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Bussy Busted in Training
1 year ago
14:07

ShemaleSin

Bussy Busted in Training

Tags: amateur, anal, bus, dildo, feminization, fisting, gaping hole

Trashy fag show off
5 months ago
2:35

xHamster

Trashy fag show off

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Sissyboi Femboi Chastity Big Dildo Anal Doggiestyle
1 year ago
2:01

xHamster

Sissyboi Femboi Chastity Big Dildo Anal Doggiestyle

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BOY Legs Shaved Fresh Attractive Ladyboy Legs
1 year ago
6:30

xHamster

BOY Legs Shaved Fresh Attractive Ladyboy Legs

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2025 Sissy Compilation
3 months ago
1:16

xHamster

2025 Sissy Compilation

Tags: amateur, anal, big ass, big black cock, big tits, compilation, crossdressing

Sissy Trans Maid deepthroats cock while locked
4 months ago
2:33

xHamster

Sissy Trans Maid deepthroats cock while locked

Tags: amateur, american, beauty, blowjob, crossdressing, deep throat, dick

Sexy Crossdresser Doggy style Screwed by Female-dominant
2 months ago
4:24

ShemaleSin

Sexy Crossdresser Doggy style Screwed by Female-dominant

Tags: amateur, anal, ass, bdsm, crossdressing, doggystyle, domination

Crossdresser walking at night.
1 year ago
5:30

ShemaleSin

Crossdresser walking at night.

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Sissy frisky fucking BBC Dildo in Public Garage & Wasch Maschine
9 months ago
6:30

xHamster

Sissy frisky fucking BBC Dildo in Public Garage & Wasch Maschine

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Sissy Femboy Anal Masturbation Compilation - Chastity and Feminization Progress
1 year ago
11:12

xHamster

Sissy Femboy Anal Masturbation Compilation - Chastity and Feminization Progress

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Magic Melody Uses Her Ass to Summon and Fuck Magical Toys
1 year ago
8:12

xHamster

Magic Melody Uses Her Ass to Summon and Fuck Magical Toys

Tags: amateur, anal, anal toying, ass, beauty, big ass, cumshot

Brandy Monroe plays
7 months ago
3:10

xHamster

Brandy Monroe plays

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In lingerie with my dildo
4 months ago
10:23

xHamster

In lingerie with my dildo

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

Joselynne Crossdresser Oral Dildo
2 months ago
5:47

xHamster

Joselynne Crossdresser Oral Dildo

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POV housemate finds your panties and feminizes you JOI dominant trans girl
5 months ago
11:53

xHamster

POV housemate finds your panties and feminizes you JOI dominant trans girl

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Anal for My Chastity Cage Sissy Doxy! DRAGON SEX-TOY CUM DISCHARGED!!!
1 year ago
15:46

ShemaleSin

Anal for My Chastity Cage Sissy Doxy! DRAGON SEX-TOY CUM DISCHARGED!!!

Tags: anal, anal toying, big tits, brunette, cage, cum, cumshot

Sissy for bbc crossdresser has big cock addiction wants to worship cock
1 year ago
9:41

xHamster

Sissy for bbc crossdresser has big cock addiction wants to worship cock

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

Sexy Brunette Crossdresser Sucks Crossdresser's Cock
1 year ago
13:04

xHamster

Sexy Brunette Crossdresser Sucks Crossdresser's Cock

Tags: amateur, american, anal, big ass, big cock, blowjob, brunette

Dominatrix Releases Crossdresser from Chastity then Deepthroats Cock
3 months ago
1:51

xHamster

Dominatrix Releases Crossdresser from Chastity then Deepthroats Cock

Tags: amateur, american, anal, big ass, big cock, blowjob, crossdressing

A FLESHLY ESCAPE [FUTA] [HOPE FT. LITTLEDEMON]
1 year ago
25:44

ShemaleSin

A FLESHLY ESCAPE [FUTA] [HOPE FT. LITTLEDEMON]

Tags: 3d, amateur, anal, blowjob, cowgirl, creampie, cumshot

Anal Broomstick Sissy Faggot
12 days ago
5:01

ShemaleSin

Anal Broomstick Sissy Faggot

Tags: amateur, anal, ass, bbw, bdsm, big ass, big cock

Crystal Fucked by Fuck Machine
1 year ago
2:11

xHamster

Crystal Fucked by Fuck Machine

Tags: anal, ass, beauty, big ass, crossdressing, cute, dick

Femboy Oral-job Oral-sex Tease #1
10 months ago
0:24

ShemaleSin

Femboy Oral-job Oral-sex Tease #1

Tags: amateur, babe, blonde, blowjob, deep throat, dildo, feminization

xsannetjuhx sents sexting to daddy
10 months ago
2:45

xHamster

xsannetjuhx sents sexting to daddy

Tags: amateur, bathroom, blonde, crossdressing, cum, cute, daddies

sissy orgasm on a fucking machine ! your trap rides a dildo and cums in the chastity belt!
9 months ago
9:09

xHamster

sissy orgasm on a fucking machine ! your trap rides a dildo and cums in the chastity belt!

