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14 days ago
9:06

TrannyOne

Big cock makes sissy slut Bess cum twice

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Sissy Feminization and Fucked
44 days ago
3:31

xHamster

Sissy Feminization and Fucked

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2 years ago
5:36

TrannyOne

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1 year ago
5:28

PornHub

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1 year ago
0:33

PornHub

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7 years ago
7:42

xHamster

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8 years ago
6:00

aShemaleTube

Crossdresser Feminization by Dominatrix

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Glamorous Getaways: Crossdressing Adventures Around the World!
49 days ago
5:50

xHamster

Glamorous Getaways: Crossdressing Adventures Around the World!

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7 years ago
40:23

aShemaleTube

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Girls Who Like Femboys: Connecting with Like-Minded Souls
26 days ago
5:28

xHamster

Girls Who Like Femboys: Connecting with Like-Minded Souls

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7 years ago
1:54

aShemaleTube

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56 days ago
3:08

xHamster

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Feminization and Strapon Sex
8 years ago
21:53

aShemaleTube

Feminization and Strapon Sex

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Feminization- Guy Becomes Menina
8 years ago
4:47

aShemaleTube

Feminization- Guy Becomes Menina

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7 years ago
2:54

xHamster

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28 days ago
2:00

xHamster

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7 years ago
3:28

xHamster

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Sissy Compilation - Crosdfressers and Feminization
12 years ago
3:08

aShemaleTube

Sissy Compilation - Crosdfressers and Feminization

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8 years ago
6:00

aShemaleTube

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8 years ago
6:00

TnaFlix

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Sizzling Seduction: Unleashing My Inner Goddess
15 days ago
5:32

xHamster

Sizzling Seduction: Unleashing My Inner Goddess

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Man Feminized by Roommate as Discipline
27 days ago
10:41

xHamster

Man Feminized by Roommate as Discipline

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9 months ago
2:13

PornHub

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2 years ago
1:57

PornHub

Look At My Ass w/ Hot TS Julee Love

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Sissy Bella Gagged and Cumming from CBT
2 years ago
5:51

PornHub

Sissy Bella Gagged and Cumming from CBT

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Beautiful Sissy Secretary Talking Dirty and Stroking (preview)
11 months ago
2:05

xHamster

Beautiful Sissy Secretary Talking Dirty and Stroking (preview)

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10 months ago
2:15

xHamster

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1 year ago
3:01

KeekAss

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1 year ago
11:40

KeekAss

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Sissy has a Cagegasm
2 days ago
1:18

PornHub

Sissy has a Cagegasm

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Crossdresser She-Male Restrain Bondage Joy
1 year ago
9:39

KeekAss

Crossdresser She-Male Restrain Bondage Joy

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1 year ago
5:59

PornHub

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1 year ago
5:23

PornHub

TS W I L L O W - Sissy Clitty Squirts To BNWO PMV's

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1 year ago
4:14

PornHub

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11 months ago
4:19

PornHub

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10 months ago
0:21

PornHub

Eat My Ass Faggot ft Trans Femdom

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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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Juggsy Female Masker Z Cup Stripper
6 months ago
10:04

PornHub

Juggsy Female Masker Z Cup Stripper

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Sissy Hope, the slut being controlled by Master on videocall
4 months ago
17:43

xHamster

Sissy Hope, the slut being controlled by Master on videocall

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VERY HOT Goth Sissy Sucking Cock POV
14 days ago
5:43

TrannyOne

VERY HOT Goth Sissy Sucking Cock POV

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Young Boy becomes a Beautiful Sissy
5 months ago
5:42

xHamster

Young Boy becomes a Beautiful Sissy

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Trans Jessica Moon Rides Crossdresser Bailey Wilde's Cock
2 months ago
8:54

xHamster

Trans Jessica Moon Rides Crossdresser Bailey Wilde's Cock

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Sissy Blowjob Training To Be Fucked
27 days ago
2:17

xHamster

Sissy Blowjob Training To Be Fucked

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Grieving MOURNING WOOD Consoled by Faggyboi
36 days ago
3:52

xHamster

Grieving MOURNING WOOD Consoled by Faggyboi

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Tight Sissy Pegged While Gagged in Cuffs on Bench with Huge Bad Dragon Strapon by Mistress Mercer
1 year ago
2:53

PornHub

Tight Sissy Pegged While Gagged in Cuffs on Bench with Huge Bad Dragon Strapon by Mistress Mercer

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I Cumming From Hard Strap on Fuck
7 months ago
1:00

xHamster

I Cumming From Hard Strap on Fuck

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4 months ago
18:03

KeekAss

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Love for Webcam Modeling: Expressing Confidence and Sensuality
23 days ago
5:19

xHamster

Love for Webcam Modeling: Expressing Confidence and Sensuality

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Crossdresser Sissy roped and ball-gagged
1 year ago
6:14

