SHEMALE • CHASTITY 561 videos

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26:44

Hot Chastity Sandy.

12 years ago

xHamster

chastity
20:48

A Sissygasm through Chastity

5 years ago

TrannyGem

orgasm, bondage, BDSM, BBC, chastity
24:46

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

1 year ago

ShemaleZ

femdom, BDSM, BBC, chastity, sissy
15:31

Trans slave in chastity made to bury her belongings by her Mistress

5 years ago

ShemaleZ

femdom, BDSM, chastity
16:12

Another anal training

1 year ago

xHamster

chastity
21:51

Self Suspension Bondage - Sissy Maid

1 year ago

xHamster

latex, bondage, maid, chastity
21:40

Sissy fisting Ass rigid in chastity

2 years ago

ShemaleTaxi

anal, fisting, toys, chastity, femboy, crossdresser
1:17:37

Yasmin Lee, Chastity, And Alissa Gangbang Guy

3 years ago

Upornia

gangbang, group, chastity
26:04

Sissy in Harness Fumble Herself with Fuck Stick and Rabbit, then Spunk in Innocence

2 years ago

TrannyGem

vibrator, chastity, cum in ass
16:48

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

3 years ago

TrannyGem

femdom, train, instruction, tease, crossdresser, JOI, sissy
22:38

The Life of Hatch and Butt Breezy

1 year ago

TrannyGem

teen anal (18+), 18, machine, cosplay, chastity
19:06

Sissy in chastity swallow cum

6 years ago

ShemaleZ

swallow, chastity
26:45

Naughty Chastity Sandy.

6 years ago

ShemaleZ

chastity
25:50

Super Hot sissy in crimson vinyl pounding a humungous 12 inch black fuck stick

1 year ago

TrannyGem

latex, huge dildo, chastity, crossdresser
18:25

Plastic shemale whore in chastity rides huge dildos

4 years ago

TXXX

huge dildo, fetish, dildo, riding, whore, chastity
18:51

Trans Female on Halloween toying with her fucktoys

2 years ago

TrannyGem

chubby, BBW, chastity
24:45

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

1 year ago

ShemaleZ

socks, erotic, chastity
31:05

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

1 year ago

ShemaleZ

dildo, chastity
19:47

Sissy Bitch Shagging Machine Ass Fucking Teaching and Good-Sized Playthings (long Version)

3 years ago

TrannyGem

train, huge dildo, mask, machine, chastity
49:11

Podcast Ep13: Sissy, Chastity and Lust

4 years ago

xHamster

chastity
40:46

Chastity cage on her penis,Asian she-male three way pulverized hard in the ass

2 months ago

ShemaleTaxi

asian, threesome, chastity, ladyboy, anal
17:35

Encaged Femboy Attempts to Spunk

2 years ago

TrannyGem

skirt, chastity
24:04

Lizz_ss25 changed sissy play

11 months ago

xHamster

chastity
15:30

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

3 years ago

TrannyGem

train, husband, chastity
17:39

Lily Star In Ass To Mouth And Leaking Out Of Chastity

2 years ago

ShemaleZ

ass to mouth, chastity, brunette
34:40

Voluptuous ebony shemale Chastity Michaels fucks the white dudes butt

7 years ago

TrannyOne

black, chastity
16:41

Sissy buttfuck training in chastity cage

5 years ago

HDSex

train, chastity
18:48

Trap In Chastity Cage Anal

3 years ago

ShemaleZ

blonde, chastity
25:01

Crossdresser fuck dildo with chastity cage

3 years ago

xHamster

dildo, chastity
16:14

Crossdresser gets machine fucked with XXL Monster Dildos #9

5 months ago

xHamster

german, crossdresser, machine, skinny, chastity, femboy
32:11

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

2 years ago

xHamster

mature, mature anal, BDSM, erotic, machine, chastity
24:37

Skitty in Anal Plug progression Stretching

2 years ago

xHamster

german, train, chastity
31:16 65%

Pathetic Chastity and Satin unexperienced sissy cam biotch gets used by online Daddy w/ CUMSHOT

