Chastity Videos - Gay (22,785)

Slow and Deep in My Sissy Ass After Practicing Blowjob 1

Slow and Deep in My Sissy Ass After Practicing Blowjob 1

FapHouse 22 hours ago

Dialexandro Jones Private Show

HD 2:00 / 15:45

Dialexandro Jones Private Show

Flirt4Free 2 years ago

Fucthebitch - Season 1 F6 50 Days Chastity the Sexeperience

HD 1:01 / 16:45

Fucthebitch - Season 1 F6 50 Days Chastity the Sexeperience

FapHouse 2 weeks ago

Hogtied Chastity Twink Struggle to Get Free

HD 0:39 / 11:17

Hogtied Chastity Twink Struggle to Get Free

FapHouse 2 weeks ago

New Vacuum Bed

FapHouse 2 days ago

Milton Jake Private Show

Milton Jake Private Show

Flirt4Free 3 years ago

Training the Collared Chastity Boy Pt 4

61% 0:39 / 17:48

Training the Collared Chastity Boy Pt 4

FapHouse 2 weeks ago

Boy Is Turned Into a Foot-sniffing Sissy by Jocks

42% 1:01 / 5:11

Boy Is Turned Into a Foot-sniffing Sissy by Jocks

FapHouse 2 weeks ago

BDSM - GAY Chastity Sub Handcuffed to the Wall with Ball Gag & Ass Vibrator – Feeds Me Grapes While I Control His Toy

BDSM - GAY Chastity Sub Handcuffed to the Wall with Ball Gag & Ass Vibrator – Feeds Me Grapes While I Control His Toy

Clips4sale 1 week ago

Locktober begins tonight 🔒

Locktober begins tonight 🔒

Clips 1 week ago

Training the Collared Chastity Boy Pt 1

Training the Collared Chastity Boy Pt 1

FapHouse 3 weeks ago

Mdf:: I’ll Pound You Till We Cum

69% 0:39 / 10:32

Mdf:: I’ll Pound You Till We Cum

FapHouse 2 months ago

Colombian Boys Private Show

63% HD 2:00 / 4:11

Colombian Boys Private Show

Flirt4Free 2 weeks ago

Aiden Ward Fist Jona Ortiz

73% 1:01 / 21:27

Aiden Ward Fist Jona Ortiz

FapHouse 5 months ago

Caged Boy Part 2

51% HD 1:01 / 7:57

Caged Boy Part 2

FapHouse 1 month ago

Walking Dickless Through the City (chastity, Fufu-clip)

68% HD 0:08 / 0:40

Walking Dickless Through the City (chastity, Fufu-clip)

FapHouse 8 months ago

Mdf:: I’ll Pound You Till We Cum

74% 1:01 / 10:32

Mdf:: I’ll Pound You Till We Cum

FapHouse 2 months ago

Deadpool Got Caught, and There’s Nowhere Left to Run

55% HD 1:01 / 25:58

Deadpool Got Caught, and There’s Nowhere Left to Run

FapHouse 1 month ago

Caged and Stretched: a Sub's Journey to Prolapse Pleasure

62% HD 1:01 / 23:41

Caged and Stretched: a Sub's Journey to Prolapse Pleasure

FapHouse 1 year ago

College Boy Pup Slave Training Bondage

61% HD 1:01 / 5:10

College Boy Pup Slave Training Bondage

FapHouse 7 months ago

Pantieboy Tucked and Taped in Lingerie Riding BBC Dildo. Hands Free Cum Several Times

Pantieboy Tucked and Taped in Lingerie Riding BBC Dildo. Hands Free Cum Several Times

FapHouse 3 days ago

I brought something for you

Premium HD 26:24

I brought something for you

XVideosRed 4 days ago

Getting Stupid Gonzo Goony on Stepdad’s Cock, Part 2 with Jpeightninezero

55% HD 1:01 / 24:49

Getting Stupid Gonzo Goony on Stepdad’s Cock, Part 2 with Jpeightninezero

FapHouse 3 days ago

50 Days Chastity the Sexeperience

HD 1:01 / 20:33

50 Days Chastity the Sexeperience

FapHouse 1 week ago

First time in chastity

66% 1:07 / 35:54

First time in chastity

ChristianWilde 1 year ago

Twink Gets to Strip and Whorship Feet in Prison

51% 1:01 / 5:27

Twink Gets to Strip and Whorship Feet in Prison

FapHouse 1 month ago

cagedmask & roughdomtopxxx used. owned. no regrets.

