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Sissy Chastity

Sissy Chastity Milking
3:50
Sissy Chastity Milking
3 months ago
Gaping Sissygasms in Chastity and a Ruined Orgasm ending for this Eager Sissy Slut
5:45
Gaping Sissygasms in Chastity and a Ruined Orgasm ending for this Eager Sissy Slut
2 years ago
Cutie Trans Sissy in Chastity Scarlet Sky Collared and Leashed to Wall for Playtime!
6:12
Cutie Trans Sissy in Chastity Scarlet Sky Collared and Leashed to Wall for Playtime!
2 years ago
Sissy in Chastity gets fucked hard
17:27
Sissy in Chastity gets fucked hard
2 years ago
Sissy Candy in Black Lingerie and Chastity is Locked and Impaled on her Dildo Stand to try and Cum
9:37
Sissy Candy in Black Lingerie and Chastity is Locked and Impaled on her Dildo Stand to try and Cum
5 months ago
Sissy Haileydoll in Chastity Anal Training and Gapes
1:09
Sissy Haileydoll in Chastity Anal Training and Gapes
1 year ago
Chastity Sissy extremely embarrassing anal examination
1:43
Chastity Sissy extremely embarrassing anal examination
6 years ago
A GangBang for the Sissy Slut
1:56
A GangBang for the Sissy Slut
4 years ago
Sissy Crossdresser Struggles in Bondage and Chastity
1:37
Sissy Crossdresser Struggles in Bondage and Chastity
2 years ago
Sissy Scarlet Sky Cum Compilation!
3:20
Sissy Scarlet Sky Cum Compilation!
1 year ago
Latex Crossdresser Sissy Maid Struggles in Bondage
1:37
Latex Crossdresser Sissy Maid Struggles in Bondage
2 years ago
Trans Sissy Scarlet Sky Sissygasms all over herself in Chastity and Bondage!
18:10
Trans Sissy Scarlet Sky Sissygasms all over herself in Chastity and Bondage!
2 years ago
Sissy would not swallow
1:57
Sissy would not swallow
4 years ago
Sissy Dripping while Riding Dildo
2:04
Sissy Dripping while Riding Dildo
3 years ago
Sissy Juliette Gets Machine Fucked to Orgasm
1:22
Sissy Juliette Gets Machine Fucked to Orgasm
1 year ago
Sissy Crossdresser Plugged in Chastity Restrained and Gagged
5:59
Sissy Crossdresser Plugged in Chastity Restrained and Gagged
3 years ago
Muzzle Gagged Sissy Struggles in Bondage
1:33
Muzzle Gagged Sissy Struggles in Bondage
2 years ago
Sissy Stretching her Ass for you with Eye Contact
11:54
Sissy Stretching her Ass for you with Eye Contact
3 years ago
Chastity April - I made my Chastity Slave a new 'dick' so we can Break his Mind!
1:21
Chastity April - I made my Chastity Slave a new 'dick' so we can Break his Mind!
1 year ago
Sissy Candy Locked onto her Dildo Stand, Impaled on Huge Dildos Compilation
9:35
Sissy Candy Locked onto her Dildo Stand, Impaled on Huge Dildos Compilation
3 months ago
Femboy Sissy Fucks Dildo Cums and Eats it
13:42
Femboy Sissy Fucks Dildo Cums and Eats it
3 years ago
Sissy Slut Takes 12 Inch Horse Cock
2:34
Sissy Slut Takes 12 Inch Horse Cock
3 years ago
Sissy Slut Fucked Hard my Machine
4:52
Sissy Slut Fucked Hard my Machine
3 years ago
Sissy Slut Haileydoll BBC Dildo Riding in Chastity - Anal Training
1:19
Sissy Slut Haileydoll BBC Dildo Riding in Chastity - Anal Training
1 year ago
CUMpilation: Chastity Sissygasms, Ruined Orgasms, & Crossdressing Cumshots of a Desperate Sissy
10:18
CUMpilation: Chastity Sissygasms, Ruined Orgasms, & Crossdressing Cumshots of a Desperate Sissy
2 years ago
Average Day in the Life of a Sissy Butt Slut
6:22
Average Day in the Life of a Sissy Butt Slut
2 years ago
Extreme Humiliation!! Sissy Slut Lee Begs to be your Cumslut!
2:39
Extreme Humiliation!! Sissy Slut Lee Begs to be your Cumslut!
