SHEMALE • CHASTITY 4,320 videos

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17:10 17%

Man Masturbates Off with Trans Lady in Purity

7 months ago

TrannyGem

handjob, bondage, BDSM, crossdresser, babe, chastity, femboy
21:51 14%

Submissive Sissy Chastity Buttplug Play

6 years ago

ShemaleZ

BDSM, ass, toys, chastity, crossdresser
28:30 10%

Can You Treat Your Keyholders Gifts? - Ass-Fuck Have Fun, Feminization, Purity Praise RP

1 year ago

TrannyGem

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08:35

Your Girlfriend paid a hot trans leather dyke and blonde bombshell to lock you in chastity

2 weeks ago

AShemaleTube

shemale, chastity, sissy, girlfriend, leather
09:03

Goth tgirl Kendal Uwu in latex and chastity trying to free her forearms while getting off

2 weeks ago

XXXVogue

stockings, chastity, goth, latex, dildo
10:00

Extraordinary Natural Tits Tgirl with a chastity cage Chapter 2

1 week ago

AShemaleTube

small tits, solo, chastity, webcam
07:13

Trans girls Jessica Bloom and JenbyDoll share a massive load while locked in a chastity cage

1 week ago

XXXVogue

chastity, cum in mouth, amateur, blowjob
10:45

SISSY Buttfuck Instructing by SPANDEX Domme

5 days ago

TrannyGem

crossdresser, femboy, chastity, amateur, femdom, latex, sissy
05:41

Sissy String-on Spitroast in Virginity Pegged by Wonderful female dom Couple by Domme Mercer

1 month ago

TrannyGem

femdom, strapon, threesome, couple, fetish, double anal, pegging
21:22

Ilandis in a purity belt has joy with her ass-hole using different playthings

1 week ago

TrannyGem

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02:20

Trans Nymph Porked in Virginity

2 weeks ago

TrannyGem

ass, crossdresser, bondage, fetish, BDSM
07:50

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2 years ago

TrannyGem

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11:07

Sissy Lucy Loced down in iron chastity and chains

1 month ago

ShemaleTaxi

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16:53

Daniela Lei chastity caged on fuck machine

5 days ago

TrannyGem

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05:10

Year Long Chastity Release Shemale Femdom Foot Worship Anal Pegging and Face Fucking

1 month ago

AShemaleTube

feet, chastity, femdom
15:54

Crossdresser On Live Webcam - Sissy Wears Chastity Belt

2 years ago

ShemaleZ

crossdresser, blonde, sissy, chastity
09:39

Fucking Machine Anal Orgasms Chastity Foot Slut Jessica Bloom 10 Min

7 months ago

HClips

feet, orgasm, machine, slut, anal orgasm, chastity
07:34

Sissy Juliette in chastity lockdown for 8h. kinky fun with toys all night at home

1 year ago

xHamster

swedish, sissy, chastity, latex, smoking, fetish
13:19

Spreading my caboose and spunking while railing my fresh Big stallion fuck stick

5 days ago

TrannyGem

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26:51

Full: Big Balls Sissy in Chastity Cage Massive Cumshot and Masturbating Her Small Dick Like a Girl

1 week ago

$$ FapHouse

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07:06

Sissy Maid in chastity Takes a enormous ass fucking Creampie For Her Job Interview

1 month ago

ShemaleTaxi

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03:15

Sissy Crossdresser Walking Outside with a Vibrator Inside Her Ass and a Micro Chastity Cage

Yesterday

$$ FapHouse

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03:03

Sissy Haley Dusk rails BIG BLACK COCK fake penis

5 days ago

TrannyGem

crossdresser, black, sissy
15:40

Spunk-Pump Tamer lets their lil pink cigar out and it gets taller into a rock rock hard, vein adorned, pulsating dinky!

4 weeks ago

TrannyGem

cumshot, masturbation, shemale, chastity, pump, goth
07:14

Sissy Marissa cheering for cock

1 year ago

xHamster

bondage, crossdresser, sissy, chastity, dildo
21:47

Shemale maid Mina cums in chastity while railing a immense dildo... Make me clean my own mess parent!

