TRANNY • CHASTITY 2,267 videos

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10:07

Chastity Sissy Slut Anal Orgasm Encouragement - Jessica Bloom 10 Min

9 months ago

ShemaleZ

orgasm, solo, chastity
12:42

Crossdresser femboy Sissy Kat leaks in chastity and sissygasms

5 years ago

ShemaleZ

chastity
05:04

Charlotte See Goode

1 year ago

xHamster

french, chastity
04:32

Mara Jade In Inverted Chastity Cages Makes You Feel So Slutty & Submissive 5 Min

10 months ago

Upornia

amateur, chastity
02:31

Assfuck in chastity

1 year ago

xHamster

chastity
01:55

Sissy put on chastity belt

4 years ago

xHamster

chastity
40:39

Sissy In Red Nightie Fucks Her Ass While Locked In Chastity

1 year ago

ShemaleZ

chastity
05:42

Cute Trans In Chastity Cums From Anal

2 years ago

ShemaleZ

chastity, cum in ass
02:52

Chastity Tears, Showcasing, And Frustration

2 years ago

xHamster

latex, chastity
04:04

Sissy Cd Slut Riding Dildo Training For Sissygasm In Chastity (almost Cum)

1 year ago

ShemaleZ

dildo, chastity, cum in ass
18:33

DEBBIE IN CHASTITY

5 years ago

ShemaleZ

chastity
19:40

Shemale samurai challenges you to take her chastity

5 years ago

ShemaleZ

toys, chastity
01:27

Elmo Fucks Transgender in Chastity

1 year ago

xHamster

chastity
09:47

Removes Chastity Then Jerks Off - Bailey Wilde

10 months ago

ShemaleZ

webcam, chastity
10:15

Jessica Bloom Riding Monster Dildos Multiple Anal Orgasms in Chastity

2 years ago

xHamster

orgasm, monster, anal orgasm, chastity
04:17

Trans Woman in Chastity Fucked Cowgirl Raw

1 year ago

xHamster

chastity
02:57

Sissy Training Hankeys XL Seahorse in Micro Chastity Cage

3 years ago

xHamster

public, train, chastity
14:35

Sissy Sky in lingerie and chastity daof anal training with multiple dildos and cum once hands free and again right after

9 months ago

xHamster

dildo, lingerie, sissy, hands free, chastity
06:24

Hot Sissy In Chastity Fucks Herself With Her Big Dildo

1 year ago

ShemaleZ

chastity
01:16

Oiled sissy body in small chastity

1 year ago

xHamster

swedish, chastity
13:09

Insanely deep Toy fucking. Using a Machine and more.

2 years ago

xHamster

german, machine, chastity
02:15

Sissy in chastity blowjob and anal sweet ass

7 years ago

xHamster

chastity
11:06

Holy Nun Astrid Apathy Sissygasm In Chastity

3 years ago

ShemaleZ

nun, skinny, chastity
02:24

Man Dressed as Woman in Chastity and Strapon Fucked

1 year ago

xHamster

strapon, crossdresser, dress, sissy, chastity, femboy
05:58

Chastity sandy

6 years ago

ShemaleZ

chastity
08:19

Sexy Sissy in Chastity Strapon Fucked by Dominatrix

1 year ago

xHamster

strapon, chastity, femboy
03:09

Sissy Sherri Fucked While Tiny Cock Is Caged In Chastity

1 year ago

ShemaleZ

chastity, sissy
07:44

Sissy In Chastity Cums With Vibrator And Uses Cum As Lube A2m - Jessica Bloom 8 Min

10 months ago

ShemaleZ

stockings, cum in mouth, chastity, cum in ass
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
04:06

Cute Blonde Cums RIght Into Her Mouth Through Her Chastity Cage

2 years ago

xHamster

cute, chastity
21:40

New Deep Love Vol.1 - Episode 5

2 years ago

xHamster

chastity
33:20

Trans Latex Hands Free Cum Piss Drinking Chastity Fuck Xxxsamanthaphd

8 months ago

ShemaleZ

shemale, pissing, chastity, latex
01:12

Practice Makes Perfect

2 years ago

xHamster

chastity
06:57

Shemale Chastity

5 years ago

ShemaleZ

chastity
07:30

Femboy Sissy Lay With Vibrator In Chastity

2 years ago

HClips

vibrator, chastity
11:09

Sissy in chastity

5 years ago

ShemaleZ

chastity
07:53

denim biker chick in chastity device

9 years ago

xHamster

outdoor, chastity
05:35

Trying to get the fist in

5 months ago

xHamster

chastity, crossdresser, ladyboy, fisting, mature
03:43

Sissy sarah in chastity shaving

2 years ago

xHamster

small cock, shaving, chastity
02:29

Locked up in chastity - Alison wearing a see through dress

6 years ago

xHamster

dress, chastity
06:15

Chastity Gets Vibrated Her Clitty Projectile Squirt Cummies Her Tiny Balls Spanked & Turning The Fuck Machine Up To Its Max!

