TRANNY • CHASTITY 2,073 videos

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01:01

Watching women blowjob pov and ruining my orgasm

2 years ago

xHamster

german, orgasm, BDSM, chastity
03:52

Teen Sissy In Chastity Plays With Toys

6 years ago

TXXX

chastity
10:48 47%

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9 years ago

TXXX

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20:15

Sissy Maids Bathroom Bondage, Locked to Toilet

3 years ago

xHamster

toilet, latex, bondage, maid, bathroom, chastity
01:02

Sissy Femboy Fingers Booty

3 years ago

xHamster

chastity, femboy, crossdresser
01:26

Caged anal fun

2 years ago

xHamster

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01:44

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9 years ago

xHamster

upskirt, chastity
07:48

Cute Teen Tranny in Chastity Toe Curl Dildo Fucking

5 years ago

ShemaleZ

chastity, dildo
18:24

Diamond Chastity - Motel Fun

3 years ago

ShemaleZ

hotel, chastity, brunette
08:10 88%

Dominatrix Fucks Sexy Sissy In Chastity

1 year ago

ShemaleZ

chastity, mature
02:44

Sissy attempting to get off in her pink diaper with a wand

2 years ago

xHamster

pissing, maid, diaper, dress, chastity
02:44

I got stood up by my date!

2 years ago

xHamster

mature anal, chastity
08:15

Amateur sissy fucks ass with dildo, whips clitty around in chastity and has sissygasm cum

1 year ago

xHamster

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09:07

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

2 years ago

xHamster

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05:49

Bambi Christa's Reverse Striptease

3 years ago

xHamster

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29:47

Daddys Little Sissy hoe Erin Showing Her recent Chastity

7 years ago

ShemaleZ

BDSM, chastity
02:38

PorchaeTS pounds her 2 biggest dildos while in chastity.

2 years ago

xHamster

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15:39

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

3 years ago

ShemaleZ

chastity
07:07

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2 years ago

xHamster

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06:58

Hot Trans Woman In Chastity Leash And Bondage Bdsm Fucked

2 years ago

ShemaleZ

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08:29

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3 years ago

xHamster

femdom, chastity
02:12

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3 years ago

xHamster

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07:41

Chastity life

6 years ago

ShemaleZ

latex, chastity
18:33

DEBBIE IN CHASTITY

5 years ago

ShemaleZ

chastity
10:12

Transgender Slut Lilith Eclipse Fisting Herself And Playing With Her Asshole In A Tiny Chastity Cage And Dark Pantyhose

2 years ago

ShemaleZ

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03:08

HUGE ASS TS in Chastity Fucked Missionary

2 years ago

xHamster

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03:02

Trans Girl In Chastity Plays With Her Vibrator

1 year ago

ShemaleZ

chastity
10:53

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3 years ago

ShemaleZ

cosplay, chastity
06:17

CHASTITY BELT

5 years ago

ShemaleZ

latex, chastity
05:19

Asian Crossdresser In Chastity Dildo Play

2 years ago

ShemaleZ

indonesian, chastity, crossdresser
25:50

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2 years ago

xHamster

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12:42

Crossdresser femboy Sissy Kat leaks in chastity and sissygasms

6 years ago

ShemaleZ

chastity
04:15

TS in Bondage and Chastity Masturbating with Guy

2 years ago

xHamster

bondage, chastity
01:17

Crossdresser rubbing their clits in chastity to each other

5 years ago

xHamster

clit, big clit, chastity
03:11

Sissy In Slutty And Chastity Cage Gets Ass Up To Take A Full Bottle Of Beer In The Ass - Mini Dress

2 years ago

ShemaleZ

bottle, dress, chastity
12:39

Femboy Dressed As A Nun & Black Wings Fucks Huge Dildo And Cum After 10 Days In Chastity

3 years ago

ShemaleZ

huge dildo, nun, dress, chastity, femboy
03:04

Putting myself into chastity for loctober. The ring is very tight, that's why I'm struggling a bit in the beginning.

