TRANNY • CHASTITY 295 videos

Popular Latest Top rated

32:59

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

8 months ago

xHamster

black, small cock, fetish, bondage, dildo, sissy, chastity
31:05

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

2 years ago

ShemaleZ

dildo, chastity, femboy, sissy
16:14

Crossdresser gets machine fucked with XXL Monster Dildos #9

1 year ago

xHamster

german, crossdresser, machine, skinny, chastity, femboy
49:11

Podcast Ep13: Sissy, Chastity and Lust

5 years ago

xHamster

chastity
17:39

Transsexual blonde gets blowjob in bed from guy before fucks

3 years ago

xHamster

couple, teen anal (18+), chastity, teen (18+)
20:12

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

2 years ago

xHamster

latex, huge dildo, fetish, maid, chastity
26:44

Hot Chastity Sandy.

12 years ago

xHamster

chastity
24:11

Asian Femboy In Cheongsam Tries Out The New Horsecock Dildo With Chastity Cage Cums 3 Times

4 years ago

ShemaleZ

chastity
30:27

Rianna James In Cuckold Fantasy, Chastity, Small Penis Humiliation

3 years ago

ShemaleZ

cuckold, tattoo, penis, chastity, brunette
18:52

Sissy Hope great, hot and private compilation moments.

1 year ago

xHamster

small cock, latina, compilation, big cock, mexican, sissy, chastity
22:10 73%

Slutty Trap Girl Really Enjoys Her Dildos And Chastity 2/5

6 months ago

HClips

chastity, shemale, amateur, dildo, shemale and girl, solo
23:19

Ghotic trap solo in chastity

6 years ago

ShemaleZ

chastity
22:14

Fuck me in chastity device

8 years ago

TXXX

latex, chastity
1:17:37

Yasmin Lee, Chastity, And Alissa Gangbang Guy

4 years ago

Upornia

gangbang, group, chastity
24:46

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

2 years ago

ShemaleZ

femdom, BDSM, BBC, chastity, sissy
24:45

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

2 years ago

ShemaleZ

socks, erotic, chastity
15:27

Frilly sissy in chastity fucked by Mistress

6 years ago

ShemaleZ

femdom, chastity
26:45

Naughty Chastity Sandy.

