SHEMALE • CHASTITY 4,348 videos

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34:17 40%

New Years Bang: Chelsea Marie Frees Butt Slut From Chastity

4 years ago

TrannyOne

slut, chastity
1:08:53 40%

Sissy slut in lingerie ass-tear up fuck on sex machine with squirting in chastity cage! Good little femboy beta cuck gimp!

4 months ago

ShemaleMovie

pissing, squirt, lingerie, crossdresser, ass, toys, machine
10:38 40%

Prelude to Be a chick for Me - Nicci FEMINIZES and locks Jordyn in chastity

7 months ago

ShemaleMovie

strapon, sissy, chastity, crossdresser, behind the scenes
06:00 40%

Femdom Double Anal Pegging for Chastity Sissy Lucy

3 years ago

xHamster

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06:05 40%

Cd Caged By Femdom Girlfriend Slave Cums In Chastity Ru

4 years ago

ShemaleZ

femdom, girlfriend, chastity
15:37 40%

HYPNOTIZED - Subjugated With V-Card Box Erica Virgin Makes Female Domination Queenie Sateen SPRAY A BUNCH

1 year ago

TrannyGem

blowjob, chastity, shemale and girl, big cock, lingerie, squirt
11:35 40%

Trans XXXSamanthaPhD 11 Chasity After Jizz Ass-Fuck

1 year ago

TrannyGem

pissing, chastity, sissy
14:55 40%

Lanas Weekly Ass-Fuck Lesson

4 years ago

TrannyGem

femdom, russian, fisting, chastity
15:14 40%

Dominatrix deprives femboy of ass-fuck chastity

11 months ago

ShemaleMovie

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01:54 40%

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2 years ago

xHamster

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11:24 40%

Real sissy in chastity outdoor

7 years ago

ShemaleZ

latex, outdoor, sissy, chastity
27:08 40%

Trans Anal Of Chastity Sandy

12 years ago

AShemaleTube

chastity
14:18 40%

Sissy Virginity (part two)

3 months ago

TrannyGem

BDSM, crossdresser, cosplay, chastity
08:03 40%

Vikki Deep in virginity tweak and uber-cute sundress and high-heeled slippers vs bang machine

8 months ago

TrannyGem

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03:08 40%

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4 years ago

TrannyGem

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04:25 38%

Forearms-Free-For-All Sissygasms, Sounding, & Railing Fake Penis - A Sissy Compilation

4 years ago

TrannyGem

femdom, train, bondage, penis, cumshot compilation, slut, chastity
25:10 38%

Black Tranny spunk insert - episode 1

1 year ago

ShemaleMovie

ladyboy, shemale, big cock, chastity, black, blowjob
28:13 38%

Uncovered CD Sissy Katie Does Live Showcase In Purity Cell

8 months ago

TrannyGem

small cock, blowjob, train, bondage, solo, 18, babe
1:08:50 38%

Real fledgling homemade sissy cuck penetrates hump machine in chastity cage, feminization squirting femboy!

2 years ago

ShemaleTaxi

squirt, crossdresser, chastity, femboy, homemade, machine
09:37 38%

Sissy In Chastity Public Walk Showing Her Ass And Then She Is Fucked Bareback In Many Positions

3 years ago

Upornia

public, sissy, chastity
22:30 33%

Mistress Mercer gives her sissy chastity slave a disciplinary tease and CBT session

1 month ago

XXXVogue

domination, shemale, BDSM, sissy, chastity
07:09 33%

SIssy Bimbo Slut BBC

2 years ago

xHamster

smoking, BBC, chastity
04:17 33%

Trans mommy with big tits, in chastity, taking a huge dildo

2 years ago

AShemaleTube

mom, homemade, huge dildo, crossdresser, toys, chastity
05:50 33%

Sissy Slut Milked In Chastity

2 years ago

GetTranny

chastity, small cock, milk, sissy
03:21 33%

Dominatrix encouraged her sissy pig to cock and ball torture emasculation dog collar its nut sack angel Scarlett black

1 year ago

TrannyGem

dogging, crossdresser, chastity, bondage
11:41 33%

Phat boner TGirl barback anal invasion fucks mature guy in chastity

1 year ago

VideoSection

mature, stockings, blowjob, mature anal, british, big cock, chastity
1:08:02 33%

Chastity Transfiguration

2 years ago

XXXDan

femdom, lesbian, masturbation, chastity
03:12 33%

Sissy Bitch Chastity Caged ruined orgasm

4 years ago

TrannyOne

orgasm, swallow, chastity, crossdresser
14:51 33%

Its time you lost your shemale chastity

6 years ago

HDSex

chastity
08:45 33%

Ultra-Cute Encaged Boi Becomes An Rectal Superslut

1 year ago

TrannyGem

sissy, amateur, chastity, solo, cute
04:26 33%

Unmasking - Miss Eva Mae - Girl Masker & Living Female

1 year ago

TrannyGem

shemale, crossdresser, chastity, rubber
11:06 33%

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2 years ago

TrannyGem

japanese, chinese, chastity, reality
05:19 30%

Palms Free-For-All Buttfuck Climax Sissygasm Compilation six

2 years ago

TrannyGem

prostate, cumshot compilation, orgasm compilation, anal orgasm, hands free, chastity
06:15 30%

