Story Details

The Babysitter Next Door

Loverboy69 on Cheating Stories

Dan and Dana rushed out the door to their dinner - late as usual. Dana was never satisfied with her appearance and she'd change outfits three or four times before finally settling on a particular one, then she needed to compare shoes and handbags to find what she considered the perfect match. Dan was always frustrated by his gorgeous wife's indecision. The usual babysitter, Molly Kelly, the next door neighbor was already playing with the kids and assured Dan and Dana everything would be just fine.



Dan cast a backward glance at Molly as he escorted Dana out the door toward the car. Molly was standing there looking so sexy. She wore tight shorts, a tank top and flip flops. She was scrubbed clean and innocent appearing, except for the smile on her face. Dan had become disconcerted by his recent and seemingly constant sexual fantasies about Molly. She was 16. Dan and Dana lived next door to Molly and her parents for the last 7 years, so Dan had known her since she was nine years old. He was embarrassed at his thoughts but he tried to dismiss his thoughts as not being his fault.



I mean after all, he thought to himself, Molly had taken to dressing in the sexiest clothes - tight shorts, small tops, showing her tanned and girlish figure, but it was her expressions that really put Dan in a bad way. In his mind she was the devil. Dan noticed in the last year or so Molly had taken to casting sexy little glances at him. She would do or say something slightly provocative - always in his presence alone - and then she would flash this knowing gin at him. Her eyes seemed to burn through him as she did these little things.



Once Dan was cutting the grass and saw Molly emerge from her back door wearing a pair of super tight blue shorts that looked painted on her bodacious ass. She walked around her deck and every time Dan looked up it seemed two things were happening - Molly had her back to him and she was bent over or some such seeming pose and she was looking at him whenever he looked up and noticed her. It began to plant itself in his mind that she was trying to entice him. Was it just her coming of age innocence, he asked himself? If so it certainly was strategically timed, for whenever he looked at her she was looking at him and her expression was alluring, and purposely so. Dan thought it impossible for it to be a coincidence - it was just constant and that indicated intention to Dan. He decided to test his theory.



The following weekend Dana took the kids the 100 miles or so to her folks house for a weekend with the grandparents and Dan figured it was now or never. He began that Saturday morning hanging out on the deck having his coffee and reading the paper. By 11:30 Molly hadn't appeared and Dan figured it was a lost cause. He gathered up his mess and deposited the cup in the sink, the paper in the recycling bin and started to putter around the house doing nothing really. He was frustrated and decided maybe a call to an escort service and some hot hooker pussy would get his mind off his 16 year old neighbor, but it was not to be. As Dan passed the dining room bay window sure enough Molly emerged onto her deck.



Dan stood back from the window and observed her. She walked back and forth on the deck seeming to do nothing except sort of pace. He decided to take his shot. He strode through the kitchen and back out onto his deck. Molly saw him and smiled, "Hi Mr. Anderson!" Her voice was warm and sweet - completely innocent, almost - and she stood looking at him as if she had more to say. "Morning Molly," he replied now nervous and confused. What next he thought to himself. "Whatcha doin'? she asked, a definite curious tone in her voice, though not one of actual curiosity about the reply but more of a fishing expedition he thought.



"Ahhhh...nothing really," Dan replied tripping over his words. Molly began to probe, "Where is Mrs. Anderson and the kids? I saw them taking suitcases out Away for the weekend?" she inquired. "Yeah, Dana took the kids to her mom's for the night. They'll be back tomorrow evening. Ya know, visiting the grandparents and all that," he informed her. "Wow, so she left a sexy man like you on his own?" she asked. Dan looked at her embarrassed but Molly didn't seem to be at all so by her comment. In fact quite the opposite. Before he could come up with a reply to the unexpected comment she added, "I would never leave a stud like you home alone!" Dan felt embarrassed all the more by her boldness and his secret thoughts. "Well, " he answered, "I don't know about all that . . ." he trailed off unsure of where to go with this conversation.



"So, what are you up to on this pretty June morning?" he asked changing the subject out of sheer terror for his feelings and her seeming delight at putting him on the spot. "Nuthin" she answered. "My folks have left for the day. Dad took Mom and my little brothers to Busch Gardens for the day...I didn't want to go stand in those long lines with my two little dweeb brothers so I am grounded and have to stay home all day by myself," she whimpered, putting on her best pouty faced looked. Dan felt the stirring in his groin and grew panicked.



