SHEMALE • CHASTITY 690 videos

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15:25

Hot Updates Compilation 25th To 29th Of May 26

2 days ago

BeMyHole

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18:03 71%

Anticsofanna A Little Students Chastity Sissification With

3 weeks ago

VipTube

chastity, shemale, interracial, student
15:23

Ultra-kinky Sissy Daniella in teach

4 weeks ago

TrannyGem

homemade, public, POV, train, outdoor, dildo, lingerie
25:51 72%

Raw Bareback TS Crossdresser Chastity

1 month ago

JizzBunker

amateur, anal, couple, lingerie, crossdresser, blonde, heels
29:35 82%

Chastity Trans Creampied By BBC

1 month ago

NuVid

BBC, creampie, chastity, shemale, interracial, big cock
25:48 69%

Crossdresser in Chastity Fucked Raw

1 month ago

AShemaleTube

amateur, anal, crossdresser, blonde, sissy, chastity
16:50 83%

Gorgeous TS Babe Akira Rabbit Rides A Huge Dildo in Chastity

1 month ago

AShemaleTube

huge dildo, big ass, dildo, solo, riding, masturbation, chastity
19:11

Sissy Slut Joanna rides a faux-cock while in chastity for Locktober Sissygasm Femboy Crossdresser Shemale

2 months ago

ShemaleMovie

shemale, BDSM, chastity
20:05

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 6

2 months ago

AShemaleTube

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15:32

Chastity Slut Needs Her Ass Used

2 months ago

$$ FapHouse

latex, shemale, chastity, anal, dildo
20:10

Kelsey Masters in Chastity Belt Bareback Pounded Compilation

2 months ago

XXXDan

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16:20

School-damsel crossdresser desperately attempts to cum having a chastity cage (slowmotion replay)

3 months ago

ShemaleMovie

lingerie, chastity, crossdresser
26:13 29%

DustiBunni Evelyns Chastity Training - Update One

3 months ago

NuVid

amateur, shemale, chastity, masturbation, handjob
26:04

Sissy Training Buttplug Play & Massagegun Plapping Cumshot in Chastity!

3 months ago

$$ FapHouse

train, sissy, chastity, cumshot, masturbation
30:06

Chastity Femboy Pounded by Sissy

3 months ago

JizzBunker

lingerie, BDSM, heels, sissy, chastity, femboy
26:37 57%

Trans School Teacher Gets Barebacked By Bf After Letting Him Out Of Chastity

3 months ago

ShemaleZ

bareback, chastity, shemale, amateur, creampie, teacher
36:16 86%

Big Dick Russian Trans In Chastity Demolished

3 months ago

BeMyHole

black, shemale, anal, russian, domination, BBC, hardcore
21:43

Shemale Crossdresser in Chastity Gear Wears Lingerie and Dildo Fucks

3 months ago

JizzBunker

dildo, compilation, handjob compilation, heels, sissy, chastity
21:40

Crossdresser in Chastity Gets Dressed and Dildo Fucked

4 months ago

AShemaleTube

amateur, dildo, crossdresser, compilation, dress, sissy, chastity
16:32 86%

Chastity Cage Shemale

4 months ago

AShemaleTube

anal, POV, chastity, big ass
20:05

Fucking Sexy Sissy in Chastity - Compilation 3

4 months ago

AShemaleTube

blowjob, chastity, sissy, shemale, compilation, big ass
21:53

Lovely chinese shemale maid Mina cums in chastity while railing a huge dildo... Please daddy, make me clean my own mess like a good maid should...

4 months ago

ShemaleTaxi

chinese, chastity, maid
15:09

Mtf 39 chastity toys lots of fun playing with my clit

4 months ago

AShemaleTube

solo, mature, chastity
16:12

Blonde Sissy Bride Rubs Her New Pussy Chastity

4 months ago

$$ FapHouse

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18:31

Chastity Bitch Fucks Her Ass and Rides a Huge Bad Dragon Dildo

4 months ago

$$ FapHouse

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17:31

Reneenicolecd - update #12 - Fat chief and bj trans fucky-fucky female - May 28, 2026

