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Introduction:

First Story in A Series (Open for input)
This takes place in an average small Midwest town Jack and his wife, Sharon live just out of town. They also have a baby girl, Ashley who is six months old. They reside in a three bedroom ranch style house which has an average size basement that is more of a man cave for Jack and in the backyard is fenced in with an in ground pool. Jack is the principal of the local school and Sharon is a registered nurse that works at a hospital in a neighboring larger city. Since the birth of Ashley,Sharon was ableto arrange it so that she just stays at hospital and works from Friday afternoon when Jack gets home till Sunday evening. After lengthy discussions they agree to seek out a babysitter for Ashley someone that could be able to stay and help out when Sharon was not at home. Fortunately there are several girls that have flyers posted up around town. After reviewing the choices they decide on this girl named Anna. Who happens to come highly recommended by some of the parents she has babysat for and is said to be very good with children. Anna just recently turned fourteen, she’s about 5’3”, her hair is brown with light natural reddish highlights its shoulder length but she usually keeps it in a ponytail and her eyes are green hazel. Anna is definitely well developed for being a freshman her measurements are 32B-26-32 and very toned because she plays on the varsity girls’ volleyball team and is a cheerleader for varsity football and baseball teams. Jack does know quite a bit about Anna seeing how she does attends the high school which he is the principal and assistant coach for both sports that she cheerleads for. Anna comes to stay after school on Friday when she gets done with cheerleading or volleyball practice and if there is a game that night she just rides back with Jack and then takes her home on Sunday. For when there is a game the school provides daycare till the parents get back from it.

There is plenty of room for her to be able to stay at their house. After a few weekends Anna slowly more of less turns the guest room into hers, bringing some of her clothes and stuff so she doesn’t have to bring it all the time. Everything seems to be going along fine until Jack notices himself starting to have thoughts of Anna in a sexual nature. He is able to suppress these desires much as possible and just takes care of them in private. After a particular weekend when Jack returned home from taking Anna home, Sharon questioned him if he’d been looking at porn. He told her, “no of course not” well someone did it’s in the history on the computer, she stated. Breathing a sigh of relief cause he thought she’d found his porn collection. Once Sharon went to bed Jack decides to check a few things out for himself, he discovers that someone had been looking threw his porn collection. He also checks into the accusation over the computer and discovers that it was done Saturday morning while he was gone golfing. Well once discovering this and over the course of the next week Jack places a few hidden cameras in areas of what he thinks will produce the most interesting footage. The next weekend comes and goes then when he has time during the following week decides to see what exactly the cameras caught. Just as suspected the one he placed in the computer room catches Anna viewing some porn sites after she gets the child down for a nap. Then from the one he placed to over watch his porn collection that’s down in his man cave he watches as Anna looks threw a couple magazines and then takes a DVD and leaves the area. Given these events he figures that the footage from the third camera will be the most intriguing cause it’s the camera that he placed in her bedroom. Intently he watches as she comes into view. Placing the DVD in the player she sits on the foot of the bed and begins to watch the movie. In a matter of moments she stands and begins to remove her shorts revealing her panties which are the boy-short style. She then gets back on bed but moves slightly higher up on it and arranges the pillows so she can see the television.

