Sissy: 402 Videos

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

xHamster

Sissy Ray in Pink Sissy Dress (Twirling Upskirt)

Sissy dancing like a sissy for you
3 months ago
2:33

xHamster

Sissy dancing like a sissy for you

Sissy Sissy in Chastity
2 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 3SUM
3 years ago
28:24

Tube8

Sissy 3SUM

Sissy 6
7 years ago
1:54

xHamster

Sissy 6

Smoking Sissy
3 years ago
0:54

xHamster

Smoking Sissy

sissy domination
3 years ago
23:16

xHamster

sissy domination

Bimboization - Sissy
4 years ago
2:23

xHamster

Bimboization - Sissy

Sissy amateur
9 months ago
0:06

PornHub

Sissy amateur

anyones sissy
5 years ago
2:37

Tube8

anyones sissy

Sissy Fucking
3 years ago
1:24:12

Tube8

Sissy Fucking

Sissy Toying
1 year ago
26:54

Tube8

Sissy Toying

Sissy Musings
1 year ago
11:52

Tube8

Sissy Musings

smoking sissy
3 years ago
5:40

PornHub

smoking sissy

sissy maid
7 years ago
5:46

xHamster

sissy maid

Sissy Threesome
3 years ago
23:24

Tube8

Sissy Threesome

sissy claire.
8 years ago
0:33

xHamster

sissy claire.

