Sissy: 1244 Videos

Sissy spanked and fucked in the ass with a toy
4 years ago
24:00

PornHub

Sissy spanked and fucked in the ass with a toy

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Sissy Cumshot No Hands, Big Ass Tranny MILF
6 months ago
1:40

xHamster

Sissy Cumshot No Hands, Big Ass Tranny MILF

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Stroking my sissy cock
5 years ago
0:52

PornHub

Stroking my sissy cock

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Femboy Sissy Fucks a Dyke Tomboy - Gender Bender Sex
4 years ago
12:38

PornHub

Femboy Sissy Fucks a Dyke Tomboy - Gender Bender Sex

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Sissy fucked
1 year ago
6:31

XXXDan

Sissy fucked

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Sissy Femboy gently fucks a wet pussy with a hard dick and enjoys ( ts )
4 years ago
17:14

PornHub

Sissy Femboy gently fucks a wet pussy with a hard dick and enjoys ( ts )

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HOT PRE-CUMMING Masturbation Sissy Cock Clapping White Blonde Dhemale Model Crossdresser
3 months ago
3:36

XXXDan

HOT PRE-CUMMING Masturbation Sissy Cock Clapping White Blonde Dhemale Model Crossdresser

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Brandy the Homo Shemale Breaks in a Sissy Roadhead Style
3 years ago
3:46

PornHub

Brandy the Homo Shemale Breaks in a Sissy Roadhead Style

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Sissy teasing
3 years ago
0:20

PornHub

Sissy teasing

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Pegging His Tight Sissy Asshole
3 years ago
0:24

PornHub

Pegging His Tight Sissy Asshole

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Sissy Gets Caned and Edged
3 years ago
0:18

PornHub

Sissy Gets Caned and Edged

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

XXXDan

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

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Sissy Twink BBC Dildo Anal Fun
4 years ago
6:45

PornHub

Sissy Twink BBC Dildo Anal Fun

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Made my little sissy spank himself!!
3 years ago
0:10

PornHub

Made my little sissy spank himself!!

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Hairy Sissy Wears Panties in the Shower! Wet Clothes, Big Ass! Soapy!
5 years ago
4:48

PornHub

Hairy Sissy Wears Panties in the Shower! Wet Clothes, Big Ass! Soapy!

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Kinky Sissy Bitch ride big dildo
5 months ago
0:16

xHamster

Kinky Sissy Bitch ride big dildo

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Sissy milks her cock with a lot of cum on her panties
4 years ago
9:55

PornHub

Sissy milks her cock with a lot of cum on her panties

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Sissy CD Jo and cum
5 years ago
1:25

PornHub

Sissy CD Jo and cum

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Teen Sissy slut lee fucks ass and cums locked In chastity
5 years ago
2:14

PornHub

Teen Sissy slut lee fucks ass and cums locked In chastity

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Cuckolds MILF needs huge BBC Sissy husband short dick
1 year ago
17:24

JizzBunker

Cuckolds MILF needs huge BBC Sissy husband short dick

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Sissy Neri fucked by Alex Magni in Firenze
4 months ago
11:00

XXXDan

Sissy Neri fucked by Alex Magni in Firenze

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Horny Sissy Bimbo
5 years ago
0:36

PornHub

Horny Sissy Bimbo

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Sissy loves bbc 3
3 years ago
14:45

PornHub

Sissy loves bbc 3

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ItsZoeStarr - Sissy's Huge Cock Hands Free Orgasm from Lovense Lush
4 years ago
1:45

PornHub

ItsZoeStarr - Sissy's Huge Cock Hands Free Orgasm from Lovense Lush

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Solo Male Dirty Talk for Slaves and Sissy Sluts while jerking off big white cock
3 years ago
4:36

PornHub

Solo Male Dirty Talk for Slaves and Sissy Sluts while jerking off big white cock

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ItsZoeStarr - Sissy Bimbo Limp Premature Cum
4 years ago
1:22

PornHub

ItsZoeStarr - Sissy Bimbo Limp Premature Cum

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Getting DP by my sissy and a BBC dildo!
3 years ago
2:12

PornHub

Getting DP by my sissy and a BBC dildo!