Tags: anal, blonde, cum, cumshot, cute, dildo, feminization

Mature Woman Feminization Sissyboy
2 years ago
8:00

getTranny

Mature Woman Feminization Sissyboy

Tags: bdsm, blonde, brunette, crossdressing, domination, femdom, feminization

Alt trans sissy whore locked in chastity cage bangs herself with large ebony sex toy
8 months ago
3:40

ShemaleSin

Alt trans sissy whore locked in chastity cage bangs herself with large ebony sex toy

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Melinda James CD jerking her Lady Cock
3 months ago
9:39

xHamster

Melinda James CD jerking her Lady Cock

Tags: amateur, anal, beauty, crossdressing, dick, feminization, german

Chap disguises himself as a woman and masturbates with artificial twat
7 months ago
2:33

ShemaleSin

Chap disguises himself as a woman and masturbates with artificial twat

Tags: amateur, asian, big tits, booty, cunt, feminization, fetish

Riding large dildos - 9Inch V1-0013 - Jun 08, 2025
38 days ago
5:35

ShemaleSin

Riding large dildos - 9Inch V1-0013 - Jun 08, 2025

Tags: amateur, anal, ass, big ass, booty, dildo, fat

Effeminate suck your cousin ml
2 months ago
6:16

xHamster

Effeminate suck your cousin ml

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

Team Rocket Jessie Cums a Lot Taking Monster Pink Schlong - Chloe Cox
2 months ago
7:03

ShemaleSin

Team Rocket Jessie Cums a Lot Taking Monster Pink Schlong - Chloe Cox

Tags: amateur, anal, cosplay, cum, cumshot, dildo, feminization

For my followers new content is ready
4 months ago
6:14

xHamster

For my followers new content is ready

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I caught my trans roommate with her kewl booty up
Today
0:21

ShemaleSin

I caught my trans roommate with her kewl booty up

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Big Butt Booty Sexy Dressed Hot Ladyboy Shemale Crossdresser Kitty
1 year ago
6:30

xHamster

Big Butt Booty Sexy Dressed Hot Ladyboy Shemale Crossdresser Kitty

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TS Bailey Wilde Cums from Being Fucked
29 days ago
1:03

xHamster

TS Bailey Wilde Cums from Being Fucked

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

Trixy Sissy Babe welcomes you in a hotel
4 months ago
2:22

xHamster

Trixy Sissy Babe welcomes you in a hotel

Tags: amateur, anal, babe, beauty, big cock, crossdressing, facial

Paloma Veiga showing her large rod on the street
2 months ago
10:10

ShemaleSin

Paloma Veiga showing her large rod on the street

Tags: beauty, feminization, street, tranny, transsexual

Sissy Fuckdoll Machine Bred
1 year ago
9:28

xHamster

Sissy Fuckdoll Machine Bred

Tags: amateur, anal, crossdressing, dildo, feminization, hd, lingerie

Unboxing my new Cage
8 months ago
1:49

xHamster

Unboxing my new Cage

Tags: amateur, beauty, cage, crossdressing, european, feminization, german

I Am Such an Eager Cock Sucking Sissy
5 months ago
1:09

xHamster

I Am Such an Eager Cock Sucking Sissy

Tags: amateur, american, bbw, beauty, blowjob, crossdressing, dick

Dirty sissy Dominates a Monster Dildo
8 months ago
9:38

xHamster

Dirty sissy Dominates a Monster Dildo

Tags: amateur, anal, crossdressing, cum, dildo, dirty, feminization

white ladyboy in Thailand riding a dildo and injecting hormones
2 months ago
1:06

xHamster

white ladyboy in Thailand riding a dildo and injecting hormones

Tags: amateur, american, asian, bdsm, crossdressing, dildo, feminization

Trans girl masturbating married guy's cock and making him suck her cock
7 months ago
6:32

xHamster

Trans girl masturbating married guy's cock and making him suck her cock

Tags: amateur, beauty, big cock, blowjob, crossdressing, dick, feminization

Sissy Training female energy (english voice)
3 years ago
2:37

ShemaleSin

Sissy Training female energy (english voice)

Tags: ass, babe, british, cute, english, feminization, fetish

Her Chastity Cage Flops Around While Her Asshole is Stretched Beyond Recognition!
6 months ago
6:40

xHamster

Her Chastity Cage Flops Around While Her Asshole is Stretched Beyond Recognition!

