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1 year ago
5:50

PornHub

Gentle anal for blonde transgirl part 1

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Sissy Slut Riding Dick After Too Many Captions
1 year ago
9:42

PornHub

Sissy Slut Riding Dick After Too Many Captions

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10 months ago
17:17

KeekAss

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1 year ago
7:18

PornHub

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1 year ago
17:06

PornHub

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1 year ago
3:23

PornHub

GIRL FUCKS A TRANSGENDER. I WANT TO FUCK YOUR ANAL HOLE WHILE YOUR COCK IS IN THE CHASTITY BELT

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6 months ago
11:54

aShemaleTube

Sissy anal hypno training video

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2 years ago
1:03

ShemaleSin

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2 years ago
0:24

ShemaleSin

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TS Willow Hammerz - Sexy SIssy Girl Dick w/ Cumshot
1 year ago
7:41

PornHub

TS Willow Hammerz - Sexy SIssy Girl Dick w/ Cumshot

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Sissy Dolly Dungeon Play Time Pegged by Huge Bad Dragon Strapon and Humiliated by Mistress Mercer
1 year ago
3:59

PornHub

Sissy Dolly Dungeon Play Time Pegged by Huge Bad Dragon Strapon and Humiliated by Mistress Mercer

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3 years ago
6:03

ShemaleSin

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1 year ago
2:13

PornHub

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9 months ago
5:16

ShemaleSin

POV Screw my sissy male in chastity

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Feminization -Sissification - Sissy Training - SISSY TRIP
11 months ago
8:44

PornHub

Feminization -Sissification - Sissy Training - SISSY TRIP

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Dominatrix Feminizes Sissy into Maid
6 months ago
5:01

xHamster

Dominatrix Feminizes Sissy into Maid

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1 year ago
0:34

PornHub

Sissy slut rides Mistress backwards cowgirl

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1 year ago
3:46

KeekAss

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Tucked Away (a gender bender animation)
1 year ago
1:01

PornHub

Tucked Away (a gender bender animation)

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7 months ago
5:03

KeekAss

sissy sonya on gynochair nailed by drilling machine

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Feminization Sissy Training Sissy Task - Lingerie Store
10 months ago
3:31

PornHub

Feminization Sissy Training Sissy Task - Lingerie Store

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Hawt Sissy Ponyboy with Tiny Love Button in Blue Hose and High Heels trying to Dance in the Car
2 years ago
6:57

ShemaleSin

Hawt Sissy Ponyboy with Tiny Love Button in Blue Hose and High Heels trying to Dance in the Car

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Screw Your Butt - Sissy Training (Sissy Audio Hypnose)
2 years ago
12:01

ShemaleSin

Screw Your Butt - Sissy Training (Sissy Audio Hypnose)

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2 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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Feminization - sissy training - part 2 (english voice)
2 years ago
4:17

PornHub

Feminization - sissy training - part 2 (english voice)

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5 months ago
8:34

ShemaleSin

Crossdresser drilled pants into her butt

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Sissy Rides a Sex Toy
2 years ago
6:53

ShemaleSin

Sissy Rides a Sex Toy

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1 year ago
20:51

PornHub

sissy in chastity pounds pussy hard until she makes cummies

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1 year ago
1:59

ShemaleSin

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Dec 2nd 2022
1 year ago
22:36

ShemaleSin

Dec 2nd 2022

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1 year ago
21:46

ShemaleSin

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11 months ago
12:55

TrannyOne

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Chillout Erotica Ep.1 (compilation, Trainer, Feminization, Sissy, Fetish)
2 years ago
6:18

TrannyOne

Chillout Erotica Ep.1 (compilation, Trainer, Feminization, Sissy, Fetish)

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Dude Feminized by Girlfriend
2 years ago
2:48

ShemaleSin

Dude Feminized by Girlfriend

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

ShemaleSin

Golden-Haired Trans Woman Fucked 

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

ShemaleSin

Become Pornosexual Design your Flawless Industrial Porn Program- #JustREC

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Tgirl shaves for her feminization process and cum out of hands
2 years ago
1:00

ShemaleSin

Tgirl shaves for her feminization process and cum out of hands

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Hawt Crossdresser Screwed from Behind
1 year ago
1:02