67% HD 0:30 / 27:07

cagedmask & roughdomtopxxx used. owned. no regrets.

AnalVids 6 months ago

Chastity Verbal Sph

58% 1:01 / 5:40

Chastity Verbal Sph

FapHouse 9 months ago

MILITARY SERVICE - Hot Soldiers in Action

62% HD 0:24 / 26:25

MILITARY SERVICE - Hot Soldiers in Action

DarkCruising 2 years ago

Cumdumps Need Love Too

66% HD 1:01 / 41:17

Cumdumps Need Love Too

FapHouse 8 months ago

My Hole Looks Horny Today

74% HD 1:01 / 11:49

My Hole Looks Horny Today

FapHouse 2 years ago

POV - Chastity Is Your Life Now

POV - Chastity Is Your Life Now

FapHouse 2 weeks ago

New Vacuum Bed

FapHouse 2 days ago

Cagedmask & Robertroyal Chastity Locked, Ass Locked, and I’m Nothing, Just Holes to Fill

67% HD 1:01 / 16:01

Cagedmask & Robertroyal Chastity Locked, Ass Locked, and I’m Nothing, Just Holes to Fill

FapHouse 5 months ago

POV - Chastity Is Your Life Now

POV - Chastity Is Your Life Now

FapHouse 2 weeks ago

Parole Humiliator Part 1: Pierce Paris and Dale Savage

64% HD 1:01 / 26:52

Parole Humiliator Part 1: Pierce Paris and Dale Savage

FapHouse 2 weeks ago

Colombian Boys Private Show

67% HD 2:00 / 20:55

Colombian Boys Private Show

Flirt4Free 1 month ago

Big Bugle

60% HD 2:00 / 4:39

Flirt4Free 4 years ago

Teasing Broken The Slave's Locked and Frustrated Cock (4K)

69% 4K 0:24 / 17:08

Teasing Broken The Slave's Locked and Frustrated Cock (4K)

Clips4sale 1 year ago

Jeremy Drake Private Show

HD 2:00 / 10:46

Jeremy Drake Private Show

Flirt4Free 1 day ago

Spiked Trainers Bastinado HD

HD 0:11 / 18:15

Spiked Trainers Bastinado HD

Clips4sale 2 years ago

Total Sub Gets Used by Massive Stepdaddy

71% HD 0:39 / 28:14

Total Sub Gets Used by Massive Stepdaddy

FapHouse 4 weeks ago

Brat in Chastity Cage Gets Teased by Hot Police Officer

59% HD 0:39 / 5:07

Brat in Chastity Cage Gets Teased by Hot Police Officer

FapHouse 2 months ago

POV - Locktober Week Three - Objectification Is The Focus (4K)

62% 4K 0:23 / 16:23

POV - Locktober Week Three - Objectification Is The Focus (4K)

Clips4sale 1 year ago

Bareback Rough Fuck Smooth Caged Submissive Twink

62% HD 1:01 / 44:45

Bareback Rough Fuck Smooth Caged Submissive Twink

FapHouse 11 months ago

October 2026 Live -- Spit-soaked Ricky Cage Deepthroats Dick for an Hour!

HD 1:01 / 1:05:47

October 2026 Live -- Spit-soaked Ricky Cage Deepthroats Dick for an Hour!

