SHEMALE • CHASTITY 3,849 videos

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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
10:48 47%

Real sissy in in natures garb beach in chastity and rosebud

9 years ago

TXXX

beach, outdoor, natural, chastity
08:50 46%

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

6 months ago

xHamster

small cock, public, solo, cum in mouth, skinny, chastity
05:07 46%

Shemale slave in chastity butt sex fingered

4 years ago

Analdin

fetish, hardcore, chastity
07:26 44%

Sissy clitty chastity

4 years ago

xHamster

sissy, chastity
12:17 42%

Sissy Woman Risky Assfuck Getting Off in Pubilc Rest Room with trio Fake Penises

8 months ago

TrannyGem

toilet, pissing, amateur, public, shemale, fetish, dildo
07:58 42%

Cute Femboy In Chastity Ride My Big Cock

8 months ago

TXXX

amateur, cute, teen (18+), fetish, riding, chastity, femboy
1:11:56 42%

Mistresse LYCIA CHASTITY INFERNO - TRIBUTE

6 years ago

ShemaleZ

femdom, chastity
18:50 41%

Sissy Long Term Chastity

6 years ago

xHamster

POV, sissy, chastity, shemale fucks guy
20:23 39%

A sissygasm through chastity

5 years ago

ShemaleZ

small cock, BDSM, toys, chastity, interracial
05:57 33%

Plugged Sissy in a Swimsuit Frolicking with a Steel Innocence and Petting Rump

4 years ago

TrannyGem

bikini, swimsuit, chastity
10:24 31%

Sissy Chastity Trainer

1 year ago

AShemaleTube

small cock, sissy, chastity, crossdresser
03:04 27%

Russian Domina vs Sissy Chastity Bitch (Brat Perversions)

4 months ago

SomePorn

russian, chastity, sissy
08:08 25%

Sissygasms Ballbusting Chastity PMV

1 year ago

JizzBunker

femdom, compilation, chastity
25:11 23%

Hi I'm Linzy19

1 year ago

xHamster

bondage, BDSM, monster, webcam, chastity
26:38 21%

SISSY IN HIGH HIGH-HEELED SLIPPERS XXL STRAP ON DILDO IN THE BOOTY Pegging Extraordinary Ass Fucking Opening Up FEMALE DOM RUMP GOING KNUCKLE DEEP

3 years ago

TrannyGem

heels, strapon
35:21 18%

Pink chastity

5 months ago

xHamster

chastity
01:04 14%

Femboy in flat chastity cums with a vibrator like a bitch

1 year ago

xHamster

small cock, prostate, hands free, chastity, femboy, asian
03:16

Trans Chastity Slut Dusti Bunni Gets Leashed & Used By Stud

1 week ago

AShemaleTube

slut, interracial, chastity, big cock
12:23

Chastity locked sissy squirting on a dildo while thinking about her daddy

3 months ago

xHamster

pissing, stockings, prostate, dildo, solo, sissy, chastity
2:00:13

Black Tranny Jizz Jam (Full Movie)

4 months ago

xHamster

shemale, black, big cock, full movie, blowjob, chastity
05:50

Sissy Slut Milked In Chastity

1 year ago

GetTranny

chastity, small cock, milk
13:33

Super Flat Chastity Sissy Anal Dildo Squirt

1 month ago

HClips

shemale, squirt, dildo, solo, sissy, chastity
21:26

Trim my head and converse about sexperiences, from losing chastity to first micropenis delusion. ITA.

2 months ago

ShemaleMovie

small cock, chastity
13:07

Sissy Tgirl in Chastity teaches wannabe sluts how to take dick with her big strap-on! Full V

2 months ago

AShemaleTube

amateur, shemale, strapon, fetish, solo, crossdresser, domination
07:18

Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum

7 months ago

AShemaleTube

homemade, swallow, machine, sissy, hands free, chastity, femboy
20:49

Spandex Sissy Punished by V-Card Fuckmachine Smacking Dickblowing Pegging by Domina Mercer

3 years ago

TrannyGem

femdom, latex, strapon, bisexual, train, bondage, spandex
05:12

MaureenNadh - Tied Up Dildo Riding, Locked In Micro Chastity

9 months ago

xHamster

dildo, tied, skinny, chastity, riding
11:12

Bitch Moaning on Chair with Chastity Device on

4 days ago

XXXDan

solo, crossdresser, chastity, japanese
25:10

Black Tranny spunk insert - episode 1

3 months ago

ShemaleMovie

ladyboy, shemale, big cock, chastity, black, blowjob
1:06:32

Naughty blonde trap removes chastity & cums

4 months ago

AShemaleTube

chastity, shemale
08:00

Sissygasm In Chastity For A Fucked Crossdressed Slave. Spanking Session With Mistress

