Cuckold Chastity Videos (28,323)

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 1 week ago

Tommy & Master Private Show

63% HD 2:00 / 11:13

Tommy & Master Private Show

Flirt4Free 7 months ago

Ride and squirt show!

Ride and squirt show!

Flirt4Free 5 years ago

Luna Florez Private Show

Luna Florez Private Show

Camster 1 week ago

Just Outta Curiosity

Just Outta Curiosity

Clips4sale 3 years ago

ten Rules for Milky Boi's

ten Rules for Milky Boi's

TrannyGem 6 years ago

Stupid Sissy in Halloween Costume and Chastity Cage Surrenders and Jerks Off to Big Black Cock

Stupid Sissy in Halloween Costume and Chastity Cage Surrenders and Jerks Off to Big Black Cock

XHamster 11 months ago

Sandy Swallows 12

55% HD 2:00 / 4:01

Sandy Swallows 12

Flirt4Free 9 years ago

Sharing a Massive Trans BBC with My Wife While She Watched Me Take a Huge Creampie in My Blonde Ass

HD 0:39 / 15:41

Sharing a Massive Trans BBC with My Wife While She Watched Me Take a Huge Creampie in My Blonde Ass

FapHouse 2 months ago

Sophia Loreen Private Show

HD 2:00 / 15:26

Sophia Loreen Private Show

Camster 5 years ago

Sabrina Smiith Private Show

HD 2:00 / 10:53

Sabrina Smiith Private Show

Flirt4Free 10 months ago

Sandy Lee Private Show

HD 2:00 / 23:21

Sandy Lee Private Show

Camster 10 years ago

Free day from the cage

Free day from the cage

XHamster 1 year ago

Sissy Pussy Orgasm

65% HD 1:01 / 9:53

Sissy Pussy Orgasm

FapHouse 2 months ago

Sensual Teasing and Pillow Riding

Sensual Teasing and Pillow Riding

Camster 2 years ago

Feminized slut strap-on fucked to MASSIVE sissygasm

Feminized slut strap-on fucked to MASSIVE sissygasm

Clips4sale 9 months ago

Soaking Wet Pussy

Soaking Wet Pussy

Flirt4Free 11 years ago

Master & Ithan Private Show

67% HD 2:00 / 28:44

Master & Ithan Private Show

Flirt4Free 1 year ago

My mate's bf had lovemaking with me while she was in the bathroom - Accomplish in Crimson - Arya Santana

My mate's bf had lovemaking with me while she was in the bathroom - Accomplish in Crimson - Arya Santana

TrannyGem 2 months ago

Lisan & Mine Private Show

4K 2:00 / 15:01

Lisan & Mine Private Show

Flirt4Free 3 weeks ago

Sandy Lee Private Show

Sandy Lee Private Show

Flirt4Free 11 years ago

Master & Ithan Private Show

62% HD 2:00 / 44:15

Master & Ithan Private Show

Flirt4Free 1 year ago

Kellystar518 in PRETTY SISSY gets LOCKED

Kellystar518 in PRETTY SISSY gets LOCKED

XHamster 1 year ago

Desire Sweet Private Show

HD 2:00 / 17:17

Desire Sweet Private Show

Flirt4Free 1 year ago

Sabrina Smiith Private Show

4K 2:00 / 54:09

Sabrina Smiith Private Show

Camster 9 months ago

Ambar & Lord Private Show

Ambar & Lord Private Show

Flirt4Free 3 weeks ago

Lyndon F Private Show

66% HD 2:00 / 23:35

Lyndon F Private Show

Flirt4Free 1 year ago

trans snowbunny gets filled up by BBC and cums in flat cage

70% 4K 0:13 / 9:01

trans snowbunny gets filled up by BBC and cums in flat cage

Clips4sale 1 year ago

My Sissy Transformation Experience (Trans Roleplay)

Premium HD 10:12

My Sissy Transformation Experience (Trans Roleplay)

