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Shemale Dildo Trainer 34:16
Shemale Dildo Trainer
Sissy Anal Trainer 17:12
Sissy Anal Trainer
Anal Dildo Hero - lovelyludwigvan 19:01
Anal Dildo Hero - lovelyludwigvan
Anal Dildo Hero 2 - lovelyludwigvan 18:58
Anal Dildo Hero 2 - lovelyludwigvan
Dildo Hero - Riding The A Train 56:50
Dildo Hero - Riding The A Train
The Holes Are The Plot 00:52
The Holes Are The Plot
Anal Dildo Hero - Crazy Cox Experiment 12:42
Anal Dildo Hero - Crazy Cox Experiment
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 Dildo Hero - The Appetizer Experiment 08:59
Anal Dildo Hero - The Appetizer Experiment
Cock Hero TS Special 01 - Starlets 1:07:25
Cock Hero TS Special 01 - Starlets
Anal Trainer - By Analana 26:32
Anal Trainer - By Analana
Anal Dildo Hero - Sissy-Voyeur Experiment 08:54
Anal Dildo Hero - Sissy-Voyeur Experiment
Dildo Hero - Gang Banged 37:52
Dildo Hero - Gang Banged
Anal Dildo Hero - GloryHole Party 08:24
Anal Dildo Hero - GloryHole Party
Anal Dildo Hero - J`En Ai Marre 05:34
Anal Dildo Hero - J`En Ai Marre
Sissy Dildo Hero Series - Sissy Diaries Day 1 1:00:40
Sissy Dildo Hero Series - Sissy Diaries Day 1
Sissy Dildo Hero - Anal Fisting 53:00
Sissy Dildo Hero - Anal Fisting
Oral Dildo Hero - Bailey's Party 14:44
Oral Dildo Hero - Bailey's Party
Dildo Hero - Riding The A Train - Warmup Only 05:35
Dildo Hero - Riding The A Train - Warmup Only
BounceX - Anal Dildo Hero - Beta Test 24:56
BounceX - Anal Dildo Hero - Beta Test
Cock Hero TS Special 03 - Transdimensional Part 1 55:20
Cock Hero TS Special 03 - Transdimensional Part 1
Cock Hero TS Special 04 - Transdimensional Part 2 1:16:20
Cock Hero TS Special 04 - Transdimensional Part 2
Pleasure Hole Training 04:11
Pleasure Hole Training
Dildo Hero - Empathy 44:08
Dildo Hero - Empathy
Dildo Hero - Deepthroat Trainer 16:19
Dildo Hero - Deepthroat Trainer
Anal Dildo Hero 24:38
Anal Dildo Hero
Slut Pop Dildo Hero - Rough Cut Version 0.5 13:55
Slut Pop Dildo Hero - Rough Cut Version 0.5
Heavythird's - Throat Hero - patreon/heavythirds 14:56
Heavythird's - Throat Hero - patreon/heavythirds
BounceX Dildo Hero - Vol 1 52:12
BounceX Dildo Hero - Vol 1
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Slut Pop Dildo Hero
Cock Hero TS Special 05 - Transdimensional Part 3 1:05:58
Cock Hero TS Special 05 - Transdimensional Part 3
HeavyThird's Sissy Arcades - The Deepthroat Slave - patreon/heavythirds 16:02
HeavyThird's Sissy Arcades - The Deepthroat Slave - patreon/heavythirds
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Anal Hero Simple - 120 BPM By Jeir
Dildo Hero - Poppers Edition 09:05
Dildo Hero - Poppers Edition
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Anal Hero Simple 2 - 145 BPM By Jeir
Abandon Dildo Hero Instructions 11:18
Abandon Dildo Hero Instructions
Fucking Machine JOI 07:55
Fucking Machine JOI
Fucking Machine Mindbreak 12:53
Fucking Machine Mindbreak
Anal Dildo Hero - You Vs Katrina 32:43
Anal Dildo Hero - You Vs Katrina
Dildo Hero - Oral Anal A2M Sissy Training 29:27
Dildo Hero - Oral Anal A2M Sissy Training
Oral Dildo Hero - Cut 2 18:29
Oral Dildo Hero - Cut 2
Oral Dildo Hero - New 12:32
Oral Dildo Hero - New
Rock Paper Scissors 2 18:10
Rock Paper Scissors 2
Dildo Hero - Choose Your Position 26:29
