TRANNY • CHASTITY 325 videos

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18:38

Sissy Lucy Being Locked Up In Metal Chastity For Locktober

1 year ago

ShemaleZ

latex, chastity, sissy
23:33

Pink Mercy trap in chastity doing deepthroath and anal play

5 years ago

TXXX

chastity
33:18

She Let Him Out Of Chastity

5 years ago

TXXX

chastity
16:37

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

10 months ago

ShemaleZ

chastity, amateur
15:25

In Chastity Cage And Butt Plug

1 year ago

ShemaleZ

chastity
47:08

Armbinder Tied To Chastity Cage Sissy Maid Self Bondage

2 years ago

ShemaleZ

latex, bondage, maid, tied, chastity
53:38

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

1 year ago

ShemaleZ

latex, BBC, cosplay, chastity, interracial
20:09

Chastity Slut using vibrator and came

5 years ago

TXXX

vibrator, slut, chastity
25:27

Sexy Chastity

6 years ago

ShemaleZ

chastity
16:12

Cd Sissy Trans Maschine Fucked Ass Pig Whore Chastity

1 year ago

ShemaleZ

latex, whore, chastity
21:33

Sissy in Chastity Pleasures Herself with Toys and Hypno

5 years ago

ShemaleZ

fisting, chastity
23:29

Sissy Cd In Chastity Milked Dry Handsfree Sissygasms Huge Dildos Big Mess Cleanup Rainbow Sto

3 years ago

HClips

huge dildo, milk, hands free, chastity
1:02:09

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

1 year ago

ShemaleZ

mature anal, huge dildo, pegging, chastity, latex
34:42

Sissy Maid Chained To Bed In Chastity, Gagged And Leather Bondage Mitts Handcuffed On

2 years ago

ShemaleZ

gagging, bondage, maid, leather, chastity
15:03

Trap In Permanent Chastity And Extremely Aroused - Video 001

1 year ago

Upornia

chastity
19:06

Sissy Femboy In Chastity Taking Big Dildos In Her Ass And Trying And Sissygasm

2 years ago

HClips

chastity
22:25

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

1 year ago

HClips

femdom, chastity
28:44

Exposed Cd Sissy Katie Does Live Show In Chastity Cage

1 year ago

ShemaleZ

chastity
21:54

Sissy Cd Riding Bbc Dildos Chastity Cum

2 years ago

Upornia

chastity
17:16

Pink sissy has multiple sissygasms in chastity.

5 years ago

ShemaleZ

chastity
16:02

Ezzyforever Ruins Her Ass And Cums In Chastity

3 years ago

Upornia

fetish, chastity, cum in ass
22:36

Trans Girl In Chastity Rides Dildo Ft. Animalauren

2 years ago

ShemaleZ

dildo, riding, chastity
21:44

Kinky Kigarumi Chastity

2 years ago

ShemaleZ

latex, chastity
34:40

Chastity Michaels Is A black ladyman Who Likes To pound

5 years ago

ShemaleZ

ebony, black, interracial, chastity
23:54

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

2 years ago

ShemaleZ

chastity, sissy
28:19

Pink sissy rides again. Sissygasm in chastity like a good gurl

5 years ago

ShemaleZ

chastity
24:39

Sissy Luxiana In Chastity Cage And Dildo

1 year ago

ShemaleZ

dildo, chastity
15:34

Taking my biggest dildos with my new small chastity cage on

5 years ago

ShemaleZ

chastity
39:38

Sissy cums in khd x3 espresso chastity cage fucks BBC with her anal cunt

5 years ago

HClips

BBC, chastity
24:31

Sissy In Chastity Caged Fuck Dildo

3 years ago

HClips

dildo, chastity
25:39

Sissy In Corset Rub Herself With Dildo And Rabbit Then Cum In Chastity

3 years ago

Upornia

fetish, dildo, chastity
21:33

Sissygasm Challenge Day 2 - Femboy In Chastity Riding Dildo

1 year ago

ShemaleZ

chastity
21:30

Sissy Fisting Ass Hard In Chastity

1 year ago

ShemaleZ

fisting, chastity, sissy
21:18

Armbinder Hogtie In Pvc Catsuit And Steel Chastity Belt

2 years ago

HClips

latex, chastity
29:15

Daddys Little Sissy hoe Erin Showing Her recent Chastity

5 years ago

TXXX

chastity
22:10

Sissy Maid Hogtied In Armbinder While In Steel Chastity Belt Gagged

1 year ago

Upornia

gagging, maid, chastity
20:39

Femboy Havin Some Dildo Fun In Chastity Cage

2 years ago

Upornia

chastity
18:33

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

2 years ago

TXXX

latex, bondage, chastity
21:05

Sissy Daily Basics: Some Anal Fun In Chastity

3 years ago

HClips

chastity, brunette
28:27

Sissy Maid Strict Hogtie In Steel Chastity And Armbinder

1 year ago

Upornia

maid, chastity
18:51

Sissy teen In Chastity pounding Dildos

5 years ago

ShemaleZ

chastity
19:08

Self Bondage Armbinder Hogtie In Pvc Catsuit And Lycra Bodysuit With Chastity Belt And Dildo Locked In Place