1 week ago

VideoSection

shemale, dildo, chastity
05:25

I cornered my Sissy with my Belt Cock and give a rigid Pegging. Total OnlyFans • FEMFORHER

1 week ago

TrannyGem

pegging, chastity, strapon
03:56

Trans Chick with GIANT DONK Penetrated Without A Condom Doggie-Style

2 weeks ago

TrannyGem

chastity, shemale, sissy, dogging
02:20

Pent Up in a pinkish bathing suit and virginity cell

1 month ago

TrannyGem

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12:25

Whorey Trans Bunny Lilith Eclipse Bangs Herself With Carrots In Innocence Arse To Hatch

3 months ago

TrannyGem

ass to mouth, amateur, chastity, shemale, sissy, fisting
15:56

RUSSIAN FEMBOY HUMPS WITH DOMME FOR THE FIRST-EVER TIME WITH A IMMENSE BELT DICK, STRAPPED WITH A INNOCENCE

4 years ago

TrannyGem

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05:33

Sweet Chastity 8 - Abby Kitty

2 days ago

AShemaleTube

shemale, chastity
20:52

Fucking Trans Woman in Chastity - Compilation 10

3 days ago

$$ FapHouse

chastity, sissy
12:42

I moaned loud when I boinked by a fat dildo in a standing doggy position with chastity box on

3 weeks ago

ShemaleMovie

feet, fat, huge dildo, anal, orgasm, japanese, dogging
19:19

Sissy Marcellas gets filled with faux cocks in a pop-shot chastity scene

1 month ago

XXXVogue

anal, fisting, sissy, chastity, dildo
03:17

Cute Young Trans-Girl in Chastity Takes BBC Dildo and Horse-Dildo - Sloppy Anal

6 months ago

AShemaleTube

shemale and girl, BBC, solo, chastity, dildo, cute
01:05

MATURE CROSSDRESSER TVROSE CUTE PINK CHASTITY CAGE PERT NIPPLES SEXY BLACK DRESS

2 years ago

xHamster

mature, cute, black, POV, MILF, nipples, dress
1:16:10

Pov cuckold 14 candy manson cuckolds her husband and locks him in chastity makes him watch her fuck a big cock and eat the creampies and has sex with him after

3 years ago

TrannyOne

cuckold, husband, chastity
11:28

Shemale Blowjob Delia Releases A Kept Man From Chastity Then Locks Him Down With Her Cock

4 years ago

BeMyHole

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07:36

Chastity desire, Gudrun and Angie

5 years ago

xHamster

mature, mature anal, chastity
08:31

Sissy in chastity cage cums hands free while riding big black dildo

7 years ago

ShemaleZ

dildo, sissy, hands free, chastity
02:02

Using my magic wand to jizz thru my virginity cell

5 days ago

TrannyGem

shemale
10:03

Surprise sleep mask poke with 2 t-model bombshells

6 months ago

TrannyGem

chastity, domination, shemale fucks guy, amateur, surprise, sleeping
29:22

Imagining Im a Femboy make me Spreading Anal Invasion again

1 year ago

TrannyGem

teen (18+), teen anal (18+), 18, chastity
01:41

Sissy Oksana2021 uses a huge 3.34" anal plug_2

2 years ago

xHamster

chastity
13:39

Connie Cage Trains and Leaks for her Owners

5 years ago

TrannyGem

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05:40

Maureennadh - Hijab Sissy Squirt While Anal Training Using Chastity Cage

1 month ago

$$ FapHouse

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10:41

Losing Her chastity in a twat -Cliff Media

2 months ago

ShemaleTaxi

chastity, strapon, czech, gloryhole
10:40

Luci Belle And Rachael Belle - Trans Chastity Beauties Tease With Toys

2 months ago

ShemaleZ

stockings, chastity
08:58

How my Dominant Wife and her BBC Lover Persuaded me into a Shemale Relationship (Chastity Femdom}

5 years ago

BeMyHole

femdom, wife, chastity, shemale fucks guy
11:46

Chastity Sandy Fucked Hard

8 years ago

xHamster

teen (18+), chastity
02:32

Ass-Plug it in, Cork it in

4 weeks ago

TrannyGem

shemale, chastity, crossdresser, sissy, blonde, femboy
05:46

Indian transgender princess disrobe taunt bare dance in hindi marvelous music flick

1 year ago

TrannyGem

chastity, femboy, indian, slut, dance, crossdresser
04:46

She Gets Continuously Romped To An Explosive Ejaculation

3 years ago

TrannyGem

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08:09

Chastity Sissy Cums From Big black pipe plumbing Machine And Swallows Her Own Cum

2 months ago

ShemaleTaxi

black, machine, chastity, cum in mouth
07:15

Sissy Maid jizzing in chastity During Self bondage

4 months ago

ShemaleMovie

amateur, chastity, crossdresser, dildo, bondage
06:24

Daddy Loves to Wreck My Asshole in Chastity

5 months ago

$$ FapHouse

BBC, creampie, chastity, big cock, asshole, colombian
20:08

Luna locked in a chastity cage indulges in her desires and reaches climax

10 months ago

XXXVogue

chastity
09:43

Vibrating my clit, chastity fail ends in self suck!

