Feel free to Save, Share, and use my captions anywhere for everything hehe.
3 years ago
1:50

ShemaleSin

Feel free to Save, Share, and use my captions anywhere for everything hehe.

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1 year ago
16:15

KeekAss

lily starlet tgirl gimp made to fart on vid and plow chest nymph

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3 years ago
5:06

ShemaleSin

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1 year ago
5:02

ShemaleSin

Costume held up by bag, I didn't notice

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Crimson Mini-Sundress and High High-Heeled Slippers - Crossdresser in public
2 years ago
2:03

KeekAss

Crimson Mini-Sundress and High High-Heeled Slippers - Crossdresser in public

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Two mature moms femdom feminization sissyboy part3
2 years ago
12:55

TrannyOne

Two mature moms femdom feminization sissyboy part3

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Kylie's Climax (woman mask, mask, tights, garters, trans, crossdress, feminization)
3 years ago
19:21

KeekAss

Kylie's Climax (woman mask, mask, tights, garters, trans, crossdress, feminization)

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Trap dominated in anal sex, sissy feminization
1 year ago
5:32

ShemaleTaxi

Trap dominated in anal sex, sissy feminization

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3 years ago
0:18

ShemaleSin

Meaty bang for nice-looking sissy wench- full movie on my Onlyfans (link in bio)

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Mastix Mercers Sissy Floozy Doll - Stream highlights - Oral Pleasure Practice ????
2 years ago
1:13

ShemaleSin

Mastix Mercers Sissy Floozy Doll - Stream highlights - Oral Pleasure Practice ????

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Sissy Feminization
3 years ago
14:04

TrannyOne

Sissy Feminization

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Kym Unpacks her Schlong (trans, Female Mask, Mask, Hose, Crossdress, Disclose, Transformation)
4 years ago
4:24

ShemaleSin

Kym Unpacks her Schlong (trans, Female Mask, Mask, Hose, Crossdress, Disclose, Transformation)

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Slaver t-girl Mistresse Holly Hunt controls how u jerk off and counts down to u eating your own cum, sissyfication and feminization. For the full clip
1 year ago
3:06

ShemaleSin

Slaver t-girl Mistresse Holly Hunt controls how u jerk off and counts down to u eating your own cum, sissyfication and feminization. For the full clip

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Pink Juggsy in 44 R Cup Brassiere
4 years ago
5:17

ShemaleSin

Pink Juggsy in 44 R Cup Brassiere

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Feminized Tranny
4 years ago
20:07

TrannyOne

Feminized Tranny

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Naughty sissy attempts to do well, but sans success, not a droplet :) 1/2
2 years ago
15:42

KeekAss

Naughty sissy attempts to do well, but sans success, not a droplet :) 1/2

Tags: anal, crossdressing, fetish, hd, masturbation

Pornstars: lystra

AlsoNicole Pumps up her sissy bazookas to show her further Feminization. Grwoing her melons to no longer be acceptable as a stud and merely seen as a
4 years ago
3:39

ShemaleSin

AlsoNicole Pumps up her sissy bazookas to show her further Feminization. Grwoing her melons to no longer be acceptable as a stud and merely seen as a

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Sissy Fashion: Rocking Your Feminine Style
1 year ago
5:40

xHamster

Sissy Fashion: Rocking Your Feminine Style

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Crossdresser drilled pants into her butt
1 year ago
8:34

ShemaleSin

Crossdresser drilled pants into her butt

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Inexperienced Slut was Destroyed with Large Ding-Dong- Full Movie Scene on my Onlyfans (link in bio)
3 years ago
0:18

ShemaleSin

Inexperienced Slut was Destroyed with Large Ding-Dong- Full Movie Scene on my Onlyfans (link in bio)

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Cute Sissy Femboy - Anal Large Vibrator - creampie - sissygasm - sissy climax - hands free cum
2 years ago
2:47

ShemaleSin

Cute Sissy Femboy - Anal Large Vibrator - creampie - sissygasm - sissy climax - hands free cum

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Crossdresser Willing to get Screwed Doggy Position
4 years ago
0:34

ShemaleSin

Crossdresser Willing to get Screwed Doggy Position

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Sissy Natasha squirts & piddles out of chastity caged schlong from Lovense sex machine screwing!
2 years ago
3:35

ShemaleSin

Sissy Natasha squirts & piddles out of chastity caged schlong from Lovense sex machine screwing!

