Jessie Flanders checked the time on her cell phone as she neared the elegant Carter home. She was a minute early for her babysitting job. As she made the turn onto the Carter’s front walk, a cab pulled to the curb and blew its horn. She reached the door and was about to ring the doorbell when it popped open. A good looking woman in her late thirties dressed in dark slacks and sweater peered at her over her glasses.

“Are you the babysitter?” she asked.

“Yes I am,” Jessie said.

“The sitter’s here as well as the cab,” she called to someone behind her. She disappeared into the house.

“Very good,” said a baritone voice. A very slim and very handsome man of about forty years came to the door. His dark hair was short but stylishly cut. He had blue, half-lidded eyes. He was wearing a tailored tuxedo.

“You must be Jessie,” he said fixing her with a friendly smile. “I’m John Carter.”

“Nice to meet you,” said Jessie as she shook Carter’s hand.

The woman reappeared. She had a carry-on bag slung over her shoulder. “I’m so sorry to leave you like this,” she said to Carter.

He squeezed her shoulder. “Don’t be silly. The sitter’s here; we’ll be fine. Tell your sister I hope she gets well soon. They exchanged pecks on the cheek and a second later she was striding down the walk to the taxi.

“Thanks for coming on such short notice,” Carter said as they walked into the living room. His eyes roamed over the high school senior. Jessie was one hot babe. Not much over five feet tall, she had a D-cup rack and a waist that might be all of twenty inches. She was wearing an expensive looking navy top with a square bodice above shorts that fit her like a glove and showed off her exquisite legs. With what looked to be diamond earrings and a diamond pendant on a gold chain around her neck, she looked as if she was more ready for a night on the town than a babysitting job.

“Glad I could help,” Jessie said. And glad to charge you the premium price for that short notice, she thought. She eyed Carter’s butt as he turned to hold the door open for her. Not bad. She entertained a brief fantasy of him returning from where ever it was that he was going and making a move on her.

“Here’s a list of contact numbers,” Carter said, handing her a sheet of paper. He went through a pretty standard rundown of permissions, legal snacks and a maximum bedtime for his son. As he was winding down, a woman came down the stairs into the living room. She was stunningly beautiful. Her blonde hair was upswept and held in place by an emerald tiara. There were emeralds at her ears and throat. Her dress was a shimmering white gown. If she said that she had just stepped away from a “Vogue” cover shot, Jessie would have believed it. So much for her seduction fantasy. Why would Carter hit on the babysitter when this angel was around? But that was okay, Jessie rarely lacked for male companionship and she had plans.

Freddie, the kid she was supposed to babysit, appeared from the rear of the house and peered shyly into the room. He was as tall as Jessie, with a mop of brown hair and brown eyes. Jessie had seen him around the neighborhood. Usually, he was on a bicycle wearing a helmet, elbow pads, gloves and riding at a snail’s pace. He was also fourteen years old.

“He’s fourteen? He doesn’t look that old.” Jessie had said incredulously to her mother when she’d mentioned the Carters’ request for her services earlier that afternoon. “I wonder why he can’t take care of himself for a few hours.”

“Well,” said her mother, Alicia, a woman of enormous breasts and rotund figure, “I understand that Freddie was sickly as a baby and his mother is probably over protective. I think she’s scared for the boy to be alone. And I know you need the money,” she had added with emphasis.

Carter checked his watch as Freddy descended the stairs and stood by his father. “Okay, we’re cutting things close tonight. Jessie, this is Freddy...”

“Hey,” Jessie said.

“ ... and Freddy, this is Jessie. Be on your good behavior.”

“I will,” he said softly.

Carter turned to the vision in white. “Ready to go?” he asked.

“I think so,” she said as she drew a gossamer thin shawl around her shoulders and checked the clutch in her hand. “Hello,” she said to Jessie, showing her a dazzling smile. I understand that Freddie has been promised chicken nuggets and fries for supper. Can you handle that? You just throw it in the oven for a few minutes.”

“Oh sure,” said Jessie. “Don’t worry, I’m sure Freddie and I will get along.”

“Thank you, dear,” she said sweeping out the door.

“See you around midnight,” were Carter’s final words as they left.

