SHEMALE • CHASTITY 3,844 videos

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05:01

Ebony Tranny Chastity Michaels Fucks A Stud

4 years ago

xHamster

chastity
01:02

Sissy Femboy Fingers Booty

2 years ago

xHamster

chastity, femboy, crossdresser
09:30

Perfect Femboy In Chastity Plays With A Dildos

3 years ago

HClips

dildo, chastity
02:04

TsSamanthaDoll - Afternoon Anal Invasion Quickie

2 years ago

TrannyGem

chastity
08:42

Crossdresser in chastity and his daily dildo challenge

2 years ago

xHamster

german, mature anal, huge dildo, chastity
14:58

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

1 year ago

TrannyGem

machine, cosplay, chastity
05:41

Spandex sissy in chastity and smashed by dominatrix

1 year ago

ShemaleMovie

BDSM, chinese, chastity, spandex, sissy
13:28

Chubby Trans Sex Slave In Chastity Allowed To Peg Her Mistress

2 years ago

HClips

femdom, chubby, pegging, chastity
03:48

Sissy Kitten Lexi plugs her ass in a spiked chastity cage

4 years ago

ShemaleZ

chastity
15:02

Satisfy let me take your she-creature chastity

4 years ago

ShemaleMovie

bisexual, hardcore, chastity
08:06

Ladyboy gives her faux-cock a bj for the first-ever time

3 years ago

TrannyGem

first time, chastity
03:06

Sexy Trans Woman in Chastity Fucked Missionary

1 year ago

xHamster

missionary, chastity
11:27

Chubby Trans Girl Vibin

2 years ago

BeMyHole

fetish, chubby, BBW, ass, mask, toys, chastity
01:44

Sissy in Chastity, Panties, Thigh Highs and Heels Waiting for Cock

2 years ago

xHamster

panties, heels, chastity
07:07

Chastity with E-stimulation

2 years ago

xHamster

german, chastity
04:39

Dominatrix Fucks Sissy in Chastity

1 year ago

xHamster

chastity
02:44

I got stood up by my date!

2 years ago

xHamster

mature anal, chastity
05:17

Pretty Cross Dresser in Chastity fucking dildo

4 years ago

xHamster

mature anal, 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

2 years ago

TrannyOne

cuckold, husband, chastity
17:37

Virginity guide : A review of all iron purity cages by sissy joyce55

4 months ago

TrannyGem

shemale, sissy, amateur, chastity
06:47

Sis-k Pinky Chinese Dress Ep3: Fapping

3 months ago

xHamster

thai, chastity, small cock, solo, chinese
08:19

Cute Teen Tranny Bunny Chastity Toe Curl Dildo Fucking

3 years ago

AShemaleTube

chastity
03:17

NO HANDS sissygasm in Black stockings chastity

2 years ago

xHamster

dildo, hands free, chastity
06:58

Dildo Ride In Chastity Sissygasm

1 year ago

GetTranny

chastity
03:06

BLACK-TGIRLS: Chastity Kane Gives Love & Cheer

11 months ago

AShemaleTube

chastity
03:58

Hot guy in red lingerie cums wearing chastity cage

5 years ago

ShemaleZ

chastity
02:17

Hungry Anal Femboy Time-lapse in Chastity

2 years ago

xHamster

chastity
07:38

Chastity Dildo Riding

5 years ago

HClips

chastity, riding
06:32 85%

Purity sissy Raine toying with BIG FAKE PENIS

1 year ago

TrannyGem

cute, teen (18+), teen anal (18+), dildo, sissy, chastity
15:15

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

5 years ago

ShemaleZ

chastity
02:42

Sissy uncages and runs in rivulets droplets

1 year ago

TrannyGem

teen (18+), huge dildo, hands free, chastity
11:39

Sissy Oksana's anal training ends with multiple sissygasms_sc.12

1 year ago

xHamster

chastity
01:14

Trans Woman in Bondage and Chastity Fucked

1 year ago

xHamster

bondage, chastity
07:17

Mia The Shy Maid - Chastity Sissy Selfbondage Goes Wrong

2 years ago

ShemaleZ

maid, uniform, shy, chastity
13:47

Sissy tramp Pegging Compilation. female dom chastity

1 year ago

ShemaleTaxi

strapon, pegging, chastity, sissy
05:38

Trans sissy slut with blue hair going crazy with big dildos - MercurySissy aka Mercury Montana riding and training in chastity