1 year ago

xHamster

facial, selfsuck, cum in mouth, vibrator, chastity
07:34

Violet Chastity Chained to Fuck Machine

1 year ago

xHamster

homemade, bondage, cuckold, machine, gape, chastity
07:59

Raver Sissy Femboy In Chastity Fucks Bbc 4 Femdom Goddess While She Eats Dinner, Rough Anal Slut 4/5

2 years ago

GetTranny

femdom, chastity, femboy
02:12

Putting on a chastity

2 years ago

xHamster

bondage, BDSM, chastity
31:05

Crossdresser Femboy Sissy-kat Gapes With A Bbc Dildo And Leaks In Chastity

2 years ago

ShemaleZ

dildo, chastity, femboy, sissy
32:11

Lizzy Yum August 2022 #8 SEX MACHINES, EROTIC ELECTRICITY & BSDM-CHASTITY

3 years ago

xHamster

mature, mature anal, BDSM, erotic, machine, chastity
04:13

Sissy crossdresser in chastity gets pounded hard by a fucking machine

3 years ago

TrannyOne

machine, chastity
20:08

Sissy Maid Self Bondage in Spiked Chastity Cage

3 years ago

xHamster

latex, bondage, maid, chastity
08:29

Crossdressing School Girl Putting on Chastity

3 years ago

xHamster

femdom, chastity
01:17

Emily Austin cuckold creampie eating hot wife sex puts sissy into chastity

4 years ago

TrannyOne

wife, cuckold, cum in mouth, chastity
05:24

Sissy Melissa getting an Orgasm in her Chastity Cage.

5 years ago

xHamster

femdom, orgasm, BDSM, chastity
06:26

Walking in chastity cage and buttplug

11 years ago

xHamster

chastity
07:31

Femboy streamer violates terms of service

2 weeks ago

TrannyGem

ass, behind the scenes, femboy, fisting
05:52

Dressed In Tght Virginity Box and Sate Shaft with a Magic Wand Until Unleashed and Pulverize Bang-Out Fucktoy Muff

2 weeks ago

TrannyGem

shemale, sissy, chastity, goth
07:23

-Futa 2B Porks femboy 9S In Innocence (Futa on Masculine)

3 months ago

TrannyGem

femdom, 3D, game, anime, cartoon, futanari, cosplay
06:18

REAL Discipline of gimp masculine: Soap in Jaws, STIFF Smacking, Highly Spoken Dominatrix

6 months ago

TrannyGem

chastity
07:35

Violet virginity fettered to smash Machine

11 months ago

ShemaleMovie

machine, cuckold, chastity, bondage
07:55

Sissy Candy in Lingerie Gets Fucked by Her Machine with a Huge Dildo

12 months ago

xHamster

huge dildo, dildo, lingerie, crossdresser, machine, chastity
06:47

Sis-k Pinky Chinese Dress Ep3: Fapping

1 year ago

xHamster

thai, chastity, small cock, solo, chinese
16:14

Crossdresser gets machine fucked with XXL Monster Dildos #9

1 year ago

xHamster

german, crossdresser, machine, skinny, chastity, femboy
07:40

Trans goth bbgirl adaklein wants your cum so bad

1 year ago

xHamster

masturbation, goth, BBC, chastity, femboy
10:31

Trans doll attempts on trio different v-card belts and blows a load arms free-for-all

1 year ago

TrannyGem

pissing, teen (18+), anal, fetish, teen anal (18+), orgasm, sissy
10:20

Rectal Progression Update

1 year ago

TrannyGem

stockings, dildo, riding, masturbation, toys, chastity
08:46

Fat BBC dildo fills Sissy ass deep

1 year ago

xHamster

fat, dildo, toys, chastity, femboy, BBC
08:12

Sisk Try on Her Colorful Sissy Panties Collection

1 year ago

xHamster

small cock, asian, panties, chastity
06:09

Sissy cheerleader balls deep!