3 years ago
The best Chastity Compilation you'll ever See!
7:05
The best Chastity Compilation you'll ever See!
2 months ago
Downsizing my Boyfriend's Chastity Cage!
1:02
Downsizing my Boyfriend's Chastity Cage!
9 months ago
Converting cucks into BBC Sissies - Hour long version
62:04
Converting cucks into BBC Sissies - Hour long version
4 years ago
Femboy Sissy Gaping Ass and Riding Fuck Machine Hard - Sissy Jazzie
13:04
Femboy Sissy Gaping Ass and Riding Fuck Machine Hard - Sissy Jazzie
3 years ago
Sissy Musings 2021
5:26
Sissy Musings 2021
3 years ago
Cute Sissy in Pink Playing with her Ass and Riding a Thick Dildo
17:27
Cute Sissy in Pink Playing with her Ass and Riding a Thick Dildo
3 years ago
Sissy Shoots her Big Load of White Cum on her Dark Skirt after 1 Week of Chastity
2:34
Sissy Shoots her Big Load of White Cum on her Dark Skirt after 1 Week of Chastity
3 years ago
Sissy Jazzie has her first Sissygasm , Plays with Lollipops in her Ass, Anal Gapes
11:26
Sissy Jazzie has her first Sissygasm , Plays with Lollipops in her Ass, Anal Gapes
3 years ago
Shemale Trap Sissy Femboy Crossdresser Strip Masturbate Handjob Cum in Black Dress Stockings Heels
20:51
Shemale Trap Sissy Femboy Crossdresser Strip Masturbate Handjob Cum in Black Dress Stockings Heels
2 years ago
Sissy Wakes up Gagged & Restrained in Chair
1:20
Sissy Wakes up Gagged & Restrained in Chair
3 years ago
Sissy Slut Gapes Ass with Thick Dildo and Fuck Machine
12:23
Sissy Slut Gapes Ass with Thick Dildo and Fuck Machine
3 years ago
Pinku no Teisō Kōmon no Gyappu De Kawaī Yowamushi
7:29
Pinku no Teisō Kōmon no Gyappu De Kawaī Yowamushi
2 years ago
Amelia's first Sissygasm!
1:28
Amelia's first Sissygasm!
3 years ago
Totally Ruining my Feminized Cuckold's Orgasm is so much Fun
1:13
Totally Ruining my Feminized Cuckold's Orgasm is so much Fun
2 years ago
Scarlet Sky's Moaning and Orgasm Compilation!
2:07
Scarlet Sky's Moaning and Orgasm Compilation!
2 years ago
Remembering #LOCKTOBER ❤️ Lyric SISSY CHASTITY CUM ❤️ SHEMALE VERONICA TABOO with LOVE for all CAGED
4:30
Remembering #LOCKTOBER ❤️ Lyric SISSY CHASTITY CUM ❤️ SHEMALE VERONICA TABOO with LOVE for all CAGED
4 years ago
Sissy Chastity Training POV
1:17
Sissy Chastity Training POV
1 year ago
Sissification Lecture
16:47
Sissification Lecture "caged Sissy" Chastity Belts, Jerk, Sissygasm by Mistress Veronica Taboo
3 years ago
Sissy Chastity Training by DominaFire
1:15
Sissy Chastity Training by DominaFire
1 year ago
Piss compilation - sissy, chastity belt, locked, crossdresser, public, in front of girl, cock cage
10:22
Piss compilation - sissy, chastity belt, locked, crossdresser, public, in front of girl, cock cage
1 year ago
Femdom new Years Resolutions for Sissies & Chastity Cage Unboxing
13:57
Femdom new Years Resolutions for Sissies & Chastity Cage Unboxing
4 years ago
Femdom POV Sissy Chastity Training
5:22
Femdom POV Sissy Chastity Training
1 year ago
Femdom sissy chastity – English captions vol 3
2:28
Femdom sissy chastity – English captions vol 3
3 years ago
Cute Sissy Chastity Cage try on - 6 different Cages for you FULL VID on LayneLovee Manyvids
1:37
Cute Sissy Chastity Cage try on - 6 different Cages for you FULL VID on LayneLovee Manyvids
5 months ago
Mistress Mercer Sissy Chastity Slave Teased and Humiliated, Denied and Locked in the Vice
12:29
Mistress Mercer Sissy Chastity Slave Teased and Humiliated, Denied and Locked in the Vice