Clips4sale 4 months ago

Sandy Lee Private Show

HD 2:00 / 28:01

Sandy Lee Private Show

Camster 10 years ago

Lisan & Mine Private Show

55% 4K 2:00 / 4:59

Lisan & Mine Private Show

Camster 2 weeks ago

Marian & Richard Private Show

60% HD 2:00 / 5:16

Marian & Richard Private Show

Camster 3 months ago

Sandy Pushes the Limits of Anal

HD 2:00 / 10:54

Sandy Pushes the Limits of Anal

Camster 9 years ago

Tatiana & Owen Private Show

61% HD 2:00 / 11:20

Tatiana & Owen Private Show

Camster 2 months ago

Hotwife BBC Creampie Cleanup – Beta Cuck Eats Every Drop

63% 0:33 / 20:34

Hotwife BBC Creampie Cleanup – Beta Cuck Eats Every Drop

Clips4sale 7 months ago

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

Premium HD 9:22

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

XVideosRed 1 year ago

The more I pump, the More I Grow, the More you Shrink

HD 0:30 / 11:32

The more I pump, the More I Grow, the More you Shrink

Clips4sale 1 year ago

Cuckold Chastity thrall screws femboy booty 4 Femdom-Goddess so many jocks, used like a admirable sissy wench 4/5

Cuckold Chastity thrall screws femboy booty 4 Femdom-Goddess so many jocks, used like a admirable sissy wench 4/5

ShemaleSin 2 years ago

Sandy Lee Private Show

HD 2:00 / 31:23

Sandy Lee Private Show

Camster 10 years ago

Sandy Lee Private Show

Sandy Lee Private Show

Flirt4Free 10 years ago

Desire Sweet Private Show

67% HD 2:00 / 4:08

Desire Sweet Private Show

Camster 2 months ago

Patric & Lian & Andres Private Show - Part 3

HD 2:00 / 1:06:56

Patric & Lian & Andres Private Show - Part 3

Flirt4Free 3 years ago

Lisan & Mine Private Show

Lisan & Mine Private Show

Flirt4Free 2 weeks ago

Sophia Loreen Party on Sep 18, 2026 - Part 3

4K 2:00 / 41:13

Sophia Loreen Party on Sep 18, 2026 - Part 3

Flirt4Free 2 weeks ago

Lisan & Mine Private Show

Lisan & Mine Private Show

Flirt4Free 1 week ago

Andres & Hercules & Lian Private Show

64% HD 2:00 / 5:16

Andres & Hercules & Lian Private Show

Flirt4Free 3 years ago

Cuck slave worships Trans Cock featuring Goddess Obsidian

Cuck slave worships Trans Cock featuring Goddess Obsidian

XHamster 2 years ago

Little Serving Sissy Wench

Little Serving Sissy Wench

XHamster 1 year ago

Mike Swift & David Golden Private Show

HD 2:00 / 44:54

Mike Swift & David Golden Private Show

Flirt4Free 2 months ago

Sandy Lee Private Show

Sandy Lee Private Show

Flirt4Free 10 years ago

Sex and Cum with Elias & Elix

33% HD 2:00 / 44:59

Sex and Cum with Elias & Elix

Flirt4Free 1 year ago

Sissy Natasha squirts & piddles out of chastity caged schlong from Lovense sex machine screwing!

Sissy Natasha squirts & piddles out of chastity caged schlong from Lovense sex machine screwing!

ShemaleSin 3 years ago

Angry Conservative Wife Discovers Your Sissy Secret!

Premium HD 8:55

Angry Conservative Wife Discovers Your Sissy Secret!

