Sissy: 401 Videos

Sissy Ray in Pink Sissy Dress (Twirling Upskirt)
2 years ago
1:39

xHamster

Sissy Ray in Pink Sissy Dress (Twirling Upskirt)

Sissy Sissy in Chastity
2 years ago
3:21

xHamster

Sissy Sissy in Chastity

Good Girl Good Sissy Hypno Sissy
3 years ago
7:30

Tube8

Good Girl Good Sissy Hypno Sissy

Sissy
8 years ago
5:00

GotPorn

Sissy

sissy
2 years ago
2:18

xHamster

sissy

Smoking Sissy
3 years ago
0:54

xHamster

Smoking Sissy

Sissy 6
6 years ago
1:54

xHamster

Sissy 6

anyones sissy
5 years ago
2:37

Tube8

anyones sissy

sissy domination
3 years ago
23:16

xHamster

sissy domination

Sissy Fucking
3 years ago
1:24:12

Tube8

Sissy Fucking

Sissy Wedding
6 years ago
2:37

xHamster

Sissy Wedding

good sissy
3 years ago
0:16

xHamster

good sissy

smoking sissy
3 years ago
5:40

PornHub

smoking sissy

Sissy Addiction
4 months ago
3:40

xHamster

Sissy Addiction

Sissy 3SUM
3 years ago
28:24

Tube8

Sissy 3SUM

sissy maid
7 years ago
5:46

xHamster

sissy maid

Sissy Fuck
4 years ago
4:02

xHamster

Sissy Fuck

Mincing Sissy
3 months ago
1:44

PornHub

Mincing Sissy

Sissy amateur
5 months ago
0:06

PornHub

Sissy amateur

sissy gianakopoulou
8 years ago
6:26

xHamster

sissy gianakopoulou

Sissy Crossdresser
3 months ago
4:12

xHamster

Sissy Crossdresser

Sissy Threesome
3 years ago
23:24

Tube8

Sissy Threesome

Sissy Struggles
3 years ago
5:04

xHamster

Sissy Struggles

sissy me
7 years ago
7:44

xHamster

sissy me

Sissy add2
4 years ago
5:00

xHamster

Sissy add2

sissy claire.
7 years ago
0:33

xHamster

sissy claire.