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Lily Starlet Takes knuckle and mini-rosebud for highly first-ever time!
1 year ago
10:22

KeekAss

Lily Starlet Takes knuckle and mini-rosebud for highly first-ever time!

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Your sissy maid
2 years ago
19:47

ShemaleSin

Your sissy maid

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Dude Feminized by Girlfriend
4 years ago
2:48

ShemaleSin

Dude Feminized by Girlfriend

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Underware Wearing Trans Woman
4 years ago
1:12

ShemaleSin

Underware Wearing Trans Woman

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Crossdressers Having Fun
3 years ago
2:19:39

TrannyOne

Crossdressers Having Fun

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Pathetic sissy crossdressing ramrod worship
1 year ago
0:41

ShemaleSin

Pathetic sissy crossdressing ramrod worship

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Alisa crossdresser
3 years ago
1:08

xHamster

Alisa crossdresser

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Girlfriend Makes boyfriend to Suit as a Woman for the Weekend
4 years ago
0:33

ShemaleSin

Girlfriend Makes boyfriend to Suit as a Woman for the Weekend

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SissyMia wrecked sissygasm and Long leakage
3 years ago
5:08

KeekAss

SissyMia wrecked sissygasm and Long leakage

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Crossdresser She-Creature Massager Restrain Bondage
2 years ago
4:57

KeekAss

Crossdresser She-Creature Massager Restrain Bondage

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Behind My Neighbor House Squirting On His Ring Cam Cause He Stay Watching ME
1 year ago
5:49

TrannyOne

Behind My Neighbor House Squirting On His Ring Cam Cause He Stay Watching ME

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Hawt Feminization Transformation
3 years ago
6:49

ShemaleSin

Hawt Feminization Transformation

Tags: crossdressing, feminization, transsexual

Dec 2nd 2022
2 years ago
22:36

ShemaleSin

Dec 2nd 2022

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Sissy Marissa buys a fuck machine
1 year ago
9:45

xHamster

Sissy Marissa buys a fuck machine

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Plugged and caged
2 years ago
8:55

ShemaleSin

Plugged and caged

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Frilly undies upskirt
1 year ago
6:25

KeekAss

Frilly undies upskirt

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Sissy anal hypno training video
1 year ago
11:54

aShemaleTube

Sissy anal hypno training video

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Feminized t-girl gets cooter porked
1 year ago
5:30

KeekAss

Feminized t-girl gets cooter porked

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screwing my butt with biig dildos and a fuckmachine - sissy in cage
1 year ago
5:31

ShemaleSin

screwing my butt with biig dildos and a fuckmachine - sissy in cage

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Samantha sissy talk ribald 'cuz your knob is pathetic, the feminization is inevitable
3 years ago
6:56

ShemaleSin

Samantha sissy talk ribald 'cuz your knob is pathetic, the feminization is inevitable

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Feminization, Makeup, Sissy Crossdressing for Your Step Daddy
1 year ago
2:15

ShemaleSin

Feminization, Makeup, Sissy Crossdressing for Your Step Daddy

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Pornstars: viper

large jock in booty
2 years ago
0:24

ShemaleSin

large jock in booty

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Cheap sissy doxy aperture training- full movie scene on my Onlyfans (link In bio)
2 years ago
0:23

ShemaleSin

Cheap sissy doxy aperture training- full movie scene on my Onlyfans (link In bio)

Tags: anal, bdsm, domination, femdom, goddess

I sundress him with my stockings and pummel his bum.... PEGGING & CROSSDRESSING
2 years ago
25:12

KeekAss

I sundress him with my stockings and pummel his bum.... PEGGING & CROSSDRESSING

Tags: anal, blowjob, crossdressing, femdom, fetish

sissy sonya on gynochair nailed by drilling machine
2 years ago
5:03

KeekAss

sissy sonya on gynochair nailed by drilling machine

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Walking to the gym in my leggings
1 year ago
12:08

