Sissy Anal: 517 Videos

SISSY SISIFICATION CHASTITY ANAL PEGGING FEMDOM WORSHIP DOMINATION BNWO
1 year ago
11:03

JizzBunker

SISSY SISIFICATION CHASTITY ANAL PEGGING FEMDOM WORSHIP DOMINATION BNWO

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Beautiful sissy Shemale playing with her hole
10 months ago
11:01

JizzBunker

Beautiful sissy Shemale playing with her hole

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Cornelius and Arnold Sissy gay
1 year ago
10:55

XXXDan

Cornelius and Arnold Sissy gay

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Sissy-transvestite fucked naked and spanked by chubby daddy
1 year ago
10:50

XXXDan

Sissy-transvestite fucked naked and spanked by chubby daddy

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Chastity PEE and FISTING for SISSY slave
1 year ago
10:36

xHamster

Chastity PEE and FISTING for SISSY slave

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Sissy In Her Purple Dress
1 year ago
10:30

xHamster

Sissy In Her Purple Dress

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SISSY TRAP - 7 DILDOS PLAY MY ASS
1 year ago
10:26

XXXDan

SISSY TRAP - 7 DILDOS PLAY MY ASS

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Sissy Marissa trainning her hole for use
1 year ago
10:24

xHamster

Sissy Marissa trainning her hole for use

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Sissy 4: Cum Lover
1 year ago
10:21

JizzBunker

Sissy 4: Cum Lover

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Loveable sissy 21
1 year ago
10:20

JizzBunker

Loveable sissy 21

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Sissy Bootcamp vol 2 Blowjob and Anal Training
3 years ago
10:18

XXXDan

Sissy Bootcamp vol 2 Blowjob and Anal Training

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Sissy cuckold transformation
3 years ago
10:17

JizzBunker

Sissy cuckold transformation

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Sissy boy VovcixFox in pantyhose Fingering his Tight Asshole
8 months ago
10:16

XXXDan

Sissy boy VovcixFox in pantyhose Fingering his Tight Asshole

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BBW Sissy Girl in Chastity Rides Her Favorite Dildo
1 year ago
10:15

XXXDan

BBW Sissy Girl in Chastity Rides Her Favorite Dildo

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SweetFemdom Jade Indica fucking Sissy Slave Fina with a strap on
1 year ago
10:15

XXXDan

SweetFemdom Jade Indica fucking Sissy Slave Fina with a strap on

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Sissy - anal training
1 year ago
10:15

XXXDan

Sissy - anal training

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Woman fucks a man with a big dildo with strap PEGGING POV #98 Turns It Into Her Sissy Part 1
1 year ago
10:14

xHamster

Woman fucks a man with a big dildo with strap PEGGING POV #98 Turns It Into Her Sissy Part 1

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Sissy femboy fucks with dildo
1 year ago
10:11

JizzBunker

Sissy femboy fucks with dildo

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Sissy Chastity Sissygasm Drinking - Trans Cumslut Jessica Bloom
1 year ago
10:11

xHamster

Sissy Chastity Sissygasm Drinking - Trans Cumslut Jessica Bloom

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Fuckmachine sissy cunt pig huge dildo and plug
11 months ago
10:09

XXXDan

Fuckmachine sissy cunt pig huge dildo and plug

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If you have a small dick, its good to be a sissy. kiss it
3 years ago
10:05

JizzBunker

If you have a small dick, its good to be a sissy. kiss it

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Sexy Blonde Sissy Bailey Wilde in Chastity Fucked
1 year ago
10:05

xHamster

Sexy Blonde Sissy Bailey Wilde in Chastity Fucked

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Dirty sissy slut
2 years ago
10:04

XXXDan

Dirty sissy slut

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Sissy squirts piss through her cock cage while stretching her anal pussy with big toys
1 year ago
10:03

JizzBunker

Sissy squirts piss through her cock cage while stretching her anal pussy with big toys

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Sissy CD ass fucked bareback
1 year ago
9:59

XXXDan

Sissy CD ass fucked bareback

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ALL MY MOTHERS LOVE- 6 - SISSY - MAXIMUM GAPE - GLASS BUTTPLUG - LOOK DEEP INSIDE ASS - GAY GAPE
3 years ago
9:59

XXXDan

ALL MY MOTHERS LOVE- 6 - SISSY - MAXIMUM GAPE - GLASS BUTTPLUG - LOOK DEEP INSIDE ASS - GAY GAPE

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Crossdresser sissy takes BBC and gets creampied deep in pussy
1 year ago
9:58