KeekAss

Crossdresser Sissy roped and ball-gagged

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Sissy Dani riding in chastity
3 months ago
1:19

xHamster

Sissy Dani riding in chastity

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7 months ago
3:38

PornHub

Sissy showing off

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Fashion Inspiration: Celebrity Looks to Love
58 days ago
5:16

xHamster

Fashion Inspiration: Celebrity Looks to Love

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Sissy tried tucking and going for a walk
7 months ago
5:44

PornHub

Sissy tried tucking and going for a walk

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Juggsy Woman Masker Z Bowl Stripper #2
6 months ago
7:53

KeekAss

Juggsy Woman Masker Z Bowl Stripper #2

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9 months ago
1:00

PornHub

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9 months ago
2:12

PornHub

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5 months ago
11:55

KeekAss

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Sissyslut Naya jerks off and cums in her mouth
2 months ago
0:28

xHamster

Sissyslut Naya jerks off and cums in her mouth

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How a Sissy should Masturbate - Sissy - Crossdresser slut - Chastity with Vibrator - Sissy Joanna
5 months ago
6:55

xHamster

How a Sissy should Masturbate - Sissy - Crossdresser slut - Chastity with Vibrator - Sissy Joanna

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VERY HOT Blonde Crossdresser in Pink Chastity Fucked
39 days ago
7:14

xHamster

VERY HOT Blonde Crossdresser in Pink Chastity Fucked

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11 months ago
5:20

KeekAss

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Sissy Cumming Wearing His Mommys Black Panties
5 months ago
6:16

xHamster

Sissy Cumming Wearing His Mommys Black Panties

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Dominatrix Strapon Fucked Crossdresser in Chastity
6 months ago
2:55

xHamster

Dominatrix Strapon Fucked Crossdresser in Chastity

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Goth Femboy Jade Madison Fucked Against Wall
15 days ago
2:46

xHamster

Goth Femboy Jade Madison Fucked Against Wall

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Sissy Training
8 months ago
5:02

PornHub

Sissy Training

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Prettyful Trans Sissy Biotch In Rosy Undergarments Gets Bitchy
4 months ago
9:20

KeekAss

Prettyful Trans Sissy Biotch In Rosy Undergarments Gets Bitchy

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Crossdressing Beauty Secrets: Tips and Tricks for a Flawless Look!
21 days ago
5:55

xHamster

Crossdressing Beauty Secrets: Tips and Tricks for a Flawless Look!

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RubyMabel (Stella Foxxx) uses 16in. long 3in. wide dildo on her ass
7 months ago
3:21

PornHub

RubyMabel (Stella Foxxx) uses 16in. long 3in. wide dildo on her ass

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Sissy Slut Ejaculates After Morning Wakeup Cum Show at Country House
8 days ago
45:30

xHamster

Sissy Slut Ejaculates After Morning Wakeup Cum Show at Country House

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7 months ago
4:13

PornHub

Locked up trans girl pissing and cumming on herself

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Crossdresser Self Restrain Bondage Cam display
1 year ago
12:33

KeekAss

Crossdresser Self Restrain Bondage Cam display

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Slutty Sissy Pirate Cage Dance by Sissy Mindy
48 days ago
5:34

xHamster

Slutty Sissy Pirate Cage Dance by Sissy Mindy

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1 year ago
19:49

KeekAss

Sissy in high high-heeled shoes jizz from ass-fuck only! Immense sissygasm!!!

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Pale White Blonde Sissy Desperately Trying to Seduce Men
3 months ago
6:28

xHamster

Pale White Blonde Sissy Desperately Trying to Seduce Men

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Trans girl caresses dick and cums in panties
7 months ago
5:05

PornHub

Trans girl caresses dick and cums in panties

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9 months ago
7:03

KeekAss

SisK undergarments bevy EP15.two Stroking with crimson netting stockings

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6 months ago
7:05

xHamster

Sexy CD get fuck on sofa with her transparent nightie

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2 months ago
1:28:33

xHamster

Long fucking machine session with multiple large toys

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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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6 months ago
8:52

xHamster

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TS Kelsey Masters and TS Bailey Wilde Masturbation
4 months ago
11:21

xHamster

TS Kelsey Masters and TS Bailey Wilde Masturbation

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10 months ago
3:03

PornHub

Fill my Sissy Hole With Cum

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Colorful Videos: Showcasing Cute Body and Sexy Dresses
29 days ago
6:10

xHamster

Colorful Videos: Showcasing Cute Body and Sexy Dresses

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2 months ago
0:21

xHamster

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Kitty's Cute Creations: Craft Adorable and Heartwarming Videos that Melt Hearts and Spread Joy, as You Capture the Playfulness
3 months ago
5:27

xHamster

Kitty's Cute Creations: Craft Adorable and Heartwarming Videos that Melt Hearts and Spread Joy, as You Capture the Playfulness