ShemaleSin

Walking to the gym in my leggings

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Kimono Smooch Stunner Wants Manmeat
3 years ago
6:16

KeekAss

Kimono Smooch Stunner Wants Manmeat

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Wife sexy lingerie cumshot
2 years ago
2:40

xHamster

Wife sexy lingerie cumshot

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Sissy Sex Toy Ride
2 years ago
4:22

ShemaleSin

Sissy Sex Toy Ride

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Golden-Haired Trans Woman Fucked 
4 years ago
9:52

ShemaleSin

Golden-Haired Trans Woman Fucked 

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Become Pornosexual Design your Flawless Industrial Porn Program- #JustREC
4 years ago
2:57:55

ShemaleSin

Become Pornosexual Design your Flawless Industrial Porn Program- #JustREC

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In this astounding 7 day guide, I guide u throughout the process of sissification. Every day, I give u a recent gripping task to complete.Merely by re
3 years ago
30:00

ShemaleSin

In this astounding 7 day guide, I guide u throughout the process of sissification. Every day, I give u a recent gripping task to complete.Merely by re

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Sheila's Shoe Fetish Session (trans, Shoes, High Heels, Hose, Female Mask, Mask, Transform)
4 years ago
4:58

ShemaleSin

Sheila's Shoe Fetish Session (trans, Shoes, High Heels, Hose, Female Mask, Mask, Transform)

Tags: ass, brunette, crossdressing, feet, fetish

Told my sissy marionette to put me on a flash
2 years ago
4:32

KeekAss

Told my sissy marionette to put me on a flash

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Dec 8th 2022
2 years ago
10:05

ShemaleSin

Dec 8th 2022

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Hot sissy girly dancing near couch in fantastic underware
3 years ago
4:29

ShemaleSin

Hot sissy girly dancing near couch in fantastic underware

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Mar 20th 2022
3 years ago
9:44

ShemaleSin

Mar 20th 2022

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Tail plugged crossdresser out for a walk in the forest
1 year ago
2:37

ShemaleSin

Tail plugged crossdresser out for a walk in the forest

Tags: anal, ass, big ass, crossdressing, forest

Sissy upskirt twerk
2 years ago
8:39

ShemaleSin

Sissy upskirt twerk

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femboy goes deeper into porn (crossdresser sissy trap)
3 years ago
1:26

TrannyOne

femboy goes deeper into porn (crossdresser sissy trap)

Tags: adorable, american, bdsm, crossdressing, feminization

May in October
2 years ago
11:50

ShemaleSin

May in October

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Una femboy linda terminar de hacer un gran baile
2 years ago
3:46

KeekAss

Una femboy linda terminar de hacer un gran baile

Tags: anal, big ass, crossdressing, femdom, gay

Quite wicked! Monnica is being bimbofied and sissified by her Dominatrix-Bitch Wife, Dominatrix-Bitch Violet. What more excellent way to celebrate it
1 year ago
8:40

ShemaleSin

Quite wicked! Monnica is being bimbofied and sissified by her Dominatrix-Bitch Wife, Dominatrix-Bitch Violet. What more excellent way to celebrate it

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1 year ago
6:57

ShemaleSin

fine butt out for a walk

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This Babe have pleasure with her weenie-beauty
2 years ago
2:27

ShemaleSin

This Babe have pleasure with her weenie-beauty

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Dominatrix Feminizes Sissy into Maid
1 year ago
5:01

xHamster

Dominatrix Feminizes Sissy into Maid

Tags: american, anal, bdsm, domination, dominatrix

Makeup Fetish, Glam, Transvestic Fetish, Crossdress, Feminization, Blow Job, PMV, Lipstick, Transvestite, TV, CD, Oral Job, Anal, EDM
4 years ago
6:03

ShemaleSin

Makeup Fetish, Glam, Transvestic Fetish, Crossdress, Feminization, Blow Job, PMV, Lipstick, Transvestite, TV, CD, Oral Job, Anal, EDM

Tags: anal, blowjob, crossdressing, fetish, mature

Cheap sissy bitch gap training- full movie scene on my Onlyfans (link In bio)
3 years ago
0:23

ShemaleSin

Cheap sissy bitch gap training- full movie scene on my Onlyfans (link In bio)

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Miss Ellen
2 years ago
9:51

ShemaleSin

Miss Ellen

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Sandy, cd, pounds the masons of her renovation.
2 years ago
17:17

KeekAss

Sandy, cd, pounds the masons of her renovation.

