TRANNY • CHASTITY 2,286 videos

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03:47

Ts In Chastity Fucked Cowgirl Raw

1 year ago

ShemaleZ

chastity
08:54

Hot Tgirl In Chastity Deepthroats Huge Dick

1 year ago

ShemaleZ

chastity
03:09

Big Ass Trans Woman Fucked In Chastity

1 year ago

Upornia

chastity
03:32

Hot Trans Woman In Chastity Deepthroats Huge Dick

1 year ago

Upornia

chastity
03:52

Big Ass Tgirl In Chastity Fucked Doggystyle

1 year ago

Upornia

chastity
03:40 87%

Sissys in chastity

4 years ago

xHamster

latex, chastity, sissy
02:34 72%

SISSIES IN CHASTITY

4 years ago

xHamster

amateur, sissy, chastity
02:12 79%

Leaking alot caged

1 year ago

xHamster

teen (18+), hands free, chastity, sissy
14:37 86%

The church of Hentai

1 year ago

PornHub

homemade, stockings, boots, nun, cosplay, chastity
09:44 69%

Together in a life of chastity

3 months ago

xHamster

beauty, POV, muscle, dildo, solo, chastity
12:23

Chastity locked sissy squirting on a dildo while thinking about her daddy

2 months ago

xHamster

pissing, stockings, prostate, dildo, solo, sissy, chastity
18:50 41%

Sissy Long Term Chastity

6 years ago

xHamster

POV, sissy, chastity, shemale fucks guy
12:24 73%

TGirl Lucy in Chastity is fucked by 10 inch BBC at SheWorld

4 years ago

xHamster

interracial, BBC, chastity
22:03 45%

Chastity Sub Sprays Ruined Orgasm Everywhere

4 months ago

PornHub

amateur, feet, POV, fetish, cumshot, chastity
06:34

My games in a black dress and high heels

2 months ago

xHamster

chastity, amateur, crossdresser, sissy, black, russian
17:37

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

3 months ago

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sissy, amateur, chastity, shemale
07:05

Locked In Chastity Under My Pretty Pink Dress

8 months ago

PornHub

fetish, dress, small tits, chastity
15:39

Sissy playing with dildo until cumming

2 months ago

xHamster

dildo, solo, crossdresser, sissy, chastity, finnish
08:52

Luxia_tv, submissive and with the chastity cage

5 months ago

xHamster

mature anal, spanish, crossdresser, sissy, chastity
08:12

Chastity in Chastity Day 6 Reward

2 months ago

xHamster

amateur, chastity, JOI
01:59

Sissy in chastity fucked by BBC

6 years ago

xHamster

chastity
08:24

My full frustrating chastity journey (trans girl)

8 months ago

PornHub

cosplay, chastity, bondage, shemale and girl
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
05:38

Trans cums so hard in chastity while fucking her hole

7 months ago

PornHub

amateur, chastity, solo, feet, cum while fucked
11:39 74%

Squeezing a penis into a micro cage

2 years ago

PornHub

train, insertion, penis, chastity
13:34 83%

Real sissy full in chastity

9 years ago

xHamster

BDSM, full movie, toys, chastity, sissy
17:19

Public humiliation locked, plugged, gagged, clamped and squirt

7 months ago

xHamster

outdoor, chastity, BDSM, sissy, public, fetish
05:37

Chastity Femboy Public Buttplug Walk & Anal Orgasms in The Woods Multiple Cumshots

3 months ago

xHamster

beauty, public, dildo, anal orgasm, chastity
04:42 69%

PorchaeTS tries new homemade chastity Dick dildo to pleasure the Mrs. Total mind trip.

