TRANNY • CHASTITY 305 videos

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16:36

CarolineTV - Red head Self BDSM in chastity cage and nips clamps

1 week ago

PornHub

anal, chastity
16:06

Schoolgirl 18+ Crossdresser Desperately Tries To Cum Having A Chastity Cage (cum Replay In Slow-motion)

1 week ago

Upornia

18, chastity
22:15

Sissy cums in chastity while taking 12” dildo

3 weeks ago

PornHub

shemale, dildo, masturbation, chastity, solo
17:19

Public humiliation locked, plugged, gagged, clamped and squirt

3 weeks ago

xHamster

outdoor, chastity, BDSM, sissy, public
27:59

Sissy Maids Self Suspension Bondage in Chastity

1 month ago

xHamster

maid, bondage, BDSM, sissy
33:59

Trans Latex Hands Free Cum Chastity Fuck Piss Drinkung

1 month ago

ShemaleZ

shemale, hands free, chastity, latex
33:20

Trans Latex Hands Free Cum Piss Drinking Chastity Fuck Xxxsamanthaphd

1 month ago

ShemaleZ

shemale, pissing, chastity, latex
16:09

Easter special

1 month ago

xHamster

shemale, amateur, chastity, sissy, smoking
25:15

Francis Malice Sissy Dream 1

1 month ago

xHamster

big tits, shemale, german, solo, crossdresser
33:32

Skyler Storm Anal Masturbation in Chastity

1 month ago

PornHub

amateur, chastity
15:30

Glass Shower Door Dildo Fuck by Sissy Mindy

1 month ago

xHamster

crossdresser, sissy, shower
15:39

Chastity sissy

2 months ago

PornHub

solo, sissy, chastity
34:23

Trans Latex Hands Free Cum, Chastity Fuck, Piss Drinkung

2 months ago

PornHub

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

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

2 months ago

PornHub

chastity
25:04

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

2 months ago

xHamster

bondage, BDSM, sissy, chastity
19:03

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

3 months ago

xHamster

beauty, big ass, dildo, chastity, cum in ass, cum while fucked
30:39

Femboy chastity dildo riding!!