sissy gianakopoulou
8 years ago
6:26

xHamster

sissy gianakopoulou

Sissy Wedding
7 years ago
2:37

xHamster

Sissy Wedding

Sissy Addiction
8 months ago
3:40

xHamster

Sissy Addiction

Sissy-Slut
6 months ago
0:26

xHamster

Sissy-Slut

sissy shelly
4 months ago
2:44

xHamster

sissy shelly

Sissy Training
4 years ago
14:41

xHamster

Sissy Training

Sissy Fuck
4 years ago
4:02

xHamster

Sissy Fuck

sissy me
8 years ago
7:44

xHamster

sissy me

Sissy Crossdresser
7 months ago
4:12

xHamster

Sissy Crossdresser

Sissy Spank
6 years ago
4:02

xHamster

Sissy Spank

Sissy Jana
2 months ago
1:47

xHamster

Sissy Jana

Sissy maker
5 years ago
3:54

PornHub

Sissy maker

hairy SISSY
6 years ago
12:39

xHamster

hairy SISSY

Sissy Struggles
4 years ago
5:04

xHamster

Sissy Struggles

Sissy add2
5 years ago
5:00

xHamster

Sissy add2

Mincing Sissy
7 months ago
1:44

PornHub

Mincing Sissy

Sissy bounce
4 months ago
0:12

xHamster

Sissy bounce

Sissy Maid Fuck
4 years ago
4:49

xHamster

Sissy Maid Fuck

Sissy Maid Gold
2 years ago
11:01

xHamster

Sissy Maid Gold

Kim and sissy
6 years ago
0:35

xHamster

Kim and sissy

Sissy serves man
4 years ago
14:23

xHamster

Sissy serves man

Sissy in Leather
6 years ago
0:47

Tube8

Sissy in Leather

Sissy wets diaper
4 years ago
0:56

xHamster

Sissy wets diaper

Sissy Submission Training
4 years ago
12:38

Tube8

Sissy Submission Training

Sissy Blowjob Instructions
4 years ago
5:05

xHamster

Sissy Blowjob Instructions

sissy dildo fun
3 years ago
2:00

xHamster

sissy dildo fun

Anal Submission - Sissy
4 years ago
5:17

xHamster

Anal Submission - Sissy

Sissy Punishing Herself
3 years ago
0:54

xHamster

Sissy Punishing Herself

Sissy Cumslut Trainer
3 years ago
9:50

xHamster

Sissy Cumslut Trainer

Sissy Daddys stable
5 years ago
0:50

xHamster

Sissy Daddys stable

tits sissy nikki
3 years ago
1:34

RedTube

tits sissy nikki

Sissy gets opened
5 years ago
5:47

xHamster

Sissy gets opened

sissy boy fucking
5 years ago
15:09

xHamster

sissy boy fucking

Sissy Maker 3
2 years ago
6:48

Tube8

Sissy Maker 3

Sissy maid fucked
6 years ago
24:12

Tube8

Sissy maid fucked

ASS SISSY DESTROYED
1 year ago
6:09

xHamster

ASS SISSY DESTROYED

Submissive Sissy Slut
1 year ago
2:56

PornHub

Submissive Sissy Slut

Sissy Time 7
1 year ago
4:40

xHamster

Sissy Time 7

Sissy Stephie Jacks
5 months ago
1:39

xHamster

Sissy Stephie Jacks

Shari Sissy Masturbation
6 years ago
4:37

xHamster

Shari Sissy Masturbation

Sissy slut masturbates
6 months ago
1:08

xHamster

Sissy slut masturbates

sissy strap-on
6 years ago
3:59

xHamster

sissy strap-on

Bareback Sissy Balletrocks
3 months ago
24:26

xHamster

Bareback Sissy Balletrocks

sissy looks hot
10 months ago
0:30

PornHub

sissy looks hot

Femdom - Sissy Boys
6 years ago
2:13

xHamster

Femdom - Sissy Boys

Sissy Wedding Night
7 years ago
2:59

xHamster

Sissy Wedding Night

Sissy Renate maulgefickt
1 year ago
4:21

xHamster

Sissy Renate maulgefickt

Crossdreser sissy fucked
6 years ago
14:48

xHamster

Crossdreser sissy fucked

Sweet Sissy Fucking
3 months ago
4:39

xHamster

Sweet Sissy Fucking

Sissy Hypno Fetish
1 year ago
2:19

PornHub

Sissy Hypno Fetish

Latex Sissy Maid
4 years ago
1:42

xHamster

Latex Sissy Maid

sissy babies diaper
8 years ago
1:08

xHamster

sissy babies diaper

Sissy Stair Struggle
10 months ago
27:27

PornHub

Sissy Stair Struggle

extreme anal sissy
7 years ago
3:57

xHamster

extreme anal sissy

Sissy Boy Anal
7 years ago
40:04

xHamster

Sissy Boy Anal

Dutch prossie rides sissy
2 months ago
10:10

GotPorn

Dutch prossie rides sissy

Mistress Dildos Sissy Slave
4 years ago
14:25

Tube8

Mistress Dildos Sissy Slave

Sissy Faggot Humiliation Joi
1 year ago
7:16

PornHub

Sissy Faggot Humiliation Joi

Sissy Boy Foot Worship
5 years ago
6:06

DrTuber

Sissy Boy Foot Worship

My Sissy Dream 6
6 months ago
14:14

RedTube

My Sissy Dream 6

sissy with black dress
52 days ago
4:25

xHamster

sissy with black dress

Robert jessop outted sissy
2 months ago
0:47

xHamster

Robert jessop outted sissy

Sissy Anal Submission Training
5 years ago
5:17

xHamster

Sissy Anal Submission Training

sissy jerking off 3
4 years ago
1:00

xHamster

sissy jerking off 3

SISSY LOVES TO PLEASE
4 years ago
6:24

Tube8

SISSY LOVES TO PLEASE

Drinks that are Sissy
8 months ago
8:04

NuVid

Drinks that are Sissy

Anti Sissy Hypno 2
9 months ago
5:13

PornHub

Anti Sissy Hypno 2

Sissy Sexy Leather Doll
1 year ago
6:34

NuVid

Sissy Sexy Leather Doll

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

xHamster

Fucking My Sissy Slave!!!