A few moments go by when Anna sits up and peels off her t-shirt exposing her ample breast. Jack is amazed at how perky they are not to mention the fact she’s not wearing a bra. She then resumes her reclined position in short order after this one of her hands begins to caress her breast while with the other she starts to massage her inner thighs. Jack watches intently as Anna begins to rub her young pussy threw her panties. While her other hand begins to squeeze her breast and pinch her nipple. Slowly Jack watches as the one hand moves up and then disappears inside of her panties. He knows that he should turn this off if nothing else for the simple fact that she is one of his students. But the growing bulge in his shorts tells him otherwise. He watches and imagines Anna’s finger between her wet pussy lips searching out her clit. Watching closely you can see her hand moving just a little this from her rubbing her clit in a circular motion. Momentarily Anna stops and removes her hand and peels of her panties. Then he watches as she rolls to her side and retrieves something out of the bottom drawer of her nightstand. Then she gets back in her previous position but now she places her feet flat on the bed just beyond shoulder width apart and knees bent slowly resumes rubbing her clit. Jack watches as Anna’s agile fingers manipulate her clit in a mesmerized state he slips a hand in his shorts and begins to stroke his cock. There is already a generous amount of pre-cum flowing out of the tip. He undoes and removes his shorts and boxers releasing his throbbing cock as he watches Anna slip a finger into what he imagines has to be a tight pussy. He strokes his rigid cock while watching Anna fingering herself. Thoughts of how tight that young pussy must be fill his mind as he grips his throbbing cock tighter while stroking it. Suddenly he watches as her teen body shivers from an orgasm. She then pulls her nectar covered fingers out and licks them clean. With anticipation Jack watches still stroking his cock as Anna picks up the unknown object up off the bed and nears it towards her pussy as it comes into view he realizes it’s a vibrator. He watches in amazement as this succulent little minx pushes the vibrator gingerly into herself. With slow but yet deliberate motion she slides it in and out gradually quickening the pace. Anna continues this until yet again Jack watches as her body trembles from an intense orgasm. This results in him continuing to jack off until he shoots his thick load of hot cum in the air. Jack can only imagine what it would feel like to plant his seed deep in that pussy feeling it milking his thick cock.

After a few more weekends of the above mentioned events goes by Jack decides to do something to raise the stakes sort of speak. The night he puts his plan in to motion is rather normal. Other than he asks, “Anna, would you like to join me in the living room to watch a movie after you get the youngster to bed?” With no hesitation Anna agrees to the invite and meets Jack on couch to watch the movie. Jack is sitting on one end of the couch wearing a pair of gym shorts and a muscle shirt. When Anna enters he can’t help but to notice that all she has on is a neon pink nightshirt that stops mid-thigh it accents her tan body very well. She sits on the opposite end of the couch.During the movie there are a several sex scenes Jack notices that when those scenes are on Anna watches with great intent. Also he observes that her nightshirt has risen up some exposing her firm ass cheek closest to him also giving him a brief view of her panties. At the conclusion of the movie he says, “Well some of that looked interesting huh?” This comment catches Anna off guard she looks at him in a slight state of confusion. Then she answers, “Yea I bet some of that could be amazing.” She slowly moves closer to him this is when Jack asks her bout the use of the computer. At first she denies doing it but then he tells her that he knows she does it while he is gone. By now Anna is sitting right next to Jack her hand ends up on his thigh. This momentarily brings Jack back to reality; He tells her, “We shouldn’t be doing this.” She asks, “Why not; I promise not to tell anyone ever!!!” as Anna says this; her hand begins to massage the predominant bulge in Jack’s shorts. With a gleam in her eye she says, “Plus why do you think I took this job.”

Jack can’t believe what has begun a voice in his head speaks up,” You can’t let this occur she is too young and not to mention one of your students.” But his throbbing cock that is being lightly squeezed by her petite hand is saying, “Let it happen you know it’s what you want plus she’s willing to allow it.” As he gazes deep into Anna’s green eyes it’s like he becomes hypnotized as she pulls the waist band of his shorts over the tip of his rigid cock. She gasps lightly saying, “Wow, you are definitely bigger than I imagined it.” Slightly in shock Jack mumbles, “Bigger than you imagine?” As Anna lightly grasp his firm shaft and begins to stroke she answers,” Yes, I said bigger, I’ve been masturbating and using a vibrator on my tight pussy since I took this job and always imagine it being you in me.” Anna’s grasp gets tighter as her soft hand moves up and down Jacks thick shaft. She also states, “By the way Jack I’m not exactly a virgin... I broke my hymen one night but I’ve never had the real thing,” this is said with a smirk on her face. This is when Anna stops stroking Jacks throbbing thick cock. Mesmerized by the young sultry vixen before him all Jack can do is watch as she slips off the couch taking up a kneeling position just in front of him. Then she slowly puts her hands across her body and grabs the bottom of her nightshirt and begins to raise it slowly. He watches as she reveals her firm tan thighs then her rainbow pattern panties come into view, slowly like a curtain being raised it goes up an inch at a time revealing her tone flat stomach, gradually it moves higher exposing her perky breast Anna’s areolas are the size of half-dollars and her nipples are sticking out slightly but no larger than a pencil eraser. Anna then reaches out and pulls Jacks shorts the rest of the way off. With his legs spread just beyond shoulder width she takes up a kneeling position between them. She then resumes stroking his thick shaft up and down within seconds there is pre-cum seeping out the tip seeing this she takes the tip of his cock in her mouth sucking on it like a sucker. Anna then takes her tongue and circles the tip and flicks it occasionally. A mixture of her saliva and his pre-cum fills her warm mouth she swallows a little of the salty but sweet mix.