Sheer 5 months ago

Troy Khalil Private Show

HD 2:00 / 11:43

Troy Khalil Private Show

Flirt4Free 2 years ago

Sandy Lee Private Show

HD 2:00 / 16:02

Sandy Lee Private Show

Flirt4Free 11 years ago

Sandy Lee Plays with Big Toys

Sandy Lee Plays with Big Toys

Camster 9 years ago

Riding my slaves face while he's in chastity_Dragonlady_Sissyslave_Chastity_Cuckold_Dildogag

Riding my slaves face while he's in chastity_Dragonlady_Sissyslave_Chastity_Cuckold_Dildogag

Clips4sale 3 years ago

Sophia Loreen Party on Jul 7, 2026 - Part 4

HD 2:00 / 12:22

Sophia Loreen Party on Jul 7, 2026 - Part 4

Flirt4Free 2 months ago

Sophia Loreen Private Show

4K 2:00 / 21:55

Sophia Loreen Private Show

Camster 1 month ago

Sophia Loreen Private Show

HD 2:00 / 14:59

Sophia Loreen Private Show

Camster 5 years ago

Sophia Loreen Demonstrates Amazing Flexibility

Sophia Loreen Demonstrates Amazing Flexibility

Camster 4 years ago

Alisa Fresh Private Show

Alisa Fresh Private Show

Flirt4Free 3 months ago

Sandy Lee Private Show

HD 2:00 / 24:59

Sandy Lee Private Show

Camster 3 years ago

Cloe & Charlotte Private Show

HD 2:00 / 12:13

Cloe & Charlotte Private Show

Flirt4Free 3 years ago

Sandy Lee Private Show

Sandy Lee Private Show

Camster 10 years ago

Lilit Hot Private Show

Lilit Hot Private Show

Camster 2 weeks ago

Sophia Loreen Private Show

4K 2:00 / 14:39

Sophia Loreen Private Show

Camster 1 month ago

Sandy Lee Has a Large Jell Dildo Anal

Sandy Lee Has a Large Jell Dildo Anal

Camster 9 years ago

William Raven Private Show

HD 2:00 / 19:05

William Raven Private Show

Flirt4Free 5 years ago

Maya Spring Private Show

4K 2:00 / 14:40

Maya Spring Private Show

Camster 3 weeks ago

Sandy Lee Members-Only Show

HD 2:00 / 24:19

Sandy Lee Members-Only Show

Camster 11 years ago

William Raven Private Show

57% HD 2:00 / 30:13

William Raven Private Show

Flirt4Free 4 years ago

William Raven Private Show

William Raven Private Show

Flirt4Free 4 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Camster 2 years ago

Desire Sweet Private Show

Desire Sweet Private Show

Camster 3 weeks ago

Desire Sweet Private Show

HD 2:00 / 16:09

Desire Sweet Private Show

Camster 6 days ago

Sandy Lee Private Show

Sandy Lee Private Show

Camster 11 years ago

Sandy Lee Private Show

Sandy Lee Private Show

Camster 11 years ago

$21 Yr Old Bdsm Slut Gets Tied Up and Dp\'d- Anal, Atm$ HD 2:00 / 11:41

21 Yr Old Bdsm Slut Gets Tied Up and Dp\'d- Anal, Atm

Camster 3 years ago

Cum lube for the cuck sub - Cliff Media Productions

Premium HD 28:56

Cum lube for the cuck sub - Cliff Media Productions

XNXXGold 7 months ago

Lisan & Mine Private Show

Lisan & Mine Private Show

Camster 2 weeks ago

Chastity Rex Word Een Sissy

58% HD 0:39 / 5:32

Chastity Rex Word Een Sissy

FapHouse 8 months ago

Sandy Lee Members-Only Show

61% HD 2:00 / 17:58

Sandy Lee Members-Only Show

Camster 11 years ago

Sophia Loreen Private Show

63% HD 2:00 / 18:12

Sophia Loreen Private Show

Camster 3 months ago

Sandy Lee Private Show

HD 2:00 / 10:14

Sandy Lee Private Show

Camster 10 years ago

Hot Brunette with Great Body Loves to Show Anus

HD 2:00 / 10:00

Hot Brunette with Great Body Loves to Show Anus

Camster 9 years ago

Beta diaper cuck dismantles ego.

Beta diaper cuck dismantles ego.

