Sissy: 387 Videos

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

xHamster

Sissy Ray in Pink Sissy Dress (Twirling Upskirt)

Sissy Sissy in Chastity
3 years ago
3:21

xHamster

Sissy Sissy in Chastity

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

Tube8

Good Girl Good Sissy Hypno Sissy

sissy
2 years ago
2:18

xHamster

sissy

Sissy maker
5 years ago
3:54

PornHub

Sissy maker

Sissy Threesome
3 years ago
23:24

Tube8

Sissy Threesome

Sissy 3SUM
3 years ago
28:24

Tube8

Sissy 3SUM

Smoking Sissy
3 years ago
0:54

xHamster

Smoking Sissy

Sissy-Slut
10 months ago
0:26

xHamster

Sissy-Slut

Sissy Wedding
7 years ago
2:37

xHamster

Sissy Wedding

Sissy add2
5 years ago
5:00

xHamster

Sissy add2

Sissy Fucking
3 years ago
1:24:12

Tube8

Sissy Fucking

Mincing Sissy
11 months ago
1:44

PornHub

Mincing Sissy

Sissy Addiction
1 year ago
3:40

xHamster

Sissy Addiction

anyones sissy
6 years ago
2:37

Tube8

anyones sissy

Sissy amateur
1 year ago
0:06

PornHub

Sissy amateur

Sissy Musings
1 year ago
11:52

Tube8

Sissy Musings

sissy maid
8 years ago
5:46

xHamster

sissy maid

Sissy Toying
1 year ago
26:54

Tube8

Sissy Toying

sissy me
8 years ago
7:44

xHamster

sissy me

sissy gianakopoulou
9 years ago
6:26

xHamster

sissy gianakopoulou

Sissy Fuck
5 years ago
4:02

xHamster

Sissy Fuck

Sissy Struggles
4 years ago
5:04

xHamster

Sissy Struggles

Sissy Jana
6 months ago
1:47

xHamster

Sissy Jana

Sissy Training
4 years ago
14:41

xHamster

Sissy Training

Sissy bounce
8 months ago
0:12

xHamster

Sissy bounce

smoking sissy
3 years ago
5:40

PornHub

smoking sissy

Bimboization - Sissy
4 years ago
2:23

xHamster

Bimboization - Sissy

hairy SISSY
6 years ago
12:39

xHamster

hairy SISSY

sissy shelly
8 months ago
2:44

xHamster

sissy shelly

sissy domination
4 years ago
23:16

xHamster

sissy domination

sissy claire.
8 years ago
0:33

xHamster

sissy claire.

