TRANNY • CHASTITY 2,041 videos

Popular Latest Top rated

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06:20

Chastity gets Vibrated Her Clitty Projectile Squirt Cummies, her tiny balls SPANKED, & Turning the Fuck Machine Up to its Max!

1 year ago

xHamster

squirt, machine, chastity
05:46

Sissy with big ass in fishnet showing her ass and cock in chastity cage

2 years ago

xHamster

german, chastity
08:19

Chastity Caged At Bedtime

3 years ago

HClips

chastity
01:30

Chastity Day 3 of 90

7 years ago

xHamster

chastity
06:38 75%

Sissy Lucy Gets Spanked In Chastity 7 Min

4 years ago

HClips

spanking, chastity
05:19

Haired Trans Girl Fucked Doggy Style In Chastity Wearing Pink Corset And Skirt

2 years ago

Upornia

dogging, skirt, chastity
19:00

Sissy Lucy being locked in metal Chastity for Locktober

4 years ago

xHamster

couple, BDSM, 18, chastity
26:00

Casey The Anal Slut In Chastity Plays With Her Toys Part 2

3 years ago

ShemaleZ

MILF, slut, chastity
22:29 88%

Kylie Maria In Kylie Cums In Her Chastity

3 years ago

ShemaleZ

chastity, brunette, webcam
01:12

Cop Fucks Trans Woman in Chastity

2 years ago

xHamster

BDSM, 18, chastity
24:42

Crossdresser gets machine fucked with XXL Monster Dildos #5

1 year ago

xHamster

german, dildo, crossdresser, hardcore, chastity
11:24

Skitty in Pump it Up

3 years ago

xHamster

german, pump, chastity
05:52

Hot Sissy Anal Slide In Chastity Cage

2 years ago

HClips

chastity
15:20

SisK plug and play her anal with a purple vibrator under her white skirt.

1 year ago

xHamster

stockings, thai, masturbation, skirt, chastity, femboy
15:06

Skitty in Soft slapping into Hard Sissygasm

2 years ago

xHamster

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09:35

Doms Put A Leash & A Chastity Cage On - Lauren Phillips, Tony Orlando And Crystal Thayer

3 years ago

ShemaleZ

small cock, threesome, chastity
08:50 62%

Slut Cums Into her Own Mouth, Multiple Sissygasms, While Sounding, Vibrator on Her Chastity Cage, In the Woods, Etc!

1 year ago

xHamster

small cock, public, solo, cum in mouth, skinny, chastity
06:29

Sissy Boy Cums In Chastity For Daddy

2 years ago

Upornia

sissy, chastity
04:00

Locked in a chastity belt Sonechka filled her ass with her lube ruined sissygasm

2 years ago

xHamster

chastity
08:13

Sexy Sissy In Chastity Strapon Fucked By Dominatrix

1 year ago

ShemaleZ

strapon, chastity
04:50

Sissy Dagmar321 plugged chastity cage whore

6 years ago

HClips

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04:18

Bimbo slut anal practice!

3 years ago

xHamster

slut, sissy, chastity
06:18

Sissy in School Girl Onesie Takes Dildo Up Ass while in Chastity

1 year ago

xHamster

dildo, sissy, chastity, crossdresser
09:41

Slutty Trap Solo In Small Pink Chastity

12 months ago

HClips

amateur, chastity, stockings
01:01

Velma does dirty things!