Once Anna’s gets her first taste of cum she instinctively begins to moan a little as her mouth moves up and down Jack’s rigid cock she can feel the tip of it throbbing in her mouth while doing this her hand rhythmically strokes his thick shaft. Jack feels a stirring inside of him while Anna works her mouth up and down she then takes her hand and begins to caress and fondle his scrotum. In no time at all Jack moans out, “I’m going to cum.” Hearing this she quickens the movement of her mouth and forms a tight seal as she can with her lips. Jack groans as he begins to climax shot after shot fills Anna’s mouth doing her best not to let a drop escape her lips as she gulps down his thick warm nectar. When his orgasm subsides Anna continues to lick up every drop that escaped her lips. Upon completing her task Anna looks up grinning and asks, “So how was that?” In a state of nirvana and after catching his breath Jack looks at her smiling and says, “Absolutely magnificent just where did you ever gain knowledge of that skill?” Still grinning she says, “I kind of have something to confess.” With a stern look he says, “Go ahead I’m listening!” With a smirk she says, “I found and look threw some of your magazines and watched a couple of the DVD’s and I practice the technique on bananas and suckers.”

While saying this she climbs up and straddles his lap. Jacks still hard cock is now between Anna’s legs just within an inch from her young tight pussy, he can feel the heat radiating on the tip of his cock only separated by her panties. Anna slowly wraps her arms around his neck and leans closer into him and gently presses her soft tender lips to his and begins to kiss. As they do Jack then places each of his semi rugged hands onto Anna’s firm ass and squeezes lightly. This results in a slight gasp from her at that moment he nonchalantly takes his tongue and licks her lips and then little by little penetrates her lips with his tongue. Their tongues meet and begin to intermingle as each explores the others mouth. Jack continues to squeeze and embrace her firm sultry ass. While doing this he pulls her closer to him instantaneously she gets wide eyed because his hard cock is pressed to her unexplored pussy now he not only feels how hot this nymphet is but there is also a liberal amount of moisture. Their kiss intensifies with passion as it does he keeps one hand on her ass and moves other to begin to caressing and fondling her perky breast simultaneously.

