Amber and Jack Ch. 02

Authors Note: Chapter One of this story can be found in the "First Time" category and is entitled (obviously) Amber and Jack Ch. 01.

Amber's legs immediately prickled up with goose bumps as she stepped out of the gymnasium and into the chilled October air. That was one of the downfalls of the volleyball shorts she wore to practice. Yeah, they were super short and showed off her ass and year-round-tanned legs, but walking outside could get a bit chilly.

"You're still coming over tomorrow night right?" her friend asked her as they walked along the sidewalk.

"That's the plan," Amber responded.

"Great." Seeing that Amber was continuing to walk along the sidewalk, rather than venturing into the parking lot her friend continued. "Hey, is your car still crapped out? Do you need a ride home?"

"Nah, its fine. I'm babysitting for the Callahan's tonight and they live just around the corner," Amber said.

"You sure?"

"Positive. It's really not that far. Some fresh air will be great."

"Okay then. See you tomorrow!" Lindsay called over her shoulder as she reached her vehicle.

"Bye." Amber followed the cemented path around to the front of the school. Truthfully, the walk from her school to the Callahan's house was a fairly simple one and would not take more than ten minutes. As the front lawn of the school came into view, Amber noticed a familiar car sitting in the parking lot.

There he was, the man who, less than forty-eight hours ago had his cock buried in her snatch. He was leaning with his back reclined against the hood of his black vehicle, sunglasses shielding his eyes and his tie loosed around his neck.

"Hey Mr. Callahan," Amber said as she got closer. "What are you doing here?"

"Offering you a ride home," he responded simply. Seeing confusion written on her face he felt the need to continue. "I figured your car was still out of commission and I got out of work a bit earlier than expected. I remembered that you said you had volleyball practice today, so I figured I'd offer to pick you up."

"Well thank you," she said graciously. "That's very nice of you. Unnecessary, but nice, none the less."

"It's no problem at all."

And in that moment, he was suddenly very glad he had decided to leave the office a little early in hopes to catch Amber on her walk home. If he thought the shorts she had on the other day were cock-twitch-worthy, these shorts could possibly make him cum his shorts on sight. The tight elastic fabric hugged her body tightly and extended to only just below the curve of her ass.

"How was practice?" Jack asked as they climbed into the vehicle. He could see a slight glisten coating her skin and for some reason the idea of her working up a sweat turned him on ever so slightly.

"Not too bad," Amber answered. "We had to run a mile and a half. Then we did some conditioning in the gym and played a scrimmage."

"Did you win?"

"Of course!"

Jack turned left out of the parking lot and into the neighborhood in which his house was nestled.

"Oh, I love this song!" Jack said turning the volume up on the radio slightly. "Do you mind?"

When Amber shook her head, rather than turning right onto his street, Jack went straight through the stop sign. Amber glanced at the clock on the dash and relaxed into her seat when she saw that it read only two minutes after five. With her eyes closed and her head resting against the head rest of the seat, Amber's mind wandered to what happened last time she was sitting there. The memory caused her pussy to contract in excitement. The idea that the man in the seat next to her was the one to claim her virginity caused a warmth to radiate from her center. Being so close to the first cock that entered her caused a wetness to begin to form between her legs

Amber watched the replay through her mind until she felt the car come to a stop. She opened her eyes, expecting the Callahan home to come into view. Instead, she saw nothing but trees. "Where are we?" Amber asked as she looked around.

"Have you never been here before?" Jack asked cutting off the engine of the vehicle. "They used to have a park here, but they took all that out. They put in some benches and tables and a path around the lake. And on the other side of those trees is an open area and people come and do yoga, or run along the path. But at this time of day it's quite peaceful."

"It's nice," Amber agreed as she followed Mr. Callahan's lead and stepped out of the vehicle.

"I sometimes come here after work," he started. "You know, get a few moments of quite between work and going home. I thought you could maybe use a few moments to decompress. Since you get to entertain my children tonight." That statement caused a giggle to escape from Amber's lips.