Tags: anal, assfucking, blowjob, brunette, creampie

Wery bad sissy out of chastity
3 years ago
0:24

ShemaleSin

Wery bad sissy out of chastity

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Pornstars: lystra

Crossdresser ding-dong drilled
4 years ago
5:00

ShemaleSin

Crossdresser ding-dong drilled

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POV Screw my sissy male in chastity
2 years ago
5:16

ShemaleSin

POV Screw my sissy male in chastity

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Addibabeee Plays with herself while she rivulets
2 years ago
11:50

KeekAss

Addibabeee Plays with herself while she rivulets

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I Love Turning Myself Into a Promiscuous Spandex Housewife
2 years ago
2:14

KeekAss

I Love Turning Myself Into a Promiscuous Spandex Housewife

Tags: big tits, crossdressing, hd, homevideo, spandex

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

ShemaleSin

Sissy Training female energy (english voice)

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Girlfriend Makes Sissy Boyfriend to go on Date with Guy
4 years ago
0:24

ShemaleSin

Girlfriend Makes Sissy Boyfriend to go on Date with Guy

Tags: babe, blonde, boy, boyfriend, crossdressing

SOFIE AND VICKY BEING BREAKING IN BY 2 BBC! THEY HAD NO PITY! WE LOVE IT!
1 year ago
10:11

ShemaleSin

SOFIE AND VICKY BEING BREAKING IN BY 2 BBC! THEY HAD NO PITY! WE LOVE IT!

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Sissy forgets to turn cam off after stream
1 year ago
0:47

ShemaleSin

Sissy forgets to turn cam off after stream

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Hawt Blond Trans Woman Willing to be Screwed
4 years ago
1:04

ShemaleSin

Hawt Blond Trans Woman Willing to be Screwed

Tags: anal, babe, big cock, big tits, blonde

Pegging my sissy bitch balls unfathomable
2 years ago
4:11

ShemaleSin

Pegging my sissy bitch balls unfathomable

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Two Boys Crossdressing and Fucking
4 years ago
12:21

TrannyOne

Two Boys Crossdressing and Fucking

Tags: bdsm, boy, crossdressing, feminization, transvestite

I Love the Smack of My Own Butt Juices, Especally Whilst Locked in Chastity!
1 year ago
6:23

ShemaleSin

I Love the Smack of My Own Butt Juices, Especally Whilst Locked in Chastity!

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Sissy Maid Public Outing
2 years ago
0:51

ShemaleSin

Sissy Maid Public Outing

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Vintage Feminization
4 years ago
19:29

TrannyOne

Vintage Feminization

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He Made Me Do It Again! I'm a Sissy Mega-Slut! Feminization
2 years ago
2:15

KeekAss

He Made Me Do It Again! I'm a Sissy Mega-Slut! Feminization

Tags: brunette, crossdressing, fetish, hd, lingerie

A HOT TRANSVESTITE HIDES a METAL CHASTITY THONG UNDERNEATH TIGHTS AND a PETTICOAT AND GOES ON a DATE
4 years ago
9:00

ShemaleSin

A HOT TRANSVESTITE HIDES a METAL CHASTITY THONG UNDERNEATH TIGHTS AND a PETTICOAT AND GOES ON a DATE

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Sissy Deep-Throat Instructing Time!
3 years ago
5:24

KeekAss

Sissy Deep-Throat Instructing Time!