XXXDan

Crossdresser sissy takes BBC and gets creampied deep in pussy

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NASTY SISSY SLUT'S EXTREME ANAL STRETCHING
7 years ago
9:57

xHamster

NASTY SISSY SLUT'S EXTREME ANAL STRETCHING

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DOLLED UP SOFTCORE RUSSIAN SISSY TRAP WIFEY SLUT
7 years ago
9:55

xHamster

DOLLED UP SOFTCORE RUSSIAN SISSY TRAP WIFEY SLUT

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Sissy Candy in black lingerie and chastity is locked and impaled on her dildo stand
1 year ago
9:39

xHamster

Sissy Candy in black lingerie and chastity is locked and impaled on her dildo stand

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Pretty Sissy Puppet on Display
2 years ago
9:37

JizzBunker

Pretty Sissy Puppet on Display

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Sissy play - FemDom POV video - free porn clip - Arya Grander
2 years ago
9:35

XXXDan

Sissy play - FemDom POV video - free porn clip - Arya Grander

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Mr. Hankeys Thicky Nicky fucks busty Sissy until her little Clitty squirts
1 year ago
9:34

XXXDan

Mr. Hankeys Thicky Nicky fucks busty Sissy until her little Clitty squirts

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BILLIARD BALLS GAPING ASS - SISSY - LADYBOY GAPING WIDE SISSY TEEN
3 years ago
9:31

XXXDan

BILLIARD BALLS GAPING ASS - SISSY - LADYBOY GAPING WIDE SISSY TEEN

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Slut Sissy Crossdresser Cum Compilation
6 years ago
9:27

xHamster

Slut Sissy Crossdresser Cum Compilation

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Sissy bottom taking raw loads
6 years ago
9:21

xHamster

Sissy bottom taking raw loads

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Sexiest Sissy Fucked by Fuck Machine
1 year ago
9:20

xHamster

Sexiest Sissy Fucked by Fuck Machine

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SISSY LESSONS
2 years ago
9:19

XXXDan

SISSY LESSONS

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sissy boy slut BRUTALY POUNDING his ASS into a GAPING HOLE
15 years ago
9:16

xHamster

sissy boy slut BRUTALY POUNDING his ASS into a GAPING HOLE

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Sweet sissy enjoying big black dildo deep in her ass
1 year ago
9:11

xHamster

Sweet sissy enjoying big black dildo deep in her ass

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Amazing Ass Sissy Slut Work Her Ass off with Big Toys and a Fuck Machine
1 year ago
9:09

xHamster

Amazing Ass Sissy Slut Work Her Ass off with Big Toys and a Fuck Machine

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Tiny sissy with huge anal toy
1 year ago
9:08

xHamster

Tiny sissy with huge anal toy

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Sissy anal slut rubber fist
1 year ago
9:01

XXXDan

Sissy anal slut rubber fist

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Sissy rides her new toy
1 year ago
9:00

JizzBunker

Sissy rides her new toy

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Ballbusting  hostess  Extreme  Femdom  Cruel  mistress  CBT  Binding  Chastity  Sissy  Foot  Legs
2 years ago
8:58

XXXDan

Ballbusting hostess Extreme Femdom Cruel mistress CBT Binding Chastity Sissy Foot Legs

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WHITE SISSY CD SLUT GAPING HER ASS WITH HUGE BLACKS AND FIST
6 years ago
8:57

xHamster

WHITE SISSY CD SLUT GAPING HER ASS WITH HUGE BLACKS AND FIST

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Part 2 sissy games She licks his ass and stretches it and then penetrates him with her strap-on and his big plastic cock.
1 year ago
8:51

XXXDan

Part 2 sissy games She licks his ass and stretches it and then penetrates him with her strap-on and his big plastic cock.

