Sissy: 391 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

anyones sissy
5 years ago
2:37

Tube8

anyones sissy

Smoking Sissy
3 years ago
0:54

xHamster

Smoking Sissy

sissy domination
3 years ago
23:16

xHamster

sissy domination

Sissy Training
3 years ago
14:41

xHamster

Sissy Training

Sissy maker
4 years ago
3:54

PornHub

Sissy maker

Sissy Wedding
6 years ago
2:37

xHamster

Sissy Wedding

Sissy Musings
1 year ago
11:52

Tube8

Sissy Musings

Sissy 6
6 years ago
1:54

xHamster

Sissy 6

Sissy amateur
4 months ago
0:06

PornHub

Sissy amateur

sissy me
7 years ago
7:44

xHamster

sissy me

sissy gianakopoulou
8 years ago
6:26

xHamster

sissy gianakopoulou

Sissy Struggles
3 years ago
5:04

xHamster

Sissy Struggles

Sissy 3SUM
3 years ago
28:24

Tube8

Sissy 3SUM

sissy maid
7 years ago
5:46

xHamster

sissy maid

Mincing Sissy
2 months ago
1:44

PornHub

Mincing Sissy

Sissy Crossdresser
2 months ago
4:12

xHamster

Sissy Crossdresser

Sissy Addiction
3 months ago
3:40

xHamster

Sissy Addiction

Bimboization - Sissy
3 years ago
2:23

xHamster

Bimboization - Sissy

Sissy Toying
1 year ago
26:54

Tube8

Sissy Toying

sissy claire.
7 years ago
0:33

xHamster

sissy claire.

