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

KeekAss

*Trailer* Sissy Teaching Basics With Kelli Frost

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3 years ago
8:37

aShemaleTube

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3 years ago
47:30

TrannyOne

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V-Card Box and Spandex Tights! 201702
3 years ago
21:20

KeekAss

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3 years ago
15:11

aShemaleTube

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4 years ago
0:51

aShemaleTube

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4 years ago
34:15

TrannyOne

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Sissy in Chastity Rides BBC Dildo
4 years ago
1:20

aShemaleTube

Sissy in Chastity Rides BBC Dildo

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Chastity With Fucking Machine 1
4 years ago
19:00

aShemaleTube

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4 years ago
9:54

KeekAss

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Female Dominance Smacks and Cages 2 TRANSSEXUAL Subjugated Sissy Supersluts
4 years ago
13:27

KeekAss

Female Dominance Smacks and Cages 2 TRANSSEXUAL Subjugated Sissy Supersluts

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Sissy Valerie Part 1
5 years ago
8:49

KeekAss

Sissy Valerie Part 1

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5 years ago
1:32

KeekAss

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Purity Contraption with Donk Speculum Attachment
5 years ago
5:57

KeekAss

Purity Contraption with Donk Speculum Attachment

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Trine Larsen 2025 The tour Black in the back
7 days ago
9:21

aShemaleTube

Trine Larsen 2025 The tour Black in the back

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Sissy in V-card Humped with Fuckmachine
12 days ago
13:25

KeekAss

Sissy in V-card Humped with Fuckmachine

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Selenay Chastity Cage Sissygasm Ride Dildo Anal Masturbation
17 days ago
3:36

aShemaleTube

Selenay Chastity Cage Sissygasm Ride Dildo Anal Masturbation

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Leash And Laurens Domination - Crystal Thayer, Anal Toys And Tony Orlando
30 days ago
11:30

ShemaleZ

Leash And Laurens Domination - Crystal Thayer, Anal Toys And Tony Orlando

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What Do Girls Do - PMV by HoloPMV
39 days ago
2:57

aShemaleTube

What Do Girls Do - PMV by HoloPMV

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Ginormous Fake penis - Good-sized Jizz shot Deep Rectal Instructing Sissy Jessica Bloom
48 days ago
7:28

KeekAss

Ginormous Fake penis - Good-sized Jizz shot Deep Rectal Instructing Sissy Jessica Bloom

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54 days ago
1:44

aShemaleTube

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C ☢SexXRouLette and Chastity Cage on the Balcony. Ejacul 4min35 [¹aou²] VaneSsaBiTCHx
57 days ago
16:56

aShemaleTube

C ☢SexXRouLette and Chastity Cage on the Balcony. Ejacul 4min35 [¹aou²] VaneSsaBiTCHx

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59 days ago
16:08

aShemaleTube

Sissy coming home from work

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Big Black Cock leaves Shemale no chances not to cum
2 months ago
11:14

MyLust

Big Black Cock leaves Shemale no chances not to cum

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Italian CD Daniela caged solo compilation
2 months ago
9:26

aShemaleTube

Italian CD Daniela caged solo compilation

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3 months ago
4:47

aShemaleTube

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Rachael Belle Exposed Chastity Sissy Slut Humiliation 1-6 Compilation
3 months ago
13:19

aShemaleTube

Rachael Belle Exposed Chastity Sissy Slut Humiliation 1-6 Compilation

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Sissy Clitty Handjob
3 months ago
1:00

aShemaleTube

Sissy Clitty Handjob

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6 years ago
3:56

ShemaleZ

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4 months ago
1:00

aShemaleTube

BBC beating them hot TS guts

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6 months ago
2:09

aShemaleTube

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6 months ago
11:43

HDSex

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French teen transsexual gets dominated and teased while in a chastity cage by Actorfab
6 months ago
11:41

VideoSection

French teen transsexual gets dominated and teased while in a chastity cage by Actorfab

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7 months ago
8:54

KeekAss

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Trap with her faux-cocks
8 months ago
29:02

