TRANNY • CHASTITY 2,189 videos

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10:23 96%

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

4 months ago

xHamster

feet, femdom, lesbian, dildo, british, anal orgasm, chastity
17:26 96%

Pretty Trans In Cock Chastity Cage Has An Anal Prostate Orgasm And Cum Explodes While Fucked Hard And Fast With A Huge Dildo Fuck Machine 18 Min

2 years ago

ShemaleZ

huge dildo, prostate, orgasm, dildo, redhead, 18, machine
04:34 95%

Sissy Slave - Shackled Chastity Takes Super-sized Dildo And Femdom Latex Fisting By Mistress Mercer

1 year ago

HClips

femdom, latex, fisting, dildo, BDSM, webcam, sissy
29:14 94%

Shemale Sub In Chastity Takes Bbc And Gets Cum Filled

3 months ago

ShemaleZ

amateur, shemale, interracial, lingerie, bareback, BBC, chastity
11:59 94%

In the Chastity Cage

3 years ago

ShemaleZ

handjob, BDSM, chastity, stockings
07:07 94%

Sissy Bailey Wilde in Chastity Fucked

4 months ago

xHamster

big ass, crossdresser, bareback, sissy, chastity, femboy, cum in ass
04:34 93%

Sissy Anal Slut Locked Down On Huge Dildo One Bar Prison Bound & Teased In Chastity Cage By Mistress

1 year ago

HClips

femdom, shemale, huge dildo, tease, BDSM, shemale and girl, slut
03:09 92%

AB085 Lustful Abby Kitty be Master's sissy slave -chastity (Chinese and English subtitles)

6 months ago

xHamster

pantyhose, dildo, dirty talk, chinese, sissy, chastity
03:37 92%

Gaping myself and cumming hands free

1 year ago

xHamster

russian, sissy, gape, hands free, chastity
08:24 91%

Goddess In Chastity Fists Her Perfect Ass To Orgasm

1 year ago

HClips

orgasm, fisting, chastity
41:24 89%

Natalie Mars And friend Feminized In Chastity slavery

4 years ago

ShemaleZ

fetish, BDSM, chastity
19:29 89%

Luna In Chastity Cage Gets Horny And Cums - Luna Rodriguez Montero

3 years ago

HClips

BDSM, cum in mouth, chastity, brunette, solo
10:05 89%

Sexy Blonde Sissy Bailey Wilde in Chastity Fucked

2 months ago

xHamster

amateur, crossdresser, sissy, chastity, femboy, cum in ass
15:51 88%

Sissy Joyce In The Complete Chastity Review & Guide - All Sizes

1 year ago

ShemaleZ

solo, sissy, chastity, BDSM
03:40 88%

Sissys in chastity

4 years ago

xHamster

latex, chastity
01:33 88%

Chastity T-Girl goes wet, Claire Tenebrarum, 5on1, Anal Fisting, DAP, Gapes, Pee Drink, Swallow BTG063 - PissVids

5 months ago

TXXX

pissing, fisting, shemale and girl, swallow, gape, chastity
08:13 88%

Pretty Tranny Anus Plug With Chastity

1 year ago

TXXX

chastity
14:37 86%

The church of Hentai

1 year ago

PornHub

homemade, stockings, boots, nun, cosplay, chastity
13:34 86%

Real sissy full in chastity

8 years ago

xHamster

BDSM, full movie, toys, chastity, sissy
04:26 86%

VERY HOT Blonde Crossdresser in Chastity Fucked Doggy Style

3 months ago

xHamster

amateur, crossdresser, 18, sissy, chastity, femboy
04:54 86%

Mistress And Chastity Sissy Slut Anal Training 5 Min

1 year ago

ShemaleZ

femdom, train, slut, sissy, chastity
06:39 86%

Happy woman full time in chastity device nylon stocking

4 years ago

ShemaleZ

mature, stockings, BDSM, nylon, chastity
04:29 85%

Sissy put into chastity and tormented

4 years ago

ShemaleZ

fetish, BDSM, toys, chastity
02:12 83%

Leaking alot caged

9 months ago

xHamster

teen (18+), hands free, chastity
08:34 83%

Melody Lane Chastity tipped into

4 years ago

ShemaleZ

masturbation, chastity
10:00 83%

Chastity Teen Fucked By Her Daddy

2 years ago

ShemaleZ

chastity
15:32 82%

Russian Femboy Fucks With Mistress For The First Time With A Huge Strapon Tied With A Chastity

