Sissy: 881 Videos

Sissy boy at play
16 years ago
3:01

CrocoTube

Sissy boy at play

Nude Sexy Crossdresser Ass Hole Boobs Naked Fucking Hot Sissy Shemale Slave Submissive Booty Gangbang Blonde Girly Boy
2 years ago
3:00

xHamster

Nude Sexy Crossdresser Ass Hole Boobs Naked Fucking Hot Sissy Shemale Slave Submissive Booty Gangbang Blonde Girly Boy

SISSY IS ALWAYS HUNGRY FOR RAW COCK
1 year ago
3:00

XXXDan

SISSY IS ALWAYS HUNGRY FOR RAW COCK

skinny white sissy shemale fuck her huge pink dildo dirty and cum hard
2 years ago
3:00

xHamster

skinny white sissy shemale fuck her huge pink dildo dirty and cum hard

SISSY IS ALWAYS HUNGRY FOR RAW COCK
4 years ago
2:55

xHamster

SISSY IS ALWAYS HUNGRY FOR RAW COCK

Bubblegum Sissy V2.0
3 years ago
2:55

XXXDan

Bubblegum Sissy V2.0

My pig sissy
3 years ago
2:54

xHamster

My pig sissy

Mistress sissy to suck cock
11 years ago
2:52

xHamster

Mistress sissy to suck cock

Sexy Sissy Patricia having Fun with Dildo and Large Butt Plu
4 years ago
2:52

xHamster

Sexy Sissy Patricia having Fun with Dildo and Large Butt Plu

Playing with my bulge in a purple sissy satin thong
3 years ago
2:49

xHamster

Playing with my bulge in a purple sissy satin thong

Sissy Throat training
3 years ago
2:48

xHamster

Sissy Throat training

Tasty creampie in my sissy face (THX Mr. D for this gift)
4 years ago
2:47

xHamster

Tasty creampie in my sissy face (THX Mr. D for this gift)

Hot Sissy Brenda eats her cum
1 year ago
2:46

JizzBunker

Hot Sissy Brenda eats her cum

PVC Suit Inflatable tail Brown Fox Sissy Breathplay Hump
3 years ago
2:45

xHamster

PVC Suit Inflatable tail Brown Fox Sissy Breathplay Hump

BBC Stocky Top Fucks Candys Sissy Pussy and Cums Quick
5 years ago
2:44

xHamster

BBC Stocky Top Fucks Candys Sissy Pussy and Cums Quick

The Little Sissy Short Hair Nov
3 years ago
2:43

xHamster

The Little Sissy Short Hair Nov

SISSY IN PANTIES MASTURBATES LYING DOWN - UEKHUI
2 years ago
2:41

xHamster

SISSY IN PANTIES MASTURBATES LYING DOWN - UEKHUI

Handless cumshot cute lady boy cock between legs hot horny pretty shemale white smooth skin big ass big butt booty sissy
2 years ago
2:40

xHamster

Handless cumshot cute lady boy cock between legs hot horny pretty shemale white smooth skin big ass big butt booty sissy

Cristal Kinky playing with my latex sissy doll Preview
3 years ago
2:38

xHamster

Cristal Kinky playing with my latex sissy doll Preview

Sissy Wedding
14 years ago
2:37

xHamster

Sissy Wedding

New Sissy Lara White: Crazy anal slut craving cock and cum in mouth shaking booty to impress males. Crossdresser. Trans
3 years ago
2:37

xHamster

New Sissy Lara White: Crazy anal slut craving cock and cum in mouth shaking booty to impress males. Crossdresser. Trans

Sissy clit in pantyhose bikini
3 years ago
2:36

xHamster

Sissy clit in pantyhose bikini

entertain me more sissy boi
5 years ago
2:34

xHamster

entertain me more sissy boi

The Deep Sissy Anal 1
1 year ago
2:30

xHamster

The Deep Sissy Anal 1

SISSY IS ALWAYS HUNGRY FOR RAW COCK
4 years ago
2:29

xHamster

SISSY IS ALWAYS HUNGRY FOR RAW COCK

CD Sissy Angelina LeLapinou Fucking Her Creamy Ass Pussy with HUGE Dildo
2 years ago
2:27