Mistresses fuck sissy ass
1 year ago
5:20

DrTuber

Mistresses fuck sissy ass

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

Your,e a Sissy
2 years ago
2:30

PornHub

Your,e a Sissy

Sissy Addiction 2 - SissyHypnoz
1 year ago
3:53

SunPorno

Sissy Addiction 2 - SissyHypnoz

Sissy in Action 001
3 years ago
30:35

Tube8

Sissy in Action 001

Sissy deepthroating big dildo
3 years ago
2:54

PornHub

Sissy deepthroating big dildo

DianeL BBW Sissy Smoke
3 years ago
0:36

PornHub

DianeL BBW Sissy Smoke

Sissy Training Crossdresser Humiliation
3 years ago
3:15

SunPorno

Sissy Training Crossdresser Humiliation

Sissy Shemale Bimbo Transformer
2 years ago
17:04

xHamster

Sissy Shemale Bimbo Transformer

Big v Sissy - London
9 months ago
4:52

DrTuber

Big v Sissy - London

Vera fucking sissy hubby
4 years ago
2:58

PornHub

Vera fucking sissy hubby

Sissy Hypno Cock Worship
2 years ago
4:21

PornHub

Sissy Hypno Cock Worship

Sissy maid gets rammed
5 years ago
2:10

xHamster

Sissy maid gets rammed

Sissy boy gets pampered
5 years ago
18:28

RedTube

Sissy boy gets pampered

michaels dirty sissy slut
6 years ago
3:18

xHamster

michaels dirty sissy slut

chastised  sissy fuck toys
6 years ago
6:41

xHamster

chastised sissy fuck toys

hot sissy boy dildoing
5 years ago
7:29

xHamster

hot sissy boy dildoing

Fat Sissy Video #4
8 years ago
1:08

xHamster

Fat Sissy Video #4

smoking sissy slut chrissy
6 years ago
3:16

xHamster

smoking sissy slut chrissy

Whit a sissy slut
6 years ago
0:59

xHamster

Whit a sissy slut

Latex Sissy Maid Cuckolded
6 years ago
6:06

GotPorn

Latex Sissy Maid Cuckolded

Mistress spanking useless sissy
5 years ago
5:30

Tube8

Mistress spanking useless sissy

tv sissy cocksucking slut
6 years ago
1:14

xHamster

tv sissy cocksucking slut

Sissy Sweet Interracial Assfuck
6 years ago
15:11

Tube8

Sissy Sweet Interracial Assfuck

Punishing a Sissy Slut
6 years ago
5:37

xHamster

Punishing a Sissy Slut

OMG you sissy fag
5 years ago
10:30

xHamster

OMG you sissy fag

Fat sissy outdoor #2
7 years ago
3:21

xHamster

Fat sissy outdoor #2

Mistress Dildos Sissy Slave
5 years ago
14:26

Tube8

Mistress Dildos Sissy Slave

sissy cocksucking slave training
7 years ago
31:00

xHamster

sissy cocksucking slave training

Mistress sissy boy Strapon
5 years ago
24:17

xHamster

Mistress sissy boy Strapon

Sissy Strokes and Cums
7 years ago
3:56

xHamster

Sissy Strokes and Cums

Sissy sex in  panties
7 years ago
5:14

xHamster

Sissy sex in panties

Strapon babes pegging sissy guy
4 years ago
5:07

PornHub

Strapon babes pegging sissy guy

Face Sitting On Sissy Boy
5 years ago
6:15

GotPorn

Face Sitting On Sissy Boy

Sissy Boy Receives Anal Punishment
7 years ago
9:25

GotPorn

Sissy Boy Receives Anal Punishment

Redhead gives footjob to sissy
5 years ago
5:09

Tube8

Redhead gives footjob to sissy

Bitch femdoms face sitting sissy
3 years ago
5:18

DrTuber

Bitch femdoms face sitting sissy

sissy gf lacey and hrdblkdcknsd
3 years ago
0:32

xHamster

sissy gf lacey and hrdblkdcknsd

Sissy taking a large dildo
5 years ago
0:42

xHamster

Sissy taking a large dildo

cute sissy boy fingering himself
3 years ago
3:38

xHamster

cute sissy boy fingering himself

Mistress sissy to suck cock
3 years ago
2:52

xHamster

Mistress sissy to suck cock

Kalina Dirty Smoking Sissy Whore
2 years ago
7:56

PornHub

Kalina Dirty Smoking Sissy Whore

Spanked sissy movietures and paddling
6 months ago
7:02

RedTube

Spanked sissy movietures and paddling

sissy video 39 daddy daved
3 months ago
2:29

xHamster

sissy video 39 daddy daved

Sissy Boy Strap On Hell
5 years ago
7:20

DrTuber

Sissy Boy Strap On Hell

Sissy Hubby Has Hot Wife
4 years ago
5:02

Tube8

Sissy Hubby Has Hot Wife

Sissy at the Truck Stop
3 years ago
0:49

xHamster

Sissy at the Truck Stop

Crossdresser gay sissy gets fucked