Sissy Training
4 years ago
14:41

xHamster

Sissy Training

Sissy Musings
1 year ago
11:52

Tube8

Sissy Musings

Sissy bounce
4 days ago
0:12

xHamster

Sissy bounce

Sissy maker
4 years ago
3:54

PornHub

Sissy maker

Sissy Toying
1 year ago
26:54

Tube8

Sissy Toying

Bimboization - Sissy
3 years ago
2:23

xHamster

Bimboization - Sissy

Sissy-Slut
2 months ago
0:26

xHamster

Sissy-Slut

sissy shelly
5 days ago
2:44

xHamster

sissy shelly

Sissy Spank
6 years ago
4:02

xHamster

Sissy Spank

hairy SISSY
6 years ago
12:39

xHamster

hairy SISSY

Sissy Daddys stable
5 years ago
0:50

xHamster

Sissy Daddys stable

Sissy Maker 3
2 years ago
6:48

Tube8

Sissy Maker 3

Sissy Gets Fucked
5 months ago
0:16

xHamster

Sissy Gets Fucked

Sissy gets pegged
4 months ago
4:31

xHamster

Sissy gets pegged

Sissy gets opened
5 years ago
5:47

xHamster

Sissy gets opened

Kim and sissy
5 years ago
0:35

xHamster

Kim and sissy

Sissy Hypno Fetish
11 months ago
2:19

PornHub

Sissy Hypno Fetish

sissy boy fucking
5 years ago
15:09

xHamster

sissy boy fucking

sissy dildo fun
2 years ago
2:00

xHamster

sissy dildo fun

Submissive Sissy Slut
10 months ago
2:56

PornHub

Submissive Sissy Slut

Sissy Time 7
9 months ago
4:40

xHamster

Sissy Time 7

Sissy Stair Struggle
6 months ago
27:27

PornHub

Sissy Stair Struggle

sissy looks hot
6 months ago
0:30

PornHub

sissy looks hot

Sissy in Leather
5 years ago
0:47

Tube8

Sissy in Leather

Sissy Maid Gold
2 years ago
11:01

xHamster

Sissy Maid Gold

ASS SISSY DESTROYED
11 months ago
6:09

xHamster

ASS SISSY DESTROYED

Sissy Maid Fuck
4 years ago
4:49

xHamster

Sissy Maid Fuck

Sissy maid fucked
6 years ago
24:12

Tube8

Sissy maid fucked

Sissy Submission Training
3 years ago
12:38

Tube8

Sissy Submission Training

Crossdreser sissy fucked
6 years ago
14:48

xHamster

Crossdreser sissy fucked

Sissy Cumslut Trainer
3 years ago
9:50

xHamster

Sissy Cumslut Trainer

Sissy Wedding Night
6 years ago
2:59

xHamster

Sissy Wedding Night

Sissy Punishing Herself
3 years ago
0:54

xHamster

Sissy Punishing Herself

Sissy Stephie Jacks
37 days ago
1:39

xHamster

Sissy Stephie Jacks

Sissy wets diaper
4 years ago
0:56

xHamster

Sissy wets diaper

Sissy Blowjob Instructions
3 years ago
5:05

xHamster

Sissy Blowjob Instructions

Femdom - Sissy Boys
6 years ago
2:13

xHamster

Femdom - Sissy Boys

Shari Sissy Masturbation
6 years ago
4:37

xHamster

Shari Sissy Masturbation

Sissy strokes again
2 months ago
6:35

xHamster

Sissy strokes again

sissy strap-on
5 years ago
3:59

xHamster

sissy strap-on

Sissy Dance 2
20 days ago
1:34

xHamster

Sissy Dance 2

Sissy piss play
2 months ago
5:36

xHamster

Sissy piss play

sissy babies diaper
7 years ago
1:08

xHamster

sissy babies diaper

Latex Sissy Maid
4 years ago
1:42

xHamster

Latex Sissy Maid

Sissy serves man
4 years ago
14:23

xHamster

Sissy serves man

Sissy Renate maulgefickt
10 months ago
4:21

xHamster

Sissy Renate maulgefickt

extreme anal sissy
7 years ago
3:57

xHamster

extreme anal sissy

Anal Submission - Sissy
3 years ago
5:17

xHamster

Anal Submission - Sissy

Sissy Boy Anal
7 years ago
40:04

xHamster

Sissy Boy Anal

Sissy slut masturbates
2 months ago
1:08

xHamster

Sissy slut masturbates

tits sissy nikki
3 years ago
1:34

RedTube

tits sissy nikki

Sissy maid gets rammed
4 years ago
2:10

xHamster

Sissy maid gets rammed

Sissy Hypno Cock Worship
1 year ago
4:21

PornHub

Sissy Hypno Cock Worship

OMG you sissy fag
4 years ago
10:30

xHamster

OMG you sissy fag

Your,e a Sissy
2 years ago
2:30

PornHub

Your,e a Sissy

Sissy Boy Foot Worship
4 years ago
6:06

DrTuber

Sissy Boy Foot Worship

Mistress Dildos Sissy Slave
4 years ago
14:26

Tube8

Mistress Dildos Sissy Slave

Sissy Sexy Leather Doll
1 year ago
6:34

NuVid

Sissy Sexy Leather Doll

Vera fucking sissy hubby
3 years ago
2:58

PornHub

Vera fucking sissy hubby

Sissy Anal Submission Training
4 years ago
5:17

xHamster

Sissy Anal Submission Training

Sissy deepthroating big dildo
3 years ago
2:54

PornHub

Sissy deepthroating big dildo

Domination of a sissy
3 years ago
1:27:15

Tube8

Domination of a sissy

DianeL BBW Sissy Smoke
3 years ago
0:36

PornHub

DianeL BBW Sissy Smoke

sissy jerking off 3
4 years ago
1:00

xHamster

sissy jerking off 3

Sissy Training Crossdresser Humiliation
3 years ago
3:15

SunPorno

Sissy Training Crossdresser Humiliation

SISSY LOVES TO PLEASE
4 years ago
6:24

Tube8

SISSY LOVES TO PLEASE

Sissy Shemale Bimbo Transformer
2 years ago
17:04

xHamster

Sissy Shemale Bimbo Transformer

Mistress Dildos Sissy Slave
4 years ago
14:25

Tube8

Mistress Dildos Sissy Slave

Sissy in Action 001
3 years ago
30:35

Tube8

Sissy in Action 001

Sissy boy gets pampered
5 years ago
18:28

RedTube

Sissy boy gets pampered

Sissy Addiction 2 - SissyHypnoz
11 months ago
3:53

SunPorno

Sissy Addiction 2 - SissyHypnoz

chastised  sissy fuck toys
6 years ago
6:41

xHamster

chastised sissy fuck toys

Big v Sissy - London
5 months ago
4:52

DrTuber

Big v Sissy - London

Male sissy sucks cock.
4 months ago
3:29

xHamster

Male sissy sucks cock.