Tags: amateur, american, anal, ass, blonde, cage, feminization

T-girl locked in a cage enjoys anal play and sissy feminization
11 months ago
7:19

ShemaleMovie

T-girl locked in a cage enjoys anal play and sissy feminization

Tags: amateur, anal, cage, crossdressing, cum, dildo, feminization

Crossdresser Adventures: Exploring a World of Fashion
1 year ago
5:30

xHamster

Crossdresser Adventures: Exploring a World of Fashion

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

Pink Wetlook Sissy have fun
10 months ago
2:50

xHamster

Pink Wetlook Sissy have fun

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

Sexiest Sissy Fucked by Fuck Machine Missionary
1 year ago
9:15

xHamster

Sexiest Sissy Fucked by Fuck Machine Missionary

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

Trans Hottie Fucks Trans Beauty Raw
6 months ago
5:24

xHamster

Trans Hottie Fucks Trans Beauty Raw

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

Sexy Blonde Femboy Bailey Wilde Photoshoot
8 months ago
2:41

xHamster

Sexy Blonde Femboy Bailey Wilde Photoshoot

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

Feminization training 3
50 days ago
9:53

aShemaleTube

Feminization training 3

Tags: amateur, anal, big cock, crossdressing, feminization, lingerie, masturbation

FISTING DOUBLE SISSYGASM CUMSHOTS
1 day ago
1:38

ShemaleSin

FISTING DOUBLE SISSYGASM CUMSHOTS

Tags: anal, ass, cum, cum swapping, cumshot, dominatrix, feminization

Your Lesbo Wife Turns U Into a Woman - Clara Dee POV Virtual Sex Sissy Pegging
4 months ago
0:27

ShemaleSin

Your Lesbo Wife Turns U Into a Woman - Clara Dee POV Virtual Sex Sissy Pegging

Tags: assfingering, bbw, blonde, chubby, cute, dildo, dirty talk

HANDS-FREE CUMSHOT Cute Smooth Legs Booty Smooth Skin Model Femboy
2 months ago
5:41

xHamster

HANDS-FREE CUMSHOT Cute Smooth Legs Booty Smooth Skin Model Femboy

Tags: amateur, booty, compilation, cum, cum in mouth, cumshot, cute

AND GREATER QUANTITY 25 CUMSHOTS
1 year ago
11:46

ShemaleSin

AND GREATER QUANTITY 25 CUMSHOTS

Tags: anal, compilation, couple, cum, cumshot, dildo, dominatrix

Johnny Moon – A New Star In The Feminization Academy
3 years ago
8:00

getTranny

Johnny Moon – A New Star In The Feminization Academy

Tags: anal, big cock, blonde, crossdressing, deep throat, facial, feminization

Young and slutty trans girl compilation
3 months ago
5:07

xHamster

Young and slutty trans girl compilation

Tags: amateur, beauty, big cock, compilation, crossdressing, feminization, hd

Homemade Hottie: DIY Crossdressing Creations That'll Amaze You!
1 year ago
5:54

xHamster

Homemade Hottie: DIY Crossdressing Creations That'll Amaze You!

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

Feminization, chastity-cage
7 months ago
5:27

ShemaleTaxi

Feminization, chastity-cage

Tags: cage, feminization, homevideo, lingerie, masturbation, shemale, sissy

Goth Crossdresser Fucks Redhead Trans
7 months ago
1:11

xHamster

Goth Crossdresser Fucks Redhead Trans

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

Sissy femboy gets anal pleasure and intense feminization
1 year ago
7:54

ShemaleTaxi

Sissy femboy gets anal pleasure and intense feminization

Tags: anal, anal toying, beauty, crossdressing, feminization, orgasm, shemale

I caress myself
4 months ago
1:11

xHamster

I caress myself

Tags: amateur, crossdressing, cute, feminization, lingerie, shemale, sissy

Femboy dancing in thong + enema of her big tranny ass (part 1)
4 months ago
11:39

xHamster

Femboy dancing in thong + enema of her big tranny ass (part 1)

Tags: amateur, anal, ass, big ass, colombian, creampie, dancing

Sissy Delicious - The Program (Part Two)
3 years ago
13:40

TrannyOne

Sissy Delicious - The Program (Part Two)

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

nasty uber car driver jerked me off until I came. We came jointly!
2 months ago
2:54

ShemaleSin

nasty uber car driver jerked me off until I came. We came jointly!