FapHouse 6 days ago

Tight Sissy Hole Stretched by Real Cock 2

Tight Sissy Hole Stretched by Real Cock 2

FapHouse 1 week ago

Completely Tied Twinks Tries to Cum in Chastity

HD 0:39 / 14:17

Completely Tied Twinks Tries to Cum in Chastity

FapHouse 1 day ago

Christian Levine Party on Oct 15, 2026 - Part 3

4K 2:00 / 38:48

Christian Levine Party on Oct 15, 2026 - Part 3

Flirt4Free 1 day ago

Chastity Guy Tied to the Bed, Allowed to Cum and Locked Again

69% HD 1:01 / 23:49

Chastity Guy Tied to the Bed, Allowed to Cum and Locked Again

FapHouse 3 weeks ago

Fucthebitch Season 1

HD 1:01 / 20:48

Fucthebitch Season 1

FapHouse 2 days ago

Completely Tied Twinks Tries to Cum in Chastity

HD 1:01 / 14:17

Completely Tied Twinks Tries to Cum in Chastity

FapHouse 1 day ago

Monyel Brentt Private Show

Monyel Brentt Private Show

Flirt4Free 1 day ago

Muscle Bottom Ass Play

64% HD 0:39 / 20:26

Muscle Bottom Ass Play

FapHouse 2 months ago

Yes, Sir

42% VR 1:17 / 40:24

VirtualRealGay 8 months ago

Parole Humiliator Part 1: Pierce Paris and Dale Savage

65% HD 0:39 / 26:52

Parole Humiliator Part 1: Pierce Paris and Dale Savage

FapHouse 2 weeks ago

Ice Torment - Bound Gods Live Show

Premium 63% HD 1:29:27

Ice Torment - Bound Gods Live Show

KinkMen 11 years ago

Viking Prisoner Roleplay

50% HD 2:00 / 7:20

Viking Prisoner Roleplay

Flirt4Free 2 years ago

Training the Collared Chastity Boy Pt 4

67% 1:01 / 17:48

Training the Collared Chastity Boy Pt 4

FapHouse 2 weeks ago

Massive Stepdaddy Completely Dominates Sexy Slut

Massive Stepdaddy Completely Dominates Sexy Slut

FapHouse 2 weeks ago

Hairy Otter Became My Whore - Part 1

66% HD 1:01 / 21:18

Hairy Otter Became My Whore - Part 1

FapHouse 11 months ago

Stepdaddy Dan Breeds Locked Asian Twink Sub Lucka - He Shoots His Creamy Wad All Over His Face

56% HD 1:01 / 18:07

Stepdaddy Dan Breeds Locked Asian Twink Sub Lucka - He Shoots His Creamy Wad All Over His Face

FapHouse 1 month ago

Hogtied Chastity Twink Struggle to Get Free

54% HD 1:01 / 11:17

Hogtied Chastity Twink Struggle to Get Free

FapHouse 2 weeks ago

Nasty Cop and the Sex Offender

60% HD 0:39 / 1:06:41

Nasty Cop and the Sex Offender

FapHouse 9 months ago

Football Coach Will Keep You in Chastity

Football Coach Will Keep You in Chastity

FapHouse 1 week ago

POV - Post Orgasm Torment Will Be Routine for You

POV - Post Orgasm Torment Will Be Routine for You

FapHouse 1 week ago

A Femboy Riding an Big, Transparent Clear Dildo and Uses a Vibrator

A Femboy Riding an Big, Transparent Clear Dildo and Uses a Vibrator

FapHouse 1 month ago

Cagedmask[unmasked] X Qmoorexxx Part1

Cagedmask[unmasked] X Qmoorexxx Part1

FapHouse 3 weeks ago

extreme fisting caged prostate squirt & bareback creampie hot daddies camilo brown & rigo avela

HD 0:30 / 35:12

extreme fisting caged prostate squirt & bareback creampie hot daddies camilo brown & rigo avela

PissVids 3 months ago

Mdf: Danny Bound and Milked on the Terrace

53% 1:01 / 12:02

Mdf: Danny Bound and Milked on the Terrace

FapHouse 1 week ago

Dr Baker Conducts a Prostate Massage on the Chastity Slave (4k)

58% 4K 1:01 / 19:19

Dr Baker Conducts a Prostate Massage on the Chastity Slave (4k)

