SHEMALE • CHASTITY 3,844 videos

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02:42

Chastity slave get milked while licking trannys feet

2 years ago

xHamster

feet, femdom, bisexual, milk, chastity
20:12

Sissy Maid Cuffed Spread Eagle in Steel Chastity Belt and Huge Dildo

2 years ago

xHamster

latex, huge dildo, fetish, maid, chastity
05:41

Cindy love anal in chastity

3 years ago

xHamster

british, chastity
05:16

Lily Starlets Huge Sissygasm Drizzle on the Douche Floor

4 years ago

TrannyGem

squirt, teen anal (18+), orgasm, bondage, BDSM, hands free, chastity
11:18

Trans Women Use Dildo, Butt Plug, Vibrator, Chastity and More

5 months ago

xHamster

dildo, cumshot, handjob compilation, cumshot compilation, chastity
05:10

Brandie Flashback: July 2023

8 months ago

TrannyGem

amateur, homemade, solo, chastity
02:14

Shaggy Fucks Tgirl in Chastity

1 year ago

xHamster

chastity
14:55

Lanas Weekly Ass-Fuck Lesson

3 years ago

TrannyGem

femdom, russian, fisting, chastity
03:02

Fat Sissy light ball torture and wax play in chastity

1 year ago

xHamster

fat, german, BBW, chastity
05:31

I will tease your manmeat while you are locked in chastity

8 months ago

ShemaleTaxi

chastity
04:13

Sissy Locks Her Cock In A Chastity Cage

2 years ago

HClips

chastity, teen (18+)
07:01

Desperate sissy attempts to cum fter week in chastity

4 years ago

HClips

chastity, 18
03:11

Machine Smashed Firm On Her Knees

1 year ago

TrannyGem

dildo, machine, hands free, chastity
05:48

A girl in black footwear penetrates a man in a chastity belt hard

1 year ago

ShemaleTaxi

taxi, chastity
06:48

Sissy femboy caged in flat cage

1 year ago

xHamster

latina, mexican, chastity
06:27

Machine Porked Till She Pops In Her Underpants 4K

2 months ago

TrannyGem

pantyhose, prostate, cumshot, panties, machine, anal orgasm, hands free
06:28

My latex girlfriend makes me vibrate in a cage

3 months ago

xHamster

amateur, latex, chastity, BDSM, bondage
10:45

Plane encaged sissy splatter

4 months ago

TrannyGem

squirt, fetish, asian, orgasm, masturbation, vibrator, sissy
29:32

Jism from every Fuckhole

4 years ago

TrannyGem

latex, rubber, doll, orgasm, anal orgasm, chastity
04:58

Sasha Toys Ass Locked In Chastity

3 years ago

ShemaleZ

chastity
05:12

Sissygasm on huge deep toy in chastity

1 year ago

xHamster

pissing, hands free, chastity
01:32

Frat College Guy Fucks Trans Woman in Chastity

1 year ago

xHamster

college, chastity
10:53

Sexy Sissy In Chastity Sexyasiansissy

2 years ago

Upornia

chastity
02:26

Plugged and encaged superb gal sissy

2 years ago

TrannyGem

bondage, panties, chastity
05:15

SISSY SLUT SHOWS OFF AND PUSHES OUT BUTT PLUG

11 months ago

xHamster

pantyhose, teen (18+), teen anal (18+), crossdresser, sissy, chastity
13:13

Sissy in chastity and undergarments in a training session

2 years ago

ShemaleTaxi

train, BDSM, chastity, crossdresser
02:58

Unlocking chastity in public restroom

1 year ago

xHamster

public, chastity
09:29

Hotwife Fucks Her BBC Bull As Sissy Cuckold In Lingerie And Chastity Cage

5 years ago

ShemaleZ

cuckold, chastity
20:10

SISSY SHOOTS A LOAD IN V-CARD AFTER five DAYS OF V-CARD JIZM IN SHAFT CELL Virginity Jizm Compilation

