SHEMALE • CHASTITY 4,282 videos

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04:28 75%

Taking It On All 4S Gets Her Every Time

1 year ago

TrannyGem

orgasm, chastity, machine
03:11 75%

ABT250502 Sexy devil in chastity -穿贞操锁的性感小魅魔

7 months ago

AShemaleTube

chastity, asian, chinese, shemale, pantyhose, femboy
13:01 75%

Female Dominance hand-job for my sissy crossdresser

3 years ago

TrannyGem

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13:00 75%

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3 years ago

xHamster

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06:12 75%

The Start of Perminant Chastity

6 years ago

ShemaleZ

fetish, BDSM, chastity
15:37 75%

TRANSFIXED - Submissive With Chastity Cage Erica Cherry Makes Femdom Queenie Sateen SQUIRT A

1 year ago

AShemaleTube

shemale, chastity, femdom, squirt
01:54 75%

Daddy made me a new milking toy on my chastity

3 years ago

xHamster

milk, 18, chastity
06:38 75%

Sissy Lucy Gets Spanked In Chastity 7 Min

4 years ago

HClips

spanking, chastity
05:24 75%

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

1 year ago

TrannyGem

cute, creampie, huge dildo, orgasm, ass, heels, machine
1:13:30 74%

Best of Sissies Cumming in Chastity

4 years ago

BeMyHole

cumshot compilation, sissy, chastity, compilation, crossdresser, amateur
02:12 74%

Fuck Stick

1 year ago

TrannyGem

amateur, french, small tits, sissy, chastity
32:59 73%

Virginity Fuckdolls reverse Gangbang Kaela Luna Thea Daze Luci Belle Meddle blooms Chastity

3 months ago

ShemaleTaxi

chastity, shemale, orgy, group, gangbang
08:00 73%

Sissygasm In Chastity For A Fucked Crossdressed Slave. Spanking Session With Mistress

3 years ago

GetTranny

femdom, bondage, chastity, crossdresser
10:33 73%

Chastity Sissy Anal orgasms And munching jism of Feet Jessica Bloom and Femdom Polieana

1 year ago

VideoSection

feet, femdom, huge dildo, orgasm, maid, dildo, sissy
08:14 72%

Chastity Cage On Her Penisthai Ladyboy Threesome Fucked

4 years ago

TXXX

chastity, asian, fetish
07:59 72%

BBC Putted A Chastity Cage In Her Trans Wife And Fucker Her Until Gives Her A Big Facial

2 years ago

BeMyHole

black, interracial, wife, BBC, chastity, big ass
1:03:39 71%

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 1

2 years ago

xHamster

stockings, french, lingerie, chastity, sissy, anal
09:50 71%

Hot Blonde Bailey Wilde Removes Chastity Then Masturbates

1 year ago

xHamster

BDSM, crossdresser, chastity
02:15 71%

Tied to the BIG BLACK COCK breeding simulator [recommended training]

3 months ago

TrannyGem

train, prostate, teen anal (18+), orgasm, bondage, 18, tied
05:50 71%

Marvelous sissy fisted while gliding a sounding rod deep in her chastity locked clit until splooging everywhere

11 months ago

VideoSection

pissing, fisting, boots, ladyboy, clit, goth, toys
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
06:27 71%

Chastity Sissy Raine Playing With Huge Dildo

2 years ago

Upornia

huge dildo, dildo, chastity
01:10 70%

Masturbation in chastity belt

11 years ago

xHamster

chastity
13:29 70%

Day six in v-card: Unboxing brand fresh iron purity cell by myinside.es and edging me with wand

3 years ago

TrannyGem

femdom, tease, bondage, clit, chastity, sissy
04:09 69%

Chastity slave sissy wife tormented by Mistress

6 years ago

ShemaleZ

femdom, wife, BDSM, chastity
15:50 68%

Sissy at Gloryhole Gets Asshole Licked by Stranger

1 month ago

TrannyGem

cute, fetish, gloryhole, crossdresser, asshole, sissy, stranger
15:03 67%

Chastity Tgirl Gets Double Anal Fucked In A With Itzel Saenz And Hardcore Gangbang