1 year ago

xHamster

huge dildo, fetish, chastity
1:39:12 53%

Tgirl_fun 2022-2-7 Chaturbate Stream

2 years ago

PornHub

bondage, BDSM, tied, chastity
07:52

Sissy Holy - Chastity Masturbation Instructions - how I play with myself

3 months ago

xHamster

mature, beauty, BDSM, ladyboy, sissy, 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
05:12

MaureenNadh - Tied Up Dildo Riding, Locked In Micro Chastity

8 months ago

xHamster

dildo, tied, skinny, chastity, riding
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
22:21

Smokin hot trans chick has anal orgasm while in chastity

4 months ago

PornHub

amateur, orgasm, bondage, solo, masturbation, anal orgasm, chastity
10:04

Caged sissy rides pink dildo with anal orgasms

5 months ago

xHamster

stockings, prostate, dildo, crossdresser, anal orgasm, chastity
05:22

Pathetic Sluts Need to be Filled with Cock & Always Keep Their Clittys Locked!

3 months ago

xHamster

sissy, chastity
05:58 40%

Sissy in chastity cage wants to fuck

1 year ago

xHamster

italian, crossdresser, chastity, solo
17:41 67%

Dirty priest tied up and humiliated her slave

4 years ago

xHamster

femdom, russian, bondage, BDSM, tied, chastity
02:10

QoS Transsexual Maid in Chastity - 4K Edition Preview

4 years ago

xHamster

maid, chastity, solo
09:51 72%

Crossdresser nun in chastity pleases daddy

5 years ago

xHamster

couple, crossdresser, nun, toys, domination, chastity
07:10

Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum

7 months ago

PornHub

amateur, anal, cumshot, machine, sissy, hands free, chastity
10:05 87%

Sexy Blonde Sissy Bailey Wilde in Chastity Fucked

9 months ago

xHamster

amateur, crossdresser, sissy, chastity, femboy, cum in ass
07:26 44%

Sissy clitty chastity

4 years ago

xHamster

sissy, chastity
09:39 73%

Sissy Candy in black lingerie and chastity is locked and impaled on her dildo stand

3 months ago

xHamster

black, fetish, bondage, dildo, lingerie, crossdresser, sissy
08:10

Anal sex with sissymaid Kitsy in chastity and bunny ears

2 years ago

xHamster

chastity
05:15 64%

Chastity & Ass to mouth with BIG black cock

2 years ago

xHamster

black, small cock, ass to mouth, BBC, chastity
04:26 86%

VERY HOT Blonde Crossdresser in Chastity Fucked Doggy Style

10 months ago

xHamster

amateur, crossdresser, 18, sissy, chastity, femboy
03:09 88%

AB085 Lustful Abby Kitty be Master's sissy slave -chastity (Chinese and English subtitles)

1 year ago

xHamster

pantyhose, teen (18+), dildo, dirty talk, chinese, chastity
20:04

Shemale samurai challenges you to take her chastity

5 years ago

PornHub

toys, cosplay, chastity, solo
01:54 75%

Daddy made me a new milking toy on my chastity

2 years ago

xHamster

milk, 18, chastity
06:15

Bound blue Balls and Chastity forced to cum hands free.

1 year ago

xHamster

BDSM, swallow, chastity, hands free
11:10 71%

Sissy chastity (part 1)

2 years ago

PornHub

russian, cosplay, chastity
01:41 83%

Sissy in chastity fucked by different people

1 year ago

xHamster

sissy, chastity
10:20 61%

Sissy Boy Takes Huge Load In His Ass

1 year ago

PornHub

femdom, strapon, socks, pegging, sissy, chastity, cum in ass
09:57

Showering in steel chastity and latex

8 months ago

xHamster

homemade, bondage, shower, chastity
05:06

Sissy drinking cum

1 year ago

xHamster

chastity
05:07

Inverted Chastity Cages Make Me Feel So Slutty

10 months ago

xHamster

small cock, chastity, dildo
03:09

Sissy in Chastity

6 years ago

xHamster

lingerie, sissy, chastity
12:24

Slutty Trans Bunny Lilith Eclipse Fucks Herself With Carrots In Chastity Ass To Mouth

2 years ago

xHamster

fisting, cum in mouth, sissy, chastity
06:37

Sexy Blonde Femboy in Chastity - Bailey Wilde Photoshoot

4 months ago

xHamster

anal, chastity, amateur, femboy
11:11 58%

Rainbow Kitty Scarlet Sky Squirts Girl Cum!

