TRANNY • CHASTITY 2,073 videos

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01:12

Sissy Haileydoll In Chastity Anal Training And Gapes

2 years ago

xHamster

dildo, chastity
04:03

Hot Sissy In Chastity Strapon Fucked By Dominatrix

1 year ago

ShemaleZ

strapon, chastity
04:50

Sissy Dagmar321 plugged chastity cage whore

5 years ago

HClips

mature, whore, chastity
02:44

Davine locked in Prince Albert Chastity

2 years ago

xHamster

bondage, piercing, chastity
08:19

Chastity Caged At Bedtime

2 years ago

HClips

chastity
04:33

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4 years ago

xHamster

dildo, vintage, chastity
09:41

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8 years ago

xHamster

outdoor, chastity
08:43

Watch my ass take this 10inch cock deep and cum in chastity

3 years ago

xHamster

chastity, cum in ass
03:40

Bimbo Playroom

2 years ago

xHamster

machine, slut, chastity
06:01 75%

Chastity sissy anal training with huge black dildo

5 years ago

ShemaleZ

train, huge dildo, dildo, chastity, sissy, black
02:49

Chastity

7 years ago

xHamster

chastity
05:13

CD Lacy Rose Butt Plug, Dildo & Tail.

1 year ago

xHamster

homemade, chastity, heels
12:28

Caged Sissy pussy fucking machine in chastity

2 years ago

xHamster

german, chastity
02:48

The Meaning of Life - Diamond Chastity

10 years ago

xHamster

gangbang, chastity
07:56 67%

Pink Sissy Locking Her Tiny Limp Clitty In The Smallest Chastity Cage

4 years ago

ShemaleZ

chastity
05:52

Hot Sissy Anal Slide In Chastity Cage

2 years ago

HClips

chastity
14:26

Sissy Francesca Anal Play In Chastity

3 years ago

Upornia

toys, chastity
04:34

Big Dildo In Ass And Chastity. No Cum! - Amanda S

3 years ago

ShemaleZ

chastity, cum in ass
13:29

Sissylucylove Trans Cum And Eat My Cum Chastity Selfsuck Edge

3 years ago

ShemaleZ

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09:47

Sissy Maids Self Suspension Bondage

3 years ago

xHamster

bondage, maid, sissy, chastity
01:30

Sisk Unlock Her Chastity Cage and Play with Her Clitty Dick

1 year ago

xHamster

bathroom, chastity
02:17

Gasmasked Sissy Enjoying Extra Tight Chastity Cage

2 years ago

xHamster

latex, lingerie, tight, chastity, femboy
09:02

Gudrun And Angie In Chastity And Pump Plug Games

2 years ago

HClips

mature, stockings, lingerie, chastity
06:38 75%

Sissy Lucy Gets Spanked In Chastity 7 Min

4 years ago

HClips

spanking, chastity
1:00:38

Master fucking and fisting my ass with machine

2 years ago

xHamster

fisting, BDSM, machine, chastity
05:34

Slutty Sissy Pirate Cage Dance by Sissy Mindy

1 year ago

xHamster

solo, crossdresser, chastity, sissy
03:42

Dont Think About My Pussy Chastity Bitch

6 years ago

ShemaleZ

fetish, BDSM, chastity
02:56

Sissy sarah hypno locked up chastity

4 years ago

xHamster

chastity
10:18

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

1 year ago

TXXX

feet, femdom, POV, orgasm, sissy, anal orgasm, chastity
26:00

Casey The Anal Slut In Chastity Plays With Her Toys Part 2

3 years ago

ShemaleZ

MILF, slut, chastity
03:18

Sissy Princess - Chastity Training

2 years ago

HClips

train, chastity
15:31

Trans slave in chastity made to bury her belongings by her Mistress

5 years ago

ShemaleZ

femdom, BDSM, chastity
03:33

Chastity caged at bedtime

7 years ago

ShemaleZ

chastity
08:14

Erika Oak Cums In Chastity From Her Vibrator

3 years ago

xHamster

vibrator, chastity
16:51 70%

Cute pink haired trans woman masturbating in chastity

3 years ago

xHamster

cute, dildo, BDSM, anime, chastity, solo
02:19

Chastity Loads of cum

2 years ago

xHamster

hands free, chastity
08:44 75%

Dominatrix Fucks Hot Crossdresser In Chastity

1 year ago

ShemaleZ

BDSM, crossdresser, chastity
01:56

Alexis fucked in chastity

5 years ago

xHamster

chastity
08:50

Femboy In Chastity Cage Plays With His Bad Dragon Nova. Cums From Vibrator And Fuck Machine