Tags: anal, car, feminization, jerking, orgasm, transsexual

Super Hot Crossdresser Bailey Wilde Jerking Off
1 year ago
8:08

xHamster

Super Hot Crossdresser Bailey Wilde Jerking Off

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

Sissification Transformation by Roommate
2 months ago
7:17

xHamster

Sissification Transformation by Roommate

Tags: amateur, american, anal, bdsm, beauty, big cock, blonde

Trans Women Fucking Doggystyle Close Up
9 months ago
7:24

xHamster

Trans Women Fucking Doggystyle Close Up

Tags: amateur, american, anal, beauty, big ass, big cock, close up

Keira Enigma Trans Masturbation POV
40 days ago
3:13

ShemaleSin

Keira Enigma Trans Masturbation POV

Tags: feminization, masturbation, pov, small cock, tiny dick, tranny, transsexual

Melinda's huge buttplug riding scene
5 months ago
5:46

xHamster

Melinda's huge buttplug riding scene

Tags: amateur, anal, beauty, buttplug, crossdressing, feminization, german

Sissy Maid Fucks Her Pussy Raw With A Dildo
5 months ago
1:07

xHamster

Sissy Maid Fucks Her Pussy Raw With A Dildo

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

Beautiful trans cum in cage.
7 months ago
10:10

xHamster

Beautiful trans cum in cage.

Tags: amateur, beauty, big cock, blonde, cum, feminization, hd

Hot Lalin girl TS Foxxy In "Lascivious three Sausages Sandwich"!
11 months ago
12:27

ShemaleSin

Hot Lalin girl TS Foxxy In "Lascivious three Sausages Sandwich"!

Tags: anal, ass to mouth, asslick, big cock, creampie, dick, feminization

Releasing HUGE Trans Cock to Suck
10 months ago
1:42

xHamster

Releasing HUGE Trans Cock to Suck

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

Sexy Trans Bailey Wilde Cums from Being Fucked
5 months ago
5:50

xHamster

Sexy Trans Bailey Wilde Cums from Being Fucked

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

Sissy Doxy in Pink Chastity
4 months ago
1:01

ShemaleSin

Sissy Doxy in Pink Chastity

Tags: feminization, fetish, lingerie, sissy, slut, tgirl

Sissy Laci Performs Anal Masterbation
7 months ago
5:04

xHamster

Sissy Laci Performs Anal Masterbation

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

Skinny Trans Kayleigh Coxx Gives Her Rectal hole To Real Colby Jansen!
10 months ago
11:40

ShemaleSin

Skinny Trans Kayleigh Coxx Gives Her Rectal hole To Real Colby Jansen!

Tags: anal, ass, ass to mouth, assfingering, beauty, blowjob, brunette

Intriguing Intimacy: A Closer Look into My World
1 year ago
6:57

xHamster

Intriguing Intimacy: A Closer Look into My World

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

Kayla's Guiding Principles for Mental Domination and Feminization of Sissy Submissives
1 year ago
8:22

ShemaleTaxi

Kayla's Guiding Principles for Mental Domination and Feminization of Sissy Submissives

Tags: amateur, ass, domination, feminization, masturbation, shemale, sissy

Femboy Jade Madison Sucking Dick POV
1 year ago
3:39

xHamster

Femboy Jade Madison Sucking Dick POV

Tags: amateur, american, anal, barebacking, big cock, blowjob, crossdressing

Chick's with dicks cum addict
4 months ago
6:52

xHamster

Chick's with dicks cum addict

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

Sissy Cums on BBC Vibrator
1 year ago
9:44

ShemaleSin

Sissy Cums on BBC Vibrator

Tags: amateur, anal, anal toying, big black cock, brunette, cum, cumshot

Crossdresser in Red Lingerie Fucks Hot Trans
9 months ago
1:23

xHamster

Crossdresser in Red Lingerie Fucks Hot Trans

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

Trans Babe Screws Trans Gal Bareback
2 months ago
3:50

ShemaleSin

Trans Babe Screws Trans Gal Bareback

Tags: amateur, anal, ass, babe, barebacking, feminization, homevideo

Sensual Secrets: Unveiling the Art of Seduction
1 year ago
6:17

xHamster

Sensual Secrets: Unveiling the Art of Seduction

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

cute tiny trans strokes until sexy cum
7 months ago
13:25

ShemaleSin

cute tiny trans strokes until sexy cum

Tags: amateur, big cock, close up, cowgirl, cum, cumshot, cute

Blonde Bailey Wilde Fucks Emo Jade Madison
4 months ago
1:03

xHamster

Blonde Bailey Wilde Fucks Emo Jade Madison

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

Trans Bailey Wilde Whipped
9 months ago
2:05

xHamster

Trans Bailey Wilde Whipped

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

YOUTHFUL DUDE ENDED UP BREAKING MY BUTT OUT OF LENIENCY, I SUFFERED WITH THAT LARGE RAMROD
55 days ago
6:16

ShemaleSin

YOUTHFUL DUDE ENDED UP BREAKING MY BUTT OUT OF LENIENCY, I SUFFERED WITH THAT LARGE RAMROD

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

Fashionable Femme: Inspiring Others with My Crossdressing Style!
1 year ago
5:19

xHamster

Fashionable Femme: Inspiring Others with My Crossdressing Style!