3 years ago

TrannyGem

orgasm compilation, chastity
05:56

Sissy in innocence cell wants to boink

1 year ago

TrannyGem

korean, chastity
06:10

Trans Kelsey Masters Big donk porked wet While in Chastity

1 year ago

ShemaleTaxi

homemade, chastity
01:03

Playing with my lady balls in chastity

5 years ago

xHamster

couple, chastity
04:09

Hot Sissy in Chastity Strapon Fucked by Dominatrix

1 year ago

xHamster

strapon, chastity, femboy
08:03

Sissy Crossdresser Deep Assfuck Have Fun & Encaged Sissygasms

1 year ago

TrannyGem

anal orgasm, chastity
05:45

Amateur Femboy Tries To Cum Handsfree In Chastity But Gets Impatient And Jerks Off

2 years ago

ShemaleZ

hands free, chastity
02:15

Shaggy Fucks Sexy Trans Woman in Chastity

1 year ago

xHamster

chastity
29:22

Imagining Im a Femboy make me Spreading Anal Invasion again

8 months ago

TrannyGem

cute, teen anal (18+), 18, masturbation, toys, chastity
15:50

Sissy whore teaching in virginity cell and ass buttplug

2 years ago

TrannyGem

whore, chastity
08:31

Trans Woman in Chastity and Bondage Fucked

1 year ago

xHamster

bondage, chastity
01:15

Sissy slut haileydoll in chastity riding bbc dildo

1 year ago

xHamster

chastity
04:57

Ebony Tgirl Chastity thrusts her dick inside her lovers butt

7 years ago

ShemaleZ

interracial, chastity
05:54

Tied up sissy in chastity cage with anal plug ready for fuck

1 year ago

xHamster

french, bondage, tied, chastity
07:35

Hot CD bends over to get her cock with chastity pleasured from behind

4 years ago

BeMyHole

fisting, swallow, chastity
03:05

Prepare my hole for fisting with an inflatable butt plug and chastity cage

10 months ago

XXXDan

anal, fisting, chastity
09:58

Tiffany Minx Chastity Sissy Double stuff bet!

5 years ago

TXXX

double penetration, chastity
04:13

Sissy locks her cock in a chastity cage

2 years ago

xHamster

chastity
02:21

Sexy body stocking yummy tgirl in chastity and riding dildo - 超騷！穿著连身丝袜鎖上貞操鎖女裝大佬射精

5 years ago

AShemaleTube

fetish, chastity, crossdresser, teen (18+)
11:56

Sasha Rose - BBC Chastity Slut

5 years ago

ShemaleZ

slut, BBC, chastity
07:34

Tranny cleans Mistress house in chastity

6 years ago

xHamster

femdom, chastity
09:43

Chastity Sandy fucked hard

5 years ago

ShemaleZ

creampie, ass to mouth, blonde, ass, chastity
10:16

Amazing Shemale in Chastity

4 years ago

TrannyOne

insertion, chastity
07:11

Chastity Anal Orgasms With Huge Dildos Sissy Jessica Bloom

1 year ago

xHamster

huge dildo, anal orgasm, chastity
03:48

Sissy Onyx - First Chastity Cage

3 years ago

xHamster

chastity
26:44

Hot Chastity Sandy.