Féminisation et Pegging de mon esclave chaste : Teaser Live Web Cam Replay : Maîtresse Julia

1 year ago

TrannyGem

pantyhose, femdom, strapon, anal, fetish, fisting, boots
19:15 30%

Sissy punished and fucked for removeing her chastity part 3 final

6 years ago

ShemaleZ

fetish, interracial, sissy, chastity, bareback
16:48 29%

Sissification lecture Encaged Sissy V-Card Belts, Masturbate, Sissygasm by Domina Veronica Taboo

4 years ago

TrannyGem

femdom, train, instruction, tease, crossdresser, JOI, sissy
01:02 29%

Sissy Maid Gets Locked in Bondage and Chastity to Be Fucked by Her Sex Doll

2 months ago

TrannyOne

shemale, sissy, amateur, maid, chastity, bondage
08:45 29%

Sissy Horse Bride rails her fake penis stand in innocence

10 months ago

TrannyGem

bride, train, huge dildo, fetish, bondage, dildo, BDSM
19:06 29%

Sissy in chastity swallow cum

10 years ago

xHamster

latex, swallow, sissy, chastity
10:45 29%

Sissy Maid Krissy Small Penis Humiliation - female voice over SPH with chastity feminization

1 year ago

AShemaleTube

stockings, fetish, maid, crossdresser, sissy, chastity
06:25 29%

Gina in chastity, pleased and spanked

5 years ago

xHamster

mature anal, spanking, chastity
12:31 29%

Sissy Slut Whore

1 year ago

xHamster

small cock, shemale, dildo, solo, latina, crossdresser, whore
08:00 25%

SISSY In the park in the daytime, 2 senior dudes munched my puffies while frolicking with my wood.

7 months ago

TrannyGem

amateur, public, outdoor, crossdresser, piercing, gangbang, chastity
25:00 25%

Black Tranny Jizz Jam - Episode 1

1 year ago

xHamster

black, big cock, shemale, chastity
04:47 22%

Chastity sissy future

6 years ago

AShemaleTube

sissy, chastity
14:49 20%

WHAT FINER STOCKING TO WEAR ON A SISSY BLACK FUCK-STICK RENDEZVOUS

4 years ago

TrannyGem

femdom, teacher
11:22 20%

Thick chubby Femboy needs a BBC

1 year ago

xHamster

femboy, BBC, sissy, chubby, big ass
06:10 20%

Chastity Slut In Stockings And Heels Playing

2 months ago

Fuxxx

mature, BDSM, chastity, shemale
11:59 20%

Sissy femboy Paddedbunny strips out of a wet diaper and stains his cute undies while in a chastity cage

1 month ago

XXXVogue

pissing, cute, small cock, shemale, orgasm, crossdresser, strip
08:14 20%

Chastity in Chastity Day six prize

11 months ago

HDSex

handjob, dildo, crossdresser, bareback, BBC, sissy, chastity
14:44 20%

Alpha male romping sissy bareback, cums inwards and she embarks masturbating like a girl in chastity

5 months ago

ShemaleMovie

shemale, sissy, crossdresser, chastity
02:10 20%

Chastity Orgasm - PMV By HoloPMV

1 year ago

AShemaleTube

shemale, orgasm, crossdresser, cumshot, sissy, chastity
32:11 20%

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

3 years ago

xHamster

mature, mature anal, BDSM, erotic, machine, chastity
26:00 20%

Selfbondage latex - Chastity, nose mask p2

3 years ago

xHamster

latex, french, heels, mask, chastity
27:01 17%

HUMUNGOUS GAPES, Rosebutt, tummy swelling, AMPLE sugary-sweet gape farts, Twunk Jules Verne Assfuck FUCK HOLE DESTRUCTION

3 years ago

TrannyGem

farting, train, huge dildo, fetish, gape, chastity
07:24 17%

KNOTTING my bad dragon taking a tall guy can and a champagne bottle all the way in my caboose DEEP