5 months ago

xHamster

dildo, masturbation, chastity, femboy
10:07

Crossdresser gets machine fucked with XXL Monster Dildos #7

5 months ago

xHamster

monster, german, chastity, crossdresser
22:08

Fuckmachine torture

1 year ago

xHamster

chastity
02:32

FEMBOY SISSYBOY PLUG ANAL PLAY

1 year ago

xHamster

german, chastity
19:19

Horny Trans Mistress gives you POINT OF VIEW abjection. Virginity, Soles, Damsel Fuck-Stick, Spoken Degradation.

6 months ago

TrannyGem

masturbation, femdom, chastity, mature, POV
06:53

Chastity E-stimming

1 year ago

xHamster

german, chastity
02:39

Crossdresser chastity cb hands free cumshot

3 years ago

AShemaleTube

hands free, chastity
04:37

Getting Off with the v-card box liquidated

2 years ago

TrannyGem

pissing, bondage, 18, diaper, college, chastity
09:54

Pale Femboy Trap In Striped Stockings Beats Own Balls Escapes Chastity And Rubs Her Little Cock To A Limp Hands Free Cum

1 year ago

ShemaleZ

hands free, chastity
08:12

Sissy Dream 2

9 months ago

xHamster

german, chastity
01:11

Full body Latex catsuit

2 years ago

xHamster

latex, french, chastity
07:45

Part to of putting trying on the flat cage

5 months ago

xHamster

crossdresser, chastity, sissy
06:13

Sissy spunk with extraordinary rammed clittie

2 years ago

TrannyGem

train, chastity, cum in ass
04:51

Trans Woman Fucked In Bondage And Chastity

1 year ago

Upornia

fetish, bondage, chastity
13:04

Femboy sissy wide open booty and railing pulverize machine stiff - sissy jazzie

2 years ago

TrannyGem

machine, chastity
13:48

Sissy in Chastity Putting on a Show

5 years ago

TrannyGem

chastity
04:19

Caged clit cuming hard, no need to ever take it off again.

1 year ago

xHamster

german, clit, chastity
05:24

Sissy Chastity fuckmachine

12 months ago

xHamster

chastity
17:12

Day 5 In Chastity - Edging My Clit While Plugged And Go Back To Cage Without Cum

1 year ago

ShemaleZ

clit, chastity
07:51

Husband tortured in spiked chastity cage

5 years ago

ShemaleZ

MILF, husband, chastity
09:43

Sexy Trans Removes Chastity Then Jerks Off - Bailey Wilde

11 months ago

ShemaleZ

chastity
03:17

Encaged Trap Maid rails fuck stick and attempts despairingly to spunk

2 years ago

TrannyGem

tease, bondage, maid, chastity
10:43

You are going to lose your buttfuck chastity to a shemale

2 years ago

ShemaleTaxi

blowjob, bisexual, taxi, hardcore, chastity
07:28

Trans has sissygasm

2 years ago

TrannyGem

train, bondage, heels, anal orgasm, chastity
13:32

Insane victim nymph having joy boobies and spear

7 months ago

TrannyGem

beauty, 18, cumshot, old and young (18+), sissy, chastity
33:50

She Let Him Out Of Chastity

6 years ago

ShemaleZ

chastity
16:10

College Girl crossdresser despairingly attempts to jism having a v-card cell (jizm replay in slow-movability)