2 years ago

ShemaleZ

beauty, POV, double anal, gangbang, toys, double penetration, hardcore
06:03 67%

Nice Sissy Sidney in v-card does how she is told

4 years ago

TrannyGem

sissy, chastity, domination
03:16 67%

Sissy teaching with and sans virginity

3 years ago

TrannyGem

train, cartoon, hands free, chastity
09:34 67%

Being put into a plane box After Misstress cleans my locked Clitty Little cock

2 years ago

TrannyGem

femdom, skirt, chastity
27:24 67%

Trans girl in chastity fucked amateur

3 years ago

DrTuber

shemale and girl, chastity
05:50 67%

Chastity Sissy Cumslut Trains Her Asshole And Swallows Her Own Cum, Multiple Prostate Orgasms

11 months ago

xHamster

train, prostate, orgasm, fisting, dildo, british, swallow
03:03 67%

Abby Kitty And Sissy Slave In Ab085 Lustful Be Masters Chastity (chinese And English Subtitles)

2 years ago

Upornia

teen (18+), chinese, sissy, chastity, asian, solo
03:25 67%

Trans Beauty In Chastity Fucked Missionary

2 years ago

ShemaleZ

fetish, missionary, chastity
03:16 67%

Sissy pisses in urethral chastity cage in slow motion

3 years ago

xHamster

pissing, chastity
10:50 67%

Locked sissy assfuck fuck stick self feetjob and self spunk slurping

1 year ago

TrannyGem

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12:34 67%

A nasty getting off sessiom

1 year ago

TrannyGem

amateur, cute, anal, squirt, fetish, bondage, big tits
04:17 67%

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

2 years ago

xHamster

handjob, 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
10:03 67%

Sexy Blonde Crossdresser in Chastity Fucked

9 months ago

xHamster

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10:16 67%

Highly super-hot Blonde Crossdresser in Chastity boned

1 year ago

ShemaleTaxi

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07:41 67%

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

5 years ago

ShemaleMovie

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05:26 67%

ABH Sweet girl in chastity riding dildo and play vibrat

2 years ago

AShemaleTube

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10:00 67%

CD chastity fuck

5 years ago

xHamster

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05:32 67%

Latex Sissy In Chastity And Fucked By Mistress

3 years ago

ShemaleZ

femdom, latex, chastity
14:21 67%

New Boots and Armbinder - Sissy Maid Stuck in Bondage Again

1 year ago

xHamster

latex, bondage, boots, BDSM, chastity
02:34 66%

SISSIES IN CHASTITY

5 years ago

xHamster

amateur, sissy, chastity
08:24 65%

Sissy Gets a Thick Fountain two

4 years ago

TrannyGem

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12:23 64%

Chastity locked sissy squirting on a dildo while thinking about her daddy

1 year ago

xHamster

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11:47 64%

2 sissy latex nurses getting pegged in Chastity by MILF Lisa

1 year ago

xHamster

latex, nurse, shemale and girl, chastity
02:37 63%

Twerk Sissy Chastity - PMV By HoloPMV

2 years ago

AShemaleTube

sissy, chastity
08:41 63%

Crossdresser Compilation Beautiful Ladyboy Fucked Sissy Chastity Fucked Femdom

4 years ago

ShemaleZ

femdom, fisting, BDSM, crossdresser, chastity, compilation
05:15 60%

Chastity & Ass to mouth with BIG black cock

3 years ago

xHamster

black, small cock, ass to mouth, BBC, chastity
05:59 60%

Long sissygasm compilation

1 year ago

TrannyGem

cumshot compilation, orgasm compilation, BBC, sissy, anal orgasm, hands free, chastity
06:10 60%

Chastity sub fucked hard by TS

3 months ago

AShemaleTube

shemale, chastity, ladyboy
14:31 60%

Ive Learned To Enjoy Not Cumming Sissy Femboy Chastity & Self Foot adore + cbt shemale Ball Slap

