Bdsm Chastity Videos (33,297)

First-ever Time Handballing Vid with Cagedjock Part two Conversation and Handballing, Nip Have fun Booty Speculum, Rubdown Machine and Pegging

First-ever Time Handballing Vid with Cagedjock Part two Conversation and Handballing, Nip Have fun Booty Speculum, Rubdown Machine and Pegging

4Gay 5 days ago

Chastity with ball bondage and extreme nipple clamps

62% HD 0:39 / 9:36

Chastity with ball bondage and extreme nipple clamps

FapHouse 8 months ago

Femdom owns Sissies

Femdom owns Sissies

Eporner 11 months ago

Fucking with Hammer Drill Machine

53% HD 0:39 / 8:06

Fucking with Hammer Drill Machine

FapHouse 1 month ago

Erotic Electroshock Torment Spider Gag & Convulsing Chair

68% HD 1:01 / 12:26

Erotic Electroshock Torment Spider Gag & Convulsing Chair

FapHouse 3 months ago

hands free cum in cage with new toy

hands free cum in cage with new toy

xHamster 1 week ago

Sissy Cuckold Fed Creampie And Cum Foot Worship - Jessica Bloom ft Polieana

Sissy Cuckold Fed Creampie And Cum Foot Worship - Jessica Bloom ft Polieana

xHamster 1 year ago

First Time Fisting Video with Cagedjock Part 2 Interview and Fisting, Nipple Play Butt Plug, Massage Machine and Pegging

57% HD 0:39 / 39:28

First Time Fisting Video with Cagedjock Part 2 Interview and Fisting, Nipple Play Butt Plug, Massage Machine and Pegging

FapHouse 5 months ago

ride dildo

54% HD 2:00 / 6:53

Flirt4Free 4 years ago

bang my pluged butt ans cock in chastity

bang my pluged butt ans cock in chastity

xHamster 3 years ago

Sophia Loreen Private Show

HD 2:00 / 15:51

Sophia Loreen Private Show

Camster 1 week ago

Close up flat chastity cage with urethral plug play

Close up flat chastity cage with urethral plug play

xHamster 2 years ago

Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore

Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore

xHamster 8 months ago

Caged Sissy Maid Slave - Cleaning the Bathroom for Mistress and Her Boyfriend

Caged Sissy Maid Slave - Cleaning the Bathroom for Mistress and Her Boyfriend

xHamster 10 months ago

Maya Spring Private Show

Maya Spring Private Show

Camster 2 weeks ago

Trans Bitch in latex fists her ass and kneels for doggy pose fuck with sex machine

Trans Bitch in latex fists her ass and kneels for doggy pose fuck with sex machine

XGroovy 4 years ago

Whipping Punishment for the Sissy Slut - Part 1

Whipping Punishment for the Sissy Slut - Part 1

FapHouse 2 years ago

Sissy Joyce’s Very First Training Session with Her Two Mistress

58% 0:39 / 10:07

Sissy Joyce’s Very First Training Session with Her Two Mistress

FapHouse 2 months ago

Chastity Teen Fucked By Her Daddy

Chastity Teen Fucked By Her Daddy

Tranny.one 4 years ago

submissive rubber slave warms up it's ass and mouth before it's Master comes over

submissive rubber slave warms up it's ass and mouth before it's Master comes over

xHamster 2 weeks ago

Jhordy & Maxx Private Show

46% HD 2:00 / 1:47:48

Jhordy & Maxx Private Show

Flirt4Free 10 months ago

extreme Nipple Play

extreme Nipple Play

xHamster 4 years ago

Transformed husband into a slut and four more cocks and two dominatrixes

Transformed husband into a slut and four more cocks and two dominatrixes

xHamster 2 years ago

Sophia Loreen Private Show

HD 2:00 / 18:12

Sophia Loreen Private Show

Flirt4Free 2 weeks ago

Sophia Loreen Party on Apr 18, 2026 - Part 3

53% HD 2:00 / 33:08

Sophia Loreen Party on Apr 18, 2026 - Part 3

Flirt4Free 2 months ago

Femboy chained in chastity cage shows off and plays with her dildo.

