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Shemale Dildo Trainer 34:16
Shemale Dildo Trainer
Cock Suck Encouragement 1 08:39
Cock Suck Encouragement 1
ANAL6 10:05
ANAL6
My Cute Anal Whore 10:31
My Cute Anal Whore
Bambi 08:47
Bambi
Sissy Ass Trainer Mind Warp 05:37
Sissy Ass Trainer Mind Warp
Sissy Drills - Tool B 04:58
Sissy Drills - Tool B
Pavlov's Sissy 13:05
Pavlov's Sissy
SissyAline - Train Your Sissy Pussy 09:06
SissyAline - Train Your Sissy Pussy
Anal Training Verbal Instructions Penetration Inspiration 10:32
Anal Training Verbal Instructions Penetration Inspiration
Anal Dildo Hero - The Britney Spears Edition 47:23
Anal Dildo Hero - The Britney Spears Edition
Anal Dildo Hero - Heads and Tails 30:58
Anal Dildo Hero - Heads and Tails
Anal Trainer - By Analana 26:32
Anal Trainer - By Analana
Detailed Guide To Cock Sucking - Stage 1 V1 09:44
Detailed Guide To Cock Sucking - Stage 1 V1
Sissy Drills - Part 49 - Back Level 4 34:05
Sissy Drills - Part 49 - Back Level 4
Insatiable For Cock 04:49
Insatiable For Cock
Your Hypno Goddess - My New Life 10:36
Your Hypno Goddess - My New Life
Detailed Guide To Cock Sucking - Stage 2 08:28
Detailed Guide To Cock Sucking - Stage 2
BounceX - Anal Dildo Hero - Beta Test 24:56
BounceX - Anal Dildo Hero - Beta Test
Sissy Drills - Part 67 - Back Level 8 1:01:36
Sissy Drills - Part 67 - Back Level 8
Pleasure Hole Training 04:11
Pleasure Hole Training
Dildo Hero - Your Girlfriend Needs Some Help 18:46
Dildo Hero - Your Girlfriend Needs Some Help
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
Dildo Hero - Empathy 44:08
Dildo Hero - Empathy
Dildo Hero - Deepthroat Trainer 16:19
Dildo Hero - Deepthroat Trainer
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Sissy Red Light Green Light
Ahegao Cock Sluts 06:34
Ahegao Cock Sluts
Cock Hero - Hentai Hell Edition 40:56
Cock Hero - Hentai Hell Edition
Anal Dildo Hero 24:38
Anal Dildo Hero
Sissy Squad - Field Testing - Sissy Caption Story 12:26
Sissy Squad - Field Testing - Sissy Caption Story
FPOV Hypno 2 05:11
FPOV Hypno 2
Sissy Goals Trainers 21:02
Sissy Goals Trainers
Slut Pop Dildo Hero - Rough Cut Version 0.5 13:55
Slut Pop Dildo Hero - Rough Cut Version 0.5
Face Fuck Training - Heavythird 09:43
Face Fuck Training - Heavythird
TikTok Sluts Love Sucking Cock 02:38
TikTok Sluts Love Sucking Cock
Feminised By An Egirl - Soft Core 07:23
Feminised By An Egirl - Soft Core
Cocksucking Trainer - Portrait 09:05
Cocksucking Trainer - Portrait
Cocksucking Trainer - Landscape 09:05
Cocksucking Trainer - Landscape
Stoplight - Red / Green Light 10:02
Stoplight - Red / Green Light
BounceX Dildo Hero - Vol 1 52:12
BounceX Dildo Hero - Vol 1
Anal Whore Captions 12:54
Anal Whore Captions
Anal Lover Cum Dump - Captions 16:22
Anal Lover Cum Dump - Captions
Slut Pop Dildo Hero 13:53
Slut Pop Dildo Hero
Acting Like A Slut - Caption Story 21:24
Acting Like A Slut - Caption Story
Metronome Throat Trainer 19:52
Metronome Throat Trainer
Sissy Drills - Part 69 - Stand Level 8 57:49
Sissy Drills - Part 69 - Stand Level 8
Hypno Hentai Mindfuck Bimbo 18:17