7 years ago

ShemaleZ

chastity
40:39

Sissy In Red Nightie Fucks Her Ass While Locked In Chastity

2 years ago

ShemaleZ

chastity
54:08

Chastity Cage - Pandora Melanie

7 months ago

ShemaleZ

creampie, threesome, brazil, BDSM, tattoo, double anal, double penetration
15:08

Chastity and plug

4 years ago

xHamster

chastity
19:06

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

3 years ago

HClips

chastity
16:11

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

1 year ago

xHamster

riding, mexican, chastity
21:51

Self Suspension Bondage - Sissy Maid

1 year ago

xHamster

latex, bondage, maid, chastity
25:01

Crossdresser fuck dildo with chastity cage

4 years ago

xHamster

dildo, 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
20:03

Crossdressing Model Deep Anal Play First Sissygasm Sissy Chastity

1 year ago

ShemaleZ

teen anal (18+), BDSM, chastity
24:37

Skitty in Anal Plug progression Stretching

2 years ago

xHamster

german, train, chastity
15:45

Sissy In Chastity Pounding Creampie Fuckmachine

3 years ago

ShemaleZ

chastity, sissy, creampie
19:06

Sissy in chastity swallow cum

7 years ago

ShemaleZ

swallow, chastity
53:05

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

2 years ago

xHamster

orgasm, bondage, chastity, post op
16:37

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

1 year ago

ShemaleZ

chastity, amateur
17:39

Lily Star In Ass To Mouth And Leaking Out Of Chastity

3 years ago

ShemaleZ

ass to mouth, chastity, brunette
26:38

Trans anal Of Chastity Sandy

5 years ago

TXXX

chastity
22:39

Sissy in chastity pushing bananas in and out of her boipussy

1 year ago

xHamster

pantyhose, stockings, mexican, asshole, chastity
21:30

Sissy Fisting Ass Hard in Chastity

2 years ago

xHamster

mature, fisting, chastity, solo
1:01:40 60%

Gorgeous Hands Free Cum

7 years ago

ShemaleZ

hands free, chastity, creampie compilation, solo
29:47

Daddys Little Sissy hoe Erin Showing Her recent Chastity

7 years ago

ShemaleZ

BDSM, chastity
19:40

Shemale samurai challenges you to take her chastity

6 years ago

ShemaleZ

toys, chastity
18:25

Plastic shemale whore in chastity rides huge dildos

5 years ago

TXXX

huge dildo, fetish, dildo, riding, whore, chastity
27:08

Trans Anal Of Chastity Sandy

9 years ago

TXXX

chastity
24:04

Lizz_ss25 changed sissy play

1 year ago

xHamster

chastity
33:48

She Let Him Out Of Chastity

6 years ago

ShemaleZ

chastity
25:26

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

1 year ago

ShemaleZ

POV, ladyboy, shemale and girl, cum in mouth, chastity, femboy
33:50

She Let Him Out Of Chastity

7 years ago

ShemaleZ

chastity
19:57

Sissy Joy pounded By Her mistresse With A thong On while Locked In Chastity

7 years ago

ShemaleZ

femdom, thong, chastity
24:36

Asian Femboy Tries Out The New Dildo With Chastity Cage

2 years ago

HClips

dildo, 18, chastity, femboy, asian
33:20

Trans Latex Hands Free Cum Piss Drinking Chastity Fuck Xxxsamanthaphd

1 year ago

ShemaleZ

shemale, pissing, chastity, latex
33:18

She Let Him Out Of Chastity

5 years ago

ShemaleZ

blowjob, chastity
18:33

DEBBIE IN CHASTITY

5 years ago

ShemaleZ

chastity
15:39

Sissy Oksana Is Closed In Chastity And Wants To Have An Anal

3 years ago

ShemaleZ

chastity
15:15

Ashley gets punished for removeing her chastity part 2 out of 3

6 years ago

ShemaleZ

chastity
15:25

In Chastity Cage And Butt Plug

2 years ago

ShemaleZ

chastity
16:00

In chastity and lingerie playing with my ass

6 years ago

xHamster

chastity
34:40

Chastity Michaels Is A black ladyman Who Likes To pound

6 years ago

ShemaleZ

ebony, black, interracial, chastity
16:12

Cd Sissy Trans Maschine Fucked Ass Pig Whore Chastity

2 years ago

ShemaleZ

latex, whore, chastity
17:08

Caged Sissy Slut Rides BBC Dildo Sex Toy

1 year ago

xHamster

dildo, BBC, chastity
28:18

Sissy Maids Self Bondage Armbinder and Chastity Belt

3 years ago

xHamster

latex, bondage, maid, chastity
20:09

Chastity Slut using vibrator and came

5 years ago

TXXX

vibrator, slut, chastity
27:49

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

2 years ago

ShemaleZ

fisting, secretary, chastity
21:40

New Deep Love Vol.1 - Episode 5

2 years ago

xHamster

chastity
29:45

Daddy s little sissy slut erin showing her new chastity

8 years ago

TXXX

slut, chastity
16:58

Ruined Orgasm In Chastity And Cbt For Lana Trap

3 years ago

ShemaleZ

teen (18+), fetish, orgasm, BDSM, shemale and girl, toys, domination
20:23

Sandy solo

5 years ago

ShemaleZ

solo, chastity
17:12

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

2 years ago

ShemaleZ

clit, chastity, big clit
36:55

Chastity boy puts together office chair in ballet heels

6 years ago

ShemaleZ

office, heels, chastity
29:34

Sissy Maid in Armbinder and Ankle Cuffed to bed in Chastity

1 year ago

xHamster

pantyhose, maid, chastity, crossdresser
16:05

Chastity Orgasm by Sissy Mindy

1 year ago

xHamster

chastity
20:15

Sissy Maids Bathroom Bondage, Locked to Toilet

3 years ago

xHamster

toilet, latex, bondage, maid, bathroom, chastity
15:07

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

10 months ago

ShemaleZ

blonde, femdom, chastity, shemale, squirt
