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Welcome to the Masturbation Instructions Streaming Site
A valid VidownPass provides access to all Masturbation Instructions videos more than 4 Months old
Click here to display the full masturbationinstructions.com Streaming List Displaying 25 of 26 items
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Jack off Exactly How I Instruct
You are a virgin and you just turned 18. You favorite teacher is so proud of you for getting accepted to all ivy league schools she wants to do something for you. She teases you with her perfect ass and more while she instructs you to jack off.

Year: 2014    Length: 15 minutes       Keywords: BigAss JOEncouragement JoeClips JoiClips Encouragement Guided MasturbationInstruction Milf Cougar Pornstar Caroline CarolinePierce POV Jerkoff jo597
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Sexy Retro Girdle Tease
This clip is for serious retro girdle and panty fans. Caroline catches you watching her wearing an amazing green girdle set. She sees you are really turned on and invites you in and instructs you to jack off for her as she models some of them.

Year: 2014    Length: 17 minutes       Keywords: BigAss Pantyhose-Stockings Girdle JOEncouragement JoeClips JoiClips Encouragement Guided MasturbationInstruction Milf Cougar Pornstar Caroline CarolinePierce POV Jerkoff jo896
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Sexy Nurse Needs a Sperm Sample
Sexy nurse needs a sperm sample from you and tease you with her perfect body as she instructs you how to stroke your cock to get the biggest and best load ever. She counts you down to cum into the test tube.

Year: 2014    Length: 14 minutes       Keywords: NursePlay Feet FootWorship JOEncouragement JoeClips JoiClips Encouragement Guided MasturbationInstruction Milf Cougar Pornstar Caroline CarolinePierce POV Jerkoff AssWorship BigAss jo595
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Your Cock is Sooooooooo Huge
Caroline is teasing you with her ass. The more she teases you the bigger your cock gets. It is like a giant inflating balloon. It grows as big as her arm and thicker than the size of her leg. You erupt in the most amazing orgasm drenching her

Year: 2014    Length: 15 minutes       Keywords: JOEncouragement JoeClips JoiClips Encouragement Guided MasturbationInstruction Milf Cougar Pornstar Caroline CarolinePierce POV Jerkoff AssWorship BigAss jo590
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You are Mommy`s Little Panty Man
You still live at home with your sweet mommy that takes care of you. She knows you love her breasts, legs and heels. She knows you have needs and love to sniff and jack off with her panties. She takes off her panties and has you jack off on them.

Year: 2014    Length: 14 minutes       Keywords: POV Jerkoff Infantilism JOEncouragement JoeClips JoiClips Encouragement Guided MasturbationInstruction Milf Cougar Pornstar Caroline CarolinePierce PantyFetish jo589
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Live Doll Masturbation Instruction
Caroline is a perfect live doll and an amazing masturbation instruction.

Year: 2011    Length: 8 minutes       Keywords: DollFetish MasturbationInstruction Caroline CarolinePierce Milf Cougar Pornstar POV JOEncouragement JoeClips JoiClips Encouragement Jerkoff Guided jo371
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Put a Clean Diaper on and Jack Your Cock for Mummy: Caroline
Your mummy comes home and teaches you how to change your own diaper. She notices you get a hard on in your new diaper and instructs you exactly what to do with it through the diaper while she talks to you like the good baby that you are.

Year: 2011    Length: 10 minutes       Keywords: Infantilism AdultDiaper MasturbationInstruction POV JOEncouragement JoeClips JoiClips Encouragement Jerkoff Guided DiaperFetish Milf Cougar Blonde Pornstar Caroline CarolinePierce jo313
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You are Carolines Cum Eating Cuckold
You will become Carolines caged cum eating cuckold. You will learn to eat your own cum and the cum of others when you are uncaged, Excellent cum eating cuck masturbation instruction