"Hey, since we're both left on our own today, how about if I cook some hamburgers on the grill for you and me?" she offered." Dan gulped in confusion and fear for that thought. "Ahhhh...maybe, but isn't the man supposed to do the grilling?" he asked, wishing he'd never said it. He realized his words implied the sexual delineation and relationship of them being opposites. "Okay" she cheerily replied, "You can be the man and I'll be the woman." Her words struck fear in him but it was her expression that really sank him into mortal terror.



She was staring at him when she said it as if she was a hungry predator and he the prey. Her eyes were squinted and she seemed to look through him. And his cock was growing a bit too interested in all he saw and heard. "I'll let ya know about the burger Molly," he said wishing he could fuck her and run from her all at once. She put on her most sexy little girl face and pouted again, "Gonna leave me hanging, Mr. Anderson?" she asked. "Of course not Molly. If you're hungry and I am eating I will not let ya starve. That would be not be neighborly." She seemed to perk back up at that. "Well, I'm going to go do some stuff in the house now ... I'll probably see ya later then," he said as he wished he hadn't.



He wanted to leap the fence and grab her supple and lithesome little figure and show her how men treat women they desire. And he desired her very much. She just stood looking at him as if she had more to say but not knowing how to say it. He smiled and walked back through the kitchen door. Molly then sat in a lounge chair as she appeared to be sunning herself.



Dan went back to the dining room window and stood back a few feet in the shadows of the unlit house, knowing as bright as it was outside and with no lights on in his house, he would be unobserved. He loosened his shorts and let his cock free. He began to rub it looking at her lying on the lounge chair. She lay on her back. Then she unbuttoned her shorts. He thought she might remove them but no, she just unbuttoned and unzipped them and left them on her. Odd, he thought.



The she flipped over onto her tummy and her shorts slid down until the waistband was just below the curve of her very fine and large ass. He could see the top of her ass crack as the material barely covered her ample butt cheeks.She propped herself up on her elbows and seemed to be reading or something. Then she bent her legs at the knees and crossed her ankles behind her. She pumped her feet back and forth, her thigh muscles and calves flexing. But he was really taken with the bottoms of her feet. They were almost black with walking on the hardwood floors of her home in bare feet.



Dan was in Heaven now. He'd always had a thing about nude models - well really any barefoot woman, but especially the antique and vintage porn when these beautiful women would pose in studios or outdoors. When he could see the bottoms of their feet they were always dirty what with walking around barefoot too. Molly's dirty souls of her feet brought back memories of jerking off as a kid looking at the porn his dad had hidden in the attic.

The models were barefoot and their souls were covered in blackness from the floors.



It always drove Dan to distraction to think about these women walking around naked in front of men as they posed nude. It wasn't so much the posing that excited him but the fact that when not posing for a picture at that moment these naked women would unabashedly walk around naked in front of these clothed men. It sort of really turned him on - not so much the women's nudity, but their care free attitudes about the situations that got him off.



Dan was taken back to the present time as he watched Molly sort of fumbling around underneath herself. Something struck him as odd, but he could not really see it to well. He remained in the shadows and made his way to the kitchen to look out the window that faced Molly's deck. The sight froze him in his tracks. Molly had both hands under her body - one was fondling her little tits under her shirt and the other was in the open zipper of her painted on jeans shorts. She was fingering herself or at the very least rubbing her clit. She was masturbating on her deck. Dan stared as his cock grew to its full 71/2 inches and he pulled on it for all he was worth.



Molly laid her head down on the lounge chair, her face facing in his direction. Her eyes seemed closed as she rubbed her womanly parts to pleasure herself. Her rubbing became a bit more furious as Dan surmised she was getting off. Molly lifted her head and made a contorted expression with her face. Her mouth hung open as her ass wiggled furiously as she fingered or rubbed herself, one hand still under her tank top rubbing her small young tits.



Dan rubbed his cock with abandon and could feel the pent up desire for this little creature begin to build. He leaned back against the wall on his left side and stroked his cock for all it was worth. He closed his eyes and began to fondle his balls with his left hand as his right worked his cock as only he could. The cum rushed form somewhere inside his belly and the pleasure nearly caused his knees to buckle as he shot cum about 6 feet from his cock. He deposited five or six major spurts of cum all over the kitchen floor. He could see cum all over the front of the cabinet below the sink. He continued to stoke himself more slowly and deliberately in the after feelings of exceptional pleasure.