3 months ago

PornHub

chastity
18:11

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

3 months ago

PornHub

fetish, bondage, chastity
16:11

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

3 months ago

xHamster

riding, mexican, chastity
16:37

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

3 months ago

ShemaleZ

chastity, amateur
16:05

Chastity Orgasm by Sissy Mindy

3 months ago

xHamster

chastity
16:31

Sissy Chastity Cage and Dildo

3 months ago

PornHub

chastity
29:14 95%

Shemale Sub In Chastity Takes Bbc And Gets Cum Filled

4 months ago

ShemaleZ

amateur, shemale, interracial, lingerie, bareback, BBC, chastity
17:08

Caged Sissy Slut Rides BBC Dildo Sex Toy

4 months ago

xHamster

dildo, BBC, chastity
24:04

Lizz_ss25 changed sissy play

4 months ago

xHamster

chastity
29:14

Tiffany Doll - Sissy Schoolgirl In Chastity Bred Wit

4 months ago

ShemaleZ

interracial, sissy, chastity, stockings
25:26

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

5 months ago

ShemaleZ

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

Teen tranny fuck her ass with big dildo

5 months ago

xHamster

dildo, chastity
15:20

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

5 months ago

xHamster

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

Erika Oak Pumps Her Asshole

5 months ago

xHamster

dildo, chastity
29:34

Sissy Maid in Armbinder and Ankle Cuffed to bed in Chastity

5 months ago

xHamster

pantyhose, maid, chastity
35:21

Lizz_ss25 Slut vision anal steam

5 months ago

xHamster

chastity
32:38

Sissy Maid in Spiked Chastity Cage Cuffed to Bed Post

5 months ago

xHamster

maid, chastity
19:08 71%

Chastity Shemale Takes Interracial Anal Reaming And Creampie

6 months ago

ShemaleZ

creampie, anal, interracial, 18, bareback, chastity
15:03

Trap In Permanent Chastity And Extremely Aroused - Video 001

6 months ago

Upornia

chastity
20:03

Crossdressing Model Deep Anal Play First Sissygasm Sissy Chastity

6 months ago

ShemaleZ

teen anal (18+), BDSM, chastity
17:28

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

7 months ago

xHamster

cumshot, hands free, chastity, cum in ass
20:51

Sissy in chastity pounds pussy hard until she makes cummies

7 months ago

PornHub

teen (18+), BDSM, 18, chastity
26:40 82%

Chastity Caged No Hand Cum Compilation

8 months ago

ShemaleZ

stockings, BDSM, compilation, selfsuck, hands free, chastity
30:22

Sissy hole trainer ambersis every sissy must watch

8 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!