2 years ago

ShemaleZ

femdom, strapon, russian, fisting, tied, first time, chastity
33:30 82%

Chastity male vs shemale

5 years ago

ShemaleZ

BDSM, shemale and girl, vintage, chastity
26:40 82%

Chastity Caged No Hand Cum Compilation

7 months ago

ShemaleZ

stockings, BDSM, compilation, selfsuck, hands free, chastity
25:22 82%

Chastity Sandy Loves Black Cocks

7 years ago

TXXX

black, interracial, bareback, chastity
02:12 82%

NEGATIVE CHASTITY double cumshot

10 months ago

xHamster

teen (18+), double anal, hands free, chastity
20:23 81%

Hot Sissy Misses Anal And Fucks Herself In The Ass Until She Cums In Chastity Belt

2 years ago

ShemaleZ

MILF, sissy, chastity, cum in ass
1:02:33 80%

Chastity T Girl Wet Dap, Double Anal Fisting, Wrecked Ass, Almost Rose, Pee Drink, Creampie, Swallow Btg0 With Natalie Mars

1 year ago

TXXX

pissing, creampie, anal, fetish, fisting, BDSM, double anal
09:48 80%

Sexy Sissy Femboy Blowjob And Jizz Swallow In Chastity

2 years ago

Upornia

swallow, sissy, chastity, femboy
1:06:07 80%

Taryn Elizabeth gets strapon while in chastity

4 years ago

ShemaleZ

strapon, chastity
11:15 79%

Sissy Fucks Herself With A Dildo In A Chastity Belt Using Her Cum As A Lubricant

1 year ago

ShemaleZ

dildo, toys, chastity, cum in ass
10:48 79%

Jessica Bloom Multiple Caged Assgasms

2 years ago

PornHub

pissing, feet, squirt, dildo, british, heels, chastity
14:08 79%

Neon Rave Trans Party Hooker Deepthroated Then Locked In Chastity And Drilled

3 years ago

HClips

party, hooker, deepthroat, chastity
20:26 79%

Sissy In Chastity Pounds Pussy Hard Until She Makes Cummies

1 year ago

ShemaleZ

amateur, webcam, sissy, chastity
05:29 79%

Machine Spit Roast Chastity Fuck In Bondage

3 years ago

ShemaleZ

latex, bondage, machine, domination, chastity
07:38 79%

Chastity Fuck

4 years ago

HClips

chastity
12:24 77%

TGirl Lucy in Chastity is fucked by 10 inch BBC at SheWorld

4 years ago

xHamster

interracial, BBC, chastity
21:22 77%

Skitty&M&L in Our first fun Together

1 year ago

xHamster

latex, german, BDSM, sissy, chastity
28:13 77%

Working from home as a Chastity Sissy Secretary is so much fun

3 years ago

PornHub

femdom, shemale, fetish, fisting, crossdresser, british, glasses
13:41 77%

Sissy shaves her useless clitty and wears chastity device

4 years ago

xHamster

shaving, chastity
05:15 76%

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

2 years ago

xHamster

german, chastity
21:26 76%

Chastity estim cum for cute sissy

2 years ago

xHamster

cute, orgasm, BDSM, crossdresser, chastity
11:39 75%

Squeezing a penis into a micro cage

1 year ago

PornHub

train, insertion, penis, chastity
01:54 74%

Daddy made me a new milking toy on my chastity

2 years ago

xHamster

milk, 18, chastity
11:09 74%

Sissy Chastity Torture With Natalie Mars

1 year ago

ShemaleZ

handjob, chastity
09:51 74%

Crossdresser nun in chastity pleases daddy

4 years ago

xHamster

couple, crossdresser, nun, toys, domination, chastity
10:46 73%

Stefani boots anal in chastity ,swallow cum

4 years ago

xHamster

latex, creampie, anal, couple, boots, swallow, bareback
08:44 73%

Dominatrix Fucks Hot Crossdresser In Chastity

6 months ago

ShemaleZ

BDSM, crossdresser, chastity
02:34 72%

SISSIES IN CHASTITY

3 years ago

xHamster

amateur, sissy, chastity
08:14 72%

Chastity Cage On Her Penisthai Ladyboy Threesome Fucked

2 years ago

TXXX

chastity
12:04 72%

Sissy Chastity Slave Teased And Humiliated By Mistress Denied And Locked In The Vice

3 years ago

ShemaleZ

femdom, tease, webcam, sissy, chastity
06:47 72%

Sissylucylove Trans Chastity Bull Busting

2 years ago

Upornia

chastity
11:10 72%

Sissy chastity (part 1)

1 year ago

PornHub

russian, cosplay, chastity
04:42 71%

PorchaeTS tries new homemade chastity Dick dildo to pleasure the Mrs. Total mind trip.

