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Sissy boy tries to control the huge dildo
48 days ago
8:28

xHamster

Sissy boy tries to control the huge dildo

Tags: amateur, anal, anal toying, big ass, boy, crossdressing, feminization

Boy to Sissy Twice Transformation
1 year ago
7:22

xHamster

Boy to Sissy Twice Transformation

Tags: amateur, big cock, boy, crossdressing, feminization, hd, ladyboy

Sissy bride style.
3 years ago
1:28

ShemaleSin

Sissy bride style.

Tags: amateur, bride, feminization, fetish, milf, sissy

Upskirt white pants
1 year ago
5:37

ShemaleSin

Upskirt white pants

Tags: amateur, anal, ass, big ass, fat, femdom, feminization

feminization sissy are u actually str8? expand your mind
3 years ago
3:10

ShemaleSin

feminization sissy are u actually str8? expand your mind

Tags: big cock, big tits, feminization, italian, ladyboy, masturbation, pov

I Love the Taste of My Own Butt Fluid, Especally While Locked in Innocence!
1 year ago
6:24

KeekAss

I Love the Taste of My Own Butt Fluid, Especally While Locked in Innocence!

Tags: amateur, anal, ass, blonde, crossdressing, deep throat, feminization

Pure Elegance Personified: Celebrating the Timeless Beauty and Grace of White Bodies in All Their Splendor
8 months ago
5:25

xHamster

Pure Elegance Personified: Celebrating the Timeless Beauty and Grace of White Bodies in All Their Splendor

Tags: amateur, american, beauty, big cock, big tits, celebrity, crossdressing

Guts ejaculation Forearms free-for-all jizm Trans doll
1 year ago
23:14

KeekAss

Guts ejaculation Forearms free-for-all jizm Trans doll

Tags: amateur, anal, anal toying, blonde, cum, cumshot, dildo

Sissy in micro bikini drinking a beer via anal outdoors then goes for a walk to expose herself
3 months ago
10:06

xHamster

Sissy in micro bikini drinking a beer via anal outdoors then goes for a walk to expose herself

Tags: amateur, anal, bikini, crossdressing, feminization, hd, ladyboy

Captivating Cuteness: Dance Like Nobody's Watching!
8 months ago
5:40

xHamster

Captivating Cuteness: Dance Like Nobody's Watching!

Tags: amateur, american, beauty, big cock, crossdressing, dancing, feminization

Transgender cow enjoying being penetrated and moaning in heat
11 months ago
20:58

xHamster

Transgender cow enjoying being penetrated and moaning in heat

Tags: amateur, anal, crossdressing, feminization, fetish, hd, high heels

Trans Gal Bouncing To Sissy Bimbo Captions
13 days ago
1:54

ShemaleSin

Trans Gal Bouncing To Sissy Bimbo Captions

Tags: big ass, bimbo, feminization, pornstar, sissy, toys, transsexual

Sissy Alice Shimada edges for you
1 year ago
16:58

xHamster

Sissy Alice Shimada edges for you

Tags: amateur, american, cosplay, crossdressing, cum, feminization, fetish

Fucking my sweet ass
2 months ago
7:16

xHamster

Fucking my sweet ass

Tags: amateur, anal, ass, beauty, big black cock, big cock, crossdressing

Feminized then Fucked by Mistress Pixie
9 months ago
5:22

xHamster

Feminized then Fucked by Mistress Pixie

Tags: amateur, american, anal, bdsm, beauty, crossdressing, cum

putting a brush in my ass
1 year ago
5:13

xHamster

putting a brush in my ass

Tags: amateur, anal, ass, barebacking, chilean, compilation, creampie

old episode : 1st toy for my sissy gap
3 years ago
4:17

ShemaleSin

old episode : 1st toy for my sissy gap

Tags: anal, assfucking, feminization, fetish, kinky, milf, old

Tubby sissy goes for a walk
2 years ago
6:32

ShemaleSin

Tubby sissy goes for a walk

Tags: feminization, fetish, humiliation, kinky, public, sissy, thong

street whore pees outside
10 months ago
2:19

xHamster

street whore pees outside

Tags: big tits, crossdressing, european, feminization, hd, high heels, ladyboy

Punk Headmistress pegs golden-haired Sissy whore for sissy training
1 year ago
5:14

ShemaleSin

Punk Headmistress pegs golden-haired Sissy whore for sissy training

Tags: amateur, anal, babe, blonde, dominatrix, feminization, fetish

banging my sissy booty large gape and cum
5 months ago
5:38

ShemaleSin

banging my sissy booty large gape and cum

Tags: anal, ass, ass to mouth, assfingering, banging, big ass, booty

Classy sissy bitch exposed in chastity, plug and sexy lingerie...
1 year ago
5:39

xHamster

Classy sissy bitch exposed in chastity, plug and sexy lingerie...