12 months ago

ShemaleTaxi

anal, satin, crossdresser, cumshot, masturbation, sissy, chastity
17:44

Trancess Triss Introduces: Sissy rectal sesh with fuckmachine

2 years ago

TrannyGem

train, dress, machine, chastity
15:49

Barebacked Lizzy Yum - Welcome Home Lizzy- BDSM Female Chastity Post Op Pussy Masturbation Orgasm

1 year ago

BeMyHole

orgasm, BDSM, chastity, post op, shemale fucks guy
18:52

Sissy Hope great, hot and private compilation moments.

5 months ago

xHamster

small cock, latina, compilation, big cock, mexican, sissy, chastity
16:11

Schoolgirl crossdresser desperately tries to cum having a chastity cage (cum replay in slow-motion)

10 months ago

xHamster

riding, mexican, chastity
22:39

Sissy in chastity pushing bananas in and out of her boipussy

6 months ago

xHamster

pantyhose, stockings, mexican, asshole, chastity
15:05

Its time to lose your chastity to a transgender princess

1 year ago

ShemaleTaxi

threesome, taxi, chastity
33:48

She Let Him Out Of Chastity

5 years ago

ShemaleZ

chastity
25:00

Black Tranny Jizz Jam - Episode 1

3 months ago

xHamster

black, big cock, shemale, chastity
23:19

Ghotic trap solo in chastity

5 years ago

ShemaleZ

chastity
25:26

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

11 months ago

ShemaleZ

POV, ladyboy, shemale and girl, cum in mouth, chastity, femboy
16:05

Chastity Orgasm by Sissy Mindy

10 months ago

xHamster

chastity
17:00

Sissy trap blows her fuck stick than drills it (Total movie)

3 years ago

TrannyGem

chastity
18:13

Handsfree sissygasm for a dirty bitch in chastity

6 years ago

xHamster

hands free, chastity
17:08

Caged Sissy Slut Rides BBC Dildo Sex Toy

11 months ago

xHamster

dildo, BBC, chastity
25:50

Hot sissy in red PVC fucking a huge 12 inch black dildo

1 year ago

xHamster

latex, mature anal, huge dildo, british, chastity
15:07

Encaged Trap Railing Faux-Cock and Stimulating Cell to Ejaculation 4K

3 years ago

TrannyGem

pissing, teen anal (18+), panties, wet, socks, skirt, chastity
20:15

Sissy Maids Bathroom Bondage, Locked to Toilet

2 years ago

xHamster

toilet, latex, bondage, maid, bathroom, chastity
27:49

Working From Home As A Chastity Sissy Secretary Is So Much Fun

1 year ago

ShemaleZ

fisting, secretary, chastity
1:01:40 64%

Gorgeous Hands Free Cum

6 years ago

ShemaleZ

hands free, chastity, creampie compilation
19:57

Sissy Joy pounded By Her mistresse With A thong On while Locked In Chastity

6 years ago

ShemaleZ

femdom, thong, chastity
33:59

Trans Latex Hands Free Cum Chastity Fuck Piss Drinkung

8 months ago

ShemaleZ

shemale, hands free, chastity, latex
20:10

SISSY SHOOTS A LOAD IN INNOCENCE AFTER five DAYS OF VIRGINITY JIZM IN MAN ROD BOX V-Card Jism Compilation

3 years ago

TrannyGem

behind the scenes, cumshot compilation, orgasm compilation, chastity
18:37

V-Card box switch suprize oral pleasure!