12 years ago

xHamster

chastity
07:51

Your Emo Sissy GIRLFRIEND taking Mutt Node Deep like a Super-Bitch

8 months ago

TrannyGem

emo, dildo, crossdresser, glasses, goth, toys, sissy
07:18

Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum

7 months ago

AShemaleTube

homemade, swallow, machine, sissy, hands free, chastity, femboy
11:26

FABULOUS CD GIVES a REPORT FOR DOMME IN FRESH HIGH HIGH-HEELED SHOES AND BLACK TIGHTS AND PURITY BELT

3 years ago

TrannyGem

feet, pantyhose, office, heels, behind the scenes, shoes, tight
03:06

ASIANTGIRL - Erotic Striptease On Classy Dress With Sandy

8 months ago

TrannyGem

thai, asian, masturbation, heels, small tits, chastity
20:48

A Sissygasm through Chastity

5 years ago

TrannyGem

orgasm, bondage, BDSM, BBC, chastity
06:20

Crossdresser gets put in chastity for first time

6 years ago

ShemaleZ

first time, chastity
20:59 50%

Sissy Brittanie Masturbates In Chastity To Hypno

3 years ago

ShemaleZ

lingerie, chastity
07:41

Crossdresser in Chastity Puts on Lingerie

2 years ago

xHamster

chastity
05:45

ABH052 fancy she-creature in chastity prostate rubdown and incontinence twice

3 years ago

ShemaleTaxi

pantyhose, prostate, chinese, chastity, teen (18+)
06:52

Sissy Swallows Her Own Cum in Chastity After Using Dildo

2 years ago

xHamster

huge dildo, 18, swallow, chastity, cum in ass
08:01

MercurySissy riding huge toy in chastity - trans sissy slut anal solo

2 years ago

xHamster

train, riding, slut, chastity
01:32

Sissy in Chastity, Sissy Panties, Sissy Tattoo

2 years ago

xHamster

panties, chastity
04:19

Chastity Sissy Elf Plays With A Dildo

5 years ago

ShemaleZ

chastity
17:47

Chastity guide : A review of all metal innocence cages by sissy joyce

3 months ago

ShemaleMovie

sissy, chastity
03:31

Femboy Chastity

3 years ago

ShemaleZ

chastity
01:44

Pizza Delivery Guy Fucks Sexy Trans Woman in Chastity

1 year ago

xHamster

chastity
16:12

Another anal training

1 year ago

xHamster

chastity
14:21

New Boots and Armbinder - Sissy Maid Stuck in Bondage Again

8 months ago

xHamster

latex, bondage, boots, BDSM, chastity
21:51

Self Suspension Bondage - Sissy Maid

1 year ago

xHamster

latex, bondage, maid, chastity
07:14

Anal invasion vibro tranny breezy chastity

8 months ago

ShemaleMovie

shemale, crossdresser, chastity, sissy
01:25

Kelli bathroom Deepthroat

1 year ago

xHamster

small cock, british, thong, bathroom, chastity
02:42

Ali interchanges her daytime ass butt-plug for her night time speculum

1 year ago

TrannyGem

chastity
01:20

Sissy in a Hotel

2 years ago

xHamster

german, hotel, chastity
11:29

Sissygasm - Cageful of Jism

3 years ago

TrannyGem

chastity
14:55

Lana Trap gets unlocked for a surprise oral

2 years ago

TrannyGem

surprise, chastity
02:06

Sissy Lucy gets Pegged in Chastity whilst trying to wash up

3 years ago

xHamster

mature anal, pegging, chastity
07:03

Millie Trying On Panties In Chastity For You!

1 year ago

ShemaleZ

panties, chastity
01:28

Sissy in chastity and bondage has ruined orgasm

6 years ago

xHamster

orgasm, bondage, BDSM, chastity
01:24

Sissy Maid in Chastity Desperate in Bed

2 years ago

xHamster

mom, maid, chastity
06:56

Sissy crossdresser in gas mask and ballet shoes is drilled rigid by machine

3 years ago

TrannyGem

boots, nipples, danish, mask, machine, shoes, chastity
05:03

Feet Toes Ass Chastity Cage Transgender Slut Showing Nude Ass Smooth Shaved Tgirl Gurl With Sissy Slave

2 years ago

ShemaleZ

feet, shaving, slut, chastity
21:40

Sissy fisting Ass rigid in chastity

2 years ago

ShemaleTaxi

anal, fisting, toys, chastity, femboy, crossdresser
03:16

Perfect Sissy in chastity

5 years ago

xHamster

chastity
03:41

Trans Woman Fucked Reverse Cowgirl in Chastity

1 year ago

xHamster

chastity
12:42

Double anal in chastity

8 years ago

xHamster

latex, double anal, double penetration, chastity
01:01

Goddess Violet Presents: The Feminization of M

11 months ago

xHamster

maid, chastity
10:09

Super-fucking-hot blondie Bailey Wilde eliminates Chastity Then Jerks Off

9 months ago

ShemaleMovie

shemale, chastity
07:13

Trans Latex After Cum Sex In Chastity

8 months ago

ShemaleZ

solo, chastity, big cock, fetish
03:13

Ultra-Cute succubus wants to take all your jizm this Halloween. Total on UVIU HornyJohny66