She continued to follow Mr. Callahan across the grassy area, towards a slightly wooded area, through which Amber could see the lake that he had mentioned earlier. Amber lengthened her stride for a few steps until she was walking side by side Mr. Callahan.

"Your ass looks fantastic in those shorts," Jack said, a low growl in his voice, after glancing down and taking a prolonged glance.

Without saying a word, Amber's hands reached behind her body and grabbed onto the black fabric. She pulled slightly, allowing the fabric to move and repositioned the hem of the shorts a little further up, causing the bottom curve of her ass cheeks to no longer be covered. As she saw Mr. Callahan watching her intently, she winked in his direction.

As soon as the duo had stepped through the wooded area that kept the lakeside path from view of the street, Jack's hand planted itself on Amber's ass. He squeezed slightly as Amber turned her body and pressed her chest into his. Her lips immediately found his and Jack wasted no time sliding his tongue into her hot mouth.

Amber slid her hand down the side of his body, finally slipping it between them at waist height. Her small hand landed on the front of his trousers and her palm flattened against the hardening bulge she felt beneath. As their tongues continued working against each other, Amber's hand began rubbing softly, squeezing just the right amount.

Jack could feel his cock hardening even more and pressing against the seam of his pants.

When he was sure his cock was going to rip through the material of his pants, suddenly he felt Amber's hand leave his hardness and make their its way a few centimeters north and land on the button. She deftly unthreaded the button and unzipped the zipper and slipped her hand into his pants.

"Mmm," Amber moaned into Jack's mouth as she began rubbing his cock through the thin material of his boxer briefs. "Is this for me... Mr. Callahan?" Amber asked sweetly, slightly nibbling on her plumped bottom lip.

"Fuck!" he swore. Amber quickly moved her hand to the waistband of his underwear and slipped her hand below the fabric. Feeling her soft fingers against his hard cock caused Jack to let out a low moan.

Working in the confined space within his pants, Amber wrapped her hand around the hardened length and moved it up and down ever so slightly. Deciding that she wanted more room to move around on his cock, Amber slowly began stepping forward, causing Jack to step backwards until they were back into the wooded area. The added layer of protection allowed Amber to use her other hand to pull Jack's pants down slightly.

Finally, she was able to stroke his whole length. "Your cock is so big," Amber said, her breath fanning across his face. Before Jack knew what was happening, he watched as Amber lowered her body slowly until she was on her knees in front of him. While her right hand remained wrapped around the base of his cock, Amber stuck her tongue out slightly and licked the few drops of pre-cum from the head. "And so delicious," she added.

Amber wrapped her lips around just the head of his cock, and swirled her tongue around its circumference. With her lips puckered around his hardness, her tongue stroked the underside of the head a few times before she removed his length with a soft suckling kiss to the tip. Amber placed more suckling kisses down the side of Jack's cock, from the tip to the base. As she reached the place where his shaft connected to the rest of his body, Amber's hand wrapped around the head of his penis and she lifted it up ever so slightly. With the underside of his cock more exposed, Amber's tongue flattened itself against him. Her tongue dragged along the length of his hardness, until she was back at the tip.

Amber playfully licked around the head, purposely not allowing the length to enter her mouth. Jack's hips thrusted slightly in her direction and his cock pressed into her cheek. Amber's eyes trailed up Jack's body until her eyes met his. A quick wink from her right before her mouth wrapped around his cock caused his cock to twitch slightly.

Her head bobbed up and down a few times, each time taking more of his length into her mouth. With her mouth working up and down his cock and her tongue rubbing against the underside, Amber's right hand wrapped around the base and the three movements began working together in sync. "Fuck," Jack swore out loud.

Amber suctioned a bit tighter around Jack's cock, sucking harder as her mouth slid up and down the length. Jack felt himself nearing orgasm, and attributed the quickness to the fact that he had not stopped thinking about fucking Amber since the moment he walked out of her house two days earlier. The sight of her, on her knees in front of him, his cock sliding in and out of her hot mouth only heightened his need to cum.