KeekAss

Trap with her faux-cocks

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Big Black ripping my ass -Hotel pt 3
8 months ago
6:04

aShemaleTube

Big Black ripping my ass -Hotel pt 3

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Sissy innocence box hard-core anal invasion playplay
9 months ago
2:42

KeekAss

Sissy innocence box hard-core anal invasion playplay

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Mana Kali got caged
10 months ago
1:16:11

aShemaleTube

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Kitty Pin Regular V2 - Fitting Guide. Clothespins and ropes available from emmasplace.online
10 months ago
3:07

KeekAss

Kitty Pin Regular V2 - Fitting Guide. Clothespins and ropes available from emmasplace.online

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Large Arse Sissy Fuckslut Tag Teamed By Faux-cocks for Torrid Rectal Summer
11 months ago
7:04

KeekAss

Large Arse Sissy Fuckslut Tag Teamed By Faux-cocks for Torrid Rectal Summer

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Cage fight
11 months ago
1:35

aShemaleTube

Cage fight

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1 year ago
6:49

VideoSection

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Percent Sissy Taunting
1 year ago
7:13

KeekAss

Percent Sissy Taunting

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Sissy squirting in chastity cage
1 year ago
19:51

aShemaleTube

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two TRANSSEXUAL Beefsticks Packs Da Taut Cage Of Perverted COUGAR Dee Williams!
1 year ago
12:16

KeekAss

two TRANSSEXUAL Beefsticks Packs Da Taut Cage Of Perverted COUGAR Dee Williams!

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1 year ago
6:26

aShemaleTube

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1 year ago
10:43

aShemaleTube

Cumming in chastity

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Sissy cums in the cage
1 year ago
6:34

XXXDan

Sissy cums in the cage

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Tranny Babe in Chasity Cage Gets Fucked by large Dildo
1 year ago
11:37

XXXDan

Tranny Babe in Chasity Cage Gets Fucked by large Dildo

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Dani in chastity
1 year ago
10:11

aShemaleTube

Dani in chastity

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Sissy in chastity cage masturbates with vibrator
1 year ago
6:58

XXXDan

Sissy in chastity cage masturbates with vibrator

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TS Mariaqt chastity fuck machine cum
1 year ago
7:26

aShemaleTube

TS Mariaqt chastity fuck machine cum

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femboy trap Charlene beats own balls...
1 year ago
9:55

aShemaleTube

femboy trap Charlene beats own balls...

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White Lingerie Rina Teasing & Release
1 year ago
7:23

aShemaleTube

White Lingerie Rina Teasing & Release

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Sissy pansy Andreina
1 year ago
4:15

aShemaleTube

Sissy pansy Andreina

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Audrey tgirl: real public prostitute in a chastity cage
1 year ago
5:13

XXXDan

Audrey tgirl: real public prostitute in a chastity cage

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First time Sissy MixyXXX training FIST with hands free orgasm!
1 year ago
23:03

aShemaleTube

First time Sissy MixyXXX training FIST with hands free orgasm!

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1 year ago
7:39

aShemaleTube

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1 year ago
4:18

aShemaleTube

Tranny fucks her ass with big dildo

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Sissy Anal cuming
1 year ago
4:53

aShemaleTube

Sissy Anal cuming

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sissy whore TS-Nutzgirly90 play with dildo
2 years ago
6:38

aShemaleTube

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Practising How I Will Need to Wank for All of Locktober
2 years ago
2:08

KeekAss

Practising How I Will Need to Wank for All of Locktober

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2 years ago
7:04

KeekAss

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2 years ago
3:30

KeekAss

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Heels chastity and a happy ending
2 years ago
11:32

aShemaleTube

Heels chastity and a happy ending

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Innocence Cell Sissy walk thru the Arboretum
2 years ago
3:09

KeekAss

Innocence Cell Sissy walk thru the Arboretum

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sissyish stephanie caged
3 years ago
0:35

aShemaleTube

sissyish stephanie caged

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smok in chastity 2
2 years ago
6:47

aShemaleTube

smok in chastity 2

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Natilie Mars's Mistress 2
2 years ago
18:18

