The Babysitter Chronicles: Chloe's Story

  The

  Babysitter Chronicles

  Chloe’s Story

  By Jameson Targhee

  1

  Brad stares into the mirror. His hair is still mostly dark and mostly still on his head. It has thinned a little over the years and if you look hard enough you can see a gray strand mixed in here and there. He is 39 years old and tonight is another first date. Since his divorce was final a little over two years ago Brad has gone on more first dates than he can remember. There have been a few second dates but never any third dates. His friends think that he sabotages his chances for a relationship. Brad thinks his heart just isn’t in it. He thinks that maybe if he meets just the right girl, then just maybe his heart will speak up. So far his heart has remained silent.

  As he looks in the mirror Brad is pretty happy with what he sees. He wears his 200lbs on a 6’1” wide shouldered frame. Women have said he is a handsome guy but not available, meaning not emotionally available. He knows he should forget about his ex, he knows Wendy is in his past. Hell she can hardly be even bothered to spend time with their son, Max. Max was an oops, but the best oops that ever happened to Brad. Early in their marriage Brad and Wendy had tried to conceive but for whatever reason they were unsuccessful. Then when Wendy’s career started to take off, oops. That was eight years ago and the beginning of the end of their marriage.

  The Doorbell rang. That would be Chloe, the babysitter. Brad went downstairs to open the door and sure enough there was Chloe, 7pm on the nose. Chloe has been babysitting Max since she was fourteen. Brad and Wendy use to hang out with Chloe’s parents on a regular basis but since the divorce Brad didn’t spend as much time visiting. Didn’t want to be the “single” guy in need of matchmaking. He didn’t think Wendy kept in touch with them at all. Wendy’s new life was way too busy for old friends. New friends were much better. New friends in the right circles could lead to promotions and prestige.

  Chloe was eighteen now, in her last year of high school, and almost eye to eye with Brad. She stood just shy of six feet tall. Idling at the curb was a silver Avalon that belonged to Chloe’s parents. Brad waved to them.

  “Hey Mr. Hunter, I was wondering if I could stay at your place this weekend. My parents are going out of town and staying home alone is just creepy. Our house is way too big, way too many hiding places for bad guys,” Chloe pleaded.

  “For one, how many times of I asked you to call me Brad. For two, your parents have the best security system money can buy and for three, it’s okay with me if it’s okay with them.”

  “Thanks Mr. Hunter,” Chloe squeaked with an emphasis on the “Mister”. She ran to her parent’s car and grabbed her stuff. A large overnight bag and a guitar case. The guitar was a present from Brad. He got it for Chloe for her eighteenth birthday. It was a Martin Acoustics signed by Jewel and while it wasn’t cheap it was well worth it to see the huge smile that came across Chloe’s face. She was a big Jewel fan as well as an aspiring musician.

  Chloe’s parents were driving off as Brad shut the door.

  “Another first date Mr. Hunter?”

  “You never know, this could be a second date.”

  “Is it?”

  “No, but it could have been,” Brad said with a plaintive tone but a smile on his face.

  “Where’s Max,” Chloe asked.

  “He’s in the TV room playing something on the Wii U.”

  “Cool, maybe I will kick his butt at bowling again.”

  “I think he lets you beat him. He loves you and you play with him more than his mom ever has,” Brad said and Chloe blushed.

  “He’s a good kid and his mom is the one missing out.”

  “Yeah, she is,” Brad replied. “You know where the spare bedroom is. I will be leaving in a few minutes, should be back by midnight.”

  “Midnight? That’s early date. Are you even going to try to get some,” Chloe teased.

  “Chloe! We already established this was a first date.”

  “So, you’re a handsome guy. I bet you have no trouble getting a woman in bed.”

  “That’s not the point Chloe. I’m not looking for notches on my bedpost. I’m looking for someone special.”