4 months ago

TrannyGem

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16:28 80%

Guts ejaculations cumpilation. Personalsin bevy vol. 157

4 months ago

TrannyGem

dildo, cumshot compilation, chastity, orgasm, anal orgasm
15:38

Blocked in chastity

4 months ago

AShemaleTube

homemade, chastity
15:10

Sissy Maid Playing with Herself with Bondage, Huge Dildos, and Chastity

4 months ago

$$ FapHouse

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15:42 57%

ARYA SANTANA BROUGHT A LIL BOUNTY FOR YOU HERE ON THE CHANNEL! SHE GAVE A BOD JOURNEY AND HAD A GOOD CLIMAX! - UTTER ON CRIMSON - LUANA PRADO

5 months ago

TrannyGem

pissing, amateur, beauty, POV, squirt, tattoo, chastity
26:53

Small Dick Trans Raven in Chastity Cage Cumming a Lot After Humiliating Herself with BBC Dildo

5 months ago

AShemaleTube

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16:13

Student crossdresser desperately tries to cum having a chastity box (cum replay in slow-motion)

5 months ago

ShemaleMovie

orgasm, prostate, chastity
15:45

Molten Blondie Crossdresser Using Wand Trans Chick

5 months ago

TrannyGem

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21:41 60%

Sissy Jessica Bloom Tries Out 5 Different Types of Chastity Cage

5 months ago

AShemaleTube

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19:59

Trans Woman in Chastity Fucked Hard - Compilation 6

5 months ago

AShemaleTube

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20:08 50%

Chastity Cage Trans Girl Kitten Succubus cangue Vibrator culo speculum Gaming Overwatch Streaming Controlled Emo Goth egirl sissy femboy cute

5 months ago

VideoSection

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19:59

Trans Woman in Chastity Fucked Hard - Compilation 1

6 months ago

AShemaleTube

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20:10

Trans Woman in Chastity Fucked Hard - Compilation 10

6 months ago

AShemaleTube

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17:45

Ladyboy anal invasion fuck with huge dildo while cock locked in chastity box and pissing

6 months ago

ShemaleMovie

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19:30 91%

Trans Chastity Princess Takes BBC

6 months ago

AShemaleTube

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28:11

Fucking Mtf Chastity Charlie

6 months ago

$$ FapHouse

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20:08

Schlong gagged trans Catgirl in chastity tries to play overwatch while viewers vibe her plug succubus egirl gamer streamer livestream camgirl 4/4

6 months ago

VideoSection

chastity
19:30 92%

Trans Chastity Princess Takes BBC

6 months ago

AShemaleTube

amateur, anal, interracial, big cock, BBC, chastity
20:29

That huge fucking dildo made me seep from my chastity... And then I came four times in a row, like a good bitch...

7 months ago

ShemaleMovie

cumshot, dildo, huge dildo
16:07

Sissy coming home from work

7 months ago

TrannyGem

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18:25

Chastity Sissy Fucked by Machine Until Sissygasm

7 months ago

AShemaleTube

crossdresser, sissy, shemale, chastity, machine
19:22

Tgirl police officer Lucy with a huge cock degrades her chastity victim during a wild session

7 months ago

XXXVogue

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19:32

Dominant officer Lucy in uniform humiliates her chastity submissive with a big cock

7 months ago

XXXVogue

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43:27

Big Cock Police Officer Lucy Fucking and Humiliating Chastity Sub

7 months ago

$$ FapHouse

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20:00

Trans In Chastity Fucked Raw - Compilation 3

7 months ago

HClips

amateur, shemale, chastity
19:22

Big cock police officer Lucy fucking and humiliating chastity sub

7 months ago

AShemaleTube

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28:43

Hina Kagiyama Cosplay with Chastity Cage Anal Masturbation.

7 months ago

AShemaleTube

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18:00

Renee the SissyDeep Jaws Tramp

7 months ago

TrannyGem

big ass, chastity, gape, toys, food, huge dildo
16:09

TS Goth Breaths In The Sissy Transformation Gas

7 months ago

BeMyHole

sissy, shemale, chastity, femboy, goth
22:16

Put Me On Your Fat Cock, I’m Caged

8 months ago

BeMyHole

fat, facial, bikini, babe, socks, chastity, femboy
24:59

Femboy Ava Chastity and Panties

8 months ago

AShemaleTube

femboy, chastity, shemale, masturbation, solo, sissy
17:19

Anal Fuck While in chastity cage, Anal orgasm of a Sissy Femboy

8 months ago

ShemaleTaxi

thai, orgasm, dildo, taxi, anal orgasm, chastity
30:38 86%

Chastity Fuckdoll (1080).mp4

8 months ago

AShemaleTube

shemale, anal, chastity, blowjob
30:38 93%

Chastity Fuckdoll

8 months ago

AShemaleTube

blowjob, anal, interracial, cumshot, small tits, chastity
20:03

Cute tgirl succubus Kitten in a collar and chastity gets her vibrating butt plug controlled during a live stream

