TRANNY • CHASTITY 2,058 videos

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09:29 40%

Hotwife Fucks Her BBC Bull As Sissy Cuckold In Lingerie And Chastity Cage

5 years ago

ShemaleZ

cuckold, chastity
11:24 40%

Real sissy in chastity outdoor

7 years ago

ShemaleZ

latex, outdoor, sissy, chastity
05:16 33%

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

7 months ago

xHamster

pissing, beauty, stockings, fetish, outdoor, crossdresser, nylon
19:15 30%

Sissy punished and fucked for removeing her chastity part 3 final

6 years ago

ShemaleZ

fetish, interracial, sissy, chastity, bareback
12:31 29%

Sissy Slut Whore

7 months ago

xHamster

small cock, shemale, dildo, solo, latina, crossdresser, whore
19:06 29%

Sissy in chastity swallow cum

10 years ago

xHamster

latex, swallow, sissy, chastity
06:25 29%

Gina in chastity, pleased and spanked

5 years ago

xHamster

mature anal, spanking, chastity
25:00 25%

Black Tranny Jizz Jam - Episode 1

1 year ago

xHamster

black, big cock, shemale, chastity
26:00 20%

Selfbondage latex - Chastity, nose mask p2

3 years ago

xHamster

latex, french, heels, mask, chastity
06:29 17%

Such a Happy SpitRoasted Sissy Slut, Her Holes So Full

5 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

3 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
08:25

Cute Tgirl In Chastity Self Facial

3 months ago

HClips

facial, solo, amateur, chastity, cute
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
05:17

Man Put in Chastity and Dressed as Maid for Job

1 year ago

xHamster

BDSM, uniform, crossdresser, dress, domination, sissy, chastity
09:39

Fucking Machine Anal Orgasms Chastity Foot Slut Jessica Bloom 10 Min

3 months ago

HClips

feet, POV, orgasm, machine, slut, anal orgasm, chastity
07:25

Sissy Maid Cums & Squirts Hard from Anal Fucking Machine in Chastity Cage - Jessica Bloom

1 year ago

xHamster

beauty, squirt, prostate, dildo, machine, sissy, chastity
26:15

Naughty Chastity Sandy.

5 years ago

TXXX

chastity
06:45

Twinkerbell Pegging The Lost Femboi With Feminization And Chastity

9 months ago

HClips

chastity, shemale, amateur, pegging
18:48

Cute Femboy Fucks Big Cock In Chastity Cage And Cums Hot

6 months ago

HClips

shemale, solo, chastity, femboy
04:49

Variety Itsol In Teases Her Girlcock In Chastity Cage

2 years ago

Upornia

chastity
20:08

Sissy Maid Self Bondage in Spiked Chastity Cage

3 years ago

xHamster

latex, bondage, maid, chastity
24:42

Crossdresser gets machine fucked with XXL Monster Dildos #5

1 year ago

xHamster

german, dildo, crossdresser, hardcore, chastity
05:50

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

8 months ago

xHamster

train, prostate, orgasm, fisting, dildo, british, swallow
14:57

Chastity sissy forced to cum by Mistresses

5 years ago

ShemaleZ

femdom, chastity
27:10

Chastity fucked

8 years ago

ShemaleZ

chastity
05:15

SISSY SLUT SHOWS OFF AND PUSHES OUT BUTT PLUG

1 year ago

xHamster

pantyhose, teen (18+), teen anal (18+), crossdresser, sissy, chastity
09:43

Vibrating my clit, chastity fail ends in self suck!

