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Click any keyword to display a subset of the full streaming list	Displaying 25 of 614 items

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Will You Get to Cum? Will You Have to Eat It???

If you get to cum and if you will have to eat it will be determined by the outcome of the game. I guess you will just have to find out.

Year: 2011 Length: 5 minutes Keywords: CumEatingInstruction Humiliation MasturbationInstruction J/OEncouragement JoeClips JoiClips Encouragement POV Jerkoff Guided Young GirlyDommes Blonde Helena HelenaStrong jo240

I Want To See You Cum Then Eat Your Cum

Very sexy masturbation instruction turns into forced cum eating lesson and humiliation with beautiful porn legend Teri Weigel.

Year: 2011 Length: 6 minutes Keywords: Cougar Milf Teri TeriWeigel Pornstar CumEatingInstruction Humiliation MasturbationInstruction J/OEncouragement JoeClips JoiClips Encouragement POV Jerkoff Guided jo239

The First Day Of the Rest Of Your Cuckold Life

Holly has been interviewing for a houseboy/slave for her and her boyfriend for months and has finally decided on you. She presents your with your new cage and lets your know exactly how she will controlling you and your cock, Before she locks you up.

Year: 2011 Length: 21 minutes Keywords: Chastity Smoking CockControl Feet FootWorship Holly HollyWebster Cuckold Humiliation MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Jerkoff Guided jo238

Big Sexy Round OILY Belly Masturbation Instruction

Helena tells you how to jack it for her belly and what she would like to do with your cock and her belly then gives you a countdown to cum all over that amazing belly.

Year: 2011 Length: 11 minutes Keywords: MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Jerkoff Guided Helena HelenaStrong Blonde jo237

He Was So Good I Brought You Home a Sample

You are Holly`s cuckold husband. She comes home from her amazing date and tells you all about it and brings you a surprise to use to eat while she tells you exactly how she wants you to jack off and gives you ever detail of her amazing sex.

Year: 2011 Length: 13 minutes Keywords: Cuckold Smoking CumEatingInstruction Humiliation CockControl FootWorship MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster Jerkoff Guided jo236

Cock Control Tease and Denial Humiliation

Holly teases you with her perfect body. When she finally lets you touch your cock she humiliates you. I think she lets you cum. Not sure though I shot this a while ago. I guess you guys will just have to find out if you are going to be allowed to cum.

Year: 2010 Length: 14 minutes Keywords: Humiliation CockControl FootWorship MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster Jerkoff Guided jo235

How Much Will Your Risk For Holly?

What do you think your wife or girlfriend would do if she caught you jacking off to Holly? Holly makes you open your door wide when you know there is a possibility that she could walk and and see what Holly wants you to do.

Year: 2011 Length: 13 minutes Keywords: MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster Jerkoff Guided jo234

Fuck The Stuffing Out of Your Pillow Bitch

Holly knows you are a nasty pillow humper boy. She talks to you and teases you about it then makes you do it for her while she teases you giving you instructions with it. She tells you when you can cum for her.

Year: 2010 Length: 17 minutes Keywords: MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster Jerkoff Guided Humiliation jo233

Very Sexy Camel Toe Panty Tease Masturbation Instruction

Holly looks amazing in this clip as she shows off her different panties and tight camel toe. She tells you to jerk off for her, tease you with up close shots of her tight camel toe. Great MI.

Year: 2010 Length: 13 minutes Keywords: MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster Jerkoff Guided CamelToe jo232

Your End of THE DEAL

Well the prom is over and you owe her and Holly has big plans. She wants you to jack off, fuck your own ass and shoot your load into your own mouth. She teaches you how and makes you swallow all your own cum.

Year: 2010 Length: 21 minutes Keywords: CumEatingInstruction Pantyhose-Stockings MasturbationInstruction JOEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster Humiliation Jerkoff Guided jo231

Tease and Denial 30 Second Game

Very sexy tease and denial build up leading to a 30 second MI, You may not even last the 30 seconds you are given after her tease but then again if you do you just might not get to cum.

Year: 2010 Length: 12 minutes Keywords: CockControl Pantyhose-Stockings MasturbationInstruction JOEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster Humiliation Jerkoff Guided jo230

Virgin SPH Mommie`s Panty Boy Masturbation Instruction

This is your VERY FIRST experience with a woman. Now that you are 30 and still a virgin your mother hired an escort for you. It is very clear to her that you are a momma`s panty boi so she has you masturbate just like she tells you to with her panties

Year: 2010 Length: 15 minutes Keywords: Jerkoff Guided PenisHumiliation SPH SmallCockHumiliation TinyDickHumiliation MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster Humiliation PantyFetish jo229

Holly Owns and Completely Controls Your Cock for A Month :Week 4

Remember Holly will own your cock for the month so by buying this clip you are agreeing to do exactly what she wants and not touch your cock between your weekly meetings with her.

