SHEMALE • CHASTITY 4,285 videos

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07:20

Pearly Expanding - BIG BLACK COCK Ruthless Plumbing OCfemboy in Virginity Asscunt with Screwing Machine

1 year ago

TrannyGem

dildo, machine, sissy, chastity, femboy
03:56

AB097 Trampy nun degraded Sexual transformation -Edging,wring (Asian and English subtitles)

2 years ago

TrannyGem

handjob, chastity
08:31

Trans Woman in Chastity and Bondage Fucked

2 years ago

xHamster

bondage, chastity
14:04

Its time to lose your she-male chastity with a hot shemale slut

5 years ago

ShemaleMovie

chastity
18:25

Plastic shemale whore in chastity rides huge dildos

5 years ago

TXXX

huge dildo, fetish, dildo, riding, whore, chastity
17:44

Trancess Triss Introduces: Sissy rectal sesh with fuckmachine

3 years ago

TrannyGem

train, dress, machine, chastity
16:37

Guy Jerks Off With Trans Woman In Chastity 17 Min With Kelsey Masters

1 year ago

ShemaleZ

chastity, amateur
08:24

Sissy Candy in Crimson Undergarments Gets Spitroasted by Her Pounding Machine and Damsel

1 year ago

TrannyGem

fetish, lingerie, crossdresser, toys, machine, chastity
01:51

Locked up unicorn in chastity performs for mistress

4 years ago

xHamster

femdom, chastity
10:43

Cumming in chastity

1 year ago

AShemaleTube

masturbation, chastity, homemade
25:26

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

1 year ago

ShemaleZ

POV, ladyboy, shemale and girl, cum in mouth, chastity, femboy
15:30

Ash-Blonde Sissy Waits For Gang Fuck-Fest For Firm Bum Poking And Dual Anal Invasion Sissy Innocence Teaching

4 years ago

TrannyGem

train, husband, chastity
06:08 56%

Geile Gummipuppen - Teil2

3 years ago

ShemaleZ

latex, fetish, BDSM, ass to mouth, cum in mouth, domination, chastity
06:55

I like big toys!

2 years ago

xHamster

chastity
08:15

Striptease for you from sissy Oksana_ macro shot Asshole_sc.58

3 years ago

TrannyGem

strip, cosplay, chastity
02:55

Millie Rides Dildo In Chastity Pov

2 years ago

Upornia

chastity
01:57

Kelli makes herself leak with a jewel plug

3 years ago

xHamster

british, chastity
07:01

One of the best bitch in chastity suck a dick in public

6 years ago

ShemaleZ

mature, public, chastity
02:45

Strap-on Fuckers: Sissy Slut in Chastity Used by Her Domina

2 years ago

xHamster

femdom, strapon, chastity
07:35

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

5 years ago

BeMyHole

fisting, swallow, chastity
01:53

Pink Sissy Slut Locked in Chastity Goes Wild Riding Anal Dildo

3 years ago

xHamster

slut, chastity, femboy
15:08

Chastity and plug

5 years ago

xHamster

chastity
02:26

Take elevator in a whorey garment

10 months ago

TrannyGem

fetish, chastity
10:15

V-Card Encaged At Bedtime

5 years ago

TrannyGem

chastity
12:23

TGirl Lucy in V-Card gets penetrated by tearing up machine while fellating shaft

3 years ago

TrannyGem

dildo, redhead, machine, chastity
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
29:22

Imagining Im a Femboy make me Spreading Anal Invasion again

1 year ago

TrannyGem

teen (18+), teen anal (18+), 18, chastity
11:00

Trans Doll milks after College thinking about a Sensational Person (you)