2 years ago

TXXX

latex, bondage, spandex, chastity
19:31

Long anal Plug with Chastity cum

5 years ago

ShemaleZ

chastity
17:12

Sissy cd cums in chastity with vibrator after riding fucking machine (2/2)

5 years ago

TXXX

machine, vibrator, chastity
18:56

Trans Sissy Slut Performs For Horny Men On Cam: Anal Chastity Camshow

3 years ago

ShemaleZ

slut, chastity
22:03 45%

Chastity Sub Sprays Ruined Orgasm Everywhere

4 months ago

PornHub

amateur, feet, POV, fetish, cumshot, chastity
18:54

Kinky Trans Domme Gives You Pov Humiliation. Chastity Feet Girl Dick Verbal Degradation

5 months ago

HClips

feet, amateur
15:07

Erica Cherry And Queenie Sateen In Submissive With Chastity Cage Makes Femdom Squirt A

2 months ago

ShemaleZ

blonde, femdom, chastity, shemale, squirt
18:50 41%

Sissy Long Term Chastity

6 years ago

xHamster

POV, sissy, chastity, shemale fucks guy
24:21

Sissy cd chastity self teasing & lots of anal toys (edited version)

5 years ago

ShemaleZ

tease, chastity
17:19

Public humiliation locked, plugged, gagged, clamped and squirt

7 months ago

xHamster

outdoor, chastity, BDSM, sissy, public, fetish
17:37

Chastity guide : A review of all metal chastity cages by sissy joyce

3 months ago

PornHub

sissy, amateur, chastity, shemale
16:39 66%

Trans girl in chastity plays with dildos and fists herself

2 years ago

xHamster

cute, teen anal (18+), fisting, solo, 18, chastity
21:23 81%

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

1 year ago

xHamster

feet, dildo, chastity, solo
15:39

Sissy playing with dildo until cumming

3 months ago

xHamster

dildo, solo, crossdresser, sissy, chastity, finnish
22:21

Smokin hot trans chick has anal orgasm while in chastity

5 months ago

PornHub

amateur, orgasm, bondage, solo, masturbation, anal orgasm, chastity
1:03:39 71%

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 1

1 year ago

xHamster

stockings, french, lingerie, chastity, sissy
1:39:12 53%

Tgirl_fun 2022-2-7 Chaturbate Stream

2 years ago

PornHub

bondage, BDSM, tied, chastity
17:41 67%

Dirty priest tied up and humiliated her slave

4 years ago

xHamster

femdom, russian, bondage, BDSM, tied, chastity
19:03 93%

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

9 months ago

xHamster

beauty, anal, big ass, dildo, big cock, chastity, cum while fucked
22:55 43%

Sissy Secretary in horny after work activities

1 year ago

xHamster

stockings, clit, secretary, nylon, sissy, chastity
33:24 71%

Sissys Wooden Pony Ballet Boot Torment

1 year ago

xHamster

latex, fetish, bondage, boots, lingerie, BDSM, chastity
25:04

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

9 months ago

xHamster

bondage, BDSM, sissy, chastity
1:15:02

Pain and pleasure, chastity and lust, Part 2

3 years ago

xHamster

german, BDSM, JOI, chastity
20:04

Shemale samurai challenges you to take her chastity

5 years ago

PornHub

toys, cosplay, chastity, solo
28:47 62%

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

2 years ago

xHamster

bondage, chastity, post op
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
24:42

Crossdresser gets machine fucked with XXL Monster Dildos #5

4 months ago

xHamster

german, dildo, crossdresser, hardcore, chastity
49:33

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 2

1 year ago

xHamster

french, chastity
18:10

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

1 year ago

PornHub

anal, orgasm, bondage, blonde, goth, chastity
20:08

Sissy Maid Self Bondage in Spiked Chastity Cage

2 years ago

xHamster

latex, bondage, maid, chastity
21:19

Twin Game

4 months ago

xHamster

handjob, crossdresser, compilation, chastity
16:05

Mexican Sissy Maid un chastity Cage

1 year ago

xHamster

maid, mexican, chastity
1:08:51

Sissy slut in lingerie anal fuck on sex machine with squirting in chastity cage! Good little femboy beta cuck slave!

1 year ago

xHamster

pissing, squirt, crossdresser, chastity
51:23

Linzy19's Guide To Chastity

1 year ago

xHamster

prostate, fetish, BDSM, domination, JOI, chastity
32:07

Chatty crossdresser tries out new depth - 2023-02-23 - part 2 - uncharted territory