11 months ago

Upornia

squirt, spanking, machine, vibrator, chastity
08:52

Ice un the Ass

1 year ago

xHamster

chastity
05:11

Sultry black TS Chastity Michaels alternately fucks with stud

7 years ago

ShemaleZ

chastity
03:43

Trans Woman Takes Twin Tail Creations Croxic In Chastity 4 Min

1 year ago

ShemaleZ

chastity
05:29

Sissy Locked in Chastity Fits 11 Inches Down Her Throat

1 year ago

xHamster

chastity
06:23

Chastity Sissy & Fuck Machine

5 years ago

ShemaleZ

machine, chastity
01:58

Sissy in chastity and in estim

2 years ago

xHamster

chastity
10:12

Transgender Slut Lilith Eclipse Fisting Herself and Playing With Her Asshole in a tiny Chastity Cage and Dark Pantyhose

2 years ago

xHamster

pantyhose, fisting, goth, asshole, slut, chastity
53:05

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

1 year ago

xHamster

orgasm, bondage, chastity, post op
26:49

Spiked Chastity Cage Self Bondage

2 years ago

xHamster

latex, huge dildo, bondage, chastity
04:08

Sissy Lili In Chastity Plays With Anal Glass Toy And Inflatable Buttplug

2 years ago

ShemaleZ

glasses, chastity
01:09

Dildo fuck in chastity

4 years ago

xHamster

chastity
01:15

Subby's Secret... Tranny with chastity belt and gag while shopping!!

1 year ago

xHamster

public, german, gagging, BDSM, chastity
03:55

Trans chastity fucks Dildo hard

1 year ago

xHamster

chastity
05:32

Chantals tiny Clitty is caged in super small Chastity and she is fucked until juicy Sissygasm

2 years ago

xHamster

slut, chastity
03:45

Sissy TGirl Lucy Pissing In Her Chastity Cage at SheWorld

4 years ago

xHamster

pissing, chastity
06:43

Sissy selfbondage breathplay

4 months ago

xHamster

ladyboy, chastity, BDSM
07:59

FIRST SISSYGASM Chastity Slut Misty Cane Cums in her Cage with vibrating wand

2 years ago

xHamster

vibrator, slut, JOI, chastity
01:42

Sissy Lucy in Chastity being plugged by mistress

3 years ago

xHamster

femdom, mature anal, domination, chastity
01:01

Latex Drone Gets Horny In The Chastity Cage

1 year ago

xHamster

latex, chastity
28:18

Sissy Maids Self Bondage Armbinder and Chastity Belt

3 years ago

xHamster

latex, bondage, maid, chastity
01:30

Paula - In chastity riding on a dildo again

9 years ago

xHamster

dildo, chastity
05:11

Ebony TS Chastity Michaels bangs wild her lovers ass in bareback sex

9 years ago

TXXX

chastity
10:48 47%

Real sissy in in natures garb beach in chastity and rosebud

9 years ago

TXXX

beach, outdoor, natural, chastity
18:24

Sissy Maids Spiked Chastity Cage Self Bondage in New Boots

1 year ago

xHamster

bondage, boots, maid, JOI, chastity
03:15

Rose Sissy plug and chastity belt is a great little slut xxx

4 years ago

xHamster

vintage, JOI, chastity
04:18

Sexy Transgender in Chastity Deepthroats Huge Dick

1 year ago

xHamster

chastity
04:02

HUGE ASS TS in Chastity Fucked Doggystyle

1 year ago

xHamster

BDSM, dogging, chastity
01:20

Dildo fuck in chastity pt2

4 years ago

xHamster

chastity
16:00

In chastity and lingerie playing with my ass

6 years ago

xHamster

chastity
01:12

Cop Fucks Trans Woman in Chastity

1 year ago

xHamster

BDSM, 18, chastity
33:18

She Let Him Out Of Chastity

5 years ago

ShemaleZ

blowjob, chastity
02:03

Sissy Boy Pink Dildo Fuck

1 year ago

xHamster

chastity
06:12

Sissy Slut Fucks Bad Dragon Dog Dildos Rex and Austin Chastity

5 years ago

ShemaleZ

dildo, dogging, slut, chastity
13:00

SisK dressing up pink satin nightgown

2 years ago

xHamster

thai, satin, crossdresser, dress, chastity
17:40

Sissy milking and cumming handsfree... in chastity!!