1 year ago

TrannyGem

feet, big ass, dildo, milk, 18, masturbation, sissy
33:18

She Let Him Out Of Chastity

6 years ago

TXXX

chastity
05:06

Sissygasm in a negative chastity belt

1 year ago

xHamster

BDSM, chastity
08:10 88%

Dominatrix Fucks Sexy Sissy In Chastity

2 years ago

ShemaleZ

chastity, mature
06:38

Real Sissy Maid Service Dishes

2 years ago

xHamster

maid, cosplay, chastity
06:31

Sissy taniax Cum riding huge black dildo

1 year ago

xHamster

mature, mature anal, anal, dildo, chastity
12:41

I lost my t-girl chastity with 2 t-girls

6 years ago

KeekAss

teen anal (18+), compilation, handjob compilation, chastity
10:09

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

1 year ago

ShemaleMovie

shemale, chastity
15:57

Honey, TransMommy Needs Your Ass Again

7 months ago

BeMyHole

shemale, big ass, solo, chastity
01:20

HA49The female classmate has a chastity lock locked, three vibrators insert anal under skirt

1 year ago

AShemaleTube

outdoor, chinese, insertion, vibrator, skirt, chastity
08:06

Sissy Crossdresser - Trans Woman In Chastity Fucked Hard - Compilation 1

1 month ago

HClips

chastity, crossdresser, sissy, latex
02:44

I got stood up by my date!

3 years ago

xHamster

mature anal, chastity
06:08

Sissy Lucy Machine penetrated by Glowing faux-cock Whilst Locked In chastity

3 years ago

ShemaleTaxi

huge dildo, british, machine, chastity
01:09

Sissy cuming and peeing in a negativ chastity

1 year ago

xHamster

pissing, bondage, chastity
06:24

Hot Sissy In Chastity Fucks Herself With Her Big Dildo

2 years ago

ShemaleZ

chastity
02:25

Sissyslut Witnessing Mental Domination Vids in Iron Purity Box

3 years ago

TrannyGem

domination, slut, chastity
06:28

My latex girlfriend makes me vibrate in a cage

1 year ago

xHamster

amateur, latex, chastity, BDSM, bondage
01:09

First week in chastity

2 years ago

xHamster

public, cuckold, chastity
57:56

Sissy Lucys Toy Time In Chastity

4 years ago

HClips

chastity
04:28 75%

Taking It On All 4S Gets Her Every Time

1 year ago

TrannyGem

orgasm, chastity, machine
09:07

Sissy Charlotte locked in E-Stim chastity cage and getting pegged by MILF Lisa

3 years ago

xHamster

mature anal, pegging, chastity
01:02

Caged Daniela no hands cum

2 years ago

TrannyGem

chastity
06:31

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

1 year ago

ShemaleTaxi

chastity
07:21

Mitts Free-For-All Trans Cum-Shot Compilation 11

9 months ago

TrannyGem

chastity, cumshot compilation, compilation, cumshot
06:54

Sissyfas :: Spanish Cd In Chastity Enjoys Her Vibrating Plug In Ass - Teaser Video

2 years ago

GetTranny

vibrator, chastity, spanish
06:37

Sissy in chastity and pink fishnets having a 1l beer via anal in the open door

11 months ago

xHamster

amateur, chastity, crossdresser, sissy, public
05:25

Sissy In Chastity Taking Two Beers Via Anal. (two Beers Enema)

2 years ago

ShemaleZ

chastity
11:08

Sissy ejaculates in her box to white extinction BIG BLACK COCK dork pornography Breed black Angel scarlett Black

4 years ago

TrannyGem

femdom, natural, BBC, chastity
06:11

Lucy Essex CD And Lisa Playing With Our Toys In The Bedroom And Leaking Cum

4 years ago

BeMyHole

mature anal, orgasm, redhead, toys, chastity
06:15

Chastity sissy on fucking machine

8 years ago

TXXX

machine, chastity
05:58

Sissy Crossdresser DEEP Rectal Have Fun W/ Soles Eating & Deep Throating

2 years ago

TrannyGem

18, chastity
21:30

Sissy Fisting Ass Hard in Chastity

3 years ago

xHamster

mature, fisting, chastity, solo
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
02:03