Dildo Hero - Choose Your Position
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Anal Dildo Hero - Super Freaky Girl
Dildo Hero - Your Special Moment 20:52
Dildo Hero - Your Special Moment
Anal Dildo Hero - The Britney Spears Edition - Remake 47:23
Anal Dildo Hero - The Britney Spears Edition - Remake
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Dildo Hero - Dildo And Vibrator
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Klaras Anal Trainer
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Dildo Hero Edit - Tu Trapito Favorito - Fuck Me Too
Dildo Hero - Anal Program 22:08
Dildo Hero - Anal Program
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Edge Challenge - BJ Test
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Plush - Dildo Hero
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BounceX Dildo Hero - Vol 2
Dildo Hero - You Vs 23 Cocks 25:28
Dildo Hero - You Vs 23 Cocks
Intense Anal Training 26:11
Intense Anal Training
Anal Training Metronome & Cum Countdown 25:03
Anal Training Metronome & Cum Countdown
TS Hero - Plugged ruins 45:02
TS Hero - Plugged ruins
Sissy Training 26:32
Sissy Training
Ass To Mouth Training 35:27
Ass To Mouth Training
Dildo Hero - You VS Sophia 45:29
Dildo Hero - You VS Sophia
Dildo Hero - You VS Joey 51:29
Dildo Hero - You VS Joey
Dildo Hero - Ride The A Train - Poppers Edition 57:09
Dildo Hero - Ride The A Train - Poppers Edition
Dildo Hero A Perfect Loop 05:25
Dildo Hero A Perfect Loop
Shemale Dildo Hero 1:45:12
Shemale Dildo Hero
Dildo Hero - You VS Anastasia 39:11
Dildo Hero - You VS Anastasia
Ass Pussy Hero 1 06:28
Ass Pussy Hero 1
Cock Hero - Clench Trainer - SX Tapes 41:05
Cock Hero - Clench Trainer - SX Tapes
Go Fuck Yourself 2:42:51
Go Fuck Yourself
Fucking Machine Transmatica - Poppers Edition 1:18:13
Fucking Machine Transmatica - Poppers Edition
Ass Pussy Hero 1 Popper Edit - Subtitles 06:28
Ass Pussy Hero 1 Popper Edit - Subtitles
Fucking Machine Poppers Edition Transmatica 2 58:37
Fucking Machine Poppers Edition Transmatica 2
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
BounceX Lite Volume 2 - Dildo Hero 36:57
BounceX Lite Volume 2 - Dildo Hero
BounceX LITE Dildo Hero Volume 4 PMV Edition 37:07
BounceX LITE Dildo Hero Volume 4 PMV Edition
Dildohero - Noodledude 20:23
Dildohero - Noodledude
Anal Training 26:32
Anal Training
Anal Gape Training - Hentai Anal JOI By Hentirella 31:42
Anal Gape Training - Hentai Anal JOI By Hentirella
Mars Challenge 1:13:48
Mars Challenge
Butt Lover - Cock Hero 09:03
Butt Lover - Cock Hero
TS Feet - Dildo Hero 22:46
TS Feet - Dildo Hero
Anal Dildo Hero 3 - Suck And Slap - By Ludwigvan 51:04
Anal Dildo Hero 3 - Suck And Slap - By Ludwigvan
Sissy Stretch Trainer - Poppers And Inflatable Plug Training 06:28
Sissy Stretch Trainer - Poppers And Inflatable Plug Training
Sissy Dildo Creampie - Hero Edit 02:04
Sissy Dildo Creampie - Hero Edit
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
I Want To Be A Martian - Dildo Hero 29:35
I Want To Be A Martian - Dildo Hero
Easy And Wild - Hardcore - Dildo Hero 29:42
Easy And Wild - Hardcore - Dildo Hero
Anal Challenge 1:58:01
Anal Challenge
Your First Sissygasm - Dildo Hero 38:32
Your First Sissygasm - Dildo Hero
Beta Bounce - Dildo Hero Edit 04:16
Beta Bounce - Dildo Hero Edit