4 years ago
femdom sissy chastity 3050-3150
8:41
femdom sissy chastity 3050-3150
1 year ago
BDSM, Sissy Chastity
18:05
BDSM, Sissy Chastity
3 years ago
Sissy Chastity Maid Training
1:16
Sissy Chastity Maid Training
3 years ago
Trans Girl Humping Soft Fuzzy Blanket Plugged in Sissy Chastity
1:26
Trans Girl Humping Soft Fuzzy Blanket Plugged in Sissy Chastity
4 years ago
Training Zero Femdom Public Humiliation! Sissy Chastity Cage Flashing Piss Stinging Nettle Discipline Ballbusting CBT Real
1:13
Training Zero Femdom Public Humiliation! Sissy Chastity Cage Flashing Piss Stinging Nettle Discipline Ballbusting CBT Real
8 months ago
Sissy Chastity (part 1)
11:10
Sissy Chastity (part 1)
3 years ago
Sissy Chastity Machine Fuck
1:28
Sissy Chastity Machine Fuck
3 years ago
Mistress Mercer Cumming on FuckMachine Latex Sissy Chastity Release
1:06
Mistress Mercer Cumming on FuckMachine Latex Sissy Chastity Release
4 years ago
Training zero Public Humiliation! Sissy Chastity Cage Flashing Piss Stinging Nettle Discipline Ballb
1:10
Training zero Public Humiliation! Sissy Chastity Cage Flashing Piss Stinging Nettle Discipline Ballb
8 months ago
Interracial Cuckold Creampie Eating BBC Sissy Chastity Watches Hot Wife Fuck and Suck Big Black Cock
2:43
Interracial Cuckold Creampie Eating BBC Sissy Chastity Watches Hot Wife Fuck and Suck Big Black Cock
3 years ago
Best of Harmony Rose Vol 2 in Femdom Cuckold Creampie Eating SPH Sissy Chastity Face Sitting Hot Sex
1:58
Best of Harmony Rose Vol 2 in Femdom Cuckold Creampie Eating SPH Sissy Chastity Face Sitting Hot Sex
3 years ago
Pussy for my Slave
7:10
Pussy for my Slave
2 years ago
Cuckold Creampie Eating Sissy Chastity Hot Wife Fucking BBC Strapon Femdom and Hardcore Sex
2:02
Cuckold Creampie Eating Sissy Chastity Hot Wife Fucking BBC Strapon Femdom and Hardcore Sex
2 years ago
NSFW Transdick Transslut Ladyboy Femboy Trap Sissy Chastity Belt dare Shaved Short Phimosis Miserab
11:05
NSFW Transdick Transslut Ladyboy Femboy Trap Sissy Chastity Belt dare Shaved Short Phimosis Miserab
1 year ago
Crossdresser Ladyboy Femboy Trap Sissy Chastity Belt dare Shaved Short Phimosis Miserable Japanese
9:46
Crossdresser Ladyboy Femboy Trap Sissy Chastity Belt dare Shaved Short Phimosis Miserable Japanese
1 year ago
FROM PENIS TO BETTY CLITTY
4:51
FROM PENIS TO BETTY CLITTY
2 years ago
Pussy-Panties to have a Female Orgasm Teaching my Cuckold
3:26
Pussy-Panties to have a Female Orgasm Teaching my Cuckold
2 years ago
Hailey Doll Gets both her Holes Ruined by BBC😈💦
2:03
Hailey Doll Gets both her Holes Ruined by BBC😈💦
1 year ago
Rainbow Kitty Scarlet Sky Squirts Girl Cum!
11:11
Rainbow Kitty Scarlet Sky Squirts Girl Cum!
2 years ago
Scarlet Sky Sucks Mal's Big Cock!
7:21
Scarlet Sky Sucks Mal's Big Cock!
2 years ago
Full Body Latex Catsuit
1:14
Full Body Latex Catsuit
2 years ago
Hungry (Compilation of cumshots PMV)
12:23
Hungry (Compilation of cumshots PMV)
3 years ago
Orgasm with Artificial Pussy for Crossdresser
5:01
Orgasm with Artificial Pussy for Crossdresser
2 years ago
Anal Plug Carabiner for the KEYS OF THE MISTRESS
4:31
Anal Plug Carabiner for the KEYS OF THE MISTRESS
2 years ago
OUT ON THE STREET take my Cuckold Dressed as a Whore in Heels
2:23
OUT ON THE STREET take my Cuckold Dressed as a Whore in Heels
2 years ago
Locktober Sissy Chastity Training!