Hypno Hentai Mindfuck Bimbo
TikTok Cock Sluts 04:08
TikTok Cock Sluts
Analana - Anal Training - Russian 26:35
Analana - Anal Training - Russian
Sissy Anal Training - Anal Dildo Hero - Sissy-Voyeur Experiment - Russian 08:52
Sissy Anal Training - Anal Dildo Hero - Sissy-Voyeur Experiment - Russian
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Anal Hero Simple - 120 BPM By Jeir
Dildo Hero - Poppers Edition 09:05
Dildo Hero - Poppers Edition
Futa Gangbang JOI 32:13
Futa Gangbang JOI
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Anal Hero Simple 2 - 145 BPM By Jeir
Abandon Dildo Hero Instructions 11:18
Abandon Dildo Hero Instructions
Cuckold Game - Rock Paper Scissor 11:21
Cuckold Game - Rock Paper Scissor
Gender Swap Game Show 35:13
Gender Swap Game Show
Fucking Machine Mindbreak 12:53
Fucking Machine Mindbreak
Dildo Hero Short - Gimme More 02:42
Dildo Hero Short - Gimme More
Barbie Transformation Training 06:46
Barbie Transformation Training
Anal Fantasies 1 - Perverted Meditations TTS Edit 06:33
Anal Fantasies 1 - Perverted Meditations TTS Edit
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Babecock - By Nbmogvn
Anal Dildo Hero - You Vs Katrina 32:43
Anal Dildo Hero - You Vs Katrina
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PinkAudioLabs - Cock Sucker Cum Swallower Training
Put It In My Mouth 2 37:46
Put It In My Mouth 2
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Sissy Anal Training - Program - Anal Experience
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NightClub Deepthroat Slut - Guided by Mistress Ameliya
Cock Roulette 05:04
Cock Roulette
Sissy Breaker 03:13
Sissy Breaker
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Mindcontrol - World PMV Games 2023
"Straight" JOI 03:25
"Straight" JOI
Furry Hypnosis JOI 44:17
Furry Hypnosis JOI
Dildo Hero - Choose Your Position 26:29
Dildo Hero - Choose Your Position
Sissy Anal Training - Your Anal Dream - Subbed 15:45
Sissy Anal Training - Your Anal Dream - Subbed
Anal Dildo Hero - The Britney Spears Edition - Remake 47:23
Anal Dildo Hero - The Britney Spears Edition - Remake
Dildo Hero - Dildo And Vibrator 26:56
Dildo Hero - Dildo And Vibrator
Sissy Anal Training - Program - Anal Experience UK Subs 1:15:20
Sissy Anal Training - Program - Anal Experience UK Subs
Plush - Dildo Hero 07:01
Plush - Dildo Hero
NNN Sissy Ballbusting Hero - CBT Instruction 2 03:11
NNN Sissy Ballbusting Hero - CBT Instruction 2
Sissification Exam - The First Exam That Matters 11:54
Sissification Exam - The First Exam That Matters
BounceX Dildo Hero - Vol 2 1:05:29
BounceX Dildo Hero - Vol 2
Anal Gape College - Chapter 1 The First Entery 14:46
Anal Gape College - Chapter 1 The First Entery
My Little Helper - Day 1 - Part 1 40:31
My Little Helper - Day 1 - Part 1
Job Interview - Day 1 - Part 2 47:04
Job Interview - Day 1 - Part 2
Sweet Dreams - Day 1 - Part 3 36:47
Sweet Dreams - Day 1 - Part 3
Bounce - Six Minutes To Sissygasm 06:35
Bounce - Six Minutes To Sissygasm
Bambi spanking deepthroat obeying Training. 35:58
Bambi spanking deepthroat obeying Training.