Sissy add2
4 years ago
5:00

xHamster

Sissy add2

smoking sissy
2 years ago
5:40

PornHub

smoking sissy

good sissy
3 years ago
0:16

xHamster

good sissy

Sissy Fuck
4 years ago
4:02

xHamster

Sissy Fuck

Sissy Fucking
3 years ago
1:24:12

Tube8

Sissy Fucking

House Sissy
6 years ago
6:26

xHamster

House Sissy

Sissy Spank
6 years ago
4:02

xHamster

Sissy Spank

Sissy Threesome
3 years ago
23:24

Tube8

Sissy Threesome

hairy SISSY
5 years ago
12:39

xHamster

hairy SISSY

sissy fucking
42 days ago
1:53

xHamster

sissy fucking

Sissy-Slut
42 days ago
0:26

xHamster

Sissy-Slut

Submissive Sissy Slut
9 months ago
2:56

PornHub

Submissive Sissy Slut

Sissy gets pegged
3 months ago
4:31

xHamster

Sissy gets pegged

Kim and sissy
5 years ago
0:35

xHamster

Kim and sissy

Sissy Renate maulgefickt
9 months ago
4:21

xHamster

Sissy Renate maulgefickt

Sissy Hypno Fetish
10 months ago
2:19

PornHub

Sissy Hypno Fetish

Latex Sissy Maid
3 years ago
1:42

xHamster

Latex Sissy Maid

Sissy Time 7
7 months ago
4:40

xHamster

Sissy Time 7

Sissy Stair Struggle
5 months ago
27:27

PornHub

Sissy Stair Struggle

sissy looks hot
4 months ago
0:30

PornHub

sissy looks hot

Sissy gets opened
5 years ago
5:47

xHamster

Sissy gets opened

Sissy Maid Fuck
4 years ago
4:49

xHamster

Sissy Maid Fuck

sissy boy fucking
4 years ago
15:09

xHamster

sissy boy fucking

Sissy wets diaper
3 years ago
0:56

xHamster

Sissy wets diaper

Sissy in Leather
5 years ago
0:47

Tube8

Sissy in Leather

Sissy Gets Fucked
4 months ago
0:16

xHamster

Sissy Gets Fucked

Sissy Daddys stable
4 years ago
0:50

xHamster

Sissy Daddys stable

Sissy serves man
4 years ago
14:23

xHamster

Sissy serves man

Sissy strokes again
29 days ago
6:35

xHamster

Sissy strokes again

Sissy slut masturbates
51 days ago
1:08

xHamster

Sissy slut masturbates

Crossdreser sissy fucked
6 years ago
14:48

xHamster

Crossdreser sissy fucked

sissy strap-on
5 years ago
3:59

xHamster

sissy strap-on

Sissy Maid Gold
2 years ago
11:01

xHamster

Sissy Maid Gold

Sissy piss play
50 days ago
5:36

xHamster

Sissy piss play

Sissy Wedding Night
6 years ago
2:59

xHamster

Sissy Wedding Night

Femdom - Sissy Boys
6 years ago
2:13

xHamster

Femdom - Sissy Boys

Shari Sissy Masturbation
6 years ago
4:37

xHamster

Shari Sissy Masturbation

ASS SISSY DESTROYED
10 months ago
6:09

xHamster

ASS SISSY DESTROYED

sissy dildo fun
2 years ago
2:00

xHamster

sissy dildo fun

tits sissy nikki
3 years ago
1:34

RedTube

tits sissy nikki

Sissy Stephie Jacks
3 days ago
1:39

xHamster

Sissy Stephie Jacks

Sissy Cumslut Trainer
3 years ago
9:50

xHamster

Sissy Cumslut Trainer

Sissy Asian Horny
55 days ago
7:09

xHamster

Sissy Asian Horny

Anal Submission - Sissy
3 years ago
5:17

xHamster

Anal Submission - Sissy

Sissy Blowjob Instructions
3 years ago
5:05

xHamster

Sissy Blowjob Instructions

Sissy maid fucked
5 years ago
24:12

Tube8

Sissy maid fucked

Sissy Submission Training
3 years ago
12:38

Tube8

Sissy Submission Training

extreme anal sissy
7 years ago
3:57

xHamster

extreme anal sissy

Sissy Boy Anal
7 years ago
40:04

xHamster

Sissy Boy Anal

Sissy Maker 3
2 years ago
6:48

Tube8

Sissy Maker 3

Sissy Punishing Herself
3 years ago
0:54

xHamster

Sissy Punishing Herself

sissy babies diaper
7 years ago
1:08

xHamster

sissy babies diaper

Sissy Addiction 2 - SissyHypnoz
10 months ago
3:53

SunPorno

Sissy Addiction 2 - SissyHypnoz

Sissy Shemale Bimbo Transformer
2 years ago
17:04

xHamster

Sissy Shemale Bimbo Transformer

OMG you sissy fag
4 years ago
10:30

xHamster

OMG you sissy fag

Sissy deepthroating big dildo
3 years ago
2:54

PornHub

Sissy deepthroating big dildo

Sissy Anal Submission Training
4 years ago
5:17

xHamster

Sissy Anal Submission Training

Sissy in Action 001
3 years ago
30:35

Tube8

Sissy in Action 001

Sissy maid gets rammed
4 years ago
2:10

xHamster

Sissy maid gets rammed

Sissy Boy Foot Worship
4 years ago
6:06

DrTuber

Sissy Boy Foot Worship

Sissy Faggot Humiliation Joi
10 months ago
7:16

PornHub

Sissy Faggot Humiliation Joi

Your,e a Sissy
2 years ago
2:30

PornHub

Your,e a Sissy

Mistress Dildos Sissy Slave
3 years ago
14:25

Tube8

Mistress Dildos Sissy Slave

SISSY LOVES TO PLEASE
3 years ago
6:24

Tube8

SISSY LOVES TO PLEASE

Sissy Hypno Cock Worship
1 year ago
4:21

PornHub

Sissy Hypno Cock Worship

Mistresses fuck sissy ass
1 year ago
5:20

DrTuber

Mistresses fuck sissy ass

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

xHamster

Fucking My Sissy Slave!!!

Sissy Training Crossdresser Humiliation
3 years ago
3:15

SunPorno

Sissy Training Crossdresser Humiliation

Clean My Toilet Sissy!
1 year ago
7:05

xHamster

Clean My Toilet Sissy!

