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Cumslut Training 14:32
Cumslut Training
I Exist For Cock 04:39
I Exist For Cock
Sissy Velvet Underground 2 14:58
Sissy Velvet Underground 2
Warping Your Sissy Brain 01:10
Warping Your Sissy Brain
Cum Lover 40:18
Cum Lover
Nyarlathotep's Cumpilation 06:42
Nyarlathotep's Cumpilation
Sissy Pink Motel 2 20:20
Sissy Pink Motel 2
Sissymaker 03:54
Sissymaker
Sissy Love 2 05:34
Sissy Love 2
Bae Gurlz 05:29
Bae Gurlz
Sissy Anal Slut PMV 2017 03:56
Sissy Anal Slut PMV 2017
Sissy Trainer 2016 03:36
Sissy Trainer 2016
It's Time 07:07
It's Time
Ready For It 03:31
Ready For It
Become a Sissy Cum Dumpster 04:39
Become a Sissy Cum Dumpster
Sissygasm 05:07
Sissygasm
Always Limp 03:08
Always Limp
Sissy Brainwashing 11:42
Sissy Brainwashing
Wanna Fuck Me 07:24
Wanna Fuck Me
Masters Ladyboy Slave 11:41
Masters Ladyboy Slave
Your Future 07:52
Your Future
Mindless Bimbo 05:59
Mindless Bimbo
Psychedelic Music Compilation 2 05:17
Psychedelic Music Compilation 2
Fuck Me 07:18
Fuck Me
Boys Boys Boys 03:55
Boys Boys Boys
For My Popper Sluts 3 10:27
For My Popper Sluts 3
One Night In Pattaya 03:19
One Night In Pattaya
Facial Fever 03:31
Facial Fever
Sissy Swallow 08:51
Sissy Swallow
Cum Obsession 05:56
Cum Obsession
DeepSlutPuppy Episode 6 - Captions 08:04
DeepSlutPuppy Episode 6 - Captions
Go Deeper Sissy 07:06
Go Deeper Sissy
Sissy Hypno Popper Trainer 03:40
Sissy Hypno Popper Trainer
Porno Music 19 11:06
Porno Music 19
I Am A Slave To Cock 14:51
I Am A Slave To Cock
Sissy Chastity Cocklust Trainer by Kaysee21 16:51
Sissy Chastity Cocklust Trainer by Kaysee21
Cock Heavy Wash 07:10
Cock Heavy Wash
Sissy Love 6 06:46
Sissy Love 6
Mantra 07:13
Mantra
Sissy Poppers Hypnose Training 4 20:31
Sissy Poppers Hypnose Training 4
The Sissy Lifestyle 06:41
The Sissy Lifestyle
Loads Of Cum 55:24
Loads Of Cum
Advanced Sissy Conversion 17:04
Advanced Sissy Conversion
Like A Girl 05:37
Like A Girl
Sissy Hypno Addiction HD End 10:56
Sissy Hypno Addiction HD End
Bambi Deeper 07:37
Bambi Deeper
Femboi Faggot Sissymaker Hypno 04:05
Femboi Faggot Sissymaker Hypno
Cock Worship - Juicy Dicks 06:20
Cock Worship - Juicy Dicks
Cock Worship - Juicy Dicks 2 07:40
Cock Worship - Juicy Dicks 2
AmberSis Compilation/Remix Part 2: Cocksucking 22:19
AmberSis Compilation/Remix Part 2: Cocksucking
AmberSis Compilation/Remix Part 3: Anal Training 25:37
AmberSis Compilation/Remix Part 3: Anal Training
AmberSis Compilation/ Remix Part 4: Feminized Whore 18:28
AmberSis Compilation/ Remix Part 4: Feminized Whore
Cock Lover 10:04
Cock Lover
Dirty Cum Sluts 05:25
Dirty Cum Sluts
Broken Limp Clitty 2 04:01
Broken Limp Clitty 2
Sissy Motivation Anal Trainer 17:31
Sissy Motivation Anal Trainer
Go Deeper, Sissy! By PopperPrincess 04:58
Go Deeper, Sissy! By PopperPrincess
No Pussy For Sissies - Lesson 20 05:31
No Pussy For Sissies - Lesson 20
A Sissy For Life - Lesson 14 09:10
A Sissy For Life - Lesson 14
Sissy Living By Jenn Love 13:58
Sissy Living By Jenn Love
Pro Sissy Training 1 32:52
Pro Sissy Training 1
Tasty Cum 04:49
Tasty Cum
Sissy Hypno - Cock Craving 02:36
Sissy Hypno - Cock Craving
Another Sissy Recovery 05:23
Another Sissy Recovery
Sissy Cock PMV (feat. HyunA) 03:42
Sissy Cock PMV (feat. HyunA)
