The Sitter Ch. 02

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Emily helps a boy discover his potential
13.2k words
4.74
111.7k
91

Part 2 of the 2 part series

Updated 10/30/2022
Created 04/21/2013
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"Sex is like air; it's not important unless you aren't getting any." – John Callahan

Emily Parsons was feeling great. The late November snow outside the windows was falling slowly, occasionally sticking to the glass and melting before her eyes as she sat in the small breakfast nook slowly sipping her tea. She was bundled up in a deep blue cashmere sweater that matched the color of her eyes with flannel pajama bottoms. Her ward for the evening, the Andrews' 8 year old son, Carl, was busy in the adjacent room playing video games, while she was being paid to relax in the comfort of their spacious kitchen, reading magazines, sipping tea and texting.

She sighed to herself at the picturesque scene before her and turned back to the trash mag she was reading. She lackadaisically flipped the pages not really paying attention to any of it. This was the life.

She'd already made enough money to buy the used mustang convertible she had her eye on, so whatever babysitting money she made from here on was just gravy. Maybe she'd go shopping for some new shoes or clothes or something. Not that she had anyone to wear them for.

Although she'd had more than a few interested guys she could have chosen from, Emily was enjoying being single. There was something so exciting about not being tied down to one guy. And though she rarely shut the door on opportunity if it knocked (and if opportunity said the right things, and had a fat cock, she might just have to let it in), she was still happy with the freedom that being single afforded her.

Just then Emily's cell phone buzzed. She looked and saw that her best friend Danie had texted her, 'hey hottie!' Emily laughed.

Emily had met Danie a few months earlier when they'd bumped into eachother, literally. Emily had accidentally rear ended Danie. She'd been pulling out of a spot at the local Starbucks, Danie had been in Emily's blind spot, and fate had slammed the two girls into eachother's lives. Since that moment they'd been inseparable. They saw eachother almost every day.

Emily wasn't generally into girls, but if she had been then Danie would have been at the top of her list. Aside from being wildly sexy, Danie was just plain wild. She was always convincing Emily to do things she would never have even considered. Emily wasn't a prude, but Danie was a wild child. And she was also hot. When the two of them passed a group of guys together, there was enough wood to build a cabin.

'hey what r u up to?' Emily texted back.

'Bored. Free?'

'Stuck bbsitting. Hang this weekend?'

'yup. You gonna take me out on the town?' Danie replied.

'am I gonna get lucky?'

'☺'

Emily sipped her tea and looked out the window again. After flipping through a couple magazines she'd already read, she walked into the living room where Carl was busy shooting zombies.

"Everything alright Carl?" she said over the din of machine gun fire.

"What?" he called out over his shoulder.

"You ok?" she yelled. "Do you need anything?!"

"I'm ok," he mumbled, completely focused on the game.

And just as Emily was going to ask him if he wanted a snack the doorbell rang. At least she thought it was the doorbell. It could have been some sound effect of Zombies getting their heads blown off, but she didn't think that sounded like windchimes. It rang again.

"I'm coming," Emily called out. Walking over to the front door Emily unlocked and opened it and saw two teenagers fiercely making out. The girl was leaning against the doorbell. Turning to see that they were being watched, both quickly stopped and blushed a little and Emily saw that, though she didn't know the girl, the boy was the Andrews' other son Mark.

Emily and Mark had been in highschool together. Well, sort of. He was a couple years below her, and they hadn't really spent anytime around eachother. She'd been the cheerleading captain, prom queen, homecoming queen etc. etc., and Mark had been on the other side of the social spectrum. AV club, chess club, math club. Not that Emily had anything against him for that, she'd just never spent any time in his social circle. Or he in hers.

But she saw that now he wasn't the dweebish nerd he'd been before. He'd filled out a bit and started dressing better. Good, she thought. College seems to have had a good effect on the kid.

"Hi. Um...Hi Emily," he said, still blushing from being caught. "Are my parents home?"

"Nope," she replied, letting the two teenagers past her into the living room. "Just me and the zombie killer."

"Hey squirt," Mark said ruffling Carl's hair.

"Hey," Carl replied, still entranced by his game.

Emily walked over to the cute brunette who had just been plastered to Mark's face. "Hi. I'm Emily. I'm the babysitter."

"I'm not a baby!" Carl called out.

"Hi. I'm Sarah. I'm Mark's...friend."

"Yeah," Mark said, walking over to the two girls, "I needed to drop off some laundry and stuff so I thought I'd show Sarah the house."