Jessie turned to Freddie. He was small for his age and the oversized pajamas he was wearing emphasized the fact. The matching top and bottoms were covered in “Transformer” figures. His slippers were fuzzy puppy dogs. Her eyes wandered down to his crotch. Was that a round bulge running down his pajama leg almost to his knee? No, don’t be silly, she told herself. She was horny and had cock on the brain this evening.

“Want to watch television while I make the food?” she asked him.

“Okay, I’ll watch it in the den,” Freddie said quietly and then he disappeared through a side door and down some stairs.

Jessie heard the sounds of the Disney Channel from a television as she walked into the kitchen. She prepped the oven and got the chicken and frozen fries baking in short order. After making sure that Freddy was fully engrossed in his program, she called her boyfriend, James, on her cell.

James was a sophomore at a local college. He was a nice looking guy from a rich family, and he wouldn’t have had any problem getting dates with a bevy of college cuties, but high school girl Jessie was the one he wanted. In fact, he was enthralled by the beautiful teen. He spent no small amount of money on expensive dates and expensive presents to keep her interested. But he had another attribute that he brought to their relationship, something that Jessie really liked. It was his eight inch cock.

“Hey baby,” Jessie said when James answered.

“I guess you’re at your babysitting job,” he said flatly.

Jessie heard the tone in his voice. “Hell, I didn’t want to postpone our date. Mom practically promised that I’d show up.”

“Yeah, I guess, so how long will it be?” he asked.

“I’ll be stuck here until around midnight, so ... uh ... I thought you might want to come over here instead of waiting.”

“Hey, you’re the one who said never again,” James said reproachfully. Two weeks earlier, while she had been on another sitting job, they had been caught fucking wildly on the couch when the dad had come home early from a meeting.

“Well, after giving it some thought, I think Mr. Parker had been watching us for a while. You know, enjoying the show. I bet he never told his wife,” Jessie said. She’d been afraid that her babysitting credibility had been ruined forever. As it was, Parker had refused to pay her fee, but it was obvious that he hadn’t told anyone, especially his wife. Otherwise, Jessie’s babysitting connections would have dried up.

“Okay, babe, it’s your call,” James said, sounding perkier, “what time should I come?”

“Wait until a little after nine. He’s supposed to be in bed by then,” Jessie told him. “Call before you come to the door; I don’t want to have to explain you.” She gave him the address and hung up.

Jessie checked her messages and fooled around with her phone until the timer on the oven went off. She slid the food from its baking pan onto a serving dish, set out some plates and poured milk for the both of them.

“Dinner’s ready, Freddie,” she called down the stairs from the door to the den.

“Coming,” she heard a second later.

They sat on stools at the breakfast bar partially facing one another. “You eat most of it,” she told Freddie. She nibbled at her chicken and left the majority of the french-fries for him. She was determined to keep her dynamite figure and not become a matronly blob like her mother.

“After you eat, you can watch some more television and then it’ll be time for bed at nine o’clock, right?” she told him.

“Can I play video games?” he asked.

Jessie mentally reviewed the list his father had given her. He hadn’t forbidden them. “I guess that’s okay,” she said.

“Cool,” said Freddie. “I borrowed one from my friend Danny. It’s all about...”

In five seconds she tuned out his breathless description of the game. She didn’t care as long he didn’t get so wound up she couldn’t get him to sleep at a reasonable time. She was looking forward to a couple of hours alone with James. She liked that he was serving up his big cock at her beck and call. It would be exciting to get it on in a strange home ... again. They would have about two hours to fool around. She bet she could come at least a couple of dozen times while she drained that big fuck-toy he carried around in his pants. She’d make him bust his nuts until he was firing blanks.

Thoughts of James and his dick led her to glance at Freddy’s crotch. Again, it looked as if something fat and long was running down his pajama leg. Also, it looked as if he was hiding a couple of baseballs between his legs. The sight reminded her of her last birthday party. Her BFF, Cheryl, had given her a ridiculously large dildo as a present. It was made to sit upright, the base being a couple of big latex balls flattened on the bottom and hollowed to act as a suction cup. It was meant to be a gag, but Jessie had actually masturbated with it a couple of times. The thing was much larger than James’ big cock, but to her surprise it fit her pussy easily once she was wet and excited. But the oversized dildo never warmed, and she had to use it in such an awkward position that it was hardly worth the effort.