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Sissy Peg's locked clitty
7 years ago
8:50

xHamster

Sissy Peg's locked clitty

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Sissy maid serving mistress
1 year ago
8:50

xHamster

Sissy maid serving mistress

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This sissy redhead loves having a black rod in her ass
3 years ago
8:48

JizzBunker

This sissy redhead loves having a black rod in her ass

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Sissy in Leather Leotard and Chastity takes Huge Dildo up her Ass
1 year ago
8:45

xHamster

Sissy in Leather Leotard and Chastity takes Huge Dildo up her Ass

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Sissy brainwashing
1 year ago
8:39

XXXDan

Sissy brainwashing

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Sissy slut blowjob before anal sex
1 year ago
8:36

JizzBunker

Sissy slut blowjob before anal sex

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SISSY IS ALWAYS HUNGRY FOR RAW COCK
2 years ago
8:34

JizzBunker

SISSY IS ALWAYS HUNGRY FOR RAW COCK

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Sissy handjob
2 years ago
8:26

JizzBunker

Sissy handjob

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Sissy play outdoors. dildo riding in the forest
1 year ago
8:24

JizzBunker

Sissy play outdoors. dildo riding in the forest

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First time fucking a white sissy
6 years ago
8:24

xHamster

First time fucking a white sissy

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SISSY IS ALWAYS HUNGRY FOR RAW COCK
2 years ago
8:23

JizzBunker

SISSY IS ALWAYS HUNGRY FOR RAW COCK

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Part 1 Miss Santa fucks a sissy - Happy New Year 2024
1 year ago
8:22

XXXDan

Part 1 Miss Santa fucks a sissy - Happy New Year 2024

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Very Sexy Blonde Sissy Masturbating with Redhead Trans Woman
1 year ago
8:22

xHamster

Very Sexy Blonde Sissy Masturbating with Redhead Trans Woman

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Feminizing Sissys, Sissy Training, Be a Sissy
1 year ago
8:12

xHamster

Feminizing Sissys, Sissy Training, Be a Sissy

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Sissy Secretary Solo Fun on the Table
1 year ago
8:12

xHamster

Sissy Secretary Solo Fun on the Table

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Raging sissy
7 years ago
8:11

xHamster

Raging sissy

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redhead sissy fucked
6 years ago
8:08

xHamster

redhead sissy fucked

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Bbc fuck my sissy princess pussy
7 years ago
8:06

xHamster

Bbc fuck my sissy princess pussy

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Sissy
10 months ago
8:05

XXXDan

Sissy

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Sissy anal training
6 years ago
8:04

NuVid

Sissy anal training

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ALL MY MOMS LOVE - NN - PIGHOLE - PYRAMIDE - DIRTYGARDENBOY - DGB - MULTIPLE EXTREME BIG TOYS - SISSY
3 years ago
8:04

JizzBunker

ALL MY MOMS LOVE - NN - PIGHOLE - PYRAMIDE - DIRTYGARDENBOY - DGB - MULTIPLE EXTREME BIG TOYS - SISSY

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DGB C - PIGHOLE - PYRAMID - DIRTYGARDENBOY - DGB - MULTIPLE VERY BIG TOYS - SISSY
2 years ago
8:04

XXXDan

DGB C - PIGHOLE - PYRAMID - DIRTYGARDENBOY - DGB - MULTIPLE VERY BIG TOYS - SISSY

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Amateur Strapon Pegging - Sissy Guy Takes Strapon Like A Real Pussy
4 years ago
8:04

JizzBunker

Amateur Strapon Pegging - Sissy Guy Takes Strapon Like A Real Pussy

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Ballbusting  Hostess  Extreme  femdom  Cruel  mistress  PTA  Binding  Chastity  Sissy  leg  Legs
1 year ago
8:03

XXXDan

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Sissy Beautiful.avi
8 years ago
8:00

xHamster

Sissy Beautiful.avi

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Sissy guy in bisexual MMF threesome
2 years ago
8:00

XXXDan

Sissy guy in bisexual MMF threesome

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Sissy slave plays with herself
1 year ago
7:49

JizzBunker

Sissy slave plays with herself

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Sissy takes black cock
1 year ago
7:46

xHamster

Sissy takes black cock

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Sissy masturbates
1 year ago
7:44

XXXDan

Sissy masturbates

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I Need a Real Cock in My Sissy Ass
10 months ago
7:41

XXXDan

I Need a Real Cock in My Sissy Ass

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Ballbusting  hostess  Extreme  Femdom  Cruel  mistress  CBT  Binding  Chastity  Sissy  Foot  Legs
2 years ago
7:41

XXXDan

Ballbusting hostess Extreme Femdom Cruel mistress CBT Binding Chastity Sissy Foot Legs

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Femdom babe in fishnet stockings ass drilled by sissy crossdresser
2 years ago
7:40

XXXDan

Femdom babe in fishnet stockings ass drilled by sissy crossdresser

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Sissy cums while putting a dildo in her ass
1 year ago
7:40