2 years ago

xHamster

dildo, cheerleader, chastity, crossdresser
19:11

Latex Slave Takes Fuck Machine

2 years ago

BeMyHole

feet, latex, fetish, bondage, boots, BDSM, jerking
17:06

Cutie assistant public remote manage

4 years ago

TrannyGem

public, secretary, vibrator, chastity
08:35

Ultra-Cute Sissy College Girl Assfuck with Foxtail & Chasity & Chat

4 years ago

TrannyGem

college, cosplay, chastity
16:58

Fucking-machines Fucks TS-Girl in the Doggystyle, Ass Cum + Cock Cage

6 years ago

TrannyGem

huge dildo, russian, machine, clothed, chastity, cum in ass
12:10

Sweet Chastity 4

2 days ago

AShemaleTube

shemale, chastity
07:00

Slow blow-job from Sissy CD in chastity

1 month ago

ShemaleMovie

amateur, crossdresser, cum in mouth, blowjob, sissy, chastity
09:28

Bailey Wilde And Chisholm Of Boston In Hot Trans Fucked In Chastity

1 month ago

HClips

18, amateur, chastity
07:59

Chastity Compilation Trans And Sissy Girls Locked And Fucked

1 month ago

PePorn

shemale and girl, compilation, chastity, skinny
06:15

Trans pissing over prolapped ass with chastity locked cock

2 months ago

TXXX

chastity, pissing, masturbation, big cock, fetish
12:24

Chastity Slut In Black Stockings And Lingerie Playing

3 months ago

HClips

shemale, chastity, solo, mature
05:54

Fucked a BBC dildo until I cum in my chastity cage

4 months ago

AShemaleTube

mature, shemale, mature anal, crossdresser, BBC, sissy, chastity
08:00

Cute Femboy Fucks Big Cock In Chastity Cage And Cums Hot

9 months ago

xShemaleTube

amateur, shemale, chastity
07:12

Teen (18+) mastering chastity orgasm while locked in a chastity cage

10 months ago

XXXVogue

chastity
10:25

Chastity Sissy Dildo Riding Anal climaxes Using spunk As lube - Jessica Bloom

11 months ago

ShemaleMovie

shemale, fisting, dildo
13:35

Taunted Trans damsel chastity and Anal Play

1 year ago

ShemaleMovie

stockings, train, dildo, 18, vibrator, chastity
05:38

Trans sissy slut with blue hair going crazy with big dildos - MercurySissy aka Mercury Montana riding and training in chastity

1 year ago

xHamster

dildo, masturbation, chastity, femboy
25:04

Sissy Maid Collared to Bedpost in Spiked Chastity Cage and Handcuffed Harness Gagged

1 year ago

xHamster

bondage, BDSM, sissy, chastity, dildo
03:13

Hot Blonde Trans Bailey Wilde Fucked in Chastity

1 year ago

xHamster

amateur, crossdresser, blonde, sissy, chastity, femboy
09:53

Hot TS Bailey Wilde Removes Chastity Then Jerks Off

1 year ago

xHamster

BDSM, big cock, chastity, femboy
25:26

Made My Chastity Cage Sissy Transgender Femboy To Cum In My Mouth!

2 years ago

ShemaleZ

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03:07

18 year old puppy femboy in chastity has first anal orgasm

2 years ago

xHamster

orgasm, ladyboy, anal orgasm, chastity
02:31

Horny Latex Slut Locked In The Inverted Chastity Cage

2 years ago

xHamster

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02:45

Strap-on Fuckers: Sissy Slut in Chastity Used by Her Domina

2 years ago

xHamster

femdom, strapon, chastity
09:15

Transvestite Ananny Mass Leak + Nipple Messing (chastity Belt + Piston Machine)

2 years ago

ShemaleZ

nipples, machine, chastity
03:08

HUGE ASS TS in Chastity Fucked Missionary

2 years ago

xHamster

missionary, chastity
08:27

Chastity Slave Loves to spread

2 years ago

xHamster

chastity
04:35

Trans Girl Fucking Her Ass While Wearing A Chastity Cage (short Version)

3 years ago

ShemaleZ

chastity
09:12

Fucking Myself With A 10 Inch Cock While Locked In Chastity

3 years ago

ShemaleZ

chastity
06:52

Sissy Swallows Her Own Cum in Chastity After Using Dildo

3 years ago

xHamster

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02:15

Sissy prostate cumshot in steel chastity

5 years ago

AShemaleTube

prostate, uniform, sissy, chastity
08:33

Lilac Angora Tiny Chastity Huge BBC - Drip Milk Sissygasm

5 years ago

xHamster

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15:35

I will be the one to take your she-male chastity

5 years ago

ShemaleMovie

bisexual, hardcore, chastity, black
09:38

Beautiful Sissy in chastity enjoys being fucked

6 years ago

xHamster

beauty, chastity, sissy
07:01

One of the best bitch in chastity suck a dick in public

6 years ago

ShemaleZ

mature, public, chastity
03:20

Assfucking the Easter Bunny - Liza fucks Sasha in humiliating strap-on chastity video

6 years ago

AShemaleTube

strapon, ass to mouth, chastity
14:50

Real sissy slut anal in chastity cage

11 years ago

xHamster

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