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

Fast femboy milking
43 days ago
1:23

xHamster

Fast femboy milking

Tags: amateur, anal, barebacking, big cock, blowjob, creampie, cum

Sissy shows herself
2 months ago
6:36

xHamster

Sissy shows herself

Tags: anal, beauty, big ass, big cock, crossdressing, cute, feminization

Sep 28th 2022
2 years ago
14:07

ShemaleSin

Sep 28th 2022

Tags: amateur, dildo, feminization, hd, masturbation, sissy, taboo

SIssy in red lingerie jerking off
4 months ago
1:20

xHamster

SIssy in red lingerie jerking off

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

Sissyboy Femboy boypussy destroyed getting pounded by sexmachine
7 months ago
1:18

xHamster

Sissyboy Femboy boypussy destroyed getting pounded by sexmachine

Tags: amateur, anal, anal toying, barebacking, creampie, crossdressing, dildo

Feminization, sissy
4 months ago
7:30

ShemaleTaxi

Feminization, sissy

Tags: feminization, shemale, sissy

Kris Kat – Entering The Feminization Academy
3 years ago
8:00

getTranny

Kris Kat – Entering The Feminization Academy

Tags: anal, big cock, blonde, crossdressing, deep throat, feminization, hd

The Hunk Piddled Inside My Open Butt with Speculum - Nicolly Summers (COMPLETE ON RED AND SHEER)
2 months ago
5:07

ShemaleSin

The Hunk Piddled Inside My Open Butt with Speculum - Nicolly Summers (COMPLETE ON RED AND SHEER)

Tags: amateur, anal, ass, barebacking, big black cock, feminization, hunk

Fucking my slut in the jacuzzi
8 months ago
8:25

xHamster

Fucking my slut in the jacuzzi

Tags: amateur, anal, big ass, big cock, blowjob, cum, cumshot

In shemale sluts we trust
8 months ago
7:47

xHamster

In shemale sluts we trust

Tags: amateur, anal, australian, barebacking, beauty, big cock, crossdressing

CUTE Transgender Fembot Femboy Gymnast Plays Anal Frontal then Tastes Her Cum ------ Preview
2 months ago
10:14

ShemaleSin

CUTE Transgender Fembot Femboy Gymnast Plays Anal Frontal then Tastes Her Cum ------ Preview

Tags: anal, cosplay, cum, cute, feminization, gym, gymnast

Sissy Femboy masturbation in the park
3 months ago
2:02

xHamster

Sissy Femboy masturbation in the park

Tags: amateur, anal, crossdressing, cum, feminization, ladyboy, lingerie

Melinda_JamesCD Whispers of Desire: An Invitation to Surrender
6 months ago
5:42

xHamster

Melinda_JamesCD Whispers of Desire: An Invitation to Surrender

Tags: amateur, beauty, big cock, crossdressing, feminization, german, hd

Shemale with her cousin fucking
2 months ago
5:18

xHamster

Shemale with her cousin fucking

Tags: amateur, big black cock, blowjob, crossdressing, cum, feminization, gangbang

Transgirl Live Stream Compilation
4 months ago
5:20

xHamster

Transgirl Live Stream Compilation

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

Crossdressing Fetish   Mature Sissy Trying On Dresses
10 months ago
8:55

xHamster

Crossdressing Fetish Mature Sissy Trying On Dresses

Tags: amateur, blonde, british, crossdressing, feminization, fetish, hd

VERY HOT Goth Sissy Sucking Cock POV
1 year ago
5:43

TrannyOne

VERY HOT Goth Sissy Sucking Cock POV

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

Mesmerizing Moves: Dancing to the Rhythm of Desire
1 year ago
5:35

xHamster

Mesmerizing Moves: Dancing to the Rhythm of Desire

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

Born this way FEMINIZATION TUTOR
5 months ago
31:15

ShemaleSin

Born this way FEMINIZATION TUTOR

Tags: amateur, anal, babe, brunette, feminization, hardcore, mom

Hot Crossdresser Pegged by Mistress Pixie
1 year ago
5:16

xHamster

Hot Crossdresser Pegged by Mistress Pixie

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

Sissy Trainer Sissy Mindset Reaffirmation Porn Obsession Sissification Feminization Instructions Sissy Way of Life
4 months ago
11:30

xHamster

Sissy Trainer Sissy Mindset Reaffirmation Porn Obsession Sissification Feminization Instructions Sissy Way of Life