1 year ago

TrannyGem

huge dildo, tall, dildo, insertion, sissy, gape, chastity
17:10 17%

Man Masturbates Off with Trans Lady in Purity

7 months ago

TrannyGem

handjob, bondage, BDSM, crossdresser, babe, chastity, femboy
06:53 17%

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

1 year ago

xHamster

crossdresser, JOI, pantyhose, mom, chastity
02:44 14%

My Beau Wants To Sundress Like A Tramp

10 months ago

TrannyGem

amateur, femdom, latex, shemale, fetish, boots, crossdresser
06:29 14%

Such a Happy SpitRoasted Sissy Slut, Her Holes So Full

9 months ago

xHamster

deepthroat, amateur, chastity, sissy, femboy, shemale
08:16 14%

Bailey Wilde And Cassidy Cream In Dominatrix Fucks Hot Crossdresser In Chastity 9 Min

8 months ago

HClips

amateur, crossdresser, stockings, shemale, chastity, MILF
21:51 14%

Submissive Sissy Chastity Buttplug Play

6 years ago

ShemaleZ

BDSM, ass, toys, chastity, crossdresser
10:32 14%

Fetish femdom lesbian sex in office with busty blonde lesbian boss

1 year ago

xTits

femdom, blowjob, lesbian, fetish, big tits, office, natural
08:05 14%

Sissy Gets a Massive Fountain 1

5 years ago

TrannyGem

bondage, slut, chastity, cum in ass
12:26 13%

Chastity box Sissy dick milking with cum countdown

8 months ago

ShemaleMovie

train, BDSM, milk, nylon, toys, chastity, femboy
28:30 10%

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

1 year ago

TrannyGem

mom, femdom, prostate, dildo, 18, cartoon, chastity
06:23

Sissy Blaire_18 locked in a chastity belt while dominatrix Nika teases his pouch with a wand

1 month ago

XXXVogue

BDSM, chastity
24:46

Chastity Sissy Gets tights Torn and Pegged by Bad Dragon Strapon by mistress Mercer

1 week ago

ShemaleMovie

femdom, strapon, BDSM, spanking, toys, tight, pegging
05:57

Daddy Loves To Wreck My Asshole In Chastity

3 days ago

BeMyHole

femboy, amateur, interracial, BBC, creampie, domination, shemale
27:22

Sweet Chastity 16

3 days ago

AShemaleTube

shemale, chastity
08:01

Sissy Bitch Uses Cum as Lube and has Anal Sissygasms in Chastity Jessica Bloom

1 month ago

TrannyOne

anal, sissy, chastity, shemale
08:07

Lingerie Sissy Gets Locked Onto Her Dildo Pole and Tries to Cum in Chastity

Yesterday

AShemaleTube

dildo, sissy, shemale, solo, chastity, small cock
05:08

TS Chelsea Marie Pegging And Long Term Chastity Release Foot Worship And Extreme Anal Poundi

6 days ago

AShemaleTube

big cock, pegging, shemale fucks guy, chastity, feet, shemale
05:12

Stoner Girl

1 month ago

TrannyGem

smoking, train, anal, fetish, blonde, babe, toys
10:41

Losing Her chastity in a twat -Cliff Media

3 months ago

ShemaleTaxi

chastity, strapon, czech, gloryhole
12:29

Sweet Chastity 17

3 days ago

AShemaleTube

shemale
09:03

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

1 month ago

XXXVogue

stockings, chastity, goth, latex, dildo
05:10

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

1 month ago

AShemaleTube

feet, chastity, femdom
10:24

Ella Mox, the trans doll in chastity, gets wrecked by a machine and shows off that gaped hole

1 month ago

XXXVogue

lingerie, pantyhose, anal, chastity, nylon
02:20

Trans Nymph Porked in Virginity

1 month ago

TrannyGem

ass, crossdresser, bondage, fetish, BDSM
10:19

Very Hot Blonde Crossdresser In Chastity Fucked

3 weeks ago

HClips

chastity, crossdresser, amateur, shemale, stockings
29:51

30 mins no break fellate spitroast contest!

2 months ago

TrannyGem

stockings, double anal, crossdresser, contest, gangbang, deepthroat, heels
28:01

POV Trans Femdom, Suck My Dick While in Chastity You Sissy Slut!

4 days ago

$$ FapHouse

cum in mouth, sissy, chastity, cumshot, femdom, cuckold, POV
08:00

Chastity Ts Vs Bbc 3

3 months ago

PePorn

BBC, chastity, interracial, threesome
22:13

Sweet Chastity 14

1 week ago

AShemaleTube

chastity
07:48

TRANSSEXUAL Willow Hammerz - Snowbunny Sissy BNWO PMV

2 months ago

TrannyGem

amateur, interracial, cuckold, compilation, cumshot compilation, BBC, sissy
10:00

Extraordinary Natural Tits Tgirl with a chastity cage Chapter 2

1 month ago

AShemaleTube

small tits, solo, chastity, webcam
03:39

Trans Goddess Pummeling Machine

1 month ago

TrannyGem

fetish, dildo, sissy, cosplay, chastity
10:00

Extraordinary Natural Tits Tgirl with a chastity cage Chapter 3

2 weeks ago

AShemaleTube

femboy, chastity, solo, natural
03:19

Trans Sow Loren Aprile Rectal Abasement

1 month ago

TrannyGem

feet, femdom, shemale, french, strapon, smoking, anal
12:48

Sweet Chastity 13

1 week ago

AShemaleTube

chastity, shemale
14:05

Young Shemale In Chastity And Latex Gets Fucked By Older Guy

3 weeks ago

ShemaleZ

amateur, latex, stockings, chastity
15:40

Riding big fat dildos in chastity!

