Sissy Chastity: 80 Videos

Sissy Feminization: You Need FemDom Sissy Training by Goddess Nikki Kit
3 years ago
1:28

PornHub

Sissy Feminization: You Need FemDom Sissy Training by Goddess Nikki Kit

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Sissy in chastity and sissy jock riding bbc to sissygasm training
3 years ago
5:03

PornHub

Sissy in chastity and sissy jock riding bbc to sissygasm training

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This is how a sissy squirts (Sissy in chastity pees from huge anal dildo)
5 years ago
2:32

PornHub

This is how a sissy squirts (Sissy in chastity pees from huge anal dildo)

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Male fucking my sissy ass from behind. I take his dick wearing my sissy lingerie and chastity cage.
3 years ago
2:25

PornHub

Male fucking my sissy ass from behind. I take his dick wearing my sissy lingerie and chastity cage.

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chastity sissy shock
6 years ago
5:32

XXXDan

chastity sissy shock

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Sissy Chastity Trainer
3 years ago
13:10

JizzBunker

Sissy Chastity Trainer

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Sissy anal training
5 years ago
0:57

PornHub

Sissy anal training

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Sissy Episode: Maid
5 years ago
2:39

PornHub

Sissy Episode: Maid

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Sissy vibrator chastity cum
4 years ago
5:37

PornHub

Sissy vibrator chastity cum

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Sissy slut walk unedited
3 years ago
27:51

PornHub

Sissy slut walk unedited

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Sissy Episode: Self Pounding
5 years ago
3:13

PornHub

Sissy Episode: Self Pounding

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Sissy Femdom Compilation 2
3 years ago
17:52

PornHub

Sissy Femdom Compilation 2

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Mommy locking up her sissy
4 years ago
3:27

PornHub

Mommy locking up her sissy

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Sissy Slut riding dildo hard
3 years ago
1:38

PornHub

Sissy Slut riding dildo hard

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Sissy crossdresser caught and busted!!!!!
3 years ago
0:13

PornHub

Sissy crossdresser caught and busted!!!!!

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Sissy hexy playing with herself
3 years ago
4:17

PornHub

Sissy hexy playing with herself

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Caged sissy cumming with a vibrator
3 years ago
0:40

PornHub

Caged sissy cumming with a vibrator

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Sissy in chastity anal dildo ride
4 years ago
1:18

PornHub

Sissy in chastity anal dildo ride

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Sissy in cage takes MASSIVE creampie
3 years ago
0:25

PornHub

Sissy in cage takes MASSIVE creampie

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Sissy joyce fucked by a machine
3 years ago
0:07

PornHub

Sissy joyce fucked by a machine

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My Sissy Husbands Clit In Chastity
3 years ago
1:11

PornHub

My Sissy Husbands Clit In Chastity

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Podcast Ep13: Sissy, Chastity and Lust
3 years ago
49:07

PornHub

Podcast Ep13: Sissy, Chastity and Lust

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Femdom Foot Worship with Sissy Slave
17 years ago
9:26

PornHub

Femdom Foot Worship with Sissy Slave

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Sissy Crossdresser Princess Masturbating in Chastity
3 months ago
5:16

xHamster

Sissy Crossdresser Princess Masturbating in Chastity

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Sissy in chastity cage bounces on dildo
4 years ago
18:43

PornHub

Sissy in chastity cage bounces on dildo

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Fisting sissy in chastity cum hands free
8 years ago
6:56

xHamster

Fisting sissy in chastity cum hands free

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Sissy Trap Slut Tall High Heels Blonde
4 years ago
0:59

PornHub

Sissy Trap Slut Tall High Heels Blonde

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Sissy Baby Desperate to Cum in Chastity
5 years ago
0:29

PornHub

Sissy Baby Desperate to Cum in Chastity

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Sissy Slut Hiding Huge Cock Under Skirt
4 years ago
0:59

PornHub

Sissy Slut Hiding Huge Cock Under Skirt

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Teaser of sissy slut in chastity sucking
4 years ago
0:26

PornHub

Teaser of sissy slut in chastity sucking

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Sissy in chastity cage masturbates with vibrator
2 days ago
6:58

XXXDan

Sissy in chastity cage masturbates with vibrator

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Abdl sissy riding her dildo in chastity
3 years ago
1:29

PornHub

Abdl sissy riding her dildo in chastity

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Sleazy Sissy Trans Slut Taking Huge Cock
4 years ago
0:59

PornHub

Sleazy Sissy Trans Slut Taking Huge Cock

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Mistress Let's Sissy Play with Pussy
3 years ago
6:50