6:22
Locktober Sissy Chastity Training!
3 months ago
Anal Fisting Sissy Chastity Slut Deep by Hardcore FemDom Mistress Mercer
3:14
Anal Fisting Sissy Chastity Slut Deep by Hardcore FemDom Mistress Mercer
3 years ago
Skyler Storm Anal Masturbation in Sissy Chastity
35:21
Skyler Storm Anal Masturbation in Sissy Chastity
1 year ago
Sissy Chastity Cuckold Rides Latex Hotwife Dominatrix & Big Black Strappon Cock Reverse Cowgirl!
1:42
Sissy Chastity Cuckold Rides Latex Hotwife Dominatrix & Big Black Strappon Cock Reverse Cowgirl!
1 year ago
Sissy Chastity Vibrator Cum Challenge
9:49
Sissy Chastity Vibrator Cum Challenge
4 years ago
Sissy Chastity Training - Stretching my Fuckhole makes my Clitty Squirt Cum
6:30
Sissy Chastity Training - Stretching my Fuckhole makes my Clitty Squirt Cum
2 years ago
futa nurse pegging part 3: latex catsuit, sissy chastity, fisting - full video on Veggiebabyy Manyvids
1:51
futa nurse pegging part 3: latex catsuit, sissy chastity, fisting - full video on Veggiebabyy Manyvids
4 months ago
How Devilish Becky Turned you into her Sissy Chastity
8:35
How Devilish Becky Turned you into her Sissy Chastity
6 years ago
Maid Sissy & Chastity Femboy Hardcore Anal (feat. Evelyn Tumbles)
2:12
Maid Sissy & Chastity Femboy Hardcore Anal (feat. Evelyn Tumbles)
2 years ago
Nicole Aniston Cuckold POV 21 Creampie Eating Sissy Chastity Husband Sex
1:31
Nicole Aniston Cuckold POV 21 Creampie Eating Sissy Chastity Husband Sex
5 years ago
Sissy Chastity Sissygasm Drinking - Trans Cumslut Jessica Bloom
10:09
Sissy Chastity Sissygasm Drinking - Trans Cumslut Jessica Bloom
1 year ago
Hot Wife Cuckold Creampie Eating Sissy Chastity Strap on Pegging Femdom Swingers BBC Interracial Sex
1:16
Hot Wife Cuckold Creampie Eating Sissy Chastity Strap on Pegging Femdom Swingers BBC Interracial Sex
3 months ago
Carolyn Reese in Hot Wife Cuckold Creampie Eating Sissy Chastity and Fucking while Cuck Watches her
1:28
Carolyn Reese in Hot Wife Cuckold Creampie Eating Sissy Chastity and Fucking while Cuck Watches her
3 years ago
Podcast Ep13: Sissy, Chastity and Lust
49:07
Podcast Ep13: Sissy, Chastity and Lust
4 years ago
Hotwife Fucks BBC with Open Windows,sissy Chastity Husband Licks Clit with Good View, Sloppy Seconds
2:46
Hotwife Fucks BBC with Open Windows,sissy Chastity Husband Licks Clit with Good View, Sloppy Seconds
5 months ago
Hot Wife Cuckolds her Step Dad Creampie Eating POV Sissy Chastity
1:29
Hot Wife Cuckolds her Step Dad Creampie Eating POV Sissy Chastity
5 years ago
Amateur Balls Kicking and Trampling Sissy Chastity Cock Cage Slave Bound and Humiliated
5:58
Amateur Balls Kicking and Trampling Sissy Chastity Cock Cage Slave Bound and Humiliated
4 years ago
Sissy Chastity Trainer Spiral Anal Balls Feminization
24:44
Sissy Chastity Trainer Spiral Anal Balls Feminization
3 years ago
Femdom Session for Sissy. Chastity, Feminization, Teasing, Pegging, Ruined Orgasm and Cum Feeding
15:10
Femdom Session for Sissy. Chastity, Feminization, Teasing, Pegging, Ruined Orgasm and Cum Feeding
1 month ago
Mistress Mercer Extreme Deepthroat Strap-on Oral Cock Training for Sissy Chastity Slut
2:03
Mistress Mercer Extreme Deepthroat Strap-on Oral Cock Training for Sissy Chastity Slut
3 years ago
Cougar's Sissy Chastity Training #BratPerversions
4:36
Cougar's Sissy Chastity Training #BratPerversions