Tags: amateur, anal, bitch, clit, crossdressing, feminization, hd

Mistress Holly in thigh high black boots, JOI CEI full video eat your own cum slut, cum eating instructions jerk off instruction
4 months ago
14:09

xHamster

Mistress Holly in thigh high black boots, JOI CEI full video eat your own cum slut, cum eating instructions jerk off instruction

Tags: amateur, australian, big cock, big tits, black, blonde, boots

Chubby and soft sissy masturbating
11 months ago
0:54

xHamster

Chubby and soft sissy masturbating

Tags: amateur, bbw, chubby, curvy, european, fat, feminization

Headmistress Pixie Bangs Crossdresser Bailey Wilde
2 years ago
2:48

ShemaleSin

Headmistress Pixie Bangs Crossdresser Bailey Wilde

Tags: amateur, anal, ass, assfucking, bdsm, crossdressing, dominatrix

TS W I L L O W - Jerking Sissy Wang To BNWO PMV
1 year ago
8:04

ShemaleSin

TS W I L L O W - Jerking Sissy Wang To BNWO PMV

Tags: amateur, anal, big black cock, cum, cumshot, feminization, interracial

Sissy Fashion: Rocking Your Feminine Style
9 months ago
5:40

xHamster

Sissy Fashion: Rocking Your Feminine Style

Tags: amateur, american, beauty, big ass, big cock, big tits, crossdressing

Only way Sissy Sluts get Pussy - Vagina Toy Masturbator BDSM
5 days ago
15:04

xHamster

Only way Sissy Sluts get Pussy - Vagina Toy Masturbator BDSM

Tags: amateur, bdsm, big cock, crossdressing, cum, feminization, hd

sissy feminization instructions
3 years ago
7:22

ShemaleSin

sissy feminization instructions

Tags: amateur, anal, bdsm, domination, feminization, ladyboy, lingerie

The Chainsaw Man Sissygasm
2 months ago
6:15

xHamster

The Chainsaw Man Sissygasm

Tags: amateur, anal, cosplay, crossdressing, cum, feminization, hd

Sissy drinks her piss
5 months ago
1:25

xHamster

Sissy drinks her piss

Tags: bitch, clothed sex, dick, domination, european, fat, feminization

Asia sexy transgender swimsuit
6 months ago
5:08

xHamster

Asia sexy transgender swimsuit

Tags: amateur, asian, beauty, big cock, crossdressing, cum, feminization

Mastix Murmur Trains me to Screw her Sissy Doxies - Sasha_de_Sade & MistressMurmur on OF
3 years ago
1:00

ShemaleSin

Mastix Murmur Trains me to Screw her Sissy Doxies - Sasha_de_Sade & MistressMurmur on OF

Tags: big cock, british, dominatrix, femdom, feminization, fetish, masturbation

Sexy Blonde Sissy Dominates Redhead Trans Woman
11 months ago
3:13

xHamster

Sexy Blonde Sissy Dominates Redhead Trans Woman

Tags: amateur, american, big ass, big cock, blonde, crossdressing, feminization

Sissy man performing maid service
4 years ago
11:59

ShemaleSin

Sissy man performing maid service

Tags: anal, feminization, fetish, maid, sissy, strap-on

Transformation from a normal chap into a lascivious sissy sex doxy that can be used hard out of lenience.
1 year ago
14:34

ShemaleSin

Transformation from a normal chap into a lascivious sissy sex doxy that can be used hard out of lenience.

Tags: anal, blowjob, bondage, feminization, fetish, pov, sissy

Sissy Feminization
3 years ago
14:04

TrannyOne

Sissy Feminization

Tags: amateur, american, anal, anus, ass, barebacking, bdsm

Feminization take u as a dude and turn u into a bitch
1 year ago
1:00

KeekAss

Feminization take u as a dude and turn u into a bitch

Tags: amateur, big cock, big tits, bitch, brunette, dirty talk, domination

Teaser sissy sex toy fiddle practice
2 years ago
0:38

ShemaleSin

Teaser sissy sex toy fiddle practice

Tags: amateur, anal, dildo, feminization, fetish, masturbation, sissy

Cum in my ass Ashley is really a whore
1 year ago
5:11

xHamster

Cum in my ass Ashley is really a whore

Tags: amateur, anal, ass, bdsm, big black cock, bitch, crossdressing

Feminization Sissyfication Sissy training - Dick Worship - Female energy
4 months ago
24:43

ShemaleSin

Feminization Sissyfication Sissy training - Dick Worship - Female energy

Tags: big cock, dick, feminization, fetish, hd, sissy, worship

Sissy Maid Worships Boss Feet and Pegged
5 months ago
6:08

xHamster

Sissy Maid Worships Boss Feet and Pegged

Tags: amateur, american, anal, bdsm, beauty, boss, crossdressing

I Love Feminization
11 months ago
9:03

ShemaleZ

I Love Feminization

Tags: amateur, big ass, feminization, hd, ladyboy, stockings, teen (18+)

