Sissy: 367 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
7 years ago
5:00

GotPorn

Sissy

sissy
1 year ago
2:18

xHamster

sissy

Sissy Musings
11 months ago
11:52

Tube8

Sissy Musings

Sissy 6
6 years ago
1:54

xHamster

Sissy 6

Sissy Toying
11 months ago
26:54

Tube8

Sissy Toying

smoking sissy
2 years ago
5:40

PornHub

smoking sissy

Sissy Threesome
2 years ago
23:24

Tube8

Sissy Threesome

Sissy Addiction
33 days ago
3:40

xHamster

Sissy Addiction

sissy gianakopoulou
8 years ago
6:26

xHamster

sissy gianakopoulou

Sissy Fucking
2 years ago
1:24:12

Tube8

Sissy Fucking

sissy claire.
7 years ago
0:33

xHamster

sissy claire.

sissy me
7 years ago
7:44

xHamster

sissy me

Bimboization - Sissy
3 years ago
2:23

xHamster

Bimboization - Sissy

Smoking Sissy
3 years ago
0:54

xHamster

Smoking Sissy

good sissy
3 years ago
0:16

xHamster

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anyones sissy
5 years ago
2:37

Tube8

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sissy domination
3 years ago
23:16

xHamster

sissy domination

Sissy maker
4 years ago
3:54

PornHub

Sissy maker

Sissy amateur
56 days ago
0:06

PornHub

Sissy amateur

Sissy 3SUM
2 years ago
28:24

Tube8

Sissy 3SUM

Sissy add2
4 years ago
5:00

xHamster

Sissy add2

Sissy Struggles
3 years ago
5:04

xHamster

Sissy Struggles

Sissy Wedding
6 years ago
2:37

xHamster

Sissy Wedding

Sissy Spank
6 years ago
4:02

xHamster

Sissy Spank

House Sissy
6 years ago
6:26

xHamster

House Sissy

hairy SISSY
5 years ago
12:39

xHamster

hairy SISSY

sissy maid
7 years ago
5:46

xHamster

sissy maid

Sissy Fuck
4 years ago
4:02

xHamster

Sissy Fuck

Sissy Training
3 years ago
14:41

xHamster

Sissy Training

Stupid Sissy Whore!
53 days ago
0:44

xHamster

Stupid Sissy Whore!

CD Sissy Bukkake
54 days ago
11:55

xHamster

CD Sissy Bukkake

Sissy Submission Training
3 years ago
12:38

Tube8

Sissy Submission Training

Sissy Stair Struggle
3 months ago
27:27

PornHub

Sissy Stair Struggle

Sissy in Leather
5 years ago
0:47

Tube8

Sissy in Leather

Sissy Hypno Fetish
8 months ago
2:19

PornHub

Sissy Hypno Fetish

Sissy Blowjob Instructions
3 years ago
5:05

xHamster

Sissy Blowjob Instructions

tits sissy nikki
2 years ago
1:34

RedTube

tits sissy nikki

Sissy Maker 3
2 years ago
6:48

Tube8

Sissy Maker 3

sissy boy fucking
4 years ago
15:09

xHamster

sissy boy fucking

Sissy Cumslut Trainer
3 years ago
9:50

xHamster

Sissy Cumslut Trainer

Sissy Daddys stable
4 years ago
0:50

xHamster

Sissy Daddys stable

Sissy Punishing Herself
3 years ago
0:54

xHamster

Sissy Punishing Herself

Sissy Time 7
5 months ago
4:40

xHamster

Sissy Time 7

sissy looks hot
2 months ago
0:30

PornHub

sissy looks hot

Sissy gets opened
5 years ago
5:47

xHamster

Sissy gets opened

Anal Submission - Sissy
3 years ago
5:17

xHamster

Anal Submission - Sissy

Sissy Maid Gold
2 years ago
11:01

xHamster

Sissy Maid Gold

Shari Sissy Masturbation
6 years ago
4:37

xHamster

Shari Sissy Masturbation

Sissy wets diaper
3 years ago
0:56

xHamster

Sissy wets diaper

sissy babies diaper
7 years ago
1:08

xHamster

sissy babies diaper

Sissy gets pegged
38 days ago
4:31

xHamster

Sissy gets pegged

Sissy Wedding Night
6 years ago
2:59

xHamster

Sissy Wedding Night

sissy dildo fun
2 years ago
2:00

xHamster

sissy dildo fun

ASS SISSY DESTROYED
7 months ago
6:09

xHamster

ASS SISSY DESTROYED

Sissy serves man
3 years ago
14:23

xHamster

Sissy serves man

Sissy Renate maulgefickt
6 months ago
4:21

xHamster

Sissy Renate maulgefickt

Sissy Maid Fuck
4 years ago
4:49

xHamster

Sissy Maid Fuck

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 husband private
4 years ago
1:35