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

Turning Him Into A Sissy Slut
1 year ago
4:04

TrannyOne

Turning Him Into A Sissy Slut

Tags: amateur, bitch, boyfriend, compilation, crossdressing, femdom, feminization

Hypnosissy
3 years ago
8:06

ShemaleSin

Hypnosissy

Tags: feminization, sissy

Goon with Sissy Jessika
10 months ago
5:00

xHamster

Goon with Sissy Jessika

Tags: amateur, anal, anal toying, bdsm, big ass, compilation, crossdressing

Huge Black Dildo Up To My Ass
5 months ago
7:18

xHamster

Huge Black Dildo Up To My Ass

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

Curvy Therapist Treats Trans Pair With 3some
2 months ago
13:07

ShemaleSin

Curvy Therapist Treats Trans Pair With 3some

Tags: 3some, barebacking, bbw, curvy, feminization, pain, tranny

Pink Haired CD Beauty Fucked
8 months ago
2:44

xHamster

Pink Haired CD Beauty Fucked

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

THAT GUY DRILLED MY BUTT FIRMLY AND THEN CUMMED ON MY FACE
2 months ago
9:57

ShemaleSin

THAT GUY DRILLED MY BUTT FIRMLY AND THEN CUMMED ON MY FACE

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Goth Tgirl Jade Madison Fucked Doggystyle
1 year ago
2:50

xHamster

Goth Tgirl Jade Madison Fucked Doggystyle

Tags: amateur, american, anal, beauty, big ass, big cock, blowjob

Big Booty Bimbo Fag
44 days ago
6:35

xHamster

Big Booty Bimbo Fag

Tags: bathroom, beauty, big ass, big cock, bimbo, booty, crossdressing

Trans Cutie Michelle Filling Her Cute Holes With Toys
5 months ago
7:36

ShemaleSin

Trans Cutie Michelle Filling Her Cute Holes With Toys

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Sissy Slut Strap on Fucked By Femdom Mistress - Jessica Bloom & Polieana Pegging
2 months ago
7:28

xHamster

Sissy Slut Strap on Fucked By Femdom Mistress - Jessica Bloom & Polieana Pegging

Tags: amateur, anal, anal toying, beauty, couple, creampie, crossdressing

BIG ASS Blonde TS Fucked Hard
1 year ago
3:59

xHamster

BIG ASS Blonde TS Fucked Hard

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

Melinda James Playing With a Snake
4 months ago
5:15

xHamster

Melinda James Playing With a Snake

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

Bailey Wilde Fucks Femboy Jasmyne Jaye Doggystyle
1 year ago
2:04

xHamster

Bailey Wilde Fucks Femboy Jasmyne Jaye Doggystyle

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

Daddy come play with me! 🥺
4 months ago
7:29

xHamster

Daddy come play with me! 🥺

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

Sissy Femboy Wench Hattabi4ik Squirt Climax Fun Compilation
2 months ago
1:54

ShemaleSin

Sissy Femboy Wench Hattabi4ik Squirt Climax Fun Compilation

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SISSY COW TRAIINNG to CUMSHOTS FREE HANDS
2 months ago
0:28

ShemaleSin

SISSY COW TRAIINNG to CUMSHOTS FREE HANDS

Tags: ass, bdsm, cum, cumshot, denial, domination, dominatrix

Lazy femboy bitch with gaping hole
1 year ago
1:58

xHamster

Lazy femboy bitch with gaping hole

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Goth Femboy Jade Madison Fucked Against Wall
1 year ago
2:46

xHamster

Goth Femboy Jade Madison Fucked Against Wall

Tags: amateur, american, anal, beauty, big ass, big cock, blowjob

Pretty in Pink - Mandi Mount
8 months ago
5:12

xHamster

Pretty in Pink - Mandi Mount

Tags: amateur, american, beauty, big cock, crossdressing, cum, cumshot

TS WILLOW - Pink Friday PAWG PMV
11 months ago
6:09

ShemaleSin

TS WILLOW - Pink Friday PAWG PMV

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Sexy crossdresser gaping and fisting
8 months ago
6:38

xHamster

Sexy crossdresser gaping and fisting

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2 Hottie Sissies Masturbating
11 months ago
2:03

xHamster

2 Hottie Sissies Masturbating

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

FCK M3 Like the floozy that u Know i'm - Official Music Movie scene - Emo Trans Beauty supplicates for Rod
38 days ago
11:01

