SHEMALE • CHASTITY 4,321 videos

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25:01

Crossdresser fuck dildo with chastity cage

4 years ago

xHamster

dildo, chastity
05:29

Shemale in a chastity cage, exploring sissy chastity vibes

9 months ago

XXXVogue

chastity, sissy
05:30

Black TS Chastity cums on her mans face

11 years ago

AShemaleTube

ebony, chastity
10:48

SisK unleashes her pecker from chastity implement and plays with her horny penis after her ass is being plugged.

1 year ago

ShemaleMovie

toys, chastity
06:06

Chastity contraption with ass Plug Attachment

2 years ago

ShemaleTaxi

BDSM, taxi, chastity
16:53

Daniela Lei chastity caged on fuck machine

1 week ago

TrannyGem

boots, italian, chastity
01:09

Dildo fuck in chastity

5 years ago

xHamster

chastity
30:20

Femboy chastity dildo riding!!

1 year ago

AShemaleTube

stockings, femboy, chastity, dildo, homemade, sissy
08:53

Trans chick riding Bad Dragon opportunity in Chastity

2 years ago

ShemaleTaxi

chastity
10:27

Ass-fuck ejaculations In Chastity Cage - Sissy super-bitch Jessica Bloom

2 years ago

ShemaleTaxi

fisting, dildo, chastity
02:30

Banging my femboy whore

2 years ago

TrannyGem

strapon, chastity, femboy
03:18

Sissy Princess - Chastity Training

2 years ago

HClips

train, chastity
23:48 46%

Pink Mercy Trap in Chastity doing Deepthroath and Anal Play

6 years ago

TrannyGem

italian, dildo, erotic, cosplay, chastity, sensual
02:42

Sissy Fuckslut Jessica Bloom Roped Up And Used in The Forest

1 year ago

TrannyGem

femdom, public, outdoor, bondage, dildo, british, swallow
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
05:29

Misty Cane mammories & rump in chastity

8 months ago

ShemaleMovie

POV, chastity
10:00

Pale femboy trap in striped stockings beats own balls escapes chastity and rubs her little cock to a limp hands free cum

2 years ago

xHamster

orgasm, hands free, chastity, femboy
12:42

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

4 weeks ago

ShemaleMovie

feet, fat, huge dildo, anal, orgasm, japanese, dogging
06:57

You wont be able to break out of your chastity device

1 year ago

ShemaleTaxi

chastity
24:11

Asian Femboy In Cheongsam Tries Out The New Horsecock Dildo With Chastity Cage Cums 3 Times

4 years ago

ShemaleZ

chastity
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
12:23

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

3 years ago

TrannyGem

train, 18, old and young (18+), machine, chastity
05:47

PorchaeTS shoots a load in chastity from 11 & 12 inch Lovetoy faux-cocks.

2 months ago

ShemaleMovie

chastity, crossdresser
04:58

Sasha Toys Ass Locked In Chastity

4 years ago

ShemaleZ

chastity
11:58

Sissy Lucy In Chastity With The Fucking Machine

2 years ago

ShemaleZ

chastity
19:06

Sissy Femboy In Chastity Taking Big Dildos In Her Ass And Trying And Sissygasm

3 years ago

HClips

chastity
09:35

Virginity femboy palys with his nads and vag

1 year ago

TrannyGem

feet, cute, dildo, 18, glasses, riding, chastity
07:39

Slytherin Bi-Atch Cast Some Spells, Drills Her Tiny Arsehole, & Makes Cummies!