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 Sexy Leather Doll
1 year ago
6:34

NuVid

Sissy Sexy Leather Doll

sissy shelly pvc dress
6 days ago
1:50

xHamster

sissy shelly pvc dress

Vera fucking sissy hubby
3 years ago
2:58

PornHub

Vera fucking sissy hubby

sissy jerking off 3
4 years ago
1:00

xHamster

sissy jerking off 3

Big v Sissy - London
4 months ago
4:52

DrTuber

Big v Sissy - London

Sissy CD dick bouncing
3 months ago
29:33

xHamster

Sissy CD dick bouncing

hot sissy boy dildoing
5 years ago
7:29

xHamster

hot sissy boy dildoing

chastised  sissy fuck toys
6 years ago
6:41

xHamster

chastised sissy fuck toys

michaels dirty sissy slut
6 years ago
3:18

xHamster

michaels dirty sissy slut

My Sissy Dream 6
46 days ago
14:14

RedTube

My Sissy Dream 6

Punishing a Sissy Slut
6 years ago
5:37

xHamster

Punishing a Sissy Slut

Whit a sissy slut
5 years ago
0:59

xHamster

Whit a sissy slut

Sissy Strokes and Cums
6 years ago
3:56

xHamster

Sissy Strokes and Cums

sissy cocksucking slave training
6 years ago
31:00

xHamster

sissy cocksucking slave training

Fat sissy outdoor #2
6 years ago
3:21

xHamster

Fat sissy outdoor #2

Sissy boy gets pampered
5 years ago
18:28

RedTube

Sissy boy gets pampered

Sissy sex in  panties
7 years ago
5:14

xHamster

Sissy sex in panties

Male sissy sucks cock.
3 months ago
3:29

xHamster

Male sissy sucks cock.