Femboy chained in chastity cage shows off and plays with her dildo.

xHamster 2 years ago

Tommy & Master Private Show

Tommy & Master Private Show

Flirt4Free 4 months ago

Sophia Loreen Private Show

HD 2:00 / 22:54

Sophia Loreen Private Show

Camster 1 week ago

Submissive Artemis Faux whipped by trans Jessy Dubais massive cock

Submissive Artemis Faux whipped by trans Jessy Dubais massive cock

UrGayPorn 1 year ago

First Time Fisting Video with Cagedjock Part 2 Interview and Fisting, Nipple Play Butt Plug, Massage Machine and Pegging

First Time Fisting Video with Cagedjock Part 2 Interview and Fisting, Nipple Play Butt Plug, Massage Machine and Pegging

xHamster 3 weeks ago

Father bonks Natasha Magenta

Father bonks Natasha Magenta

Transvids.tv 9 months ago

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

xHamster 2 months ago

Fucking with Hammer Drill Machine

60% HD 1:01 / 8:06

Fucking with Hammer Drill Machine

FapHouse 1 month ago

Jessica Doll's Weekly Fuckmachine Therepy 2

Jessica Doll's Weekly Fuckmachine Therepy 2

xHamster 2 weeks ago

Shemale Submission Lesson

Shemale Submission Lesson

BigTitsLust 5 months ago

Patric & Simon & Frederick Private Show

55% HD 2:00 / 11:22

Patric & Simon & Frederick Private Show

Flirt4Free 2 years ago

The Vice Mach 2 chastity cage (prototype) product review!!

The Vice Mach 2 chastity cage (prototype) product review!!

xHamster 8 months ago

Lanna & Nefertiti Private Show

64% HD 2:00 / 5:57

Lanna & Nefertiti Private Show

Flirt4Free 3 years ago

Jacob Malik Private Show

62% HD 2:00 / 4:28

Jacob Malik Private Show

Flirt4Free 4 months ago

Colombian Boys Private Show

HD 2:00 / 23:35

Colombian Boys Private Show

Flirt4Free 2 years ago

Sophia Loreen Party on Jun 23, 2026 - Part 4

64% HD 2:00 / 35:23

Sophia Loreen Party on Jun 23, 2026 - Part 4

Camster 1 week ago

having a fantastic sissy time

having a fantastic sissy time

TrannyGem 1 year ago

Stiletto Sissy Slaves First Anal Stretching With Electrics And Chastity By Mistress Mercer

Stiletto Sissy Slaves First Anal Stretching With Electrics And Chastity By Mistress Mercer

getTranny 3 weeks ago

First Time Fisting Video with Cagedjock Part 2 Interview and Fisting, Nipple Play Butt Plug, Massage Machine and Pegging

First Time Fisting Video with Cagedjock Part 2 Interview and Fisting, Nipple Play Butt Plug, Massage Machine and Pegging

xHamster 5 months ago

Paulo & Jose & Sander Private Show

64% HD 2:00 / 11:56

Paulo & Jose & Sander Private Show

Flirt4Free 3 weeks ago

Patric & Alexander & Lian Private Show

48% HD 2:00 / 38:16

Patric & Alexander & Lian Private Show

Flirt4Free 3 years ago

TINY Girl, BIG Strapon - Crossdresser (SubPOV)

VR 1:30 / 21:36

TINY Girl, BIG Strapon - Crossdresser (SubPOV)

VRPorn 2 years ago

Jose & Richard Private Show

58% HD 2:00 / 21:33

Jose & Richard Private Show

Flirt4Free 1 month ago

Review: Chastity Cages for Sissies

Review: Chastity Cages for Sissies

xHamster 8 months ago

Chastity Compilation Trans and Sissy Girls Locked and Fucked

Chastity Compilation Trans and Sissy Girls Locked and Fucked

TrannyGem 4 years ago

Sophia Loreen Private Show

63% HD 2:00 / 18:12

Sophia Loreen Private Show

Camster 2 weeks ago

Paulo & Jose & Sander Private Show

59% HD 2:00 / 10:44

Paulo & Jose & Sander Private Show

Flirt4Free 1 month ago

Sissy selfbondage tied in abandoned attic

Sissy selfbondage tied in abandoned attic

xHamster 11 months ago

Paulo & Jose & Sander Private Show

60% HD 2:00 / 6:07

Paulo & Jose & Sander Private Show

Flirt4Free 3 weeks ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 3 weeks ago

Nicco & Patric & Santiago Private Show

44% HD 2:00 / 13:21

Nicco & Patric & Santiago Private Show

Flirt4Free 2 years ago

Jhordy & Maxx Private Show

58% HD 2:00 / 7:55

Jhordy & Maxx Private Show

Flirt4Free 10 months ago

Elegant Beauty in White Dress and Nude Nylon Got Tied up, Lost Control and Orgasm by Anal Hook and Vibrators.

50% HD 0:39 / 9:20

Elegant Beauty in White Dress and Nude Nylon Got Tied up, Lost Control and Orgasm by Anal Hook and Vibrators.