Love Chastity 04:50
Love Chastity
The Teen Girl's Guide To Sucking Cock - Vol 1 03:38
The Teen Girl's Guide To Sucking Cock - Vol 1
Dildo Hero - You Vs 23 Cocks 25:28
Dildo Hero - You Vs 23 Cocks
Three Lessons - Neekolul Ballbusting Hero PMV 02:54
Three Lessons - Neekolul Ballbusting Hero PMV
Sissy Metamorphosis 03 - Anal Awakening 25:13
Sissy Metamorphosis 03 - Anal Awakening
Cock Suck Addiction 17:29
Cock Suck Addiction
Lets Play With Your Ass - Sissy Anal Training 17:23
Lets Play With Your Ass - Sissy Anal Training
Fucking Machine Vol 4 12:05
Fucking Machine Vol 4
How You Became Obsessed With BBC - Part 1 - Captions 03:12
How You Became Obsessed With BBC - Part 1 - Captions
Femboy Fucktoy - Poppers Trainer 12:29
Femboy Fucktoy - Poppers Trainer
TikTok Fertility Test - Censored Ballbusting Hero 03:58
TikTok Fertility Test - Censored Ballbusting Hero
Ruin 6 57:12
Ruin 6
Sissy Valentines Day 07:08
Sissy Valentines Day
Sissy Training - Part 1 04:17
Sissy Training - Part 1
Eyes Wide Shut 21:44
Eyes Wide Shut
Oral Masturbation Training 15:37
Oral Masturbation Training
Anal Training 1 - Finding Pleasure 06:06
Anal Training 1 - Finding Pleasure
Anal Training Metronome & Cum Countdown 25:03
Anal Training Metronome & Cum Countdown
Faster N Harder - PMV By HoloPMV 02:02
Faster N Harder - PMV By HoloPMV
SIS - 204 Suck Cock 25:54
SIS - 204 Suck Cock
Sissy Mind Fucking Program - By Sissygaljasmine 07:18
Sissy Mind Fucking Program - By Sissygaljasmine
Sissy Training Lesson 2 - Its Just A Little Fun 08:31
Sissy Training Lesson 2 - Its Just A Little Fun
Dildo Hero A Perfect Loop 05:25
Dildo Hero A Perfect Loop
Sissy Training Supervision - Nausea 15:20
Sissy Training Supervision - Nausea
Ass Pussy Hero 1 06:28
Ass Pussy Hero 1
You Love Suck Cock 02:49
You Love Suck Cock
Traffic Light Hypno - Bioxide - Sissy Hypnosis 04:30
Traffic Light Hypno - Bioxide - Sissy Hypnosis
Cock Hero - Clench Trainer - SX Tapes 41:05
Cock Hero - Clench Trainer - SX Tapes
Brand New Bitch - Censored Hero PMV 03:12
Brand New Bitch - Censored Hero PMV
Go Fuck Yourself 2:42:51
Go Fuck Yourself
Sissy Training Lesson 4 - You Have Two 13:50
Sissy Training Lesson 4 - You Have Two
The Spark - PMV 03:11
The Spark - PMV
Follow Along 5 14:15
Follow Along 5
Butt Slut - PMV 01:39
Butt Slut - PMV
Fucking Machine Poppers Edition Transmatica 2 58:37
Fucking Machine Poppers Edition Transmatica 2
Ultimate Tiktok PMV 43:24
Ultimate Tiktok PMV
Bayonetta BBC Hypno - AI Voiced With Poppers 1:04:13
Bayonetta BBC Hypno - AI Voiced With Poppers
Move Your Body - Hero PMV 03:15
Move Your Body - Hero PMV
Inspiration For A Sissy Slut - Dildo Hero Edit 06:18
Inspiration For A Sissy Slut - Dildo Hero Edit
Bounce X A Dildo Hero Video Vol 1 By Yummy 08:24
Bounce X A Dildo Hero Video Vol 1 By Yummy
Ride Along Deluxe - Therapy Corruption 15:00
Ride Along Deluxe - Therapy Corruption
You Have Been Caught 05:04
You Have Been Caught
Step Futa - Futanari Hills Episode 33:48
Step Futa - Futanari Hills Episode
Bouncex Lite Volume 1 - Dildo Hero 22:55
Bouncex Lite Volume 1 - Dildo Hero
Love Anal Bouncex Lite Volume 3 - Dildo Hero 36:42
Love Anal Bouncex Lite Volume 3 - Dildo Hero
Femboy Fucktoy - Poppers Trainer Sound Overlay 12:29
Femboy Fucktoy - Poppers Trainer Sound Overlay
Itss Time To Be Her - Training 13:45
Itss Time To Be Her - Training
BounceX Lite Volume 2 - Dildo Hero 36:57
BounceX Lite Volume 2 - Dildo Hero
Im A Stupid Bimbo - Hentai JOI 28:52
Im A Stupid Bimbo - Hentai JOI
BounceX LITE Dildo Hero Volume 4 PMV Edition 37:07
BounceX LITE Dildo Hero Volume 4 PMV Edition
Dildohero - Noodledude 20:23
Dildohero - Noodledude
