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Jerk Off Instruction No. 65 Box Cover
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Approximate Running Time: 00:49:21
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CWMH
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    Do you want to see a sexy ass? Ashlyn will show hers to you, but you have to jack your cock for her. She lifts up her skirt and you immediately see her juicy booty. You want to wear her ass like a hat. She spreads her cheeks apart and briefly inserts a finger into her tight asshole. She wants to feel you in her ass, she tells you. Is your cock hard? She knows that it is and she wants you to keep stroking it. Again she plays with her asshole, making it nice and wet. Her ass is in your face and you want to put your dick up inside of her. Your pace picks up and you are stroking your cock harder, too. With her ass in the air like that, you can also see her big pussy lips. With each ass wiggle, you are closer to your orgasm. Ashlyn informs you that she wants to rub your cum all over her ass, but you can first fuck her ass. You put it in and she moves against you with each thrust. You cum harder than you have ever cum before and she is thankful for you and your dick!

    Charlotte used to come to the pool at the house you now live in and she really misses being able to use it. Do you think that you could make an arrangement so that she could use the pool anytime she wants? She would be willing to spend a little quality time with you if you will agree to let her use the pool anytime she wants. She cannot touch you, but she is definitely able to let you look at her tight body as you play with your dick. Charlotte will even coach you through a jerk off session with her anytime you like. Grab your cock and let her tell you exactly what to do. She explains just what she wants you to do to your cock. Did you know that she is only 18 years old? Her titties look it – they are perky and firm. As she slides off her panties, she can see how turned on you are. Tell her how badly you want to cum. Go on. Tell her. She already knows, but she will let you cum only when she decides it is time. Keep jacking your dick off. Imagine that her little hands are working your fat shaft. She knows that you are almost ready to blow, but you must hold off just a little longer. Spit on your shaft and keep it wet. Are you ready to cum right now? Do it! Cum right on pretty Charlotte. Oh, you naughty boy. Look at the mess you just made! She will go clean up in your pool.

    Miss Lyra knows that you are a panty-wearing sissy and she demands that you put on pink panties. Then she throws a tube of lipstick at you and she commands you to put it all over your pouty lips. Next she tells you that you are to take your sissy cock out and stroke it for her. Did you know that she has arranged for an entire football team to come over and make you their little cum slut? As you think about all those black cocks violating you every which way, you begin to stroke your dick. This would not turn on a normal man, but you find that your dick has never been harder than it is right now. The threat of Miss Lyra pimping you out at a truck stop further encourages you. This is what sissies do, after all. When Miss Lyra pulls her panties to the side, you see her perfect pussy. You know, however, that you would never be able to get near it. The best you can do is to be a perfectly subservient sissy cocksucker for your Mistress. That is your role and you are happy to do just that. Today there is a very special treat for you. You will eat your own cum. You want to please Miss Lyra, right? Not only will you eat your cum today, but every time that you cum from now on, you will consume your own jizz. Get used to it, sissy. Miss Lyra counts you down and you cum into your hand. You somewhat reluctantly eat your jizz from your own hand and then you thank Miss Lyra for all she does for you!

    You already have a girl, but you are back again to see Karla. Is your girl not giving you what you need? Is it only Karla that can satisfy your needs? You know you should not be here, but since you are, Karla wants to help you. She sees your pants bulging, so she tells you to get out your dick. Karla is pleased to see the effect that she has on you, though she feels a little pity for your sad sex life. Her body is so much more firm than your girl's body. Karla is so petite and so sweet. She is eager to help you through your time together today. She teases you with each peek at her pink pussy, all the while reminding you that you can never touch Karla. Do you wish she was next to you right now? You will have to cum without her touch, but you have her sexy voice begging you for your hot load. That is enough for now as you jerk your dick faster and faster until you finally spew forth your man gravy for sexy Karla.

    Natalia wants to play a game with you. She is your hot, older step sister and she wants to get to know you a little better. Just take your dick out for her. Can you get it hard for her? Stroke it. Okay, so it is time for Natalia to show you her titties and she reveals an all-natural set of tits. She even asks if you want to touch them as she bounces them for you. You love your older step sister so much right now! Natalia asks you to take off your pants and shirt and she likes what she sees. She reciprocates and slides down her skirt. Her long, lean body appeals to you quite a lot, but when she takes off her panties, you like what you see even more. Her well groomed bush proves to you that she is not a natural blond, but you can let that slide. After all, she is naked and paying attention only to you right now. As she caresses her ass, she informs you that she would be more than happy to teach you lots of games. You would be more than happy to learn anything Natalia wanted to teach you. She teasingly asks where you want to cum and you decide that you want to blow your load on her face. Natalia encourages you to continue stroking until you cum all over her pretty face. "Feed me your cum," she whispers. That does the trick and you fill her hungry mouth with your sweet sperm.

    Your cousin Rilynn is bored and she is looking to you for some entertainment. What can you do to amuse her today? She wants to play a game with you and you go along with it. It is called "Never have I ever" and you never played it before. It goes quickly and Rilynn wins. She decides that her prize should be that the two of you mess around. You are not truly related biologically, so just shut up and go along with her request. You never turn down the opportunity to show off your dick, so you show her what you are packing in your pants. She asks you to start jerking yourself off because she wants to see what moves you have. Your dick grows with each stroke and even more when Rilynn begins to take off her clothes! Soon she is telling you how to work your own cock and you listen to her every word. Her body is too hot not to listen to her, especially when she finally tells you to cum for her.

    • Scene 1 - 7 mins 48 secs


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    • Scene 2 - 8 mins 30 secs


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    • Scene 3 - 7 mins 5 secs


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    • Scene 4 - 8 mins 14 secs


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    • Scene 5 - 8 mins 35 secs


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    • Scene 6 - 9 mins 3 secs


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    Cast & Stars: Jerk Off Instruction No. 65


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