2 years ago

GetTranny

femdom, bondage, chastity, crossdresser
08:52

Luxia_tv, submissive and with the chastity cage

5 months ago

xHamster

mature anal, spanish, crossdresser, sissy, chastity
05:02

TRANSSEXUAL W I L L O W - Lady Penis Encaged & Cum-Shot

7 months ago

TrannyGem

amateur, creampie, solo, cumshot, big cock, small tits, BBC
08:17

SisK CD in purple EP3 her sissy clity is released from a super tiny chastity cage

2 years ago

xHamster

pantyhose, ladyboy, chastity, asian
12:26

ManyVids Veggiebabyy Feminization Chastity And Thick Cock

1 month ago

NuVid

shemale, chastity
04:01

Cute Trans Fucks Caged Tgirl

6 months ago

PornGem

bareback, shemale, chastity, cute, small tits, small cock
19:32

Horny t-girl amazing sex video

6 months ago

XoZilla

femdom, small cock, shemale and girl, cumshot, small tits, sissy, chastity
07:54

Sissy Holy - chastity getting off directives - how I play with myself

2 months ago

ShemaleTaxi

pantyhose, POV, lingerie, BDSM, ladyboy, solo, british
17:23

Cute sissy shows off her collection of chastity cages

3 months ago

MyLust

chastity, sissy, cute, solo
17:37

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

4 months ago

TrannyGem

shemale, sissy, amateur, chastity
07:18

Cute Crossdresser Leopard Dress and Red Heels

6 months ago

xHamster

big ass, lingerie, crossdresser, heels, dress, chastity
20:48

A Sissygasm through Chastity

5 years ago

TrannyGem

orgasm, bondage, BDSM, BBC, chastity
01:59

Sissy in chastity fucked by BBC

6 years ago

xHamster

chastity
10:32

HUMILIATION DOMINATRIX MISTRESS WORSHIP - with busty blonde Angel Wicky

5 months ago

xTits

big ass, creampie, chastity, femdom, domination
13:01

Female Dominance hand-job for my sissy crossdresser

2 years ago

TrannyGem

femdom, bondage, chastity
08:21

Rosy Sissy Locking her Lil Will-Less Clitty in the Tiniest Innocence Cell

3 years ago

TrannyGem

chastity
15:51

Sissy Female Dominance Compilation - Tusspuss

3 years ago

TrannyGem

femdom, strapon, facesitting, swedish, handjob compilation, domination, pegging
06:30

Ive to work to get my chastity belt off

4 days ago

ShemaleTaxi

facesitting, chastity
15:43

TRANSFIXED - Submissive With Chastity box Erica cherry Makes female dom Queenie Sateen SQUIRT A LOT

2 months ago

ShemaleTaxi

bareback, shemale and girl, chastity, shemale, squirt
23:17

Painful ponyplay on the Halloween party

4 years ago

xHamster

femdom, train, party, russian, BDSM, small tits, hardcore
13:48

Sissy Candy Plays and Fucks Several of Her Dildos While Locked in Chastity

1 week ago

xHamster

amateur, sissy, crossdresser, small cock, chastity, fetish
09:09

German sissy in chastity fucked by daddy

5 months ago

TrannyOne

sissy, chastity, german
11:47

2 sissy latex nurses getting pegged in Chastity by MILF Lisa

11 months ago

xHamster

latex, nurse, shemale and girl, chastity
17:19

Public humiliation locked, plugged, gagged, clamped and squirt

7 months ago

xHamster

outdoor, chastity, BDSM, sissy, public, fetish
06:37

Sexy Blonde Femboy in Chastity - Bailey Wilde Photoshoot

5 months ago

xHamster

anal, chastity, amateur, femboy
20:35

White Sissy Chastity Training (fuck Machine)

1 year ago

ShemaleZ

train, BDSM, machine, sissy, chastity, solo
12:24

Slutty Trans Bunny Lilith Eclipse Fucks Herself With Carrots In Chastity Ass To Mouth