8 months ago

XXXVogue

game, chastity
20:21

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 10

8 months ago

AShemaleTube

amateur, blowjob, compilation, sissy, chastity
20:03

Cute trans catgirl succubus gets toyed with by viewers while in chastity during a Pokémon-themed hentai stream

8 months ago

XXXVogue

chastity
19:01

Sissification Lecture Ultimate Guide to Sissy Orgy Fucktoys Veronica Taboo invites you to Sissy Academy

8 months ago

TrannyGem

orgy, sissy, chastity, hands free
24:14

Female domination milf Lisa bind and Tease with Chastity Dilf Mike Essex

8 months ago

VideoSection

tease, MILF, bondage, BDSM, british, domination, chastity
26:53 88%

Stiletto Sissy slaves first-ever assfuck Stretching with Electrics and Chastity by Mistress Mercer

9 months ago

VideoSection

femdom, bondage, boots, BDSM, sissy, gape, chastity
37:52

CD in pink Corset and chastity, nipple forceps,smacking, sucking, playing and teasing

9 months ago

ShemaleMovie

masturbation, chastity, nipples, tease
20:29

That huge dildo made me leak from my chastity... and then I came multiple times like a total slut

9 months ago

XXXVogue

huge dildo, chastity, dildo
40:45 61%

AJ Fresh Gray Perrier CHASTITY FUCKDOLL5 (1080) - Tranny Videos XXX

9 months ago

TXXX

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20:33

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 5

9 months ago

AShemaleTube

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18:40

Minaasian has back-to-back orgasms while locked in a chastity cage with a thick cock up her ass

9 months ago

XXXVogue

chastity, cumshot
27:22 33%

Sweet Chastity 16

9 months ago

AShemaleTube

shemale, chastity
28:01

POV Trans Femdom, Suck My Dick While in Chastity You Sissy Slut!

9 months ago

$$ FapHouse

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49:21 90%

Big black cock takes on tgirl in chastity

9 months ago

XXXVogue

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24:46 57%

Chastity Sissy Gets tights Torn and Pegged by Bad Dragon Strapon by mistress Mercer

9 months ago

ShemaleMovie

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22:13

Sweet Chastity 14

9 months ago

AShemaleTube

chastity
48:11

Sweet Chastity 8

9 months ago

AShemaleTube

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22:08

Sweet Chastity 12

10 months ago

AShemaleTube

chastity
31:42 81%

Lingerie Sissy Gets Locked Onto Her Dildo Pole and Tries to Cum in Chastity

10 months ago

$$ FapHouse

bondage, dildo, masturbation, heels, sissy, chastity
32:27

Stepdaddies Little Chastity Slut - Fucking Machine Cumshot

10 months ago

$$ FapHouse

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18:00

Sweet Chastity 5

10 months ago

AShemaleTube

shemale, chastity
22:55

Cute asian shemale Mina cums in chastity while riding a huge fake penis

10 months ago

ShemaleMovie

chastity, riding, asian
16:53

Daniela Lei chastity caged on fuck machine

10 months ago

TrannyGem

boots, italian, chastity
26:51

Full: Big Balls Sissy in Chastity Cage Massive Cumshot and Masturbating Her Small Dick Like a Girl

10 months ago

$$ FapHouse

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21:22

Ilandis in a purity belt has joy with her ass-hole using different playthings

10 months ago

TrannyGem

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21:47

Shemale maid Mina cums in chastity while railing a immense dildo... Make me clean my own mess parent!

10 months ago

VideoSection

shemale, dildo, chastity
22:38

Crimson Spandex girl Assfuck Have Fun Fuck Sticks, Butt-Plugs, Mayo, Coffee

10 months ago

TrannyGem

latex, doll, chastity, rubber
26:42

Transgender college instructor enjoys bareback fun with her boyfriend after freeing him from chastity

10 months ago

XXXVogue

anal, creampie, amateur, chastity, beauty, shemale
31:00

Unboxing of Gifts: Chastity Cage, Huge Buttplug and More

10 months ago

$$ FapHouse

chastity, amateur, big tits
16:34

Anal plug, chastity cage, and a vibrator... the ultimate trio for a submissive whos all about those orgasms in chastity

