SHEMALE • CHASTITY 3,726 videos

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08:48

Hot sissy in tiny chastity cage masturbates with vibrator

1 year ago

xHamster

crossdresser, sissy, chastity
08:32

Horny TS gets her asshole stretched wide by a humongous black dildo

3 years ago

BeMyHole

dildo, BBC, chastity
07:16

Chastity submited and fucked

6 years ago

xHamster

BDSM, chastity
01:54

Pissing nacked outdoor in my tiny chastity

8 months ago

xHamster

pissing, outdoor, bondage, chastity
02:12 75%

Fuck Stick

5 months ago

TrannyGem

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10:48 79%

Jessica Bloom Multiple Caged Assgasms

2 years ago

PornHub

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09:42

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4 years ago

xHamster

maid, small tits, chastity
11:45

Sissy Gurl And Chastity Enby In Chastity Rides Her Pink Dildo

11 months ago

BeMyHole

sissy, chastity
04:35

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

1 year ago

ShemaleZ

chastity
01:02

Instant Sissygasm Hands-free in Chastity

2 years ago

xHamster

mature anal, hands free, chastity
06:51

BBC Ken Fucks Me on My Back in Missionary with Verbal Dom Sissification - Candy Ass Sissy in Chastity Cage

5 months ago

xHamster

BBC, sissy, missionary, chastity
05:23

Pegging And Latex Glove Fisting Slutty Chastity Sissy With Giant Black Dildo By Mistress Mercer

1 year ago

ShemaleZ

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12:18

Enby in chastity rails her rosy fake penis

4 weeks ago

ShemaleMovie

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27:08

Trans Anal Of Chastity Sandy

11 years ago

AShemaleTube

chastity
15:54

Crossdresser On Live Webcam - Sissy Wears Chastity Belt

8 months ago

ShemaleZ

crossdresser, blonde, sissy, chastity
19:33

She Is So Horny That She Got Erection In Chastity

1 year ago

ShemaleZ

chastity, brunette
06:27

Chastity Sissy Raine Playing With Huge Dildo

5 months ago

Upornia

huge dildo, dildo, chastity
03:25

Trans Beauty In Chastity Fucked Missionary

1 year ago

ShemaleZ

fetish, missionary, chastity
08:00

Locktober Chastity Suck Slut for Dommes Bambi Bliss and Brittany Andrews

2 years ago

TXXX

chastity
15:09

Pussy-smothering and cock and ball torture for spandex Chastity Sissy

2 years ago

ShemaleTaxi

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40:21

Handjob Two Asian Guys Fucking A Ladyboy In Chastity In The Ass

11 months ago

BeMyHole

chastity
09:50

Trans Anal Fisting And Prolapse In Chastity

1 year ago

ShemaleZ

fetish, fisting, BDSM, chastity
18:10

Trans Sissy Scarlet Sky Sissygasms All Over Herself in Chastity and Bondage!

1 year ago

PornHub

anal, orgasm, bondage, blonde, goth, chastity
12:53

[SISSY] Libido processing failed. Did not finish off.