He let his held breath escape and looked back toward Molly. Molly was on her knees in the lounge chair, her shorts still unbuttoned and unzipped as her ass and hips held the tightly stretched denim from sliding past her womanly hips. The she looked directly into the window, seemingly as if looking right at Dan. She then took her right hand - the one that was shoved in her shorts and licked each fingertip clean. She then smiled a great big satisfied grin and waved at him. Dan froze. She then blew him a kiss and with her shorts open and clinging for their life to her hips and ass, she shook her fat ass and walked back into her kitchen with a deliberate effort to make it all shake and entice him no end. It did. He stood mortified.



Could she see him, he wondered? Fear flashed over him as the waves of pleasure finally dissipated. He was shaking in excitement and fear. Did she really see him? Did she do all this for him to see? What other conclusions could he reasonably assume given the events? He put his friend back in his pants. zipped up and proceeded to clean up the mess. He had to use about ten paper towels to clean up all the cum - it was everywhere. It was the most explosive orgasm he'd felt in quite awhile. He finished cleaning up and took the trash from the kitchen can and out to the garbage cans on the side of his house.



He'd sort of forgotten in his panic that Molly might see him - she did. As he opened the lid to the plastic can she appeared in her own dining room window opposite his side driveway. He thought he'd seen a flash of light or shadow or something in the window and his curiosity defeated his decorum and he looked at the window. Molly stood in the window smiling at him, her jeans still unfastened and unbuttoned, still held tightly as they were stretched over her magnificent ass. She seemed to suffer no such embarrassment or mortification as he did. Her expression was again that of a hungry animal eying its next meal.



He slammed the garbage in the can and headed back up on the deck and into the house. His desire got the best of him and he looked back at Molly's window and she stood there still smiling as she waved again, this time with one of her fingertips in her mouth ever so slightly. He rushed in the door and slammed it behind himself, fearing this little girl. He swore he needed to get his shit together and stop obsessing about the 16 year old babysitter next door.



Dan went upstairs and showered - again. He dried and collapsed onto his bed naked. He enjoyed the cool air from the AC vent blowing on him. He turned on the TV and caught the beginning of a baseball game coming on. He tried to watch it and distract himself. Soon he drifted off into fitful sleep.



Despite the coolness of the air coming from the AC vent Dan startled awake in a sweat. The shadows of the light filtering in his bedroom windows told him he'd been asleep for some time. He looked at the clock. 3:45PM. Wow, he thought. He'd snoozed for about two and a half hours he realized. He rubbed his eyes and almost leaped up onto the ceiling as he hears "God, I thought you'd never wake up." Molly stood in his doorway. Dan's cock was half hard and Molly stared at him and it. He started to try and cover up but Molly strode across to him and placed her sexy little finger on his lips as Dan looked at her in terror.



"Shhhh..." she admonished. Dan lay there naked, excited, terrified and curious as Hell. Molly reached down and hefted his fattening cock. She dropped it and it plopped against his thigh. She stared into his eyes as she peeled out of her clothes - different ones than she'd worn earlier. And now her medium length auburn hair was in pigtails jutting out high on the sides of her lovely head.



"I know you want me Mr. Anderson, and that's cool because I want it worse than you do," she purred at him as she traced her fingertip around his belly button. She looked at him and the look in her alluring eyes froze him silent and helpless. She pulled at her top and her small, pert tits were beautiful. As he stared at them she slipped her fingers in her waistband of what looked to be Spandex bicycle shorts. They clung to her like a second skin. "Like my ass, don'tcha Danny Boy" she growled. He stared his mouth agape and dry. She turned around, looked back over her shoulder and said "Enjoy the show," as she slid the bike shorts past her generous hips and over the curvature of her astounding and womanly ass.



She then leaned her ass back against him and purred "Wow that feels so hot Mr. Anderson!" She slid her ass back and forth against his chest, waist and hips. He unconsciously took his left hand and ran it over her ass cheeks. "Yeah, that feels good," she seethed at him in a hushed and horse whisper. "It tastes even better than it looks too," she said as she climbed on the bed, onto his chest, her ass in his face. "Taste it Dan." She pushed back until her cunt and her plentiful but taught ass cheeks smothered his face. Her cunt smelled of flowers. Her took both hands and grabbed her ass as he pulled her down onto his face, his mouth sucking on her labia.