1 year ago

xHamster

bondage, chastity
18:24

Sissy Maids Spiked Chastity Cage Self Bondage in New Boots

1 year ago

xHamster

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10:35

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1 year ago

xHamster

chastity
01:29

Scooby Doo Fucks Sexy Trans Woman in Chastity

2 years ago

xHamster

chastity, cum in ass
01:55

Sissy put on chastity belt

4 years ago

xHamster

chastity
07:02

Cow Femboy In Chastity

1 year ago

ShemaleZ

stockings, femboy, chastity
01:25

Elmo Fucks Tgirl in Chastity

2 years ago

xHamster

chastity, cum in ass
07:16

Chastity submited and fucked

7 years ago

TXXX

chastity
01:04

Transgender in Chastity, Leash, and Bondage Fucked

2 years ago

xHamster

bondage, chastity
11:06

Holy Nun Astrid Apathy Sissygasm In Chastity

3 years ago

ShemaleZ

nun, skinny, chastity
03:37

Horny slut ride dildo

2 years ago

xHamster

italian, dildo, chastity
16:00

In chastity and lingerie playing with my ass

6 years ago

xHamster

chastity
22:08

Fuckmachine torture

2 years ago

xHamster

chastity
27:49

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

2 years ago

ShemaleZ

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29:45

Daddy s little sissy slut erin showing her new chastity

8 years ago

TXXX

slut, chastity
05:12

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1 year ago

xHamster

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01:44

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2 years ago

xHamster

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08:09

Trans Girl Riding Bad Dragon Chance In Chastity

2 years ago

ShemaleZ

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06:32

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2 years ago

HClips

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02:57

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3 years ago

xHamster

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03:09

Sissy Sherri Fucked While Tiny Cock Is Caged In Chastity

2 years ago

ShemaleZ

chastity, sissy
12:23

I enjoyed that big Toy so much i had to come

2 years ago

xHamster

german, chastity
04:06

Cute Blonde Cums RIght Into Her Mouth Through Her Chastity Cage

2 years ago

xHamster

cute, chastity
07:01

A Great Time with Bad Dragon Sveinn

2 years ago

xHamster

chastity
06:24

Hot Sissy In Chastity Fucks Herself With Her Big Dildo

2 years ago

ShemaleZ

chastity
01:21

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2 years ago

xHamster

chastity
05:32

Chantals tiny Clitty is caged in super small Chastity and she is fucked until juicy Sissygasm

2 years ago

xHamster

slut, chastity
04:32

Mara Jade In Inverted Chastity Cages Makes You Feel So Slutty & Submissive 5 Min

1 year ago

Upornia

amateur, chastity
05:04

Charlotte See Goode

1 year ago

xHamster

french, chastity
04:04

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

2 years ago

ShemaleZ

dildo, chastity, cum in ass
01:16

Oiled sissy body in small chastity

1 year ago

xHamster

swedish, chastity
13:51

Sissy Maid Self Bondage Armbinder In Chastity Harness Gag With Large Black Dildo Locked In Ass

2 years ago

HClips

latex, gagging, bondage, maid, sissy, chastity
10:53

Sissy destroys her ass while is chastity

1 year ago

xHamster

dildo, british, chastity
09:53

SisK caged and plugged EP1: Red swimming suit

1 year ago

xHamster

chastity
10:15 45%

Jessica Bloom Riding Monster Dildos Multiple Anal Orgasms in Chastity

3 years ago

xHamster

orgasm, monster, anal orgasm, chastity
17:11

Guy Jerks Off with Trans Woman in Chastity

2 years ago

xHamster

fetish, 18, jerking, chastity
02:24

Man Dressed as Woman in Chastity and Strapon Fucked

1 year ago

xHamster

strapon, crossdresser, dress, sissy, chastity, femboy
01:15

Chastity Sissy fucked by Machine

3 years ago

xHamster

german, machine, chastity
03:45

Sissy TGirl Lucy Pissing In Her Chastity Cage at SheWorld

5 years ago

xHamster

pissing, chastity
07:59

FIRST SISSYGASM Chastity Slut Misty Cane Cums in her Cage with vibrating wand

3 years ago

xHamster

vibrator, slut, JOI, chastity
02:03

Sissy Boy Pink Dildo Fuck

1 year ago

xHamster

chastity
02:15

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7 years ago

xHamster

chastity
10:12

Transgender Slut Lilith Eclipse Fisting Herself and Playing With Her Asshole in a tiny Chastity Cage and Dark Pantyhose

