SHEMALE • CHASTITY 516 videos

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15:30

Glass Shower Door Dildo Fuck by Sissy Mindy

3 days ago

xHamster

crossdresser, sissy
33:32

Skyler Storm Anal Masturbation in Chastity

3 days ago

PornHub

amateur
29:22

Imagining Im a Femboy make me Spreading Anal Invasion again

1 week ago

TrannyGem

cute, teen (18+), fetish, teen anal (18+), dildo, masturbation, toys
16:59

Sissy Femboy uses vibro to taunt encaged fuck-stick

2 weeks ago

TrannyGem

chastity
15:34

Transsexual Lucy hace rectal y sissygasm para showcase web cam hardcore

2 weeks ago

TrannyGem

crossdresser
15:39

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2 weeks ago

TrannyGem

feet, hands free
15:39

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2 weeks ago

PornHub

solo, sissy, chastity
34:23

Trans Latex Hands Free Cum, Chastity Fuck, Piss Drinkung

3 weeks ago

PornHub

pissing, shemale, fetish, solo, chastity
33:44

Trans Latex Hands Free Cum, Piss Drinking, Chastity Fuck, XXXSamanthaPhD

3 weeks ago

PornHub

chastity
18:59

Plastic ladyboy whore in chastity rides yam-sized fuck sticks

3 weeks ago

ShemaleMovie

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16:10

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

1 month ago

TrannyGem

chastity, cum in ass
25:04

Sissy Maid Collared to Bedpost in Spiked Chastity Cage and Handcuffed Harness Gagged

1 month ago

xHamster

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27:08

Chastity bottoms

1 month ago

AShemaleTube

cumshot, chastity
24:34

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1 month ago

TrannyGem

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19:03

Sexy TS Kitty Lucia Maya LEAKS CUM in Chastity While FUCKING HER ASS Then Unlocks Cage & CUMS HARD

1 month ago

xHamster

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32:31

Cute Trap In Chastity Get A BBC Creampie

1 month ago

BeMyHole

stockings, creampie, anal, ass licking, BBC, chastity
18:58 86%

Sexy TS kitty Lucia Maya LEAKS CUM in chastity while she FUCKS HER ASS then CUMS HARD

1 month ago

AShemaleTube

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30:39

Femboy chastity dildo riding!!

1 month ago

PornHub

chastity
15:29 97%

Shemale Suzie XXL and Girl fuck and pegging a black slave in chastity cage

1 month ago

KeekAss

black, latex, shemale, threesome, fetish, domination, pegging
32:11

Lizzy Yum, August 2022 No. 8, SEX MACHINES, EROTIC ELECTRICITY AND BDSM chastity

1 month ago

JizzBunker

mature anal, gagging, erotic, machine, chastity
15:52

Exposed Sissy Bitch Tiffany Minx – Blowjob In Chastity - “Confide In Me” by Kylie Minogue

1 month ago

AShemaleTube

crossdresser, cum in mouth, sissy, chastity, femboy
18:11

@sissy.allison OF Sissy Femboy Chastity Cage and Butt Plugs

1 month ago

PornHub

fetish, bondage, chastity
16:12

Crossdresser sissy tranny ass fucked pig slut chastity

1 month ago

XXXDan

orgasm, bondage, BDSM, nipples, cosplay, chastity
16:11

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

1 month ago

xHamster

riding, mexican, chastity
16:37

Guy Jerks Off With Trans Woman In Chastity 17 Min With Kelsey Masters

1 month ago

ShemaleZ

chastity
32:31 96%

Sabina Steele Aj Fresh Chastity Angel Anal Creampie Bbc Dgs

2 months ago

BeMyHole

stockings, black, blowjob, creampie, anal, interracial, ass licking
21:30

Sissy fists her ass hard in chastity

2 months ago

XXXDan

mature, mature anal, fisting, chastity, webcam
16:05

Chastity Orgasm by Sissy Mindy

2 months ago

xHamster

chastity
16:31

Sissy Chastity Cage and Dildo

2 months ago

PornHub

chastity
45:35

Listening to hypno training my sissy pussy in chastity like a good slut. Spit roast