XXXDan

Sissy cums while putting a dildo in her ass

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Sissy Fuck Machine Training
1 year ago
7:39

xHamster

Sissy Fuck Machine Training

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Destroying My Big Sissy Ass with a Fuck Machine and Huge Dildos
1 year ago
7:38

xHamster

Destroying My Big Sissy Ass with a Fuck Machine and Huge Dildos

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The way sissy sees the world
8 months ago
7:38

JizzBunker

The way sissy sees the world

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Mouthy Asian panda dominatrix domina for sissy men
6 years ago
7:36

PornGem

Mouthy Asian panda dominatrix domina for sissy men

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Ken Trains Candy to Ride BBC Reverse Cowgirl with Verbal Domination Then Fucks My Pussy Missionary - Candy Ass Sissy
1 year ago
7:36

xHamster

Ken Trains Candy to Ride BBC Reverse Cowgirl with Verbal Domination Then Fucks My Pussy Missionary - Candy Ass Sissy

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Gay Sissy crossdresser Fuck and blowjob with big black dildo
1 year ago
7:35

xHamster

Gay Sissy crossdresser Fuck and blowjob with big black dildo

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I Love Dressing up as a Sissy, and Receiving What I Want so Much
11 months ago
7:34

JizzBunker

I Love Dressing up as a Sissy, and Receiving What I Want so Much

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SISSY PISSING SLUT COMPILATION!
7 years ago
7:31

xHamster

SISSY PISSING SLUT COMPILATION!

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Sissy crossdressed slut sucks, fucks and gets creampied
1 year ago
7:30

JizzBunker

Sissy crossdressed slut sucks, fucks and gets creampied

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Gay porn.Slut sissy crossdresser fucking big black dildo
1 year ago
7:29

xHamster

Gay porn.Slut sissy crossdresser fucking big black dildo

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Sissy slut sissygasm and plays with Ai waiting for grindr date
1 year ago
7:24

xHamster

Sissy slut sissygasm and plays with Ai waiting for grindr date

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Daddy And His Friends - Sissy Caption Story With Lana Rhoades
1 year ago
7:23

PornoXO

Daddy And His Friends - Sissy Caption Story With Lana Rhoades

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Deep Anal Training Sissy Caged Cumshot  Monster Dildo Sohimi vs Jessica Bloom
1 year ago
7:21

XXXDan

Deep Anal Training Sissy Caged Cumshot Monster Dildo Sohimi vs Jessica Bloom

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BIG WET SISSY ASSES POV
1 year ago
7:16

xHamster

BIG WET SISSY ASSES POV

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Sissy Allison Lace: I’m Such A Faggot
7 years ago
7:12

xHamster

Sissy Allison Lace: I’m Such A Faggot

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Sissy Sluts Guide to Total Debauchery. Sissy Trainer by Hornygur
1 year ago
7:12

XXXDan

Sissy Sluts Guide to Total Debauchery. Sissy Trainer by Hornygur

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SISSY LOVELASKA - New dig dildo. new big size
9 months ago
7:12

JizzBunker

SISSY LOVELASKA - New dig dildo. new big size

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Sissy Slut Guide To Total Whoredom Sissy Trainer By Hornygur
6 years ago
7:12

xHamster

Sissy Slut Guide To Total Whoredom Sissy Trainer By Hornygur

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Amateur sissy gay twink anal movies Damien Telrue and Dustin
7 years ago
7:10

NuVid

Amateur sissy gay twink anal movies Damien Telrue and Dustin

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Sissy Jolene Riding Dick in Her Plaid Lingerie
1 year ago
7:09

xHamster

Sissy Jolene Riding Dick in Her Plaid Lingerie

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Locked sissy riding POV
6 years ago
7:08

xHamster

Locked sissy riding POV

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Sissy Bailey Wilde in Chastity Fucked
1 year ago
7:07

xHamster

Sissy Bailey Wilde in Chastity Fucked

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slutty sissy playing
6 years ago
7:03

xHamster

slutty sissy playing

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Young sissy gay twink anal fucked Timmy Gets Taught A
6 years ago
7:02

DrTuber

Young sissy gay twink anal fucked Timmy Gets Taught A

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Sissy with Dildo
9 months ago
6:57

JizzBunker

Sissy with Dildo

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Sissy Marissa is hungry for cock
1 year ago
6:56

JizzBunker

Sissy Marissa is hungry for cock

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You are my sissy whore and you are going to pimp yourself!!!
1 year ago
6:50

XXXDan

You are my sissy whore and you are going to pimp yourself!!!