  “You’re a good guy Mr. Hunter, you deserve someone special,” Chloe said before surprising Brad with a big hug. Brad was taken aback for a moment by the hug, his arms hanging by his side. When Chloe didn’t let go right away he returned the hug, holding her tight. Brad didn’t know if it was the conversation about first dates and notches on bedposts firing up his imagination but squeezing Chloe tight he felt a stirring between his legs. Chloe was a beautiful young woman and feeling her body pressed close to his he realized that she was longer a little girl. That and she smelled really nice, like peaches.

  Chloe broke the hug and gave him a kiss on the cheek, something easy for a girl of her height. She always like bigger more muscular guys and Mr. Hunter had muscle to spare. He made his money from martial arts, owning a small chain of Tae Kwon Do studios, or dojos as he called them. Brad had instructors that taught most of the classes now that the business had become so successful. He tried to keep up with all of the student’s progress, occasionally helping those struggling with technique and did one on one training with some of the advanced students. As Chloe left his embrace, she thought she felt something hard press against her waist.

  The feel of her lips against his skin didn’t help the condition between his legs. His cock was now throbbing with his erection. He could only hope Chloe didn’t notice and besides he didn’t need to be lusting after his eighteen year old babysitter.

  “Do you mind if I use the computer after Max goes to bed,” she asked.

  “Sure, do you remember the password to the profile I set up for you?”

  “Yeah, never changed it.”

  “Sounds good. Are you gonna play a song for Max for bedtime,” Brad asked motioning to the guitar, “he tells me you sing as well as you play.”

  “Yeah, he’s my biggest fan.”

  “He’s got good taste. I’m gonna go tell him good night then head out.”

  “Okay, see you when you get home,” Chloe replied as Mr. Hunter headed to the TV room. He was wearing tight stone washed jeans that showed an impressive backside.

  2

  Chloe walked into the TV room and saw Max blowing away aliens. He was a good kid and Chloe always enjoyed coming over here and babysitting him. It made for an easy gig.

  “Hey Max!”

  “Hey Chloe,” Max yelled in return as he paused the game and ran to Chloe for a big hug. “Do you want to help me shoot some aliens?”

  “Not sure about aliens but would be happy to bowl a few games,” Chloe compromised.

  “Sure, we can do that. Just let me get to the next save point.”

  “No problem Max, I’ll just sit and watch for now.”

  It took about another twenty minutes for Max to win that battle and save his game. Soon after they were virtual bowling on the seventy inch screen. They split the first two games and started on a third would be the tie-breaker.

  “I wish you were my mom,” Max said out of the blue.

  “You already have a mom,” Chloe replied.

  “Yeah, but I never see her.”

  “I’m sure work keeps her busy.”

  “Yeah, too busy to spend time with me,” Max said with a pout.

  “I’m sure your mom loves you bunches and would be here if she could.”

  “But I love you Chloe and you spend time with me. You could marry my dad and become my new mom.”

  Chloe laughed, “I don’t think you dad would want to marry me.”

  “Why not,” Max asked. “You�
�re awesome and you could sleep with dad in his room.”

  Chloe blushed, the innocent comment of an eight year old catching her off guard. To Max, sleeping meant just that. To Chloe, she triggered back to that something hard she felt when she hugged Max’s dad.

  “Max, someday your dad will meet another woman and you will have a second mom,” Chloe managed to say after a moment. Even though Max’s comment had nothing to do with sex Chloe now found herself thinking about Mr. Hunter in a different light. All the girls at school said he was hot but she never thought about it. Until now. He was almost forty years old but could pass for much younger. He had well groomed dark hair and strong muscles on a wide frame. She knew he worked out almost daily, doing kata for tae kwon do as well as some weight lifting. She also liked that he was tall. Being 5’11” Chloe was taller than most of the guys in her high school but with Mr. Hunter she could look up into those dark brown eyes of his, the color of oak bark.

  “Well, I still wish you were my mom,” Max reiterated.

  A little while later Chloe was tucking Max into bed.

  “Will you play me a song,” Max asked.

  “Sure, let me go get my guitar.”