Almost as though Amber could read his mind, she slowly pulled his cock out of her mouth, but continued working her hand up and down its length. "Mr. Callahan," she began, not raising from her knees, "Your cock is so delicious, but I haven't been able to stop thinking about you fucking me again."

"Stand up," Jack ordered sternly. A smile worked its way across Amber's face as she stood up and Jack's lips pressed urgently into hers. His cock pressed harshly into her stomach, as he grabbed the waistband of her athletic shorts. Jack pushed them down her toned legs, leaving them to rest around her knees. Wanting her legs spread apart further, Amber used the toe of her right shoe to drag the material down her leg until she could pull one of her feet free of the spandex.

As much as Jack wanted to cum in Amber's mouth, on her tits, hell all over her eighteen year old body, the thought of filling her with his cum right before leaving her to babysit almost made him lose it right there. Amber stepped forward so that her hands were now resting against the tree that she had previously pushed Jack against.

Bending at the waist slightly, her hands pushed into the trunk of the tree to keep her balanced. Not bothering to remove her panties, Jack's hand pushed the material aside and his fingers pressed into the skin between Amber's legs.

"Someone is excited," Jack said deeply as his fingers worked into her wet slit. His fingers were practically drenched as he worked them against her slightly.

"I told you, I haven't been able to stop thinking about your cock since Tuesday," Amber said as a moan escaped her lips. His fingers felt amazing working against her pussy and he hadn't even entered her yet.

"So, you've fingered yourself," Jack said pushing a finger into her, "Wishing it was my cock. thrusting in and out of your delicious pussy, huh?"

"Yes," Amber moaned.

That was all Jack needed to hear, his fingers gripped her hip as he stepped forward easing his cock into her. "God damn," he muttered as the head slid into her tightness. She was even tighter than he remembered. Amber's back arched a bit, sliding Jack's cock into her without him moving. Getting the hint, he pushed forward, until his hips connected with hers.

Feeling his cock completely buried inside of her, Amber moaned out, "Yes." Slowly, Jack slid his cock away from her, before slowly reentering her.

"Faster," Amber muttered, pulling her bottom lip between her teeth. More than happy to oblige, Jack began thrusting in and out of Amber at a slightly faster pace. Her back arched with each thrust, pushing her hips back into Jack's, urging his cock deeper into her pussy.

"How does my cock feel?" Jack asked, desperately wanting to hear her moan his accolades while balls deep in her snatch.

"So. Fucking. Good." Amber said shortly with each thrust. "I. Love. Your. Cock." After a moment's pause Amber craned her neck, looking over at Jack and added, "Mr. Callahan."

Something about the way she 'angelically' added his name caused Jack's hips to increase speed. His cock plowed into her tightness with added pressure and speed. "Ughnn!" Amber moaned out, as her hands gripped onto the tree she was holding for balance. Looking down between them, Jack's eyes fixed on his cock sliding back and forth. Watching it sliding out, slick with wetness, both hers and his, and then disappearing back into her, Jack gripped her hips harder, his fingers digging into her flesh.

Amber was almost certain that she was going to have five bruises on each of her hips, exactly the sizes of Mr. Callahan's fingertips, on her the next day, but frankly, she didn't give a damn. All she cared about was the cock that was plowing in and out of her at a most satisfying pace. With her eyes closed and her arms extended in front of her, Amber let out and audible gasp, as she felt one of the hands remove itself from her hip and snake around to the front of her body.

As Jack continued to thrust his cock in and out of Amber's pussy, his right hand slid down across her stomach and maneuvered between her legs. A smirk crossed his face as he heard Amber gasp as his index finger touched her clit. He felt her pussy contract around his cock in response as he gently rubbed his finger back and forth.

"Cum," Jack growled as Amber's pussy continued contracting against his cock, knowing that he was nearing his own orgasm.