xHamster

sissy husband private

Kim and sissy
5 years ago
0:35

xHamster

Kim and sissy

Latex Sissy Maid
3 years ago
1:42

xHamster

Latex Sissy Maid

Sissy Boy Anal
6 years ago
40:04

xHamster

Sissy Boy Anal

extreme anal sissy
6 years ago
3:57

xHamster

extreme anal sissy

Submissive Sissy Slut
6 months ago
2:56

PornHub

Submissive Sissy Slut

Femdom - Sissy Boys
6 years ago
2:13

xHamster

Femdom - Sissy Boys

Sissy maid fucked
5 years ago
24:12

Tube8

Sissy maid fucked

Sissy Gets Fucked
45 days ago
0:16

xHamster

Sissy Gets Fucked

OMG you sissy fag
4 years ago
10:30

xHamster

OMG you sissy fag

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

xHamster

Fucking My Sissy Slave!!!

Mistress Dildos Sissy Slave
3 years ago
14:25

Tube8

Mistress Dildos Sissy Slave

sissy jerking off 3
4 years ago
1:00

xHamster

sissy jerking off 3

SISSY LOVES TO PLEASE
3 years ago
6:24

Tube8

SISSY LOVES TO PLEASE

Sissy in Action 001
3 years ago
30:35

Tube8

Sissy in Action 001

Mistress spanking useless sissy
4 years ago
5:30

Tube8

Mistress spanking useless sissy

Sissy Boy Foot Worship
4 years ago
6:06

DrTuber

Sissy Boy Foot Worship

Sissy Faggot Humiliation Joi
8 months ago
7:16

PornHub

Sissy Faggot Humiliation Joi

Mistress sissy boy Strapon
4 years ago
24:17

xHamster

Mistress sissy boy Strapon

Mistress Dildos Sissy Slave
4 years ago
14:26

Tube8

Mistress Dildos Sissy Slave

Sissy Anal Submission Training
4 years ago
5:17

xHamster

Sissy Anal Submission Training

Sissy Addiction 2 - SissyHypnoz
8 months ago
3:53

SunPorno

Sissy Addiction 2 - SissyHypnoz

Vera fucking sissy hubby
3 years ago
2:58

PornHub

Vera fucking sissy hubby

Sissy maid gets rammed
4 years ago
2:10

xHamster

Sissy maid gets rammed

Clean My Toilet Sissy!
1 year ago
7:05

xHamster

Clean My Toilet Sissy!

Sissy Sweet Interracial Assfuck
5 years ago
15:11

Tube8

Sissy Sweet Interracial Assfuck

Fat Sissy Video #4
7 years ago
1:08

xHamster

Fat Sissy Video #4

Anti Sissy Hypno 2
49 days ago
5:13

PornHub

Anti Sissy Hypno 2

Sissy CD dick bouncing
43 days ago
29:33

xHamster

Sissy CD dick bouncing

Sissy sex in  panties
6 years ago
5:14

xHamster

Sissy sex in panties

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

Tube8

Domination of a sissy

Male sissy sucks cock.
34 days ago
3:29

xHamster

Male sissy sucks cock.

Drinks that are Sissy
28 days ago
8:04

NuVid

Drinks that are Sissy

Fat sissy outdoor #2
6 years ago
3:21

xHamster

Fat sissy outdoor #2

sissy cocksucking slave training
6 years ago
31:00

xHamster

sissy cocksucking slave training

Punishing a Sissy Slut
6 years ago
5:37

xHamster

Punishing a Sissy Slut

Sissy Hypno Cock Worship
1 year ago
4:21

PornHub

Sissy Hypno Cock Worship

michaels dirty sissy slut
6 years ago
3:18

xHamster

michaels dirty sissy slut

chastised  sissy fuck toys
6 years ago
6:41

xHamster

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Your,e a Sissy
1 year ago
2:30