xHamster

CD Sissy Angelina LeLapinou Fucking Her Creamy Ass Pussy with HUGE Dildo

Sissy fun slow motion
5 years ago
2:27

xHamster

Sissy fun slow motion

Sissy
1 year ago
2:23

XXXDan

Sissy

Sissy Elvi Lynx Sex Machine Analfuck - Preview
1 year ago
2:21

xHamster

Sissy Elvi Lynx Sex Machine Analfuck - Preview

Being a Sissy in Diaper
8 years ago
2:20

NuVid

Being a Sissy in Diaper

Sissy loves lots of cum - Split - BEN
9 years ago
2:20

xHamster

Sissy loves lots of cum - Split - BEN

Monster BBC Dildo penetrates an exploited Juicy Ass Belgian Sissy
3 years ago
2:19

xHamster

Monster BBC Dildo penetrates an exploited Juicy Ass Belgian Sissy

CD Sissy Fem Milf Mila Ferrari Solo Play
3 years ago
2:18

xHamster

CD Sissy Fem Milf Mila Ferrari Solo Play

Becuming Sissy Suck Edition
2 years ago
2:17

XXXDan

Becuming Sissy Suck Edition

Mistress Cassidy Slaps Sissy's Ass Till Its Red
1 year ago
2:16

xHamster

Mistress Cassidy Slaps Sissy's Ass Till Its Red

DominaFire Anal Training her Sissy
2 years ago
2:16

xHamster

DominaFire Anal Training her Sissy

Tiny Cock Sissy Fucked Hard
2 years ago
2:15

xHamster

Tiny Cock Sissy Fucked Hard

Submissive sissy having a dirty talk and changing clothes
1 year ago
2:15

xHamster

Submissive sissy having a dirty talk and changing clothes

Feminization, Makeup, Sissy Crossdressing for Your Step Dad
1 year ago
2:14

xHamster

Feminization, Makeup, Sissy Crossdressing for Your Step Dad

Sissy cum eating.
4 years ago
2:14

xHamster

Sissy cum eating.

Happy Christmas Sissy Slut
1 year ago
2:12

xHamster

Happy Christmas Sissy Slut

Anal Fisting Training for my Sissy Slut Petra! (DOMINAFIRE)
3 years ago
2:11

xHamster

Anal Fisting Training for my Sissy Slut Petra! (DOMINAFIRE)

Sissy gives blowjob
3 years ago
2:09

XXXDan

Sissy gives blowjob

Sissy-Kuroko Anal Plug
2 years ago
2:07

xHamster

Sissy-Kuroko Anal Plug

Naughty Sissy Self Spanking for Mistress
4 years ago
2:06

xHamster

Naughty Sissy Self Spanking for Mistress

Sissy-Kuroko Anal Huge Dildo Bodystocking
3 years ago
2:05

xHamster

Sissy-Kuroko Anal Huge Dildo Bodystocking

Tricked and Sissyfied two SISSY ORAL JOB
6 years ago
2:03

PornGem

Tricked and Sissyfied two SISSY ORAL JOB

Moaning sissy with cum
1 year ago
2:02

XXXDan

Moaning sissy with cum

Sexy sissy sucks black cock
1 year ago
2:02

XXXDan

Sexy sissy sucks black cock

SISSY WEARING WHITE PANTYHOSE JERKING OFF HIS HARD DICK - UEKHUI
2 years ago
2:02

xHamster

SISSY WEARING WHITE PANTYHOSE JERKING OFF HIS HARD DICK - UEKHUI

Sloppy deepthroat for bigblackcock by a sissy whore
3 years ago
2:02

xHamster

Sloppy deepthroat for bigblackcock by a sissy whore

sissy dildo fun
11 years ago
2:00

xHamster

sissy dildo fun

BBC Fuck Sissy Raw
6 years ago
2:00

xHamster

BBC Fuck Sissy Raw

White Sissy Shemale Gets Fucked
5 years ago
2:00

xHamster

White Sissy Shemale Gets Fucked

Sissy molly butt fucked by strapon wearing mistress BDSM porn
4 years ago
1:56

BDSMTubeOne

Sissy molly butt fucked by strapon wearing mistress BDSM porn

Uncut dilf fucks sissy slut on Valentines Day and cums for changing bitch POV preview
1 year ago
1:55

JizzBunker

Uncut dilf fucks sissy slut on Valentines Day and cums for changing bitch POV preview

Sissy Ray Shooting a load of sperm again (7 shots)
13 years ago
1:54

xHamster

Sissy Ray Shooting a load of sperm again (7 shots)