1 year ago

PornHub

cute, squirt, orgasm, cumshot, masturbation, sissy, chastity
05:14

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

5 months ago

xHamster

huge dildo, chastity, sissy, big cock, small cock, cumshot
09:45

Sissy chastity day 2

2 months ago

xHamster

latina, sissy, shemale, chastity, dildo
07:16

Sissy fuck in chastity

1 year ago

xHamster

huge dildo, chastity
06:08

Sissy Francis Malice - Little Time for Fun Before Wife Comes Back Home

8 months ago

xHamster

german, wife, crossdresser, chastity
10:55

SissyCDMish - qos sissy camwhore with chastity cage, butt plug and dildo

7 months ago

xHamster

shemale, anal, dildo, crossdresser, sissy, chastity
03:15

Sissy Sherri fucked while tiny cock is caged in chastity

4 years ago

xHamster

chastity
06:14

Trans Woman in Chastity, Bondage and Leash Fucked POV

1 year ago

xHamster

bondage, bareback, chastity
10:13 75%

Chastised sissy Tgirl Lily Star Dribbles clitty nectar through her cage

1 year ago

PornHub

arab, fetish, bondage, dildo, BBC, hands free, chastity
08:06

Cute femboy in chastity ride my big cock

8 months ago

xHamster

cute, shemale, chastity, femboy
01:51 39%

Femboy Sissy in chastity cage and plugged playing outdoor

4 years ago

xHamster

public, prostate, teen anal (18+), outdoor, chastity
07:16

Chastity submited and fucked

7 years ago

xHamster

BDSM, chastity
05:16

How to wear a flat chastity cage

6 months ago

xHamster

italian, webcam, sissy, chastity
02:13

Trans witch summons something she doesn't mind riding

12 months ago

xHamster

sissy, chastity, FTM, dutch
01:54

Pissing nacked outdoor in my tiny chastity

1 year ago

xHamster

pissing, outdoor, bondage, chastity
03:03

MaureenNadh - (Day 1 Locked In Chastity) Anal Training Before School

1 year ago

xHamster

teen (18+), train, teen anal (18+), domination, chastity, solo
03:26

All sissy should be loked in chastity

5 years ago

xHamster

mature anal, ass, small tits, chastity
05:36 60%

Double Machine

2 years ago

xHamster

fetish, double anal, 18, machine, double penetration, chastity
05:47

Cutie Reina Hanno Swinging Nipple Suction and Rubbing Chastity Precum

11 months ago

xHamster

cute, small cock, nipples, chastity
10:00

CD chastity fuck

4 years ago

xHamster

homemade, mature anal, chastity
33:24 71%

Sissys Wooden Pony Ballet Boot Torment

1 year ago

xHamster

latex, fetish, bondage, boots, lingerie, BDSM, chastity
12:53

[SISSY] Libido processing failed. Did not ejaculate.

3 years ago

PornHub

asian, sissy, chastity, crossdresser
07:12

CUM IN CHASTITY WITH DILDO

4 years ago

xHamster

chastity
25:04

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

9 months ago

xHamster

bondage, BDSM, sissy, chastity
05:12

Sissy cum in inverted chastity cage after being denied for 60 days

1 year ago

xHamster

german, BBW, chastity
11:07

Ilandis in a chastity belt has fun with her anus, masturbates with an artificial penis