6 months ago

xHamster

huge dildo, fetish, chastity
16:39 71%

Trans girl in chastity plays with dildos and fists herself

2 years ago

xHamster

cute, teen anal (18+), fisting, solo, 18, chastity
11:58 71%

Teen sissy in chastity fucked by muscle Daddy

4 years ago

ShemaleZ

muscle, chastity
16:59 71%

Edging Lana To Multiple Ruined Orgasms After 4 Weeks In A Chastity Cage

2 years ago

HClips

orgasm, shemale and girl, chastity
33:24 71%

Sissys Wooden Pony Ballet Boot Torment

9 months ago

xHamster

latex, fetish, bondage, boots, lingerie, BDSM, chastity
16:51 70%

Cute pink haired trans woman masturbating in chastity

1 year ago

xHamster

cute, dildo, BDSM, anime, chastity
06:12 69%

The Start of Perminant Chastity

5 years ago

ShemaleZ

fetish, BDSM, chastity
10:46 68%

Sissygasm Slut Caged Training Massive Cumshot & Anal Milking Jessica Bloom

1 year ago

PornHub

cute, train, orgasm, dildo, milk, monster, british
14:24 67%

Horny sissy tease penis electro slut , only one drop cum 2/2

1 year ago

PornHub

tease, orgasm, cuckold, electro, chastity
04:09 67%

Chastity slave sissy wife tormented by Mistress

4 years ago

ShemaleZ

femdom, wife, BDSM, chastity
18:03 66%

Gigantic Strapon Pegging For Chastity Sissy Slave Destroying Her Slutty Hole By Mistress Mercer

2 years ago

Upornia

femdom, strapon, fetish, BDSM, pegging, chastity
19:08 65%

Chastity Shemale Takes Interracial Anal Reaming And Creampie

5 months ago

ShemaleZ

creampie, anal, interracial, 18, bareback, chastity
05:40 65%

MaureenNadh - Hijab Sissy Squirt While Anal Training Using Chastity Cage

1 year ago

xHamster

arab, train, squirt, teen anal (18+), penis, chastity, FTM
02:10 64%

Bound Bimbo

2 years ago

xHamster

bondage, machine, chastity
12:17 64%

Lana S - Bombi Looses Her Anal Virginity To Fingers And Butt Plug Chastity Tease

2 years ago

HClips

amateur, anal, fetish, tease, toys, webcam, chastity
05:15 64%

Chastity & Ass to mouth with BIG black cock

2 years ago

xHamster

black, small cock, ass to mouth, BBC, chastity
16:00 64%

Baby Doll - Sissy Chastity, Fills Hole And Is Humiliated

2 years ago

HClips

doll, sissy, chastity
09:42 63%

Sissy In Chastity Sucking Shemale Cock

1 year ago

Upornia

webcam, sissy, chastity
28:47 62%

Lizzy Yum August 2022 #1 Chastity Vagina Tits prisoner of love and chore

1 year ago

xHamster

bondage, chastity, post op
03:18 58%

Permanent chastity - PERMALOCK

7 months ago

xHamster

small cock, chastity
15:03 58%

Chastity Tgirl Gets Double Anal Fucked In A With Itzel Saenz And Hardcore Gangbang

1 year ago

ShemaleZ

POV, double anal, gangbang, toys, double penetration, hardcore, chastity
05:36 57%

Double Machine

1 year ago

xHamster

fetish, double anal, 18, machine, double penetration, chastity
03:16 57%

Sissy pisses in urethral chastity cage in slow motion

2 years ago

xHamster

pissing, chastity
07:33 57%

Full time chastity

5 years ago

ShemaleZ

stockings, latex, chastity
10:20 56%

Sissy Boy Takes Huge Load In His Ass

9 months ago

PornHub

femdom, strapon, huge dildo, socks, pegging, sissy, chastity
08:41 54%

Crossdresser Compilation Beautiful Ladyboy Fucked Sissy Chastity Fucked Femdom

2 years ago

ShemaleZ

femdom, fisting, BDSM, crossdresser, chastity
06:33 54%

Sissy Try To Cum In Micro Chastity Cage

11 months ago

ShemaleZ

amateur, POV, toys, sissy, chastity
11:49 53%

Tricked into sissification tricked into chastity (New Vids on MANYVIDS)

4 years ago

HClips

latex, fetish, BDSM, chastity
11:11 53%

Rainbow Kitty Scarlet Sky Squirts Girl Cum!