2 months ago

AShemaleTube

chastity
18:49

Plastic shemale slut in chastity rides huge dildos

2 months ago

XXXDan

strapon, huge dildo, orgasm, chastity
29:14

Shemale Sub In Chastity Takes Bbc And Gets Cum Filled

2 months ago

ShemaleZ

amateur, shemale, interracial, lingerie, bareback, BBC, chastity
19:19

Transfixed Sissy Instructing to Bambi TikToks PMV

2 months ago

TrannyGem

shemale, crossdresser, chastity
17:08

Caged Sissy Slut Rides BBC Dildo Sex Toy

3 months ago

xHamster

dildo, BBC, chastity
24:04

Lizz_ss25 changed sissy play

3 months ago

xHamster

chastity
20:22 89%

Chastity TS Vs BBC

3 months ago

BeMyHole

black, shemale, interracial, glasses, BBC, chastity
29:14

Tiffany Doll - Sissy Schoolgirl In Chastity Bred Wit

3 months ago

ShemaleZ

interracial, sissy, chastity
24:34

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

3 months ago

TrannyGem

feet, dildo, chastity
18:21

Plumbing machine vs fledgling T-woman in chastity for Andy

3 months ago

ShemaleMovie

machine, chastity
25:26

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

3 months ago

ShemaleZ

POV, ladyboy, shemale and girl, cum in mouth, chastity, femboy
21:51

Teen tranny fuck her ass with big dildo

3 months ago

xHamster

dildo, chastity
15:20

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

3 months ago

xHamster

stockings, thai, masturbation, skirt, chastity, femboy
20:06

Erika Oak Pumps Her Asshole

3 months ago

xHamster

dildo, chastity
31:16 67%

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

3 months ago

ShemaleTaxi

anal, crossdresser, cumshot, sissy, chastity, femboy
29:34

Sissy Maid in Armbinder and Ankle Cuffed to bed in Chastity

4 months ago

xHamster

pantyhose, maid, chastity
35:21

Lizz_ss25 Slut vision anal steam

4 months ago

xHamster

chastity
32:38

Sissy Maid in Spiked Chastity Cage Cuffed to Bed Post

4 months ago

xHamster

maid, chastity
20:27

CD rides big black cock wearing rosy chastity

4 months ago

ShemaleTaxi

british, toys, BBC, chastity
19:08 75%

Chastity Shemale Takes Interracial Anal Reaming And Creampie

4 months ago

ShemaleZ

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16:51

Cute pink haired trans woman Angel Tears masturbating in chastity

4 months ago

AShemaleTube

homemade, chastity
15:03

Trap In Permanent Chastity And Extremely Aroused - Video 001

4 months ago

Upornia

chastity
18:37

V-Card box switch suprize oral pleasure!

4 months ago

TrannyGem

cuckold, chastity, femboy
16:35

Trap in permanent innocence and utterly exhilarated - flick 002

5 months ago

TrannyGem

chastity
20:03

Crossdressing Model Deep Anal Play First Sissygasm Sissy Chastity

5 months ago

ShemaleZ

teen anal (18+), BDSM, chastity
20:32

Trans ash-blonde took her friends chastity

5 months ago

ShemaleTaxi

lingerie, shemale fucks guy, chastity
17:28

Sexy TS Lucia Maya in Chastity fucks her ass & LEAKS CUM before BLOWING HER LOAD

5 months ago

xHamster

cumshot, hands free, chastity, cum in ass
17:23

Sexy TS Lucia Maya in Chastity fucks her ass & LEAKS CUM before BLOWING HER LOAD

5 months ago

AShemaleTube

chastity, cum in ass
20:51

Sissy in chastity pounds pussy hard until she makes cummies

5 months ago

PornHub

teen (18+), BDSM, 18, chastity
16:23 90%

Cuties cumming in chastity: a compilation

5 months ago

AShemaleTube

compilation, cumshot compilation, sissy, chastity, femboy
25:22

Sissy slut in chastity takes it in the ass in numerous postures like a supreme trans cuck femboy slave should!