  Chloe got her instrument and sat on the edge of Max’s bed. She started slowly strumming, thinking of the song lyrics in her head. She then began singing True Colors. It was one of her favorite Cindi Lauper songs. As she sang she could see Max drifting off to sleep and by the time she finished the song he was completely out. Chloe bent over and kissed Max on the forehead. She babysat a few different kids on a regular basis but Max was the one that got her thinking about a family of her own. Maybe someday she would meet Mr. Right and she wouldn’t complain if Mr. Right turned out to be a lot like Mr. Hunter.

  3

  Chloe put up her guitar and went into the computer room. She started doing research for her school project and by the time she was done it was a little after nine. Chloe saved her work and was about to shut down the computer when curiosity got the best of her. She clicked on the main pictures folder on the hard drive and saw a long list of family photos. There were folders from camping trips, amusement parks, holidays, and birthdays (especially Max’s). Some of Max’s birthday pictures even had Chloe in them. In fact for the last couple of years Chloe was in the birthday pictures with Max but not his mom. She had been out of town and unable to attend.

  Chloe was about to close out of the pictures folder when she noticed a subfolder called “Nudes”. She hovered the mouse over the folder icon and debated clicking. It was probably just a folder of internet porn that Mr. Hunter used to beat off to. She debated for another moment, curiosity about his porn collection getting the better of her, then clicked.

  A window opened and hundreds of thumbnails appeared. This was not internet porn. This was Mr. and Mrs. Hunter pictures. Some very mild and some very X-rated. It looked like they were from all over the place. Some were out in the woods, some were in hotel rooms, and some appeared to be from the master bedroom upstairs. These must have been taken before the divorce. Chloe hovered the mouse over one of the photos and the information popped up, including the date. That picture was taken over three years ago.

  She opened one of the pictures. It was both the husband and wife standing out in the woods. They were both completely naked and standing side by side. Mrs. Hunter was holding Mr. Hunter’s cock in her hand. Chloe was amazed by the size. She had only ever been with one boy and he was quite small by comparison. She opened another picture, this one with the couple on the bed upstairs. Mrs. Hunter was going down on Mr. Hunter. Her mouth was stretched wide open and she was deep throating. Her lips down to the base of his rod. Chloe wondered if someone helped take these photos or if Mr. Hunter had set up a tripod and timer.

  As she flipped through the different images, Chloe realized that she had become quite wet. She undid the button on her jeans and slid her pants and panties down to her knees. With her right hand she clicked on a close-up of Mr. Hunter’s prick deep inside Mrs. Hunter’s pussy. Chloe’s left hand played in the moist folds of her own wet snatch. She imagined having her own tunnel filled like that. She imagined Mr. Hunter looking at her with those deep brown eyes as he slid his manhood into her dark reaches. Chloe slipped two fingers into her soaking channel as she thought of Max’s dad. The man Max said Chloe should marry.

  Chloe worked her fingers faster and faster, her imagination placing Mr. Hunter there with her. Soon she could feel the beginnings of an orgasm. There was a building of pressure that demanded to be released. She shuddered as the pleasure overtook her and her vagina pulsed around her fingers. A small squirt of fluid wetting her palm. Chloe slowly withdrew her fingers and laid her hand on her belly, sitting there and enjoying the post orgasmic relaxation.

  A few minutes later Chloe took her clothes off and walked naked to the bathroom. It was a short walk and Max slept downstairs so it was a safe trip. Standing in front of the mirror, she looked herself and wondered if Mr. Hunter would find her attractive. She knew that he liked her as a person. He has always been nice and when he got her that guitar for her birthday she was amazed that he cared that much. The question was did he like her physically. Her blonde hair hung down nicely, just past her shoulders. Her breasts were large, although not quite as big as Mrs. Hunter’s. Chloe was on the basketball team, with her height she didn’t have much of a choice, so she stayed pretty fit. Her stomach was flat but her legs were curvy with muscle.