ShemaleSin

Hawt Crossdresser Screwed from Behind

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1 year ago
7:17

PornHub

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1 year ago
6:25

PornHub

Femboy masturbate with vibrator thru cute and wet diaper. ( it's a real pleasure 😉)

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femboy and tgirl spitroast an emo boy
11 months ago
1:33

PornHub

femboy and tgirl spitroast an emo boy

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(LGBTQI+) U'll Be My Lady (erotic audio play by OolayTiger)
2 years ago
20:39

ShemaleSin

(LGBTQI+) U'll Be My Lady (erotic audio play by OolayTiger)

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Crossdresser Makeover Transformation into Woman by Girlfriend
2 years ago
0:31

ShemaleSin

Crossdresser Makeover Transformation into Woman by Girlfriend

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My precious serf! (feminization - Femboy )
1 year ago
1:03

ShemaleSin

My precious serf! (feminization - Femboy )

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3 years ago
5:00

ShemaleSin

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Addibabeee Plays with herself while she rivulets
1 year ago
11:50

KeekAss

Addibabeee Plays with herself while she rivulets

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

ShemaleSin

Crossdresser Willing to get Screwed Doggy Position

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Hawt Crossdresser Gets Drilled RAW
2 years ago
1:06

ShemaleSin

Hawt Crossdresser Gets Drilled RAW

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May in October
10 months ago
11:50

ShemaleSin

May in October

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1 year ago
8:39

ShemaleSin

Sissy upskirt twerk

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1 year ago
8:11

TrannyOne

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1 year ago
2:27

ShemaleSin

This Babe have pleasure with her weenie-beauty

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

ShemaleSin

Pink Juggsy in 44 R Cup Brassiere

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1 year ago
25:12

KeekAss

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

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

ShemaleSin

Oriental Sissy T-Girl Ladyboy Dancing and Showing her Body

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Listening to Feminization  Keismindwarp after Cumming from 2 Dildos at one time
2 years ago
0:39

ShemaleSin

Listening to Feminization  Keismindwarp after Cumming from 2 Dildos at one time

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

ShemaleSin

Girlfriend Makes boyfriend to Suit as a Woman for the Weekend

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Amy needs to get Drilled
3 years ago
5:36

ShemaleSin

Amy needs to get Drilled

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Crossdresser Feminized to get Screwed by Guy
2 years ago
0:33

ShemaleSin

Crossdresser Feminized to get Screwed by Guy

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

ShemaleSin

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

ShemaleSin

Crossdresser Willing to get Banged in Living Room

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Dec 8th 2022
1 year ago
10:05

ShemaleSin

Dec 8th 2022

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Sissy Feminization
2 years ago
14:04

TrannyOne

Sissy Feminization

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2 years ago
6:56

ShemaleSin

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

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Underware Wearing Trans Woman
2 years ago
1:12

ShemaleSin

Underware Wearing Trans Woman

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Feminisation @ Home
2 years ago
3:46

ShemaleSin

Feminisation @ Home

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Crossdresser Willing to get Screwed Raw
3 years ago
0:23

ShemaleSin

Crossdresser Willing to get Screwed Raw

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Sissy Bitch Deserves Humiliation and Public Exposure
1 year ago
9:50

PornHub

Sissy Bitch Deserves Humiliation and Public Exposure

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Crossdresser Expecting for Cum Discharged
2 years ago
0:59

ShemaleSin

Crossdresser Expecting for Cum Discharged

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Crossdressers Having Fun
2 years ago
2:19:39

TrannyOne

Crossdressers Having Fun

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Feminized Captions for Sissies
1 year ago
1:00

PornHub

Feminized Captions for Sissies

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2 years ago
5:06

ShemaleSin

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Tube Top & Denim Mask Doll
3 years ago
9:26

ShemaleSin

Tube Top & Denim Mask Doll

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Sexy Crossdresser Opens Legs
2 years ago
0:14

ShemaleSin

Sexy Crossdresser Opens Legs

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

ShemaleSin

Sissy Training female energy (english voice)

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1 year ago
0:23

ShemaleSin

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

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Sissy Fucks ass in panties
1 year ago
2:13

PornHub

Sissy Fucks ass in panties

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

ShemaleSin

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

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caged femboy soaks panties
1 year ago
1:31

PornHub

caged femboy soaks panties

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Mar 20th 2022
2 years ago
9:44