Sissy Hope teasing in pantihose
2 months ago
20:12

xHamster

Sissy Hope teasing in pantihose

Tags: abuse, amateur, anal, anal toying, big ass, crossdressing, dirty

Sissy Sperma trinken
5 months ago
2:40

xHamster

Sissy Sperma trinken

Tags: bdsm, compilation, creampie, cum, cum in mouth, cum swallowing, facial

Shemale slut enjoys putting huge cucumbers in her ass
4 months ago
3:00

xHamster

Shemale slut enjoys putting huge cucumbers in her ass

Tags: amateur, anal, ass, crossdressing, cucumber, feminization, hd

Sissy Bimbo Doxy - Result of Feminization Training
1 year ago
3:24

ShemaleSin

Sissy Bimbo Doxy - Result of Feminization Training

Tags: anal, asian, assfucking, babe, bimbo, blonde, feminization

Femboy Glam: Embracing My Feminine Side in Fishnets & a Mini Skirt
27 days ago
7:16

xHamster

Femboy Glam: Embracing My Feminine Side in Fishnets & a Mini Skirt

Tags: amateur, beauty, big cock, crossdressing, femdom, feminization, first time

Femdom Mistress fucks Sissy slut ass, Chastity Punishment 🔐 @Sasha_de_Sade & Saskia_de_Sade
4 months ago
0:39

aShemaleTube

Femdom Mistress fucks Sissy slut ass, Chastity Punishment 🔐 @Sasha_de_Sade & Saskia_de_Sade

Tags: ass, femdom, feminization, hd, homevideo, mistress, model

I am a Boy Crossdresser Self Spanking Cute Lady Boy Model Cosplayer
4 months ago
7:00

xHamster

I am a Boy Crossdresser Self Spanking Cute Lady Boy Model Cosplayer

Tags: amateur, american, beauty, big tits, boy, crossdressing, cute

Sultry Seduction Secrets Revealed: Unleash the Allure and Confidence of Your Inner Sexy Diva, as You Embrace Your Unique Charms
11 months ago
5:24

xHamster

Sultry Seduction Secrets Revealed: Unleash the Allure and Confidence of Your Inner Sexy Diva, as You Embrace Your Unique Charms

Tags: alluring, amateur, american, beauty, big ass, blonde, crossdressing

May third 2021
3 years ago
15:47

ShemaleSin

May third 2021

Tags: amateur, anal, babe, big tits, cage, european, femdom

These shemales will show you the way of sissy training
6 years ago
13:40

TrannyOne

These shemales will show you the way of sissy training

Tags: bimbo, dick, feminization, masturbation, music, shemale, sissy

Sissification and Strapon Fucked by Boss to Get Maid Job
4 months ago
1:36

xHamster

Sissification and Strapon Fucked by Boss to Get Maid Job

Tags: amateur, american, anal, beauty, boss, crossdressing, cum

Guy Feminized and Fucked for First Time
1 year ago
3:17

xHamster

Guy Feminized and Fucked for First Time

Tags: amateur, american, anal, bdsm, crossdressing, domination, feminization

Bisex Crossdressing And Femdom Dream Movie Scenes
3 years ago
7:43

ShemaleSin

Bisex Crossdressing And Femdom Dream Movie Scenes

Tags: amateur, bisexual, compilation, crossdressing, fantasy, femdom, feminization

Thic Crossdresser Drilled from Behind
2 years ago
1:18

ShemaleSin

Thic Crossdresser Drilled from Behind

Tags: amateur, anal, ass, assfucking, brunette, crossdressing, drilling

Whiteboi feminisation anal pussy training with massive BBC dildo
2 months ago
3:55

aShemaleTube

Whiteboi feminisation anal pussy training with massive BBC dildo

Tags: anal, babe, big black cock, blonde, dildo, feminization, fetish

Best Sissy Hypno Ever! POV CEI
2 years ago
5:36

TrannyOne

Best Sissy Hypno Ever! POV CEI

Tags: anal, anus, ass, assfucking, bdsm, blowjob, bukkake

Travesti perrita
9 months ago
6:00

xHamster

Travesti perrita

Tags: amateur, anal, big black cock, blowjob, crossdressing, feminization, hd

Femboy sissy teen teases and plays until cummimg
2 years ago
6:07

ShemaleSin

Femboy sissy teen teases and plays until cummimg

Tags: amateur, big cock, boy, cum, feminization, humiliation, masturbation

Femboy Fabulousness Unleashed: Redefine Gender Norms with Style, Confidence, and Unapologetic Fabulosity, as You Embrace Your Au
11 months ago
5:25

xHamster

Femboy Fabulousness Unleashed: Redefine Gender Norms with Style, Confidence, and Unapologetic Fabulosity, as You Embrace Your Au

Tags: amateur, american, beauty, big ass, blonde, crossdressing, femdom

Sissy Crossdresser Public Hallway Sissygasm
1 year ago
5:14

xHamster

Sissy Crossdresser Public Hallway Sissygasm

Tags: amateur, american, anal, bathroom, big cock, crossdressing, cum

I can't make no doubt of his BBC Fit inside me ???? am I a Nice Hotty? @Sasha_de_Sade
3 years ago
0:37

ShemaleSin

I can't make no doubt of his BBC Fit inside me ???? am I a Nice Hotty? @Sasha_de_Sade

Tags: anal, big black cock, blowjob, british, facial, feminization, fetish

Sissy Maker 6
3 years ago
6:10

ShemaleSin

Sissy Maker 6

Tags: feminization, shemale, sissy, transsexual

Feminization Positivity Trainer
3 years ago
3:21

TrannyOne

Feminization Positivity Trainer

Tags: american, anal, anus, ass, barebacking, bdsm, blowjob

WICKED APP DRIVER WAS EATEN IN HIS HAIR AND LEFT THE ABODE SLAPPED WITH CUM ON HIS FACE!
6 months ago
7:49

ShemaleSin

WICKED APP DRIVER WAS EATEN IN HIS HAIR AND LEFT THE ABODE SLAPPED WITH CUM ON HIS FACE!

