TRANNY • CHASTITY 2,031 videos

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07:52

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

1 year ago

xHamster

mature, beauty, instruction, BDSM, ladyboy, sissy, chastity
06:27 69%

Chastity Sissy Raine Playing With Huge Dildo

1 year ago

Upornia

huge dildo, dildo, chastity
33:30

Chastity male vs shemale

9 years ago

TXXX

shemale and girl, vintage, chastity
11:10 63%

Real sissy in chastity outdoor

5 years ago

TXXX

outdoor, sissy, chastity, amateur
10:01

Very Hot Blonde Crossdresser In Chastity Fucked

1 year ago

ShemaleZ

crossdresser, amateur, stockings, chastity
01:42

Trans woman putting on a chastity device

2 years ago

xHamster

bondage, chastity
06:12 60%

Daddy fucks sissy in chastity

6 years ago

xHamster

mature, mature anal, chastity
07:59 50%

Transgirl In Chastity Gets Fucked By Crossdressing Sissy!

2 years ago

ShemaleZ

latex, crossdresser, chastity, sissy
11:26 43%

Sissy Trans Girl In Chastity Gets Fucked Hard In Multiple Positions

2 years ago

ShemaleZ

sissy, chastity
49:33

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

2 years ago

xHamster

french, chastity
03:36

Trans Woman Fucked Reverse Cowgirl In Chastity

2 years ago

ShemaleZ

chastity
06:16

Sissy In Plaid School Girl Miniskirt Gets Probed Deep By Hankeys Sigmaloid While In Pink Chastity

4 years ago

ShemaleZ

chastity, sissy
07:15 80%

Hot Blonde Sissy Bailey Wilde in Chastity Fucked Missionary

9 months ago

xHamster

BDSM, crossdresser, blonde, domination, sissy, missionary, chastity
05:48

Sexy sissy fisted while sliding a sounding rod deep in her chastity locked clit until squirting everywhere

10 months ago

xHamster

pissing, mature, squirt, fisting, sissy, chastity
01:45

Trans Beauty in Chastity Fucked

2 years ago

xHamster

chastity
15:32 81%

Russian Femboy Fucks With Mistress For The First Time With A Huge Strapon Tied With A Chastity

4 years ago

ShemaleZ

femdom, strapon, russian, fisting, BDSM, tied, first time
09:39

Day 12 Of 26 In Chastity And Denial. Vibrating My Cage And Plug For Teasing

2 years ago

HClips

stockings, latex, chastity, vibrator
15:29

Pee Tasting And Chastity Masturbation Of A Kinky Latexdoll

3 years ago

Upornia

pissing, chastity
14:07

Cute Trans Girl Spends Her First Time In Chastity Cage Riding Dragon Dick

3 years ago

ShemaleZ

first time, chastity
01:55 83%

Audrey Tgirl with huge sextoys and her chastity cage

2 years ago

xHamster

french, solo, crossdresser, small tits, chastity
33:23

One best anal creampie with chastity cum eating

7 years ago

ShemaleZ

latex, chastity, creampie
02:28

Tgirl in Chastity Fucked Doggystyle

2 years ago

xHamster

BDSM, dogging, chastity
06:32 53%

Fisting sissy in chastity cum hands free

6 years ago

ShemaleZ

train, fisting, lingerie, toys, hands free, chastity
09:22

Ilandis in a chastity belt and stockings has fun with his anus, fucks himself with an artificial dick

2 years ago

xHamster

feet, masturbation, chastity
04:11 67%

Dominatrix Makes Hot Blonde Sissy Wear Chastity And Get Fucked

2 years ago

ShemaleZ

mature, BDSM, sissy, chastity
10:03 67%

Sexy Blonde Crossdresser in Chastity Fucked

8 months ago

xHamster

BDSM, crossdresser, domination, sissy, chastity, femboy
10:47

Sissy Destroys Her Ass While Is Chastity

1 year ago

ShemaleZ

sissy, chastity
07:14

Sissy Marissa cheering for cock

1 year ago

xHamster

bondage, crossdresser, sissy, chastity, dildo
16:00 64%

Baby Doll - Sissy Chastity, Fills Hole And Is Humiliated

3 years ago

HClips

doll, sissy, chastity, solo
06:59

Red Angora Dress Chastity Tears and Cream

4 years ago

xHamster

mature anal, dress, chastity, mature
07:34

Sissy Juliette in chastity lockdown for 8h. kinky fun with toys all night at home