1 year ago

TrannyGem

huge dildo, anal orgasm, chastity
08:18

Sissy in Chastity Cums With Vibrator And Uses Cum as Lube A2M - Jessica Bloom

11 months ago

xHamster

swallow, cumshot, vibrator, chastity
03:38

Sissy boy has multiple sissygasms

11 months ago

xHamster

squirt, cumshot compilation, hands free, chastity
26:04

Sissy in Harness Fumble Herself with Fuck Stick and Rabbit, then Spunk in Innocence

2 years ago

TrannyGem

vibrator, chastity, cum in ass
05:06

Sissygasm in a negative chastity belt

11 months ago

xHamster

BDSM, chastity
19:06

Sissy in chastity swallow cum

6 years ago

ShemaleZ

swallow, chastity
14:40

Alpha masculine pummeling sissy condom-free, blows a load inwards and she commences fapping like a dame in v-card

1 year ago

TrannyGem

chastity
03:25

Sissy dildo fucking in chastity

5 years ago

TXXX

chastity
05:16

Good Bussy

1 year ago

xHamster

ebony, chastity
12:12

Sissy Marissa Plays with Herself

7 months ago

xHamster

shemale, crossdresser, chastity, latex, fetish
05:24

Deep Ass Fucking Pony Salami Faux-Cock Penetrating Machine - Jessica Bloom

3 months ago

TrannyGem

cute, beauty, creampie, huge dildo, orgasm, dildo, cumshot
07:16

Sissy tart slot flash - MercurySissy aka Mercury Montana in chastity showing hole - trans solo

4 months ago

ShemaleTaxi

sissy, small cock, masturbation, chastity
05:46

Teen Sissy Alex In Chastity Plays With Toys

5 years ago

TXXX

chastity
01:57

Kelli makes herself leak with a jewel plug

2 years ago

xHamster

british, chastity
05:44

Good Girls Eat Up All Of Their Cum Even While Locked In Chastity 6 Min

1 year ago

HClips

chastity
08:05

Sissy Gets a Massive Fountain 1

4 years ago

TrannyGem

bondage, slut, chastity, cum in ass
05:31

AB051 Latex sissy in chastity and fucked by Mistress - BDSM乳胶人妖贞操锁被女王用假阳具抽插

3 years ago

AShemaleTube

femdom, latex, chastity
07:05

Candle Wax & Chastity Go Together like PB & Jelly

9 months ago

xHamster

sissy, chastity, small cock
06:53

Mommy Holy - It's Ok The Doctor Said So - a JOI story with a little CEI

4 months ago

xHamster

crossdresser, JOI, pantyhose, mom, chastity
26:45

Naughty Chastity Sandy.

6 years ago

ShemaleZ

chastity
05:07

Hocus Pocus Big Black Dickus

5 years ago

TrannyGem

fat, cosplay, chastity
02:23

Sissy piggy permitted inwards from its pig shed home to neat domme home angel Scarlett black

4 months ago

TrannyGem

black, chastity
05:14

CD-TG Liana Ames Deepthroating Dildo in Chastity

5 years ago

ShemaleZ

deepthroat, chastity
07:10

How to Put on a Chastity Cage and Train Your Ass with a BBC

4 months ago

xHamster

femboy, crossdresser, chastity, BBC
06:19

Mistress Fuck Chastitied Femboy In Lingerie

1 year ago

ShemaleZ

femdom, BDSM, chastity
12:23

Sissy woman ass-fuck trainer with screw machine big black cock faux-cock

2 years ago

TrannyGem

train, 18, old and young (18+), machine, chastity
03:26

Seeing Jism Seep From Her Cock-Squeezing Culo

2 years ago

TrannyGem

squirt, prostate, bukkake, anal orgasm, hands free, chastity
11:58

Sissy Lucy In Chastity With The Fucking Machine

1 year ago

ShemaleZ

chastity

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