Sissy 6
15 years ago
1:54

xHamster

Sissy 6

Sissy Peehole training
4 years ago
1:54

xHamster

Sissy Peehole training

try new sissy fleshlight
3 years ago
1:53

xHamster

try new sissy fleshlight

Korean famous CD(sissy) Wooseure
4 years ago
1:51

xHamster

Korean famous CD(sissy) Wooseure

Sissy rachel solo dildo
4 years ago
1:49

xHamster

Sissy rachel solo dildo

Sneakers Pantyhose and Mini Skirt Crossdresser, Sissy
3 years ago
1:46

xHamster

Sneakers Pantyhose and Mini Skirt Crossdresser, Sissy

Fucking My Sissy Ass with a Fuck Machine and Big Dildos
1 year ago
1:46

xHamster

Fucking My Sissy Ass with a Fuck Machine and Big Dildos

Sissy-Kuroko Anal Dildo Bodystocking 1
3 years ago
1:45

xHamster

Sissy-Kuroko Anal Dildo Bodystocking 1

sissy video 29 filling pritty
8 years ago
1:45

xHamster

sissy video 29 filling pritty

Sissy cleaning lady filled with cum inside
3 years ago
1:44

xHamster

Sissy cleaning lady filled with cum inside

Chastity Sissy Twerking Ass For BBC Sex Doll
11 months ago
1:42

xHamster

Chastity Sissy Twerking Ass For BBC Sex Doll

LaurenFR - rubberdoll latexdoll rubber doll shemale trap sissy femboy crossdresser in full body latex catsuit show ass
3 years ago
1:42

xHamster

LaurenFR - rubberdoll latexdoll rubber doll shemale trap sissy femboy crossdresser in full body latex catsuit show ass

Sissy Stephie Jacks
8 years ago
1:39

xHamster

Sissy Stephie Jacks

Sissy crossdresser locked in chastity rides huge dildo
10 years ago
1:37

xHamster

Sissy crossdresser locked in chastity rides huge dildo

Sissy Crossdresser takes BBC Dildo in Hotel
11 years ago
1:37

xHamster

Sissy Crossdresser takes BBC Dildo in Hotel

I have so much fun teasing my sissy boy with my toes
12 years ago
1:37

xHamster

I have so much fun teasing my sissy boy with my toes

Sissy Selffacial Compilation
2 years ago
1:37

xHamster

Sissy Selffacial Compilation

sissy slut before going to a party
2 years ago
1:36

xHamster

sissy slut before going to a party

Sissy Cora Short Pump Plug Training
3 years ago
1:36

xHamster

Sissy Cora Short Pump Plug Training

naughty sissy spanking
7 years ago
1:35

xHamster

naughty sissy spanking

Fucking My Sissy Ass Big Gape and Cum
1 year ago
1:34

xHamster

Fucking My Sissy Ass Big Gape and Cum

Sissy in Cage Fucking Her Ass with Bot Toys
1 year ago
1:34

xHamster

Sissy in Cage Fucking Her Ass with Bot Toys

Chubby sissy furiously rubs her clitty till it spurts
3 years ago
1:31

xHamster

Chubby sissy furiously rubs her clitty till it spurts

Tranny MILF Rifnig Huge Toys and Cum Like a Sissy Slut
1 year ago
1:31

xHamster

Tranny MILF Rifnig Huge Toys and Cum Like a Sissy Slut

Sissy pleasure
2 years ago
1:28

xHamster

Sissy pleasure

Bitch boi husband made to ride and bouncing on my BBC and fed his own sissy cum
2 years ago
1:28