Her ate her like she'd never known. She purred her delight throughout his muff munching. "Lick my asshole, Mr. Anderson" she encouraged. He did. Her asshole was cute and puckered. He tongued around it and she pulled her ass cheeks apart and he buried his tongue in her ass. She ground herself against him. He licked her asshole and back to her tight little pussy until she came. She then leaned onto his belly and took his growing cock into her warm mouth. She sucked and pulled on the shaft as he grew to full hardness. He lay staring at the ceiling as she then licked all the way up and down his cock from head to base over and over. "What a fucking awesome cock Danny Boy," she announced sounding more like a hooker than a sweet 16 year old girl.



She dropped his fattie and lifted off of him. "Fuck me with that Goddamned thing!" she adamantly demanded. She slid her ass down over his cock. She put her hands on his chest and held herself there as she slid back and forth over his cock, covering it with her juices. The look in her eyes was euphoric to Dan. She took her right hand and hefted his cock to her cunt lips and slid the head all over her labia. She then placed it at the opening to her little quim and growled "Fuck me Danny Boy."



Her pussy was so hot and extremely tight. She kept wiggling her fat ass on him until the head was engulfed and held there by her pussy muscles. Then Molly pushed down and groaned in pleasure as she took most of Dan's big cock into her. She wiggled her ass side-to-side again and finally swallowed all of him in her. She rubbed her clit on his pubic bone. Her nipples were hard as a rock. Molly leaned down and hotly breathed into Dan's mouth "Kiss me Mr. Anderson." She planted her full lips on his and their tongues probed each other. Damn, Dan thought, this little 16 year old girl kissed him more passionately than Dana did when they fucked and Dan always thought Dana was the best piece of ass he'd ever had but 16 year old Molly schooled him on that impression.



She slobbered all over his face as their tongues played tonsil hockey. Dan put his hands on her ass and guided her in the rhythm of their fucking. She began to breathe very shallow and her eyelashes sort of fluttered. She began to orgasm. Dan lifted his head and licked each nipple in turn and Molly exploded in cumming on his cock. She pushed and pulled against him until she was spent and she fell down onto his chest. Dan continued to pump slowly in and out of her by sliding her ass forward and back. Soon she was back and took over the rhythmic action of their fucking.



She grabbed his arms by the wrists and held his hands over his head. Her flay belly and small tits rested on his chest as she looked at him from inches away and started the filthy talk that drove him insane. "Like fucking this 16 year old pussy, don'tcha Danny Boy?" He just nodded. "Make me cum again Mr. Anderson," she pleaded like a whimpering little child. She was driving Dan crazy with her adult then child-like acts. He rolled her over and she spread her legs so wide he thought they'd pop from their hip sockets. She pulled him in by his ass even deeper into her. "Fuck yeah!' she squealed.



Dan began to pound her now and she was loving it. He withdrew almost all the way then shoved back into her pussy, her screaming in delight at each power thrust. Dan felt his load beginning to work its way from deep within his body. Molly was on a seeming non-stop orgasmic roll as she thrashed and squirmed beneath him. Dan slowed a bit and began to shoot his load into her tight and hot cunt. He pumped furiously as her pussy pulled hm ever deeper and seemed to lock onto his cock, not letting go. She opened her mouth and pulled his mouth to hers and she kissed him with reckless abandon.



Dan left all he had in this little girls hot, tight pussy. She held him tight to her as she caught her breath. She locked her legs around his waist and wrapped her arms around his back, holding him in place. She was kissing his neck and cheeks. Dan slowly lifted himself from her. Molly smiled up at him. "Oh my God! That was everything I thought it would be!" Dan breathed a slight sigh of relief that she had obviously wanted this to happen.



Dan stood up and stared at this fetching, naked and nubile young girl. She was sexy beyond belief and she knew it. She worked it. Dan suddenly felt uncomfortable in his post coital euphoria crossed with fear for all the unknowns as to what would come next. Molly laid there unashamed and naked, seemingly proud at her accomplishment of seducing her 35 year old neighbor.



"You sure can fuck with that big cock," she blatantly threw out. Dan felt a tiny bit of relief as it dawned on him the underlying meaning. "So, you've done this before?" "Oh God yes!" she adamantly answered. "My boyfriend Josh and I have been fucking for about 3 or 4 months now, but he's a kid . . ." she hung out there for Dan to ponder. "Not a real man like you Danny Boy." She smiled and Dan knew it was too late for him.



Dan realized this ultra sexual young lady was not a rookie lover but instead a vixen in the making. She got up and looking directly at him, approached him. She reached her little arms up and locked them around his neck as she pulled herself to him. "When are we going to do this again?" she cooed. Dan didn't know what to say. He looked at her wanting to take her again, but ever aware of what had happened and where it might lead if discretion did not become his watchword.