Year: 2010 Length: 13 minutes Keywords: Humiliation CumEatingInstruction Jerkoff Guided MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster CockControl jo228

Come On Wanker Masturbate For Me

Holly teases you for being a chronic masturbator.and makes you jack off for her while she teases you with up skirt shots and her perfect body.

Year: 2010 Length: 6 minutes Keywords: Jerkoff Guided MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster jo227

Holly Owns and Completely Controls Your Cock for A Month :Week 3

Once a week (every weekend) for 4 weeks you have to buy the clip from this series to find out if you are allowed to cum and if you are allowed to cum what you will have to do with your cum. Every week is different!

Year: 2010 Length: 11 minutes Keywords: Humiliation CumEatingInstruction Jerkoff Guided MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster CockControl jo226

Holly Owns and Completely Controls Your Cock for A Month :Week 2

Remember Holly will own your cock for the month so by buying this clip you are agreeing to do exactly what she wants and not touch your cock between your weekly meetings with her.

Year: 2010 Length: 13 minutes Keywords: Jerkoff Guided MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster CockControl Humiliation jo225

How Far Will You Go To Keep Her

What you thought was your dream girl`s sweet quiet nice best friend/roommate is dressed up and extremely angry about being stood up for a date. She decides that she wants you to help make her `feel better` through using you for her pure amusement.

Year: 2010 Length: 15 minutes Keywords: Smoking Jerkoff Guided MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster CockControl Humiliation jo224

Holly Owns and Completely Controls Your Cock for A Month :Week 1

Year: 2010 Length: 12 minutes Keywords: Humiliation CumEatingInstruction Jerkoff Guided MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster CockControl jo223

HollyDommes Big Black Surprise

Sweet cheerleader masturbation instruction turned into male fantasy. Holly goes into graphic detail of how she is going to destroy you with her big black cock.

Year: 2010 Length: 13 minutes Keywords: StrapOn Humiliation Pantyhose-Stockings Jerkoff Guided MasturbationInstruction JOEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster jo222

Six Minutes MI

Holly controls your cock. You have 3 minutes to cum and 3 minutes of POT.

Year: 2010 Length: 8 minutes Keywords: CockControl Humiliation Jerkoff Guided MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster PostOrgasmTorture jo221

Toilet Boi Cuck and Pee Humiliation

Holly has a costume party she is getting ready for smoking and humiliating you telling you her plans for the night. You are stuck at home with her glass of pee and cigarette while thinking about your cum clean up duty later that night.

Year: 2010 Length: 10 minutes Keywords: CumEatingInstruction Pee Humiliation Jerkoff Guided MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly Smoking HollyWebster jo220

Jack off Torture Your Cock Then Ruin Your Orgasms For Us

Just what the title says. Holly and Widow instruct you on how to jack off, torture your cock and then ruin your orgasm.

Year: 2010 Length: 10 minutes Keywords: CBT Widow WidowCentauri Humiliation Jerkoff Guided MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster jo219

I Married Your Father so I OWN You Now: Do What I Say

You just turned 19 and your father married one of your classmates. She wants you to pay for all of the humiliation you put her through. She makes you strip while she laughs at your cock. Makes you fuck your own ass while you jack your little cock.

Year: 2010 Length: 19 minutes Keywords: Humiliation Jerkoff Guided MasturbationInstruction JOEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster CumEatingInstruction Pantyhose-Stockings SPH jo218

You Are A Loser With A Small Cock MI(4 Girl with CE Instruction)

All Humiliation SPH with a masturbation instruction and countdown to cum.

Year: 2010 Length: 8 minutes Keywords: Humiliation SPH CumEatingInstruction Honey HoneyWhite Penny PennyPoison Olivia OliviaRose Helena HelenaStrong Blonde Pornstar Milf Cougar Jerkoff Guided MasturbationInstruction JOEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV jo217

Holly`s Sexy Camel Toe Masturbation Instruction

Sexy Camel Toe focus masturbation instruction. Holly shows off her deep camel toe as she instructs you to jerk off for her and lets you know when you can cum.

Year: 2010 Length: 3 minutes Keywords: CamelToe Jerkoff Guided MasturbationInstruction J/OEncouragement JoeClips JoiClips Young Encouragement GirlyDommes POV Holly HollyWebster jo216

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