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Sissy shows off in electro chastity and ball stretcher via camart
3 years ago
4:38

PornHub

Sissy shows off in electro chastity and ball stretcher via camart

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Mature Sissy fucks her ass with a black dildo
29 days ago
6:18

XXXDan

Mature Sissy fucks her ass with a black dildo

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Sissy Taken Home By Alpha For Foot Domination
4 years ago
9:44

PornHub

Sissy Taken Home By Alpha For Foot Domination

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sissy bobby get trained for strap-on sucking
3 years ago
0:18

PornHub

sissy bobby get trained for strap-on sucking

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Dutch Crossdresser Sissy Tranny Slow-motion TS Cock & Hot Shemale Ass Tease in Sexy Leopard Panties
4 years ago
3:40

PornHub

Dutch Crossdresser Sissy Tranny Slow-motion TS Cock & Hot Shemale Ass Tease in Sexy Leopard Panties

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Sissy tranny trap fucks herself silly
4 years ago
14:32

PornHub

Sissy tranny trap fucks herself silly

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ItsZoeStarr - Sissy Bimbo Sissygasms 2 Times Riding Dildo
4 years ago
3:17

PornHub

ItsZoeStarr - Sissy Bimbo Sissygasms 2 Times Riding Dildo

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Sissy's Electric Training - Star Nine Femdom POV Electric Play Trailer
6 years ago
0:54

PornHub

Sissy's Electric Training - Star Nine Femdom POV Electric Play Trailer

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Young twink crossdresser in public in the city, sissy
40 days ago
5:59

JizzBunker

Young twink crossdresser in public in the city, sissy

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Sissygasm Challenge Day 1 - Sissy Trap Boy Rides Dildo
3 years ago
23:42

PornHub

Sissygasm Challenge Day 1 - Sissy Trap Boy Rides Dildo

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Sissy femboy tries to ride a giant black dildo
2 months ago
16:15

XXXDan

Sissy femboy tries to ride a giant black dildo

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Sissy MESMERIZE MIND washer Phase 3 Cock Hungry Whore LOOP IT AND EDGE TO GAY PORN
3 years ago
2:57

PornHub

Sissy MESMERIZE MIND washer Phase 3 Cock Hungry Whore LOOP IT AND EDGE TO GAY PORN

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sissy getting ready for cock
5 years ago
0:52

PornHub

sissy getting ready for cock

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Anal dildo sissy slut bi male crossdresser femboy omneve solo
3 years ago
1:02

PornHub

Anal dildo sissy slut bi male crossdresser femboy omneve solo

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Cute dirty whore - sissy slut for mistress
1 year ago
11:01

JizzBunker

Cute dirty whore - sissy slut for mistress

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Prerecorded strapon show huge strapon for sissy bitch
3 years ago
6:02

PornHub

Prerecorded strapon show huge strapon for sissy bitch

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Sissy Caged Fag Boy Gets Drilled Doggy Style by Fuck Machine
4 years ago
1:09

PornHub

Sissy Caged Fag Boy Gets Drilled Doggy Style by Fuck Machine

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Sexy Sissy sucks
3 years ago
1:04

PornHub

Sexy Sissy sucks

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Sissy a little taped up in Highheels
5 months ago
3:39

xHamster

Sissy a little taped up in Highheels

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Sissy-Faggot Frl. Felicitas Frivol
3 months ago
0:33

xHamster

Sissy-Faggot Frl. Felicitas Frivol

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Big Booty PAWG Sissy Bimbo Aria Veronique Shows Off Her Greatest Asset
5 years ago
0:59

PornHub

Big Booty PAWG Sissy Bimbo Aria Veronique Shows Off Her Greatest Asset

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SISSY BLOWJOB AND FUCK
7 months ago
6:58

xHamster

SISSY BLOWJOB AND FUCK

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Look at this sissy
1 year ago
2:09

XXXDan

Look at this sissy

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Ass up Face Down LETS FURTHER YOUR TRAINING sissy boi
4 years ago
4:48

PornHub

Ass up Face Down LETS FURTHER YOUR TRAINING sissy boi

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Public Exposure, Sissy humiliation dare! Almost Caught!
6 years ago
8:30

PornHub

Public Exposure, Sissy humiliation dare! Almost Caught!

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Sissy Cum Squirting (loop)
3 years ago
0:22

PornHub

Sissy Cum Squirting (loop)

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Anal fisting male double sissy cd femdom f2m
1 year ago
15:45

JizzBunker

Anal fisting male double sissy cd femdom f2m

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Sissy drinks glass of piss
21 days ago
1:14

xHamster

Sissy drinks glass of piss

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hot sissy enjoy and play with her flower hole and moan
5 years ago
4:01

JizzBunker

hot sissy enjoy and play with her flower hole and moan

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Blonde Sissy Girl Trap In Sexy Lingerie Fucking Anal Big Dildo
4 years ago
0:59