Tags: amateur, ass, babe, bbw, belly, blowjob, chubby

Compilation with Weekly Episodes from the pain whore Alina
4 months ago
2:05

xHamster

Compilation with Weekly Episodes from the pain whore Alina

Tags: amateur, anal, bdsm, beauty, big ass, compilation, croatian

Sissy College Girl Gets Ruined and Creampied by BIG BLACK COCK
1 year ago
2:31

KeekAss

Sissy College Girl Gets Ruined and Creampied by BIG BLACK COCK

Tags: anal, big black cock, blowjob, brunette, college, creampie, crossdressing

POV Hot Golden-Haired Crossdresser Sucking Shlong
2 years ago
1:25

ShemaleSin

POV Hot Golden-Haired Crossdresser Sucking Shlong

Tags: amateur, blonde, blowjob, crossdressing, dress, femdom, feminization

Can I Get Some Dick Baby ?
1 year ago
6:28

xHamster

Can I Get Some Dick Baby ?

Tags: amateur, anal, babe, bathroom, big ass, big cock, crossdressing

RubyMabel (Stella Foxxx) uses 16in. lengthy 3in. wide vibrator on her booty
1 year ago
3:22

ShemaleSin

RubyMabel (Stella Foxxx) uses 16in. lengthy 3in. wide vibrator on her booty

Tags: amateur, anal, ass, big cock, bitch, booty, dildo

Beautiful and Bold: Crossdresser Style Secrets
8 months ago
5:45

xHamster

Beautiful and Bold: Crossdresser Style Secrets

Tags: 3some, amateur, american, beauty, big ass, big cock, crossdressing

feminization white boi
4 months ago
1:29

aShemaleTube

feminization white boi

Tags: crossdressing, feminization, hd, homevideo, interracial, pantyhose, shemale

Roommate Feminized and Screwed for Discipline (Full Episode)
1 year ago
1:04:08

ShemaleSin

Roommate Feminized and Screwed for Discipline (Full Episode)

Tags: anal, bdsm, bondage, dominatrix, feminization, fetish, hardcore

Sandra's Silicone self (trans, Crossdress, Feminization, Transformation, Nylons, Fetish)
3 years ago
16:19

ShemaleSin

Sandra's Silicone self (trans, Crossdress, Feminization, Transformation, Nylons, Fetish)

Tags: amateur, brunette, crossdressing, fake tits, feminization, fetish, high heels

Humungous cum-shot with my LARGE FUCKPOLE on my orbs
1 year ago
6:36

KeekAss

Humungous cum-shot with my LARGE FUCKPOLE on my orbs

Tags: amateur, ass, big ass, big tits, blonde, crossdressing, cum

Trans Bailey Wilde Fucked by Fuck Machine
2 months ago
4:32

xHamster

Trans Bailey Wilde Fucked by Fuck Machine

Tags: amateur, american, anal, beauty, big ass, crossdressing, cum

Femdom Headmistress real amateur hotwife cuck pair Rave Magic sissy feminization anal ding-dong pegging
7 months ago
37:20

ShemaleSin

Femdom Headmistress real amateur hotwife cuck pair Rave Magic sissy feminization anal ding-dong pegging

Tags: amateur, anal, blonde, blowjob, couple, cuckold, femdom

Unexpected a good trans friend sucked my cock to explosion
3 months ago
1:17

xHamster

Unexpected a good trans friend sucked my cock to explosion

Tags: amateur, beauty, blowjob, compilation, crossdressing, cum, cum in mouth

Slytherin Slut Casts Somes Spells, Fucks Her Tight Little Asshole, & Cums!
1 year ago
7:41

xHamster

Slytherin Slut Casts Somes Spells, Fucks Her Tight Little Asshole, & Cums!