2 years ago

xHamster

fisting, cum in mouth, sissy, chastity
10:15

Transexual Stunner in Chastity

4 years ago

IcePorn

solo, chastity
06:23

Im So Close! She Doesnt Even Realise Shes Jism

6 months ago

TrannyGem

squirt, sissy, chastity, prostate, hands free, machine
04:46

She Gets Continuously Romped To An Explosive Ejaculation

2 years ago

TrannyGem

squirt, machine, anal orgasm, hands free, chastity, dildo
10:11

Cute Trap Solo In Small Pink Chastity

4 months ago

AShemaleTube

amateur, cute, homemade, small cock, solo, masturbation, webcam
04:57

Sissys in Chastity (PMV)

4 years ago

BeMyHole

chastity
06:27

Machine Porked Till She Pops In Her Underpants 4K

2 months ago

TrannyGem

pantyhose, prostate, cumshot, panties, machine, anal orgasm, hands free
10:32

Fetish femdom lesbian sex in office with busty blonde lesbian boss

5 months ago

xTits

black, femdom, shemale, blowjob, creampie, lesbian, fetish
06:14

Average manga porn paramour in virginity box

2 years ago

TrannyGem

feet, russian, cosplay, chastity, solo
09:43

Together in a life of chastity

4 months ago

AShemaleTube

big tits, chastity, domination
04:26

Trans Woman Anal Fucks Femboy In Chastity

1 year ago

ShemaleZ

amateur, chastity, femboy, shemale and girl
05:17

Sissy Strap-on Spitroast In Chastity Pegged By Sexy Femdom Duo By Mistress Mercer

1 year ago

ShemaleZ

femdom, strapon, fetish, BDSM, shemale and girl, pegging, sissy
06:19

Sissy In Chastity Sucking Shemale Cock

1 year ago

GetTranny

chastity
07:44

Beautiful thick blonde changes into her maid outfit and locks herself in chastity

5 years ago

AnyPorn

maid, chastity
06:47

Sissy Locked in Chastity CasualKaylee Fucks her Creamy Ass with Dildo

5 years ago

TrannyGem

dildo, sissy, chastity
02:08

Which size will make me jism?

2 months ago

TrannyGem

orgasm, dildo, redhead, cumshot, BBC, sissy, anal orgasm
03:21

Dominatrix encouraged her sissy pig to cock and ball torture emasculation dog collar its nut sack angel Scarlett black

4 months ago

TrannyGem

dogging, crossdresser, chastity, bondage
04:26

Unmasking - Miss Eva Mae - Girl Masker & Living Female

6 months ago

TrannyGem

shemale, crossdresser, chastity, rubber
09:32

Urinating compilation plane purity cell.

1 year ago

TrannyGem

pissing, femdom, compilation, shy, chastity
05:06

Sissy drinking cum

1 year ago

xHamster

chastity
09:34

Being put into a plane box After Misstress cleans my locked Clitty Little cock

1 year ago

TrannyGem

femdom, skirt, chastity
11:15

*Trailer* Sissy Instructing Basics With Kelli Frost

2 years ago

TrannyGem

train, instruction, chastity
08:00

Chastity Sub Sprays Ruined Orgasm Everywhere

3 months ago

GetTranny

amateur, chastity, feet, shemale, orgasm
06:08

Trio weeks of chastity is only the kicking off

8 months ago

ShemaleTaxi

taxi, chastity
06:15

Bound blue Balls and Chastity forced to cum hands free.

1 year ago

xHamster

BDSM, swallow, chastity, hands free
11:07

Ilandis in a chastity belt has fun with her anus, masturbates with an artificial penis

1 year ago

xHamster

beauty, russian, dildo, penis, asshole, chastity
21:40

Sissy fisting Ass rigid in chastity

2 years ago

ShemaleTaxi

anal, fisting, toys, chastity, femboy, crossdresser
16:07

Mike Ass Fucks Sissy Charlotte While She is Locked in EStim Chastity Cage

2 years ago

xHamster

mature, mature anal, anal, couple, monster, small tits, sissy
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
09:48

Beautiful Sissy in chastity luvs being smashed

4 years ago

VideoSection

sissy, chastity, couple
21:51

Submissive Sissy Chastity Buttplug Play

5 years ago

ShemaleZ

BDSM, ass, toys, chastity, crossdresser
12:42

Sexy Trans Girl Sophie Struggles Helplessly in Bondage and Chastity

5 years ago

TrannyGem

bondage, BDSM, chastity
13:01

Sissy riding dildo in Public Compilation 3

1 week ago

xHamster

public, dildo, ladyboy, compilation, riding, masturbation, sissy
15:39

Sissy playing with dildo until cumming

3 months ago

xHamster

dildo, solo, crossdresser, sissy, chastity, finnish
12:02

Muzzled and Locked She-Male Trussed by Emo Female Dom

2 years ago

TrannyGem

femdom, emo, strapon, lesbian, gagging, bondage, goth
13:29

Day six in v-card: Unboxing brand fresh iron purity cell by myinside.es and edging me with wand