PornHub

Blonde Sissy Girl Trap In Sexy Lingerie Fucking Anal Big Dildo

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Sissy mind control slut training
4 years ago
2:18

PornHub

Sissy mind control slut training

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Cute Sissy Slut deep blowjob, cum eating (Foxyq Slut Full Vercion)
4 years ago
12:20

PornHub

Cute Sissy Slut deep blowjob, cum eating (Foxyq Slut Full Vercion)

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Sissy Relyks has sissygasm and soft cums hands free riding BWC dildo on snapchat
3 years ago
0:16

PornHub

Sissy Relyks has sissygasm and soft cums hands free riding BWC dildo on snapchat

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Sissy ass play
41 days ago
2:07

JizzBunker

Sissy ass play

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Sissy riding dildo
1 year ago
17:40

XXXDan

Sissy riding dildo

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Hot sissy Brenda shows off your thong
3 months ago
4:19

JizzBunker

Hot sissy Brenda shows off your thong

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Walmart Sissy Jerkoff In Parking Lot ( Full Video On Onlyfans ). link in bio & comments
3 years ago
0:18

PornHub

Walmart Sissy Jerkoff In Parking Lot ( Full Video On Onlyfans ). link in bio & comments

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CD sissy daily anal stretching routine part 1
5 years ago
3:50

PornHub

CD sissy daily anal stretching routine part 1

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Sissy washing her natural hair
3 years ago
1:41

PornHub

Sissy washing her natural hair

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Cd sissy cum milking in glass and drinking everything
4 years ago
6:26

PornHub

Cd sissy cum milking in glass and drinking everything

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Sexy skinny sissy
8 months ago
5:22

JizzBunker

Sexy skinny sissy

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Ebony Mistress Disciplines Her Sissy Slut
6 years ago
5:02

PornHub

Ebony Mistress Disciplines Her Sissy Slut

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Cute Crossdresser Sissy Sucks and Deepthroats Dildo
3 years ago
3:49

PornHub

Cute Crossdresser Sissy Sucks and Deepthroats Dildo

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Sissy hexy playing with herself
3 years ago
4:17

PornHub

Sissy hexy playing with herself

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ItsZoeStarr - Sissy Bimbos Milks Her Big Dick
4 years ago
1:24

PornHub

ItsZoeStarr - Sissy Bimbos Milks Her Big Dick

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Big dick sissy plays With her dick
4 years ago
2:07

PornHub

Big dick sissy plays With her dick

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GF makes you her sissy and sends you on a bi date Quickie
4 years ago
2:48

PornHub

GF makes you her sissy and sends you on a bi date Quickie

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Real sissy dildo anal masturbation
3 years ago
0:28

PornHub

Real sissy dildo anal masturbation

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Fucked against the wall of my sissy femboy with cumshot
3 years ago
4:02

PornHub

Fucked against the wall of my sissy femboy with cumshot

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Caged sissy gets machine fucked close up w/filter
3 years ago
4:24

PornHub

Caged sissy gets machine fucked close up w/filter

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Fit dominatrix dominates her new sissy - Brat Perversions
38 days ago
4:52

XXXDan

Fit dominatrix dominates her new sissy - Brat Perversions

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SISSY IS ALWAYS HUNGRY FOR RAW COCK
10 months ago
29:04

JizzBunker

SISSY IS ALWAYS HUNGRY FOR RAW COCK

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Sissy fuckhole after being relentlessly pounded by monster BBC
3 years ago
0:43

PornHub

Sissy fuckhole after being relentlessly pounded by monster BBC

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Sissy in heat fucking her ass with dildo in the streets at night
5 years ago
1:52

PornHub

Sissy in heat fucking her ass with dildo in the streets at night

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Sissy in cage takes MASSIVE creampie
3 years ago
0:25

PornHub

Sissy in cage takes MASSIVE creampie

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Sexy Sissy Showering and showing her feet
3 years ago
4:15

PornHub

Sexy Sissy Showering and showing her feet

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Sissy Episode: Maid
5 years ago
2:39

PornHub

Sissy Episode: Maid

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Set your inner sissy free pmv
1 year ago
4:46

XXXDan

Set your inner sissy free pmv

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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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Why should you be in chasity forever? (Sissy training)
4 years ago
2:45

PornHub

Why should you be in chasity forever? (Sissy training)

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Sissy Cleans Up Boyfriend's Cum For Aunty Bastienne Pegging Feed Cum PREV
3 years ago
1:07

PornHub

Sissy Cleans Up Boyfriend's Cum For Aunty Bastienne Pegging Feed Cum PREV

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Desperate sissy maid shakes his caged clit while cleaning and femdom goddess gives him a quick tease
3 years ago
3:51