1 month ago

NuVid

shemale, dildo, solo, chastity, fat
07:50

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

2 years ago

TrannyGem

interracial, BBC, chastity, shemale and girl
07:59

Nyxi Gets Anal From Tranny While Locked In Chastity

2 weeks ago

GetTranny

chastity, shemale, domination
03:15

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

3 weeks ago

$$ FapHouse

shemale, solo, chastity, outdoor, toys, sissy
05:20

Year-long chastity release with shemale Chelsea Marie, featuring foot worship, anal pegging, and face fucking

1 week ago

XXXVogue

blowjob, BDSM, chastity, domination, pegging
04:00

Jessy Jones In Shemale Ass Sex Fucks Sub In Chastity

1 week ago

Fuxxx

BDSM, chastity, stockings
04:22

Encaged nice trans dame gets bred by a knotty plaything - POVish

1 month ago

TrannyGem

shemale, amateur, cumshot, femboy, chastity
05:09

TS Sub Suspended Hogtied and Fucked

3 days ago

TrannyGem

domination, chastity, bondage, ladyboy, BDSM
05:03

Spandex Female Dom Lora Cross uses purity slave for sounding unleash

1 month ago

TrannyGem

bondage, BDSM, sissy, chastity, latex, femdom
48:11

Sweet Chastity 8

1 week ago

AShemaleTube

chastity, shemale
10:15

Sweet Chastity 9

1 week ago

AShemaleTube

chastity
10:26

Alternative girls Miss Flora, Anuskatzz, and Maz Morbid dominate punk guy with latex, anal fisting, and chastity

Yesterday

XXXVogue

BDSM, chastity, goth, latex, fisting, shemale and girl
04:57

Sissys in Chastity (PMV)

5 years ago

BeMyHole

chastity
11:07

Sissy Lucy Loced down in iron chastity and chains

1 month ago

ShemaleTaxi

latex, shemale, bondage, BDSM, crossdresser, taxi, sissy
05:55

Tied up sissy in chastity cage with anal invasion buttplug prepared for fuck

3 months ago

ShemaleMovie

shemale, bondage, BDSM, crossdresser, tied, prostitute, ass
02:29

Sissygasm in v-card

1 month ago

TrannyGem

shemale, chastity, hands free
07:49

Ultra-Cute Sissys Gams Commence Shuddering As Humungous Beefstick Packs Her Cootchie While Her Lil Clitty Is In Virginity

4 years ago

TrannyGem

femdom, bondage, BDSM, chastity, crossdresser
07:59

Bbc Vs Sissy In Chastity 2

2 months ago

xShemaleTube

sissy, BDSM, BBC, chastity, shemale
11:45

Sissygasm - Buttfuck with horse corset

2 months ago

TrannyGem

anal, chastity, sissy, leather
06:20

Futa smashes femboy in v-card and spunk in his backside and on his back (3 DIMENSIONAL toon)

2 months ago

TrannyGem

shemale and girl, goth, cartoon, sissy, chastity
11:27

Chubby Trans Girl Vibin

3 years ago

BeMyHole

fetish, chubby, BBW, ass, mask, toys, chastity
10:00

Extraordinary Natural Tits Tgirl with a chastity cage Chapter 4

6 days ago

AShemaleTube

solo, chastity, shemale
08:00

Chastity Ts Vs Bbc 3

2 months ago

xShemaleTube

chastity, BBC, interracial, threesome, BDSM, shemale
07:06

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

2 months ago

ShemaleTaxi

casting, maid, dildo, audition, toys, machine, sissy
05:41

HOTTEST Crossdresser Bailey Wilde in chastity nailed switch sides Cowgirl

2 months ago

ShemaleTaxi

sissy, crossdresser, chastity
05:47

Anal Slut Jessica Bloom Rides 11 Inch Qutoys Didlo Balls Deep - Chastity Sissygasm Cumswallow

11 months ago

xHamster

shemale, chastity, riding, anal, dildo
01:17

BBC on Fuckmachine Fuck Sissy in chastity cage

2 years ago

xHamster

latex, sissy, chastity
06:21

Gina in chastity, pleased and spanked

5 years ago

ShemaleZ

BDSM, spanking, chastity

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