8 months ago

xHamster

pissing, squirt, crossdresser, chastity
15:54

Crossdresser On Live Webcam - Sissy Wears Chastity Belt

9 months ago

ShemaleZ

crossdresser, blonde, sissy, chastity
18:39

Spiked Chastity Cage Torment - Sissy Maids Self Bondage

9 months ago

xHamster

bondage, maid, BDSM, chastity
21:51

Self Suspension Bondage - Sissy Maid

9 months ago

xHamster

latex, bondage, maid, chastity
24:46

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

9 months ago

ShemaleZ

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

Mexican Sissy Maid un chastity Cage

10 months ago

xHamster

maid, mexican, chastity
16:06

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

10 months ago

ShemaleZ

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

Sissys Wooden Pony Ballet Boot Torment

10 months ago

xHamster

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

Sissy Maids Spiked Chastity Cage Self Bondage in New Boots

10 months ago

xHamster

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

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

10 months ago

xHamster

bondage, boots, maid, BDSM, chastity
16:12

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

11 months ago

xHamster

orgasm, chastity, post op
16:12

Another anal training

11 months ago

xHamster

chastity
21:23

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

11 months ago

xHamster

feet, dildo, chastity
40:19

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

11 months ago

Upornia

stockings, asian, chastity
17:17

Hardcore BBC Dildo destroys my ass, master has no mercy

11 months ago

xHamster

german, dildo, chastity
27:56

Random strangers abuse my asspussy

11 months ago

xHamster

german, stranger, chastity
15:25

In Chastity Cage And Butt Plug

11 months ago

ShemaleZ

chastity
25:11

Hi I'm Linzy19

11 months ago

xHamster

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

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

11 months ago

ShemaleZ

fisting, secretary, chastity
18:38

Sissy Lucy Being Locked Up In Metal Chastity For Locktober

11 months ago

ShemaleZ

latex, chastity
1:02:09

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

12 months ago

ShemaleZ

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

Sissygasm Challenge Day 2 - Femboy In Chastity Riding Dildo

12 months ago

ShemaleZ

chastity
53:38

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

1 year ago

ShemaleZ

latex, BBC, cosplay, chastity
31:05

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

1 year ago

ShemaleZ

dildo, chastity
19:11

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

1 year ago

PornHub

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

Sissy Secretary in horny after work activities

1 year ago

xHamster

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

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

1 year ago

ShemaleZ

clit, 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
25:50

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

1 year ago

xHamster

latex, mature anal, huge dildo, british, chastity
22:25

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

1 year 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
24:39

Sissy Luxiana In Chastity Cage And Dildo

1 year ago

ShemaleZ

dildo, chastity
16:45

Guy Jerks Off With Trans Woman In Chastity

1 year ago

ShemaleZ

jerking, chastity
40:39

Sissy In Red Nightie Fucks Her Ass While Locked In Chastity

1 year ago

ShemaleZ

chastity
18:53

Sissy boy smashed by fuckmachine

1 year ago

xHamster

chastity
16:33

Stranger controlls my machine

1 year ago

xHamster

machine, stranger, chastity
22:08

Fuckmachine torture

1 year ago

xHamster

chastity
1:00:38

Master fucking and fisting my ass with machine

1 year ago

xHamster

fisting, BDSM, machine, chastity
22:10

Sissy Maid Hogtied in Armbinder while in Steel Chastity Belt, Gagged

1 year ago

xHamster

latex, gagging, bondage, maid, chastity
20:12

Sissy Maid Cuffed Spread Eagle In Steel Chastity Belt And Huge Dildo

1 year ago

ShemaleZ

stockings, latex, huge dildo, maid, chastity
42:34

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

1 year ago

ShemaleZ

anal, double anal, group, cum in mouth, double penetration, chastity
16:12

Cd Sissy Trans Maschine Fucked Ass Pig Whore Chastity

1 year ago

ShemaleZ

latex, whore, chastity
25:47

Self Bondage in PVC Catsuit,Boots, Bra and Panties locked in chastity gagged

1 year ago

xHamster

gagging, bondage, boots, panties, chastity
20:35

White Sissy Chastity Training (fuck Machine)

1 year ago

ShemaleZ

train, BDSM, machine, sissy, chastity, solo
28:44

Exposed Cd Sissy Katie Does Live Show In Chastity Cage

1 year ago

ShemaleZ

chastity
24:36

Asian Femboy Tries Out The New Dildo With Chastity Cage

1 year ago

HClips

dildo, 18, chastity, femboy
28:27

Sissy Maid Strict Hogtie In Steel Chastity And Armbinder

1 year ago

Upornia

maid, chastity
21:53

Cumming in Chastity-Self Bondage Gasmask Suspension Harness

1 year ago

xHamster

latex, bondage, BDSM, chastity
23:15

Sissy Hope showing her boipussi and new tattoo

1 year ago

xHamster

mexican, chastity
28:27

Sissy Maid Strict Hogtie in Steel Chastity and Armbinder

1 year ago

xHamster

latex, bondage, maid, chastity
24:45

Astrid Apathy Puts On Erotic Show In Thigh High Socks And Chastity

1 year ago

ShemaleZ

socks, erotic, chastity
51:23

Linzy19's Guide To Chastity

1 year ago

xHamster

prostate, fetish, BDSM, domination, JOI, chastity
15:03 59%

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
15:51 88%

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

1 year ago

ShemaleZ

solo, sissy, chastity, BDSM
18:10

Trans Sissy Scarlet Sky Sissygasms All Over Herself in Chastity and Bondage!

1 year ago

PornHub

anal, orgasm, bondage, blonde, goth, chastity
17:38

Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots

1 year ago

xHamster

latex, huge dildo, bondage, boots, maid, lingerie, BDSM
16:12

CD Sissy Trans Maschine Fucked Ass Pig Whore Chastity

1 year ago

xHamster

whore, chastity
20:12

Sissy Maid Cuffed Spread Eagle in Steel Chastity Belt and Huge Dildo

1 year ago

xHamster

latex, huge dildo, fetish, maid, chastity
15:06

Skitty in Soft slapping into Hard Sissygasm

1 year ago

xHamster

latex, german, chastity
17:59

Spiked Chastity Cage Self Bondage Sissy Maid

1 year ago

xHamster

latex, bondage, maid, chastity
20:26 79%

Sissy In Chastity Pounds Pussy Hard Until She Makes Cummies

1 year ago

ShemaleZ

amateur, webcam, sissy, chastity
18:05

БДСМ, госпожа играет с членом трансика

1 year ago

PornHub

train, fetish, bondage, chastity
23:54

Sissy Chastity 10/12/2022 Transgender Slave Obedience Lock Up Metal Cage

1 year ago

ShemaleZ

chastity
18:33

Self Bondage In Pvc Layers Steel Chastity Belt And Large Dildo Locked

1 year ago

TXXX

latex, bondage, chastity
21:30

Sissy Fisting Ass Hard in Chastity

1 year ago

xHamster

mature, fisting, chastity
16:04

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

1 year ago

ShemaleZ

dildo, redhead, tattoo, chastity
24:37

Skitty in Anal Plug progression Stretching

1 year ago

xHamster

german, train, chastity
1:39:12

Tgirl_fun 2022-2-7 Chaturbate Stream

1 year ago

PornHub

bondage, BDSM, tied, chastity
18:33

Self Bondage in PVC Layers, Steel Chastity Belt and Large Dildo Locked

1 year ago

xHamster

latex, bondage, chastity

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