Tags: amateur, american, anal, ass, blonde, crossdressing, cum

Sissy Fucks Dildo In chastity
1 year ago
12:28

xHamster

Sissy Fucks Dildo In chastity

Tags: american, anal, anal toying, bdsm, bra, crossdressing, dildo

Egyptian Royalty: Ankhesenamun, the Alluring Princess
6 months ago
5:35

xHamster

Egyptian Royalty: Ankhesenamun, the Alluring Princess

Tags: alluring, amateur, american, beauty, big cock, big tits, crossdressing

Jul 10th 2023
1 year ago
5:16

ShemaleSin

Jul 10th 2023

Tags: amateur, anal, assfucking, bdsm, bondage, close up, domination

Sissy Elvi Lynx - Asshole Destruction with Sex Machine Hot Sissy Bubble Butt
1 year ago
4:35

xHamster

Sissy Elvi Lynx - Asshole Destruction with Sex Machine Hot Sissy Bubble Butt

Tags: amateur, anal, anal toying, ass, blonde, european, feminization

Walking in the grocery store
1 year ago
2:41

xHamster

Walking in the grocery store

Tags: amateur, american, bdsm, couple, crossdressing, domination, feminization

You are now my pretty little crossdresser sissy doll
1 year ago
3:35

TrannyOne

You are now my pretty little crossdresser sissy doll

Tags: bdsm, bisexual, crossdressing, doll, domination, fantasy, femdom

I ruined my orgasm like a sissy
6 months ago
4:56

xHamster

I ruined my orgasm like a sissy

Tags: amateur, anal, anal toying, ass, big black cock, big cock, black

Smoking femboy strokes and shows off
36 days ago
1:07

xHamster

Smoking femboy strokes and shows off

Tags: amateur, american, big cock, crossdressing, cum, feminization, hd

HOT UNDERCLOTHING STOCKING AND HIGH HEELS FEMINIZATION SISSY TRANSFORMATION Locked in Chastity
3 years ago
9:22

ShemaleSin

HOT UNDERCLOTHING STOCKING AND HIGH HEELS FEMINIZATION SISSY TRANSFORMATION Locked in Chastity

Tags: amateur, crossdressing, feminization, fetish, high heels, ladyboy, sissy

Sophie your french maid does the cleaning with a plug in her ass
10 months ago
6:42

xHamster

Sophie your french maid does the cleaning with a plug in her ass

Tags: anal, ass, crossdressing, feminization, fetish, french, hd

INSTRUCTING for SISSY: "four STEPS to ACHIEVING SISSYGASM" Veronica Taboo trains SISSIFICATION
1 year ago
15:14

KeekAss

INSTRUCTING for SISSY: "four STEPS to ACHIEVING SISSYGASM" Veronica Taboo trains SISSIFICATION

Tags: amateur, anal, anal toying, boy, brunette, cage, crossdressing

Joselynne Cd Heels And Stockings With Anal Fox Tail First
40 days ago
32:59

xHamster

Joselynne Cd Heels And Stockings With Anal Fox Tail First

Tags: amateur, anal, ass, big ass, crossdressing, feminization, hd

Suntan Well-Lubed Up Elastic Arse Hoe Drills Her Butt
1 year ago
9:38

KeekAss

Suntan Well-Lubed Up Elastic Arse Hoe Drills Her Butt

Tags: amateur, anal, ass, babe, big ass, blowjob, deep throat

Sissy Hope, the slut being controlled by Master on videocall
1 year ago
17:43

xHamster

Sissy Hope, the slut being controlled by Master on videocall

Tags: amateur, beauty, big ass, crossdressing, dildo, feminization, hd

Hairless, anal-plugged sissy, cums in new panties, tights & heels
21 days ago
6:28

xHamster

Hairless, anal-plugged sissy, cums in new panties, tights & heels

Tags: amateur, anal, anal toying, crossdressing, cum, cumshot, feminization

Exhibiting in Female Underwear and Cumshot in Front of the Camera, Big Amateur Cock
1 year ago
1:58

xHamster

Exhibiting in Female Underwear and Cumshot in Front of the Camera, Big Amateur Cock

Tags: amateur, big cock, crossdressing, cumshot, exhibitionist, feminization, handjob

Sissy Femboy Crossdresser play with Large Penis - Large jock
2 years ago
0:33

ShemaleSin

Sissy Femboy Crossdresser play with Large Penis - Large jock

Tags: big cock, crossdressing, dick, feminization, huge cock, pov, sissy

Sissy Butt Girl Fucks Ass On 4xl Monster Dildo
1 year ago
1:17

xHamster

Sissy Butt Girl Fucks Ass On 4xl Monster Dildo

Tags: amateur, american, anal, anal toying, ass, crossdressing, dildo

Sissy Plays with her Butt on a Sex-Toy
3 years ago
2:23

ShemaleSin

Sissy Plays with her Butt on a Sex-Toy

Tags: anal, ass, babe, big ass, feet, feminization, fetish

feet fetish
1 year ago
6:23

xHamster

feet fetish

Tags: amateur, crossdressing, european, feet, feminization, fetish, hd

Sissy Crossdress Shlong Worship ft Trans Femdom
1 year ago
0:59

ShemaleSin

Sissy Crossdress Shlong Worship ft Trans Femdom

Tags: babe, big cock, blonde, crossdressing, femdom, feminization, fetish

Mistress Cassidy Slaps Sissy's Ass Till Its Red
1 year ago
2:16

xHamster

Mistress Cassidy Slaps Sissy's Ass Till Its Red

Tags: amateur, american, anal, ass, bdsm, crossdressing, cum

Caged tiny clitty sissy shemale pissing outdoor and walking while pissing
51 days ago
7:05

xHamster

Caged tiny clitty sissy shemale pissing outdoor and walking while pissing

Tags: amateur, crossdressing, cum, feminization, hd, indian, ladyboy

Sissy Crimson Pokes (HDR Movie)
1 year ago
2:03

KeekAss

Sissy Crimson Pokes (HDR Movie)