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Sissygasm - Joanna cums hands free - Bullet Sex-Toy on Clitoris - Feminization Sissy
1 year ago
5:34

ShemaleSin

Sissygasm - Joanna cums hands free - Bullet Sex-Toy on Clitoris - Feminization Sissy

Tags: cum, masturbation, pov, sissy, slut

ASIAN SHEMALE LEITAOXIV CUMMING WITHOUT TOUCHING HER COCK
8 months ago
1:30

xHamster

ASIAN SHEMALE LEITAOXIV CUMMING WITHOUT TOUCHING HER COCK

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nice-looking trans domina plays with her delicious body
1 year ago
5:39

ShemaleSin

nice-looking trans domina plays with her delicious body

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

ShemaleSin

Bisex Crossdressing And Femdom Dream Movie Scenes

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CD whore loves daddies raw cock
3 years ago
8:11

TrannyOne

CD whore loves daddies raw cock

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Female-Dom pegs sissy catgirl in booty
3 years ago
7:05

ShemaleSin

Female-Dom pegs sissy catgirl in booty

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Crossdresser Willing to get Banged in Living Room
4 years ago
1:28

ShemaleSin

Crossdresser Willing to get Banged in Living Room

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Sissy does butt to throat with her toys.
1 year ago
5:54

ShemaleSin

Sissy does butt to throat with her toys.

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Oriental Sissy T-Girl Ladyboy Dancing and Showing her Body
4 years ago
2:48

ShemaleSin

Oriental Sissy T-Girl Ladyboy Dancing and Showing her Body

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Apr ninth 2023
2 years ago
21:46

ShemaleSin

Apr ninth 2023

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Sissy Masturbating Off Her Yam-Sized Weenie Dressed In Spandex Mittens and a Tutu Sundress
2 years ago
8:46

KeekAss

Sissy Masturbating Off Her Yam-Sized Weenie Dressed In Spandex Mittens and a Tutu Sundress

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Crossdresser gagged and anal
2 years ago
12:47

ShemaleSin

Crossdresser gagged and anal

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Trap80 with fuckmachine
2 years ago
5:24

KeekAss

Trap80 with fuckmachine

Tags: anal, anal toying, ass, big ass, crossdressing

Mischievous Femboy Biotch Screws a Large BIG BLACK COCK Fuck Stick while Locked in V-Card Box
2 years ago
2:58

KeekAss

Mischievous Femboy Biotch Screws a Large BIG BLACK COCK Fuck Stick while Locked in V-Card Box

Tags: anal, anal toying, beauty, big black cock, crossdressing

Transgirl Finds out about your Sissy Side and Shares her Raiment
4 years ago
2:37

ShemaleSin

Transgirl Finds out about your Sissy Side and Shares her Raiment

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Sissy Transformation Ft Trans Femdom Queen
4 years ago
1:17

ShemaleSin

Sissy Transformation Ft Trans Femdom Queen

Tags: babe, blonde, femdom, feminization, fetish

Sissy Bitch & BBC Ass Bumpin Magic
3 years ago
5:50

ShemaleSin

Sissy Bitch & BBC Ass Bumpin Magic

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PsychodelicSissy two
4 years ago
7:16

ShemaleSin

PsychodelicSissy two

Tags: feminization, sissy

Apr 22nd 2023
2 years ago
17:29

ShemaleSin

Apr 22nd 2023

Tags: anal, assfucking, brunette, dildo, feminization

ARE YOU TRULY A STUD??  teaching feminization transgirl
3 years ago
5:06

KeekAss

ARE YOU TRULY A STUD?? teaching feminization transgirl

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Vixen squirts all over herself for her taskmaster w/dildo
2 years ago
22:17

ShemaleSin

Vixen squirts all over herself for her taskmaster w/dildo

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Sissy Giving Daddy Smoking Blowjob
3 years ago
17:02

TrannyOne

Sissy Giving Daddy Smoking Blowjob

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Soiree Doll Wants Pecker at the Pub
3 years ago
13:32

KeekAss

Soiree Doll Wants Pecker at the Pub

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Sissy teases rides and cums
3 years ago
1:40

ShemaleSin

Sissy teases rides and cums

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Dom CD Shemale Drag Queen Feminization Mastix become my Sissy Wench
4 years ago
2:58

ShemaleSin

Dom CD Shemale Drag Queen Feminization Mastix become my Sissy Wench

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CD Mask Film Noir
4 years ago
3:36