1 year ago

xHamster

beauty, russian, dildo, penis, asshole, chastity
01:19

Good Girls Wear Chastity Cages For Dates

1 year ago

xHamster

latex, heels, chastity
08:48

Hot sissy in tiny chastity cage masturbates with vibrator

1 year ago

xHamster

crossdresser, sissy, chastity
12:22

Sissy girl anal trainer with fuck machine bbc dildo

1 year ago

PornHub

chastity, femboy, BBC
10:48 79%

Jessica Bloom Multiple Caged Assgasms

3 years ago

PornHub

pissing, feet, dildo, british, heels, chastity
07:25

Sissy Maid Cums & Squirts Hard from Anal Fucking Machine in Chastity Cage - Jessica Bloom

3 months ago

xHamster

beauty, squirt, prostate, dildo, machine, sissy, chastity
04:26

Cute femboy in chastity cage masturbate with vibrator

2 years ago

xHamster

vibrator, chastity
05:34

Blonde big-titted slut fucking herself on bed 2023

1 year ago

xHamster

chastity
10:46 67%

Stefani boots anal in chastity ,swallow cum

5 years ago

xHamster

latex, creampie, anal, couple, boots, swallow, bareback
06:51

BBC Ken Fucks Me on My Back in Missionary with Verbal Dom Sissification - Candy Ass Sissy in Chastity Cage

12 months ago

xHamster

BBC, sissy, missionary, chastity
09:46

Real Trans Squirting from Anal - Erika Oak's Sissygasm

10 months ago

xHamster

squirt, swedish, hands free, chastity
10:33

Twink in dress, stockings and chastity play with his butt

6 months ago

PornHub

chastity, solo, stockings, amateur, dress
07:14

VERY HOT Blonde Crossdresser in Pink Chastity Fucked

8 months ago

xHamster

crossdresser, sissy, chastity
22:55 43%

Sissy Secretary in horny after work activities

1 year ago

xHamster

stockings, clit, secretary, nylon, sissy, chastity
08:17

SisK CD in purple EP3 her sissy clity is released from a super tiny chastity cage

2 years ago

xHamster

pantyhose, ladyboy, chastity
1:15:02

Pain and pleasure, chastity and lust, Part 2

3 years ago

xHamster

german, BDSM, JOI, chastity
09:38

Beautiful Sissy in chastity enjoys being fucked

5 years ago

xHamster

beauty, chastity, sissy
07:09

Sissy Leona Plays with Her Ass and Clitty

5 months ago

xHamster

beauty, chastity, sissy
07:34

Violet Chastity Chained to Fuck Machine

8 months ago

xHamster

homemade, bondage, cuckold, machine, gape, chastity
10:11

Sissy Chastity Sissygasm Drinking - Trans Cumslut Jessica Bloom

1 year ago

xHamster

orgasm, dildo, ladyboy, 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
14:50

Real sissy slut anal in chastity cage

10 years ago

xHamster

latex, slut, sissy, chastity
07:23

F Machine Alpha Fucks Sissy Asshole - Jessica Bloom Chastity Orgasm And Cum In Mouth

6 months ago

xHamster

feet, orgasm, cum in mouth, asshole, chastity
09:42

Maid in chastity does special service

5 years ago

xHamster

maid, small tits, chastity
02:10

Releasing my sissy clitty from inverter chastity cage

1 year ago

xHamster

clit, chastity
01:10

Masturbation in chastity belt

10 years ago

xHamster

chastity
11:31

Sissy in chastity gaping her asshole for your entertainment

8 months ago

PornHub

chastity
01:02

Instant Sissygasm Hands-free in Chastity

3 years ago

xHamster

mature anal, hands free, chastity
11:04

Multiple Prostate Orgasms in Chastity Jessica Bloom Sissy Milking

1 year ago

xHamster

prostate, orgasm, milk, british, chastity
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
10:19

My New Chastity Cage!

2 months ago

PornHub

chastity, solo, amateur
02:51

Mistress Cassidy Makes Crossdresser Wear Chastity

1 year ago

xHamster

femdom, chastity, femboy
01:38

Latex Kitty Gets Horny In The Chastity Cage

11 months ago

xHamster

latex, chastity

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