ShemaleSin

Mar 20th 2022

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1 year ago
4:11

ShemaleSin

Pegging my sissy bitch balls unfathomable

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2 years ago
4:29

ShemaleSin

Hot sissy girly dancing near couch in fantastic underware

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Hawt Golden-Haired Crossdresser Shows Rod
2 years ago
0:14

ShemaleSin

Hawt Golden-Haired Crossdresser Shows Rod

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Nov 25th 2022
1 year ago
0:40

ShemaleSin

Nov 25th 2022

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Sissy practices her fellatio technique
2 years ago
2:10

ShemaleSin

Sissy practices her fellatio technique

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

ShemaleSin

Girlfriend Makes Sissy Boyfriend to go on Date with Guy

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Feminized Tranny
2 years ago
20:07

TrannyOne

Feminized Tranny

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Cute Sissy Trap Femboy Butt Dancing
3 years ago
0:46

ShemaleSin

Cute Sissy Trap Femboy Butt Dancing

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BEST FEMDOM DOUBLE ANAL. THIS BITCH IS STRETCHED TO TWO COCKS. SISSY FEMDOM PEGGING
1 year ago
2:27

PornHub

BEST FEMDOM DOUBLE ANAL. THIS BITCH IS STRETCHED TO TWO COCKS. SISSY FEMDOM PEGGING

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Feminized and Spanked
2 years ago
5:29

TrannyOne

Feminized and Spanked

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femboy goes deeper into porn
2 years ago
0:39

ShemaleSin

femboy goes deeper into porn

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CocoTranse Ultimate Feminizer
2 years ago
31:04

TrannyOne

CocoTranse Ultimate Feminizer

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Sissy out in a miniskirt
1 year ago
5:20

ShemaleSin

Sissy out in a miniskirt

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Romina's Gyrations (lady mask, mask, fetish, trans, crossdress, transformation, stockings, stilettos)
1 year ago
13:36

KeekAss

Romina's Gyrations (lady mask, mask, fetish, trans, crossdress, transformation, stockings, stilettos)

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4 months ago
7:24

ShemaleSin

Bitch golden-haired trans sucking ebony dick at the beach

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

TrannyOne

femboy goes deeper into porn (crossdresser sissy trap)

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

ShemaleSin

Hawt Blond Trans Woman Willing to be Screwed

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Two Boys Crossdressing and Fucking
2 years ago
12:21

TrannyOne

Two Boys Crossdressing and Fucking

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Sissy Maid Public Outing
1 year ago
0:51

ShemaleSin

Sissy Maid Public Outing

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

ShemaleSin

Bisex Crossdressing And Femdom Dream Movie Scenes

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Masturbation with a fuck machine! Please look at my dirty anus..♡Japanese crossdresser Masturbatio
1 year ago
8:10

PornHub

Masturbation with a fuck machine! Please look at my dirty anus..♡Japanese crossdresser Masturbatio

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Trap80 with fuckmachine
1 year ago
5:24

KeekAss

Trap80 with fuckmachine

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

ShemaleSin

Sissy Transformation Ft Trans Femdom Queen

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

ShemaleSin

Sissy Bitch & BBC Ass Bumpin Magic

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Sissification feminization sissy training - Sissy husband story part 2 (english voice)
1 year ago
12:15

PornHub

Sissification feminization sissy training - Sissy husband story part 2 (english voice)

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PsychodelicSissy two
2 years ago
7:16

ShemaleSin

PsychodelicSissy two

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Apr 22nd 2023
1 year ago
17:29

ShemaleSin

Apr 22nd 2023

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

KeekAss

ARE YOU TRULY A STUD?? teaching feminization transgirl

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11 months ago
22:17

ShemaleSin

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1 year ago
0:14

ShemaleSin

Sissy shows off her vibrating buttplug

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1 year ago
17:02

TrannyOne

Sissy Giving Daddy Smoking Blowjob

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Soiree Doll Wants Pecker at the Pub
1 year ago
13:32

KeekAss

Soiree Doll Wants Pecker at the Pub

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2 years ago
1:27

ShemaleSin

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Sissy Cums with Castration Band on -Elastrator Play
11 months ago
3:46

PornHub

Sissy Cums with Castration Band on -Elastrator Play

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1 year ago
3:29

PornHub

Fist my ass!!