ShemaleSin

CD Mask Film Noir

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Crossdresser getting Willing to get Banged
4 years ago
1:48

ShemaleSin

Crossdresser getting Willing to get Banged

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Mrs R Boudoir Visit (trans, Feminization, Female Mask, Mask, Crossdress, Transformation, big beautiful woman)
4 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

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

ShemaleSin

POV Hot Golden-Haired Crossdresser Sucking Shlong

Tags: blonde, blowjob, crossdressing, dress, femdom

Romina's Gyrations (female Mask, Mask, Fetish, Trans, Crossdress, Transformation, Hose, Heels)
4 years ago
13:36

ShemaleSin

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3 years ago
4:01

ShemaleSin

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3 years ago
1:36

ShemaleSin

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4 years ago
0:23

ShemaleSin

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2 years ago
5:16

ShemaleSin

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3 years ago
3:21

TrannyOne

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3 years ago
3:12

ShemaleSin

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3 years ago
0:18

ShemaleSin

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2 years ago
2:06

ShemaleSin

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1 year ago
0:16

ShemaleSin

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2 years ago
1:54

ShemaleSin

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4 years ago
6:48

ShemaleSin

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3 years ago
5:42

KeekAss

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3 years ago
10:24

KeekAss

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3 years ago
31:52

KeekAss

Feminized Ladyboy Gets Insatiable

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3 years ago
23:23

KeekAss

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5 years ago
4:59

KeekAss

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5 years ago
10:06

KeekAss

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5 years ago
8:13

KeekAss

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3 years ago
25:29

KeekAss

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5 years ago
6:19

ShemaleMovie

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3 years ago
4:01

KeekAss

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3 years ago
11:23

KeekAss

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3 years ago
3:12

KeekAss

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3 years ago
14:04

KeekAss

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4 years ago
7:24

ShemaleTaxi

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6 years ago
10:49

KeekAss

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5 years ago
3:17

aShemaleTube

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3 years ago
4:09

KeekAss

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5 years ago
28:50

KeekAss

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3 years ago
7:52

ShemaleSin

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3 years ago
5:13

ShemaleTaxi

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3 years ago
7:07

KeekAss

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3 years ago
3:10

KeekAss

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5 years ago
7:21

ShemaleTaxi

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3 years ago
4:05

KeekAss

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3 years ago
9:49

ShemaleMovie

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4 years ago
0:39

aShemaleTube

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4 years ago
15:44

KeekAss

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4 years ago
14:19

KeekAss

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6 years ago
7:11

KeekAss

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3 years ago
4:24

KeekAss

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3 years ago
7:27

KeekAss

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3 years ago
13:10

KeekAss

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Utter Crossdressing Transformation
3 years ago
10:13

KeekAss

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4 years ago
14:42

ShemaleSin

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*Trailer* Sissy Teaching Basics With Kelli Frost
3 years ago
11:15

KeekAss

*Trailer* Sissy Teaching Basics With Kelli Frost

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Feminized Ladyboy Needs To Rail Knob
3 years ago
5:12

KeekAss

Feminized Ladyboy Needs To Rail Knob

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3 years ago
3:29

KeekAss

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3 years ago
2:17

KeekAss

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3 years ago
7:18

KeekAss

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5 years ago
6:15

ShemaleTaxi

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3 years ago
6:45

KeekAss

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Thyra the Tigress (trans, crossdress, transformation, tights, feminization, mask, chick mask)
3 years ago
18:13

KeekAss

Thyra the Tigress (trans, crossdress, transformation, tights, feminization, mask, chick mask)

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3 years ago
22:32

KeekAss

CRIMSON LATEXDOLL ONANISM #1

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3 years ago
12:30

KeekAss

Trans Angel Undergarments Starlet

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3 years ago
15:11

KeekAss

Sumptuous Gal Bare Taking a Bathroom

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5 years ago
7:00

ShemaleTaxi

Hypno, feminization

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3 years ago
5:50

ShemaleMovie

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Pretty In Rosy Ladylike Trans Wants To Have Fun
3 years ago
20:39

KeekAss

Pretty In Rosy Ladylike Trans Wants To Have Fun

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