"i guess that's up to you Molly," he nervously smiled. Molly smiled too and looked like a pleasant thought crossed her mind. "Well," she said," I'm just glad it's June. We have all Summer to do this." She looked sort of concerned for a minute, lost in thought when she asked him "Did you like that Mr. Anderson?" He nodded. She smiled with glee. "Good then. My folks love to take day trips in the Summer with my little monstrous brothers, so I will have lots of free afternoons. Hope Mrs. Anderson has plenty of busy days with your kids," she added.



Dan considered her thoughts and wondered when the next opportunity would present itself and her to him. She started to slide back into her Spandex bike shorts. She purposely turned her back to him to highlight her ass being squeezed into the black shorts. She looked at him over her shoulder again and he was leering at her. "Oh, you like my fat ass don'tcha Mr. Anderson?" He just absentmindedly nodded agreement. She slid her waistband up over the generous ass cheeks then slid them back down teasing him. "Want this fat ass Danny? Ya want it don'tcha? You love my ass, huh? Do you jerk off a lot thinking about it?" He was shocked at her forwardness for being so young but her actions compelled him to admit she was a regular fantasy of his.



She slid the shorts back over her hips and let them fall to the floor. "Fuck me again, hard!" She fell to the floor in front of him and sucked his cock into her mouth again. She placed both hands on the shaft and put the swelling head into her mouth. Her lips bulged over it. She looked up at him as both her hands pumped his shaft as he hardened to full steel erection once more. She licked the head and stood and leaned back on the bed. She lifted her legs straight up and pulled her ass cheeks apart to show her open and swollen hole for him to enjoy. He crossed the two feet, knelt on the corner of the bed and slid his fat cock into her again. She then closed her legs almost together and put one leg on each side of his neck.



He held the backs of her thighs as he pumped. He then caught a glimpse of the dirty little souls of her feet and he fell back into the trance of vintage porn, wanton reckless sex and all the rest from his days jerking off in the attic. He began to lick her toes and the bottoms of her feet. She squealed in pleasure as he sucked each toe as he pumped her cunt. They rushed to orgasm, this time in unison they gushed onto each other. "Like my feet, huh?" she chided him jokingly, knowing she had yet another hold over this helpless man.



He explained all the ancient fantasies from his youth, more out of nervous chatter than to inform her, but she seemed to enjoy hearing it all. She really seemed interested and hung on every word. She then turned warm and sweet. "That is so hot Mr. Anderson." Then she looked at him very tenderly and said "I love you Mr. Anderson. I have for some time now. I want to be your little whore on the side. Don't worry. I will never tell your wife. I love you too much to hurt your life, but I have to have you whenever I can." For the first time it seemed Dan had the upper hand.



"Besides" she added, crossing to him as she slid her clothes back on, "I know you want me too. If we're cool about it, no one will ever know." He looked pleased and excited by the prospect of such a nasty future. "Like my hair in pigtails Dan?" she asked, her best little girl act in full display. He nodded he did. "I like looking like a sexy little girl for you," she hung out there. "I get really wet thinking about your big cock and knowing you want to shove it in my little tiny pussy. And I like being a little girl to your big strong man. Promise me it'll always be like this,"she childishly asked. Dan felt a wave of panic as he was now over the edge. She went on to assure him she was not some idiot love struck child but a woman/child who knew what her feminine charms were for and that they were all for him.



"This is going to be the most awesome Summer Dan." she said. She approached the back door and looked out carefully. "Okay, it looks like the coast is clear. I'll sneak back home and I'll see you outside in a little while. We just have to act like none of this ever happened." Then as she placed her hand on the knob she looked back and asked "This will happen again, right Mr. Anderson?" "I sure hope so Molly," he smiled. She ran to him jumped into his arms and kissed him. "I love you Dan Anderson" and she jumped down and ran out. Dan watched her quickly sneak across his yard next to the bushes and over into her own back yard.



He scratched himself and shook his head in wonderment. He watched her tight ass shake as she climbed the steps and went to enter her kitchen door. She looked up making sure he was watching her. She stopped, shook her ass from side to side and went through the doorway. Dan ran to the shower. After all, she said she would see him outside later, but she didn't say when. He hurried not wanting to miss her, a slight fear building in him, although he knew it was too, too late to alter it now.



For better or worse, come what may, he was enthralled by this little vixen.

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