ShemaleSin

FCK M3 Like the floozy that u Know i'm - Official Music Movie scene - Emo Trans Beauty supplicates for Rod

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white sissy gaping butthole with BBC dildo
5 months ago
1:40

xHamster

white sissy gaping butthole with BBC dildo

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Sissy Girl Jerking Off her Dick and a dildo
1 year ago
5:25

xHamster

Sissy Girl Jerking Off her Dick and a dildo

Tags: amateur, big cock, crossdressing, dick, dildo, feminization, fetish

"Come closer: feel the heat of this moment and let yourself be carried away by the passion"
10 months ago
5:39

xHamster

"Come closer: feel the heat of this moment and let yourself be carried away by the passion"

Tags: amateur, anal, crossdressing, dress, feminization, german, handjob

Goth Crossdresser Pegged and Swallows Own Cum
4 months ago
10:08

xHamster

Goth Crossdresser Pegged and Swallows Own Cum

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

Dreaming of Marriage: Building a Future with a Girl
1 year ago
5:26

xHamster

Dreaming of Marriage: Building a Future with a Girl

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

I was caught in the kitchen recording content, I thought my boyfriend was plan to fight but this chab put me on the sink and banged me...
15 days ago
14:16

ShemaleSin

I was caught in the kitchen recording content, I thought my boyfriend was plan to fight but this chab put me on the sink and banged me...

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Feminization - Sissy Training - Sissy task - Going to a sex discharged
1 year ago
6:08

ShemaleSin

Feminization - Sissy Training - Sissy task - Going to a sex discharged

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Cute Slender Sissy Femboy Trap with flawless body jerking off and cum - Jizz Flow
2 years ago
2:17

ShemaleSin

Cute Slender Sissy Femboy Trap with flawless body jerking off and cum - Jizz Flow

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Effeminate transsexual ass transvestite in skirt heats up with her ass shows ass
5 months ago
16:10

xHamster

Effeminate transsexual ass transvestite in skirt heats up with her ass shows ass

Tags: amateur, anal, ass, big ass, booty, colombian, creampie

Sissy in red lingerie locked onto her dildo stand with big black dildo
7 months ago
32:59

xHamster

Sissy in red lingerie locked onto her dildo stand with big black dildo

Tags: amateur, american, black, bondage, crossdressing, dildo, feminization

Mistress Lets Sissy Squirt In Cage
7 months ago
1:52

xHamster

Mistress Lets Sissy Squirt In Cage

Tags: amateur, bdsm, cage, crossdressing, cum, cumshot, domination

Homemade Compilation: Celebrating my Feminine Side
1 year ago
5:37

xHamster

Homemade Compilation: Celebrating my Feminine Side

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

Sexy Pretty E-Girl Tranny Jerk herself LEAKS
5 months ago
1:20

xHamster

Sexy Pretty E-Girl Tranny Jerk herself LEAKS

Tags: beauty, big cock, blonde, compilation, cosplay, cum, feminization

BIGGEST JIZZ FLOW from BBC
2 months ago
0:19

ShemaleSin

BIGGEST JIZZ FLOW from BBC

Tags: anal, big black cock, couple, dildo, domination, dominatrix, femdom

Sissy in micro bikini drinking 1l of beer via anal and then pushing it out
10 months ago
7:56

xHamster

Sissy in micro bikini drinking 1l of beer via anal and then pushing it out

Tags: amateur, anal, ass, bathroom, bikini, crossdressing, feminization

Trixy call a mechanic guy who fucks her hard....
5 months ago
9:05

xHamster

Trixy call a mechanic guy who fucks her hard....

Tags: amateur, anal, barebacking, beauty, big black cock, big cock, blowjob

Cheerleader sucks and fucks
3 months ago
2:46

xHamster

Cheerleader sucks and fucks

Tags: amateur, anal, australian, barebacking, beauty, big cock, cheerleader

Come watch me at home, editing my episodes and stroking for u.
2 months ago
10:22

ShemaleSin

Come watch me at home, editing my episodes and stroking for u.

Tags: feminization, homevideo, milf, stroking, tranny, transsexual

A blowjob for you
1 year ago
6:20

xHamster

A blowjob for you

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Sissy Maid Sucks On Her Dildo then Slaps Her Balls With It!
5 months ago
1:09

xHamster

Sissy Maid Sucks On Her Dildo then Slaps Her Balls With It!