TrannyOne

Natilie Mars's Mistress 2

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New gurl Missy fucked in chastity at The Sissy Institute
2 years ago
3:54

TrannyOne

New gurl Missy fucked in chastity at The Sissy Institute

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Ashtray Pig - Rough Pegging for Miss Piggy
2 years ago
3:10

aShemaleTube

Ashtray Pig - Rough Pegging for Miss Piggy

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Sissy slut sucks and lets master fuck her
2 years ago
6:03

TrannyOne

Sissy slut sucks and lets master fuck her

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Sissy victim Oksana showcases urinate, cucumber and orange flash in vid talk with her Sir
2 years ago
8:04

KeekAss

Sissy victim Oksana showcases urinate, cucumber and orange flash in vid talk with her Sir

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sissy tania training her ass
2 years ago
6:12

aShemaleTube

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Quarantine Joy With Sofia Ass-Cheek , Nyxi Leon, and Lix Kyo
3 years ago
8:07

KeekAss

Quarantine Joy With Sofia Ass-Cheek , Nyxi Leon, and Lix Kyo

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3 years ago
7:17

aShemaleTube

small dick cum in chastity

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3 years ago
7:00

KeekAss

transsexual uncaged for condom-free romp and facial cumshot

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Chastity Sissy Fag
3 years ago
0:36

aShemaleTube

Chastity Sissy Fag

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Amateur Punishment
3 years ago
2:06

TrannyOne

Amateur Punishment

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Sissy Oksana jizzes highly amply during assfuck fake penis teaching
3 years ago
13:54

KeekAss

Sissy Oksana jizzes highly amply during assfuck fake penis teaching

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Fucking Machine fucking the sissy pig ass cunt
3 years ago
8:56

TrannyOne

Fucking Machine fucking the sissy pig ass cunt

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Sissy MJ's Purity Juggles While She Rails Parent's Xxl Man Meat
3 years ago
3:58

KeekAss

Sissy MJ's Purity Juggles While She Rails Parent's Xxl Man Meat

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woman with clitty caged in Victoria Secret fitting room
3 years ago
9:09

TrannyOne

woman with clitty caged in Victoria Secret fitting room

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Palms off Contest - Day 27
4 years ago
21:36

KeekAss

Palms off Contest - Day 27

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Sissy Lucy spitroast in chastity by double fucking machines
4 years ago
2:11

aShemaleTube

Sissy Lucy spitroast in chastity by double fucking machines

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Spraying Lovely femboy whit chasty in the manstick and rail her fuck stick
4 years ago
10:02

KeekAss

Spraying Lovely femboy whit chasty in the manstick and rail her fuck stick

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My First Time Cumming in Chastity Cage
4 years ago
1:03

aShemaleTube

My First Time Cumming in Chastity Cage

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SMALLISH TEENAGER SISSY CROSSDRESSER IN CHASITY BELT HANDSFREE EJACULATION
4 years ago
6:35

KeekAss

SMALLISH TEENAGER SISSY CROSSDRESSER IN CHASITY BELT HANDSFREE EJACULATION

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Sissy Screws herself to Handsfree Sissygasm in V-Card Box
4 years ago
5:05

KeekAss

Sissy Screws herself to Handsfree Sissygasm in V-Card Box

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Invasion HERMAPHRODITISM Look (Futa x Masculine)
5 years ago
1:57

KeekAss

Invasion HERMAPHRODITISM Look (Futa x Masculine)

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Femboy Enjoy II
5 years ago
19:43

KeekAss

Femboy Enjoy II

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Hot compilation featuring amazing Alexandra Braces Star
8 days ago
5:13

aShemaleTube

Hot compilation featuring amazing Alexandra Braces Star

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How I've made my boyfriend into a anal slut
12 days ago
4:38

aShemaleTube

How I've made my boyfriend into a anal slut

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shemale beautiful
22 days ago
11:26

aShemaleTube

shemale beautiful

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Fast hard pounding, remote control
32 days ago
17:06