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1 year ago
36:51

ShemaleTaxi

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Sissy Widens her Gap with an Inflatable Sex-Toy
2 years ago
7:12

ShemaleSin

Sissy Widens her Gap with an Inflatable Sex-Toy

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Sissy teases rides and cums
2 years ago
1:40

ShemaleSin

Sissy teases rides and cums

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Sissy Blondie Screws her Butt with Buttplug in Pink Costume
2 years ago
1:04

ShemaleSin

Sissy Blondie Screws her Butt with Buttplug in Pink Costume

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Assignment from his Wife, Sissy Learns to Dance
3 years ago
2:18

ShemaleSin

Assignment from his Wife, Sissy Learns to Dance

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Femdom Gone Wild: Pegging a Bitch Crossdresser #BratPerversions
1 year ago
0:25

ShemaleSin

Femdom Gone Wild: Pegging a Bitch Crossdresser #BratPerversions

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

ShemaleSin

Dom CD Shemale Drag Queen Feminization Mastix become my Sissy Wench

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CD Mask Film Noir
3 years ago
3:36

ShemaleSin

CD Mask Film Noir

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Crossdresser getting Willing to get Banged
2 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)
3 years ago
3:43

ShemaleSin

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

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

ShemaleSin

POV Hot Golden-Haired Crossdresser Sucking Shlong

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J3ss1c4 F4pp1t - Feminization is Permanent
3 years ago
8:14

ShemaleSin

J3ss1c4 F4pp1t - Feminization is Permanent

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Lewd Golden-Haired Crossdresser Showing Off Outfit
2 years ago
0:39

ShemaleSin

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8 years ago
6:00

aShemaleTube

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2 years ago
13:36

ShemaleSin

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2 years ago
4:01

ShemaleSin

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2 years ago
1:36

ShemaleSin

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2 years ago
0:20

ShemaleSin

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3 years ago
0:23

ShemaleSin

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9 months ago
5:16

ShemaleSin

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2 years ago
3:21

TrannyOne

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2 years ago
3:12

ShemaleSin

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2 years ago
0:18

ShemaleSin

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1 year ago
3:18

PornHub

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1 year ago
2:06

ShemaleSin

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1 year ago
4:25

PornHub

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2 years ago
10:01

ShemaleSin

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5 months ago
0:16

ShemaleSin

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3 years ago
8:11

ShemaleSin

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2 years ago
1:11

ShemaleSin

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1 year ago
11:29

PornHub

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1 year ago
1:54

ShemaleSin

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2 years ago
0:43

ShemaleSin

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2 years ago
2:46

ShemaleSin

Sissy Twerks her Butt in Oil

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3 years ago
6:48

ShemaleSin

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2 years ago
1:28

ShemaleSin

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1 year ago
5:42

KeekAss

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2 years ago
10:24

KeekAss

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1 year ago
0:31

xHamster

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2 years ago
0:37

PornHub

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2 years ago
24:18

ShemaleZ

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4 years ago
14:32

ShemaleZ

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2 years ago
0:25

PornHub

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2 years ago
31:52

KeekAss

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1 year ago
23:23

KeekAss

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2 years ago
6:18

PornHub

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4 years ago
4:59

KeekAss

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2 years ago
7:24

ShemaleTaxi

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3 years ago
10:06

KeekAss

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Sissy Transformation: Cock Worship for Sissy ft Trans Femdom Queen
2 years ago
1:00

PornHub

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Astounding Sissy Trainer - SissyHypnoz
4 years ago
8:13

KeekAss

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2 years ago
5:13

ShemaleTaxi

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3 years ago
5:12

ShemaleTaxi

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2 years ago
1:41

PornHub

Sissy's Femdom Sex Training

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1 year ago
18:32

PornHub

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8 years ago
3:07

aShemaleTube

Feminization

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2 years ago
2:48

PornHub

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3 years ago
13:26

PornHub

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1 year ago
25:29

KeekAss

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3 years ago
4:38

PornHub

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3 years ago
7:21

ShemaleTaxi

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4 years ago
6:19

ShemaleMovie

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3 years ago
0:20

PornHub

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Girls Club Episode 3: A Sissy Feminization Series
5 years ago
33:04

ShemaleZ

Girls Club Episode 3: A Sissy Feminization Series

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Sissy Crossdresser Annon Blowjob Training
4 years ago
2:15

PornHub

Sissy Crossdresser Annon Blowjob Training

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