6 months ago

ShemaleTaxi

chastity
20:03

Notsoftforwork chastity cage and vibrator

6 months ago

JizzBunker

vibrator, chastity
15:03

She-Creature plows her slot in the crimson rays

6 months ago

TrannyGem

chastity
26:40

Chastity Caged No Hand Cum Compilation

6 months ago

ShemaleZ

stockings, BDSM, compilation, selfsuck, hands free, chastity
17:29

Multitude Itsol bjs her toes and taunts her lil salami with wand

6 months ago

TrannyGem

feet, cute, small cock, orgasm, masturbation, vibrator, chastity
30:22

Sissy hole trainer ambersis every sissy must watch

6 months ago

PornHub

femdom, chastity
1:08:51

Sissy slut in lingerie anal fuck on sex machine with squirting in chastity cage! Good little femboy beta cuck slave!

6 months ago

xHamster

pissing, squirt, crossdresser, chastity
18:35 88%

Chastity OFF penalized IN stiff FUCK

7 months ago

ShemaleMovie

shemale, anal, maid, bareback, chastity
15:54

Crossdresser On Live Webcam - Sissy Wears Chastity Belt

7 months ago

ShemaleZ

crossdresser, blonde, sissy, chastity
18:39

Spiked Chastity Cage Torment - Sissy Maids Self Bondage

7 months ago

xHamster

bondage, maid, BDSM, chastity
21:51

Self Suspension Bondage - Sissy Maid

7 months ago

xHamster

latex, bondage, maid, chastity
1:08:02

Chastity Transfiguration

8 months ago

XXXDan

femdom, lesbian, masturbation, chastity
1:08:50

Real fledgling homemade sissy cuck penetrates hump machine in chastity cage, feminization squirting femboy!

8 months ago

ShemaleTaxi

squirt, crossdresser, chastity, femboy
24:46

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

8 months ago

ShemaleZ

femdom, BDSM, BBC, chastity, sissy
16:05

Mexican Sissy Maid un chastity Cage

8 months ago

xHamster

maid, mexican, chastity
16:06

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

8 months ago

ShemaleZ

orgasm, BDSM, chastity, post op
33:24 71%

Sissys Wooden Pony Ballet Boot Torment

8 months ago

xHamster

latex, fetish, bondage, boots, lingerie, BDSM, chastity
18:24

Sissy Maids Spiked Chastity Cage Self Bondage in New Boots

8 months ago

xHamster

bondage, boots, maid, JOI, chastity
37:08

Sissy Maid Self Bondage Gas Mask Armbinder in Chastity and Ballet Boots

8 months ago

xHamster

bondage, boots, maid, BDSM, chastity
16:52

CD Female Exhibition Roped on Turntable with Magic Massager

9 months ago

TrannyGem

latex, rubber, bondage, BDSM, tied, old and young (18+), chastity
16:12

Lizzy Yum - Welcome home Lizzy- BDSM female chastity post op pussy masturbation orgasm