9 months ago

TrannyGem

chastity, cum in ass, crossdresser
01:19

Police Fucks Hot Trans Woman in Chastity

1 year ago

xHamster

police, chastity
03:53

Tgirl Fucked In Bondage And Chastity

1 year ago

ShemaleZ

fetish, bondage, chastity
02:02

Sissy Juliette cant stop leaking

1 year ago

TrannyGem

chastity
03:53

Tgirl Fucked in Bondage and Chastity

1 year ago

xHamster

bondage, chastity
10:15

Amazing Shemale in Chastity

4 years ago

AShemaleTube

chastity
05:11

Crossdresser Anani Waist Bull Bull Continuous Mesuki (Chastity Belt + Piston Machine)

4 years ago

BeMyHole

machine, chastity
01:13

Indian sissy niki rides dildo in chastity

1 year ago

xHamster

indian, chastity
06:58

Sissy Maid Struggling In New Armbinder And Steel Chastity Belt With 7 Dildo Locked Inside

7 months ago

GetTranny

maid, bondage, chastity, latex, sissy
02:10

Sissy Oksana shows you her gaping asshole

1 year ago

xHamster

chastity
11:13

Femboy with a very puny chastity cage gaping fuck hole with a big faux-cock and riding it

4 years ago

ShemaleTaxi

homemade, teen anal (18+), shaving, gape, chastity
09:45

Lizz_ss25 street hooker deep anal

11 months ago

xHamster

sissy, chastity
06:50

Kelsey Masters - Trans Woman In Chastity Fucked Cowgirl 7 Min

10 months ago

ShemaleZ

chastity
05:27

Femboy In A Chastity Belt Jerks Off Her Ass With A Big Dildo And Cums - Teaser Video

2 years ago

GetTranny

chastity
02:00

Sissy rubberdoll in chastity fucking by dildo

5 years ago

xHamster

latex, BDSM, chastity
20:12

Sissy Maid Cuffed Spread Eagle In Steel Chastity Belt And Huge Dildo

1 year ago

ShemaleZ

stockings, latex, huge dildo, maid, chastity
03:09

Crawling Hogtied with 10lb Weight Tied to Balls in Chastity and Gagged

2 years ago

xHamster

latex, gagging, bondage, tied, chastity
01:10

Sissy in Chastity Riding Big Dildo

7 years ago

xHamster

chastity
02:37

Sissy in chastity dildos ass with bbc dildo.

4 years ago

xHamster

chastity
01:13

Asian sissy milking in chastity

7 years ago

xHamster

milk, chastity
02:41

Smoking in V-Card with a Guts wand!

1 year ago

TrannyGem

smoking, chastity
10:31

I am going to take your t-girl chastity lovely and softly

3 years ago

KeekAss

compilation, chastity, interracial
02:55

Millie Rides Dildo In Chastity Pov

1 year ago

Upornia

chastity
01:42

Bubble Butt Sissy Slut Chantal Sweet in super tiny Chastity Cage has Sissygasm

1 year ago

xHamster

fat, german, chastity
06:32

Sissy Slut Anal Masturbation With Clit Closed In Chastity Sc.19

2 years ago

HClips

clit, slut, chastity, big clit
10:38

SisK release her penis from chastity device and play with her horny penis after her ass being plugged.

2 years ago

xHamster

thai, penis, chastity
10:02

Sissy Oksana numerous sissygasms on Sirs order_part 3_sc.71

2 years ago

TrannyGem

train, anal orgasm, chastity
01:29

TS in Chastity Fucked Doggystyle Raw

1 year ago

xHamster

dogging, chastity
58:26

Sissy Lucy's toy time in chastity

3 years ago

AShemaleTube

redhead, double anal, double penetration, chastity
14:46

Sissy Maid Self Bondage Torment

1 year ago

xHamster

bondage, maid, BDSM, chastity
04:51

Blackhair Delia Releases A Kept Man From Chastity Then Locks Him Down With Her Cock