2 years ago

xHamster

pantyhose, fisting, goth, asshole, slut, chastity
04:17

Trans Woman in Chastity Fucked Cowgirl Raw

2 years ago

xHamster

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08:19

Sexy Sissy in Chastity Strapon Fucked by Dominatrix

1 year ago

xHamster

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04:18

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2 years ago

xHamster

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07:28

Femboy Sissy Plays In Chastity

3 years ago

HClips

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07:40

Femboy Taking The Chastity Cage Off To Finally Cum Hard

2 years ago

ShemaleZ

chastity
03:43

Sissy sarah in chastity shaving

2 years ago

xHamster

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01:30

Paula - In chastity riding on a dildo again

9 years ago

xHamster

dildo, chastity
01:04

Cumming Like a Good Slut

1 year ago

xHamster

chastity
05:24

Sexy sissy maid in chastity suck dick

11 months ago

xHamster

crossdresser, chastity, amateur, sissy, blowjob
05:29

Sissy Locked in Chastity Fits 11 Inches Down Her Throat

2 years ago

xHamster

chastity
10:22

Dildo fuck with Dragon toy

1 year ago

xHamster

anal, dildo, chastity, sissy
01:55

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2 years ago

xHamster

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01:58

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3 years ago

xHamster

chastity
36:55

Chastity boy puts together office chair in ballet heels

6 years ago

ShemaleZ

office, heels, chastity
09:39

Sissy Tammy fucks sex machine while in chastity.

3 years ago

xHamster

machine, chastity
06:15

Chastity Gets Vibrated Her Clitty Projectile Squirt Cummies Her Tiny Balls Spanked & Turning The Fuck Machine Up To Its Max!

1 year ago

Upornia

squirt, spanking, machine, vibrator, chastity
04:02

HUGE ASS TS in Chastity Fucked Doggystyle

2 years ago

xHamster

BDSM, dogging, chastity
33:59

Trans Latex Hands Free Cum Chastity Fuck Piss Drinkung

1 year ago

ShemaleZ

shemale, hands free, chastity, latex
03:55

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2 years ago

xHamster

chastity
02:28

Chubby sissy gets to wand in chastity

2 years ago

xHamster

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09:57

Chastity Sissygasm Compilation Encouragement Bloom With Sissy Jessica And Feet Slave

8 months ago

HClips

feet, outdoor, fisting, compilation, sissy, chastity
01:41

First Time Rapper Fucks TS in Chastity

2 years ago

xHamster

first time, chastity
06:23

Chastity Sissy & Fuck Machine

6 years ago

ShemaleZ

machine, chastity
03:25

Chastity diary Part 4

1 year ago

xHamster

chastity
13:27

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

3 years ago

xHamster

toilet, gagging, bondage, chastity
36:02

Crossdresser gets machine fucked with XXL Monster Dildos #2

12 months ago

xHamster

german, dildo, lingerie, crossdresser, monster, chastity
02:55

Tranny in chastity and nylon with big tits

5 years ago

xHamster

nylon, chastity
01:27

Elmo Fucks Transgender in Chastity

2 years ago

xHamster

chastity
27:08

Trans Anal Of Chastity Sandy

7 years ago

ShemaleZ

chastity
10:16

10 Min Dildo Fucking while locked up in

2 years ago

xHamster

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11:08

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7 years ago

TXXX

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05:49

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4 years ago

ShemaleZ

chastity
09:30

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4 years ago

HClips

dildo, chastity
01:33

Sissy locked in PVC Diaper and Chastity

3 years ago

xHamster

pissing, pantyhose, diaper, domination, chastity
03:14

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4 years ago

xHamster

chastity, sissy
14:38

Fan Request 2: Lineaiguille. Pussy Eating Blowjob Creamie And Facesitting Crossdressed In Chastity

2 years ago

ShemaleZ

facesitting, shemale and girl, chastity
05:19

Transvestite Annie A Horny Mans Daughter Who Squirts So Much That Her Chastity Belt Becomes Soaked

2 years ago

ShemaleZ

squirt, chastity
08:52

Ice un the Ass

1 year ago

xHamster

chastity
07:56

Transgender in Chastity Deepthroats

2 years ago

xHamster

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03:31

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3 years ago

xHamster

JOI, chastity
07:16

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5 years ago

xHamster

chastity

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