2 years ago

TXXX

toys, machine, vibrator, chastity
09:39

Femdom strapon Chastity And sperm Feeding Compilation

6 years ago

ShemaleZ

femdom, strapon, sperm, domination, cumshot compilation, chastity
24:42

Crossdresser gets machine fucked with XXL Monster Dildos #5

12 months ago

xHamster

german, dildo, crossdresser, hardcore, chastity
08:08

Machine fucking in chastity cage

2 years ago

xHamster

BDSM, machine, chastity
04:36

Crystal Paige playing solo

2 years ago

xHamster

mature anal, heels, chastity
16:32

Sissy In Chastity Getting Her Asshole Whipped Before Getting Anally Barebacked

2 years ago

Upornia

asshole, chastity
10:20

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6 years ago

ShemaleZ

chastity
10:53

Sissy Maid Cd Anal Deep Throat In Chastity Sexyasiansis

3 years ago

TXXX

maid, sissy, chastity
01:19

Pee in Chastity outside

6 years ago

xHamster

pissing, chastity
11:09 86%

Femboy Cums In Chastity Then Strokes Himself To A Second Orgasm

2 years ago

ShemaleZ

orgasm, chastity
08:08

Chastity Cage On Her Cock Oriental Shemale Orgy Fucked

3 years ago

Upornia

asian, orgy, chastity
08:01

MercurySissy riding huge toy in chastity - trans sissy slut anal solo

2 years ago

xHamster

train, riding, slut, chastity
03:37

Sissy in chastity sucking cock

7 years ago

ShemaleZ

POV, chastity
13:04

Nasty Shemale Sorona Strokes Her Cock With A Hair Clip Chastity Cage And Cum All Over

2 years ago

ShemaleZ

chastity
05:55

Trans Kelsey Masters Big Ass Fucked Raw While In Chastity

2 years ago

ShemaleZ

big ass, chastity
02:45

Stupid and Stuffed

1 year ago

xHamster

dildo, crossdresser, sissy, chastity
08:06

Slutty Femboy Maid In Chastity Takes Rough Anal Training Oscar20xxx

2 years ago

HClips

train, maid, chastity, femboy
06:34

My games in a black dress and high heels

9 months ago

xHamster

chastity, amateur, crossdresser, sissy, black, russian
18:48

Trap In Chastity Cage Anal

3 years ago

ShemaleZ

blonde, chastity
02:07

Dominatrix Fucks Crossdresser Handcuffed in Chastity

1 year ago

xHamster

chastity, femboy
23:19

Ghotic trap solo in chastity

5 years ago

HClips

chastity
09:29 40%

Hotwife Fucks Her BBC Bull As Sissy Cuckold In Lingerie And Chastity Cage

5 years ago

ShemaleZ

cuckold, chastity
10:19

Anal Orgasms In Chastity Cage - Sissy Slut Jessica Bloom

1 year ago

xHamster

orgasm, fisting, british, anal orgasm, chastity
08:13

Sexy Sissy In Chastity Strapon Fucked By Dominatrix

1 year ago

ShemaleZ

strapon, chastity
16:00 64%

Baby Doll - Sissy Chastity, Fills Hole And Is Humiliated

3 years ago

HClips

doll, sissy, chastity, solo
07:45

Exposedforyou Sissy Strip Tease, chastity, plug, ass dildo

4 years ago

xHamster

mature anal, tease, strip, JOI, chastity
03:40

Sissy TGirl Lucy Pissing In Her Chastity Cage at SheWorld

5 years ago

HClips

pissing, sissy, chastity
03:55

Trans Woman Cowgirl Fucked In Chastity 4 Min - Kelsey Masters

1 year ago

ShemaleZ

chastity, latex
04:59

Sukey Wearing Chastity Belt 2

2 years ago

ShemaleZ

chastity
01:32

Sissy in Chastity, Sissy Panties, Sissy Tattoo

3 years ago

xHamster

panties, chastity
10:31

Multiple Anal Sissy Orgasms in Chastity Cage & Then Unlocked Massive Cumshot Jessica Bloom

3 years ago

xHamster

orgasm, chastity
06:29

Sissy Boy Cums In Chastity For Daddy

2 years ago

Upornia

sissy, chastity
08:22

Sissy riding BBC dildo in new dress

5 months ago

xHamster

pantyhose, german, fetish, dildo, crossdresser, riding, dress
07:41

Full fashion seamed stocking chastity girl

8 years ago

TXXX

chastity
07:16

PorchaeTS chastity Pissgasm from huge anal dildos

1 year ago

xHamster

pissing, huge dildo, hands free, chastity
05:47

Cutie Trans Sissy In Chastity Scarlet Sky Collared And Leashed To Wall For Playtime!

2 years ago

ShemaleZ

chastity
07:32

Young Sissy Casting Sissy Fucked Hard In Chastity Fisting Sissy Maker Sissy Story Extreme Pegging

3 years ago

ShemaleZ

casting, fetish, fisting, pegging, chastity, story
10:53

Sexy Sissy In Chastity Sexyasiansissy

3 years ago

Upornia

chastity
16:39

Trans Girl In Chastity Plays With Dildos And Fists Herself

2 years ago

ShemaleZ

fisting, chastity
09:09

Chastity Sandy Fucked Hard

5 years ago

xHamster

vintage, chastity
19:00

Sissy Lucy being locked in metal Chastity for Locktober

4 years ago

xHamster

couple, BDSM, 18, chastity
06:00

Sissy fucked hard while in chastity

1 year ago

xHamster

shemale, chastity, sissy, stockings, BBC
04:01

Chastity sissy machine-fucked sucking Daddy

5 years ago

ShemaleZ

machine, chastity
04:15 80%

Vlada Russian of tranny maid Fucks herself in the ass with a chastity belt

5 years ago

ShemaleZ

russian, maid, chastity
03:01

Fucking Machine And Chastity (cum At 1:30)