Jessie brought her mind back to the present. Freddie was still babbling about his game as he wiped up what must have been a teaspoon of ketchup with his last french-fry. She realized that he had been talking to her chest most of the time. Her lip curled in a small smirk. He might be immature for his age, but Freddie was acting like a boy in his mid-teens in that respect. A lot of men failed to make eye contact with her when they conversed. She didn’t mind most of the time. Her impressive chest had let her get away with a lot of stuff such as late school work, traffic tickets and the like.

“Okay,” she said as he popped the fry in his mouth. “If you’re going to play that game before bed you better get to it. I’ll clean up here.”

“Thanks for fixing supper,” he said as he slipped of the stool and trotted out of the kitchen.

Jess heard him padding up the steps, to his bedroom she assumed. She checked her watch and saw that she had time to kill. She cleaned their dishes and the baking pan she’d used. She even went over the kitchen counters. They had looked less than pristine. After that she got her purse and went into the downstairs toilet. She emptied her bladder and then checked her look in the mirror. After running a brush through her hair, she put some gloss on her lips to make them look wet and inviting. She touched up her mascara just to even out a spot.

She knew that James would hardly notice any of that, but he might this, she thought with a grin. She put her hands beneath her breasts and lifted with a rolling twist of her shoulders, moving her tits fractionally higher. She was wearing almost a hundred dollars worth of underwear. Her demi-bra was a satiny light blue model with the padding guaranteed to add a cup size. She certainly didn’t need help in the size department, but she liked the way the extra material made her boobs look as if they were about to spill out of the satiny cups. Her matching panties were daintily fringed hip huggers that left no lines to mar the view of her excellent ass.

She went down into the den and settled on the couch. She found a movie on the television and became so engrossed in the teen love drama that she jumped when her cell rang. It was a few minutes before nine. “I’m outside in the car,” James told her. She ran upstairs to the ground floor and looked out the front window. James waved to her from the curb and she waved back.

“Hang on, let me check,” she said.

She went upstairs and found the open door of Freddie’s room. She couldn’t help but smile. It looked as if he had been sitting on the edge of his bed to play his video game and had simply keeled over in mid-game. She carefully took the controller from his hand and put it near the game console. Gently as she could, she swung his legs onto the bed and covered him with a blanket. His mother might fuss that he wasn’t between the sheets, but Jessie wasn’t about to wake him. She turned off the console and television, then she went to the door and turned off the overhead light. She was amused to see a nearby nightlight in the shape of a toy robot begin to glow. She quietly closed his door and lifted her phone.

“Meet me at the door,” she told James eagerly.

When she opened the front door, James slipped inside. He took one quick look around and grabbed Jessie around her waist. He slipped his tongue in her mouth even before their lips met. For a full minute they kissed hot and wet and deep. His hands were all over her ass and tits. He was already hard and let her know it in no uncertain terms by grinding the length of his thick dick against her tummy. “Jessie, I want you so bad,” he said when they came up for air. “Is your baby asleep?”

“He’s hardly a baby,” Jessie said, “but, yeah, I think he’s out for the evening.”

“Cool, I brought this,” he said, holding up a plain black DVD case that Jessie hadn’t noticed.

“And that is?” she asked. She was a little miffed that he wasn’t immediately ready to strip off her top and worship her lavishly dressed tits with eager kisses.

“You’ll see,” he said. “Where can we play this?”

“Down here, I guess,” Jessie said. She led the way down to the den and pointed out the flat screen TV sitting atop a cabinet full of electronic gear. It took James a minute to find the DVD player, get it to run and switch the television input.

They snuggled close on the sofa as on the screen an elegantly dressed blonde, her generous breasts practically spilling from her evening gown, and a handsome man in evening wear walked furtively down a tastefully decorated hallway. The subdued sounds of a party could be heard in the background. The woman opened a door and they darted into a private library fit for a mansion. The couple embraced and kissed passionately; tongues flashed back and forth. The man lifted a full, creamy breast from her gown and kissed it eagerly. Her gloved hand went to his crotch and pulled his fully erect cock from his pants. His hard-on stood practically straight up from his black dress pants.