PornHub

Desperate sissy maid shakes his caged clit while cleaning and femdom goddess gives him a quick tease

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Lboy taira vs sissy girl
8 years ago
6:11

JizzBunker

Lboy taira vs sissy girl

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Scraping The Skin Off My Sissy Feet
32 days ago
2:35

xHamster

Scraping The Skin Off My Sissy Feet

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Amateur sissy fucks ass with dildo, whips clitty around in chastity and has sissygasm cum
3 months ago
8:15

xHamster

Amateur sissy fucks ass with dildo, whips clitty around in chastity and has sissygasm cum

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SISSY SHORTS: CROPTOP FEMBOY
5 years ago
1:53

PornHub

SISSY SHORTS: CROPTOP FEMBOY

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Sissy Moaning Loud from Dildo Pounding Part 3
4 years ago
3:56

PornHub

Sissy Moaning Loud from Dildo Pounding Part 3

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Suck my cock / AUDIO ONLY SISSY JOI
6 years ago
4:48

PornHub

Suck my cock / AUDIO ONLY SISSY JOI

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Femboy sissy gets fucked hard and cums
4 years ago
9:51

PornHub

Femboy sissy gets fucked hard and cums

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anal training of a young crossdresser big dildo in his ass ( sissy boy)
4 years ago
2:50

PornHub

anal training of a young crossdresser big dildo in his ass ( sissy boy)

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U wear panties & suck cock for me! Sissy training femdom!
3 years ago
8:43

PornHub

U wear panties & suck cock for me! Sissy training femdom!

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SMALL AND PATHETIC SISSY CUMSHOT
3 years ago
0:23

PornHub

SMALL AND PATHETIC SISSY CUMSHOT

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Sissy Cuckold Locked In  Chastity Till Hotwife Gets Home From Fucking BBB
4 years ago
0:57

PornHub

Sissy Cuckold Locked In Chastity Till Hotwife Gets Home From Fucking BBB

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Sissy Slut riding dildo hard
3 years ago
1:38

PornHub

Sissy Slut riding dildo hard

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sissy swallows precum big black cock lubing her ass with precum
6 months ago
14:43

xHamster

sissy swallows precum big black cock lubing her ass with precum

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Sissy husband loves BBC
4 years ago
1:48

PornHub

Sissy husband loves BBC

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Castigando a mi femboy sissy Crossdress
3 years ago
1:09

PornHub

Castigando a mi femboy sissy Crossdress

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Moaning Dirty Talking Sissy Crossdresser Anal Masturbation & Sissygasms Cum in High Heels & Lingerie
3 years ago
7:27

PornHub

Moaning Dirty Talking Sissy Crossdresser Anal Masturbation & Sissygasms Cum in High Heels & Lingerie

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Sissy vibrator chastity cum
4 years ago
5:37

PornHub

Sissy vibrator chastity cum

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Sissy hads free cum
5 years ago
0:41

PornHub

Sissy hads free cum

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Sissy strips off Matching Bra and Panties preview
3 years ago
1:09

PornHub

Sissy strips off Matching Bra and Panties preview

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Sissy Boi Anal Training by Goddess Lana
4 years ago
6:48

PornHub

Sissy Boi Anal Training by Goddess Lana

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Chastity Anal Orgasms With Huge Dildos Sissy Jessica Bloom
6 months ago
7:11

xHamster

Chastity Anal Orgasms With Huge Dildos Sissy Jessica Bloom

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Sissy cock worship
5 years ago
0:51

PornHub

Sissy cock worship

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LOAN4K. Lovely Blanche sucks dick and gets her sissy fucked for cash
4 years ago
9:55

PornHub

LOAN4K. Lovely Blanche sucks dick and gets her sissy fucked for cash

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SEX-POSITIVE SISSY DICKBLOWER #5
4 years ago
7:09

PornGem

SEX-POSITIVE SISSY DICKBLOWER #5

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Cute Caged Sissy Trap Crossdresser Ruins Orgasms and Cums Huge on Webcam (Full)
3 years ago
46:58

PornHub

Cute Caged Sissy Trap Crossdresser Ruins Orgasms and Cums Huge on Webcam (Full)

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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 sucks and gets fucked bareback
5 years ago
4:07

PornHub

Sissy sucks and gets fucked bareback

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The Pose Foot Tease Pantyhose Sissy cuck wife
3 years ago
0:30

PornHub

The Pose Foot Tease Pantyhose Sissy cuck wife

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Deep in his ass - sexy wife pegging her anal sissy slut in stockings
1 year ago
20:23