FapHouse 4 months ago

Hi I'm Linzy19

xHamster 3 years ago

good Sissy In Virginity Likes Being pulverized

good Sissy In Virginity Likes Being pulverized

Transvids.tv 9 months ago

Sophia Loreen Party on Apr 25, 2026 - Part 3

57% HD 2:00 / 1:59:26

Sophia Loreen Party on Apr 25, 2026 - Part 3

Flirt4Free 2 months ago

Sandy Nell Private Show

67% HD 2:00 / 4:19

Sandy Nell Private Show

Flirt4Free 5 years ago

Fucking Petite Trans - Compilation 3

HD 0:10 / 20:05

Fucking Petite Trans - Compilation 3

LoyalFans 4 days ago

Sissy cockslut Is What you Will Always Be

Sissy cockslut Is What you Will Always Be

Transvids.tv 9 months ago

Sissy Cathy poses outdoors in school uniform with chastity cage exposed

Sissy Cathy poses outdoors in school uniform with chastity cage exposed

Gay3X 4 years ago

Nicco & Patric & Santiago Have Amazing Threesome

59% HD 2:00 / 1:04:58

Nicco & Patric & Santiago Have Amazing Threesome

Flirt4Free 2 years ago

You're a pathetic sissy bitch with a tiny penis!!!

You're a pathetic sissy bitch with a tiny penis!!!

Pornzona 6 days ago

Aiden Ward Fist Jona Ortiz

63% 0:39 / 21:27

Aiden Ward Fist Jona Ortiz

FapHouse 2 months ago

Bbc Vs Sissy In Chastity 2

Bbc Vs Sissy In Chastity 2

getTranny 8 months ago

Lianna Lawson - Ample Pink Cigar Juggling

Lianna Lawson - Ample Pink Cigar Juggling

TrannyGem 3 years ago

Aleex & Paulo Private Show

52% HD 2:00 / 9:50

Aleex & Paulo Private Show

Flirt4Free 1 year ago

Niki Stuck Tight! Pink Rope & Duct Tape Session

52% HD 1:01 / 25:13

Niki Stuck Tight! Pink Rope & Duct Tape Session

FapHouse 1 month ago

Sandy Nell Private Show

Sandy Nell Private Show

Flirt4Free 3 years ago

Sandy Nell Private Show

4K 2:00 / 16:10

Sandy Nell Private Show

Flirt4Free 6 months ago

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

xHamster 3 months ago

Kira's Self-bondage Dream

HD 0:39 / 58:17

Kira's Self-bondage Dream

FapHouse 1 month ago

Jessica Doll's Every single week Fuckmachine Therepy two

Jessica Doll's Every single week Fuckmachine Therepy two

ShemaleSin 1 week ago

Aiden Ward Fist Jona Ortiz

71% 1:01 / 21:27

Aiden Ward Fist Jona Ortiz

FapHouse 2 months ago

Extreme spiked chastity

Extreme spiked chastity

xHamster 2 years ago

Disappointed Sissy Plugged and in Chastity

Disappointed Sissy Plugged and in Chastity

ShemaleSin 2 weeks ago

Sophia Loreen Party on Jun 9, 2026 - Part 3

HD 2:00 / 1:07:26

Sophia Loreen Party on Jun 9, 2026 - Part 3

Flirt4Free 3 weeks ago

Jhon & Derek & Chris Private Show

43% HD 2:00 / 32:48

Jhon & Derek & Chris Private Show

Flirt4Free 3 years ago

Humiliation of my small penis. Superglue tiny chastity. Permanent risk

Humiliation of my small penis. Superglue tiny chastity. Permanent risk

xHamster 2 years ago

Sissy White Boi and His Wife: Strippers for Large Ebony Dad - Queen of Spades - Chapter three: the Club (ai Animated)

Sissy White Boi and His Wife: Strippers for Large Ebony Dad - Queen of Spades - Chapter three: the Club (ai Animated)

ShemaleSin 3 days ago

Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot

63% HD 0:39 / 5:27

Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot

FapHouse 11 months ago

Niki Stuck Tight! Pink Rope & Duct Tape Session

49% HD 0:39 / 25:13

Niki Stuck Tight! Pink Rope & Duct Tape Session

FapHouse 1 month ago

Sophia Loreen Party on Feb 28, 2026 - Part 3

4K 2:00 / 2:01:04

Sophia Loreen Party on Feb 28, 2026 - Part 3

Flirt4Free 4 months ago

Sissys Dream 1

46% HD 0:39 / 13:14

FapHouse 1 year ago

Gasmask sissys anal takes big dildo

Gasmask sissys anal takes big dildo

Pornzona 4 days ago

Sophia Loreen Private Show

60% HD 2:00 / 4:42

Sophia Loreen Private Show

Flirt4Free 1 month ago

Encaged sissy caught in public

Encaged sissy caught in public

GayCK 3 years ago

Chastity-caged Sissy Gets Sideways Spoon-fucked Slow and Deep, Whispered Into Total Breeding Submission 1