SissyHypnoTrippin Vol6 08:16
SissyHypnoTrippin Vol6
Thirsty Cumslut Hypno 04:30
Thirsty Cumslut Hypno
I Love Big Cocks Sissy Hypno 10:00
I Love Big Cocks Sissy Hypno
Broken Limp Clitty Maker 3 04:23
Broken Limp Clitty Maker 3
Soft And Limp Clitty Hypno 04:14
Soft And Limp Clitty Hypno
Blow Your Mind - Mwah 03:04
Blow Your Mind - Mwah
Dildo Pleasure 07:31
Dildo Pleasure
Simple Sissy Recovery 10:12
Simple Sissy Recovery
Sissymaker - I Want Bass 02:54
Sissymaker - I Want Bass
Trap Nation - Gargantua4 03:04
Trap Nation - Gargantua4
SissyAline - Train Your Sissy Pussy 09:06
SissyAline - Train Your Sissy Pussy
SissyAline - Limp And Small 10:29
SissyAline - Limp And Small
I Know What You Really Want - AlineSissy 07:37
I Know What You Really Want - AlineSissy
Sissyfication Acceptance For Cute Sissies 05:42
Sissyfication Acceptance For Cute Sissies
Sissy Slave Castration Sissy Hypno 03:39
Sissy Slave Castration Sissy Hypno
Sissy Hypno 1 - Accepting Your Destiny 11:37
Sissy Hypno 1 - Accepting Your Destiny
Sissy Hypno 2 - Becoming A Cock Slut 15:35
Sissy Hypno 2 - Becoming A Cock Slut
Sissy Chastity Training - PMV 03:44
Sissy Chastity Training - PMV
The Sissyfication Process - SissyBoi4Daddy 22:42
The Sissyfication Process - SissyBoi4Daddy
Hypno Rko - I Knew it Your Dick Is Still Hard 09:02
Hypno Rko - I Knew it Your Dick Is Still Hard
Dont Dream of Her Become Her - Black Sissy Hypno 2 12:22
Dont Dream of Her Become Her - Black Sissy Hypno 2
Part 4 - How Your Night Ends 05:00
Part 4 - How Your Night Ends
Part 5 - Daddy Was Here 05:00
Part 5 - Daddy Was Here
Part 6 - Dick Vs Clitty 05:00
Part 6 - Dick Vs Clitty
Pop That Pussy 03:40
Pop That Pussy
Your True Purpose Sissy - PMV 2 03:26
Your True Purpose Sissy - PMV 2
Part 8 - Your Reward 05:00
Part 8 - Your Reward
Twerk Lesson Sissy PMV 3 03:21
Twerk Lesson Sissy PMV 3
Stare At The Red Dot 07:30
Stare At The Red Dot
Part 9 - Sissy Snacks 05:00
Part 9 - Sissy Snacks
World PMV Games 2021 - Let's Do It 02:18
World PMV Games 2021 - Let's Do It
Part 10 - Locked For Cock 10:00
Part 10 - Locked For Cock
Insatiable For Cock 04:49
Insatiable For Cock
I Love Cock ASMR 04:31
I Love Cock ASMR
CEI ASMR 08:15
CEI ASMR
Sissy Hypno 4 - Cum Lover 10:16
Sissy Hypno 4 - Cum Lover
Black Cock Sleeve - Sissy Cravings 06:17
Black Cock Sleeve - Sissy Cravings
Part 13 - I'm Ready Daddy 07:32
Part 13 - I'm Ready Daddy
Sissy Chastity Trainer - 1 10:25
Sissy Chastity Trainer - 1
Sissy Hero 03:53
Sissy Hero
The PMV League SZN2 Entry 01:36
The PMV League SZN2 Entry
Cum Trap 03:33
Cum Trap
Sissy Education - Chastity 07:28
Sissy Education - Chastity
Smack My Sissy Up - PMV 05:47
Smack My Sissy Up - PMV
Pleasure Hole Training 04:11
Pleasure Hole Training
Take Over Control 03:52
Take Over Control
Splitscreen Anal Trainer 1 - By Dildoslut 05:34
Splitscreen Anal Trainer 1 - By Dildoslut
Splitscreen Anal Trainer 2 - By Dildoslut 05:26
Splitscreen Anal Trainer 2 - By Dildoslut
Splitscreen Anal Trainer 3 - By Dildoslut 05:58
Splitscreen Anal Trainer 3 - By Dildoslut
Part 20 - My Hole 05:00
Part 20 - My Hole
Dildo In Your Sissy Hole 06:02
Dildo In Your Sissy Hole
Cum Trap 2 02:35
Cum Trap 2
Deeper Sissy 10:26
Deeper Sissy
Part 21 - Bend Over 11:00
Part 21 - Bend Over
White Boys Home Alone - Sissy Indoctrinator By @drippmv 01:13