2 years ago

BeMyHole

chastity
03:52

SISSYKAT HOTEL HALLWAY WALK

1 year ago

xHamster

hotel, chastity
06:47

BBC Daemon Loki Breeds Femboy Trap Nun in Chastity MOROCCO 2024

9 months ago

xHamster

creampie, asian, chastity
03:30

Playing with Myself, Sissy Victoria

1 year ago

xHamster

indian, chastity
01:03

Chastity Milking

4 years ago

xHamster

milk, chastity
12:05

Sissy Anal Training And Sissygasm In Chastity Sc.8

2 years ago

ShemaleZ

train, chastity
02:37

Sissy hoe Lee creeps in a fast rail before getting locked and cucked

7 months ago

TrannyGem

hardcore, chastity
04:47

Finally soaking all in. Sissy training in chastity, riding dildo.

1 year ago

xHamster

sissy, chastity
02:04

Riding a dildo while caged

2 years ago

xHamster

mature anal, riding, chastity
18:24

Diamond Chastity - Motel Fun

2 years ago

ShemaleZ

hotel, chastity, brunette
15:37

Sissy Slut Training

1 year ago

BeMyHole

stockings, train, fetish, toys, slut, chastity
27:05

Sissy Latexdoll Is Wearing Chastity

2 years ago

Upornia

chastity
14:42

Sissy Maid Armbinder Gas Mask Self Bondage in Chastity

2 years ago

xHamster

latex, huge dildo, bondage, maid, mask, chastity
05:19

Sexy Sissy Teasing U In Hot Lingerie And In A Small Chastity Cage

1 year ago

ShemaleZ

tease, chastity
10:04

Day 12 of 26 in innocence and denial. Vibing my box and speculum for taunting

3 years ago

TrannyGem

smoking, tease, heels, vibrator, chastity
01:17

Emily Austin cuckold creampie eating hot wife sex puts sissy into chastity

3 years ago

TrannyOne

wife, cuckold, cum in mouth, chastity
08:45

Femboy Fuckmachine Sexy Lingerie Electro Chastity

7 months ago

Upornia

lingerie, chastity, femboy, electro
19:58

Encaged Booty Teaching Sissy Silly Brandynette Lovense Hush 45mm Ass Fucking Butt-Plug

2 years ago

TrannyGem

goth, chastity
07:54

Shemale Mature In Chastity Playing With Dildos And Cum

1 year ago

GetTranny

mature anal, chastity, cum in ass
13:36

Self Bondage In Leather Fist Mitts Lycra Body Suit Tights Pvc Knee High Boots Gagged In Chastity

1 year ago

ShemaleZ

gagging, fisting, bondage, boots, spandex, leather, tight
04:02

SissyBree locked in chastity device

5 years ago

HClips

BDSM, chastity
14:51

Vibrating Sissy Cow Anal Toy & Chastity Show staring Sissy Mindy

11 months ago

xHamster

chastity
06:55

Tgirl In Chastity Fucked Cowgirl

1 year ago

ShemaleZ

latex, fetish, chastity
12:31

Permanent chastity sissy ruined by 10s

1 year ago

ShemaleTaxi

chastity, sissy
05:36

Sissy lara cams for men like a fine gal

2 years ago

TrannyGem

dildo, chastity
07:11

Hot Trans Woman In Chastity Fucked Cowgirl 7 Min With Kelsey Masters

8 months ago

ShemaleZ

latex, chastity
04:51

She TRULY Luvs To Stroke Her Fuck Stick ❤️ 4K

2 months ago

TrannyGem

sissy, chastity, amateur, hands free
07:11

Sissy Nun Astrid Apathy Has Sissygasm In Chastity

1 year ago

GetTranny

bath, sissy, chastity
15:25

In Chastity Cage And Butt Plug

1 year ago

ShemaleZ

chastity

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