1 year ago

xHamster

facial, selfsuck, cum in mouth, vibrator, chastity
02:10

Releasing my sissy clitty from inverter chastity cage

2 years ago

xHamster

clit, chastity
03:52

Sissy Cumming In Her Chastity Cage

2 years ago

ShemaleZ

sissy, chastity
08:48

Hot sissy in tiny chastity cage masturbates with vibrator

2 years ago

xHamster

crossdresser, sissy, chastity, polish
06:42

Sissy In Chastity In Black Stockings And Boots Riding Large Green Dildo

2 years ago

Upornia

boots, dildo, sissy, chastity
11:22

Thick chubby Femboy needs a BBC

12 months ago

xHamster

femboy, BBC, sissy, chubby, big ass
16:14

Crossdresser gets machine fucked with XXL Monster Dildos #9

1 year ago

xHamster

german, crossdresser, machine, skinny, chastity, femboy
05:16

How to wear a flat chastity cage

1 year ago

xHamster

italian, webcam, sissy, chastity, mature
08:49

Ladyboy Fukk New Tiny Chastity

1 year ago

ShemaleZ

toys, chastity, asian
17:28

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

1 year ago

xHamster

cumshot, hands free, chastity, cum in ass
01:45

Pizza Delivery Guy Fucks Transgender Woman in Chastity

2 years ago

xHamster

chastity, femboy
09:50

Trans Anal Fisting And Prolapse In Chastity

2 years ago

ShemaleZ

fetish, fisting, BDSM, chastity
04:26

Cute femboy in chastity cage masturbate with vibrator

2 years ago

xHamster

vibrator, chastity
06:51

Sissylucylove Shemale Chastity Bull Busting

3 years ago

ShemaleZ

webcam, chastity
13:23

Ts Hucow Sissy In Chastity Vibrator Orgasm - Bimbo Slut Makes A Cummy Mess In Her Cage!

3 years ago

Upornia

orgasm, vibrator, slut, chastity
01:55

Latex sissy nun fuck herself in chastity

5 years ago

xHamster

latex, nun, chastity
32:36

Chastity Sandy Loves Big Cocks

8 years ago

TXXX

bareback, chastity
33:30

Chastity male vs shemale

9 years ago

TXXX

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14:50

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10 years ago

xHamster

latex, slut, sissy, chastity
06:06

Fetish dresser babe gurl Andreina

1 year ago

xHamster

pantyhose, italian, solo, crossdresser, chastity
05:16

Good Bussy

1 year ago

xHamster

ebony, chastity
06:47

How a sissy spends her night

1 year ago

xHamster

ebony, black, dildo, chastity
15:06

Skitty in Soft slapping into Hard Sissygasm

2 years ago

xHamster

latex, german, chastity, sissy
10:43

Trans Women Use Dildo, Butt Plug, Vibrator, Chastity 11 Min With Kelsey Masters And Bailey Wilde

5 days ago

HClips

vibrator, chastity
10:07

VERY HOT Blonde Crossdresser in Chastity Fucked

1 year ago

xHamster

amateur, anal, crossdresser, sissy, chastity, femboy
06:00

Chastity Slave Get Milked While Licking Trannys Feet - FemdomAustriaTs

1 year ago

TXXX

feet, threesome, chastity
08:19

Sexy Sissy in Chastity Strapon Fucked by Dominatrix

1 year ago

xHamster

strapon, chastity, femboy
05:54

Tied up sissy in chastity cage with anal plug ready for fuck

1 year ago

xHamster

french, bondage, tied, chastity
01:54

Pissing nacked outdoor in my tiny chastity

1 year ago

xHamster

pissing, outdoor, bondage, chastity
15:54

Crossdresser On Live Webcam - Sissy Wears Chastity Belt

1 year ago

ShemaleZ

crossdresser, blonde, sissy, chastity
01:12

Sissy Haileydoll In Chastity Anal Training And Gapes

2 years ago

xHamster

dildo, chastity
31:05

Crossdresser Femboy Sissy-kat Gapes With A Bbc Dildo And Leaks In Chastity

2 years ago

ShemaleZ

dildo, chastity, femboy, sissy
01:17

Trans Woman in Chastity, Leash, and Bondage Fucked

2 years ago

xHamster

bondage, BDSM, chastity
01:45

Trans Beauty in Chastity Fucked

2 years ago

xHamster

chastity
03:43

Sissy Sarah In Chastity Shaving

2 years ago

Upornia

shaving, chastity
24:45

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

2 years ago

ShemaleZ

socks, erotic, chastity
12:24

Slutty Trans Bunny Lilith Eclipse Fucks Herself With Carrots In Chastity Ass To Mouth