PornHub

Mistress Let's Sissy Play with Pussy

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Old femboy,chastity,bad dragon,sissy,anal, switch
3 months ago
1:25

xHamster

Old femboy,chastity,bad dragon,sissy,anal, switch

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Sissy Lucy in Chastity with the Fucking Machine
3 years ago
12:22

PornHub

Sissy Lucy in Chastity with the Fucking Machine

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SISSY BITCH CHASTITY COCK FUCKING ASSHLE BIG DILDO
5 years ago
0:27

xHamster

SISSY BITCH CHASTITY COCK FUCKING ASSHLE BIG DILDO

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Sissy fucks herself while she has a chastity cage
3 years ago
2:04

PornHub

Sissy fucks herself while she has a chastity cage

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Caged sissy gets machine fucked close up w/filter
3 years ago
4:24

PornHub

Caged sissy gets machine fucked close up w/filter

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Chastity Anal Orgasms With Huge Dildos Sissy Jessica Bloom
6 months ago
7:11

xHamster

Chastity Anal Orgasms With Huge Dildos Sissy Jessica Bloom

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Horny sissy has an sissygasm in stockings and chastity
4 years ago
17:57

PornHub

Horny sissy has an sissygasm in stockings and chastity

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TS Sissy HuCow Cummies in Chastity Cage - Full Scene!
3 years ago
13:51

PornHub

TS Sissy HuCow Cummies in Chastity Cage - Full Scene!

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Japanese Sissy Femboy Anal in Chasity & Fox tail
3 years ago
14:08

PornHub

Japanese Sissy Femboy Anal in Chasity & Fox tail

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How Devilish Becky Turned You into Her Sissy Chastity
5 years ago
8:35

PornHub

How Devilish Becky Turned You into Her Sissy Chastity

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Dirty Sissy Piss in Chastity on your face outdoors
3 years ago
0:59

PornHub

Dirty Sissy Piss in Chastity on your face outdoors

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Sissygasm Challenge Day 1 - Sissy Trap Boy Rides Dildo
3 years ago
23:42

PornHub

Sissygasm Challenge Day 1 - Sissy Trap Boy Rides Dildo

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Sexy Blonde Sissy Girl Trap Trans Showing Off Lingerie
3 years ago
0:59

PornHub

Sexy Blonde Sissy Girl Trap Trans Showing Off Lingerie

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Pink Sissy Bunny gets tied to BBC Fucking Machine
3 years ago
0:23

PornHub

Pink Sissy Bunny gets tied to BBC Fucking Machine

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Batman CosPlay Parody with Sissy BatGirl and Latex Hit Girl
3 years ago
54:02

PornHub

Batman CosPlay Parody with Sissy BatGirl and Latex Hit Girl

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Sissy spanked and fucked in the ass with a toy
4 years ago
24:00

PornHub

Sissy spanked and fucked in the ass with a toy

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sissy bitch fucked with toys splits ass-hole cock chastity
6 years ago
1:13

xHamster

sissy bitch fucked with toys splits ass-hole cock chastity

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Gothic sissy slut wants to sit on a big cock
3 years ago
1:58

PornHub

Gothic sissy slut wants to sit on a big cock

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Exposed sissy slut Lee fucks his ass locked in chastity!
5 years ago
2:10

PornHub

Exposed sissy slut Lee fucks his ass locked in chastity!

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Sissy Lucy gets Pegged in Chastity whilst trying to wash up
3 years ago
2:08

PornHub

Sissy Lucy gets Pegged in Chastity whilst trying to wash up

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Sissy shows off in electro chastity and ball stretcher via camart
3 years ago
4:38

PornHub

Sissy shows off in electro chastity and ball stretcher via camart

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Caged Ass Training Sissy Bimbo Brandynette Lovense Hush 45mm Anal Plug
4 years ago
19:57

PornHub

Caged Ass Training Sissy Bimbo Brandynette Lovense Hush 45mm Anal Plug

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Savannah Stern cuckolds her husband creampie eating sissy in chastity sex
4 years ago
3:57

PornHub

Savannah Stern cuckolds her husband creampie eating sissy in chastity sex

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Blue balls sissy teasing with vibrator after 48 days without orgasm
3 years ago
2:16

PornHub

Blue balls sissy teasing with vibrator after 48 days without orgasm

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Sexy Sissy Slut on Her Knees For You Taking Huge Cock
4 years ago
0:28

PornHub

Sexy Sissy Slut on Her Knees For You Taking Huge Cock

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Ebony Gf Puts Sissy White Bf in Chastity for Small Dick
5 years ago
0:41