1 year ago
Hot Wife Cuckold Creampie Eating Sissy Chastity Strap on Pegging Femdom Swingers BBC Interracial Sex
2:24
Hot Wife Cuckold Creampie Eating Sissy Chastity Strap on Pegging Femdom Swingers BBC Interracial Sex
4 months ago
Get over here and Clean my Cum Filled Pussy and Ass
2:14
Get over here and Clean my Cum Filled Pussy and Ass
1 year ago
Double Domme Interrogation of a Sissy Chastity Male Slave
36:58
Double Domme Interrogation of a Sissy Chastity Male Slave
1 year ago
Flower Tucci Cuckold Hot Wife Creampie Eating Sissy Chastity Femdom Sex
1:14
Flower Tucci Cuckold Hot Wife Creampie Eating Sissy Chastity Femdom Sex
5 years ago
Cuckold Creampie Eating Hot Wife Sex and BBC Sissy Chastity Pussy Worship Femdom Sex and Bodybuilder
3:10
Cuckold Creampie Eating Hot Wife Sex and BBC Sissy Chastity Pussy Worship Femdom Sex and Bodybuilder
2 years ago
Locktober's Top 10 Chastity Ideas Vol.1
7:02
Locktober's Top 10 Chastity Ideas Vol.1
2 months ago
Locktober's Top 10 Chastity Ideas Vol.1
13:40
Locktober's Top 10 Chastity Ideas Vol.1
2 months ago
Proper Sissy Orgasm in Chastity, Vibrator on Clity, Fucking Machine in Ass
2:06
Proper Sissy Orgasm in Chastity, Vibrator on Clity, Fucking Machine in Ass
5 years ago
Female DOMINATION in DIAPERS and CHASTITY with a big ANAL plug and PISS
13:02
Female DOMINATION in DIAPERS and CHASTITY with a big ANAL plug and PISS
1 year ago
Reaching Sissygasm by Hitting my Clitty in Chastity with Big Headed Dildo (after Anal Play)
4:20
Reaching Sissygasm by Hitting my Clitty in Chastity with Big Headed Dildo (after Anal Play)
1 year ago
Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)
8:12
Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)
1 month ago
Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)
23:35
Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)
2 weeks ago
Chastity Sissy Agrees to Be Cuck to Get Unlocked. Then Wife Pegs Ass
10:55
Chastity Sissy Agrees to Be Cuck to Get Unlocked. Then Wife Pegs Ass
6 months ago
Sissygasm in Flat Chastity Cage
4:04
Sissygasm in Flat Chastity Cage
1 year ago
Alpha Male Fucking Sissy Bareback, Cums inside and she Starts Masturbating like a Girl in Chastity
14:40
Alpha Male Fucking Sissy Bareback, Cums inside and she Starts Masturbating like a Girl in Chastity
2 years ago
Erika Sissy in Chastity Sucking and Riding Cock. (My Sissy Ass Gets Fucked)
5:57
Erika Sissy in Chastity Sucking and Riding Cock. (My Sissy Ass Gets Fucked)
5 years ago
THE ULTIMATE CHASTITY CAGE REVIEW AND GUIDE VIDEO
37:26
THE ULTIMATE CHASTITY CAGE REVIEW AND GUIDE VIDEO
4 years ago
Milking the first drops from my SISSY's PROSTATE
11:53
Milking the first drops from my SISSY's PROSTATE
1 month ago
CHASTITY WILL MAKE YOUR MUSCLES GROW
1:07
CHASTITY WILL MAKE YOUR MUSCLES GROW
3 years ago
Chastity PEE and FISTING for SISSY slave
10:36
Chastity PEE and FISTING for SISSY slave
1 year ago
Sissy in Chastity is Allowed to have a Sissygasm with a Vibrator on her Clitty after Male Breeding
2:42
Sissy in Chastity is Allowed to have a Sissygasm with a Vibrator on her Clitty after Male Breeding
4 years ago
Sissygasm in Chastity after Duct Taping in a Vibrating Dildo inside my Ass
9:18
Sissygasm in Chastity after Duct Taping in a Vibrating Dildo inside my Ass
5 years ago
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