This drives Anna practically crazy with pleasure she begins to grind her hot wet panties against Jacks once again throbbing cock. This continues for a few moments till Jack places both hands back on Anna’s bottom and stands holding her, her arms still around his neck and automatically she wraps her legs around his waist. He slowly begins to walk carrying her when she breaks the kiss and ask shyly, “Where are you taking me?” With a gleam of lust in each of their eyes they stare at each other as he makes his way down the hallway and into her room which tonight is lit by moon light. She grins at him and says, “Hmmm, we’re going to have sex on my bed; might as well that is where I fantasize about it the most.” As soon as they reach the bed Anna scoots up on it and assumes a position lying on her back and spreads her legs apart. Jack takes up a position on all fours near the foot of the bed and begins to move slowly like a lion stalking prey. While doing this his eyes survey the magnificent treasure that is laying before him when he gets about half way up her legs is when he pauses his approach as he finds himself in a awestruck state for in his eyes has come to rest on the crotch of her wet panties. He then places a hand on each side of her grasping the waistband of her panties and begins to peel them down she raises her hips and bottom off the bed allowing them to come off with no resistance. As he removes Anna’s panties a slight sigh escapes her lips.Now lying before Jack is a vision of bliss; Anna’s pussy is completely shaven and her lips are slightly swollen it’s a better view than he ever could have imagined. Leisurely he descents his head and lightly begins to kiss her inner thighs Anna’s skin is so soft on his lips he alternates kissing from one leg to the other gradually working his way towards her exquisite treasure. As he draws nearer the intoxicating scent of her nectar coming from young moist pussy fills his nostrils. Both of them shiver slightly; Jack does just from the fact of the feel of her soft skin. Anna on the other hand is due to she can feel his warm breath on her sensitive moist pussy lips. Slowly Jack sticks out his tongue and begins to lick Anna’s pussy lips doing so makes her moan slightly. He then licks up and down each side of her unexplored slit this really makes her juices begin to flow. Delicately he allows his tongue to pierce her slit licking it up and down gradually plunging it deeper probing and seeking out her budding clit.

Upon finding it Jack takes his fingers and spreads her lips granting himself total access to it. Then he begins making small circles on her clit followed by flicking it with the tip of his tongue. This action emits wave of pleasure throughout Anna’s limber body making her shiver a little because of that she lunges her hips upwards pushing her clit more into Jacks mouth. He nibbles lightly on her clit this makes her moan loudly followed by saying, “Eat my young wet pussy, and make me cum Jack please!” He happily carries out her request continuing to nibble and suck on her excited clit after a few moments. Delicately he begins to slip a finger into her wet tight hole. Her intoxicating musky pussy juice flowing freely and providing the perfect amount of lubrication as he slips his finger in deeper. She begins to breathe heavily and moan a little louder; his finger feels to her as if she has two of her dainty fingers in her tight pussy. Like a ship in uncharted waters trying to find an island Jack uses his finger to search out Anna’s g-spot. Knowing the approximate area the searching doesn’t take long he begins to rub in a circular motion applying light pressure while still nibbling her clit. The result of this is Anna gasping and saying, “Oh my god, what you are doing feels so unbelievable Jack.” Jack continues with fingering Anna’s ever wetting pussy quickly he pauses from giving her clit attention and says, “This is only the beginning of what I want to make you feel.”

Jack quickly resumes the attention on Anna’s clit. She unconsciously begins to grind her pussy on his finger with a devilish grin on his face he slips a second finger into her. Now with two fingers working on her g-spot in a come here motion. In nearly no time flat Jack knows what is about to occur he can feel Anna’s tight virgin like pussy contracting on his fingers. He ceases the attention on her clit as he fingers her faster plus he wants to watch her face and body react to the oncoming culmination of sexual pleasure that has been building. With an, “Oh GOD I’m cumming!!!” detected in Anna’s moan. Jack unexpectedly takes his fingers out of Anna’s tight pussy. Just as her petite body begins to quake cause from deep inside an orgasm has begun. Practically having no control over her teen body surprisingly to her like a volcano she erupts like hot magma her juices flow out her young tight pussy flowing out on to the bed. In a state of delight and catching her breath she manages to say, “God Jack I’ve never had an orgasm like that that was really unbelievable.” Anna lies there in a somewhat immobile state while Jack still kneeling between her legs admires her cum coated pussy he then leans back down and begins to lick up some of her sweet nectar. All she can manage to do is shiver from his tongue tickling her extremely sensitive pussy. She can’t help but to moan, “That feels so good Jack” couple more moments of this go by. Jack not missing a drop of Anna mouth-watering pussy juices she moans, “Jack I want a taste please.” Gladly he crawls on top of her Anna licks around his lips and then presses her lips to his. During the kiss Anna can feel the tip of Jack’s hard cock touching her wet pussy lips. Breaking the kiss Anna looks deep into his eyes and states, “Jack, I want to feel your thick hard cock in me stretching my tight pussy.”