Tags: amateur, bodystocking, crossdressing, feminization, fetish, hd, high heels

Sissy screwed in the booty
1 year ago
3:48

ShemaleSin

Sissy screwed in the booty

Tags: amateur, anal, assfucking, big black cock, booty, dildo, femdom

Cute CD Femboy Has Hands-Free Sissygasm & Smack it After Riding Big sex tool
3 years ago
4:01

ShemaleSin

Cute CD Femboy Has Hands-Free Sissygasm & Smack it After Riding Big sex tool

Tags: amateur, anal, babe, bdsm, blonde, cum, cute

Sissy in beautiful pantyhose on pmv
1 year ago
4:03

KeekAss

Sissy in beautiful pantyhose on pmv

Tags: amateur, asian, babe, beauty, big ass, bimbo, brunette

Katykoroleva gets fucked in the ass
10 months ago
1:14

xHamster

Katykoroleva gets fucked in the ass

Tags: amateur, ass, beauty, big cock, blonde, blowjob, crossdressing

BBC shower snake charmer
4 months ago
7:35

xHamster

BBC shower snake charmer

Tags: amateur, american, bathroom, big black cock, blonde, blowjob, crossdressing

Sucking a dick and getting milk in my throat!
3 months ago
8:24

ShemaleSin

Sucking a dick and getting milk in my throat!

Tags: amateur, ass, ass to mouth, asslick, babe, bbw, belly

Cumdump me I need new Dick onlyfans alexiakessel1
3 months ago
1:20

xHamster

Cumdump me I need new Dick onlyfans alexiakessel1

Tags: amateur, american, anal, barebacking, beauty, big cock, creampie

MASTER SERGEANT Locks Faggyboi in Chastity
10 months ago
3:08

xHamster

MASTER SERGEANT Locks Faggyboi in Chastity

Tags: anal, beauty, big black cock, black, blowjob, crossdressing, feminization

Jessic Ajain 2nd video
11 months ago
1:18

xHamster

Jessic Ajain 2nd video

Tags: amateur, beauty, crossdressing, feminization, hd, homevideo, shemale

Mistress Cassidy Fucks Sissy Doggystyle and Paddle
1 year ago
5:35

xHamster

Mistress Cassidy Fucks Sissy Doggystyle and Paddle

Tags: amateur, american, anal, bdsm, bondage, crossdressing, doggystyle

My Feminization Nearly Complete FULL
1 year ago
12:04

ShemaleSin

My Feminization Nearly Complete FULL

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Feminization - Sissy training - Sissy joi - Be compliant Faggot
4 months ago
24:53

ShemaleSin

Feminization - Sissy training - Sissy joi - Be compliant Faggot

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Raver Sissy femboy in chastity bangs BBC 4 Femdom Domme whilst that babe eats dinner, coarse anal wench 4/5
1 year ago
25:11

ShemaleSin

Raver Sissy femboy in chastity bangs BBC 4 Femdom Domme whilst that babe eats dinner, coarse anal wench 4/5

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Sissy blows and eating
5 months ago
1:40

xHamster

Sissy blows and eating

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Kym's PVC Bodysuit (trans, Hose, Crossdress, Legs, Heels, Transformation, Female Mask, Mask)
3 years ago
2:31

ShemaleSin

Kym's PVC Bodysuit (trans, Hose, Crossdress, Legs, Heels, Transformation, Female Mask, Mask)

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SISSY SCREWED. CROSSDRESSER. TRAP. FEMINIZATION
2 years ago
2:17

ShemaleSin

SISSY SCREWED. CROSSDRESSER. TRAP. FEMINIZATION

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Sissy cums in cage to hurting & banding it’s white ball white extinction BNWO gal scarlett ebony
2 years ago
13:10

ShemaleSin

Sissy cums in cage to hurting & banding it’s white ball white extinction BNWO gal scarlett ebony

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cute shemale femboy cums on her sailor uniform
1 year ago
11:50

xHamster

cute shemale femboy cums on her sailor uniform

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Living Your Truth: Embracing the Crossdresser Lifestyle!
8 months ago
5:33

xHamster

Living Your Truth: Embracing the Crossdresser Lifestyle!