  She ran her hands over her breasts, feeling the weight of them, pinching the large pink nipples. She imagined it was Mr. Hunter’s hands and could feel the desire stirring inside her even though she had just masturbated. She ran a hand down between her legs, fresh moisture on her tender lips. She was coming up with an idea but first she would take a shower.

  Chloe got out of the shower and dried off. Looking through her overnight bag she found her pajama shorts and a camisole. Normally she would wear a bra and panties along with these when spending the night away from home. Tonight would be different though. She dressed in her skimpy night clothes and went downstairs to the living room. There was a comfy couch and she laid down with her kindle and decided to read while she waited for Mr. Hunter to come home. Hopefully he would come home alone. In the years since his divorce he never had brought a woman back to his house. At least not on nights that Chloe had babysat.

  4

  Brad dropped his date off back her house. There was no invitation to come in for a nightcap, there was no goodnight kiss. Some dates went better than this one but things never progressed any further than a little kissing. There were a few reasons for this. One, he had a bad habit of talking about his ex and their divorce, always a conversation laced with bitterness and never a good conversation for a first or even second date. Then there was Max, his son that was his life now. Some women were okay with that but many, especially in his age range, were expecting a man with grown up children or at least kids that were almost out of the house. They didn’t want to help raise a kid and that was their loss. Finally, he wanted more than just a one night stand. That might sound funny coming from a man but being a single parent he didn’t think it was the responsible thing to do. He didn’t want an angry woman banging on his door creating drama, thinking one night of sex meant more than it really did. He didn’t want to chance that kind of drama, not with raising Max. So he masturbated when the tension needing releasing. Sex would come again someday but it would come with a relationship.

  Brad pulled out of his date’s drive and headed downtown to the bar district. Normally he would have gone straight home but with Chloe staying the night he decided to drown his sorrows. Sitting at the bar he ordered whiskey sours, one after another, until the world felt like a better place, a little less depressing. At one point an attractive redhead had tried to spark a conversation but after a few one word replies from Brad she got the hint. Around midnight, with a nice buzz going, Brad decided to make his way home.

  5

  Chloe had fallen asleep on the couch, M
r. Hunter staying out later than normal, when the sound of keys jingling in the front door awoke her. She adjusted the left spaghetti strap of camisole off her shoulder and down her arm, then folded the fabric down so that the top of her breast was exposed. The nipple was barely hidden under the folded over fabric. She then laid on her right side and pretended to sleep.

  Brad was a little more buzzed than he originally thought and was having a hard time getting the key in the lock. He probably shouldn’t have driven but at least the streets had been clear and he made it safely. Finally the metal met the tumblers and the lock opened. He stumbled in and closed the door. Brad started walking for the stairs we he saw Chloe asleep on the couch. Without looking too close he thought she should have a blanket so he walked to the hall closet and got one. It was when he came back and stood at the couch that he really looked at Chloe. She was beautiful and sexy. Her long legs were mostly bare, her shorts just covering the very top of her thighs, and her top had slid part way down, exposing most of her left breast. The blanket fell from his hand and Brad fell to his knees. Without his brain having a chance to approve his next action, Brad bent over and kissed that exposed breast, his lips pressed to her soft skin for a moment.

  Chloe was playing asleep, curious what Mr. Hunter would do. She could smell the alcohol and knew why he was late. His date must have gone badly. Part of her knew she shouldn’t be happy about that but part of her was. She wanted Mr. Hunter all to herself. She felt his warm lips against her skin and a shiver of excitement ran through her body.

  Brad leaned back from the kiss and looked at Chloe, this beautiful young woman sleeping on his couch. Conflicted thoughts ran through his mind. He knew he had already done too much. He knew he should just cover her with the blanket. He knew he should go to bed. The conflict came in knowing that he also wanted to do more. He saw where her top was barely hiding the nipple beneath. He thought he could easily pull that side of her top a little further down and expose the nipple. It would be so wrong but the throbbing of his now erect manhood was pushing for action. Brad stayed there on his knees, looking down at Chloe, for what seemed like an eternity. Then his arm started to move.