"Are you staying here tonight," Emily asked the pair.

"We're...we're not sure," Sarah said, "I mean it kinda depends."

Mark blushed deeper. His cheeks were now nearly crimson.

"Okay, well, you're folks aren't gonna be back until later tonight. Your Dad has a function out of town," Emily said smiling and leaning against the back of the couch. Crossing her arms beneath her she cocked her head at Mark and Sarah and asked, "So. How long have you two been together?"

"We –" they said at the same time. Sarah jumped in first. "We're not really together."

"Yeah," Mark said, "we're just friends."

"With benefits?" Emily laughed.

"No, I mean, well..." Mark replied blushing. "We live across the hall from eachother."

Emily eyed the two of them. Both still awkward from being caught kissing. God they were so innocent looking. Like freshly fallen snow. Was she ever that innocent? She hoped not.

"That's cute," Emily said. An awkward moment of silence passed before she walked back towards the kitchen. "If you need anything, I'll be in here."

Over the next hour or so Emily could hear the two coeds giggling on the staircase, or in the laundry room. To entertain herself she casually and quietly followed them around the house. Just curious. It was either that or listen to Carl playing his games. And it was interesting to think of Mark Andrews as having a girlfriend. A pretty cute one too. Sarah wasn't really hot, but she was definitely cute. Shoulder length brown hair, freckles on her cheeks, cute figure with small perky tits. Mark must be flying high, she thought. She didn't think he'd dated anyone in high school. And then the first week of college...

Not that she was surprised. She could definitely see serious improvement in his looks. But the way he had been kissing Sarah when she'd opened the door was less than ideal. Like watching a zombie devour its meal face first.

Emily walked up the stairs and saw that Mark's bedroom light was on. Stepping lightly so as not to make a sound she walked over to the door and pressed her ear to it. Hearing nothing at first, Emily was just about to abandon her ploy when she heard the sound of lips smacking.

"Mmmm, kiss me slower Mark," Sarah's voice said.

"Slower?" Mark mumbled.

"Yeah, just don't put so much of your tongue in my mouth. It's...not good."

Emily smirked. At least the girl knew what she wanted. And speaking for all women, it definitely wasn't Mark's kissing technique.

"Is that better?" Mark mumbled as Emily heard the bed creak.

"Yeah, just use your lips, and maybe your teeth a little more."

"Like this? –"

"-OW!"

"Oh, I'm sorry, sorry. Shit."

"It's fine Mark," Sarah said, "Just not so much teeth."

"I'm sorry, I'm an idiot," Mark replied and Emily couldn't help smiling at his dejectedness. It had to be difficult especially as a boy and the oldest sibling. I mean, was there anyone to show you the ropes on making out? Emily had been fortunate enough to have been born with an innate sense of what worked in that department, but for a geeky guy like Mark it must be more difficult. He was so gangly and awkward just walking. Kissing, was an art form that took some serious skill to master, and was probably about as easy for him as tightrope walking.

"Here," Emily heard Sarah say, "put your hand here." Emily heard the bed creak a couple more times, the couple apparently rolling around a bit. "Be gentle. They're sensitive."

From downstairs, the sound of zombies dying was blocking out some of the dialogue, but Emily pressed her ear closer to the door and heard Sarah ask, "Can I see it?"

"What?" Mark replied.

What do you think dummy? Emily thought. Your Star Wars collectibles?

"You're..."

"Oh...um...well...ok. You want to?"

A real Casanova. Emily was having a lot of trouble not laughing at this point. She could hear something being removed and Mark shuffling on the bed while, she assumed, Sarah removed his pants. In spite of herself, Emily was getting turned on by the thought of these two kids hooking up while she listened. It wasn't really sexy, but there was something about their inexperience that made it exciting. Like watching a baby deer walk for the first time.

"Wow, it's..." Sarah said.

"What?" Mark replied, his voice betraying the fear that something was wrong with his most intimate parts.

"Pretty big. I mean, I haven't seen that many, but it looks bigger than the other's I've seen."

"Is that good?" Mark asked.

"I guess."

Emily was holding her hand over her mouth at this point to keep herself from laughing. Good for you Mark. You've got a pretty big dick. Now you just have to learn how to use it. He apparently had the right tools, but hadn't read the instruction manual yet.

"Can I touch it?" Sarah asked.

Emily felt like she was listening to an after school special on abstinence.

"Sure...I mean...ok."

Suddenly Emily heard a sound that could only be described as feral. A gurgling, squealing belch and it was only after listening to it for a while that she realized that Mark had been giggling. At least she thought it was Mark. It might have been Sarah. The sound was pretty girly.

