Sissy: 1742 Videos

Sissy SLut Cumming so Hard
3 years ago
1:12

PornHub

Sissy SLut Cumming so Hard

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sissy babypansy's diapering status
7 years ago
1:12

xHamster

sissy babypansy's diapering status

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Sissy outdoor
28 days ago
1:11

xHamster

Sissy outdoor

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How a Sissy Masturbates and Cums - Sissygasms ONLY for you! Sissy Training with Goddess Nikki Kit
3 years ago
1:10

PornHub

How a Sissy Masturbates and Cums - Sissygasms ONLY for you! Sissy Training with Goddess Nikki Kit

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Sissy fingering her boipussy ready
5 years ago
1:10

PornHub

Sissy fingering her boipussy ready

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sissy doris fun with toy
4 years ago
1:07

PornHub

sissy doris fun with toy

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Sissy Rides Dildo to Peegasm
4 years ago
1:07

xHamster

Sissy Rides Dildo to Peegasm

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Sissy femboy fucks herself from the side Anal Dildo Play
3 years ago
1:05

PornHub

Sissy femboy fucks herself from the side Anal Dildo Play

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Sissy slut pee while fucking her ass with dildo
3 years ago
1:05

PornHub

Sissy slut pee while fucking her ass with dildo

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Cuckolding my BBC Loving Sissy Husband
4 years ago
1:04

PornHub

Cuckolding my BBC Loving Sissy Husband

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Sissy Slut Ellie Self Facial
5 years ago
1:04

xHamster

Sissy Slut Ellie Self Facial

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Detroit Twiinkee the Sissy cumshot
4 years ago
1:03

PornHub

Detroit Twiinkee the Sissy cumshot

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Sissy Tied Up And Plowed By Hankey's XXL Lampwick Uncut
3 years ago
1:02

PornHub

Sissy Tied Up And Plowed By Hankey's XXL Lampwick Uncut

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Panty sissy masturbates and cums on himself.
7 years ago
1:02

xHamster

Panty sissy masturbates and cums on himself.

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Trans sissy girl Karly Fucks Black dildo
5 years ago
1:02

xHamster

Trans sissy girl Karly Fucks Black dildo

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Babbel Mann & Sissy Part 3 Kaiserslautern
5 years ago
1:02

xHamster

Babbel Mann & Sissy Part 3 Kaiserslautern

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Femboy many and wet cums with pleasure ( hot sissy slut crossdress )
4 years ago
1:02

PornHub

Femboy many and wet cums with pleasure ( hot sissy slut crossdress )

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Sissy CD Rides BBC
7 years ago
1:01

xHamster

Sissy CD Rides BBC

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Sissy Anal toy tease
3 years ago
1:01

PornHub

Sissy Anal toy tease

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sissy's day
4 years ago
1:01

xHamster

sissy's day

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sissy faggot fucks
7 years ago
1:00

xHamster

sissy faggot fucks

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Sissy Slut Anal Cum
3 years ago
1:00

PornHub

Sissy Slut Anal Cum

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Sissy Training Therapy Session - Feminized by New Therapist by Gentle FemDom Goddess Nikki Kit PRV
3 years ago
1:00

PornHub

Sissy Training Therapy Session - Feminized by New Therapist by Gentle FemDom Goddess Nikki Kit PRV

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Sexy Blonde Sissy Girl Trap Trans Showing Off Lingerie
3 years ago
0:59

PornHub

Sexy Blonde Sissy Girl Trap Trans Showing Off Lingerie

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Sexy Sissy Slut Trap Trans Blonde Girl Fucks Her Ass Hot Anal
4 years ago
0:59

PornHub

Sexy Sissy Slut Trap Trans Blonde Girl Fucks Her Ass Hot Anal

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Sissy Blonde Trans Girl Fucks Her Ass Glass Dildo In Lingerie
4 years ago
0:59

PornHub

Sissy Blonde Trans Girl Fucks Her Ass Glass Dildo In Lingerie

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Sexy Shemale Sissy Girl Fucks Her Ass Upskirt Lingerie
4 years ago
0:59