Young Asian sissy in chastity cums handfree

2 years ago

xHamster

french, chastity
14:58

Sissy first-ever go with my shag machine while in my innocence

2 years ago

TrannyGem

machine, cosplay, chastity
12:54 85%

Innocence cockslut In ebony nylons And underwear Frolicking

4 years ago

TrannyGem

mature, pantyhose, stockings, british, prostitute, nylon, slut
01:12

Practice Makes Perfect

3 years ago

xHamster

chastity
05:42

Cute Trans In Chastity Cums From Anal

3 years ago

ShemaleZ

chastity, cum in ass
04:15

Sissy chastity pony buttplug

7 years ago

ShemaleZ

chastity
02:26

Sissy chastity enjoys with dildo

3 years ago

xHamster

turkish, sissy, chastity
13:09

Insanely deep Toy fucking. Using a Machine and more.

3 years ago

xHamster

german, machine, chastity
08:00

Sadie Rivers In A Chastity Cage Fucking Herself With A Blue Dildo 16 Min

2 years ago

GetTranny

chastity
10:00

VERY warm Crossdresser in pinkish chastity Fucked

9 months ago

ShemaleMovie

lingerie, BDSM, crossdresser, domination, sissy, chastity
07:52

Chastity desire Gudrun and Angie

5 years ago

AShemaleTube

chastity
02:23

Self Discipline Gullet Vag with Faux-Cock Gag.

8 months ago

TrannyGem

big cock, big ass, chubby, amateur, chastity, nipples
15:03

Sissy maid in chastity

4 years ago

ShemaleTaxi

pantyhose, maid, heels, chastity
04:36

Milfs Sissy Purity Instructing #BratPerversions

2 years ago

TrannyGem

femdom, strapon, chastity
06:30

Her First Sissygasm (fuck Machine Chastity Hands Free Cum)

2 years ago

GetTranny

chastity
02:23

BIG BLACK COCK Paramour

2 years ago

TrannyGem

BBC, hands free, chastity
09:33

Femboy With A Delightsome Shlong, Puts On Her Chastity Lock And Inserts An Ass-plug

4 years ago

ShemaleZ

insertion, chastity
02:23

Nip Getting Off While Thinking of Fuckpole with Buttfuck Magic Wand.

9 months ago

TrannyGem

shemale and girl, chastity, chubby, nipples
11:18

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

1 year ago

xHamster

dildo, cumshot, handjob compilation, cumshot compilation, chastity
03:43

Trans Woman Takes Twin Tail Creations Croxic In Chastity 4 Min

2 years ago

ShemaleZ

chastity
03:10

Sissy Susi dehnt Ihre Pussy mit Plug. Mit Chastity

4 years ago

AShemaleTube

chastity
13:47

Sissy tramp Pegging Compilation. female dom chastity

2 years ago

ShemaleTaxi

strapon, pegging, chastity, sissy
05:19

Sissy Lucy getting pegged in Chastity with the Beastli dildo

4 years ago

TrannyOne

pegging, sissy, chastity
36:55

Chastity boy puts together office chair in ballet heels

6 years ago

ShemaleZ

office, heels, chastity
06:24

Sissy Oksana striptease for BBC online

2 years ago

xHamster

strip, domination, chastity
18:24

Diamond Chastity - Motel Fun

3 years ago

ShemaleZ

hotel, chastity, brunette
05:19

Arms Free-For-All Rectal Ejaculation Sissygasm Cumpilation ten

2 years ago

TrannyGem

dildo, cumshot compilation, orgasm compilation, anal orgasm, chastity, prostate
15:07

Erica Cherry And Queenie Sateen In Submissive With Chastity Cage Makes Femdom Squirt A