“Mmm, nice,” Jessie said. The well groomed man had an impressive dick, even for a porn star. It was long and thick with a slight upward curve. She couldn’t help but think of the elegantly dressed Carters. She wondered if his cock would rear out of his trousers as impressively large as this guy’s. Probably not, but you never knew.

“I thought you’d like it,” James said with a laugh.

The woman went down on the man; her lips engulfed his cock-head while her gloved hand stroked his shaft. From time to time she would look up to gage her partner’s excitement as she massaged his balls. After a couple of minutes, the man pulled her to her feet and unzipped her gown. He kissed and caressed her big tits as the gown fell to the floor. The scene shifted; now the woman was bent over the corner of a large desk. She moaned softly and her big tits swayed as the man plunged his thick dick into her exposed pussy. Her gown had disappeared, but she was still dressed in dark hose, gloves, garter belt and heels, pearls dripped from her throat and ears. Her tight, shapely ass moved to meet his thrusts. He was still fully dressed, standing tall and thrusting away as if he could do it all night.

The door to the library opened and another man stepped into the room. His only reaction to the couple having sex was a raised eyebrow. The couple didn’t even pause in their fucking as the second man approached. He simply pulled down his zipper and exposed a cock fully as hard and large as the first man’s. The woman took him in hand and began to suck him off.

Jessie liked the view of the two oversized cocks as they plowed into the enthusiastic blonde. The truth was though, she was horny and she wanted some attention from James. “Your cock is almost as big as theirs,” she said in a clinical voice designed to tease and draw a response.

“What do you mean almost?” he said, and he was serious. He knew that as much as he was in love with Jessie, she was drawn more to his cock and money than any amorous feelings.

Jessie stood and fiddled with the buttons on her shirt. “I don’t know,” she said. She decided to tease him. “Why did you bring that DVD? Need a little stimulation to get it up?” she asked, knowing very well that he’d had a hard-on from the moment he’d come in the house. “Did you screw some other girl this afternoon?” As she spoke, she stripped off her top. She tossed it onto a nearby chair and then posed to give James the full effect of her breasts as they mounded over her bra cups.

“Oh baby,” James said. Jessie was more than a match for any centerfold he’d ever seen. She was tanned and fit; her softly muscled abs sat above full hips. “There’s no one but you,” he said a bit desperately. He quickly unbuckled, unzipped and brought his turgid cock into the open.

“Maybe I was wrong,” Jessie said slyly as she eyed his excitement. She had worn a pair of cuffed linen shorts that would have looked quite demure and fashionable except for the fact that they had a one inch inseam and were molded to her ass. She liked the way James was hungrily eyeing her tits. She did a strip tease with her shorts, slowly sliding them off her hips, turning to show off her tight ass cheeks. When her shorts hit the floor, she flipped them to the side with her foot. She was wearing wedge sandals with three inch heels. She liked the way they added to her height, but she especially loved the way they made her legs look. They were tanned and smooth and the muscles stood out just right. She posed left and then right, putting her hand on her hip and resting her weight on first one foot and then the other like a model at the end of the runway.

And then she saw Freddie.

Somehow, in the midst of her erotic tease, he had simply appeared in the den. That put him behind the sofa where James sat stroking his fat cock. Freddie looked very much like a kid awakened from deep sleep. His oversized pajama bottoms slouched at his waist and covered his feet. His pajama top was fastened by only the two top buttons. The voluminous sleeves hung to his fingertips. His bleary eyes shifted back and forth from Jessie’s gorgeous form to the porn stars screwing away on the TV.

The one thing that really caught her attention though, was whatever was tenting the front of Freddy’s PJ’s. There was no fold-in-the-fabric explanation for this. It was long and pulsing and looked as if it might push a hole in his pant leg.

Freddy unconsciously reached down and adjusted himself. Now the bulge was sideways, but still moving and growing. It jerked upright like the second hand of a clock. It seemed to hang up when it reached the waistband of his PJ’s, but then it popped free and swept to the twelve o’clock position. Jessie couldn’t believe it. Freddy’s cock was not only tenting the front of his pants; it was tenting his pajama top too. She could see some of the shaft between the open halves of the top – his cum-tube looked as big as her forefinger. The most amazingly sexy thing was that she couldn’t see his cock-head. It was hidden by his half-close pajama top and had to be halfway up his chest.