Tags: amateur, american, beauty, big cock, big tits, crossdressing, femdom

Sissy chupa polla
29 days ago
5:34

xHamster

Sissy chupa polla

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Bailey Wilde Feminized Into Cheerleader and Screwed by Mistresse Pixie
1 year ago
0:53

ShemaleSin

Bailey Wilde Feminized Into Cheerleader and Screwed by Mistresse Pixie

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Sissy Floozy Merits Humiliation and Public Exposure
1 year ago
0:30

ShemaleSin

Sissy Floozy Merits Humiliation and Public Exposure

Tags: amateur, anal, domination, feminization, fetish, humiliation, kinky

Mrs R Boudoir Visit (trans, Feminization, Female Mask, Mask, Crossdress, Transformation, big beautiful woman)
3 years ago
3:43

ShemaleSin

Mrs R Boudoir Visit (trans, Feminization, Female Mask, Mask, Crossdress, Transformation, big beautiful woman)

Tags: babe, bbw, beauty, brunette, crossdressing, dress, feminization

Becoming a Sissy Girl is the Best Transformation
11 months ago
5:43

xHamster

Becoming a Sissy Girl is the Best Transformation

Tags: amateur, big cock, crossdressing, cum, feminization, fetish, hd

Anal training for dad's BBC
1 year ago
9:59

ShemaleSin

Anal training for dad's BBC

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Large Ebony Weenie Feminization Coach for Constrained Sissy Lads (BBC) (Captions)
3 years ago
6:13

ShemaleSin

Large Ebony Weenie Feminization Coach for Constrained Sissy Lads (BBC) (Captions)

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I Cumming From Hard Strap on Fuck
1 year ago
1:00

xHamster

I Cumming From Hard Strap on Fuck

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Sissy destroying her ass in public toilet
4 months ago
3:42

xHamster

Sissy destroying her ass in public toilet

Tags: amateur, anal, anal toying, ass, bathroom, clit, crossdressing

I got a weight bench to Assist grow my boobs and keep in shape during the time that going throughout my feminization process. then i thought why not t
1 year ago
3:40

ShemaleSin

I got a weight bench to Assist grow my boobs and keep in shape during the time that going throughout my feminization process. then i thought why not t

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Embracing my confidence and expressing my unique style as a hot crossdresser
11 months ago
6:30

xHamster

Embracing my confidence and expressing my unique style as a hot crossdresser

Tags: amateur, american, beauty, big ass, blonde, crossdressing, cum

International Star
1 year ago
6:43

xHamster

International Star

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Sashay Your Way to Stardom: Crossdresser Kitty's Journey!
8 months ago
5:38

xHamster

Sashay Your Way to Stardom: Crossdresser Kitty's Journey!

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Femboy Elena Koslov's Tentacle Sex tool Teaser #1
47 days ago
0:24

ShemaleSin

Femboy Elena Koslov's Tentacle Sex tool Teaser #1

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Sissy TS Willow Hammerz - Showing off locked up clitty
2 years ago
1:02

ShemaleSin

Sissy TS Willow Hammerz - Showing off locked up clitty

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Sissy a little taped up in Highheels
1 year ago
3:39

xHamster

Sissy a little taped up in Highheels

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White sissy gets fucked in the ass with a big black dildo. Feminization, Punishment, Analysis
8 months ago
6:47

XXXDan

White sissy gets fucked in the ass with a big black dildo. Feminization, Punishment, Analysis

Tags: anal, ass, big ass, black, clit, dildo, feminization

Mistress Cassidy Makes Sissy Maid Get Cowgirl Fucked
1 year ago
3:28

xHamster

Mistress Cassidy Makes Sissy Maid Get Cowgirl Fucked

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For Daddy - Hopelessly Begging To Unlock Chastity Cage
4 months ago
4:10

xHamster

For Daddy - Hopelessly Begging To Unlock Chastity Cage

Tags: amateur, american, bdsm, beauty, cage, crossdressing, daddies

Big Booty Blonde Sissy rides 9 inch dildo
3 months ago
7:42

xHamster

Big Booty Blonde Sissy rides 9 inch dildo

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Hot Crossdresser Reverse Cowgirl Drilled by Domina
2 years ago
5:13

ShemaleSin

Hot Crossdresser Reverse Cowgirl Drilled by Domina

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BiG TiTS HOT LADYBOY SEXY NATURAL SHEMALE BOOBS
6 months ago
6:32

xHamster

BiG TiTS HOT LADYBOY SEXY NATURAL SHEMALE BOOBS

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guy gets feminized and ass fucked in prison by chick
4 years ago
18:06

ShemalePub

guy gets feminized and ass fucked in prison by chick

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Cute Pants Upskirt
2 years ago
13:03

ShemaleSin

Cute Pants Upskirt

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Trans Goddess Loves To Get Your Dick Hard
2 years ago
5:41

TrannyOne

Trans Goddess Loves To Get Your Dick Hard

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Sissy crossdresser cock and balls tucking taping
1 year ago
2:15

xHamster

Sissy crossdresser cock and balls tucking taping

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Chastity Sissy fuck her asspussy for Mistress task
10 months ago
9:03

xHamster

Chastity Sissy fuck her asspussy for Mistress task

Tags: anal, bdsm, crossdressing, domination, feminization, fetish, hd

Sissy tries to escape bindings
1 year ago
4:57

ShemaleSin

Sissy tries to escape bindings

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Sissy Maid Hardware Store Humiliation Adventure staring Sissy Mindy
8 months ago
4:44

xHamster

Sissy Maid Hardware Store Humiliation Adventure staring Sissy Mindy

Tags: american, blonde, cosplay, crossdressing, feminization, hd, humiliation

CROSSDRESSER COMPILATION GLAMOROUS LADYBOY SCREWED Sissy Chastity Screwed FEMDOM
3 years ago
9:06