Year: 2011    Length: 11 minutes       Keywords: CumEatingInstruction Humiliation Pornstar Cuckold Caroline CarolinePierce Milf Cougar Humiliation MasturbationInstruction POV JOEncouragement JoeClips JoiClips Encouragement Jerkoff Guided jo305
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5 Minute Humiliation Masturbation Instruction
All humiliation quick masturbation instruction for you men who are quick to cum with smaller than average size cocks. Caroline teases you with her amazing ass

Year: 2011    Length: 5 minutes       Keywords: Humiliation SPH Caroline CarolinePierce Encouragement Jerkoff Guided MasturbationInstruction JOEncouragement JoeClips JoiClips Milf Cougar POV Pornstar jo276
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The Perfect Ass From All Angles
Caroline has the perfect ass that looks amazing from alll angles. She shows it off in a lot of different ways while teasing you with her ass and instructing you to jack off to her perfect ass with a countdown to cum.

Year: 2011    Length: 9 minutes       Keywords: AssWorship Caroline CarolinePierce Encouragement Jerkoff Guided MasturbationInstruction JOEncouragement JoeClips JoiClips Milf Cougar POV Pornstar jo264
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Sexy Slow Detailed Cum Eating Instruction MI
What turns Caroline on is to watch a man eat cum. Since you want to be with her you are going to have to be trained by her to eat your own cum. Very detailed excellent cum eating instruction masturbation instruction.

Year: 2011    Length: 11 minutes       Keywords: CumEatingInstruction Caroline CarolinePierce Encouragement Jerkoff Guided MasturbationInstruction JOEncouragement JoeClips JoiClips POV Pornstar Humiliation Milf Cougar jo260
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You Will Jack Your Cock Exactly as Told
Excellent detailed Masturbation Instruction. You will jack your cock EXACTLY how you are told. Stopping and starting and doing it exactly as she tells you to.

Year: 2010    Length: 11 minutes       Keywords: Encouragement POV Pornstar Jerkoff CockControl Guided MasturbationInstruction J/OEncouragement JoeClips JoiClips Caroline CarolinePierce Vampire Milf Cougar jo209
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Give Me Your Sperm Masturbation Instruction
Caroline wants to get pregnant and demands you jack off for her and give her your sperm. She talks about how much she wants your cum, how to jack off, countdown to cum but kicks you out at the end once she gets the sperm she wants.

Year: 2010    Length: 7 minutes       Keywords: Jerkoff Guided Girdle MasturbationInstruction JOEncouragement JoeClips JoiClips POV Humiliation Caroline CarolinePierce Pornstar Milf Cougar jo190
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Office Humiliation Masturbation Instruction
You are sent to Caroline for a recommendation on what your punishment should be for sexual harassment and having porn on your computer. She has you strip down in her office and she humiliates you. She counts you down to cum and then lick it up.

Year: 2010    Length: 22 minutes       Keywords: SPH Milf Cougar Encouragement Jerkoff Guided MasturbationInstruction JOEncouragement JoeClips JoiClips POV Pornstar Humiliation Caroline CarolinePierce Pantyhose-Stockings CumEatingInstruction jo172
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Carolines Bitch Boy
Caroline makes you get into the bath and jack your cock while you clean your body and your mouth out with soap in preparation to suck her boyfriend off before the date. When you cum she makes you lick it all off.

Year: 2010    Length: 11 minutes       Keywords: Cuckold Milf Cougar Humiliation SPH CumEatingInstruction Caroline CarolinePierce Encouragement Jerkoff Guided MasturbationInstruction J/OEncouragement JoeClips JoiClips POV Pornstar jo167
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Caroline`s Game: Instructions 2
You will be ready for this video once you complete part one. Caroline gives you very detailed instruction on what to do with your cum and takes you step by step through a masturbation instruction.

Year: 2010    Length: 10 minutes       Keywords: Pornstar CumEatingInstruction J/OEncouragement JoeClips JoiClips POV Caroline CarolinePierce Encouragement Guided MasturbationInstruction Humiliation Milf Cougar jo164
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Caroline`s Game: Masturbation Instruction and Preparation 1
Caroline has a plan for your cum. She instructs you on what to do with the different bags of cum. Once this is complete you will be ready for part two.

