 months ago

Whoops Its Gone

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LoyalFans 1 year ago

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PornBox 2 years ago

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PornBox 2 years ago

Sissy Body Switch

55% HD 0:10 / 14:55

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LoyalFans 3 years ago

How Deep Is Your Love? 2/2

48% 0:10 / 11:04

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APClips 11 months ago

Horny Little Slut

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LoyalFans 1 year ago

Feminization Encouragement

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LoyalFans 1 year ago

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PornBox 2 years ago

Losing All Masculinity

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LoyalFans 1 year ago

Learn to obey your mistress! Part 3

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APClips 11 months ago

Sissy Panty Humiliation

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LoyalFans 7 months ago

Sissy Anal Training with my fuck machine!

55% HD 0:10 / 6:41

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LoyalFans 1 month ago

Queen Melanin Power Pegging Returns Full Clip

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Clips4sale 1 year ago

Double Locked Sissy - Star Nine

44% 0:10 / 21:59

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APClips 11 months ago

Sissy's First Dressing Up Session

64% 0:10 / 8:11

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APClips 11 months ago

Sissy Slut Session

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APClips 11 months ago

Sissy Maid Humiliation - Transformed into Pussy Free Sissy!

62% HD 0:10 / 12:03

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LoyalFans 2 years ago

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LoyalFans 2 years ago

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FapHouse 1 year ago

Ive Always Wanted To Do This

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LoyalFans 1 year ago

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67% HD 0:30 / 29:36

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PornBox 2 years ago

Lost Another Bet?

Lost Another Bet?

LoyalFans 1 year ago

Guided Crossdressing Feminization : Pretty In Pink | Supportive Dress Up Instructions, Makeup, Panties & Lingerie Transformation

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Clips4sale 1 week ago

Sissy Maid Party

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APClips 11 months ago

Psychobilly Bitch From Hell

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APClips 11 months ago

Over the Knee Spanks and Milking

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LoyalFans 2 months ago

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PornBox 2 years ago

SISSY PRISON Part 1 *MOV*

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Clips4sale 2 months ago

A sissy adventure with MistressVictoria (SISSY TRAINING) (CROSSDRESSING) (BISEXUAL ENCOURAGMENT)

64% HD 0:10 / 16:32

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LoyalFans 3 months ago

Making A Sissy

HD 0:10 / 17:47

LoyalFans 1 year ago

Intro To Sissification

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Clips4sale 2 years ago

Pink Bow Car Washer

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LoyalFans 2 years ago

Empress CatastroV and Mistress Baton - Sissy make-over and bare-handed spanking

HD 0:10 / 16:24

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LoyalFans 4 months ago

Your Most Humiliating Orgasm Yet (FULL HD)

56% HD 1:00 / 37:33

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Clips4sale 2 years ago

New Year Of Sissy Training - Sissy Tasks, Sissy Affirmations, Crossdressing Encouragement

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Clips4sale 2 weeks ago

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PornBox 2 years ago

Witch gender transformation sissification (1080p wmv)

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Clips4sale 2 years ago

Sissy Boyfriend Found Out and Pegged - 4k

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Clips4sale 2 years ago

Witch gender transformation sissification (1080p mp4)

42% HD 0:11 / 22:37

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Clips4sale 2 years ago

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BigButtHoles 5 months ago

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Clips4sale 1 month ago

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PornBox 2 years ago

The Fuck-Mare Training

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APClips 11 months ago

Soak Your Panties

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Clips4sale 11 months ago

Plapping' machine makes my Sissy squirt in her cage

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LoyalFans 5 months ago

MOMMY RUINS HER STEPSON'S ANAL. BIG ANAL PLUG IN YOUR HOLE. ANAL STRETCH MONSTER DILDO.

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Sheer 2 years ago

SISSY PRISON Part 3 *wmv*

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Clips4sale 1 month ago

Slut Candy on the Inversion Cross / Slut Candy am Drehkreuz

56% HD 0:10 / 13:26

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LoyalFans 3 years ago

Double Domme Strapon Spitroast

62% HD 0:10 / 15:08

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LoyalFans 1 month ago

SISSY LOCKTOBER TASK #4 -

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Clips4sale 1 year ago

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xHamster 3 years ago

Maid To Orgasm

LoyalFans 1 year ago

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APClips 11 months ago

Goddess Samariel feeds Her cuckold sissy hubby with Her boyfriend’s cum

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Clips4sale 2 years ago

SISSYBRIT COLLECTION

36% 0:10 / 1:48:32

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APClips 11 months ago

Matriarch Ezada Sinn and Lady Valeska transform their stepdaughter into a sissy sex slave

67% HD 0:32 / 11:14

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Clips4sale 2 years ago

Dress Like Mømmy - Encouraged Bi + Sissification | Closed Captions

50% HD 0:10 / 11:29

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LoyalFans 2 years ago

Double Locked Sissy - Star Nine

40% 0:13 / 21:59

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Clips4sale 2 years ago

April's Sissy Program: 6 - Fucked

April's Sissy Program: 6 - Fucked

The Dirty Threesome with the Rubber Nurse

56% 0:10 / 7:22

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APClips 11 months ago

Popping my sissy's cherry 🍒

66% HD 0:10 / 33:27

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LoyalFans 6 months ago

SISSY PRISON Part 3 *MOV*

4K 0:32 / 14:06

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Clips4sale 2 months ago

Turning You Into My Girlfriend - A Naughty Kaylee Audio

66% 0:27 / 21:22

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C4S 9 months ago

Mistress Marleys Spanking Slut Part 1

Mistress Marleys Spanking Slut Part 1

Clips4sale 4 months ago

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Clips4sale 2 years ago

Foot Smelling Handjob

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APClips 11 months ago

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