xHamster

Bitch boi husband made to ride and bouncing on my BBC and fed his own sissy cum

Sissy Fuck and Cum
3 years ago
1:28

xHamster

Sissy Fuck and Cum

Sissy Ray coming home from work
12 years ago
1:27

xHamster

Sissy Ray coming home from work

Unboxing sissy high heels platform
2 years ago
1:27

xHamster

Unboxing sissy high heels platform

Ashwini big ass sissy unseen clips and slides
2 years ago
1:26

xHamster

Ashwini big ass sissy unseen clips and slides

Pumping My Sissy Ass
1 year ago
1:26

xHamster

Pumping My Sissy Ass

sissy sarah breast enlarging training
3 years ago
1:26

xHamster

sissy sarah breast enlarging training

I Fucked Myself in a Sissy Dress
1 year ago
1:24

xHamster

I Fucked Myself in a Sissy Dress

Sissy in chastity love to ride toys
2 years ago
1:24

xHamster

Sissy in chastity love to ride toys

sissy sarah's clit
4 years ago
1:21

xHamster

sissy sarah's clit

Sissy ride dildo ass solo home
2 years ago
1:20

xHamster

Sissy ride dildo ass solo home

sissy faggot steven smoking like a slut
14 years ago
1:19

xHamster

sissy faggot steven smoking like a slut

Sissy Cock Toyed & Leaking
3 years ago
1:19

xHamster

Sissy Cock Toyed & Leaking

Gorgeous  solo Sissy foot fuck  masturbating
1 year ago
1:17

xHamster

Gorgeous solo Sissy foot fuck masturbating

Sissy Ray outdoors on windy day gold dress
12 years ago
1:16

xHamster

Sissy Ray outdoors on windy day gold dress

Sissy Joslin quick fuck with my dildo
3 years ago
1:16

xHamster

Sissy Joslin quick fuck with my dildo

Sissy with catheter and estim cum
2 years ago
1:14

xHamster

Sissy with catheter and estim cum

REAL SISSY TRAINING BY A REAL BBC MASTER
3 years ago
1:13

xHamster

REAL SISSY TRAINING BY A REAL BBC MASTER

sissy slut as her cock tossed of by bbw milf
8 years ago
1:12

xHamster

sissy slut as her cock tossed of by bbw milf

Showing Off My Asian Sissy Ass
4 years ago
1:11

xHamster

Showing Off My Asian Sissy Ass

Sissy POV follow me around like a good boy.
3 years ago
1:11

xHamster

Sissy POV follow me around like a good boy.

Sissy Dildo QUEEN - CD Tranny Ashley Whimpers
3 years ago
1:09

xHamster

Sissy Dildo QUEEN - CD Tranny Ashley Whimpers

caged sissy aisha jumps on dildo
2 years ago
1:09

xHamster

caged sissy aisha jumps on dildo

Fat Sissy Video #4
16 years ago
1:08

xHamster

Fat Sissy Video #4

sissy babies diaper
16 years ago
1:08

xHamster

sissy babies diaper

SISSY LYING DOWN WEARING A BIKINI MASTURBATING - UEKHUI
2 years ago
1:08

xHamster

SISSY LYING DOWN WEARING A BIKINI MASTURBATING - UEKHUI

Sissy Hair Salon Adventures Episode 1
1 year ago
1:08

xHamster

Sissy Hair Salon Adventures Episode 1

Public Sissy in Lingerie walking near busy highway.
2 years ago
1:08

xHamster

Public Sissy in Lingerie walking near busy highway.

One minute sissy kitchen fun
2 years ago
1:06

xHamster

One minute sissy kitchen fun

Sissy slut takes another raw cock
4 years ago
1:06

xHamster

Sissy slut takes another raw cock

SISSY PLAYING WITH HIS COCK SHOWING HIS FOOT - UEKHUI
2 years ago
1:04

xHamster

SISSY PLAYING WITH HIS COCK SHOWING HIS FOOT - UEKHUI

Anal machine chastity sissy
4 years ago
1:03

xHamster

Anal machine chastity sissy

Watch sexy sissy shemale shoot after edging for hours
2 years ago
1:02

xHamster

Watch sexy sissy shemale shoot after edging for hours

SISSY IS ALWAYS HUNGRY FOR RAW COCK
3 years ago
1:02

xHamster

SISSY IS ALWAYS HUNGRY FOR RAW COCK

Sissy bound, ass fucked and BJ
11 years ago
1:01

xHamster

Sissy bound, ass fucked and BJ

sissy jerking off 3
12 years ago
1:00

xHamster

sissy jerking off 3

SISSY WANKING WEARING MIXED STOCKINGS - UEKHUI
2 years ago
1:00

xHamster

SISSY WANKING WEARING MIXED STOCKINGS - UEKHUI

Sissy bitch boi dressed in fishnets and pegged with mistress's big strapon
2 years ago
0:59

xHamster

Sissy bitch boi dressed in fishnets and pegged with mistress's big strapon

SISSY BITCH FUCKING BIG TOYS SLUT
5 years ago
0:58

xHamster

SISSY BITCH FUCKING BIG TOYS SLUT

sissy sex
8 years ago
0:56

xHamster

sissy sex

Sissy Caption - Would you let a stranger fuck your ass raw?
4 years ago
0:55

xHamster

Sissy Caption - Would you let a stranger fuck your ass raw?