Year: 2010    Length: 7 minutes       Keywords: Pornstar CumEatingInstruction J/OEncouragement JoeClips JoiClips POV Caroline CarolinePierce Encouragement Guided MasturbationInstruction Humiliation Milf Cougar jo163
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The Perverted Spying Neighbor Masturbation Instruction
Caroline catches you spying on her and invites you over to jack off for her. She gives you a series of tasks (SLAP BALLS, FINGER HOLE ETC). She ends with a countdown to cum wanting you to cum in your own mouth/ face.

Year: 2009    Length: 10 minutes       Keywords: Pornstar CumEatingInstruction J/OEncouragement JoeClips JoiClips POV Caroline CarolinePierce Encouragement Guided MasturbationInstruction Humiliation Milf Cougar jo122
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Cock Toe Comparison (Foot/SPH MI)
Caroline and Taylor discuss how seriously small your cock is by comparing it to her toes. Caroline then give you an excellent Masturbation Instruction discussing your small cock, foot/toe jobs with a countdown to cum.

Year: 2009    Length: 8 minutes       Keywords: Pornstar J/OEncouragement JoeClips JoiClips MasturbationInstruction Caroline CarolinePierce Encouragement Guided SPH Humiliation Milf Cougar Taylor Mistress POV jo118
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I Saw YOU in The Back of Class Today!
You got caught by your teacher jacking off in class ALL WRONG. After class PROPER jackoff instruction with one of the best EVER!

Year: 2009    Length: 7 minutes       Keywords: Pornstar CumEatingInstruction J/OEncouragement JoeClips JoiClips POV Caroline CarolinePierce Encouragement Guided MasturbationInstruction Humiliation Milf Cougar jo117
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Momma Knows You Jack off and Do it All Wrong
Caroline is your momma and now that you are an adult she lets you know she knows you have been jacking off in the other room and do it all wrong. She teaches you step by step how to do it right.

Year: 2009    Length: 6 minutes       Keywords: Pornstar Jerkoff Milf Cougar POV MasturbationInstruction Guided Encouragement Caroline CarolinePierce jo109
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Controlled Timed Masturbation Instruction with Two Endings
Sexy controlling masturbation instruction with two endings one being a detailed cum eating instruction after the credits. Caroline is amazing.

Year: 2009    Length: 6 minutes       Keywords: Pornstar CumEatingInstruction Jerkoff Milf Cougar POV MasturbationInstruction Guided Encouragement Caroline CarolinePierce Humiliation jo100
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Cum Eating Chastity Games
Caroline teases you with a key to your device then she plays wanking games with you. You get lucky at the end and get to cum. The only catch is you have to eat every last drop. Great Wanking Game. Caroline is excellent.

Year: 2009    Length: 11 minutes       Keywords: Pornstar CumEatingInstruction Jerkoff Milf Cougar POV MasturbationInstruction Guided Encouragement Caroline CarolinePierce Humiliation jo099
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Box of Buttons Wanking Game
You Wankers will love this game. Caroline takes complete control of your cock and gives you lots of little cruel tasks. If you don`t cum with her exact COUNTDOWN you will be forced to have blue balls. Check out everything she has in store for you.

Year: 2009    Length: 9 minutes       Keywords: Pornstar Jerkoff Milf Cougar POV MasturbationInstruction Guided Encouragement Caroline CarolinePierce Humiliation jo098
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Remote Controlled Masturbation Instruction
Taylor was not finished shooting her model but her model was ready to leave so she decided to turn her into her robot. Taylor grabs her new device stopping Caroline right in her tracks. This clip contains a great MI with a countdown.

Year: 2009    Length: 9 minutes       Keywords: Pornstar Jerkoff Milf Cougar POV MasturbationInstruction Guided Encouragement Caroline CarolinePierce jo097
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