PornHub

Ebony Gf Puts Sissy White Bf in Chastity for Small Dick

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Sissy Mercilessly Teased & Permanently Locked in Metal Chastity Cock Cage
4 years ago
30:29

PornHub

Sissy Mercilessly Teased & Permanently Locked in Metal Chastity Cock Cage

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Teen Sissy slut lee fucks ass and cums locked In chastity
5 years ago
2:14

PornHub

Teen Sissy slut lee fucks ass and cums locked In chastity

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Sissy Crossdresser in corset and heels fucking her ass with dildo
3 years ago
3:32

PornHub

Sissy Crossdresser in corset and heels fucking her ass with dildo

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Sexy Blonde Amatuer Teen Crossdresser Sissy Fucks Ass Glass Buttplug Femboy
4 years ago
0:59

PornHub

Sexy Blonde Amatuer Teen Crossdresser Sissy Fucks Ass Glass Buttplug Femboy

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Sissy Caged Fag Boy Gets Drilled Doggy Style by Fuck Machine
4 years ago
1:09

PornHub

Sissy Caged Fag Boy Gets Drilled Doggy Style by Fuck Machine

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Sissy Cuckold Locked In Chastity Till Hotwife Gets Home From Fucking BBB
4 years ago
0:57

PornHub

Sissy Cuckold Locked In Chastity Till Hotwife Gets Home From Fucking BBB

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Sissy CD Slut riding dildo training for sissygasm in chastity (almost cum)
3 years ago
4:28

PornHub

Sissy CD Slut riding dildo training for sissygasm in chastity (almost cum)

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Sexy Sissy Slut Trap Trans Blonde Girl Fucks Her Ass Hot Anal
4 years ago
0:59

PornHub

Sexy Sissy Slut Trap Trans Blonde Girl Fucks Her Ass Hot Anal

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Super Sexy Blonde Trans Trap Girl Fucking Sissy Slut Ass Glass Dildo Whore
4 years ago
0:59

PornHub

Super Sexy Blonde Trans Trap Girl Fucking Sissy Slut Ass Glass Dildo Whore

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Sissy Makeover: Feminization transformation - Makeup, Wig, Lingerie and Dildo Sucking by Nikki Kit
3 years ago
1:19

PornHub

Sissy Makeover: Feminization transformation - Makeup, Wig, Lingerie and Dildo Sucking by Nikki Kit

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Blonde Tranny Trap Fucks Her Ass With Huge Purple Dildo Sexy Sissy Slut
4 years ago
0:59

PornHub

Blonde Tranny Trap Fucks Her Ass With Huge Purple Dildo Sexy Sissy Slut

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Amateur sissy fucks ass with dildo, whips clitty around in chastity and has sissygasm cum
3 months ago
8:15

xHamster

Amateur sissy fucks ass with dildo, whips clitty around in chastity and has sissygasm cum

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Angel black chained to bed listening to sissy brainwashing
4 years ago
0:43

PornHub

Angel black chained to bed listening to sissy brainwashing

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Proper sissy orgasm in chastity, vibrator on clity, fucking machine in ass
4 years ago
2:06

PornHub

Proper sissy orgasm in chastity, vibrator on clity, fucking machine in ass

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Sissy's Electric Training - Star Nine Femdom POV Electric Play Trailer
5 years ago
0:54

PornHub

Sissy's Electric Training - Star Nine Femdom POV Electric Play Trailer

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using a smaller dildo in me while wearing a sissy pink chastity cage
4 years ago
1:36

PornHub

using a smaller dildo in me while wearing a sissy pink chastity cage

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Sissy in heat fucking her ass with dildo in the streets at night
5 years ago
1:52

PornHub

Sissy in heat fucking her ass with dildo in the streets at night

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Mistress Mercer HUGE DILDO and Speculum DOMINATION Anal Orgasm GAPING SISSY and THROATFUCK
3 years ago
1:30

PornHub

Mistress Mercer HUGE DILDO and Speculum DOMINATION Anal Orgasm GAPING SISSY and THROATFUCK

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anal training sissy faggot femdom strapon hard fucks slave's ass makes him eat own cum CEI
3 years ago
15:25

PornHub

anal training sissy faggot femdom strapon hard fucks slave's ass makes him eat own cum CEI

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Sissy in chastity sucking and fucking her dildo in stockings and suspenders
4 years ago
8:53

PornHub

Sissy in chastity sucking and fucking her dildo in stockings and suspenders

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