2 years ago

ShemaleZ

machine, chastity
07:41

Chastity life

5 years ago

TXXX

BDSM, chastity
02:15

Hot Trans Woman in Chastity Fucked Cowgirl POV

2 years ago

xHamster

chastity
06:24

Fucking Myself for a Hands Free Orgasm in My Metal Cage

10 months ago

xHamster

chastity, hands free
06:47

Chastity Sissy Public Self Bondage Part 1

5 years ago

ShemaleZ

public, fetish, bondage, crossdresser, sissy, chastity
02:48

Sissy Guzel plays with her clitty in the chastity belt

3 years ago

xHamster

russian, chastity
09:22

Ilandis In A Chastity Belt And Stockings Has Fun With His Anus Fucks Himself With An Artificial Dick

2 years ago

ShemaleZ

fisting, chastity
06:55

How a Sissy should Masturbate - Sissy - Crossdresser slut - Chastity with Vibrator - Sissy Joanna

1 year ago

xHamster

chastity
06:47

CUTE SISSY TRAP CUM IN CHASTITY WITH DILDO (FOXYQ SLUT)

5 years ago

ShemaleZ

dildo, toys, slut, chastity
20:28

Anal Training in Chastity

6 years ago

ShemaleZ

train, teen anal (18+), chastity
06:22

Sissy chastity training on tentacle

2 years ago

xHamster

train, dildo, tentacle, chastity
03:44

Latex Rubberdoll Ruined Orgasm In Chastity

3 years ago

HClips

latex, orgasm, chastity
07:12

Sissygasms in chastity

2 years ago

xHamster

train, chastity
04:38

Posting my chastity key goes wrong

1 year ago

xHamster

outdoor, lingerie, british, sissy, chastity
03:47

Bondex - Huge load of cum in chastity

6 years ago

xHamster

BDSM, chastity
32:59

Sissy in red lingerie locked onto her dildo stand with big black dildo

6 months ago

xHamster

black, small cock, fetish, bondage, dildo, crossdresser, sissy
21:19

Twin Game

11 months ago

xHamster

handjob, crossdresser, compilation, chastity
04:42

Sissy slut dressed in lingerie locked in chastity and playing with a big glass anal plug

1 year ago

xHamster

public, glasses, dress, chastity
14:39 67%

Sissy Emily Hardon Cheerleader Chastity Dildo Play

6 years ago

ShemaleZ

cheerleader, sissy, chastity
26:15

Naughty Chastity Sandy.

5 years ago

ShemaleZ

chastity
06:48

Anal Slut Chained to the Fuck Machine by Her Balls

10 months ago

xHamster

small cock, bondage, dildo, chastity, femboy
10:20

Sissy Anal Training And Sissygasm In Chastity Sc.7

2 years ago

ShemaleZ

train, sissy, chastity
05:15

SISSY SLUT SHOWS OFF AND PUSHES OUT BUTT PLUG

1 year ago

xHamster

pantyhose, teen (18+), teen anal (18+), crossdresser, sissy, chastity
03:24

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6 years ago

ShemaleZ

chastity
24:57

Chastity sandy loves black cocks

5 years ago

TXXX

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16:04

Sadie Rivers In A Chastity Cage Fucking Herself With A Blue Dildo 16 Min

2 years ago

ShemaleZ

dildo, redhead, tattoo, chastity
09:41

Slutty Trap Solo In Small Pink Chastity

8 months ago

HClips

amateur, chastity, stockings
08:40

Sissy In Leather Leotard And Chastity Takes Huge Dildo Up Her Ass

1 year ago

ShemaleZ

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06:12

Walking in chastity cage and buttplug

5 years ago

HClips

outdoor, chastity
05:07

Kinky Sissy

1 year ago

xHamster

panties, chastity
16:06

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

1 year ago

ShemaleZ

orgasm, BDSM, chastity, post op
10:44

Hubbys Keys And For This Orgasm Will Be Closed For 7 Days With A Chastity Belt

3 years ago

HClips

orgasm, chastity
03:41

Mina loves high heels and chastity cages.

4 years ago

xHamster

heels, chastity
05:39

Feminized Cosplay Slut Loves to be Fucked

2 years ago

xHamster

slut, JOI, cosplay, chastity
09:13

Sissy In Chastity arse pokeed

7 years ago

ShemaleZ

fetish, chastity
11:50

Cd Machine-fucked-in-chastity Whilst Sucking Tgirl Cock

3 years ago

ShemaleZ

machine, chastity
06:34

Sissy Rides Her Toy While Locked in Chastity

2 years ago

xHamster

pissing, chastity
02:41

Toilet Pee Sissy Faggot Wetting Pants Chastity

1 year ago

xHamster

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