2 years ago

TrannyGem

chastity, femboy
49:11

Podcast Ep13: Sissy, Chastity and Lust

5 years ago

xHamster

chastity
02:58

Unlocking chastity in public restroom

2 years ago

xHamster

public, chastity
04:55

Slave Chastity Get Fuck

2 years ago

ShemaleZ

domination, chastity, teen (18+)
08:12

Cumming in chastity with E-stim

2 years ago

xHamster

chastity
05:03

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

3 years ago

ShemaleZ

feet, shaving, slut, chastity
03:02

Fat Sissy light ball torture and wax play in chastity

2 years ago

xHamster

fat, german, BBW, chastity
05:48

Crossdressing sissy frigging her arse, fucking a big dildo then ripping off her chastity cage for 2 huge cumshots

2 months ago

ShemaleTaxi

latex, sissy, crossdresser, chastity, huge dildo
04:47

Erika Oak Cums in Chastity

2 years ago

xHamster

chastity
04:13

Sissy Locks Her Cock In A Chastity Cage

3 years ago

HClips

chastity, teen (18+)
12:24

Chastity Slut In Black Stockings And Lingerie Playing

3 months ago

HClips

shemale, chastity, solo, mature
04:34

Edging Herself To Numerous Wrecked Ejaculations

1 week ago

TrannyGem

prostate, squirt, chastity
03:07

18 year old puppy femboy in chastity has first anal orgasm

2 years ago

xHamster

orgasm, ladyboy, anal orgasm, chastity
07:50

Phat Rump Tgirl Phat Ass White Girl Porking Machine in V-Card

2 years ago

TrannyGem

interracial, BBC, chastity, shemale and girl
02:26

Plugged and encaged superb gal sissy

3 years ago

TrannyGem

bondage, panties, chastity
23:19

Ghotic trap solo in chastity

6 years ago

ShemaleZ

chastity
11:24

Chastity sissy rides a big dildo

2 years ago

XXXDan

dildo, chastity, solo
04:04

AB078 圣诞企划-我的奴隶工程师-贞操锁强取和画筐绳缚

5 months ago

TrannyGem

femdom, fetish, bondage, japanese, chinese, nylon, chastity
09:15

Sissy anal training in chastity with a fucking maschine

1 year ago

xHamster

sissy, chastity
05:16

Trans gal in plane virginity cell tugging with stimulating electro-hitachi

5 months ago

TrannyGem

chastity, amateur, vibrator
12:33

Costume Play Óbito Uchiha Crossdreser Maid

7 months ago

TrannyGem

teen (18+), fetish, teen anal (18+), maid, 18, anime, cosplay
04:02

Slimsissyjessica fucks with dildo in motel in chastity belt

1 year ago

JizzBunker

pantyhose, huge dildo, hotel, chastity
06:09

Sissy in vapid v-card box smashed moist and then gets jizz shot in her face

2 years ago

TrannyGem

sissy, chastity
07:19

Trans Woman In Bondage And Chastity Masturbating With Guy 12 Min

1 year ago

GetTranny

bondage, BDSM, chastity, latex
07:41

Crossdresser in Chastity Puts on Lingerie

3 years ago

xHamster

chastity
08:18

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

1 year ago

xHamster

swallow, cumshot, vibrator, chastity
08:25

Dominatrix pokes handsome Sissy in chastity

2 years ago

ShemaleTaxi

bondage, chastity
10:26 86%

Femdom Mistress Pegs Sissy Cuckold Chastity Slut & Makes Her Love Big Cock! Anal Plug Gaping Part 3

2 years ago

ShemaleZ

femdom, BDSM, cuckold, pegging, chastity
10:07 67%

Sissy CD Self-frigging and Fuck Stick Drilling in Taut Denim and V-Card

5 years ago

TrannyGem

feet, chastity, crossdresser
02:42

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

2 years ago

TrannyGem

chastity
08:43

Angel Black wish sissy encouraged to take viagra and in purity

3 years ago

TrannyGem

femdom, public, JOI, chastity
03:11 71%

51cm John Thomas Henry Humungous Assfuck Destruction Fuck Stick Slamming Deep into Slick Nice Femboy Asspussy