“I woke up and got scared,” he said. “I thought maybe you’d left.”

James jumped at the sound of the voice behind him. He hastily stuffed his cock back into his pants and zipped up. He glanced over his shoulder just long enough to get a glimpse of Freddy. “You’re babysitting him?” he asked incredulously. “He’s no baby.”

“I told you he wasn’t,” Jessie said as she eyed Freddie. “And he certainly isn’t,” she continued as she wet her lips and twisted a finger in her hair, wondering how she could get a look at what had to be his monster cock.

“Shouldn’t you ... you know ... put your clothes back on?” James hissed at her.

She responded by turning so as to give Freddy the full effect of her amazing figure.

“Is that porn you’re watching?” Freddy asked.

Jessie saw James scramble for the remote – no doubt to turn off the erotic action on the screen. She held out her hand for him to stop. “Yes, and you can watch some more if you promise not to tell your parents.” She sure as hell didn’t want to miss another fee.

“Okay,” he said, clearly happy with the deal. His eyes continued to flick from the screen to Jessie and back. “She isn’t as pretty as you, but you both have big boobies.”

Jessie laughed. “Thank you,” she said. She ran a finger down her cleavage and across the mounded flesh of her left breast. “I think you like big boobies,” she told Freddy.

“Yeah, they’re great,” he said. He lifted his hand until it hovered above the spot where his cock-head pressed against his pajama top. He glanced guiltily at Jessie.

“Go ahead, it’s only natural,” said Jessie using the gentle, encouraging tone of voice she usually reserved for toddlers.

Freddy went ahead and rubbed the material of his pajama top over his cock-head. He frowned; it looked as if the stitching or something else was bothering him. He unfastened the last two buttons of the top, and with Jessie’s smiling encouragement, he slipped it off his shoulders.

“Ohmygod,” sighed Jessie. Freddy was a skinny kid with pipe stem arms and legs. That, by contrast, made the sex tool that jutted upward from his groin only more impressive. The shaft was as thick as the proverbial soda can and the head, which was hovering at mid-chest height, flared even larger.

Freddy’s gaze shifted back to the widescreen. The well endowed starlet had screamed her way through an orgasm; her cries being muffled by a mouth full of cock. Now she moved to the desk’s high back, leather covered office chair. She sat and crossed her nylon sheathed legs, looking very regal as the two men went to her side and furiously pounded their dicks. They came within seconds of one another. One man dropped four long globs of milky semen on her right tit while the other, younger, fitter man managed six thick streaks of cum across both of her enhanced breasts. They were impressive money shots even for a couple of porn pros.

“Did you like that?” Jessie asked Freddy.

Freddy shrugged, indifferently. “Their things are kind of small and not much came out,” he said.

James snorted and raised up enough to turn his head and, this time, to take a good look at the boy who was standing behind the sofa. After a couple of seconds, he dropped back down, his eyes wide in shock. “Can’t you send him back to bed,” he said to Jessie through clenched teeth.

Jessie gave him a look that told him to shut up and be still, she was in charge here. “Not much came out?” she reiterated to Freddy. He nodded. “So more than that comes out when you masturbate?”

He gave her a sheepish grin, realizing that he had just admitted to his babysitter that he masturbated. Not that it should have mattered as he was jerking with both hands on his mammoth rod right now.

“More than they make?” she said sweetly. “Well, it sort of builds up after a while. You must not do it very often.”

Freddy heard the challenge in her voice. “I sure do make more than they do. And I can do it two or three times a day,” Freddy corrected her.

Jessie’s heart raced and she could feel the sexual heat building in her body. If what he said was true, then this fourteen year-old was a walking cum machine. She wanted the full view of his cock and the rest of his package. She walked to him making sure that he got the full effect of her swaying hips and bouncing boobs. His eyes locked on her body. “Why don’t you get rid of those old pajama bottoms?” she said.

He looked significantly at the top of James’ head. Jessie shrugged and winked. She made a dismissive wave of her hand at James; one that James couldn’t see. Freddy obediently pushed at the waist band of his pants and the loose material fell to the floor.