Gangbanged By Futa Samus And Friends 36:04
Gangbanged By Futa Samus And Friends
Kawaii 808 - BounceX Dildo Hero 01:40
Kawaii 808 - BounceX Dildo Hero
Fist N Fury - Trainer 13:05
Fist N Fury - Trainer
4 Sides To Me - The Bitch 04:58
4 Sides To Me - The Bitch
Puppy Personality Programmer 07:53
Puppy Personality Programmer
Throat Hero - Deepthroat Trainer By Whore Factory 20:02
Throat Hero - Deepthroat Trainer By Whore Factory
Mindless Bareback Bitch 15:27
Mindless Bareback Bitch
Pure Oral Hentai JOI By Hentirella 28:46
Pure Oral Hentai JOI By Hentirella
Pure Oral Joi Lesson 2 By Hentirella 26:40
Pure Oral Joi Lesson 2 By Hentirella
Whispering Cock Sucking Encouragement 05:20
Whispering Cock Sucking Encouragement
Mars Challenge 1:13:48
Mars Challenge
Slutbeat Wet Dreams - Aroma Edit 08:57
Slutbeat Wet Dreams - Aroma Edit
This Is A Sissy Bounce Along By DropPMV 03:33
This Is A Sissy Bounce Along By DropPMV
Dildo Hero - Poppers Edition - German Voice 09:05
Dildo Hero - Poppers Edition - German Voice
Arent You Straight Bro - Dildo Hero Edit 04:06
Arent You Straight Bro - Dildo Hero Edit
Fem Future - Dildo Hero Edit 03:26
Fem Future - Dildo Hero Edit
Sissy Perfect Trainer by Leyendecker Dildo Hero Edit 05:18
Sissy Perfect Trainer by Leyendecker Dildo Hero Edit
Dildo Hero Subliminal Affirmations - Fuck Yourself As You Become a Hentai Sissy 12:20
Dildo Hero Subliminal Affirmations - Fuck Yourself As You Become a Hentai Sissy
Sissygasms Are Real 05:44
Sissygasms Are Real
Pavlov - Hole 10:25
Pavlov - Hole
Dildo Hero Poppers Furry - S1E1 09:08
Dildo Hero Poppers Furry - S1E1
Ahegao Reprogramming Brainwash - JOI 08:20
Ahegao Reprogramming Brainwash - JOI
Dildo Ass Fucking Training 05:57
Dildo Ass Fucking Training
Anal Challenge 1:58:01
Anal Challenge
Dildo Hero Poppers Furry - S1E2 04:27
Dildo Hero Poppers Furry - S1E2
Futa Mom 1 - Oral Anal Light-Feminization And More - NovaJoi 23:35
Futa Mom 1 - Oral Anal Light-Feminization And More - NovaJoi
Affirmation Mesmerism With A Futa Therapist 17:05
Affirmation Mesmerism With A Futa Therapist
Your First Sissygasm - Dildo Hero 38:32
Your First Sissygasm - Dildo Hero
Your First Sissygasm - Ladies Edition - Dildo Hero 38:32
Your First Sissygasm - Ladies Edition - Dildo Hero
A Detailed Guide To Sucking Cock Part 1 And 2 18:16
A Detailed Guide To Sucking Cock Part 1 And 2
DripPMV - Epic Sissy Bounce Mega PMV 30:41
DripPMV - Epic Sissy Bounce Mega PMV
Throat Annihilation 20:24
Throat Annihilation
How Good Girls Cum 15:14
How Good Girls Cum
Throat Training To Unlock New Levels Of Pleasure 07:47
Throat Training To Unlock New Levels Of Pleasure
Advanced Deepthroat Trainer - Throat Hero By Whore Factory 28:08
Advanced Deepthroat Trainer - Throat Hero By Whore Factory
Training Your Pretty Hole 06:45
Training Your Pretty Hole
Door 11 - Stepsisters Secret - Goon PMV 04:47
Door 11 - Stepsisters Secret - Goon PMV
Cockhero - Dark Fantasy 23:29
Cockhero - Dark Fantasy
Dildo Hero Subliminal - Fuck Yourself As You Become Valmiel 09:37
Dildo Hero Subliminal - Fuck Yourself As You Become Valmiel
Ass Me - Nicole Murkovski - Anal Training Session 44:39
Ass Me - Nicole Murkovski - Anal Training Session
Your Futa Landlords - Hentai Futa JOI 29:02
Your Futa Landlords - Hentai Futa JOI
Simple Dimple Cock Hero PMV 02:30
Simple Dimple Cock Hero PMV
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Keep Unlocking Your Bodys Potential
Obey The Rhythm – Youre Not Just Being Fucked, Youre Being Reshaped 07:13
Obey The Rhythm – Youre Not Just Being Fucked, Youre Being Reshaped
From Plug To Fist - Bambis Sissy Breakdown 11:28