6 years ago
9:49

Tube8

Crossdresser gay sissy gets fucked

sissy ts pen in sounding
1 year ago
16:32

xHamster

sissy ts pen in sounding

my soft sissy clit cumming
1 year ago
0:32

PornHub

my soft sissy clit cumming

I am a sissy boy
1 year ago
14:26

xHamster

I am a sissy boy

French redhead uses crossdressing sissy
1 year ago
30:48

xHamster

French redhead uses crossdressing sissy

Sissy Hypno Dildo Poppers Trainer
1 year ago
14:00

PornHub

Sissy Hypno Dildo Poppers Trainer

Ass Fucking Her Male Sissy
7 years ago
9:39

GotPorn

Ass Fucking Her Male Sissy

SISSY CD GETTING FUCKED B2
1 year ago
6:51

PornHub

SISSY CD GETTING FUCKED B2

Sissy Faggot Pink Holder Smoke
1 year ago
1:43

PornHub

Sissy Faggot Pink Holder Smoke

Sissy Chastity Slave Worships Feet
7 years ago
7:03

SunPorno

Sissy Chastity Slave Worships Feet

Mr Bean Becomes a Sissy
7 months ago
3:32

PornHub

Mr Bean Becomes a Sissy

Sissy sucking a hard cock
25 days ago
0:19

xHamster

Sissy sucking a hard cock

Tranny and sissy sex partys
2 years ago
5:24

DrTuber

Tranny and sissy sex partys

SISSY IN RED DRESS 4
9 months ago
0:50

DrTuber

SISSY IN RED DRESS 4

Being a Sissy in Diaper
9 months ago
2:20

NuVid

Being a Sissy in Diaper

Femdom wife dominates crossdressing sissy
2 years ago
6:06

DrTuber

Femdom wife dominates crossdressing sissy

sissy video 29 filling pritty
6 months ago
1:45

xHamster

sissy video 29 filling pritty

Dominatrix babes pegging their sissy
2 years ago
6:14

DrTuber

Dominatrix babes pegging their sissy

Showing off as a sissy
9 months ago
5:46

PornHub

Showing off as a sissy

Strapon Butt Plug BDSM sissy
6 years ago
8:58

DrTuber

Strapon Butt Plug BDSM sissy

Sissy sexy in leather 5
4 years ago
0:47

xHamster

Sissy sexy in leather 5

Sissy sexy leather dress 2
4 years ago
1:13

xHamster

Sissy sexy leather dress 2

black cocks for sissy whores
4 years ago
4:08

xHamster

black cocks for sissy whores

Femdom sissy slave torture session
4 years ago
31:04

RedTube

Femdom sissy slave torture session

sissy dildo fucking in chastity
4 years ago
3:39

xHamster

sissy dildo fucking in chastity

Sissy Buttplgug Jerk and Cum
4 years ago
3:18

xHamster

Sissy Buttplgug Jerk and Cum

Mistress Handjob Sissy Chastity Tease
5 years ago
8:52

Tube8

Mistress Handjob Sissy Chastity Tease

Sissy sexy leather outfit 1
4 years ago
1:04

xHamster

Sissy sexy leather outfit 1

Sissy gets to fuck mistress
5 years ago
31:10

xHamster

Sissy gets to fuck mistress

Sissy sexy leather catsuit 1
4 years ago
3:17

xHamster

Sissy sexy leather catsuit 1

My sissy hole is hungry
2 months ago
2:50

xHamster

My sissy hole is hungry

Sissy sexy in leather 4
4 years ago
1:20

xHamster

Sissy sexy in leather 4

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

xHamster

White sissy cuckold trainer - mix

Sissy Hubby Watches Hot Wife
5 years ago
5:00

Tube8

Sissy Hubby Watches Hot Wife

Domina Strapon Fucks Sissy Boy
6 years ago
25:36

Tube8

Domina Strapon Fucks Sissy Boy

Sissy Ray in White Panties
5 years ago
0:24

xHamster

Sissy Ray in White Panties

Sissy sexy leather girl 3
4 years ago
0:50

NuVid

Sissy sexy leather girl 3

Sissy maid in white stockings
2 months ago
5:03

xHamster

Sissy maid in white stockings

Domina mastering sissy and servant
5 years ago
5:05

DrTuber

Domina mastering sissy and servant

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

PornHub

Mistress Fucking a Sissy in Pantyhose

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

GotPorn

Crossdressing sissy gets handjob during roleplay

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

xHamster

Shari a Sissy Maid Riding Dildo

Diane Trashy BBW Sissy Smoke Bimbo
1 year ago
1:51

xHamster

Diane Trashy BBW Sissy Smoke Bimbo

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

Tube8

No Cum For You Sissy Boy