Splitscreen Dildohero - Mommy Anal 08:07
Splitscreen Dildohero - Mommy Anal
Cock Hero - Erotic Delirium 25:49
Cock Hero - Erotic Delirium
Anal Dildo Hero - Futa Beats By bbp555 47:40
Anal Dildo Hero - Futa Beats By bbp555
Flappy Chicks - Dildo Hero Edit 02:54
Flappy Chicks - Dildo Hero Edit
White Boy Cock Hero - Season 1 Finale - By Pfw2be 26:54
White Boy Cock Hero - Season 1 Finale - By Pfw2be
WhiteBoy Cock Hero Season 5 - Midseason Finale - By Pfw2be 45:02
WhiteBoy Cock Hero Season 5 - Midseason Finale - By Pfw2be
WhiteBoy Cock Hero - Season 5 Finale - By Pfw2be 1:10:37
WhiteBoy Cock Hero - Season 5 Finale - By Pfw2be
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
Edge of Despair 21:27
Edge of Despair
Fucking Machine Vol 5 12:21
Fucking Machine Vol 5
Anal Dildo Hero - Ciara Collection 20:31
Anal Dildo Hero - Ciara Collection
Cock Hero - Shemale Starlets 42:53
Cock Hero - Shemale Starlets
Cock Hero - Shemale Starlets 2 1:03:55
Cock Hero - Shemale Starlets 2
The Ultimate Ruin Challenge - Brainmelter 26:47
The Ultimate Ruin Challenge - Brainmelter
Anal For Feet 2 - Dildo Hero 41:15
Anal For Feet 2 - Dildo Hero
Split Roast Dildo Hero Edit - IncubusPMV 03:21
Split Roast Dildo Hero Edit - IncubusPMV
Expert Anal Challenge 21:34
Expert Anal Challenge
Goon Hero 22:06
Goon Hero
Cum Slut CEI - Dildo Hero 28:09
Cum Slut CEI - Dildo Hero
BounceX Lite - Dildo Hero Vol 6 Pt 1 43:25
BounceX Lite - Dildo Hero Vol 6 Pt 1
BounceX Lite - Dildo Hero Vol 6 Pt 2 49:33
BounceX Lite - Dildo Hero Vol 6 Pt 2
DIldo Hero Ultimate - Pop Star Dominatrix Edition 1:00:45
DIldo Hero Ultimate - Pop Star Dominatrix Edition
First Anal Skills Lesson Part 1- Anal Training Dildo Hero By The Sissy Academy 12:36
First Anal Skills Lesson Part 1- Anal Training Dildo Hero By The Sissy Academy
Deepthroat Hero - Futa Sissy Gloryhole Remaster - Tales Of Dominastra - Episode One - Futamaxxing 31:36
Deepthroat Hero - Futa Sissy Gloryhole Remaster - Tales Of Dominastra - Episode One - Futamaxxing
Sissy Training Challenge 04:18
Sissy Training Challenge
Dildo Chair Training - Deep Anal Endurance For Futa Service 25:16
Dildo Chair Training - Deep Anal Endurance For Futa Service
Full Anal Lesson - Dildo Hero By The Sissy Academy 24:20
Full Anal Lesson - Dildo Hero By The Sissy Academy
Deep Throat Trainer - Preview 10:33
Deep Throat Trainer - Preview

First Anal Skills Lesson Part 1- Anal Training Dildo Hero By The Sissy Academy

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  • 2026-06-10 18:34:49
(This is the first part of the first lesson. The full video is 22 minutes long, with the second part featuring exclusively dildo hero in two new positions. It will be available next Monday on Patreon and will be released publicly a bit later). Our lovely instructor Miss Alarie starts teaching your asses how to handle the vigorous thrusts of a dick. You’re going to listen to every word she says and you’re going to do everything she orders you to do. Get ready to train your mind and body as the first step toward becoming a fully subservient sissy slut! Miss Alarie is a strict teacher, but that doesn't mean she doesn't know how to make her classes fun (at least for her). Follow her lead and give her a great show!

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