1 year ago

xHamster

swedish, sissy, chastity, latex, smoking, fetish
13:34 83%

Deep Throatfuck + Bareback Doggy Assfuck Cumshot Breeding By Shemale In Twink Ass (sub In Chastity)

4 years ago

TXXX

shemale, dogging, chastity, creampie compilation, creampie
27:10

Chastity fucked

8 years ago

ShemaleZ

chastity
21:45 60%

Flat Chastity Sissy

7 months ago

xHamster

squirt, dildo, sissy, chastity
08:29

EStim in Chastity 2 with Second Shocker

5 years ago

xHamster

chastity
08:24 92%

Goddess In Chastity Fists Her Perfect Ass To Orgasm

3 years ago

HClips

orgasm, fisting, chastity, solo, amateur, blonde
01:23

Puppy in chastity fucked

5 years ago

xHamster

mature anal, chastity
05:13

Cute & Sweet Girlfriend Turned Boyfriend Into Her Pegging Slut In Chastity. 5 Min

2 years ago

ShemaleZ

cute, BDSM, pegging, chastity
05:00

Ladyboy Yuta Test New Sex Chastity

2 years ago

ShemaleZ

18, chastity
05:14 75%

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

1 year ago

xHamster

small cock, huge dildo, british, cumshot, big cock, sissy, anal orgasm
09:44

Anal Pleasure

8 months ago

xHamster

sissy, crossdresser, chastity
08:00

Locktober Chastity Suck Slut for Dommes Bambi Bliss and Brittany Andrews

3 years ago

TXXX

chastity
11:53 75%

Bondage machine fuck with electro chastity

5 years ago

xHamster

latex, mature anal, bondage, electro, toys, machine, chastity
06:37

Sexy Blonde Femboy in Chastity - Bailey Wilde Photoshoot

1 year ago

xHamster

anal, chastity, amateur, femboy
11:08

Pink Goth Maid In Chastity Riding Dildos- Part 2 (sissygasm)

4 years ago

HClips

maid, riding, goth, chastity
10:23 50%

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4 years ago

xHamster

cuckold, chastity
06:42

Sissy In Chastity In Black Stockings And Boots Riding Large Green Dildo

2 years ago

Upornia

boots, dildo, sissy, chastity
25:04

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

1 year ago

xHamster

bondage, BDSM, sissy, chastity, dildo
32:07

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

2 years ago

xHamster

french, chastity
08:29

Waking up with Transgender girl stacie in chastity

6 years ago

ShemaleZ

BDSM, chastity
07:13

Sissygasms In Chastity

2 years ago

TXXX

chastity
09:50

Trans Anal Fisting And Prolapse In Chastity

2 years ago

ShemaleZ

fetish, fisting, BDSM, chastity
04:35

Foxyirene Shemale Chastity

3 years ago

ShemaleZ

chastity
01:38

Latex Kitty Gets Horny In The Chastity Cage

1 year ago

xHamster

latex, chastity
02:40

Cum in my Chastity

3 years ago

xHamster

german, chastity
09:39

Sissy Tammy Fucks Sex Machine While In Chastity

4 years ago

TXXX

machine, chastity
01:12

Sissy Haileydoll In Chastity Anal Training And Gapes

2 years ago

xHamster

dildo, chastity
08:33

Lilac Angora Tiny Chastity Huge BBC - Drip Milk Sissygasm

5 years ago

xHamster

huge dildo, milk, BBC, chastity
07:23

Chastity Gudrun And Angie

4 years ago

TXXX

chastity, amateur
03:53

Big Ass Trans Woman In Chastity Fucked Doggystyle

2 years ago

ShemaleZ

BDSM, dogging, chastity
06:28

Sexyslut driving in chastity device

9 years ago

xHamster

outdoor, chastity
05:04

Sissygasm In Chastity

4 years ago

xHamster

chastity
11:17

Kelsey Masters In Trans Woman In Bondage And Chastity Masturbating With Guy 12 Min