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Full Feminization and Tucking Teen Sissy Crossdresser
4 months ago
2:15

xHamster

Full Feminization and Tucking Teen Sissy Crossdresser

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Super Hot Crossdresser Bailey Wilde Jerking Off and Cums
2 months ago
15:19

xHamster

Super Hot Crossdresser Bailey Wilde Jerking Off and Cums

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TS W I L L O W - Girl Dick & Cum PMV
10 months ago
2:53

PornHub

TS W I L L O W - Girl Dick & Cum PMV

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8 months ago
1:32

PornHub

CD suck big black cock (bbc)

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

xHamster

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

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1 year ago
10:52

KeekAss

Trans nymph very first movie since transitioning

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Feminization Sissification Sissy training - BE SUBMISSIVE FAG
11 months ago
24:44

PornHub

Feminization Sissification Sissy training - BE SUBMISSIVE FAG

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Steamy Secrets: Behind Closed Doors
15 days ago
5:57

xHamster

Steamy Secrets: Behind Closed Doors

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My first live with a QOS tattoo
51 days ago
20:05

xHamster

My first live with a QOS tattoo

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Sissy Feminized - How it Started & where I am now.
3 months ago
3:13

xHamster

Sissy Feminized - How it Started & where I am now.

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SISSY tries FUCKMACHINE for the FIRST TIME
1 year ago
1:22

PornHub

SISSY tries FUCKMACHINE for the FIRST TIME

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Sexy Crossdresser Jerking Off in Las Vegas
4 months ago
5:13

xHamster

Sexy Crossdresser Jerking Off in Las Vegas

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6 months ago
5:14

xHamster

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Blonde Crossdresser get fucked by dildo
2 months ago
2:52

xHamster

Blonde Crossdresser get fucked by dildo

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4 months ago
6:19

KeekAss

Peeing man dressed in a plane purity box with catheter and sans that one

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Sissy Whore Cindy
3 months ago
7:00

xHamster

Sissy Whore Cindy

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MistyBubbleWush's Guide to Sissy Training (2024)
2 months ago
1:27

xHamster

MistyBubbleWush's Guide to Sissy Training (2024)

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Sissy Reverse Cowgirl Rides Huge Strapon
39 days ago
4:39

xHamster

Sissy Reverse Cowgirl Rides Huge Strapon

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Shameless Sissy Supergirl Jerks Off on Snapchat.
3 months ago
5:15

xHamster

Shameless Sissy Supergirl Jerks Off on Snapchat.

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Fashionable Traveler: Jet-Setting in Style
15 days ago
5:41

xHamster

Fashionable Traveler: Jet-Setting in Style

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Small Sissy Cock Critted
17 days ago
4:43

xHamster

Small Sissy Cock Critted

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Sophie Krens bound up and deepthroat fake penis
10 months ago
2:02

KeekAss

Sophie Krens bound up and deepthroat fake penis

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Dominatrix Makes Feminized Roommate Wear Corset
6 months ago
2:55

xHamster

Dominatrix Makes Feminized Roommate Wear Corset

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Phat Ass Sissy LadyBoy Cross Dresser Caught!
54 days ago
6:06

xHamster

Phat Ass Sissy LadyBoy Cross Dresser Caught!

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Riding the Large Dryder that's 9.1'' around from The Wandering Bard. Platinum silicon dildo.
9 months ago
5:54

PornHub

Riding the Large Dryder that's 9.1'' around from The Wandering Bard. Platinum silicon dildo.

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1 year ago
10:51

PornHub

オナニーが気持ち良すぎてオシッコ出ちゃった♡Masturbation is too comfortable Pee peeing,,,♡ japanese crossdresserオナニー

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Love for Nature: Embracing the Beauty of the Outdoors
25 days ago
5:22

xHamster

Love for Nature: Embracing the Beauty of the Outdoors

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Sissy Trap fucks her boipussy with a big dildo
4 months ago
5:20

xHamster

Sissy Trap fucks her boipussy with a big dildo

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Trans Cat Girl Maid Dress and Cumshot
10 months ago
5:22

PornHub

Trans Cat Girl Maid Dress and Cumshot

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Tsgirl Hijab Maid Cosplay Anal Masturbation
20 days ago
5:07

xHamster

Tsgirl Hijab Maid Cosplay Anal Masturbation

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Sissy stretches her ass for your dick!
9 months ago
3:06

PornHub

Sissy stretches her ass for your dick!

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BE MY PANTY BOY (teaser)
1 year ago
0:32

PornHub

BE MY PANTY BOY (teaser)

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Sissygasm in Chastity
2 months ago
0:34

xHamster

Sissygasm in Chastity

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Ballgag harness selfbondage
7 months ago
1:17

PornHub

Ballgag harness selfbondage

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Chastity gets Vibrated Her Clitty Projectile Squirt Cummies, her tiny balls SPANKED, & Turning the Fuck Machine Up to its Max!
4 months ago
6:20

xHamster

Chastity gets Vibrated Her Clitty Projectile Squirt Cummies, her tiny balls SPANKED, & Turning the Fuck Machine Up to its Max!

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