2 years ago

xHamster

fisting, cum in mouth, sissy, chastity
08:08

Chastity Cage On Her Cock Oriental Shemale Orgy Fucked

3 years ago

Upornia

asian, orgy, chastity
08:43

Watch my ass take this 10inch cock deep and cum in chastity

3 years ago

xHamster

chastity, cum in ass
06:05

Cd Caged By Femdom Girlfriend Slave Cums In Chastity Ru

3 years ago

ShemaleZ

femdom, girlfriend, chastity
03:15

Sissy Sherri fucked while tiny cock is caged in chastity

5 years ago

xHamster

chastity
06:21

Gina in chastity, pleased and spanked

5 years ago

ShemaleZ

BDSM, spanking, chastity
21:33

Sissy in Chastity Pleasures Herself with Toys and Hypno

5 years ago

ShemaleZ

fisting, chastity
06:12

Sissy Sniffs Poppers in Chastity & Plays with Dildo

6 years ago

ShemaleZ

chastity
07:31

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

6 years ago

xHamster

mature, public, chastity
01:10

Masturbation in chastity belt

11 years ago

xHamster

chastity
05:06

Sissy Kelli walks a hotel corridor wearing a penis gag

7 months ago

xHamster

amateur, small cock, public, gagging, crossdresser, british, toys
15:39

Sissy playing with dildo until cumming

11 months ago

xHamster

dildo, solo, crossdresser, sissy, chastity, finnish
06:53

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
21:19

Twin Game

1 year ago

xHamster

handjob, crossdresser, compilation, chastity
10:04

Caged sissy rides pink dildo with anal orgasms

1 year ago

xHamster

stockings, prostate, dildo, crossdresser, anal orgasm, chastity
03:40

Bimbo Playroom

2 years ago

xHamster

machine, slut, chastity
10:14

Fucking Machine Anal Orgasms Chastity Foot Slut Jessica Bloom

5 months ago

xHamster

amateur, machine, chastity
08:40

Feminized Sissy Slave Dildo Anal Training and Sissygasm in Chastity

6 months ago

xHamster

BDSM, stockings, sissy, chastity
05:47

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

6 months ago

xHamster

shemale, chastity, riding, anal, dildo
10:45

Chastity Sissy Throat Training And Plapping Orgasm - Huge Cum Squirt And Swallow Jessica Blooom

6 months ago

xHamster

beauty, squirt, orgasm, british, swallow, blonde, chastity
05:48

Sexy sissy fisted while sliding a sounding rod deep in her chastity locked clit until squirting everywhere

7 months ago

xHamster

pissing, mature, squirt, fisting, small tits, sissy, chastity
15:36

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

10 months ago

ShemaleZ

chastity, femdom, squirt, shemale, lingerie
17:39

Chastity Guide : A review of all metal chastity cages!! - By Sissy Joyce

1 year ago

xHamster

chastity, sissy, fetish, toys
41:54

Sissy femboy in chastity cage ballbusts to hands free orgasm

1 year ago

xHamster

masturbation, chastity, BDSM
06:47

BBC Daemon Loki Breeds Femboy Trap Nun in Chastity MOROCCO 2024

1 year ago

xHamster

creampie, asian, chastity, mature, BDSM
11:17

Kelsey Masters In Trans Woman In Bondage And Chastity Masturbating With Guy 12 Min