3 years ago

xHamster

chastity
06:01 78%

Chastity sissy anal training with huge black dildo

6 years ago

ShemaleZ

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03:42

Dont Think About My Pussy Chastity Bitch

6 years ago

ShemaleZ

fetish, BDSM, chastity
04:20

Chubby trap in chastity gets fingered fucked

4 years ago

xHamster

fat, chubby, BBW, chastity, cum in ass
03:40

Sissy TGirl Lucy Pissing In Her Chastity Cage at SheWorld

5 years ago

HClips

pissing, sissy, chastity
07:42

Sissy Lucy in chastity ass fucked by huge dildo

4 years ago

xHamster

mature anal, huge dildo, chastity
09:47

Sissy Maids Self Suspension Bondage

3 years ago

xHamster

bondage, maid, sissy, chastity
04:33

Chastity masturbation with cumshot

4 years ago

xHamster

dildo, vintage, chastity
07:56 67%

Pink Sissy Locking Her Tiny Limp Clitty In The Smallest Chastity Cage

4 years ago

ShemaleZ

chastity
06:58

Cute Tgirl Playing With Chastity Cage And Cum Delay Until Open It

3 years ago

ShemaleZ

cute, toys, chastity
06:21

Sophie, transvestite, outdoor butt plugged and chastity cage

5 years ago

xHamster

outdoor, lingerie, chastity
02:19

Chastity Loads of cum

2 years ago

xHamster

hands free, chastity
03:04

Sissy in small chastity gets fucked with a BBC

2 years ago

xHamster

latex, BDSM, BBC, chastity
04:34

Big Dildo In Ass And Chastity. No Cum! - Amanda S

3 years ago

ShemaleZ

chastity, cum in ass
03:28

Sissy Jenna’s Anal Orgasm in Chastity

6 years ago

ShemaleZ

orgasm, anal orgasm, chastity
07:25

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

1 year ago

xHamster

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13:29

Sissylucylove Trans Cum And Eat My Cum Chastity Selfsuck Edge

3 years ago

ShemaleZ

selfsuck, chastity
08:27

Chastity Slave Loves to spread

2 years ago

xHamster

chastity
19:57

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

6 years ago

ShemaleZ

femdom, thong, chastity
03:56 80%

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

2 years ago

xHamster

pissing, chastity
11:52

Trans Woman in Chastity, Leash, and Bondage Masturbating

2 years ago

xHamster

bondage, BDSM, chastity
01:11

Sissy Lucy posing in chastity and bodycon dress

5 years ago

xHamster

dress, chastity
26:15

Naughty Chastity Sandy.

6 years ago

ShemaleZ

chastity
16:51 70%

Cute pink haired trans woman masturbating in chastity

3 years ago

xHamster

cute, dildo, BDSM, anime, chastity, solo
02:56

Sissy sarah hypno locked up chastity

4 years ago

xHamster

chastity
09:39

Femdom strapon Chastity And sperm Feeding Compilation

6 years ago

ShemaleZ

femdom, strapon, sperm, domination, cumshot compilation, chastity
03:55

Trans Woman Cowgirl Fucked In Chastity 4 Min - Kelsey Masters

1 year ago

ShemaleZ

chastity, latex
14:36 60%

Fed My Own Cum Strapped to Fucking Machine Chair in Chastity - Sissy Maid

2 years ago

xHamster

latex, bondage, maid, BDSM, machine, chastity
09:22

Ilandis In A Chastity Belt And Stockings Has Fun With His Anus Fucks Himself With An Artificial Dick

2 years ago

ShemaleZ

fisting, chastity
09:17

Sissy chastity training with big black dildo

2 years ago

xHamster

train, chastity
08:14

Erika Oak Cums In Chastity From Her Vibrator

3 years ago

xHamster

vibrator, chastity
06:29

Sissy's small chastity cage gets anal workout with BBC

2 years ago

xHamster

chastity
34:31

Ts Mistresss Seduces Mature Muscle Slave & Cums In His Mouth

3 years ago

ShemaleZ

mature, latex, muscle, cum in mouth, seduced, chastity
24:57

Chastity sandy loves black cocks

5 years ago

TXXX

blonde, bareback, chastity, black
04:03

Hot Sissy In Chastity Strapon Fucked By Dominatrix

1 year ago

ShemaleZ

strapon, chastity
14:25

Double time again

2 years ago

xHamster

dildo, double anal, finnish, first time, chastity
03:23

Sisk On Pink Thong And Chastity Cage Release

2 years ago

ShemaleZ

chastity
05:15 78%

German trans girl cums while being locked up in chastity by her jealous boyfriend - solo masturbation - Emily Adaire TS