PornHub

Sexy Shemale Sissy Girl Fucks Her Ass Upskirt Lingerie

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Sexy Sissy Pink Lingerie Fucks Her Asshole Slut
4 years ago
0:59

PornHub

Sexy Sissy Pink Lingerie Fucks Her Asshole Slut

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cocksucking sissy slut
13 years ago
0:57

xHamster

cocksucking sissy slut

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big dildo crossdresser sissy
3 years ago
0:57

PornHub

big dildo crossdresser sissy

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Huge Dildo in My Sissy Ass
2 months ago
0:57

xHamster

Huge Dildo in My Sissy Ass

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Sissy degrade
4 years ago
0:57

PornHub

Sissy degrade

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British Booty Sissy Twerking on Balcony in Public
3 years ago
0:56

PornHub

British Booty Sissy Twerking on Balcony in Public

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sissy sex
7 years ago
0:56

xHamster

sissy sex

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Self ballbusting sissy faggot
5 years ago
0:55

PornHub

Self ballbusting sissy faggot

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tv sissy doll jerks clitty cock and eats her cum
13 years ago
0:54

xHamster

tv sissy doll jerks clitty cock and eats her cum

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Sissy Femboy Anal Training, Flass Dildo
5 years ago
0:54

PornHub

Sissy Femboy Anal Training, Flass Dildo

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Sissy husband taking big dildo 1
3 months ago
0:53

xHamster

Sissy husband taking big dildo 1

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Abdl sissy boy jerking off into wet diaper during change heavy cum
3 years ago
0:53

PornHub

Abdl sissy boy jerking off into wet diaper during change heavy cum

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Sissy before and after serving master
4 years ago
0:53

xHamster

Sissy before and after serving master

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Sissy the Hedgehog
7 years ago
0:53

xHamster

Sissy the Hedgehog

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sissy sex
7 years ago
0:52

xHamster

sissy sex

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Just another slutty panty sissy boy fucked
7 years ago
0:51

xHamster

Just another slutty panty sissy boy fucked

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Mesmerizing You to Go Gay While You Rub Your Wet Sissy Clitty
5 months ago
0:51

xHamster

Mesmerizing You to Go Gay While You Rub Your Wet Sissy Clitty

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Amber Mei Neil - Billiard 8-Ball in my Sissy CD Asshole
5 years ago
0:51

PornHub

Amber Mei Neil - Billiard 8-Ball in my Sissy CD Asshole

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Sissy James Haslum CBT with Glue
7 years ago
0:50

xHamster

Sissy James Haslum CBT with Glue

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sissy
4 years ago
0:50

xHamster

sissy

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Sissy gets long fucked!
7 years ago
0:50

xHamster

Sissy gets long fucked!

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Sissy Juice
7 years ago
0:49

xHamster

Sissy Juice

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Michelle sissy dildo play
4 years ago
0:49

xHamster

Michelle sissy dildo play

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The Sissy Trainer: Goddess Pussy Worship
2 months ago
0:48

PornoXO

The Sissy Trainer: Goddess Pussy Worship

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Sissy Ass Closeup & Gape
3 months ago
0:47

xHamster

Sissy Ass Closeup & Gape

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Cock Cage Self Facial! Sissy Crossdresser Prostate Orgasm! Thick Cum Ropes!
5 years ago
0:47

PornHub

Cock Cage Self Facial! Sissy Crossdresser Prostate Orgasm! Thick Cum Ropes!

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how a true sissy masturbates
7 years ago
0:47

xHamster

how a true sissy masturbates

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Sissy swallows cum (from last video, forgot to include)
5 years ago
0:47

PornHub

Sissy swallows cum (from last video, forgot to include)

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Kim and her sissy
13 years ago
0:45

xHamster

Kim and her sissy

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Sissy slut
6 years ago
0:44

xHamster

Sissy slut

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Sissy gurl
4 years ago
0:44

xHamster

Sissy gurl

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sissy femboy flows like a bitch from an anal dildo ( crossdresser ts)
4 years ago
0:44

PornHub

sissy femboy flows like a bitch from an anal dildo ( crossdresser ts)