Tags: amateur, american, balls, bbw, bdsm, blonde, blowjob

Asian Femboy Nylon JOI with Jerk Off And Cumming
5 months ago
9:50

xHamster

Asian Femboy Nylon JOI with Jerk Off And Cumming

Tags: amateur, asian, crossdressing, cum, feminization, german, hd

Sexy Blonde Trans Bailey Wilde Fucked
58 days ago
3:45

xHamster

Sexy Blonde Trans Bailey Wilde Fucked

Tags: amateur, american, anal, barebacking, big cock, blonde, crossdressing

Mistress Turns A Guy Into Sissy And Make Him Fucked With Lindsey Love
1 year ago
16:51

TrannyOne

Mistress Turns A Guy Into Sissy And Make Him Fucked With Lindsey Love

Tags: feminization, mistress, shemale, sissy, slut

Lingerie at work
23 days ago
2:11

xHamster

Lingerie at work

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

Sex Machine Fucks Hot Trans Bailey Wilde
1 year ago
9:19

xHamster

Sex Machine Fucks Hot Trans Bailey Wilde

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

Travesti tania gets deep dildoing pounding
9 months ago
6:33

xHamster

Travesti tania gets deep dildoing pounding

Tags: amateur, anal toying, ass, big black cock, dildo, feminization, hd

Crossdresser 1st Anal-act of love and Oral pleasure
7 months ago
3:21

ShemaleSin

Crossdresser 1st Anal-act of love and Oral pleasure

Tags: amateur, anal, bdsm, big tits, blowjob, booty, crossdressing

Transgirl Tries to Fit 20Inch Toy
1 year ago
7:08

xHamster

Transgirl Tries to Fit 20Inch Toy

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Close up anal
24 days ago
10:42

ShemaleSin

Close up anal

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Feminization- Guy Becomes Menina
2 years ago
2:54

getTranny

Feminization- Guy Becomes Menina

Tags: amateur, bdsm, brunette, deep throat, femdom, feminization, group sex

BTS Interview about Ms Minxys Eternal Bareback Submission
5 months ago
19:00

xHamster

BTS Interview about Ms Minxys Eternal Bareback Submission

Tags: anal, barebacking, beauty, blonde, blowjob, british, couple

Sexy Dominant Trans Woman Fucks Man
6 months ago
7:03

xHamster

Sexy Dominant Trans Woman Fucks Man

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

VERY SEXY Blonde Bailey Wilde Fucked Hard Doggystyle
1 year ago
7:41

xHamster

VERY SEXY Blonde Bailey Wilde Fucked Hard Doggystyle

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

Shemale Cumshot and Sissygasm Compilation
4 months ago
8:33

xHamster

Shemale Cumshot and Sissygasm Compilation

Tags: amateur, anal, beauty, big cock, compilation, crossdressing, cum

Precious times with Mistresse for MilkySlave
2 months ago
16:08

ShemaleSin

Precious times with Mistresse for MilkySlave

Tags: bdsm, cage, cfnm, cum, denial, feminization, fetish

Sissy Shelby Kiss Anal Compilation
4 months ago
7:44

xHamster

Sissy Shelby Kiss Anal Compilation

Tags: amateur, american, anal, anal toying, bbw, compilation, crossdressing

Gagging, Drooling, and Begging For Greater amount Whilst Hude Sex toy Wrecks My Mouth
2 months ago
9:44

ShemaleSin

Gagging, Drooling, and Begging For Greater amount Whilst Hude Sex toy Wrecks My Mouth

Tags: amateur, anal, ass, doggystyle, drooling, feminization, gagging

Femboy Elena Koslov's XL Sex-toy Oral pleasure Teaser #1
9 months ago
0:24

ShemaleSin

Femboy Elena Koslov's XL Sex-toy Oral pleasure Teaser #1

Tags: amateur, big cock, blonde, blowjob, dildo, feminization, gagging

SEXIEST Trans Latina Fucked Doggystyle
1 year ago
6:34

xHamster

SEXIEST Trans Latina Fucked Doggystyle

Tags: amateur, american, anal, ass, beauty, big ass, big tits

The Lost Bet
2 months ago
1:28

xHamster

The Lost Bet

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Sexy Blonde Sissy Fucking Redhead Trans Woman Bareback
11 months ago
1:44

xHamster

Sexy Blonde Sissy Fucking Redhead Trans Woman Bareback

Tags: amateur, american, anal, barebacking, big ass, big cock, blonde

this nurse, a slut who likes vibrating plug in her ass
7 months ago
5:39

xHamster

this nurse, a slut who likes vibrating plug in her ass

Tags: anal, anal toying, ass, big cock, crossdressing, dildo, european