3 years ago

xHamster

german, chastity, homemade
16:39

Trans Girl In Chastity Plays With Dildos And Fists Herself

3 years ago

ShemaleZ

fisting, chastity
09:41

Sexy bitch in chastity shopping in milano

8 years ago

xHamster

outdoor, chastity
08:44 75%

Dominatrix Fucks Hot Crossdresser In Chastity

1 year ago

ShemaleZ

BDSM, crossdresser, chastity
12:28

Caged Sissy pussy fucking machine in chastity

2 years ago

xHamster

german, chastity
21:19

Twin Game

1 year ago

xHamster

handjob, crossdresser, compilation, chastity
02:48

The Meaning of Life - Diamond Chastity

10 years ago

xHamster

gangbang, chastity
06:12

Walking in chastity cage and buttplug

5 years ago

HClips

outdoor, chastity
04:48

TV Gloria in chastity dildo riding

6 years ago

ShemaleZ

riding, chastity
09:02

Gudrun And Angie In Chastity And Pump Plug Games

2 years ago

HClips

mature, stockings, lingerie, chastity
02:06

Sissy Lucy gets Pegged in Chastity whilst trying to wash up

4 years ago

xHamster

mature anal, pegging, chastity
05:10

Trans Woman in Chastity Fucked Missionary POV

2 years ago

xHamster

BDSM, missionary, chastity
05:34

Slutty Sissy Pirate Cage Dance by Sissy Mindy

1 year ago

xHamster

solo, crossdresser, chastity, sissy
04:59

Sukey Wearing Chastity Belt 2

2 years ago

ShemaleZ

chastity
06:07

Chastity Belt Butt Plug Trainer

6 years ago

ShemaleZ

chastity
05:53

Lily Leigh Cam Show - November 21st, 2023 - Chastity Cage & Dildo Private Show

1 year ago

xHamster

amateur, small cock, dildo, chastity
09:09

Chastity Sandy Fucked Hard

5 years ago

xHamster

vintage, chastity
10:31

Multiple Anal Sissy Orgasms in Chastity Cage & Then Unlocked Massive Cumshot Jessica Bloom

3 years ago

xHamster

orgasm, chastity
06:15

Redhead sissy in chastity riding BBC dildo

6 years ago

ShemaleZ

crossdresser, BBC, sissy, chastity
20:28

Anal Training in Chastity

6 years ago

ShemaleZ

train, teen anal (18+), chastity
16:04

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

2 years ago

ShemaleZ

dildo, redhead, tattoo, chastity
09:39

Fucking Machine Anal Orgasms Chastity Foot Slut Jessica Bloom 10 Min

5 months ago

HClips

feet, POV, orgasm, machine, slut, anal orgasm, chastity
07:16

PorchaeTS chastity Pissgasm from huge anal dildos

1 year ago

xHamster

pissing, huge dildo, hands free, chastity
05:42

Good anal cumshots without hands vladasexytrans

1 year ago

xHamster

chastity, sissy, cumshot, amateur, crossdresser
04:15

Ts Kelsey Masters Fucked Raw In Chastity

2 years ago

ShemaleZ

chastity
04:38

Posting my chastity key goes wrong

1 year ago

xHamster

outdoor, lingerie, british, sissy, chastity
03:37

Sissy in chastity sucking cock

8 years ago

ShemaleZ

POV, chastity
03:44

Latex Rubberdoll Ruined Orgasm In Chastity

3 years ago

HClips

latex, orgasm, chastity
03:01

Fucking Machine And Chastity (cum At 1:30)

2 years ago

ShemaleZ

machine, chastity
04:36

Crystal Paige playing solo

2 years ago

xHamster

mature anal, heels, chastity
05:45

Amateur Femboy Tries To Cum Handsfree In Chastity But Gets Impatient And Jerks Off