FapHouse 8 months ago

Training the Collared Chastity Boy Pt 3

63% 1:01 / 17:34

Training the Collared Chastity Boy Pt 3

FapHouse 3 weeks ago

Caged Piss Squirting Bottom Getting His Cunt Fist Wrecked by Huge BBC

76% HD 1:01 / 30:27

Caged Piss Squirting Bottom Getting His Cunt Fist Wrecked by Huge BBC

FapHouse 8 months ago

Hooded, Used, Sent Home

HD 0:39 / 35:33

Hooded, Used, Sent Home

FapHouse 3 weeks ago

Boy Is Turned Into a Foot-sniffing Sissy by Jocks

53% 0:39 / 5:11

Boy Is Turned Into a Foot-sniffing Sissy by Jocks

FapHouse 2 weeks ago

Cum And Piss On My Cage Then Diaper Me

70% 0:30 / 15:49

Cum And Piss On My Cage Then Diaper Me

Clips4sale 1 year ago

Femboy Cums Through Flat Chastity with Butt Plug

Femboy Cums Through Flat Chastity with Butt Plug

FapHouse 1 month ago

Slut Gets Spunked in Both Holes

63% HD 1:01 / 16:37

Slut Gets Spunked in Both Holes

FapHouse 1 year ago

Ricck Smith Premiere Show

66% 4K 2:00 / 32:31

Ricck Smith Premiere Show

Flirt4Free 3 weeks ago

this femboy has one of of the most extreme belly bulges you will ever see

Premium HD 14:03

this femboy has one of of the most extreme belly bulges you will ever see

XNXXGold 2 weeks ago

Mdf:: Nikki Locked, Bound and Made to Cum!

57% 0:39 / 14:36

Mdf:: Nikki Locked, Bound and Made to Cum!

FapHouse 6 months ago

Samuel & Zeuv Private Show

49% 4K 2:00 / 32:56

Samuel & Zeuv Private Show

Flirt4Free 1 year ago

Zack Blitz Private Show

55% 4K 2:00 / 8:52

Zack Blitz Private Show

Flirt4Free 1 week ago

Puppy Twink Sub in Chastity Ordered to Ride a Dildo

57% HD 1:01 / 10:06

Puppy Twink Sub in Chastity Ordered to Ride a Dildo

FapHouse 1 week ago

Two Chastity Twinks Get Teased

Two Chastity Twinks Get Teased

FapHouse 2 months ago

Gym Locker Rooms Chastity Cage and Dildo in Car

Gym Locker Rooms Chastity Cage and Dildo in Car

FapHouse 2 weeks ago

Twink Slave Bound in Pallet Wrap for Orgasm Control

Twink Slave Bound in Pallet Wrap for Orgasm Control

FapHouse 2 weeks ago

sexy guy in chastity (teaser)

Premium HD 0:43

sexy guy in chastity (teaser)