huge cock sissy slut
2 months ago
2:15

xHamster

huge cock sissy slut

Fat Sissy Video #4
7 years ago
1:08

xHamster

Fat Sissy Video #4

Anti Sissy Hypno 2
4 months ago
5:13

PornHub

Anti Sissy Hypno 2

smoking sissy slut chrissy
6 years ago
3:16

xHamster

smoking sissy slut chrissy

Sissy Sweet Interracial Assfuck
6 years ago
15:11

Tube8

Sissy Sweet Interracial Assfuck

Mistress sissy boy Strapon
4 years ago
24:17

xHamster

Mistress sissy boy Strapon

Mistress spanking useless sissy
4 years ago
5:30

Tube8

Mistress spanking useless sissy

Mistress Dildos Sissy Slave
4 years ago
14:26

Tube8

Mistress Dildos Sissy Slave

tv sissy cocksucking slut
6 years ago
1:14

xHamster

tv sissy cocksucking slut

Cumming French Maid Sissy
20 days ago
11:02

xHamster

Cumming French Maid Sissy

Drinks that are Sissy
3 months ago
8:04

NuVid

Drinks that are Sissy

Latex Sissy Maid Cuckolded
6 years ago
6:06

GotPorn

Latex Sissy Maid Cuckolded

Face Sitting On Sissy Boy
5 years ago
6:15

GotPorn

Face Sitting On Sissy Boy

Domina Strapon Fucks Sissy Boy
6 years ago
25:36

Tube8

Domina Strapon Fucks Sissy Boy

Ass Fucking Her Male Sissy
7 years ago
9:39

GotPorn

Ass Fucking Her Male Sissy

Sissy Hubby Has Hot Wife
3 years ago
5:02

Tube8

Sissy Hubby Has Hot Wife

Strapon babes pegging sissy guy
4 years ago
5:07

PornHub

Strapon babes pegging sissy guy

cute sissy boy fingering himself
3 years ago
3:38

xHamster

cute sissy boy fingering himself

Sissy sexy in leather 4
4 years ago
1:20

xHamster

Sissy sexy in leather 4

black cocks for sissy whores
3 years ago
4:08

xHamster

black cocks for sissy whores

Dominatrix babes pegging their sissy
2 years ago
6:14

DrTuber

Dominatrix babes pegging their sissy

Femdom wife dominates crossdressing sissy
2 years ago
6:06

DrTuber

Femdom wife dominates crossdressing sissy

Sissy Chastity Slave Worships Feet
6 years ago
7:03

SunPorno

Sissy Chastity Slave Worships Feet

sissy gf lacey and hrdblkdcknsd
3 years ago
0:32

xHamster

sissy gf lacey and hrdblkdcknsd

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

xHamster

White sissy cuckold trainer - mix

Sissy at the Truck Stop
2 years ago
0:49

xHamster

Sissy at the Truck Stop

sissy video 29 filling pritty
34 days ago
1:45

xHamster

sissy video 29 filling pritty

Bitch femdoms face sitting sissy
3 years ago
5:18

DrTuber

Bitch femdoms face sitting sissy

Strapon Butt Plug BDSM sissy
6 years ago
8:58

DrTuber

Strapon Butt Plug BDSM sissy

Spanked sissy movietures and paddling
40 days ago
7:02

RedTube

Spanked sissy movietures and paddling

Sissy doing Ass to mouth
50 days ago
3:22

xHamster

Sissy doing Ass to mouth

Mistress sissy to suck cock
3 years ago
2:52

xHamster

Mistress sissy to suck cock

Sissy Boy Receives Anal Punishment
6 years ago
9:25

GotPorn

Sissy Boy Receives Anal Punishment

Mr Bean Becomes a Sissy
2 months ago
3:32

PornHub

Mr Bean Becomes a Sissy

Tranny and sissy sex partys
1 year ago
5:24

DrTuber

Tranny and sissy sex partys

shemale sissy sounding in urethral
9 months ago
2:39

PornHub

shemale sissy sounding in urethral

Sissy sexy leather catsuit 1
4 years ago
3:17

xHamster

Sissy sexy leather catsuit 1

Showing off as a sissy
4 months ago
5:46

PornHub

Showing off as a 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

my soft sissy clit cumming
1 year ago
0:32

PornHub

my soft sissy clit cumming

Sissy Boy Strap On Hell
5 years ago
7:20

DrTuber

Sissy Boy Strap On Hell

Sissy taking a large dildo
4 years ago
0:42

xHamster

Sissy taking a large dildo

Femdom sissy slave torture session
4 years ago
31:04

RedTube

Femdom sissy slave torture session

sissy ts pen in sounding
10 months ago
16:32

xHamster

sissy ts pen in sounding

Sissy Ray in White Panties
4 years ago
0:24

xHamster

Sissy Ray in White Panties

Sissy sexy leather dress 2
4 years ago
1:13

xHamster

Sissy sexy leather dress 2

Sissy sexy in leather 5
4 years ago
0:47

xHamster

Sissy sexy in leather 5

Mistress Handjob Sissy Chastity Tease
4 years ago
8:52

Tube8

Mistress Handjob Sissy Chastity Tease

Domina mastering sissy and servant
4 years ago
5:05

DrTuber

Domina mastering sissy and servant

Sissy Hubby Watches Hot Wife
4 years ago
5:00

Tube8

Sissy Hubby Watches Hot Wife

Sissy gets to fuck mistress
4 years ago
31:10

xHamster

Sissy gets to fuck mistress

I am a sissy boy
1 year ago
14:26

xHamster

I am a sissy boy

sissy dildo fucking in chastity
4 years ago
3:39

xHamster

sissy dildo fucking in chastity

Kalina Dirty Smoking Sissy Whore
1 year ago
7:56

PornHub

Kalina Dirty Smoking Sissy Whore

Sissy Faggot Pink Holder Smoke
1 year ago
1:43

PornHub

Sissy Faggot Pink Holder Smoke

Crossdresser gay sissy gets fucked
5 years ago
9:49

Tube8

Crossdresser gay sissy gets fucked

SISSY IN RED DRESS 4
4 months ago
0:50

DrTuber

SISSY IN RED DRESS 4

Being a Sissy in Diaper
4 months ago
2:20

NuVid

Being a Sissy in Diaper

SISSY CD GETTING FUCKED B2
1 year ago
6:51

PornHub

SISSY CD GETTING FUCKED B2

Sissy sexy leather girl 3
3 years ago
0:50

NuVid

Sissy sexy leather girl 3

Sissy Hypno Dildo Poppers Trainer
1 year ago
14:00

PornHub

Sissy Hypno Dildo Poppers Trainer

Redhead gives footjob to sissy
5 years ago
5:09

Tube8

Redhead gives footjob to sissy

French redhead uses crossdressing sissy
1 year ago
30:48

xHamster

French redhead uses crossdressing sissy

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

xHamster

Sissy bound, ass fucked and BJ

Hung Sissy Crossdresser Takes MONSTER Dildo
5 months ago
5:01

RedTube

Hung Sissy Crossdresser Takes MONSTER Dildo