XHamster 4 years ago

Luna Florez Private Show

Luna Florez Private Show

Camster 2 weeks ago

Sandy Lee Private Show

Sandy Lee Private Show

Camster 3 years ago

Zara Clark Private Show

63% 4K 2:00 / 4:10

Zara Clark Private Show

Camster 10 months ago

Cuckold Pegging Femdom Handjob Cumshot Tease

Cuckold Pegging Femdom Handjob Cumshot Tease

Eporner 3 years ago

Alice Monet Private Show

Alice Monet Private Show

Camster 3 years ago

Sandy Lee Private Show

Sandy Lee Private Show

Camster 11 years ago

Desire Sweet Private Show

55% HD 2:00 / 15:38

Desire Sweet Private Show

Camster 1 week ago

Soon to be Neutered Chastised Sissy Worships Pussy

Soon to be Neutered Chastised Sissy Worships Pussy

TrannyGem 7 years ago

Leaking Thick Cum in Chastity

Leaking Thick Cum in Chastity

XHamster 4 years ago

Lisan & Mine Private Show

62% 4K 2:00 / 44:06

Lisan & Mine Private Show

Flirt4Free 1 week ago

Vicky Katherine Private Show

65% HD 2:00 / 38:12

Vicky Katherine Private Show

Camster 3 years ago

Desire Sweet Private Show

Desire Sweet Private Show

Camster 2 weeks ago

Crossdresser Gets Strapon by Femdom

Crossdresser Gets Strapon by Femdom

Fetishpapa 9 years ago

Luna Florez Private Show

Luna Florez Private Show

Camster 1 week ago

Sandy Lee Members-Only Show - Part 2

HD 2:00 / 49:06

Sandy Lee Members-Only Show - Part 2

Camster 11 years ago

Compilation of sissy cuckold training - Real session with two partners - BBC - Trans woman - Sissy Chastity

HD 0:59 / 32:38

Compilation of sissy cuckold training - Real session with two partners - BBC - Trans woman - Sissy Chastity

Clips4sale 8 months ago

Sidney Puff Private Show

Sidney Puff Private Show

Camster 5 days ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 5 years ago

Sandy Lee Private Show

Sandy Lee Private Show

Camster 11 years ago

Sandy Lee Private Show

61% HD 2:00 / 7:00

Sandy Lee Private Show

Camster 11 years ago

Sandy Lee Private Show

HD 2:00 / 50:12

Sandy Lee Private Show

Camster 3 years ago

Sara & Elver Private Show

Sara & Elver Private Show

Camster 9 months ago

Penis Cage & Pegging for Submissive Husband #871 Fantasy Bisexual Threesome Part 1 Clip 1

Penis Cage & Pegging for Submissive Husband #871 Fantasy Bisexual Threesome Part 1 Clip 1

XHamster 1 year ago

Sissy and Her Chastity Keyholder

Sissy and Her Chastity Keyholder

XHamster 5 months ago

Cum lube for the cuck sub - Cliff Media Productions

Premium HD 28:55

Cum lube for the cuck sub - Cliff Media Productions

Sheer 7 months ago

Desire Sweet Private Show

HD 2:00 / 25:53

Desire Sweet Private Show

Camster 5 days ago

Luna Florez Private Show

4K 2:00 / 3:41:53

Luna Florez Private Show

Camster 1 week ago

Luna Florez Private Show

Luna Florez Private Show

Camster 1 week ago

oiled trans in flat chastity fucked with BBC and squirts cum

oiled trans in flat chastity fucked with BBC and squirts cum

Clips4sale 2 years ago

Sandy Lee Private Show

Sandy Lee Private Show

Camster 10 years ago

Leather corset sissy fucked

Leather corset sissy fucked

Clips4sale 7 months ago

Troy Khalil Private Show

54% HD 2:00 / 6:00

Troy Khalil Private Show

Flirt4Free 2 years ago

Lian & Stivens Private Show

Lian & Stivens Private Show

Flirt4Free 3 years ago

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