1 year ago

TrannyGem

cuckold, chastity, femboy
21:30

Sissy Fisting Ass Hard in Chastity

2 years ago

xHamster

mature, fisting, chastity
19:51

Sissy squirting in chastity cage

2 months ago

AShemaleTube

crossdresser, chastity
17:39

Sissy shoots its geyser in virginity to white extinction BNWO end white race

3 years ago

TrannyGem

femdom, cuckold, chastity
27:08

Trans Anal Of Chastity Sandy

9 years ago

TXXX

chastity
16:09

Easter special

8 months ago

xHamster

shemale, amateur, chastity, sissy, smoking
19:10

Nude sole FETISH from SISSY QUEEN + CHASTITY CUM + PEDICURE by Shemale VERONICA TABOO

3 years ago

ShemaleTaxi

feet, chastity
29:34

Sissy Maid in Armbinder and Ankle Cuffed to bed in Chastity

1 year ago

xHamster

pantyhose, maid, chastity
29:45

Daddy s little sissy slut erin showing her new chastity

7 years ago

TXXX

slut, chastity
15:15

Sissy in hog-tie, domme plays with electro-hitachi on innocence box

8 months ago

TrannyGem

femdom, bondage, BDSM, tied, electro, chastity
15:39

Sissy Oksana Is Closed In Chastity And Wants To Have An Anal

2 years ago

ShemaleZ

chastity
24:36

Asian Femboy Tries Out The New Dildo With Chastity Cage

1 year ago

HClips

dildo, 18, chastity, femboy, asian
20:23

Sandy solo

4 years ago

ShemaleZ

solo, chastity
36:55

Chastity boy puts together office chair in ballet heels

5 years ago

ShemaleZ

office, heels, chastity
16:59

Sissy Femboy uses vibro to taunt encaged fuck-stick

8 months ago

TrannyGem

chastity, crossdresser
15:03

Admirer demand two: LineAiguille. Gash tonguing, blowage, creamie and queening crossdressed in v-card

2 years ago

TrannyGem

mom, femdom, MILF, facesitting, chastity, crossdresser
29:47

Daddys Little Sissy hoe Erin Showing Her recent Chastity

6 years ago

ShemaleZ

BDSM, chastity
30:54

Naughty tranny schoolgirl Sasha de Sade locks herself in chastity

7 years ago

TrannyOne

chastity
40:39

Sissy In Red Nightie Fucks Her Ass While Locked In Chastity

1 year ago

ShemaleZ

chastity
23:48

Pinkish Grace trap in v-card doing deepthroath and buttfuck have fun

3 years ago

TrannyGem

erotic, chastity, sensual
19:40

Shemale samurai challenges you to take her chastity

5 years ago

ShemaleZ

toys, chastity
18:33

DEBBIE IN CHASTITY

5 years ago

ShemaleZ

chastity
17:40

Knotty escapade

2 years ago

TrannyGem

cute, bondage, chastity
21:40

New Deep Love Vol.1 - Episode 5

2 years ago

xHamster

chastity
20:38

Sissy instructing: how to spunk in innocence? Rail ever thicker faux-cocks to sissygasm

2 years ago

TrannyGem

train, instruction, tight, chastity, cum in ass
16:09

Encaged trap humping herself 4K

2 years ago

TrannyGem

pissing, panties, wet, skirt, chastity
53:05

Lizzy Yum april 2023-welcome home lizzy-BDSM FEMALE CHASTITY post op pussy masturbation orgasm

1 year ago

xHamster

orgasm, bondage, chastity, post op
15:03

Sissy maid in chastity

3 years ago

ShemaleTaxi

pantyhose, maid, heels, chastity
23:54

Sissy CD in Innocence, Jerked Dry, Handsfree Sissygasms, Fat Fuck Sticks, Ginormous Dirt, Cleanup, Rainbow, Sto

3 years ago

TrannyGem

fat, huge dildo, dildo, hands free, chastity
18:24

Sissy Maids Spiked Chastity Cage Self Bondage in New Boots

1 year ago

xHamster

bondage, boots, maid, JOI, chastity
28:18

Sissy Maids Self Bondage Armbinder and Chastity Belt

3 years ago

xHamster

latex, bondage, maid, chastity
16:00

In chastity and lingerie playing with my ass

6 years ago

xHamster

chastity
16:10

Mike Caboose Porks Sissy Charlotte While She is Locked in EStim Innocence Cell

2 years ago

TrannyGem

mature anal, monster, deepthroat, chastity
33:18

She Let Him Out Of Chastity

5 years ago

ShemaleZ

blowjob, chastity
19:22

Trap in chastity cell buttfuck

2 years ago

ShemaleMovie

blonde, skinny, chastity
24:34

Sissy Trans Mega-Bitch screws her Butt and jizzes in Virginity

11 months ago

TrannyGem

feet, dildo, chastity
17:40

Sissy milking and cumming handsfree... in chastity!!