1 year ago

ShemaleZ

latex, shemale, bondage, BDSM, chastity
51:23 67%

Linzy19's Guide To Chastity

2 years ago

xHamster

prostate, fetish, BDSM, domination, JOI, chastity
42:07 50%

A cute trans girl gets wrapped in shrink wrap also cbt

5 years ago

ShemaleZ

cute, fetish, BDSM, chastity
28:47 59%

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

3 years ago

xHamster

bondage, chastity, post op, masturbation
08:41 63%

Crossdresser Compilation Beautiful Ladyboy Fucked Sissy Chastity Fucked Femdom

4 years ago

ShemaleZ

femdom, fisting, BDSM, crossdresser, chastity, compilation
07:22

Sissy schoolgirl Tina Noxx fucking her dildo in chastity!!

4 years ago

xHamster

chastity
06:14 75%

Trans Woman in Chastity, Bondage and Leash Fucked POV

2 years ago

xHamster

bondage, bareback, chastity
05:54

Multiorgasm sissy riding dildo

1 year ago

xHamster

chastity, sissy, crossdresser
07:32 60%

FULL TIME CHASTITY

8 years ago

xHamster

latex, full movie, chastity
01:55

Latex sissy nun fuck herself in chastity

5 years ago

xHamster

latex, nun, chastity
06:08

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

1 year ago

xHamster

german, wife, crossdresser, chastity
13:15

Sissy chastity

6 years ago

TXXX

chastity
07:18 64%

Cute Crossdresser Leopard Dress and Red Heels

1 year ago

xHamster

big ass, lingerie, crossdresser, heels, dress, chastity
14:38

Sissy In Chastity With Ripped Gym Pants And Getting Her Hole Destroyed

1 year ago

ShemaleZ

big ass, chastity, sissy, amateur
16:05

Mexican Sissy Maid un chastity Cage

2 years ago

xHamster

maid, mexican, chastity
02:31 80%

Mistress in chastity fuck sissy strapon cum and incontinence

5 years ago

xHamster

femdom, strapon, chastity
06:14 60%

Girl Licking Balls In Chastity Belt 6 Min

2 years ago

Upornia

shemale and girl, chastity
07:41

Be Our Gym Sissy Cuck In Chastity - Bella Blu And Lucy Hart

1 year ago

Upornia

stockings, shemale, sissy, chastity
32:11

Lizzy Yum In August 2022 #8 Sex Machines Erotic Electricity & Bsdm-chastity

3 years ago

ShemaleZ

erotic, machine, chastity, solo
07:14

VERY HOT Blonde Crossdresser in Pink Chastity Fucked

1 year ago

xHamster

crossdresser, sissy, chastity
03:33

Chastity caged at bedtime

8 years ago

ShemaleZ

chastity
02:55

Dominatrix Strapon Fucked Crossdresser in Chastity

2 years ago

xHamster

strapon, BDSM, chastity
02:39

Trap Locks Herself in Chastity

5 years ago

xHamster

chastity
03:20

Cristal Kinky In Latex Anal Training My Sissy Slut Fisting Big Anal Toys Big Strap On Preview