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Smoking Sissy And Tranny Bimbo
9 years ago
0:41

xHamster

Smoking Sissy And Tranny Bimbo

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Humping My Sissy Dakimakura Boyfriend
6 years ago
0:41

PornHub

Humping My Sissy Dakimakura Boyfriend

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ItsZoeStarr - Sissy Hands Free Sissygasm
4 years ago
0:39

PornHub

ItsZoeStarr - Sissy Hands Free Sissygasm

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Sissy slut Melanie part two - anal plug
4 months ago
0:39

xHamster

Sissy slut Melanie part two - anal plug

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sissy slut anal dildo
3 months ago
0:39

xHamster

sissy slut anal dildo

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Trans sissy fucks big black dildo
5 years ago
0:39

xHamster

Trans sissy fucks big black dildo

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Sissy Chastity Pee in Wine Glass
3 years ago
0:38

PornHub

Sissy Chastity Pee in Wine Glass

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The sissy, his Wife & The Saleswoman - Sissy Nylon Humiliation Trailer
5 years ago
0:38

PornHub

The sissy, his Wife & The Saleswoman - Sissy Nylon Humiliation Trailer

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A sissy topping a bottom
4 years ago
0:38

xHamster

A sissy topping a bottom

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me natalie gay sissy finger my big booty tight pink boi pussy
3 months ago
0:37

xHamster

me natalie gay sissy finger my big booty tight pink boi pussy

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Sissy swallows BBC load
5 years ago
0:37

PornHub

Sissy swallows BBC load

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Sissy Francis Malice the End New Face 2
2 months ago
0:37

xHamster

Sissy Francis Malice the End New Face 2

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Pink sissy maid in chastity
2 months ago
0:37

xHamster

Pink sissy maid in chastity

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sissy massive cumshot
7 years ago
0:37

xHamster

sissy massive cumshot

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Making my caged sissy boy pinch his nipples and play with his ass!
3 years ago
0:36

PornHub

Making my caged sissy boy pinch his nipples and play with his ass!

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Sissy Lia - Assplay and Gaping - CD DWT Crossdresser
5 years ago
0:36

xHamster

Sissy Lia - Assplay and Gaping - CD DWT Crossdresser

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Kim and sissy
13 years ago
0:35

xHamster

Kim and sissy

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Sissy showcase 2
7 years ago
0:35

xHamster

Sissy showcase 2

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sissy claire.
14 years ago
0:33

xHamster

sissy claire.

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Your New Sissy Name - Feminization - Preview
4 years ago
0:33

PornHub

Your New Sissy Name - Feminization - Preview

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Sissy PAWG Maid ruined by a THICK BBC machine
3 years ago
0:33

PornHub

Sissy PAWG Maid ruined by a THICK BBC machine

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Humiliating the crossdressing sissy whiteboy, SPH
8 years ago
0:32

xHamster

Humiliating the crossdressing sissy whiteboy, SPH

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Preparing our sissy for Vegas - Ft. Lola Fawn (Preview)
4 years ago
0:32

PornHub

Preparing our sissy for Vegas - Ft. Lola Fawn (Preview)

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obedient sissy deepthroat
3 years ago
0:32

PornHub

obedient sissy deepthroat

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CD smooth sissy wank in blue nylon and silk
14 years ago
0:31

xHamster

CD smooth sissy wank in blue nylon and silk

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sissy boot licking
5 months ago
0:31

BravoTube

sissy boot licking

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Sissy Andrea in Fucked the Ass
2 months ago
0:31

xHamster

Sissy Andrea in Fucked the Ass

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Sissy girl accidentally came in her pissy diaper
3 years ago
0:30

PornHub

Sissy girl accidentally came in her pissy diaper

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Sissy bitch used and trained by 2 Mistresses
3 years ago
0:30

PornHub

Sissy bitch used and trained by 2 Mistresses

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Sissy's First Wig - Feminization Femdom Sissy Training - Preview
3 years ago
0:30

PornHub

Sissy's First Wig - Feminization Femdom Sissy Training - Preview

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BIG BOOTY CD SISSY TRAP SLUT CUMS HANDS FREE SISSYGASM FROM ANAL DILDO
4 years ago
0:30