Sissy 6
7 years ago
1:54

xHamster

Sissy 6

Sissy Spank
7 years ago
4:02

xHamster

Sissy Spank

Latex Sissy Maid
4 years ago
1:42

xHamster

Latex Sissy Maid

Sissy Time 7
1 year ago
4:40

xHamster

Sissy Time 7

Sissy wets diaper
4 years ago
0:56

xHamster

Sissy wets diaper

Sissy in Leather
6 years ago
0:47

Tube8

Sissy in Leather

Sissy Hypno Fetish
1 year ago
2:19

PornHub

Sissy Hypno Fetish

Submissive Sissy Slut
1 year ago
2:56

PornHub

Submissive Sissy Slut

ASS SISSY DESTROYED
1 year ago
6:09

xHamster

ASS SISSY DESTROYED

Sissy Cumslut Trainer
4 years ago
9:50

xHamster

Sissy Cumslut Trainer

Sissy gets opened
6 years ago
5:47

xHamster

Sissy gets opened

tits sissy nikki
3 years ago
1:34

RedTube

tits sissy nikki

Sissy Punishing Herself
4 years ago
0:54

xHamster

Sissy Punishing Herself

Sissy serves man
4 years ago
14:23

xHamster

Sissy serves man

Anal Submission - Sissy
4 years ago
5:17

xHamster

Anal Submission - Sissy

sissy dildo fun
3 years ago
2:00

xHamster

sissy dildo fun

Sissy Maid Fuck
5 years ago
4:49

xHamster

Sissy Maid Fuck

Sissy Daddys stable
5 years ago
0:50

xHamster

Sissy Daddys stable

Sissy Blowjob Instructions
4 years ago
5:05

xHamster

Sissy Blowjob Instructions

Sissy Submission Training
4 years ago
12:38

Tube8

Sissy Submission Training

sissy boy fucking
5 years ago
15:09

xHamster

sissy boy fucking

Sissy Maker 3
3 years ago
6:48

Tube8

Sissy Maker 3

Kim and sissy
6 years ago
0:35

xHamster

Kim and sissy

sissy strap-on
6 years ago
3:59

xHamster

sissy strap-on

extreme anal sissy
7 years ago
3:57

xHamster

extreme anal sissy

Sissy Boy Anal
7 years ago
40:04

xHamster

Sissy Boy Anal

Shari Sissy Masturbation
7 years ago
4:37

xHamster

Shari Sissy Masturbation

Femdom - Sissy Boys
7 years ago
2:13

xHamster

Femdom - Sissy Boys

Sissy Stephie Jacks
9 months ago
1:39

xHamster

Sissy Stephie Jacks

Crossdreser sissy fucked
7 years ago
14:48

xHamster

Crossdreser sissy fucked

Sissy Wedding Night
7 years ago
2:59

xHamster

Sissy Wedding Night

Sissy Renate maulgefickt
1 year ago
4:21

xHamster

Sissy Renate maulgefickt

Sweet Sissy Fucking
7 months ago
4:39

xHamster

Sweet Sissy Fucking

Bareback Sissy Balletrocks
7 months ago
24:26

xHamster

Bareback Sissy Balletrocks

sissy looks hot
1 year ago
0:30

PornHub

sissy looks hot

Sissy Maid Gold
3 years ago
11:01

xHamster

Sissy Maid Gold

sissy babies diaper
8 years ago
1:08

xHamster

sissy babies diaper

Sissy maid fucked
6 years ago
24:12

Tube8

Sissy maid fucked

Dutch prossie rides sissy
6 months ago
10:10

GotPorn

Dutch prossie rides sissy

Punishing a Sissy Slut
7 years ago
5:37

xHamster

Punishing a Sissy Slut

Sissy Sweet Interracial Assfuck
6 years ago
15:11

Tube8

Sissy Sweet Interracial Assfuck

Mistress Dildos Sissy Slave
4 years ago
14:25

Tube8

Mistress Dildos Sissy Slave

Sissy Boy Foot Worship
5 years ago
6:06

DrTuber

Sissy Boy Foot Worship

Sissy Strokes and Cums
7 years ago
3:56

xHamster

Sissy Strokes and Cums

Sissy maid gets rammed
5 years ago
2:10

xHamster

Sissy maid gets rammed

tv sissy cocksucking slut
6 years ago
1:14

xHamster

tv sissy cocksucking slut

sissy cocksucking slave training
7 years ago
31:00

xHamster

sissy cocksucking slave training

Fat sissy outdoor #2
7 years ago
3:21

xHamster

Fat sissy outdoor #2

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

Tube8

Domination of a sissy

Mistress Dildos Sissy Slave
5 years ago
14:26

Tube8

Mistress Dildos Sissy Slave

Sissy in Action 001
3 years ago
30:35

Tube8

Sissy in Action 001

Sissy Anal Submission Training
5 years ago
5:17

xHamster

Sissy Anal Submission Training

smoking sissy slut chrissy
7 years ago
3:16

xHamster

smoking sissy slut chrissy

Robert jessop outted sissy
6 months ago
0:47

xHamster

Robert jessop outted sissy

Latex Sissy Maid Cuckolded
6 years ago
6:06

GotPorn

Latex Sissy Maid Cuckolded

Big v Sissy - London
1 year ago
4:52

DrTuber

Big v Sissy - London

Girls smothering sissy guys
3 months ago
5:00

GotPorn

Girls smothering sissy guys

michaels dirty sissy slut
7 years ago
3:18

xHamster

michaels dirty sissy slut

Sissy Training Crossdresser Humiliation
4 years ago
3:15

SunPorno

Sissy Training Crossdresser Humiliation

DianeL BBW Sissy Smoke
4 years ago
0:36

PornHub

DianeL BBW Sissy Smoke

sissy jerking off 3
5 years ago
1:00

xHamster

sissy jerking off 3

Vera fucking sissy hubby
4 years ago
2:58

PornHub

Vera fucking sissy hubby

Sissy deepthroating big dildo
3 years ago
2:54

PornHub

Sissy deepthroating big dildo

OMG you sissy fag
5 years ago
10:30

xHamster

OMG you sissy fag

Whit a sissy slut
6 years ago
0:59

xHamster

Whit a sissy slut

Sissy Hypno Cock Worship
2 years ago
4:21

PornHub

Sissy Hypno Cock Worship

Sissy Sexy Leather Doll
2 years ago
6:34

NuVid

Sissy Sexy Leather Doll

Sissy boy gets pampered
5 years ago
18:28

RedTube

Sissy boy gets pampered

hot sissy boy dildoing
5 years ago
7:29

xHamster

hot sissy boy dildoing

Mistresses fuck sissy ass
2 years ago
5:20

DrTuber

Mistresses fuck sissy ass

Anti Sissy Hypno 2
1 year ago
5:13

PornHub

Anti Sissy Hypno 2

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

xHamster

Fucking My Sissy Slave!!!