7 years ago

xHamster

milk, hands free, chastity
15:04 47%

CROSSDRESSER PLAYS WITH MAN MEAT IN VIRGINITY BELT AND PANTYHOSE AND HIGH HIGH-HEELED SHOES

3 years ago

TrannyGem

pantyhose, bondage, cuckold, crossdresser, heels, shoes, chastity
57:56

Sissy Lucys Toy Time In Chastity

3 years ago

HClips

chastity
17:39

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

3 months ago

xHamster

chastity, sissy, fetish, toys
27:08

Trans assfucking Of V-Card Sandy

4 years ago

TrannyGem

chastity
17:37

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

3 months ago

TrannyGem

shemale, sissy, amateur, chastity
15:51

Sissy Female Dominance Compilation - Tusspuss

3 years ago

TrannyGem

femdom, strapon, facesitting, swedish, handjob compilation, domination, pegging
16:25

I cant wait to take your tranny chastity

4 years ago

HDSex

chastity
16:58

Ruined Orgasm In Chastity And Cbt For Lana Trap

3 years ago

ShemaleZ

teen (18+), fetish, orgasm, BDSM, toys, domination, chastity
15:02

Satisfy let me take your she-creature chastity

4 years ago

ShemaleMovie

bisexual, hardcore, 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
22:06

SISSY ATTEMPTS HOOK-UP MACHINE ON HER BUTTFUCK FUCK HOLE FOR THE VERY FIRST TIME.

6 months ago

TrannyGem

reality, sissy, chastity, femboy
15:15

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

5 years ago

ShemaleZ

chastity
19:19

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

5 months ago

TrannyGem

masturbation, femdom, chastity, mature, POV
23:50

Unlocking my sissy bitch to sound her like the poke fuck-hole she is!

7 months ago

TrannyGem

cute, femdom, bondage, BDSM, chastity
16:58

Fucking-machines Fucks TS-Girl in the Doggystyle, Ass Cum + Cock Cage

5 years ago

TrannyGem

huge dildo, russian, machine, clothed, chastity, cum in ass
19:59

Wholesome self facial cumshot CEI with futa orc (Expressed reupload+ feral) Chastity feminization Assfuck JOI/

2 years ago

TrannyGem

femdom, prostate, instruction, facial, shemale and girl, futanari, JOI
20:39

Chastity Slut using vibrator and came

6 years ago

AShemaleTube

vibrator, chastity
15:45

Sissy In Chastity Pounding Creampie Fuckmachine

2 years ago

ShemaleZ

chastity, sissy
22:08

Fuckmachine torture

1 year ago

xHamster

chastity
16:06

Schoolgirl 18+ Crossdresser Desperately Tries To Cum Having A Chastity Cage (cum Replay In Slow-motion)

7 months ago

Upornia

18, chastity, crossdresser
21:32

Simone having some more Fun with her Toys - Home Video

5 years ago

TrannyGem

ass to mouth, vibrator, chastity
26:49

Spiked Chastity Cage Self Bondage

2 years ago

xHamster

latex, huge dildo, bondage, chastity
27:31

Self Suspension Bondage - Sissy Maid

5 months ago

xHamster

latex, chastity, crossdresser, sissy, bondage
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
24:52

Chastity Sandy likes dark penises

5 years ago

ShemaleZ

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
33:50

She Let Him Out Of Chastity

6 years ago

ShemaleZ

chastity
16:39

Sissy in high stilettos and stocking pummels herself in a cowgirl stance

2 years ago

TrannyGem

train, heels, chastity

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