2 years ago

TrannyGem

huge dildo, dildo, hardcore, chastity
01:26

Caged anal fun

3 years ago

xHamster

handjob, teen anal (18+), 18, BBC, chastity, femboy
24:18

Sissy purity 10/12/2022 Transgender gimp submission lock up iron cell

4 months ago

TrannyGem

sissy, chastity, old and young (18+)
03:03

Sissy Femboy Trap Crossdresser - Slapping - jism - Purity climax - sissygasm - Forearms Free-For-All climax

3 months ago

TrannyGem

sissy, cute, hands free, femboy, crossdresser, chastity
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

4 years ago

AShemaleTube

femdom, latex, chastity
24:45

Astrid Apathy Puts On Erotic Show In Thigh High Socks And Chastity

3 years ago

ShemaleZ

socks, erotic, chastity
03:53

Trans Teenie rails gigantic ten inch faux-cock

3 years ago

TrannyGem

huge dildo, teen anal (18+), 18, chastity
03:11

TGIRLS.PORNO: Zariah Takes Genesis Chastity

2 years ago

KeekAss

lesbian, small tits, chastity
05:42

Sissy in chastity in black lingerie and stockings riding 12.5 inch circumference dildo

2 years ago

xHamster

chastity
13:40

Latex Sissy In Chastity Anal Play With Big Dildos

4 years ago

ShemaleZ

latex, chastity
01:25

Kelli bathroom Deepthroat

2 years ago

xHamster

small cock, british, thong, bathroom, chastity
06:27 89%

Machine Porked Till She Pops In Her Underpants 4K

1 year ago

TrannyGem

pantyhose, squirt, prostate, panties, machine, anal orgasm, hands free
10:27

Exclusive Full version of Sissy Schoolgirl in the Chastity Cage was humped with a fat fake penis

3 years ago

ShemaleTaxi

fat, chastity
20:52

Fucking Trans Woman in Chastity - Compilation 10

5 days ago

$$ FapHouse

chastity, sissy
06:20

Captive life, peeing in prison

2 years ago

xHamster

pissing, chastity
05:07

Yummy black tranny Chastity Michaels gets her tight ass pounded

11 years ago

AShemaleTube

tight, chastity
08:31

Pink small limp clitty in a smallest chastity cage kiss

1 year ago

AShemaleTube

kissing, chastity
03:22

SDS Chastity Caged at Bedtime

6 years ago

ShemaleZ

chastity
14:40

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

2 years ago

TrannyGem

chastity
06:52

Sissy Swallows Her Own Cum in Chastity After Using Dildo

3 years ago

xHamster

huge dildo, 18, swallow, chastity, cum in ass
07:40

Trans goth bbgirl adaklein wants your cum so bad

1 year ago

xHamster

masturbation, goth, BBC, chastity, femboy
06:31

Lily Leigh Cam Show - November 24th, 2023 (Part 2) - Chastity Cage, fuck stick & getting off intimate Show

1 year ago

ShemaleTaxi

chastity
08:01

Sexy Crossdresser Chastity Dildo Orgasm

5 years ago

xHamster

orgasm, chastity
10:11

Cute Blonde Trans Solo

1 year ago

TrannyGem

chastity, solo, sissy
05:45

Crossdresser Anani mischievous guys Daughters midbody Bull Bull Acme (Chastity Belt + Piston Machine)

4 years ago

ShemaleTaxi

machine, chastity
14:21 67%

New Boots and Armbinder - Sissy Maid Stuck in Bondage Again

1 year ago

xHamster

latex, bondage, boots, BDSM, chastity
05:19

Busty ebony shemale boinking boy

3 years ago

ShemaleTaxi

domination, hardcore, chastity
08:30

Mistress fucks a sissy in the chastity with the red assfuck buttplug

3 years ago

ShemaleTaxi

femdom, taxi, chastity
16:14

Crossdresser gets machine fucked with XXL Monster Dildos #9

1 year ago

xHamster

german, crossdresser, machine, skinny, chastity, femboy
05:19

Sissy Lucy getting pegged in Chastity with the Beastli dildo

4 years ago

TrannyOne

pegging, sissy, chastity
12:16

Sissy verge,hurt & collar your white testicles for BNWO white extinction angel Scarlett black