michaels dirty sissy slut
6 years ago
3:18

xHamster

michaels dirty sissy slut

Anti Sissy Hypno 2
5 months ago
5:13

PornHub

Anti Sissy Hypno 2

Whit a sissy slut
5 years ago
0:59

xHamster

Whit a sissy slut

Fat Sissy Video #4
7 years ago
1:08

xHamster

Fat Sissy Video #4

Punishing a Sissy Slut
6 years ago
5:37

xHamster

Punishing a Sissy Slut

Drinks that are Sissy
4 months ago
8:04

NuVid

Drinks that are Sissy

My Sissy Dream 6
2 months ago
14:14

RedTube

My Sissy Dream 6

Sissy sex in  panties
7 years ago
5:14

xHamster

Sissy sex in panties

Sissy Strokes and Cums
6 years ago
3:56

xHamster

Sissy Strokes and Cums

huge cock sissy slut
3 months ago
2:15

xHamster

huge cock sissy slut

sissy cocksucking slave training
6 years ago
31:00

xHamster

sissy cocksucking slave training

smoking sissy slut chrissy
6 years ago
3:16

xHamster

smoking sissy slut chrissy

Latex Sissy Maid Cuckolded
6 years ago
6:06

GotPorn

Latex Sissy Maid Cuckolded

Sissy Faggot Humiliation Joi
1 year ago
7:16

PornHub

Sissy Faggot Humiliation Joi

Mistress sissy boy Strapon
4 years ago
24:17

xHamster

Mistress sissy boy Strapon

Sissy Sweet Interracial Assfuck
6 years ago
15:11

Tube8

Sissy Sweet Interracial Assfuck

Mistress spanking useless sissy
4 years ago
5:30

Tube8

Mistress spanking useless sissy

tv sissy cocksucking slut
6 years ago
1:14

xHamster

tv sissy cocksucking slut

Fat sissy outdoor #2
6 years ago
3:21

xHamster

Fat sissy outdoor #2

Mistresses fuck sissy ass
1 year ago
5:20

DrTuber

Mistresses fuck sissy ass

sissy shelly pvc dress
40 days ago
1:50

xHamster

sissy shelly pvc dress

Fucking My Sissy Slave!!!
1 year ago
0:54

xHamster

Fucking My Sissy Slave!!!

hot sissy boy dildoing
5 years ago
7:29

xHamster

hot sissy boy dildoing

Clean My Toilet Sissy!
1 year ago
7:05

xHamster

Clean My Toilet Sissy!