2 years ago

TrannyGem

chastity
09:38

Beautiful Sissy in chastity enjoys being fucked

4 years ago

xHamster

beauty, chastity
14:50

Real sissy slut anal in chastity cage

9 years ago

xHamster

latex, slut, sissy, chastity
21:51

Submissive Sissy Chastity Buttplug Play

5 years ago

ShemaleZ

BDSM, ass, toys, chastity
06:00

Sissy fucked hard while in chastity

1 month ago

xHamster

shemale, chastity, sissy, stockings, BBC
43:34 76%

ABS024 hottie femboy Abby Kitty wearing cheongsam in chastity - web cam female

1 year ago

ShemaleTaxi

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06:10

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3 years ago

ShemaleTaxi

bondage, chastity
13:35

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6 years ago

ShemaleZ

latex, sissy, chastity
08:27

Chastity Slave Loves To Spread

1 year ago

ShemaleZ

chastity
05:03

Trans Woman In Chastity Gives Blowjob

1 year ago

Upornia

chastity
04:28

Femboy Purity Victim Banged by Banging Machine

4 months ago

TrannyGem

machine, BBC, chastity
17:06

Cutie assistant public remote manage

2 years ago

TrannyGem

public, secretary, vibrator, chastity
12:57

Chastity small cock

3 years ago

XXXDan

small cock, chastity
16:07

Mike Ass Fucks Sissy Charlotte While She is Locked in EStim Chastity Cage

1 year ago

xHamster

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05:13

Cute & Sweet Girlfriend Turned Boyfriend Into Her Pegging Slut In Chastity. 5 Min

9 months ago

ShemaleZ

cute, BDSM, pegging, chastity
10:11

Tgirl In Chastity Teasing

4 months ago

AShemaleTube

homemade, webcam, chastity
06:17

Femboy Booty Spread by Monster BIG BLACK COCK Fake Penis

2 months ago

TrannyGem

BBC, chastity, machine
07:59

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

5 months ago

GetTranny

cum in mouth, chastity
09:39

Day 12 Of 26 In Chastity And Denial. Vibrating My Cage And Plug For Teasing

1 year ago

HClips

stockings, latex, chastity
18:49

Latex Transgirl In Chastity Spanked, Teased, And Fucked By Femdom

11 months ago

BeMyHole

femdom, latex, spanking, chastity
02:36

Sissy Sammi shown!!

2 years ago

xHamster

dildo, chastity
15:29 98%

Shemale Suzie XXL and Girl fuck and pegging a black slave in chastity cage

3 months ago

KeekAss

black, latex, threesome, fetish, domination, pegging, small tits
27:17 82%

NATALIE MARS PONY HAVE FUN

5 years ago

TrannyGem

huge dildo, heels, chastity, dildo
06:26

Walking in chastity cage and buttplug

9 years ago

xHamster

chastity
09:53

Hot TS Bailey Wilde Removes Chastity Then Jerks Off

4 months ago

xHamster

BDSM, big cock, chastity, femboy
01:10

Masturbation in chastity belt

10 years ago

xHamster

chastity
12:47

Sissy Andrea in chastity ass-fuck exercise

1 year ago

ShemaleTaxi

chastity
28:47 62%

Lizzy Yum August 2022 #1 Chastity Vagina Tits prisoner of love and chore

1 year ago

xHamster

bondage, chastity, post op
09:56

Sissy brianna slaton dirty little cock whore

3 years ago

BeMyHole

whore, slut, sissy, chastity
04:28

Chastity teen sissy maid fucked by old daddyp

3 years ago

BeMyHole

maid, sissy, chastity
04:05

Cynthia crossdresser gets fucked in chastity

4 years ago

AShemaleTube

chastity
07:41

One of the best superslut in chastity blow a weenie in public

4 years ago

ShemaleMovie

public, chastity
10:18

Chastity Sissy Anal Orgasms And Licking Cum Of Feet Jessica Bloom And Femdom Polieana

4 months ago

TXXX

feet, femdom, POV, anal, orgasm, chastity
11:42

Asslick Natalie Mars And Goth Charlotte Anal Play

11 months ago

BeMyHole

fisting, goth, chastity
24:46

Blonde sissy in chastity loves her bbc dildo on webcam

6 years ago

TXXX

dildo, BBC, chastity, solo
13:34 82%

Deep Throatfuck + Bareback Doggy Assfuck Cumshot Breeding By Shemale In Twink Ass (sub In Chastity)