XNXXGold 1 week ago

Tommy Iron Party on Dec 27, 2020

66% HD 2:00 / 1:29:52

Tommy Iron Party on Dec 27, 2020

Flirt4Free 5 years ago

Fuck and Fist Caged Submissive Bottom

66% HD 1:01 / 48:52

Fuck and Fist Caged Submissive Bottom

FapHouse 2 years ago

Edging Game JOI - Orgasm Denied

HD 1:01 / 10:56

Edging Game JOI - Orgasm Denied

FapHouse 4 weeks ago

Come Join Me, a Femboy, Having Fun with My Dildo in a Bathtub

HD 0:39 / 16:18

Come Join Me, a Femboy, Having Fun with My Dildo in a Bathtub

FapHouse 1 month ago

Mdf: Danny Bound and Milked on the Terrace

Mdf: Danny Bound and Milked on the Terrace

FapHouse 1 week ago

Fucthebitch - Season

HD 1:01 / 26:00

Fucthebitch - Season

FapHouse 1 week ago

Getting Used and Drained at Motel X

55% HD 1:01 / 1:00:33

Getting Used and Drained at Motel X

FapHouse 2 months ago

Dildo Session in the Terrace and Jerk off Prince Albert

55% HD 1:01 / 15:21

Dildo Session in the Terrace and Jerk off Prince Albert

FapHouse 1 week ago

Twink Gets Tickled by Machine

Premium HD 6:39

Twink Gets Tickled by Machine

this femboy has one of of the most extreme belly bulges you will ever see

Premium HD 14:03

this femboy has one of of the most extreme belly bulges you will ever see

XVideosRed 2 weeks ago

Jord James & Harv Bridgestone Private Show

Jord James & Harv Bridgestone Private Show

Flirt4Free 4 years ago

Patric & Simon & Frederick Private Show

57% HD 2:00 / 11:22

Patric & Simon & Frederick Private Show

Flirt4Free 2 years ago

Zack Blitz Private Show

4K 2:00 / 29:34

Zack Blitz Private Show

Flirt4Free 4 weeks ago

Pathetic Tongue Awaits Master Cum

Pathetic Tongue Awaits Master Cum

Clips4sale 1 week ago

POV Tom Baker - Your Cock Is Disgusting (4k)

66% 4K 1:01 / 6:28

POV Tom Baker - Your Cock Is Disgusting (4k)

FapHouse 9 months ago

Caged Boy Part 4

63% HD 1:01 / 6:54

Caged Boy Part 4

FapHouse 2 weeks ago

LOGAN'S TRIPLE LOAD RETURN [PP TRAINING]

HD 0:30 / 22:06

LOGAN'S TRIPLE LOAD RETURN [PP TRAINING]

Clips4sale 2 weeks ago

Encouraged Bi Cock Sucking Lesson

Premium HD 11:02

Encouraged Bi Cock Sucking Lesson

Sheer 1 week ago

Fucthebitch - Season 1 F12 50 Days

HD 1:01 / 19:20

Fucthebitch - Season 1 F12 50 Days

FapHouse 1 week ago

Simon & Jack & Juseph Private Show

52% HD 2:00 / 8:33

Simon & Jack & Juseph Private Show

Flirt4Free 2 years ago

Gym Locker Rooms Chastity Cage and Dildo in Car

HD 1:01 / 12:08

Gym Locker Rooms Chastity Cage and Dildo in Car

FapHouse 2 weeks ago

50 Days Chastity the Sexeperience

HD 1:01 / 17:04

50 Days Chastity the Sexeperience

FapHouse 1 week ago

chastity locked Pup Davey rides huge fantasy toys and prolapses

Premium HD 25:02

chastity locked Pup Davey rides huge fantasy toys and prolapses

XVideosRed 1 year ago

Adan Reilly Private Show

4K 2:00 / 27:47

Adan Reilly Private Show

Flirt4Free 1 month ago

Zack Blitz Private Show

4K 2:00 / 26:39

Zack Blitz Private Show

Flirt4Free 2 weeks ago

50 Days Chastity the Sexeperience

HD 0:39 / 20:33

50 Days Chastity the Sexeperience

FapHouse 1 week ago

Ricck Smith Premiere Show

57% 4K 2:00 / 3:51

Ricck Smith Premiere Show

Flirt4Free 2 weeks ago

Patric & Enzon Private Show

Patric & Enzon Private Show

Flirt4Free 4 weeks ago

Friendly Guy Chats in Tank Top

66% HD 2:00 / 6:55

Friendly Guy Chats in Tank Top

Flirt4Free 9 years ago

Patric & Enzon Private Show

53% HD 2:00 / 23:13

Patric & Enzon Private Show

Flirt4Free 5 months ago

Extreme Fisting, Caged, Prostate Squirt & Bareback Creampie Hot Daddies Camilo Brown & Rigo Avela

62% HD 0:39 / 35:18

Extreme Fisting, Caged, Prostate Squirt & Bareback Creampie Hot Daddies Camilo Brown & Rigo Avela

FapHouse 4 months ago

En su vida privada es un honorable padre de familia y en el mundo del porno gay es toda una puta caliente con su cl&iacute_toris enjaulado que mama verga y se la meten a pelo

Premium HD 10:37

En su vida privada es un honorable padre de familia y en el mundo del porno gay es toda una puta caliente con su cl&iacute_toris enjaulado que mama verga y se la meten a pelo

XNXXGold 2 weeks ago

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