18:24

Sissy Maids Spiked Chastity Cage Self Bondage in New Boots

2 years ago

xHamster

bondage, boots, maid, JOI, chastity
33:18

She Let Him Out Of Chastity

5 years ago

TXXX

chastity
16:06

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

1 year ago

Upornia

18, chastity, crossdresser
25:50

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

2 years ago

xHamster

latex, mature anal, huge dildo, british, chastity
18:24

Diamond Chastity - Motel Fun

3 years ago

ShemaleZ

hotel, chastity, brunette
17:11

Guy Jerks Off with Trans Woman in Chastity

2 years ago

xHamster

fetish, 18, jerking, chastity
22:08

Fuckmachine torture

2 years ago

xHamster

chastity
57:56

Sissy Lucys Toy Time In Chastity

4 years ago

HClips

chastity
15:03

Trap In Permanent Chastity And Extremely Aroused - Video 001

1 year ago

Upornia

chastity
23:33

Pink Mercy trap in chastity doing deepthroath and anal play

6 years ago

TXXX

chastity
27:05

Sissy Latexdoll Is Wearing Chastity

3 years ago

Upornia

chastity
33:59

Trans Latex Hands Free Cum Chastity Fuck Piss Drinkung

1 year ago

ShemaleZ

shemale, hands free, chastity, latex
26:49

Spiked Chastity Cage Self Bondage

3 years ago

xHamster

latex, huge dildo, bondage, chastity
27:08

Trans Anal Of Chastity Sandy

7 years ago

ShemaleZ

chastity
21:33

Sissy in Chastity Pleasures Herself with Toys and Hypno

5 years ago

ShemaleZ

fisting, chastity
17:39

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

1 year ago

xHamster

chastity, sissy, fetish, toys
35:21

Lizz_ss25 Slut vision anal steam

1 year ago

xHamster

chastity
18:38

Sissy Lucy Being Locked Up In Metal Chastity For Locktober

2 years ago

ShemaleZ

latex, chastity, sissy
20:12

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

2 years ago

ShemaleZ

stockings, latex, huge dildo, maid, chastity
36:02

Crossdresser gets machine fucked with XXL Monster Dildos #2

1 year ago

xHamster

german, dildo, lingerie, crossdresser, monster, chastity
21:33

Sissygasm Challenge Day 2 - Femboy In Chastity Riding Dildo

2 years ago

ShemaleZ

chastity
53:38

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

2 years ago

ShemaleZ

latex, BBC, cosplay, chastity, interracial
47:08

Armbinder Tied To Chastity Cage Sissy Maid Self Bondage

2 years ago

ShemaleZ

latex, bondage, maid, tied, chastity
41:54

Sissy femboy in chastity cage ballbusts to hands free orgasm

1 year ago

xHamster

masturbation, chastity, BDSM
24:52

Chastity Sandy likes dark penises

5 years ago

ShemaleZ

chastity
21:44

Kinky Kigarumi Chastity

3 years ago

ShemaleZ

latex, chastity
23:29

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

4 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

2 years ago

ShemaleZ

mature anal, huge dildo, pegging, chastity, latex
24:31

Sissy In Chastity Caged Fuck Dildo

4 years ago

HClips

dildo, chastity
22:36

Trans Girl In Chastity Rides Dildo Ft. Animalauren

3 years ago

ShemaleZ

dildo, riding, chastity
15:26

Sissy Maid Cums in Chastity and in Bondage and Swallows Her Sissy Cum

6 months ago

xHamster

sissy, crossdresser, hands free, bondage, chastity, swallow
34:42

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

3 years ago

ShemaleZ

gagging, bondage, maid, leather, chastity
31:40

Sissy Maid Rides Her Sex Doll and Gets Chained Onto It

6 months ago

xHamster

riding, sissy, chastity, solo, crossdresser, maid
20:49

Sissy Maids Bed Bondage

3 years ago

xHamster

bondage, maid, chastity
46:39

Sissy Maid Self Bondage Armbinder Hogtied

3 years ago

xHamster

latex, bondage, maid, chastity
23:15

Sissy Hope showing her boipussi and new tattoo

2 years ago

xHamster

mexican, chastity
18:33

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

2 years ago

xHamster

latex, bondage, chastity
27:31

Self Suspension Bondage - Sissy Maid

1 year ago

xHamster

latex, chastity, crossdresser, sissy, bondage
21:22

Sissy Maid Caught in Self Bondage

4 years ago

xHamster

couple, bondage, maid, caught, chastity
52:59

Lizzy Yum In April 2023-welcome Home Lizzy-bdsm Female Chastity Post Op Pussy Masturbation

3 months ago

HClips

BDSM, shemale, solo, chastity, post op
17:20

Dirty slut

3 years ago

xHamster

french, hooker, slut, chastity
27:42

Training her ass for big thick cocks

3 years ago

xHamster

train, chastity
19:27

Suspension Self Bondage Sissy Maid in Chastity, Gagged and Blindfolded

2 years ago

xHamster

latex, gagging, bondage, maid, chastity
27:05

Sissy latexdoll is wearing chastity

3 years ago

xHamster

rubber, JOI, chastity
21:18

Armbinder Hogtie in PVC catsuit and Steel Chastity Belt

3 years ago

xHamster

latex, bondage, maid, chastity
16:33

Stranger controlls my machine

2 years ago

xHamster

machine, stranger, chastity, BDSM
28:19

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

6 years ago

ShemaleZ

chastity
17:16

Pink sissy has multiple sissygasms in chastity.

5 years ago

ShemaleZ

chastity
22:25

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

2 years ago

HClips

femdom, chastity
19:31

Slim sissy in chastity fucks her smooth ass.

4 years ago

xHamster

ass, JOI, chastity

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