White Boys Home Alone - Sissy Indoctrinator By @drippmv
Sissy Cum 06:47
Sissy Cum
The Sissy Bounce Along - Hypno Dildo Femboy Instructional 02:02
The Sissy Bounce Along - Hypno Dildo Femboy Instructional
Twice - Scientist Poppers PMV 05:19
Twice - Scientist Poppers PMV
Cum Trap 4 05:43
Cum Trap 4
Cum Trap 5 04:33
Cum Trap 5
Transnectar 03:35
Transnectar
Cum Trap 6 03:52
Cum Trap 6
Cum Trap 8 04:42
Cum Trap 8
Twice - The Feels Poppers PMV 06:16
Twice - The Feels Poppers PMV
Slut Pop Dildo Hero - Rough Cut Version 0.5 13:55
Slut Pop Dildo Hero - Rough Cut Version 0.5
Cum Trap Gooner Edition 37:21
Cum Trap Gooner Edition
I'm A Sissy Slut 02:53
I'm A Sissy Slut
Slut Pop Dildo Hero 13:53
Slut Pop Dildo Hero
Your Own Sweet Sissy Sex Slave 19:26
Your Own Sweet Sissy Sex Slave
Breaking In A Sissy 43:26
Breaking In A Sissy
Suckn & Fuckn - Splitscreen Hypno 11:52
Suckn & Fuckn - Splitscreen Hypno
Cum Trap - Gooner Edition 2 25:23
Cum Trap - Gooner Edition 2
Lil Baby Anthony Loves The BNWO 05:12
Lil Baby Anthony Loves The BNWO
Femboy Love 04:07
Femboy Love
Goon Tard 11:58
Goon Tard
Femboy Friday Sadism 04:07
Femboy Friday Sadism
Cum Trap 11 07:16
Cum Trap 11
One Two & Zero16 Loop 00:57
One Two & Zero16 Loop
Femboy Friday Yeah 12:50
Femboy Friday Yeah
Sissy Poppers Hypnose Training III - German 21:45
Sissy Poppers Hypnose Training III - German
Be Careful Sissy 05:12
Be Careful Sissy
Satisfaction 2022 05:46
Satisfaction 2022
The Ultimate Cum Craving By XandraPL 08:15
The Ultimate Cum Craving By XandraPL
Treat Me Like A Slut - PMV 2023 07:45
Treat Me Like A Slut - PMV 2023
Aren't You Straight Bro? 04:06
Aren't You Straight Bro?
Sissygasms Ballbusting And Chastity PMV 08:08
Sissygasms Ballbusting And Chastity PMV
Sissy Goon Journey - Chapter 2 Dildos And Dares 14:40
Sissy Goon Journey - Chapter 2 Dildos And Dares
Scream & Shout - TS PMV 07:27
Scream & Shout - TS PMV
Sissy Goon Journey - Chapter 4 Be A Sissy Slut For Mommy 12:20
Sissy Goon Journey - Chapter 4 Be A Sissy Slut For Mommy
BBC Baby Sissy Bi-Confusion 03:55
BBC Baby Sissy Bi-Confusion
BBC Craving 4 Girls And Bois 16:43
BBC Craving 4 Girls And Bois
The Feminiser By DripPMV & GymBunnyStephanie 06:16
The Feminiser By DripPMV & GymBunnyStephanie
Epic Femboy PMV 12:45
Epic Femboy PMV
Sissygasm PMV 07:42
Sissygasm PMV
Cock 09:02
Cock
Cock Tip Licking Worship 04:29
Cock Tip Licking Worship
Naughty Gurl - TS PMV 07:45
Naughty Gurl - TS PMV
Solo 00:53
Solo
Ai Preto - Brazilian Funk Interracial Sex 02:14
Ai Preto - Brazilian Funk Interracial Sex
Suck Trap Dick - Unholy By brainfuck 02:41
Suck Trap Dick - Unholy By brainfuck
Unholy Sissy - TS PMV 06:05
Unholy Sissy - TS PMV
De 4 Eu Jogo O Rabo - Funk Carioca - Brazil 02:34
De 4 Eu Jogo O Rabo - Funk Carioca - Brazil

Pleasure Hole Training

  • 90%
  • (336)
Ash9689 Submitted by ash9689
  • 04:11
  • 128669
  • 2022-02-02 00:02:07
Music: Only Girl (In The World) - Rihanna Girls featured in the videos (no timestamp): - youngwoozzz - thebubblebumbutt - smolboimoisty - Lily Star - Ana Nomie - VanillaTrap - RMP41069 - mingsuwu -Andylynn Payne - Khloe Kay
Tags: dildohero, analhero, dildo hero, anal hero
Categories: Anal, Movies, Music/PMV, Sissygasm, Toys
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