1 year ago

xHamster

french, chastity
15:20

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

11 months ago

xHamster

stockings, thai, masturbation, skirt, chastity, femboy
27:23

Sissy Training: Deepthroat, anal & Sissygasm while locked in Chastity

2 years ago

PornHub

stockings, dildo, panties, dress, thong, chastity
19:06

Sissy in chastity swallow cum

9 years ago

xHamster

latex, swallow, sissy, chastity
54:03 45%

Batman CosPlay Parody with BBC Batman, Chastity Sissy BatGirl and Latex Hit Girl

4 years ago

PornHub

latex, heels, BBC, cosplay, chastity
21:26 76%

Chastity estim cum for cute sissy

3 years ago

xHamster

cute, orgasm, BDSM, crossdresser, chastity
18:39

Spiked Chastity Cage Torment - Sissy Maids Self Bondage

1 year ago

xHamster

bondage, maid, BDSM, chastity
17:28

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

1 year ago

xHamster

cumshot, hands free, chastity, cum in ass
15:06

Skitty in Soft slapping into Hard Sissygasm

2 years ago

xHamster

latex, german, chastity
1:02:31 48%

Lisa and TGirl Lucy anal training and chastity

3 years ago

PornHub

mature, stockings, mature anal, train, fetish, double anal, crossdresser
30:22

Sissy hole trainer ambersis every sissy must watch

1 year ago

PornHub

femdom, chastity
16:51 70%

Cute pink haired trans woman masturbating in chastity

2 years ago

xHamster

cute, dildo, BDSM, anime, chastity, solo
25:24

Sissy fucked by bbc machine, rnd guy fucks me soo good

2 years ago

xHamster

dildo, machine, skinny, chastity
20:21

Gorgeous Shemale Fingering Herself in Chastity

2 years ago

xHamster

18, chastity
21:22 73%

Skitty&M&L in Our first fun Together

2 years ago

xHamster

latex, german, BDSM, sissy, chastity
16:12

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

1 year ago

xHamster

orgasm, chastity, post op
15:29

Pee tasting and chastity masturbation of a kinky latexdoll

2 years ago

xHamster

pissing, latex, chastity
1:00:38

Master fucking and fisting my ass with machine

1 year ago

xHamster

fisting, BDSM, machine, chastity
26:00

Selfbondage latex - Chastity, nose mask p2

2 years ago

xHamster

latex, french, heels, mask, chastity
23:17

Painful ponyplay on the Halloween party

4 years ago

xHamster

femdom, train, party, russian, BDSM, small tits, hardcore
22:15

Sissy cums in chastity while taking 12” dildo

7 months ago

PornHub

shemale, dildo, masturbation, chastity, solo
16:31

Sissy Chastity Cage and Dildo

10 months ago

PornHub

chastity, dildo
19:00

Sissy Lucy being locked in metal Chastity for Locktober

4 years ago

xHamster

couple, BDSM, 18, chastity
37:50 61%

CD in Pink Corset and chastity, nipple clamps,spanking, sucking, playing and teasing

2 years ago

xHamster

mature, tease, BDSM, spanking, nipples, chastity
21:53

Cumming in Chastity-Self Bondage Gasmask Suspension Harness

1 year ago

xHamster

latex, bondage, BDSM, chastity
32:38

Sissy Maid in Spiked Chastity Cage Cuffed to Bed Post

1 year ago

xHamster

maid, chastity
19:11

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

1 year ago

PornHub

femdom, latex, bondage, BDSM, spanking, pegging, chastity
20:12

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

2 years ago

xHamster

latex, huge dildo, fetish, maid, chastity
17:39

Transsexual blonde gets blowjob in bed from guy before fucks

2 years ago

xHamster

couple, teen anal (18+), chastity, teen (18+)
21:51

Teen tranny fuck her ass with big dildo

11 months ago

xHamster

dildo, chastity
20:51

Sissy in chastity pounds pussy hard until she makes cummies

1 year ago

PornHub

teen (18+), BDSM, 18, chastity
26:44

Hot Chastity Sandy.

12 years ago

xHamster

chastity
16:12

Another anal training

1 year ago

xHamster

chastity
21:51

Self Suspension Bondage - Sissy Maid

1 year ago

xHamster

latex, bondage, maid, chastity
18:51

Latexa creature in chastity cage

8 years ago

xHamster

latex, chastity
18:52

Sissy Hope great, hot and private compilation moments.

4 months ago

xHamster

small cock, latina, compilation, big cock, mexican, sissy, chastity
24:04

Lizz_ss25 changed sissy play

11 months ago

xHamster

chastity
16:14

Crossdresser gets machine fucked with XXL Monster Dildos #9

4 months ago

xHamster

german, crossdresser, machine, skinny, chastity, femboy
25:01

Crossdresser fuck dildo with chastity cage

3 years ago

xHamster

dildo, chastity
49:11

Podcast Ep13: Sissy, Chastity and Lust

4 years ago

xHamster

chastity
16:05

Chastity Orgasm by Sissy Mindy

10 months ago

xHamster

chastity
25:00

Black Tranny Jizz Jam - Episode 1

3 months ago

xHamster

black, big cock, shemale, chastity
24:37

Skitty in Anal Plug progression Stretching

2 years ago

xHamster

german, train, chastity
22:39

Sissy in chastity pushing bananas in and out of her boipussy

6 months ago

xHamster

pantyhose, stockings, mexican, asshole, chastity
32:11

Lizzy Yum August 2022 #8 SEX MACHINES, EROTIC ELECTRICITY & BSDM-CHASTITY

2 years ago

xHamster

mature, mature anal, BDSM, erotic, machine, chastity

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