9 months ago

xHamster

orgasm, chastity, post op
15:49

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

9 months ago

BeMyHole

orgasm, BDSM, chastity, post op
16:12

Another anal training

9 months ago

xHamster

chastity
21:24

Ilandis in a chastity belt has joy with her pooper using different fucktoys

9 months ago

ShemaleTaxi

chastity
40:21

Handjob Two Asian Guys Fucking A Ladyboy In Chastity In The Ass

9 months ago

BeMyHole

chastity
21:23

Ilandis in a chastity belt has fun with her anus using different toys

9 months ago

xHamster

feet, dildo, chastity
40:19

Chastity Cage On Her Penis Asian Ladyboy Threesome Fucked Hard In The Ass

9 months ago

Upornia

stockings, asian, chastity
17:17

Hardcore BBC Dildo destroys my ass, master has no mercy

10 months ago

xHamster

german, dildo, chastity
27:56

Random strangers abuse my asspussy

10 months ago

xHamster

german, stranger, chastity
18:49

Latex Transgirl In Chastity Spanked, Teased, And Fucked By Femdom

10 months ago

BeMyHole

femdom, latex, spanking, chastity
15:25

In Chastity Cage And Butt Plug

10 months ago

ShemaleZ

chastity
25:11

Hi I'm Linzy19

10 months ago

xHamster

bondage, BDSM, monster, webcam, chastity
27:49

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

10 months ago

ShemaleZ

fisting, secretary, chastity
18:38

Sissy Lucy Being Locked Up In Metal Chastity For Locktober

10 months ago

ShemaleZ

latex, chastity
1:02:09

Sissy Lucy Anal Training In Chastity With Huge Dildos And Getting Pegged By Lisa

10 months ago

ShemaleZ

mature anal, huge dildo, pegging, chastity
21:33

Sissygasm Challenge Day 2 - Femboy In Chastity Riding Dildo

10 months ago

ShemaleZ

chastity
15:53

Sissy Joyce - The Vice Complete Chastity Review & Guide - ALL SIZES

10 months ago

BeMyHole

maid, sissy, chastity
53:38

Batman Cosplay Parody With Bbc Batman Chastity Sissy Batgirl And Latex Hit Girl

10 months ago

ShemaleZ

latex, BBC, cosplay, chastity
17:51

HEAVY EDGING!!! Transgender Princess gets her Uncaged Girlcock milked and jacked!!!!!

10 months ago

TrannyGem

handjob, amateur, mom, homemade, shemale, couple, orgasm
31:05

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

10 months ago

ShemaleZ

dildo, chastity
17:32

LanaTuls - encaged in a chastity and Crossdressed railing a Big Dildo

10 months ago

ShemaleMovie

chastity
19:11

Latex Transgirl in Chastity Spanked, Teased, and Fucked by Femdom - OnlyFans @Ms_Nacke

10 months ago

PornHub

femdom, latex, bondage, spanking, pegging, chastity
22:55

Sissy Secretary in horny after work activities

10 months ago

xHamster

stockings, shemale, clit, secretary, nylon, sissy, chastity
17:12

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

11 months ago

ShemaleZ

clit, chastity
53:05

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

11 months ago

xHamster

orgasm, bondage, chastity, post op
25:50

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

11 months ago

TrannyGem

latex, huge dildo, chastity
25:50

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

11 months ago

xHamster

latex, mature anal, huge dildo, british, chastity
16:11

Sissy attempts restrain bondage :)

11 months ago

TrannyGem

train, bondage, maid, ass, chastity
22:25

Mistress Gives Me Cages Key To Cum As A Woman After 6 Days On Chastity

11 months ago

HClips

femdom, chastity
18:15

PorchaeTS pounds pussy with huge dildos and cums hard.

1 year ago

xHamster

huge dildo, chastity
49:33

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 2

1 year ago

xHamster

french, chastity
17:10

Sissy Maids Self Bondage Predicament

1 year ago

xHamster

latex, fetish, bondage, maid, chastity
15:12

Sissy Maids Spiked Chastity Cage Self Bondage Torment

1 year ago

xHamster

latex, fetish, bondage, maid, chastity
17:11

Guy Jerks Off with Trans Woman in Chastity

1 year ago

xHamster

fetish, 18, jerking, chastity
21:30

Sissy Fisting Ass Hard In Chastity

1 year ago

ShemaleZ

fisting, chastity
23:46

Sissy Hope, the naughty slut & her new cam

1 year ago

xHamster

tattoo, mexican, slut, chastity
22:10

Sissy Maid Hogtied In Armbinder While In Steel Chastity Belt Gagged

1 year ago

Upornia

gagging, maid, chastity
1:03:39

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 1

1 year ago

xHamster

stockings, french, lingerie, chastity
16:32

Sissy In Chastity Getting Her Asshole Whipped Before Getting Anally Barebacked

1 year ago

Upornia

asshole, chastity
17:30

Sissy femboy in chastity riding big toys and spanking herself

1 year ago

xHamster

spanking, dutch, slut, chastity
32:07

Chatty crossdresser tries out new depth - 2023-02-23 - part 2 - uncharted territory

1 year ago

xHamster

french, chastity

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