5 months ago

ShemaleMovie

feet, femboy, crossdresser, sissy, chastity, orgasm
05:18 60%

Trans innocence ejaculation

2 years ago

TrannyGem

bondage, leather, pegging, chastity
06:12 60%

Daddy fucks sissy in chastity

6 years ago

xHamster

mature, mature anal, chastity
21:45 60%

Flat Chastity Sissy

8 months ago

xHamster

squirt, dildo, sissy, chastity
05:54 60%

Multiorgasm sissy riding dildo

1 year ago

xHamster

chastity, sissy, crossdresser
05:12 60%

Sissy cum in inverted chastity cage after being denied for 60 days

2 years ago

xHamster

german, BBW, chastity
07:32 60%

FULL TIME CHASTITY

9 years ago

xHamster

latex, full movie, chastity
15:39 60%

Sissy playing with dildo until cumming

1 year ago

xHamster

dildo, solo, crossdresser, sissy, chastity, finnish
02:13 60%

Trans witch summons something she doesn't mind riding

2 years ago

xHamster

sissy, chastity, FTM, dutch
09:39 59%

Sissy Candy in black lingerie and chastity is locked and impaled on her dildo stand

1 year ago

xHamster

black, fetish, bondage, dildo, lingerie, crossdresser, sissy
28:47 59%

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

3 years ago

xHamster

bondage, chastity, post op, masturbation
14:37 58%

The church of Anime Porn

6 months ago

TrannyGem

anal, amateur, chastity, boots, anime, homemade
05:58 58%

Sissy Emily Hardon V-Card Fuck Stick Have Fun

5 years ago

TrannyGem

chastity, femboy
05:36 58%

Double Machine

3 years ago

xHamster

fetish, double anal, 18, machine, double penetration, chastity
11:24 57%

Real sissy in chastity outdoor

4 years ago

TrannyOne

sissy, chastity, outdoor
06:51 57%

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

2 years ago

xHamster

BBC, sissy, missionary, chastity
08:00 57%

Strapped To Fucking Machine Chair In Pvc Catsuit Gagged In Chastity

2 years ago

GetTranny

bondage, cosplay, chastity, latex
09:48 57%

Piss Compilation - Sissy, Chastity Belt, Locked, Public Pee 10 Min

2 years ago

ShemaleZ

pissing, public, chastity, sissy
05:49 57%

Trans Nun in Virginity Box Spunks From Anal Invasion Have Fun

2 years ago

TrannyGem

dildo, sissy, anal orgasm, hands free, chastity, prostate
07:04 56%

Get ready to fuck me and cum... I'll wait for you in chastity and with my ass open

2 years ago

xHamster

mature, mature anal, crossdresser, chastity, cum in ass, latina
10:21 56%

Sissy Gets Brainwashed By Bambi Hypnotizing Files PMV

1 year ago

TrannyGem

dildo, crossdresser, compilation, sissy, chastity, amateur
03:03 56%

MaureenNadh - (Day 1 Locked In Chastity) Anal Training Before School

2 years ago

xHamster

teen (18+), train, teen anal (18+), domination, chastity, solo
13:33 54%

Super Flat Chastity Sissy Anal Dildo Squirt

1 year ago

HClips

shemale, squirt, dildo, solo, sissy, chastity
06:32 53%

Fisting sissy in chastity cum hands free

6 years ago

ShemaleZ

train, fisting, lingerie, toys, hands free, chastity
18:35 53%

Sissy Maid Gets Dressed, Cuffed and Locked and Rides Her Doll

10 months ago

xHamster

mature, blowjob, maid, uniform, crossdresser, riding, dress
10:48 53%

Real sissy in in natures garb beach in chastity and rosebud

10 years ago

TXXX

beach, outdoor, natural, chastity
11:19 51%

Trangirl's in Virginity Swallow from her Love Glove in Public

3 months ago

TrannyGem

public, shemale, smoking, gloves, crossdresser, swallow, condom
09:02 51%

Sissy Submissive Bitch Gets Fucked Hard In A Chastity By Cruel Mistress And Her 13 Inch Bbc Strapon

5 months ago

HClips

amateur, femdom, shemale, strapon, POV, interracial, 18
12:33 50%

Kiss his jism out of my throat in front of your Ex CUCK CHASTITY

1 year ago

ShemaleTaxi

kissing, pantyhose, teen (18+), cuckold, goth, taxi, chastity
02:37 50%

AB093 Camera Operator feminized drizzling-pegging (Asian and English subtitles)

4 months ago

TrannyGem

pissing, handjob, feet, pantyhose, femdom, strapon, squirt
03:07 50%

Sissy games in innocence: Pegging and delight in a box Domina Julia female domination