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6 years ago
6:48

JizzBunker

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6 years ago
6:48

XXXDan

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Sissy Riding Dildo and Swinging Her Clitty
1 year ago
6:43

xHamster

Sissy Riding Dildo and Swinging Her Clitty

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Sissy Daisy Sucks Crossdresser Bailey Wilde's Huge Cock
1 year ago
6:39

xHamster

Sissy Daisy Sucks Crossdresser Bailey Wilde's Huge Cock

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Feminine sissy fucks hard without a condom - homemade
2 years ago
6:39

JizzBunker

Feminine sissy fucks hard without a condom - homemade

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Sissy fucks her ass with a black dildo
1 year ago
6:34

JizzBunker

Sissy fucks her ass with a black dildo

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Sissy Slut in Red Lingerie plays with herself
8 months ago
6:30

JizzBunker

Sissy Slut in Red Lingerie plays with herself

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DGB - Y - PINK LATEX GLOVE FIST DEEP ANAL FEMDOM SISSY.MP4
2 years ago
6:29

JizzBunker

DGB - Y - PINK LATEX GLOVE FIST DEEP ANAL FEMDOM SISSY.MP4

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Sissy Gets Hot Cock Part 4
1 year ago
6:27

xHamster

Sissy Gets Hot Cock Part 4

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Horny sissy needs dick his for birthday
1 year ago
6:27

xHamster

Horny sissy needs dick his for birthday

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SMALL TITS TS SHEMALE SISSY TRAP BEAUTY # 2
7 years ago
6:26

xHamster

SMALL TITS TS SHEMALE SISSY TRAP BEAUTY # 2

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Big dildo in my sissy hole
1 year ago
6:26

xHamster

Big dildo in my sissy hole

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Sissy experience
4 years ago
6:26

XXXDan

Sissy experience

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Sissy bunny plays with dildo
8 months ago
6:26

JizzBunker

Sissy bunny plays with dildo

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Crossdresser in public with - My First Tattoo - Anal Sissy Crossdresser Femboy
1 year ago
6:20

xHamster

Crossdresser in public with - My First Tattoo - Anal Sissy Crossdresser Femboy

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Brunette sissy bareback at home
2 years ago
6:19

JizzBunker

Brunette sissy bareback at home

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Trans sissy sucks a big dildo, rides it and cums
1 year ago
6:19

xHamster

Trans sissy sucks a big dildo, rides it and cums

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Sissy slut gets fucked
1 year ago
6:18

JizzBunker

Sissy slut gets fucked

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Sissy Training Her Holes
1 year ago
6:16

xHamster

Sissy Training Her Holes

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Sissy Getting Fucked
8 months ago
6:16

XXXDan

Sissy Getting Fucked

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Train Your Sissy Self
1 year ago
6:16

JizzBunker

Train Your Sissy Self

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BBW Femdom - Pegging Chaste Sissy Anal
1 year ago
6:15

xHamster

BBW Femdom - Pegging Chaste Sissy Anal

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Sissy Guide - How to Anal Orgasm in Chastity Cage - Jessica Bloom
1 year ago
6:14

xHamster

Sissy Guide - How to Anal Orgasm in Chastity Cage - Jessica Bloom

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Serve Men, Sissy
1 year ago
6:12

JizzBunker

Serve Men, Sissy

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Sissy Housemaid fucked my wife in the ass and I loved it
2 years ago
6:12

JizzBunker

Sissy Housemaid fucked my wife in the ass and I loved it

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Sissy stretches her ass with multiple zoo-dildos
7 years ago
6:11

xHamster

Sissy stretches her ass with multiple zoo-dildos

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Mistress fucks sissy twink in his anal hole so brutal
11 months ago
6:05

XXXDan

Mistress fucks sissy twink in his anal hole so brutal

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Ballbusting  hostess  Extreme  Femdom  Cruel  mistress  CBT  Binding  Chastity  Sissy  Foot  Legs
2 years ago
6:03

JizzBunker

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Fucking My Ass Until Sissygasm Lke a Sissy Bitch
8 months ago
6:01

XXXDan

Fucking My Ass Until Sissygasm Lke a Sissy Bitch

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Sissy fucked in chastity
3 years ago
6:01

XXXDan

Sissy fucked in chastity

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Sissy rides
11 months ago
6:00

JizzBunker

Sissy rides

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SISSY SOUNDING -35 -ZO GEILE FEMBOY - BLONDE RUNNING - SOLO - SOUND - EXPERIENCED DEEP ANAL
1 year ago
6:00

XXXDan

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