PornHub

Your,e a Sissy

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 Shemale Bimbo Transformer
2 years ago
17:04

xHamster

Sissy Shemale Bimbo Transformer

Sissy Strokes and Cums
6 years ago
3:56

xHamster

Sissy Strokes and Cums

Whit a sissy slut
5 years ago
0:59

xHamster

Whit a sissy slut

tv sissy cocksucking slut
6 years ago
1:14

xHamster

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Big v Sissy - London
2 months ago
4:52

DrTuber

Big v Sissy - London

Sissy Training Crossdresser Humiliation
3 years ago
3:15

SunPorno

Sissy Training Crossdresser Humiliation

Mistresses fuck sissy ass
1 year ago
5:20

DrTuber

Mistresses fuck sissy ass

Sissy Sexy Leather Doll
1 year ago
6:34

NuVid

Sissy Sexy Leather Doll

DianeL BBW Sissy Smoke
3 years ago
0:36

PornHub

DianeL BBW Sissy Smoke

Sissy deepthroating big dildo
2 years ago
2:54

PornHub

Sissy deepthroating big dildo

Sissy boy gets pampered
4 years ago
18:28

RedTube

Sissy boy gets pampered

hot sissy boy dildoing
4 years ago
7:29

xHamster

hot sissy boy dildoing

cute sissy boy fingering himself
3 years ago
3:38

xHamster

cute sissy boy fingering himself

Dominatrix babes pegging their sissy
2 years ago
6:14

DrTuber

Dominatrix babes pegging their sissy

Sissy Faggot Pink Holder Smoke
1 year ago
1:43

PornHub

Sissy Faggot Pink Holder Smoke

my soft sissy clit cumming
9 months ago
0:32

PornHub

my soft sissy clit cumming

Sissy sexy leather girl 3
3 years ago
0:50

NuVid

Sissy sexy leather girl 3

Femdom wife dominates crossdressing sissy
1 year ago
6:06

DrTuber

Femdom wife dominates crossdressing sissy

Mistress sissy to suck cock
3 years ago
2:52

xHamster

Mistress sissy to suck cock

Bitch femdoms face sitting sissy
2 years ago
5:18

DrTuber

Bitch femdoms face sitting sissy

French redhead uses crossdressing sissy
1 year ago
30:48

xHamster

French redhead uses crossdressing sissy

Kalina Dirty Smoking Sissy Whore
1 year ago
7:56

PornHub

Kalina Dirty Smoking Sissy Whore

Strapon babes pegging sissy guy
4 years ago
5:07

PornHub

Strapon babes pegging sissy guy

Sissy Hubby Has Hot Wife
3 years ago
5:02

Tube8

Sissy Hubby Has Hot Wife

Tranny and sissy sex partys
1 year ago
5:24

DrTuber

Tranny and sissy sex partys

sissy gf lacey and hrdblkdcknsd
2 years ago
0:32

xHamster

sissy gf lacey and hrdblkdcknsd

black cocks for sissy whores
3 years ago
4:08

xHamster

black cocks for sissy whores

SISSY CD GETTING FUCKED B2
1 year ago
6:51

PornHub

SISSY CD GETTING FUCKED B2

Sissy Hypno Dildo Poppers Trainer
1 year ago
14:00

PornHub

Sissy Hypno Dildo Poppers Trainer

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

I am a sissy boy
1 year ago
14:26

xHamster

I am a sissy boy

sissy ts pen in sounding
8 months ago
16:32

xHamster

sissy ts pen in sounding

Sissy Boy Receives Anal Punishment
6 years ago
9:25

GotPorn

Sissy Boy Receives Anal Punishment

Sissy Boy Strap On Hell
4 years ago
7:20

DrTuber

Sissy Boy Strap On Hell

Domina Strapon Fucks Sissy Boy
5 years ago
25:36

Tube8

Domina Strapon Fucks Sissy Boy

Sissy taking a large dildo
4 years ago
0:42

xHamster

Sissy taking a large dildo

Sissy Ray in White Panties
4 years ago
0:24

xHamster

Sissy Ray in White Panties

Mistress Handjob Sissy Chastity Tease
4 years ago
8:52

Tube8

Mistress Handjob Sissy Chastity Tease

Sissy gets to fuck mistress
4 years ago
31:10

xHamster