From Plug To Fist - Bambis Sissy Breakdown
BBC Worship Exam 01 - This Is Perfect 07:44
BBC Worship Exam 01 - This Is Perfect
Special Guest In Dvas Stream - Futa JOI 33:36
Special Guest In Dvas Stream - Futa JOI
Cum To Cock Sissy Anal JOI 07:06
Cum To Cock Sissy Anal JOI
Matrix PMV - Dildo Fuck 02:02
Matrix PMV - Dildo Fuck
Beginner Deepthroat Trainer - Throat Hero by Whore Factory 15:26
Beginner Deepthroat Trainer - Throat Hero by Whore Factory
Indebted To A Businessfuta 38:15
Indebted To A Businessfuta
Puppy Posture Programmer 20:04
Puppy Posture Programmer
Sissification Training 808 - When You No Longer Recognize Fourself 10:46
Sissification Training 808 - When You No Longer Recognize Fourself
Anal Dildo Hero - Ciara Collection 20:31
Anal Dildo Hero - Ciara Collection
Ultimate Sissy Trainer 30:43
Ultimate Sissy Trainer
Most Popular Videos - PMV By Dosha 41:15
Most Popular Videos - PMV By Dosha
Split Roast Dildo Hero Edit - IncubusPMV 03:21
Split Roast Dildo Hero Edit - IncubusPMV
Ass Pussy Hero 1 - 2025 Poppers Edition 06:28
Ass Pussy Hero 1 - 2025 Poppers Edition
Expert Anal Challenge 21:34
Expert Anal Challenge
Industrial Deepthroat Trainer - Fuck Machine Throat Hero By Whore Factory 16:05
Industrial Deepthroat Trainer - Fuck Machine Throat Hero By Whore Factory
Program - Anal Experience 1:17:03
Program - Anal Experience
PMV ESissy Beta Safe - Hero Edit 02:48
PMV ESissy Beta Safe - Hero Edit
Biathalounge On The Origin Of Sissies 13:39
Biathalounge On The Origin Of Sissies
Machine Fucked With Nat - HiSmith Edition 26:45
Machine Fucked With Nat - HiSmith Edition
Futa Girlfriends - Stroke That Cock 09:30
Futa Girlfriends - Stroke That Cock
BBC Dildo And Poppers Program - Sissy Instructions PMV 45:47
BBC Dildo And Poppers Program - Sissy Instructions PMV
Door 18 - Goon PMV 05:34
Door 18 - Goon PMV
Splitscreen Anal Trainer 4 - By Dildoslut 05:24
Splitscreen Anal Trainer 4 - By Dildoslut
Bounce On The Wild Side 04:24
Bounce On The Wild Side
Hold it Down - Deepthroat Trainer By Whore Factory 18:46
Hold it Down - Deepthroat Trainer By Whore Factory
File 03 - How Sissies Masturbate - Anal Instructions 15:42
File 03 - How Sissies Masturbate - Anal Instructions
Break Your Brain - Plap Along 05:52
Break Your Brain - Plap Along
Hypnosister - The Rabbit Hole 2 29:04
Hypnosister - The Rabbit Hole 2
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BounceX Lite - Dildo Hero Vol 6 Pt 1
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BounceX Lite - Dildo Hero Vol 6 Pt 2
Deepthroat Hero - Futa Sissy Gloryhole - Tales Of Dominastra - Episode One 31:48
Deepthroat Hero - Futa Sissy Gloryhole - Tales Of Dominastra - Episode One
Youre An Omega 13:09
Youre An Omega
Meow meow - Lustful Loops 03:06
Meow meow - Lustful Loops
Bounce For Mommy Futa - Poppers Mind Fuck 22:00
Bounce For Mommy Futa - Poppers Mind Fuck
Deepthroat Training - Learn With Kate Kuray 13:10
Deepthroat Training - Learn With Kate Kuray
DIldo Hero Ultimate - Pop Star Dominatrix Edition 1:00:45
DIldo Hero Ultimate - Pop Star Dominatrix Edition
Whore Mindset - Deepthroat Submission Trainer By Whore Factory 28:00
Whore Mindset - Deepthroat Submission Trainer By Whore Factory

Anal Challenge

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  • (285)
Wdsg Submitted by wdsg
  • 1:58:01
  • 220213
  • 2025-01-23 03:05:54
It's your last day as a hooker, but you still have a debt to pay to the boss... almost 2 hours of anal/oral play. Have fun!
Tags: dildo, training, toy, anal, Dildo hero, Sissy Training, metronome
Categories: Anal, Movies, Sissy Training
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