ShemaleSin

CROSSDRESSER COMPILATION GLAMOROUS LADYBOY SCREWED Sissy Chastity Screwed FEMDOM

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Sissy slut makup boy 2 gurl
1 year ago
2:15

xHamster

Sissy slut makup boy 2 gurl

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Hot Shemale
9 months ago
5:22

xHamster

Hot Shemale

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Juggsy Female Mask Sissy Whore #2
4 months ago
10:19

xHamster

Juggsy Female Mask Sissy Whore #2

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Mr. Hankey's Thicky Nicky vs Big Bubble Butt
1 year ago
5:08

xHamster

Mr. Hankey's Thicky Nicky vs Big Bubble Butt

Tags: amateur, anal, ass, beauty, big ass, big cock, blonde

Fuchsia Doll High Heels and Ebony Hose and Pink Garter
3 years ago
1:59

ShemaleSin

Fuchsia Doll High Heels and Ebony Hose and Pink Garter

Tags: ass, dildo, doll, ebony, feminization, garter belts, high heels

My Cumshot Compilation - Mourning like a male as I shoot my cum, this is me, when I get super horny
3 months ago
14:44

xHamster

My Cumshot Compilation - Mourning like a male as I shoot my cum, this is me, when I get super horny

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Boy To Teen Sissy Girl Transformation
1 year ago
6:27

xHamster

Boy To Teen Sissy Girl Transformation

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Crossdresser Model Magic: Dancing with Grace
8 months ago
5:34

xHamster

Crossdresser Model Magic: Dancing with Grace

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COLLEGIATE PITCHER Cheats on Girfriend with Faggyboi
31 days ago
1:55

xHamster

COLLEGIATE PITCHER Cheats on Girfriend with Faggyboi

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AlsoNicole breast growth, going into Further Feminization
3 years ago
3:40

TrannyOne

AlsoNicole breast growth, going into Further Feminization

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Samantha sissy have joy with her schlong, this babe can cum and milking very well, feminization is inevitable, try to get milk from tits and weenie jo
1 year ago
2:29

ShemaleSin

Samantha sissy have joy with her schlong, this babe can cum and milking very well, feminization is inevitable, try to get milk from tits and weenie jo

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sissy
1 year ago
0:12

xHamster

sissy

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Lisa feminizes herself each day after work. Lisa wears her weenie cage around the clock for a successful feminization. This Babe pulls down her diaper
8 months ago
1:36

ShemaleSin

Lisa feminizes herself each day after work. Lisa wears her weenie cage around the clock for a successful feminization. This Babe pulls down her diaper

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Sissy Makoto Niijima Edges for you
1 year ago
33:41

xHamster

Sissy Makoto Niijima Edges for you

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Ebony Mini Suit Juggsy
3 years ago
4:58

ShemaleSin

Ebony Mini Suit Juggsy

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Reconditioning still in progress
1 year ago
1:27

ShemaleSin

Reconditioning still in progress

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Hot Cheap Doxy from Street Wanted to Suck Rod- Full Episode on my Onlyfans (link in Bio)
3 years ago
0:28

ShemaleSin

Hot Cheap Doxy from Street Wanted to Suck Rod- Full Episode on my Onlyfans (link in Bio)

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Feminization Training - Show This To Your Wife
2 months ago
7:58

xHamster

Feminization Training - Show This To Your Wife

Tags: amateur, american, bdsm, crossdressing, femdom, feminization, hd

racing sissy anal handsfree sissygasm
4 months ago
13:51

xHamster

racing sissy anal handsfree sissygasm

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Joselynne Cd In My Lovely Dress Lingerie And Heels To You
2 months ago
20:07

xHamster

Joselynne Cd In My Lovely Dress Lingerie And Heels To You

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Trans angel showing off body
3 years ago
3:42

ShemaleSin

Trans angel showing off body

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Anal Plugging with Kandi Kane
23 days ago
3:50

xHamster

Anal Plugging with Kandi Kane

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My Bussy got stuffed in Lingerie
11 months ago
18:23

xHamster

My Bussy got stuffed in Lingerie

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Brandynette Brainwash Joy Button Dressup - Why Bambi ruins your expectations!
1 year ago
14:21

KeekAss

Brandynette Brainwash Joy Button Dressup - Why Bambi ruins your expectations!

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Can U Handle Your Keyholder's Gifts? - Anal Play, Feminization, Chastity Praise RP ????
2 months ago
28:30

ShemaleSin

Can U Handle Your Keyholder's Gifts? - Anal Play, Feminization, Chastity Praise RP ????

Tags: amateur, anal, dildo, femdom, feminization, fetish, prostate

Crossdressing Sissy Bitch Femboy Anal Beginnings
2 years ago
2:11

ShemaleSin

Crossdressing Sissy Bitch Femboy Anal Beginnings

Tags: amateur, anal, bitch, crossdressing, feminization, sissy, toys