2 years ago

TrannyGem

femdom, tease, bondage, clit, chastity, sissy
15:04

CROSSDRESSER PLAYS WITH MAN-MEAT IN V-CARD BELT AND PANTYHOSE AND HIGH STILETTOS

3 years ago

TrannyGem

pantyhose, bondage, cuckold, chastity, crossdresser
03:00

Big dick femboy show before chastity

1 week ago

AShemaleTube

stockings, big cock, femboy, sissy, solo
10:42

Chastity Sissy Slut assfuck climax Encouragement - Jessica Bloom

3 weeks ago

ShemaleMovie

train, huge dildo, anal, orgasm, dildo, slut, sissy
06:59

Trans-Damsels Rails HorseCock To Chastitied Jism

1 month ago

KeekAss

chastity
07:25

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

4 months ago

xHamster

beauty, squirt, prostate, dildo, machine, sissy, chastity
07:26

TS Mariaqt chastity fuck machine cum

8 months ago

AShemaleTube

amateur, compilation, cumshot compilation, sissy, chastity, machine
13:58

Im going to put you in virtual chastity Trans JOI

10 months ago

XXXDan

femdom, POV, british, nylon, JOI, chastity
06:51

BBC Ken Fucks Me on My Back in Missionary with Verbal Dom Sissification - Candy Ass Sissy in Chastity Cage

1 year ago

xHamster

BBC, sissy, missionary, chastity
04:17

Trans mommy with big tits, in chastity, taking a huge dildo

1 year ago

AShemaleTube

mom, homemade, huge dildo, crossdresser, toys, chastity
29:13

Black BlackTGirlsHardcore - Chastity Kane

2 years ago

BeMyHole

ebony, pantyhose, black, boots, tattoo, shemale fucks guy, chastity
18:09

Lily Star Ass to mouth and leaking out of chastity

3 years ago

AShemaleTube

ass to mouth, chastity
03:50

Dude fucks anus of ladyboy Lianna Lawson wearing chastity cage

4 years ago

AnySex

chastity
06:21

Gina in chastity, pleased and spanked

4 years ago

ShemaleZ

BDSM, spanking, chastity
14:57

Chastity sissy forced to cum by Mistresses

5 years ago

ShemaleZ

femdom, chastity
05:17

Chastity Michaels in Chastity Michaels Lusciousness - BlackTGirls

5 years ago

TXXX

ebony, chastity
13:52

Encaged Clitty Trans Sissy Gets Unending Vibrates by Aficionados During Live Fountain

2 months ago

TrannyGem

chastity, sissy, feet, BDSM, amateur, fetish
07:23

Sissy chick rails fat plaything while being locked jessiesissyadventures

2 months ago

TrannyGem

fat, dildo, crossdresser, 18, sissy, chastity, femboy
12:01

TRANSEROTICA Fabulous Dark-Haired Jamie Kelly Pummels Stiff Nyxi Leon

4 months ago

TrannyGem

ass licking, ass to mouth, shemale, chastity
10:07

Crossdresser gets machine fucked with XXL Monster Dildos #7

5 months ago

xHamster

monster, german, chastity, crossdresser
06:17

Femboy Booty Spread by Monster BIG BLACK COCK Fake Penis

9 months ago

TrannyGem

BBC, chastity, machine
05:15

SISSY SLUT SHOWS OFF AND PUSHES OUT BUTT PLUG

11 months ago

xHamster

pantyhose, teen (18+), teen anal (18+), crossdresser, sissy, chastity
05:02

Amateur And Trap With Boyfriend Sissy Fits 11 Inches In Her Throat

1 year ago

BeMyHole

boyfriend, chastity, femboy, shemale fucks guy
11:37

TOTAL Sissy Mara Jades Railing Compilation

2 years ago

TrannyGem

public, train, crossdresser, chastity
10:46

Stefani footwear assfuck in innocence ,gulp jizm

3 years ago

TrannyGem

boots, chastity
16:48

Sissification Lecture encaged Sissy Innocence Belts, Fap, Sissygasm by Dominatrix Veronica Taboo

3 years ago

TrannyGem

train, instruction, tease, JOI, chastity
05:57

Cum in chastity

1 week ago

AShemaleTube

shemale, small cock, chastity
11:20

Crossdresser fucks her ass with a dildo sex in her chastity cage

1 month ago

XXXDan

crossdresser, chastity

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