10 months ago

XXXVogue

chastity, vibrator
26:56 92%

Sissy Femboy In Chastity Cage Fucked

10 months ago

AShemaleTube

sissy, shemale, femboy, homemade, amateur, chastity
22:30 57%

Mistress Mercer gives her sissy chastity slave a disciplinary tease and CBT session

10 months ago

XXXVogue

domination, shemale, BDSM, sissy, chastity, femdom
21:20 73%

Sissy slut Takes My new meaty Ridged Dildo Haul in Chastity by Mistress Mercer

10 months ago

ShemaleMovie

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16:11

Sissy in a innocence cell drills herself with a plow machine after the beach

10 months ago

TrannyGem

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15:40 83%

Riding big fat dildos in chastity!

10 months ago

NuVid

shemale, dildo, solo, chastity, fat
16:15 63%

Commands on using a iron plane chastity for sissys

10 months ago

ShemaleMovie

shemale, chastity, sissy
22:49

Mi Ama me da la llave de la jaula y me corro como mujer usando un vibrador

10 months ago

TrannyGem

crossdresser, femboy
15:37

Using my gfs massager while railing my large butt-plug

10 months ago

TrannyGem

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19:15

Lazzy luvs a quiet night with her bad dragon faux-cock

11 months ago

TrannyGem

anal, solo, chastity
22:42

Princess Sahara Taunting & Outrageous Her Trans Hoe

11 months ago

TrannyGem

feet, femdom, fetish, BDSM, tattoo, heels, chastity
15:40

Spunk-Pump Tamer lets their lil pink cigar out and it gets taller into a rock rock hard, vein adorned, pulsating dinky!

11 months ago

TrannyGem

cumshot, masturbation, shemale, chastity, pump, goth
27:35

Crimson Rubberdoll Ass-Fuck Plumb with Fucktoys Thrusting & Farting Out Flogged Mayo to slurp & swallow

11 months ago

TrannyGem

pissing, farting, latex, rubber, doll, fetish, dildo
30:30 67%

Libération Après 1 Mois De Cage

11 months ago

BeMyHole

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19:12

Trap in v-card box assfucking

11 months ago

TrannyGem

cute, dildo, crossdresser, blonde, skinny, chastity
15:39

Sissy April Diamond Daily humping day two

11 months ago

TrannyGem

hardcore, chastity, dildo
24:41

Virginity and permission to spunk

11 months ago

TrannyGem

amateur, BDSM, chastity, bondage
28:17

Using My Chastity Cage and Belly Bulge with My Huge Toys

11 months ago

$$ FapHouse

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17:45 81%

Locked Trap vs Large Fuck Stick - Sissy Trap

11 months ago

TrannyGem

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19:11 91%

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11 months ago

ShemaleTaxi

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20:59 59%

White Sissy Virginity Instructing (Smash Machine)

11 months ago

TrannyGem

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29:51 56%

30 mins no break fellate spitroast contest!

11 months ago

TrannyGem

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21:43 89%

Nyxi Gets Anal From Tranny While Locked In Chastity

12 months ago

BeMyHole

missionary, shemale, chastity, domination, ass licking
19:19

Sissy Marcellas gets filled with faux cocks in a pop-shot chastity scene

1 year ago

XXXVogue

anal, fisting, sissy, chastity, dildo
19:14

Sandy-Haired Sissy Fellates Fake Penis and Self-Facial Cumshot on Web Cam

1 year ago

TrannyGem

18, femboy, chastity
15:50 68%

Sissy at Gloryhole Gets Asshole Licked by Stranger

1 year ago

TrannyGem

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24:10

Full Version of My First Time Using a Chastity Cage for My Trans Big Penis

1 year ago

$$ FapHouse

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36:36 94%

Blackate - Russian Trans In Chastity Demolished And Bred By Bbc

1 year ago

ShemaleZ

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18:07

Sissy taunting her encaged clitty till she fails NNN

1 year ago

TrannyGem

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15:25

Lovely sissy in rosy maid sundress plays and pops on 50 cm butplug in v-card

1 year ago

TrannyGem

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22:21

Put Me On Your Fat Cock, I’m Caged Indoors

1 year ago

BeMyHole

fat, femboy, sissy, amateur, bikini, chastity
1:08:53 40%

Sissy slut in lingerie ass-tear up fuck on sex machine with squirting in chastity cage! Good little femboy beta cuck gimp!

1 year ago

ShemaleMovie

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