PornHub

BIG BOOTY CD SISSY TRAP SLUT CUMS HANDS FREE SISSYGASM FROM ANAL DILDO

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Turning You Into A Sissy Slut 6: Anal Training (Preview)
4 years ago
0:30

PornHub

Turning You Into A Sissy Slut 6: Anal Training (Preview)

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Demanding Oral From My Sissy Wife - Clara Dee POV
3 months ago
0:29

xHamster

Demanding Oral From My Sissy Wife - Clara Dee POV

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Mature Shemale Couple Fuck Sissy w Rianna James, Scott Knight (Teaser)
3 years ago
0:29

PornHub

Mature Shemale Couple Fuck Sissy w Rianna James, Scott Knight (Teaser)

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Sissy Baby prepares for Chastity and Pampering
2 months ago
0:28

xHamster

Sissy Baby prepares for Chastity and Pampering

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Sissy Sucking Dildo Wigless
26 days ago
0:25

xHamster

Sissy Sucking Dildo Wigless

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Sissy love play
5 months ago
0:25

xHamster

Sissy love play

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Sissy ride
4 years ago
0:24

PornHub

Sissy ride

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Sissy cumming
6 years ago
0:24

xHamster

Sissy cumming

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Sissy squirty cumshot for daddy
4 years ago
0:24

xHamster

Sissy squirty cumshot for daddy

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Sissy mesmerize mantras (Preview)
3 years ago
0:23

PornHub

Sissy mesmerize mantras (Preview)

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Sissy showcase 31
7 years ago
0:23

xHamster

Sissy showcase 31

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sexy white submissive sissy showing off her fe,ininazation new body
4 months ago
0:22

xHamster

sexy white submissive sissy showing off her fe,ininazation new body

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Shez and Mr E Dungeon Sissy
4 years ago
0:22

PornHub

Shez and Mr E Dungeon Sissy

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sissy slut
8 years ago
0:22

xHamster

sissy slut

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Bigger Blacker BBC Sissy Training Verbal Humilation
5 years ago
0:22

PornHub

Bigger Blacker BBC Sissy Training Verbal Humilation

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hair washing with piss for sissy
5 months ago
0:21

AnyPorn

hair washing with piss for sissy

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Sweet sissy boy
6 years ago
0:20

xHamster

Sweet sissy boy

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Sissy white boy has fun feminizing himself
3 months ago
0:20

xHamster

Sissy white boy has fun feminizing himself

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Crossdressing sissy slut gently caressing chastity cage
2 months ago
0:19

xHamster

Crossdressing sissy slut gently caressing chastity cage

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Sissy Walt dancing for Master
5 years ago
0:19

xHamster

Sissy Walt dancing for Master

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Sissy anal training
7 years ago
0:18

xHamster

Sissy anal training

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Sissy fun
5 years ago
0:18

xHamster

Sissy fun

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Sissy beta bitch boi
4 years ago
0:17

xHamster

Sissy beta bitch boi

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sissy
6 years ago
0:16

xHamster

sissy

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Sissy getting fucked
7 years ago
0:15

BravoTube

Sissy getting fucked

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Kinky Sissy Slut Part 2
5 years ago
0:15

xHamster

Kinky Sissy Slut Part 2

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Sissy slut dripping daddies cum
3 years ago
0:14

PornHub

Sissy slut dripping daddies cum

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sissy slut tiffany in her maids dress
7 years ago
0:12

xHamster

sissy slut tiffany in her maids dress

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Horny with a sissy
5 years ago
0:12

xHamster

Horny with a sissy

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Happy Sissy Party with Mistress Lydia D’Ouleur
4 years ago
0:09

PornHub

Happy Sissy Party with Mistress Lydia D’Ouleur

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Omg!!! Dumb sissy meat is dripping!
6 years ago
0:08

xHamster

Omg!!! Dumb sissy meat is dripping!

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PREVIEW NYC Sissy Slur Twerking
4 years ago
0:08

xHamster

PREVIEW NYC Sissy Slur Twerking

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