63% HD 0:39 / 10:51

Chastity-caged Sissy Gets Sideways Spoon-fucked Slow and Deep, Whispered Into Total Breeding Submission 1

FapHouse 2 weeks ago

Nettles chastity torture

Nettles chastity torture

xHamster 3 years ago

Briann & Elvis & Patric Private Show

54% HD 2:00 / 7:04

Briann & Elvis & Patric Private Show

Flirt4Free 2 years ago

Chancing normal chastity to micro chastity cage with penis plug

Chancing normal chastity to micro chastity cage with penis plug

xHamster 2 years ago

BG pegging - fucking and breeding my locked CD sissy bf - full video on Veggiebabyy Manyvids

BG pegging - fucking and breeding my locked CD sissy bf - full video on Veggiebabyy Manyvids

xHamster 2 years ago

Flat chastity cage with penis plug Cumshot

Flat chastity cage with penis plug Cumshot

xHamster 2 years ago

Got a Fat Load Splattered on My Face by My Horny Boyfriend. First Time Taking a Huge Cumshot Like That

Got a Fat Load Splattered on My Face by My Horny Boyfriend. First Time Taking a Huge Cumshot Like That

Jizzberry 10 months ago

Trans Girl Rides Dildo in Chastity

Trans Girl Rides Dildo in Chastity

xHamster 4 months ago

Locktober - 28 October changing penis plug

Locktober - 28 October changing penis plug

xHamster 2 years ago

Jhordy & Maxx Private Show

69% HD 2:00 / 5:03

Jhordy & Maxx Private Show

Flirt4Free 10 months ago

Ideal Trans Sex Kitten Jade Stone Submits to Corporalist

Ideal Trans Sex Kitten Jade Stone Submits to Corporalist

FreePorn8 9 months ago

Cute Trans Gal Drilled Coarse by a Large Thick Rod

Cute Trans Gal Drilled Coarse by a Large Thick Rod

FreePorn8 1 week ago

Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm

Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm

xHamster 1 year ago

Part 1 My Husband Turned Into Latex Sissy Doll Good to Fuck - Mistress Julia

65% HD 1:01 / 12:50

Part 1 My Husband Turned Into Latex Sissy Doll Good to Fuck - Mistress Julia

FapHouse 9 months ago

Jhordy & Maxx Private Show

56% HD 2:00 / 24:38

Jhordy & Maxx Private Show

Flirt4Free 10 months ago

2 Sissies 1 Chastity Cage

2 Sissies 1 Chastity Cage

xHamster 1 year ago

Ladyboy teen with big boobs in bondage blowjob and anal fucking from behind

Ladyboy teen with big boobs in bondage blowjob and anal fucking from behind

Tranny.one 2 years ago

POV: Young Gothic Sissy Girl Comes Home And Takes Care Of Your Cock

POV: Young Gothic Sissy Girl Comes Home And Takes Care Of Your Cock

xHamster 10 months ago

Cock and ball bound extremely tight with pink rope until they turn dark purple and go numb and cold

Cock and ball bound extremely tight with pink rope until they turn dark purple and go numb and cold

xHamster 3 years ago

Sophia Loreen Private Show

HD 2:00 / 12:05

Sophia Loreen Private Show

Flirt4Free 1 month ago

Desire Sweet Private Show

Desire Sweet Private Show

Camster 9 months ago

Luna Florez Private Show

4K 2:00 / 18:06

Luna Florez Private Show

Camster 10 months ago

Erotic Electroshock Torment Spider Gag & Convulsing Chair

HD 0:39 / 12:26

Erotic Electroshock Torment Spider Gag & Convulsing Chair

FapHouse 3 months ago

Patric & Alexander & Lian Private Show

48% HD 2:00 / 1:09:57

Patric & Alexander & Lian Private Show

Flirt4Free 3 years ago

AB081 Sensitive Unstoppable squirting - Thick faux penis (Asian and English subtitles)

AB081 Sensitive Unstoppable squirting - Thick faux penis (Asian and English subtitles)

MyTransfix 1 month ago

Sophia Loreen Private Show

58% HD 2:00 / 31:53

Sophia Loreen Private Show

Flirt4Free 1 month ago

Master & Ithan Private Show

54% HD 2:00 / 9:40

Master & Ithan Private Show

Flirt4Free 1 year ago

Feminized - Stretching the Slut 1

Feminized - Stretching the Slut 1

TrannyGem 7 years ago

Julieta Shayk Private Show

65% HD 2:00 / 26:54

Julieta Shayk Private Show

Flirt4Free 6 months ago

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