2 years ago

TXXX

shemale, dogging, chastity
12:42

Sexy Trans Girl Sophie Struggles Helplessly in Bondage and Chastity

5 years ago

TrannyGem

bondage, BDSM, chastity
02:28

Tgirl in Chastity Fucked Doggystyle

1 year ago

xHamster

BDSM, dogging, chastity
02:31

Mistress in chastity fuck sissy strapon cum and incontinence

4 years ago

xHamster

femdom, strapon, chastity
03:20

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

5 years ago

AShemaleTube

strapon, ass to mouth, chastity
04:55

Fuck Machine And Double Electric Chastity

1 year ago

BeMyHole

latex, gloves, machine, double penetration, chastity
06:12

Assfuck Sissy Sleepover With Trans Ria Bentley & Lola Crystals

6 months ago

TrannyGem

shemale, lesbian, dirty talk, sissy, chastity, femboy
20:49

Spandex Sissy Punished by V-Card Fuckmachine Smacking Dickblowing Pegging by Domina Mercer

2 years ago

TrannyGem

femdom, latex, strapon, bisexual, train, bondage, spandex
04:40

Sissy Allison Edged Locked Pleasure Button with Wand

2 months ago

TrannyGem

bondage, crossdresser, masturbation, chastity
07:14

Sissy Marissa cheering for cock

2 months ago

xHamster

bondage, crossdresser, sissy, chastity, dildo
13:33

Sissy in Chastity putting on a show

4 years ago

ShemaleZ

chastity
23:34

Ghotic trap solo in chastity

2 years ago

ShemaleTaxi

tease, chastity
32:07

Chatty crossdresser tries out new depth - 2023-02-23 - part 2 - uncharted territory