“Ohhhh myyyy godddd,” Jessie said in amazement. She had been looking at only the upper two thirds of the boy’s cock. Now it was revealed in all its awesome glory, and the balls that swung between his legs matched it completely in their bulging size.

“What?” said James as he finally gave up on ignoring the so called boy who was consuming his girlfriend’s attention. He turned on his knees and looked over the back of the sofa. The sight of a cock and balls that looked as if they belonged to a giant made his jaw drop.

On the television, in a different setting, a porn star was titty-fucking a starlet with massive breasts. Freddy had stopped paying much attention. He stroked his cock with both hands. His babysitter was in her pretty underwear, which showed an exciting amount of her boobies. He even liked the awed look her boyfriend was giving him. A glob of pre-cum lurched out of his cum-slit and flowed down his cock-shaft until his hand caught it and used it for lubrication. The glob was quickly followed by another and another.

Jenny loved the way Freddy’s eyes devoured her breasts. He was hardly the first male to do so, and not even the first one to jerk his cock at their sight, but he was certainly the most hung. She ran her hands over her tits and gave them a squeeze. “Do you like these?”

Freddy nodded as a fresh surge of pre-cum flowed over his fingers.

James charged around the sofa and stood at Jessie’s side with his back to Freddy. “Why are you coming on to this kid? Send him to bed,” he hissed in her ear.

Jessie frowned and turned to James, although her eyes never left Freddy’s long column of sexual power. James’ attentions no longer seemed so important to her, but she didn’t see any reason not to string him along. “The further we suck him into this, the less likely he’ll be to tell his parents,” she hissed right back, her voice hidden by the passionate moans coming from the TV.

“But...”

Jessie stopped his protest by grabbing his crotch. Her eyes met his and she said, “You’re as hard as an iron bar. Don’t tell me this isn’t turning you on.” James’ mouth opened, but he failed to find any words. “Play along,” she said in finality.

James grunted in frustration. He took a seat, but not back on the sofa. With his arms crossed and a pout on his lips, he dropped into a chair where he could keep an eye other two.

Freddy smiled at his babysitter. It looked like her boyfriend did whatever she said. It felt so good to wank his cock, especially because Jessie was watching. He liked the way her hips swayed and the way she rubbed her boobies – her great big boobies. His cock was so hard. He had lost his load twice already today, but his dick was as hard as ever at the sight of her unbelievable figure.

Freddy felt the pressure building in his balls and cock. He knew that if he stopped now, his package would ache for hours, but he didn’t have any intention of stopping. Jessie was a goddess in sexy lingerie. She was about a million times hotter and more real than the models he usually jerked off to from his mothers fashion magazines. She certainly wasn’t freaking out about his nudity and the fact that he was beating his meat right in front of her and her boyfriend. In fact, she looked eager. In fact, she looked really, really eager since he could see her fingers slip inside her panties, and a look of utter pleasure appeared on her face.

That set him off. Freddy’s cock-head turned dark red and expanded. Pre-cum leaked like someone pouring clear syrup from a bottle. His cum-slit spread like a small mouth. A couple of twitches of his groin filled his cum-tube and then his well exercised cock muscles flexed. Pure white teen-cream leapt in a stream from his amazing cock. It arced through the air and landed with a long splat near Jessie’s feet.

“Eeee,” she squealed in delighted surprise. Her feet danced as flecks of cum splashed on her bare ankles. Freddy had just produced more cum than James could make in a week, and yes, she had a good idea of how much that could be. Her boyfriend couldn’t get enough of her pussy. Many times they had fucked until he could coax only a few watery drops of cum from his exhausted dick while Jessie sat on his face and got off on his tongue.

Freddy’s cum cannon fired again. “Ohmygod, what a load; I can’t believe you can make so much,” she said in awe. Her jaw dropped as she watched the teen send stream after long stream of cum flying through the air, his face a rictus of near unbearable pleasure. She stretched out her arm and let one of the thick cum-strings hit her palm. Rubbing the teen-cream between her fingers, she told a stunned looking James, “It’s hot and feels creamy.” She licked at her fingers, “Sweet too.”