Clean My Toilet Sissy!
1 year ago
7:05

xHamster

Clean My Toilet Sissy!

SISSY LOVES TO PLEASE
4 years ago
6:24

Tube8

SISSY LOVES TO PLEASE

Sissy Faggot Humiliation Joi
1 year ago
7:16

PornHub

Sissy Faggot Humiliation Joi

Fat Sissy Video #4
8 years ago
1:08

xHamster

Fat Sissy Video #4

Your,e a Sissy
2 years ago
2:30

PornHub

Your,e a Sissy

My Sissy Dream 6
10 months ago
14:14

RedTube

My Sissy Dream 6

Mistress sissy boy Strapon
5 years ago
24:17

xHamster

Mistress sissy boy Strapon

Sissy Shemale Bimbo Transformer
3 years ago
17:04

xHamster

Sissy Shemale Bimbo Transformer

Mistress spanking useless sissy
5 years ago
5:30

Tube8

Mistress spanking useless sissy

Sissy sex in  panties
7 years ago
5:14

xHamster

Sissy sex in panties

Drinks that are Sissy
1 year ago
8:04

NuVid

Drinks that are Sissy

chastised  sissy fuck toys
7 years ago
6:41

xHamster

chastised sissy fuck toys

SISSY IN RED DRESS 4
1 year ago
0:50

DrTuber

SISSY IN RED DRESS 4

Being a Sissy in Diaper
1 year ago
2:20

NuVid

Being a Sissy in Diaper

Dominatrix babes pegging their sissy
3 years ago
6:14

DrTuber

Dominatrix babes pegging their sissy

sissy video 39 daddy daved
7 months ago
2:29

xHamster

sissy video 39 daddy daved

black cocks for sissy whores
4 years ago
4:08

xHamster

black cocks for sissy whores

Showing off as a sissy
1 year ago
5:46

PornHub

Showing off as a sissy

my soft sissy clit cumming
1 year ago
0:32

PornHub

my soft sissy clit cumming

sissy ts pen in sounding
1 year ago
16:32

xHamster

sissy ts pen in sounding

Sissy Hypno Dildo Poppers Trainer
2 years ago
14:00

PornHub

Sissy Hypno Dildo Poppers Trainer

Femdom wife dominates crossdressing sissy
2 years ago
6:06

DrTuber

Femdom wife dominates crossdressing sissy

Mr Bean Becomes a Sissy
11 months ago
3:32

PornHub

Mr Bean Becomes a Sissy

Bitch femdoms face sitting sissy
3 years ago
5:18

DrTuber

Bitch femdoms face sitting sissy

Kalina Dirty Smoking Sissy Whore
2 years ago
7:56

PornHub

Kalina Dirty Smoking Sissy Whore

Sissy at the Truck Stop
3 years ago
0:49

xHamster

Sissy at the Truck Stop

Spanked sissy movietures and paddling
10 months ago
7:02

RedTube

Spanked sissy movietures and paddling

Tranny and sissy sex partys
2 years ago
5:24

DrTuber

Tranny and sissy sex partys

I am a sissy boy
2 years ago
14:26

xHamster

I am a sissy boy

cute sissy boy fingering himself
4 years ago
3:38

xHamster

cute sissy boy fingering himself

sissy video 29 filling pritty
10 months ago
1:45

xHamster

sissy video 29 filling pritty

Sissy Faggot Pink Holder Smoke
2 years ago
1:43

PornHub

Sissy Faggot Pink Holder Smoke

SISSY CD GETTING FUCKED B2
2 years ago
6:51

PornHub

SISSY CD GETTING FUCKED B2

Mistress sissy to suck cock
4 years ago
2:52

xHamster

Mistress sissy to suck cock

sissy gf lacey and hrdblkdcknsd
3 years ago
0:32

xHamster

sissy gf lacey and hrdblkdcknsd

French redhead uses crossdressing sissy
2 years ago
30:48

xHamster

French redhead uses crossdressing sissy

Sissy Hubby Has Hot Wife
4 years ago
5:02

Tube8

Sissy Hubby Has Hot Wife

Redhead gives footjob to sissy
6 years ago
5:09

Tube8

Redhead gives footjob to sissy

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 sexy leather dress 2
5 years ago
1:13