3 years ago

ShemaleZ

hands free, chastity
10:18

Chastity Sissy Anal Orgasms And Licking Cum Of Feet Jessica Bloom And Femdom Polieana

1 year ago

TXXX

feet, femdom, POV, orgasm, sissy, anal orgasm, chastity
21:51

Teen tranny fuck her ass with big dildo

1 year ago

xHamster

dildo, chastity, femboy, sissy
07:41

Chastity life

6 years ago

TXXX

BDSM, chastity
18:48

Trap In Chastity Cage Anal

4 years ago

ShemaleZ

blonde, chastity
06:10

Chastity Slut In Stockings And Heels Playing With Suggest Model

4 years ago

ShemaleZ

heels, chastity, mature
04:12

Sissy Anal Adventures - He Has To Hold His Cum In Chastity While I Stretch His Ass With Giant Dildo

3 years ago

HClips

chastity, cum in ass, cum while fucked
01:30

Sisk Unlock Her Chastity Cage and Play with Her Clitty Dick

1 year ago

xHamster

bathroom, chastity
06:48

Anal Slut Chained to the Fuck Machine by Her Balls

1 year ago

xHamster

small cock, bondage, dildo, chastity, femboy
10:20

Sissy Anal Training And Sissygasm In Chastity Sc.7

2 years ago

ShemaleZ

train, sissy, chastity
09:13

Sissy In Chastity arse pokeed

7 years ago

ShemaleZ

fetish, chastity
02:28

Transgender in Chastity Fucked Doggystyle

2 years ago

xHamster

BDSM, dogging, sissy, chastity
11:23

Real sissy in chastity outdoor

10 years ago

xHamster

outdoor, chastity
04:06

Cute Sissy Cums in Her Own Mouth in Chastity

3 years ago

xHamster

cum in mouth, chastity
09:37

Starla Releases Randy From Chastity

7 years ago

ShemaleZ

chastity
04:26

Cute Femboy In Chastity Cage Masturbate With Vibrator

2 years ago

HClips

vibrator, chastity
14:11 67%

Its Okay To Want To Fuck Trannies (part 1) Transgender Encouragement Seduction Tgirl Feet & Ass

2 years ago

ShemaleZ

feet, latex, seduced, chastity
07:32

Young Sissy Casting Sissy Fucked Hard In Chastity Fisting Sissy Maker Sissy Story Extreme Pegging

4 years ago

ShemaleZ

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07:41

Full fashion seamed stocking chastity girl

9 years ago

TXXX

chastity
06:22

Sissy chastity training on tentacle

3 years ago

xHamster

train, dildo, tentacle, chastity
06:55

How a Sissy should Masturbate - Sissy - Crossdresser slut - Chastity with Vibrator - Sissy Joanna

1 year ago

xHamster

chastity
1:00:38

Master fucking and fisting my ass with machine

2 years ago

xHamster

fisting, BDSM, machine, chastity
22:14

Fuck me in chastity device

7 years ago

ShemaleZ

latex, chastity
04:42

Sissy slut dressed in lingerie locked in chastity and playing with a big glass anal plug

2 years ago

xHamster

public, glasses, dress, chastity
08:50

Femboy In Chastity Cage Plays With His Bad Dragon Nova. Cums From Vibrator And Fuck Machine

3 years ago

TXXX

toys, machine, vibrator, chastity
05:39

Booty sissy in chastity plays with a vibrator

2 years ago

xHamster

vibrator, chastity
18:39

Spiked Chastity Cage Torment - Sissy Maids Self Bondage

2 years ago

xHamster

bondage, maid, BDSM, chastity
04:15 80%

Vlada Russian of tranny maid Fucks herself in the ass with a chastity belt

6 years ago

ShemaleZ

russian, maid, chastity
07:36

Chastity desire, Gudrun and Angie

5 years ago

xHamster

mature, mature anal, chastity

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