Sissy gets to fuck mistress

Sissy Hubby Watches Hot Wife
4 years ago
5:00

Tube8

Sissy Hubby Watches Hot Wife

shemale sissy sounding in urethral
7 months ago
2:39

PornHub

shemale sissy sounding in urethral

Strapon Butt Plug BDSM sissy
5 years ago
8:58

DrTuber

Strapon Butt Plug BDSM sissy

Redhead gives footjob to sissy
5 years ago
5:09

Tube8

Redhead gives footjob to sissy

Sissy Chastity Slave Worships Feet
6 years ago
7:03

SunPorno

Sissy Chastity Slave Worships Feet

Ass Fucking Her Male Sissy
7 years ago
9:39

GotPorn

Ass Fucking Her Male Sissy

Crossdresser gay sissy gets fucked
5 years ago
9:49

Tube8

Crossdresser gay sissy gets fucked

SISSY IN RED DRESS 4
56 days ago
0:50

DrTuber

SISSY IN RED DRESS 4

sissy vikki fag cum pig
17 days ago
3:10

SunPorno

sissy vikki fag cum pig

Being a Sissy in Diaper
2 months ago
2:20

NuVid

Being a Sissy in Diaper

Showing off as a sissy
2 months ago
5:46

PornHub

Showing off as a sissy

Face Sitting On Sissy Boy
5 years ago
6:15

GotPorn

Face Sitting On Sissy Boy

Domina mastering sissy and servant
4 years ago
5:05

DrTuber

Domina mastering sissy and servant

Sissy sexy leather dress 2
4 years ago
1:13

xHamster

Sissy sexy leather dress 2

Sissy sexy leather outfit 1
3 years ago
1:04

xHamster

Sissy sexy leather outfit 1

Sissy sexy leather catsuit 1
3 years ago
3:17

xHamster

Sissy sexy leather catsuit 1

Femdom sissy slave torture session
4 years ago
31:04

RedTube

Femdom sissy slave torture session

sissy dildo fucking in chastity
3 years ago
3:39

xHamster

sissy dildo fucking in chastity

Sissy sexy in leather 4
4 years ago
1:20

xHamster

Sissy sexy in leather 4

Sissy Buttplgug Jerk and Cum
3 years ago
3:18

xHamster

Sissy Buttplgug Jerk and Cum

Sissy sexy in leather 5
4 years ago
0:47

xHamster

Sissy sexy in leather 5

Sissy Self Pleasure Vol. 9 - SissyHypnoz
8 months ago
3:12

SunPorno

Sissy Self Pleasure Vol. 9 - SissyHypnoz

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

xHamster

Sissy Ray coming home from work

sissy faggot jamessub999 jerking off outside
1 year ago
0:29

PornHub

sissy faggot jamessub999 jerking off outside

Crossdressing sissy jerks off his dick
5 years ago
5:21

Tube8

Crossdressing sissy jerks off his dick

Sissy Maid Sindi Dildo Training 1
5 years ago
2:05

xHamster

Sissy Maid Sindi Dildo Training 1

Crossdressing sissy gets handjob form domina
5 years ago
5:01

GotPorn

Crossdressing sissy gets handjob form domina

Sissy Boy Gets Anally Machined Trained
5 years ago
4:50

GotPorn

Sissy Boy Gets Anally Machined Trained

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

Tube8

No Cum For You Sissy Boy

Cfnm real chicks humliate sissy dudes
3 years ago
5:10

GotPorn

Cfnm real chicks humliate sissy dudes

Sissy Boy Dressed like a Whore.
5 years ago
2:46

Tube8

Sissy Boy Dressed like a Whore.

Sissy Cuntwhore BBC Gangbang Training pt1
1 year ago
14:06

xHamster

Sissy Cuntwhore BBC Gangbang Training pt1

Hardcore sissy gays fucked movietures and
19 days ago
7:29

RedTube

Hardcore sissy gays fucked movietures and

Jon My sissy Great submissive bitch
22 days ago
2:48

xHamster

Jon My sissy Great submissive bitch

Femdom Bride Starla Complete Sissy Domination
2 years ago
25:06

xHamster

Femdom Bride Starla Complete Sissy Domination

Sissy Submits to a TENS unit
6 years ago
3:44

xHamster

Sissy Submits to a TENS unit