6 months ago

PornHub

cute, squirt, orgasm, cumshot, masturbation, sissy, chastity
07:04 50%

Get ready to fuck me and cum... I'll wait for you in chastity and with my ass open

10 months ago

xHamster

mature, mature anal, crossdresser, chastity, cum in ass
20:59 50%

Sissy Brittanie Masturbates In Chastity To Hypno

3 years ago

ShemaleZ

lingerie, chastity
13:02

Clark Delgaty - Heteroflexible - Femboy Kay La Soumise Gets Anal Creampied By For Chastity Cage Key

4 weeks ago

ShemaleZ

shemale, creampie, ladyboy, bareback, chastity, femboy
07:10

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

1 week ago

PornHub

amateur, anal, solo, swallow, cumshot, blonde, machine
07:58

Cute Femboy In Chastity Ride My Big Cock

1 month ago

TXXX

amateur, cute, stockings, teen (18+), fetish, riding, chastity
12:14

Cumming & Squirting - uncut version

9 months ago

xHamster

pissing, squirt, prostate, orgasm, hands free, chastity
05:38

Trans cums so hard in chastity while fucking her hole

1 week ago

PornHub

amateur, chastity, solo, feet, cum while fucked
17:41

Dirty priest tied up and humiliated her slave

3 years ago

xHamster

femdom, russian, bondage, BDSM, tied, chastity
10:01

Very Hot Blonde Crossdresser In Chastity Fucked

1 week ago

ShemaleZ

crossdresser, amateur, stockings, chastity
1:39:12

Tgirl_fun 2022-2-7 Chaturbate Stream

1 year ago

PornHub

bondage, BDSM, tied, chastity
20:24

Latex Sissy Disciplined By Chastity Fuckmachine Spanking Cocksucking Pegging By Mistress Mercer

2 years ago

TXXX

femdom, latex, shemale, fetish, BDSM, spanking, shemale and girl
08:24

My full frustrating chastity journey (trans girl)

1 month ago

PornHub

cosplay, 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
18:50

Sissy Long Term Chastity

6 years ago

xHamster

POV, sissy, chastity, shemale fucks guy
10:18

Chastity Shemale Getting Fucked Long And Hard - Lianna Lawson

1 year ago

TXXX

bareback, chastity
07:05

Locked In Chastity Under My Pretty Pink Dress

1 month ago

PornHub

fetish, dress, small tits, chastity
01:04

Femboy in flat chastity cums with a vibrator like a bitch

5 months ago

xHamster

small cock, prostate, hands free, chastity, femboy, asian
10:13

Chastised sissy Tgirl Lily Star Dribbles clitty nectar through her cage

7 months ago

PornHub

arab, fetish, bondage, dildo, masturbation, BBC, hands free
17:19

Public humiliation locked, plugged, gagged, clamped and squirt

5 days ago

xHamster

outdoor, chastity, BDSM, sissy
19:03

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

2 months ago

xHamster

beauty, shemale, big ass, dildo, chastity, cum in ass, cum while fucked
21:23

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

10 months ago

xHamster

feet, dildo, chastity
01:38

Latex Kitty Gets Horny In The Chastity Cage

4 months ago

xHamster

latex, chastity
10:55

SissyCDMish - qos sissy camwhore with chastity cage, butt plug and dildo

4 days ago

xHamster

shemale, crossdresser, amateur, sissy, dildo, chastity, anal
08:26

Anal Orgasm In Chastity Cage For A Tied Femboy

4 weeks ago

ShemaleZ

amateur, stockings, shemale, big ass, couple, orgasm, BDSM
07:10

Best Feminization Ever (clothes / Make Up / Boobs / Chastity / Nails / Plug / High Heels)

1 week ago

ShemaleZ

shemale, clothed, chastity, heels
09:43

Vibrating my clit, chastity fail ends in self suck!

1 week ago

xHamster

shemale, selfsuck, facial, cum in mouth, homemade, chastity, vibrator
42:34

Chastity T-girl 4on1, Bwc, Atm, Balls - Itzel Saenz

1 year ago

ShemaleZ

shemale, anal, double anal, group, cum in mouth, double penetration, chastity
08:42

Live-cam Replay - Pegging my Slave in Chastity ! Subsribe to see full Video of 1hour Mistress Julia

1 week ago

PornHub

amateur, femdom, blowjob, fetish, pegging, chastity
25:11

Hi I'm Linzy19

11 months ago

xHamster

bondage, BDSM, monster, webcam, chastity
08:17

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

1 year ago

xHamster

pantyhose, ladyboy, chastity
12:25

Chastity Caged Anal Fuck Machine Play Plus Unlocking And Jerking Off Until Cum

9 months ago

ShemaleZ

chastity
02:15

Cumming through panties

9 months ago

xHamster

teen (18+), cumshot, panties, sissy, hands free, chastity, femboy
29:14

Tiffany Doll - Sissy Schoolgirl In Chastity Bred Wit

4 months ago

ShemaleZ

interracial, sissy, chastity

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