1 year ago

xHamster

french, chastity
15:06 56%

Sissy Emily Hardon Cheerleader chastity fake penis play

2 years ago

ShemaleTaxi

dildo, cheerleader, penis, taxi, chastity, femboy
06:12

Daddy fucks sissy in chastity

5 years ago

xHamster

mature, mature anal, chastity
07:44

Trans in chastity cums from fucking machine

10 months ago

xHamster

chastity
05:22

Gorgeous Shemale Feminized in Chastity

2 years ago

xHamster

chastity
25:00

Sissy in chastity caged fuck dildo

3 years ago

AShemaleTube

chastity
20:08

Sissy Maid Self Bondage in Spiked Chastity Cage

1 year ago

xHamster

latex, bondage, maid, chastity
03:16 57%

Sissy pisses in urethral chastity cage in slow motion

2 years ago

xHamster

pissing, chastity
08:59

Crossdresser training to sissygasam in chastity cage

1 month ago

PornHub

anal, crossdresser, chastity, fetish
06:18

Natalie Stone - Locked in Chastity

5 months ago

IcePorn

teen (18+), masturbation, chastity
06:51

She-male chastity belted

3 years ago

ShemaleTaxi

chastity
29:26

Solo Fun On A Fuck Machine

1 year ago

BeMyHole

feet, glasses, shaving, toys, machine, small tits, chastity
05:34

Slutty Sissy Pirate Cage Dance by Sissy Mindy

2 months ago

xHamster

solo, crossdresser, chastity, sissy
08:29

Waking up with Transgender girl stacie in chastity

5 years ago

ShemaleZ

BDSM, chastity
06:34

Super-cute sissy pingveru jacks, chastity, forbidden to jizz

3 years ago

HDSex

sissy, chastity
05:07

Lianna Lawson In Shemale Slave In Chastity Butt Sex Fingered

6 months ago

ShemaleZ

BDSM, chastity
07:40

Trans goth bbgirl adaklein wants your cum so bad

2 weeks ago

xHamster

femboy, big cock, BBC, chastity, sissy, masturbation, goth
06:22

A chastity contraption will keep you in your place

1 month ago

ShemaleTaxi

chastity
30:55

Guy in a chastity gets pounded by an amazing tranny

6 years ago

TrannyOne

chastity
25:27

Sexy Chastity

6 years ago

TXXX

chastity
10:15

Skinny Tranny With Sexy Legs

3 months ago

TrannyGem

homemade, solo, sissy, chastity
03:40

Wide Open myself and nutting mitts free-for-all

5 months ago

TrannyGem

russian, vibrator, hands free, chastity
40:38

Chastity Cage On Her Penis Asian Ladyboy Threesome Fuck

2 years ago

ShemaleZ

penis, chastity
03:00

Wikky: chastity cage, cum in the opening

1 year ago

XXXDan

creampie, thai, facial, gape, hardcore, chastity
02:00

Sissy Wifey Competition Trailer

2 years ago

TrannyGem

femdom, wife, chastity
11:47

2 sissy latex nurses getting pegged in Chastity by MILF Lisa

4 months ago

xHamster

latex, shemale, nurse, shemale and girl, pegging, sissy, chastity
03:04

BBC Fuck Sissy in chastity

1 year ago

xHamster

latex, chastity
09:12

Fucking Myself With A 10 Inch Cock While Locked In Chastity

1 year ago

ShemaleZ

chastity
29:22

Imagining Im a Femboy make me Spreading Anal Invasion again

1 month ago

TrannyGem

cute, teen anal (18+), 18, masturbation, toys, chastity
08:41 54%

Crossdresser Compilation Beautiful Ladyboy Fucked Sissy Chastity Fucked Femdom

2 years ago

ShemaleZ

femdom, fisting, BDSM, crossdresser, chastity
12:28

Slutty Trans Bunny Lilith Eclipse Fucks Herself With Carrots In Chastity bum To facehole

1 year ago

ShemaleTaxi

ass to mouth, gape, cosplay, chastity, femboy
25:44

Cute trap The Mortal Medusa in chastity

4 years ago

ShemaleZ

cute, chastity
27:23

Sissy Training: Deepthroat, anal & Sissygasm while locked in Chastity

1 year ago

PornHub

stockings, black, train, fetish, dildo, panties, dress
04:58

My sixth day in chastity

6 years ago

TXXX

chastity
02:17

Chastity Latex

4 years ago

AShemaleTube

latex, vintage, chastity
1:08:51

Sissy slut in lingerie anal fuck on sex machine with squirting in chastity cage! Good little femboy beta cuck slave!

8 months ago

xHamster

pissing, squirt, crossdresser, chastity
03:07

Working Her Way Up To The

1 month ago

TrannyGem

femdom, fetish, bondage, dildo, BDSM, toys, sissy
17:28

Sexy TS Lucia Maya in Chastity fucks her ass & LEAKS CUM before BLOWING HER LOAD

7 months ago

xHamster

cumshot, hands free, chastity, cum in ass
06:14

Sissy cums in chastity by domina using her vibrator

1 year ago

ShemaleTaxi

femdom, vibrator, taxi, chastity
06:18

Assistant Abby Kitty,pantyhose, high high-heeled slippers ,getting off ,popshot

2 years ago

TrannyGem

pantyhose, sperm, chinese, heels, secretary, flexible, chastity
02:40

Cum in my Chastity

2 years ago

xHamster

german, chastity
2:14:04

Delicious Cheeks Plays Deltarune (part two) [with Mutt Faux-Cock!]

3 years ago

TrannyGem

game, chastity
05:01

Sissy In Chastity Fucks Herself Dumb

2 years ago

ShemaleZ

chastity
10:23

Beautiful Transgender Caged Sissygasms & Anal Stretching - Big Dildo Prostate Orgasms Jessica Bloom

2 years ago

PornHub

prostate, orgasm, gape, chastity
05:52

Hot Sissy Anal Slide In Chastity Cage

1 year ago

HClips

chastity
01:02

Chastity Tales

3 years ago

xHamster

chastity
06:16

Lily Leigh Cam Show - November 24th 2023 (part 2) - Chastity Cage Dildo & Masturbation Private Show

3 months ago

ShemaleZ

dildo, masturbation, chastity
03:36

Plugged Sissy Milk In Chastity Cage Over A Mirror

1 year ago

Upornia

milk, chastity
09:51

CROSSDRESSER IN stocking AND HIGH heels IN A PINK CHASTITY BELT WATCHING A PORN video

8 months ago

ShemaleMovie

pantyhose, heels, chastity
10:34

Sissy in White Stocking and Play with Dildo and Cum

2 years ago

PornHub

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