1 year ago

ShemaleZ

latex, shemale, bondage, BDSM, chastity
05:07

Inverted Chastity Cages Make Me Feel So Slutty

1 year ago

xHamster

small cock, chastity, dildo
21:51

Teen tranny fuck her ass with big dildo

1 year ago

xHamster

dildo, chastity, femboy, sissy
32:38

Sissy Maid in Spiked Chastity Cage Cuffed to Bed Post

1 year ago

xHamster

maid, chastity
04:02

Slimsissyjessica motel dildo fuck in chastity

1 year ago

xHamster

pantyhose, hotel, chastity
02:55

Dominatrix Strapon Fucked Crossdresser in Chastity

1 year ago

xHamster

strapon, BDSM, chastity
02:55

Sissy walks around in denim mini skirt and shows her ass and penis in her chastity cage

1 year ago

xHamster

public, french, outdoor, skirt, chastity
03:56

My New Inverted Chastity Cage Comes w a Tiny Fake Diik Attachment

1 year ago

xHamster

pissing, chastity
03:07

18 year old puppy femboy in chastity has first anal orgasm

1 year ago

xHamster

orgasm, ladyboy, anal orgasm, chastity
12:48

Misr4 - chastity cage anal nipple sissygasms

2 years ago

xHamster

pissing, mature, dildo, nipples, hands free, chastity
24:46

Raver Sissy Femboy In Chastity Fucks Bbc 4 Femdom Goddess While She Eats Dinner, Rough Anal Slut 4/5

2 years ago

ShemaleZ

femdom, BDSM, BBC, chastity, sissy
04:04

Sissy Cd Slut Riding Dildo Training For Sissygasm In Chastity (almost Cum)

2 years ago

ShemaleZ

dildo, chastity, cum in ass
08:13

Trans Woman Riding Bad Dragon Chance In Chastity 8 Min

2 years ago

ShemaleZ

chastity
07:08

Femboy In Shibari And Tiny Chastity Riding Dildo And Sissigasming

2 years ago

ShemaleZ

chastity, femboy
04:11

White Dirty Sissy Slut Fuck by Huge BBC Dildo penetrated while Locked in Chastity

2 years ago

xHamster

huge dildo, chastity, femboy
05:10

Trans Woman in Chastity Fucked Missionary POV

2 years ago

xHamster

BDSM, missionary, chastity
08:27

Chastity Slave Loves To Spread

2 years ago

ShemaleZ

chastity
01:17

BBC on Fuckmachine Fuck Sissy in chastity cage

2 years ago

xHamster

latex, sissy, chastity
02:04

Rubberdoll Whore Masturbates in Chastity and Cums

2 years ago

xHamster

latex, cuckold, whore, chastity
04:06

Cute Sissy Cums in Her Own Mouth in Chastity

3 years ago

xHamster

cum in mouth, chastity
30:27

Rianna James In Cuckold Fantasy, Chastity, Small Penis Humiliation

3 years ago

ShemaleZ

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22:29

Kylie Maria In Kylie Cums In Her Chastity

3 years ago

ShemaleZ

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13:34

Putting On A Show In Chastity

3 years ago

ShemaleZ

chastity
06:16

Sissy In Plaid School Girl Miniskirt Gets Probed Deep By Hankeys Sigmaloid While In Pink Chastity

3 years ago

ShemaleZ

chastity, sissy
01:02

Instant Sissygasm Hands-free in Chastity

4 years ago

xHamster

mature anal, hands free, chastity
03:29

Sissy Begging Master To Let Him Out Of Chastity

4 years ago

ShemaleZ

chastity
03:14

Sissy chastity poppertrainer featuring sissy joyce

4 years ago

xHamster

chastity, sissy
05:24

Sissy Melissa getting an Orgasm in her Chastity Cage.

4 years ago

xHamster

femdom, orgasm, BDSM, chastity
08:33

Lilac Angora Tiny Chastity Huge BBC - Drip Milk Sissygasm

5 years ago

xHamster

huge dildo, milk, BBC, chastity
06:23

Sissy Gurl in Chastity Gets Some BBC

5 years ago

xHamster

BBC, chastity
06:21

Sophie, transvestite, outdoor butt plugged and chastity cage

5 years ago

xHamster

outdoor, lingerie, chastity
26:38

Trans anal Of Chastity Sandy

5 years ago

ShemaleZ

chastity

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