In a position like he was going to do a push up the next thing he feels is Anna’s petite hand grasp his rigid cock. Jack as in a hypnotic state gazes deep into her young beautiful eyes. She raises her back off the bed and kind of props herself up on one elbow so she can watch as she guides the tip of Jack’s cock up and down her wet slit. They both glance down as she slides just the tip between her soft velvet lips then they gaze into each other’s eyes. Anna moves the tip of Jack’s cock to her clit and begins to grind her hips. Jack reaches down taking control of his cock as he does Anna lies back on bed. He rubs tip of his cock against her clit and then down teasing the entrance of her wet tight pussy. She lifts her hips resulting in his tip beginning to breach her virgin like canal she moans and says, “Please fuck me Jack I want to feel you deep in me now!!!” Anna then lowers her butt back on the bed spreads her legs as wide as possible bending them at the knee and her feet flat on the bed. Jack carries out her request and slowly pushes the tip of his cock into her tight pussy. She sighs slightly her pussy begins to stretch accommodating his manhood. His pre-cum and her juices that are flowing makes for sufficient lubrication as he gradually inserts inch by inch of his thick hard cock. “Oh my God, Jack you are so much bigger than my vibrator.” Anna cries out as Jack begins to move his seven inch long and roughly two inch in thickness cock in and out. Even though her young pussy is conforming to his thickness he has to focus on not climaxing prematurely because she’s tighter than he ever imagined.

Sliding in and out becomes easier due to the mixing of their fluids Jack begins to quicken his pace. As he thrusts in and out Anna’s moans grow louder she instinctively mimics his movement so they begin to move in unison. All of a sudden as Anna lets out a moan that is deep from her core. Without delay like a python she wraps her limber tone legs around Jack’s waist as her tight pussy pulsates on his thick shaft from yet another orgasm. Giving her no time at all to recover Jack abruptly pulls out of her and in a commanding voice tells her, “Get on all fours now I want to fuck you from behind till I cum deep in you.” With the utmost respect Anna complies graciously with the demand. Jack grasps Anna at the waist as he thrust his hard cock back deep into her tight pussy. Pumping in and out like a piston in an engine he feels his balls begin to tighten. She turns her head looking at him and grins mischievously and says, “Cum in my tight pussy fill me up!!!” Jack leaves one hand on her waist pulling her close as possible to him his balls smacking off her firm thighs. Anna’s body begins to fill with immense pleasure yet again she grips the sheets securely in her hands. With a deep thrust Jack holds his cock deep in her as he places his muscular chest to her back while placing his free hand on her breast. When he rises back up he takes her delicate body with him while fondling her breast and making precise strokes with his cock he then kisses her neck and whispers in her ear,” I want you to rub your clit and cum with me.” Obediently she immediately fingers her swollen clit vigorously also Anna grinds her pussy on his thick pulsating cock she can feel every throb in her aching pussy muscles. While Jack is kissing and nibbling her tender neck along with fondling her breast and pinching her nipple lightly he can feel her tight pussy milking his ready to explode cock. This leads up to the culmination as both let out moans waves of Anna’s juices coat Jacks cock while volleys of his thick warm seed fill her pussy.

They both collapse on the bed limp and exhausted from the nights activities. After a few moments Anna pulls herself off Jacks now softening cock. In a state of unbelievable bliss he watches as she takes up a position like she’s going to give him another blow job. Exhausted he says, “Anna I don’t think I have it in me to go another time.” She grins and responds, “I just want to suck your cock clean and see what we taste like together.” Given that he watches as she licks every inch and savors every drop. When she is done Anna places her head on Jacks chest and asks, “Was this just a one-time thing or what?” Jack responds, “As phenomenal as this was I’m definitely prepared to make this more than a one-time thing.” With a devilish grin Anna says, “Good I was hoping you’d say that I’d hate for Sharon to find out.”
14 comments

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