xHamster

Sissy sexy leather dress 2

Sissy sexy in leather 5
5 years ago
0:47

xHamster

Sissy sexy in leather 5

Sissy sexy in leather 4
5 years ago
1:20

xHamster

Sissy sexy in leather 4

Domina mastering sissy and servant
5 years ago
5:05

DrTuber

Domina mastering sissy and servant

Sissy Hubby Watches Hot Wife
5 years ago
5:00

Tube8

Sissy Hubby Watches Hot Wife

Sissy gets to fuck mistress
5 years ago
31:10

xHamster

Sissy gets to fuck mistress

Sissy Boy Receives Anal Punishment
7 years ago
9:25

GotPorn

Sissy Boy Receives Anal Punishment

Sissy Chastity Slave Worships Feet
7 years ago
7:03

SunPorno

Sissy Chastity Slave Worships Feet

Mistress Handjob Sissy Chastity Tease
5 years ago
8:52

Tube8

Mistress Handjob Sissy Chastity Tease

Sissy Ray in White Panties
5 years ago
0:24

xHamster

Sissy Ray in White Panties

Sissy taking a large dildo
5 years ago
0:42

xHamster

Sissy taking a large dildo

Sissy Boy Strap On Hell
5 years ago
7:20

DrTuber

Sissy Boy Strap On Hell

Ass Fucking Her Male Sissy
8 years ago
9:39

GotPorn

Ass Fucking Her Male Sissy

Face Sitting On Sissy Boy
6 years ago
6:15

GotPorn

Face Sitting On Sissy Boy

Crossdresser gay sissy gets fucked
6 years ago
9:49

Tube8

Crossdresser gay sissy gets fucked

Strapon Butt Plug BDSM sissy
6 years ago
8:58

DrTuber

Strapon Butt Plug BDSM sissy

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 sexy leather girl 3
4 years ago
0:50

NuVid

Sissy sexy leather girl 3

Domina Strapon Fucks Sissy Boy
6 years ago
25:36

Tube8

Domina Strapon Fucks Sissy Boy

Femdom sissy slave torture session
5 years ago
31:04

RedTube

Femdom sissy slave torture session

Jon My sissy Great submissive bitch
1 year ago
2:48

xHamster

Jon My sissy Great submissive bitch

Mistress Fucking a Sissy in Pantyhose
2 years ago
10:00

PornHub

Mistress Fucking a Sissy in Pantyhose

No Cum For You Sissy Boy
6 years ago
5:48

Tube8

No Cum For You Sissy Boy

Sissy Ready in Sexy Leather 2
2 years ago
3:12

Tube8

Sissy Ready in Sexy Leather 2

Sissy sexy thigh high boots 2
4 years ago
3:31

xHamster

Sissy sexy thigh high boots 2

getting to know my inner sissy
3 years ago
0:19

PornHub

getting to know my inner sissy

Fuck and suck the crossdressing sissy
5 years ago
5:08

DrTuber

Fuck and suck the crossdressing sissy

Crossdressing sissy gets handjob during roleplay
6 years ago
5:01

GotPorn

Crossdressing sissy gets handjob during roleplay

sissy hubby spanked by femdom wife
3 years ago
0:53

xHamster

sissy hubby spanked by femdom wife

Hardcore sissy gays fucked movietures and
1 year ago
7:29

RedTube

Hardcore sissy gays fucked movietures and

Redhead workout suits and sissy handjob
1 year ago
7:00

RedTube

Redhead workout suits and sissy handjob

Shari a Sissy Maid Riding Dildo
7 years ago
1:11

xHamster

Shari a Sissy Maid Riding Dildo

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

xHamster

Sissy Ray in Red Taffeta Skirt

Stepmom and Dauther Pegging Sissy Boy
3 months ago
29:20

DrTuber

Stepmom and Dauther Pegging Sissy Boy

sissy faggot jamessub999 jerking off outside
2 years ago
0:29

PornHub

sissy faggot jamessub999 jerking off outside