Fucking My Sissy Slave!!!
9 years ago
0:54

xHamster

Fucking My Sissy Slave!!!

Blonde Sissy Ana Keel Teasing Her Smooth Shaved Clitty
3 years ago
0:54

xHamster

Blonde Sissy Ana Keel Teasing Her Smooth Shaved Clitty

Sissy slut 4 dom daddy's
3 years ago
0:53

xHamster

Sissy slut 4 dom daddy's

german Sissy slaps
3 years ago
0:52

xHamster

german Sissy slaps

sissy sex
8 years ago
0:52

xHamster

sissy sex

Training my sissy whores Natasha.
5 years ago
0:51

xHamster

Training my sissy whores Natasha.

Sissy Daddys stable
13 years ago
0:50

xHamster

Sissy Daddys stable

Sissy sexy leather girl 3
12 years ago
0:50

NuVid

Sissy sexy leather girl 3

Accidentally sissy handsfree cumshot, soft penis nipple play
4 years ago
0:49

xHamster

Accidentally sissy handsfree cumshot, soft penis nipple play

Sissy Cum Riding Dildo and Dressed in White Cheerleader Dress
1 year ago
0:49

xHamster

Sissy Cum Riding Dildo and Dressed in White Cheerleader Dress

Cute Latex Sissy Locked In Negative Chastity Cage
2 years ago
0:48

xHamster

Cute Latex Sissy Locked In Negative Chastity Cage

SISSY TRAP - ANAL PLUG GAPE
3 years ago
0:46

xHamster

SISSY TRAP - ANAL PLUG GAPE

Sissy bottle fuck
6 years ago
0:46

xHamster

Sissy bottle fuck

Sissy Ray in Red Taffeta Dress in hotel room
11 years ago
0:45

xHamster

Sissy Ray in Red Taffeta Dress in hotel room

Sissy presenting herself
4 years ago
0:43

xHamster

Sissy presenting herself

fun with dave the sissy
6 years ago
0:41

xHamster

fun with dave the sissy

Asian Sissy horny and in desperate need of some REAL dick...
4 years ago
0:40

xHamster

Asian Sissy horny and in desperate need of some REAL dick...

Sissy Ray in Red Taffeta Skirt
12 years ago
0:39

xHamster

Sissy Ray in Red Taffeta Skirt

Sissy feet and cum
5 years ago
0:39

xHamster

Sissy feet and cum

Sissy Francis Malice Second New Face
1 year ago
0:39

xHamster

Sissy Francis Malice Second New Face

Shaking my sissy ass
3 years ago
0:38

xHamster

Shaking my sissy ass

Kim and sissy
14 years ago
0:35

xHamster

Kim and sissy

sissy claire.
16 years ago
0:33

xHamster

sissy claire.

sissy 1
6 years ago
0:33

xHamster

sissy 1

Sissy Joyce got fucked by a BBC
2 years ago
0:32

xHamster

Sissy Joyce got fucked by a BBC

Panty sissy twink shows his little boner.
5 years ago
0:32

xHamster

Panty sissy twink shows his little boner.

Hot Alternative Sissy Fucked
2 years ago
0:30

xHamster

Hot Alternative Sissy Fucked

sissy fleshlight jerking cum on stocking
3 years ago
0:27

xHamster

sissy fleshlight jerking cum on stocking

Shiny Satin Sissy 4k
6 years ago
0:24

xHamster

Shiny Satin Sissy 4k

my new pvc sissy dress
3 years ago
0:20

xHamster

my new pvc sissy dress

Anal sissy
1 year ago
0:20

xHamster

Anal sissy

Sissy feels cum inside her for the first time
3 years ago
0:14

xHamster

Sissy feels cum inside her for the first time

Lacy pantyboi sissy on kik 3
5 years ago
0:14

xHamster

Lacy pantyboi sissy on kik 3

Sissy bounce
8 years ago
0:12

xHamster

Sissy bounce

Sissy ruby
4 years ago
0:11

xHamster

Sissy ruby

Ruining my sissy cunt with two dildos
8 years ago
0:08

xHamster

Ruining my sissy cunt with two dildos

My Collection Gay or Sissy or Tranny 013
4 years ago
0:08

xHamster

My Collection Gay or Sissy or Tranny 013

Sissy Slut Plus Piggy Training His Daily Diet 1
3 years ago
0:08

xHamster

Sissy Slut Plus Piggy Training His Daily Diet 1