1 year ago

ShemaleZ

blonde, femdom, chastity, shemale, squirt
20:15

Sissy Maids Bathroom Bondage, Locked to Toilet

3 years ago

xHamster

toilet, latex, bondage, maid, bathroom, chastity
02:35

Purity box eliminated for bad dragon sesh

2 months ago

TrannyGem

sissy, amateur, chastity
04:55

Sissy Dagmar321 plugged chastity cage whore

6 years ago

xHamster

mature anal, vintage, whore, chastity
07:25

Encaged Trans Doll spreads out lovely lil fuck-hole

1 year ago

TrannyGem

doll, bondage, cumshot, masturbation, sissy, chastity
11:22

Sexy sissy in Chastity sexyAsiansissy

4 years ago

AShemaleTube

chastity, sissy
09:30

SUPER SEXY blonde sissy removes chastity and then jerks off

1 year ago

JizzBunker

chastity
13:01 75%

Female Dominance hand-job for my sissy crossdresser

3 years ago

TrannyGem

femdom, bondage, chastity, shemale and girl
11:17

Pink Goth Maid in chastity part 2 rectal instructing

4 years ago

ShemaleTaxi

huge dildo, instruction, outdoor, maid, dildo, goth, mask
05:10

I put my machine on the highest setting and I had a sissygasm!

3 years ago

xHamster

train, machine, chastity
08:44

Sashas Dollhouse - Christmas Chastity And Dildo Ass Play

3 years ago

ShemaleZ

chastity
03:01

Laury Angel - Modern Ladies Have No Need For Pleasure Button

4 years ago

TrannyGem

squirt, orgasm, anal orgasm, chastity, dildo
13:27

Self Bondage 2 Litre Enema Hand Cuffed to Toilet in Chastity and Gagged

3 years ago

xHamster

toilet, gagging, bondage, chastity
13:39

Day six in innocence: Unboxing brand new metal chastity cage by myinside.es and edging me with vibrator

1 year ago

ShemaleMovie

stockings, shemale, anal, sissy, chastity
04:49

Petite Femboy Gets A Thick Assfuck Internal Ejaculation!

2 weeks ago

TrannyGem

dildo, sissy, chastity
04:16

Hitchhiking the behemoth man rod

2 months ago

TrannyGem

amateur, dildo, crossdresser, heels, sissy, gape, chastity
02:39

Sissy Crossdresser Dildo Play in chastity

5 years ago

xHamster

riding, chastity
08:54

Gudrun And Angie In Chastity And Pump Plug Games

4 years ago

Upornia

game, pump, chastity, amateur
02:59

After Exercise Anal Invasion Pulverize For Emma

6 months ago

TrannyGem

anal orgasm, sissy, hands free, orgasm, chastity, machine
10:43

Theresa Si training her bubble butt this time her ass plugged n clit locked, with a big steel plug and a chastity cage

3 years ago

xHamster

train, clit, big clit, chastity
02:48

Locked in chastity and using large dildo

2 years ago

xHamster

chastity
33:18

She Let Him Out Of Chastity

6 years ago

ShemaleZ

blowjob, chastity
27:05

Sissy Latexdoll Is Wearing Chastity

3 years ago

Upornia

chastity, amateur
09:47

Removes Chastity Then Jerks Off - Bailey Wilde

1 year ago

ShemaleZ

webcam, chastity
12:57

Chastity Sandy Shemale Fucked

6 years ago

xHamster

chastity
05:31 80%

Spandex sissy in purity and pummeled by Domme - AbbyKitty

4 years ago

TrannyGem

femdom, latex, bondage, spandex, chinese, heels, pegging
06:44

Sissy in vapid purity box railing a see-through pony fake penis

4 months ago

TrannyGem

train, dildo, crossdresser, riding, penis, sissy, chastity
06:22

A chastity contraption will keep you in your place

1 year ago

ShemaleTaxi

chastity
15:15

Ashley gets punished for removeing her chastity part 2 out of 3

6 years ago

ShemaleZ

chastity
02:00

Sissy rubberdoll in chastity fucking by dildo

6 years ago

xHamster

latex, BDSM, chastity
10:48 53%

Real sissy in in natures garb beach in chastity and rosebud

10 years ago

TXXX

beach, outdoor, natural, chastity
05:08

Huge tits and pumped lips for sissy bimbo Andreina

1 year ago

xHamster

cute, italian, crossdresser, chastity
17:08

Caged Sissy Slut Rides BBC Dildo Sex Toy

1 year ago

xHamster

dildo, BBC, chastity

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