A few more thrusts of Mr. Callahan's cock and Amber felt a warmth beginning to build low in her stomach. "Shit. Shit. Shit. Shit," she muttered out, the finger on her clit starting to move faster. Her eyes clamped shut and her methodical hip rocking ceased as twitches took over. "I'm cumming!" Amber moaned as her pussy contracted even more.

Her hips continued to twitch as Mr. Callahan continued fucking her pussy through the duration of her orgasm. "Cum in me," Jack heard Amber mutter through ragged breaths. Jack smiled, as though there was any other option just as his cock expelled its first spurt of cum. His hips sloppily thrusted back and forth, as rope after rope of cum buried itself into Amber's eager pussy.

As he felt himself soften slightly, no doubt due to the extreme amount of his cum that now resided in his eighteen year old babysitter's pussy, he removed his cock from Amber and watched as she adjusted her panties. Jack had no doubt that they were already wet and were going to stay that way for the remainder of her evening. With her athletic shorts still wrapped around one of her sneaker clad feet, Amber turned around, her legs still a bit shaky and lowered her body again.

Dropping to her knees, Amber's tongue traced its way down the length of Jack's cock. She licked his cock clean, enjoying the taste of her own wetness mixed with Mr. Callahan's cum. After she successfully licked every inch of his length, she stood up (with a little help from Jack), and pressed her lips against his. Her tongue offering him a taste of their combined juices. "Mmm," Jack moaned against Amber's lips as she pulled away.

"We probably should get going," Amber said as she pulled her volleyball shorts up her legs and positioned them, making sure her ass was covered. Jack pulled his trousers back up to his waist and made sure his fly was fully closed as the two of them reemerged from their secluded spot in the woods. They walked back across the field and made their way to Jack's car. Climbing into the vehicle, they read the clock on the dash. "I'm supposed to be at your house in three minutes," Amber said with a smile.

"No problem," Jack replied starting the engine. As the car backed out of the parking lot, Jack reached into the center console and grabbed a pack of breath mints. He quickly popped one into his mouth before extending the tin towards Amber, who graciously accepted one.

"To cover up the scent of cum on your breath," Jack explained with a smile causing Amber's filled pussy to contract tightly.

A few turns later, the car turned into driveway. Grabbing her duffle bag from the backseat, Amber followed Mr. Callahan towards the house. "Look who I found," Jack said with a jovial tone as he kissed his wife quickly on the lips.

"That was convenient wasn't it?" Mrs. Callahan said as she stepped to the side, letting the duo walk through the entry way. "That way you didn't have to walk here, since I'm assuming your car is still causing you issues."

"Yeah," Amber said sliding her shoes off and leaving them against the wall.

"Are you okay sweetie?" Mrs. Callahan asked as Amber used the wall to steady herself, her legs still shaking a bit beneath her. "You look a little shaky."

"Oh, I'm fine," she quickly reassured her. "We just ran a lot at practice today. I'm just a little uneven on my feet right now. I'll be fine though. Promise."

"Well, please have some Gatorade or something in the fridge," Mrs. Callahan began, "and make sure you eat something for dinner."

Amber nodded her head and refrained from looking in Mr. Callahan's direction. She knew that a smile the size of Texas was plastered across his face, listening to his wife tell her how to regain her composure after his cock sent her over the brink of orgasm not five minutes ago.

"I will," Amber agreed. "Anything special I should know for tonight?"

Mrs. Callahan gave Amber some basic notes about the kids' homework for the night, knowing that Amber knew all the phone numbers and television rule already. After Mrs. Callahan stepped into a pair of black pumps, Amber wished the couple a fun time and made her way to the den while they headed for the front door.

One final glance over his shoulder was all Jack could take as he walked through the entry way and towards the door. Knowing that Amber was currently sitting on his couch, his cum still warm inside of her was going to keep his cock at semi-full attention for the entire evening.

"Thank God for her broken car" Jack thought to himself with a smirk as he held the passenger door open for his wife before walking around and climbing into the driver's seat.