Cumming French Maid Sissy
54 days ago
11:02

xHamster

Cumming French Maid Sissy

Sissy at the Truck Stop
3 years ago
0:49

xHamster

Sissy at the Truck Stop

Femboy Sissy Playing with Dildo
29 days ago
2:01

xHamster

Femboy Sissy Playing with Dildo

Sissy teen flashing the highway
31 days ago
2:36

xHamster

Sissy teen flashing the highway

Mistress sissy to suck cock
3 years ago
2:52

xHamster

Mistress sissy to suck cock

Sissy Hypno Dildo Poppers Trainer
1 year ago
14:00

PornHub

Sissy Hypno Dildo Poppers Trainer

sissy video 29 filling pritty
2 months ago
1:45

xHamster

sissy video 29 filling pritty

Spanked sissy movietures and paddling
2 months ago
7:02

RedTube

Spanked sissy movietures and paddling

Sissy Hubby Has Hot Wife
3 years ago
5:02

Tube8

Sissy Hubby Has Hot Wife

cute sissy boy fingering himself
3 years ago
3:38

xHamster

cute sissy boy fingering himself

Sissy doing Ass to mouth
2 months ago
3:22

xHamster

Sissy doing Ass to mouth

Sissy Faggot Pink Holder Smoke
1 year ago
1:43

PornHub

Sissy Faggot Pink Holder Smoke

SISSY CD GETTING FUCKED B2
1 year ago
6:51

PornHub

SISSY CD GETTING FUCKED B2

Femdom wife dominates crossdressing sissy
2 years ago
6:06

DrTuber

Femdom wife dominates crossdressing sissy

French redhead uses crossdressing sissy
1 year ago
30:48

xHamster

French redhead uses crossdressing sissy

I am a sissy boy
1 year ago
14:26

xHamster

I am a sissy boy

my soft sissy clit cumming
1 year ago
0:32

PornHub

my soft sissy clit cumming

Kalina Dirty Smoking Sissy Whore
1 year ago
7:56

PornHub

Kalina Dirty Smoking Sissy Whore

Dominatrix babes pegging their sissy
2 years ago
6:14

DrTuber

Dominatrix babes pegging their sissy

sissy ts pen in sounding
1 year ago
16:32

xHamster

sissy ts pen in sounding

shemale sissy sounding in urethral
10 months ago
2:39

PornHub

shemale sissy sounding in urethral

Being a Sissy in Diaper
5 months ago
2:20

NuVid

Being a Sissy in Diaper

SISSY IN RED DRESS 4
5 months ago
0:50

DrTuber

SISSY IN RED DRESS 4

Strapon babes pegging sissy guy
4 years ago
5:07

PornHub

Strapon babes pegging sissy guy

Showing off as a sissy
5 months ago
5:46

PornHub

Showing off as a sissy

Bitch femdoms face sitting sissy
3 years ago
5:18

DrTuber

Bitch femdoms face sitting sissy

Mr Bean Becomes a Sissy
3 months ago
3:32

PornHub

Mr Bean Becomes a Sissy

sissy gf lacey and hrdblkdcknsd
3 years ago
0:32

xHamster

sissy gf lacey and hrdblkdcknsd

Tranny and sissy sex partys
1 year ago
5:24

DrTuber

Tranny and sissy sex partys

Crossdresser gay sissy gets fucked
5 years ago
9:49

Tube8

Crossdresser gay sissy gets fucked

sissy dildo fucking in chastity
4 years ago
3:39

xHamster

sissy dildo fucking in chastity

Sissy sexy leather catsuit 1
4 years ago
3:17

xHamster

Sissy sexy leather catsuit 1

Sissy gets to fuck mistress
4 years ago
31:10

xHamster

Sissy gets to fuck mistress

Mistress Handjob Sissy Chastity Tease
5 years ago
8:52

Tube8

Mistress Handjob Sissy Chastity Tease

Sissy Boy Receives Anal Punishment
6 years ago
9:25

GotPorn

Sissy Boy Receives Anal Punishment

Sissy sexy leather outfit 1
4 years ago
1:04

xHamster

Sissy sexy leather outfit 1

Sissy Buttplgug Jerk and Cum
4 years ago
3:18

xHamster

Sissy Buttplgug Jerk and Cum

Sissy Chastity Slave Worships Feet
7 years ago
7:03

SunPorno

Sissy Chastity Slave Worships Feet

Sissy Hubby Watches Hot Wife
4 years ago
5:00

Tube8

Sissy Hubby Watches Hot Wife

Femdom sissy slave torture session
4 years ago
31:04

RedTube

Femdom sissy slave torture session

Domina Strapon Fucks Sissy Boy
6 years ago
25:36

Tube8

Domina Strapon Fucks Sissy Boy

Sissy sexy leather dress 2
4 years ago
1:13

xHamster

Sissy sexy leather dress 2

Domina mastering sissy and servant
4 years ago
5:05

DrTuber

Domina mastering sissy and servant

Sissy sexy in leather 4
4 years ago
1:20

xHamster

Sissy sexy in leather 4

Strapon Butt Plug BDSM sissy
6 years ago
8:58

DrTuber

Strapon Butt Plug BDSM sissy

White sissy cuckold trainer - mix
3 years ago
10:17

xHamster

White sissy cuckold trainer - mix

Face Sitting On Sissy Boy
5 years ago
6:15

GotPorn

Face Sitting On Sissy Boy

black cocks for sissy whores
3 years ago
4:08

xHamster

black cocks for sissy whores

Sissy Boy Strap On Hell
5 years ago
7:20

DrTuber

Sissy Boy Strap On Hell

Redhead gives footjob to sissy
5 years ago
5:09

Tube8

Redhead gives footjob to sissy

Sissy sexy leather girl 3
4 years ago
0:50

NuVid

Sissy sexy leather girl 3

Sissy taking a large dildo
5 years ago
0:42

xHamster

Sissy taking a large dildo

Ass Fucking Her Male Sissy
7 years ago
9:39

GotPorn

Ass Fucking Her Male Sissy

Sissy sexy in leather 5
4 years ago
0:47

xHamster

Sissy sexy in leather 5

Sissy Ray in White Panties
5 years ago
0:24

xHamster

Sissy Ray in White Panties

Sissy Shawna Toys for Goddess DiscreteSweetness
9 months ago
7:58

PornHub

Sissy Shawna Toys for Goddess DiscreteSweetness