3 years ago

ShemaleZ

latex, strapon, train, fisting, slut, sissy, chastity
12:43 60%

Double anal in chastity

8 years ago

TXXX

double anal, double penetration, chastity
07:34

Violet Chastity Chained to Fuck Machine

1 year ago

xHamster

homemade, bondage, cuckold, machine, gape, chastity
13:33

Sissy in Chastity putting on a show

6 years ago

ShemaleZ

chastity
02:10

Releasing my sissy clitty from inverter chastity cage

2 years ago

xHamster

clit, chastity
03:39 60%

Latex rubber Doll Anal Training, in Chastity

6 years ago

TXXX

latex, rubber, doll, train, fetish, chastity
09:59 84%

Hot Blonde Bailey Wilde Removes Chastity Then Jerks Off

1 year ago

xHamster

handjob, amateur, BDSM, chastity, femboy, sissy
06:45 86%

Twinkerbell Pegging The Lost Femboi With Feminization And Chastity

1 year ago

HClips

chastity, shemale, amateur, pegging
05:22

Gorgeous Shemale Feminized in Chastity

3 years ago

xHamster

chastity
03:19

Tranny In Chastity Anal Challenge Dildo Ride

2 years ago

ShemaleZ

dildo, toys, chastity
25:44

Cute trap The Mortal Medusa in chastity

6 years ago

ShemaleZ

cute, chastity
04:42

Sissy Bitch Dagmar321 Chastity and Cum Pantihose

5 years ago

xHamster

chastity, mature
18:52

Latexa creature in chastity cage

8 years ago

TXXX

latex, chastity
06:00 40%

Femdom Double Anal Pegging for Chastity Sissy Lucy

3 years ago

xHamster

femdom, strapon, double anal, pegging, chastity
03:58

Hot Trans Woman In Chastity Fucked Doggystyle

2 years ago

Upornia

chastity
02:19

Chastity &Latex

11 years ago

xHamster

vintage, chastity
05:05

Full fashion stocking chastity lady

9 years ago

TXXX

stockings, chastity
06:06 83%

Fetish dresser babe gurl Andreina

2 years ago

xHamster

pantyhose, italian, solo, crossdresser, chastity
01:52

Crossdresser in Chastity Ready for Cock

3 years ago

xHamster

sissy, chastity, crossdresser
07:03

Cumming real hard in chastity with my wand

4 years ago

xHamster

JOI, chastity
09:39 59%

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

1 year ago

xHamster

black, fetish, bondage, dildo, lingerie, crossdresser, sissy
11:30

Trans Slut In Chastity Fucks Her Dildo To Orgasm

4 years ago

TXXX

orgasm, slut, chastity
05:29 79%

Machine Spit Roast Chastity Fuck In Bondage

4 years ago

ShemaleZ

latex, bondage, machine, domination, chastity, BDSM
12:48

Misr4 - chastity cage anal nipple sissygasms

2 years ago

xHamster

pissing, mature, dildo, nipples, hands free, chastity
07:29

Sis-k Pinky Chinese Dress Ep2: Anal Play

1 year ago

xHamster

mature anal, dildo, chinese, dress, chastity
01:02

Chastity Tales

4 years ago

xHamster

chastity
20:08

Sissy Maid Self Bondage in Spiked Chastity Cage

3 years ago

xHamster

latex, bondage, maid, chastity
17:28 80%

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

2 years ago

xHamster

cumshot, hands free, chastity, cum in ass, masturbation
21:39 60%

Chastity Sub Sprays Ruined Orgasm Everywhere

1 year ago

HClips

amateur, orgasm, shemale, chastity, fetish
08:31

Sissy in chastity cage cums hands free while riding big black dildo

7 years ago

ShemaleZ

dildo, sissy, hands free, chastity
04:01

Chastity sissy machine-fucked sucking Daddy

6 years ago

ShemaleZ

machine, chastity
05:01

Sissy In Chastity Fucks Herself Dumb

3 years ago

ShemaleZ

chastity
09:24

Transexual Stunner in Chastity

4 years ago

xHamster

chastity
08:46

Hubby cums from pegging alone. Real anal cum. Femdom. Chastity. Cum denial

6 years ago

ShemaleZ

femdom, couple, BDSM, pegging, chastity
06:05 40%

Cd Caged By Femdom Girlfriend Slave Cums In Chastity Ru

3 years ago

ShemaleZ

femdom, girlfriend, chastity

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