3 years ago

TrannyGem

chastity
01:05

Maid Dress & Chastity Cumshot

2 years ago

xHamster

maid, dress, chastity
02:30

Chastity Latex

6 years ago

xHamster

latex, vintage, chastity
06:44

Cumming Sissy Slut Anal Masturbation

3 years ago

BeMyHole

fetish, fisting, clit, jerking, toys, slut, chastity
21:51

Self Suspension Bondage - Sissy Maid

2 years ago

xHamster

latex, bondage, maid, chastity
03:23

Young 20 years engaged losing his chastity had never had fuck-a-thon in his life (Utter movie on Crimson)

4 years ago

TrannyGem

orgasm, chastity
06:17 71%

Femboy Booty Spread by Monster BIG BLACK COCK Fake Penis

1 year ago

TrannyGem

BBC, chastity, machine
07:59

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

2 years ago

GetTranny

cum in mouth, chastity, shemale and girl
03:10

Sissy Susi dehnt Ihre Pussy mit Plug. Mit Chastity

4 years ago

AShemaleTube

chastity
05:43

Abh052 in chastity prostate rubdown and incontinence twice

2 years ago

ShemaleMovie

massage, chinese, chastity
04:17 67%

(Part 2) Skinny Asian Sissy Cum Twice After Locked In Chastity For A Week

2 years ago

xHamster

handjob, chastity
11:01

Desperately trying to sissygasm with my limp clitty. Chastity training is so worth it for a sissy

3 months ago

AShemaleTube

sissy, amateur, chastity
06:42

Walking in chastity cage and buttplug

5 years ago

AShemaleTube

outdoor, chastity
04:41

Finally Soaking Sissy Training In Chastity Riding Dildo

2 years ago

ShemaleZ

chastity, vintage
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
03:13

Hot Blonde Trans Bailey Wilde Fucked in Chastity

1 year ago

xHamster

amateur, crossdresser, blonde, sissy, chastity, femboy
06:18

Chastity Keyholding Goddess

3 years ago

GetTranny

chastity, latex
08:55

Sexy Trans Woman in Chastity Gives Blowjob

2 years ago

xHamster

chastity
04:04

Good-Sized Meatpipe Transgender Princess Toying in Innocence

3 years ago

TrannyGem

18, vibrator, chastity
06:14

Sissy Guide - How to Anal Orgasm in Chastity Cage - Jessica Bloom

1 year ago

xHamster

sissy, chastity, prostate
04:28

Sissy ravage a fake penis

1 year ago

TrannyGem

sissy, chastity
06:59

Chastity Femboy Teasing Cage With Wand

3 years ago

GetTranny

chastity
07:33

Full time chastity

8 years ago

TXXX

latex, chastity
09:43

The Lost Chapters pt three - Accomplished Nymph Takes Dolls Chastity by Foxie2K

2 years ago

TrannyGem

anime, cartoon, chastity
15:47

Sissy instructing

4 years ago

TrannyGem

femdom, train, instruction, vibrator, boyfriend, chastity
03:01

SISSY ANAL STRETCHING

2 years ago

xHamster

squirt, fisting, hands free, chastity
10:21

Chastity sissy fucktoy for bbc

2 years ago

ShemaleMovie

chastity
01:17

Sissy In Chastity showing off my Big Thick Ass and outfit

2 years ago

xHamster

chastity
05:21

Sucking Boys manhood Before Taking His anal chastity

10 months ago

HDSex

big cock, shemale fucks guy, chastity, shemale
07:05

Alexa fucking ass-pussy with large Beowulf in chastity & corset

2 years ago

xHamster

german, chastity
07:16

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

1 year ago

ShemaleTaxi

sissy, small cock, masturbation, chastity
09:45

Supah wondrous Blonde Femboy Removes Chastity Then strokes Off

1 year ago

ShemaleTaxi

femboy, chastity

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