7 years ago

xHamster

milk, hands free, chastity
07:28

Femboy Sissy Plays In Chastity

3 years ago

HClips

chastity
12:40

Sissy In Chastity Playing And Cums Hard

2 years ago

Upornia

chastity
01:04

Cumming Like a Good Slut

1 year ago

xHamster

chastity
02:12

Negative Cage hardcore Cumload

1 year ago

xHamster

hands free, chastity
02:28

Chubby sissy gets to wand in chastity

2 years ago

xHamster

fat, chubby, BBW, chastity
06:45

Soft sissy sadie in chastity clitty dripping ride

6 years ago

TXXX

chastity
03:48

Sissy Emma wet panties in chastity

5 years ago

ShemaleZ

panties, wet, chastity
08:53

Sissy slave Oksana shows her master sissygasms from anal training on a big black dildo

1 year ago

xHamster

orgasm, anal orgasm, chastity, sissy
05:02

Trans Girl Jada Dulce Ass To Mouth Toying & Anal Dildo Riding In Chastity (full Vid On

2 years ago

ShemaleZ

ass to mouth, chastity
08:44

Sashas Dollhouse - Christmas Chastity And Dildo Ass Play

2 years ago

ShemaleZ

chastity
12:43

Chastity Cage Assfuck

1 year ago

ShemaleZ

chastity
04:55

Sissy Dagmar321 plugged chastity cage whore

5 years ago

xHamster

mature anal, vintage, whore, chastity
09:46

Latex Sissy gets used

3 months ago

xHamster

dildo, crossdresser, chastity, latex
57:56

Sissy Lucys Toy Time In Chastity

3 years ago

HClips

chastity
06:40

Slutty Sissy Shay Double Sissygasm in Chastity!

5 years ago

TXXX

double penetration, chastity
01:45

Pizza Delivery Guy Fucks Transgender in Chastity

1 year ago

xHamster

chastity
01:55

Sexy sissy crossdresser in chastitty on sofa

1 year ago

xHamster

chastity
05:38

Crossdressing sissy fingering her arse, fucking a huge dildo then ripping off her chastity cage for two huge cumshots

1 year ago

xHamster

latex, mature anal, huge dildo, british, chastity
01:13

Cop Fucks Trans Woman in Chastity

1 year ago

xHamster

chastity
07:16

Putting on my urethral chastity cage

4 years ago

xHamster

chastity
12:57

Chastity Sandy Shemale Fucked

5 years ago

xHamster

chastity
01:30

Chastity Addiction

1 year ago

xHamster

chastity
04:47

Transvestite Ananny Mass Squirting /// (chastity Belt + Piston Machine)

1 year ago

ShemaleZ

squirt, chastity
07:17

Niqab shemail locked in chastity and fucking dildo

6 months ago

xHamster

small cock, chastity
02:48

White Lingerie and Chastity

4 years ago

xHamster

chastity
09:52

Sissy Maid Cleaning Bathroom in Steel Chastity Belt with Dildo Locked in Place

1 year ago

xHamster

femdom, bondage, maid, BDSM, bathroom, chastity
13:27

Self Bondage 2 Litre Enema Hand Cuffed to Toilet in Chastity and Gagged

2 years ago

xHamster

toilet, gagging, bondage, chastity
02:02

Rapper Fucks Trans Woman in Chastity

1 year ago

xHamster

chastity
13:47

Brutal Big BBC Dildo in my Sissy Holes

1 year ago

xHamster

BBC, chastity
03:33

Fat Sissy Pig Won't Get Hard After 2 Weeks of Chastity

4 years ago

xHamster

fat, chastity
06:11

Sissy Monika CD in Chastity cumming on a Huge black Dildo

10 months ago

xHamster

black, huge dildo, chastity
03:31

Sissy chastity with a huge and buttplug deep in your ass

2 years ago

xHamster

JOI, chastity
03:30

Cute Sissy Slut in Chastity

2 years ago

xHamster

slut, chastity
02:37

Outdoor pee shower even worried in the chastity belt

1 year ago

xHamster

pissing, public, german, shower, chastity
03:14

Sissy chastity poppertrainer featuring sissy joyce

3 years ago

xHamster

chastity
05:01

Ab051 Latex Sissy In Chastity And Fucked By Mistress - Bdsm乳胶人妖贞操锁被女王用假阳具抽插

3 years ago

ShemaleZ

femdom, latex, fetish, chastity
17:39

Chastity Guide : A review of all metal chastity cages!! - By Sissy Joyce

4 months ago

xHamster

chastity, sissy, fetish, toys
05:19

Transvestite Annie A Horny Mans Daughter Who Squirts So Much That Her Chastity Belt Becomes Soaked

1 year ago

ShemaleZ

squirt, chastity
16:58

Ruined Orgasm In Chastity And Cbt For Lana Trap

3 years ago

ShemaleZ

teen (18+), fetish, orgasm, BDSM, toys, domination, chastity
14:38

Fan Request 2: Lineaiguille. Pussy Eating Blowjob Creamie And Facesitting Crossdressed In Chastity

1 year ago

ShemaleZ

facesitting, shemale and girl, chastity
04:14

Taking off the chastity cage

5 years ago

xHamster

chastity
10:46

Multiple Prostate Orgasms In Chastity Jessica Bloom A S

1 year ago

HClips

prostate, orgasm, chastity
03:37

Tina Noxx stretches her poor butt with an inflatable plug

2 years ago

xHamster

chastity
06:25

Love Tasting My Own Ass Juices, Especially While Locked in Chastity

1 year ago

xHamster

chastity

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