XXXDan

Deep in his ass - sexy wife pegging her anal sissy slut in stockings

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Hot blonde sissy cd milf cums from ass fucking then cumshot jerk
4 years ago
9:06

PornHub

Hot blonde sissy cd milf cums from ass fucking then cumshot jerk

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Juicy Lucy Sissy Splooshing For Goddess THICC British Booty
3 years ago
5:28

PornHub

Juicy Lucy Sissy Splooshing For Goddess THICC British Booty

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Crossdresser sissy getting fucked
9 months ago
2:59

JizzBunker

Crossdresser sissy getting fucked

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Sissy Lucy in Chastity with the Fucking Machine
3 years ago
12:22

PornHub

Sissy Lucy in Chastity with the Fucking Machine

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Dream come true for this sissy tied to bed post by a beautiful women
4 years ago
10:08

PornHub

Dream come true for this sissy tied to bed post by a beautiful women

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Frisky brunette Molly Manson gets fang in sissy
5 years ago
5:05

DrTuber

Frisky brunette Molly Manson gets fang in sissy

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Gothic sissy slut wants to sit on a big cock
3 years ago
1:58

PornHub

Gothic sissy slut wants to sit on a big cock

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BBW Dominatrix with sissy bitch
4 years ago
33:38

PornHub

BBW Dominatrix with sissy bitch

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Aunt sissy 1
1 year ago
15:02

XXXDan

Aunt sissy 1

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Sub sissy cross dresser
4 years ago
0:35

PornHub

Sub sissy cross dresser

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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 me takes plug out and gets BBC
4 years ago
1:08

PornHub

Sissy me takes plug out and gets BBC

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Daddy vs Sissy Slut
50 days ago
4:40

XXXDan

Daddy vs Sissy Slut

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Sissy anal training
5 years ago
0:57

PornHub

Sissy anal training

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CEI Sissy Training - Femdom POV Star Nine TRAILER
5 years ago
0:39

PornHub

CEI Sissy Training - Femdom POV Star Nine TRAILER

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sissy  couldn't resist to fuck her pussy trying new lingerie on TEASER
5 years ago
8:07

PornHub

sissy couldn't resist to fuck her pussy trying new lingerie on TEASER

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My Sissy Husbands Clit In Chastity
3 years ago
1:11

PornHub

My Sissy Husbands Clit In Chastity

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Sissy play
4 years ago
3:59

PornHub

Sissy play

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LADIES USE DUDES - Teen femdom strapon threesome with sissy pegging and jerking
3 months ago
5:00

JizzBunker

LADIES USE DUDES - Teen femdom strapon threesome with sissy pegging and jerking

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Sissy Slut Alice does a short striptease
5 years ago
1:56

PornHub

Sissy Slut Alice does a short striptease

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sissy blonde
6 years ago
4:51

JizzBunker

sissy blonde

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Bad Dragon toy makes sissy squirt during orgasm
3 years ago
14:50

PornHub

Bad Dragon toy makes sissy squirt during orgasm

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Deep throat training starting October 3, 2023 for my husband - training to be a good sissy
6 months ago
9:21

XXXDan

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3 years ago
2:26

PornHub

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4 years ago
1:38

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4 years ago
12:25

PornHub

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7 months ago
18:49

XXXDan

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4 years ago
0:28

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3 years ago
0:44

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1 year ago
10:46

JizzBunker

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5 years ago
19:03

uiPorn

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1 year ago
16:31

XXXDan

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3 years ago
0:39

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5 years ago
5:32

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1 year ago
12:22

JizzBunker

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5 years ago
2:32

PornHub

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4 years ago
1:32

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4 years ago
2:44

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2 years ago
10:07

XXXDan

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3 years ago
11:32

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1 year ago
12:45

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3 years ago
1:10

PornHub

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3 years ago
0:40

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52 days ago
3:08

xHamster

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3 years ago
0:24

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3 years ago
1:39

PornHub

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2 years ago
5:13

XXXDan

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2 years ago
8:53

XXXDan

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5 years ago
3:31

PornHub

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3 years ago
7:23

PornHub

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3 years ago
25:16

PornHub

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4 years ago
5:17

PornHub

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1 year ago
5:07

JizzBunker

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3 months ago
2:49

XXXDan

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3 years ago
3:48

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3 years ago
5:36

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3 years ago
6:25

PornHub

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4 years ago
30:29

PornHub

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3 years ago
6:29

PornHub

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3 years ago
1:43

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3 years ago
0:51

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1 year ago
4:10

JizzBunker

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