VideoSection

Fast hard pounding, remote control

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Amy - Sissy Splitscreen Chastity Masturbation Compilation 4 Voice Over
39 days ago
13:34

aShemaleTube

Amy - Sissy Splitscreen Chastity Masturbation Compilation 4 Voice Over

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Caged, gaped &  prolapse pussy and covered in cum
48 days ago
1:08:50

aShemaleTube

Caged, gaped & prolapse pussy and covered in cum

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Caged, cum shot
54 days ago
21:45

VideoSection

Caged, cum shot

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Dp atm caged sissygasm & analgasm and piss prt 1
58 days ago
19:24

aShemaleTube

Dp atm caged sissygasm & analgasm and piss prt 1

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Masterbating like a sissy slut should. New flat cage
2 months ago
4:46

aShemaleTube

Masterbating like a sissy slut should. New flat cage

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Watching sissy porn in my new flat cage and cumming and squirting
3 months ago
8:55

aShemaleTube

Watching sissy porn in my new flat cage and cumming and squirting

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3 months ago
21:37

aShemaleTube

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Sissy taniax riding huge dildo
3 months ago
2:29

aShemaleTube

Sissy taniax riding huge dildo

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Anal adventures with trans queen Allywhorefrost in her sexy outfit and chastity cage
3 months ago
20:10

ShemaleMovie

Anal adventures with trans queen Allywhorefrost in her sexy outfit and chastity cage

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Lisa Controls My Electro Stim Chastity Cage And Dildo Fucks My Ass
4 years ago
14:36

ShemaleZ

Lisa Controls My Electro Stim Chastity Cage And Dildo Fucks My Ass

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Hot TS in Chasity taking bbc on her back
4 months ago
1:05

aShemaleTube

Hot TS in Chasity taking bbc on her back

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Daddy Fucks Cute Skinny Tgirl
5 months ago
4:01

PornGem

Daddy Fucks Cute Skinny Tgirl

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Chastity cage, oral job
6 months ago
6:57

ShemaleMovie

Chastity cage, oral job

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Sissy Pussy - PMV by PrimeBBC
6 months ago
2:57

aShemaleTube

Sissy Pussy - PMV by PrimeBBC

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Sissy Addict - PMV by HoloPMV
7 months ago
2:00

aShemaleTube

Sissy Addict - PMV by HoloPMV

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Baiser sonny cul de trans jusqu’à ce que sa box de chasteté coule!
7 months ago
4:34

KeekAss

Baiser sonny cul de trans jusqu’à ce que sa box de chasteté coule!

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Submissive ladyboy screwed by kinky dude
7 months ago
6:26

AnalDin

Submissive ladyboy screwed by kinky dude

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Sissy learns how to cum
8 months ago
13:24

aShemaleTube

Sissy learns how to cum

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Insatiable femboy shoots a load in a vapid innocence cell and keeps railing
8 months ago
6:46

KeekAss

Insatiable femboy shoots a load in a vapid innocence cell and keeps railing

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2025 First Hotel visit pt 2
8 months ago
5:17

aShemaleTube

2025 First Hotel visit pt 2

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Rosy maid in v-card rails fake penis
9 months ago
12:09

KeekAss

Rosy maid in v-card rails fake penis

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Warm sissy in black underwear railing fake penis
9 months ago
2:12

KeekAss

Warm sissy in black underwear railing fake penis

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two,600+ Plaps (For the Devotees~)
10 months ago
27:29

KeekAss

two,600+ Plaps (For the Devotees~)

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Sissy Maid Cums  Squirts Hard from Anal Fucking Machine in Chastity Cage - Jessica Bloom
10 months ago
7:25

XXXDan

Sissy Maid Cums Squirts Hard from Anal Fucking Machine in Chastity Cage - Jessica Bloom

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Teen ladyboy Bird Annie locked in a cage pleasuring herself
11 months ago
5:25

ShemaleMovie

Teen ladyboy Bird Annie locked in a cage pleasuring herself

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