10 months ago

TrannyGem

femdom, bisexual, threesome, crossdresser, domination, pegging, sissy
16:55 50%

Teen sissy in chastity with her Master

6 years ago

HClips

chastity
16:07 50%

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

3 years ago

xHamster

mature, mature anal, anal, couple, monster, small tits, sissy
03:58 50%

Big Ass Ts In Chastity Fucked Doggystyle

2 years ago

ShemaleZ

latex, chastity
11:58 50%

Sissy Bunny switches out of doused nappy, blows a load in pinkish underpants with innocence box

1 year ago

TrannyGem

pissing, pantyhose, diaper, vibrator, sissy, chastity
24:46 50%

Blonde sissy in chastity loves her bbc dildo on webcam

8 years ago

TXXX

dildo, BBC, chastity, solo, interracial, webcam
06:14 50%

Average manga porn paramour in virginity box

3 years ago

TrannyGem

feet, russian, cosplay, chastity, solo, femboy
17:13 48%

Sissy Dani Firm Buttfuck Teaching PT two (Moist Audio)

3 months ago

TrannyGem

teen (18+), crossdresser, british, 18, whore, slut, sissy
11:49 48%

Tricked into sissification tricked into chastity (New Vids on MANYVIDS)

6 years ago

HClips

latex, fetish, BDSM, chastity, POV
23:48 46%

Pink Mercy Trap in Chastity doing Deepthroath and Anal Play

6 years ago

TrannyGem

italian, dildo, erotic, cosplay, chastity, sensual
30:30 45%

Libération Après 1 Mois De Cage

2 weeks ago

BeMyHole

handjob, french, blowjob, threesome, BDSM, piercing, ass licking
10:15 45%

Jessica Bloom Riding Monster Dildos Multiple Anal Orgasms in Chastity

3 years ago

xHamster

orgasm, monster, anal orgasm, chastity
11:26 43%

Sissy Trans Girl In Chastity Gets Fucked Hard In Multiple Positions

2 years ago

ShemaleZ

sissy, 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!

3 months ago

ShemaleMovie

pissing, squirt, lingerie, crossdresser, ass, toys, machine
06:58 40%

Sissy attempt to jizz in micro v-card cell

3 years ago

TrannyGem

femdom, cuckold, panties, slut, 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
10:38 40%

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

6 months ago

ShemaleMovie

strapon, sissy, chastity, crossdresser, behind the scenes
01:54 40%

Pissing nacked outdoor in my tiny chastity

2 years ago

xHamster

pissing, outdoor, bondage, chastity
27:08 40%

Trans Anal Of Chastity Sandy

12 years ago

AShemaleTube

chastity
14:55 40%

Lanas Weekly Ass-Fuck Lesson

4 years ago

TrannyGem

femdom, russian, fisting, chastity
05:16 33%

I'm in real seam nylons and chastity cage on the road, I also pee myself vigorously in the cage

11 months ago

xHamster

pissing, stockings, fetish, outdoor, crossdresser, nylon, toys
08:45 33%

Ultra-Cute Encaged Boi Becomes An Rectal Superslut

1 year ago

TrannyGem

sissy, amateur, chastity, solo, cute
1:08:02 33%

Chastity Transfiguration

2 years ago

XXXDan

femdom, lesbian, masturbation, chastity
14:51 33%

Its time you lost your shemale chastity

6 years ago

HDSex

chastity
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
04:26 33%

Unmasking - Miss Eva Mae - Girl Masker & Living Female

1 year ago

TrannyGem

shemale, crossdresser, chastity, rubber
16:48 33%

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

4 years ago

TrannyGem

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

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

1 month ago

TrannyOne

shemale, sissy, amateur, maid, chastity, bondage
25:00 25%

Black Tranny Jizz Jam - Episode 1

1 year ago

xHamster

black, big cock, shemale, chastity
11:59 20%

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

3 weeks ago

XXXVogue

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14:44 20%

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

4 months ago

ShemaleMovie

shemale, sissy, crossdresser, chastity
17:10 17%

Man Masturbates Off with Trans Lady in Purity

6 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

mom, femdom, prostate, dildo, 18, cartoon, chastity

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