"Oh! Did I do something wrong?" Sarah asked.

"No!" Mark said, calming himself down. "I just...it's so stupid, but...I get nervous when a girl touches me and sometimes I start laughing. It's not because you...did anything. I'm just...God, I'm such an idiot."

"No, it's ok," Sarah said. "Should I touch it again?"

"Ok," Mark replied.

And again Emily listened as Mark went into peals of nervous girlish laughter. It went on longer this time. An awful sound. If nails on a chalkboard had a baby with a hyperventilating eight year old girl.

Finally he calmed down, and the room went silent.

"I think...I'm gonna go," Sarah said.

"No! I'm sorry. I just...Please don't go!"

"No, it's not 'cause of you. I... I have some homework I have to do. I'll see you later Mark."

And Emily, who's face was pressed against the door until that point, had just enough time to jump into Carl's room before Mark's door opened up and Sarah walked out. She listened as the front door opened and closed and a car started I the driveway. Then there was silence.

After a few moments she heard Mark let out a loud sigh and mumble something to himself. Backing up into Carl's room she accidentally stumbled and sat on his bed. It creaked loudly, and thinking quickly Emily turned on the light by the bed, reached into Carl's drawer and pulled out some PJ's before Mark peeked his head in. Fully clothed.

"Hi Mark," Emily said, folding Carl's pajamas.

"Uh...hi. Have you...?"

"Yeah?" Emily said turning her big blue eyes on him.

"Did you? Hear anything?"

"Like what?" Emily asked cocking her head.

"Nothing...just. Nothing."

"Everything ok? I heard the front door."

"Yeah, um, Sarah left. She had some...homework," Mark said, a forlorn look in his eyes. Emily's heart was breaking for the kid. He looked so lost. " I'm gonna... Do my homework."

"Ok. I'll be downstairs in a bit."

Poor guy. That's probably going to be one of those memories that just haunts you for years. And it wasn't like his lack of experience was his fault. It was a vicious cycle. He'd never get to learn how to hook up if he didn't get experience, but he wouldn't get experience if he didn't learn how to hook up. Plus that horrible giggling problem. Mark was in for a long adolescence.

After a few minutes had passed Emily walked out of Carl's room and back downstairs. Carl was still shooting things, but she saw that the kitchen light was on, and walking in she saw Mark sitting at the kitchen table with a notebook open. His head was on the table.

He couldn't have looked more miserable if he'd tried.

********************

I'm such a fucking moron Mark thought as his head rested on the table. Maybe I should just forget about women. Become a priest or something. Who the fuck does that? Starts laughing when a girl touches his dick? It was like every time he got close to really hooking up with a girl he would just cockblock himself. It was like his own brain didn't want him to get laid. Still a virgin at eighteen. And it wasn't looking like that was gonna change anytime soon.

He'd lost any chance with Sarah. After that little episode he'd be lucky if she even talked to him again. And she'd probably tell all the girls at school too. Four more years of celibacy. Fuck. This was a fucking nightmare.

"Hi again."

Mark looked up and saw Emily standing at the other end of the table.

God she was incredible. Long, wavy golden blonde hair. Big blue eyes. Perfect tight body and flawless skin. She looked like some kind of Disney cartoon princess. Except Disney cartoons didn't have breasts the size of cantaloupes. On her small frame they seemed almost impossible. He could just imagine how good they felt. Soft, creamy white, heavy orbs of perfection...Jesus. They seemed to taunt him. Every time he looked at Emily Parsons he had to tear his eyes away from her massive chest so he didn't stare.

In high school, she'd been friendly to him, but he was never sure if she ever even knew his name. She was untouchable. A golden princess. His imagination was about as close as he could ever get to Emily Parsons. But he'd be lying if he said he hadn't spent hours and hours imagining doing every conceivable sexual act with her. If he added up all the time he'd spent jerking off while thinking of Emily Parsons and focused it on getting himself better at sex he'd probably have been a modern day Casanova.

And having her witness him crashing and burning after Sarah had abandoned him was just about the worst possible thing he could imagine.

"Hi."

"You ok?" Emily asked as she pulled up a seat and sat down next to him.

"Uh. Yeah...fine," Mark said, attempting a half-hearted smile. "Why?"

Emily put her hand on his. The small gesture immediately caused the horny teenager to get some wood. It was like he had no control over his body.

"No reason. You just seem down." Her hand moved to his arm causing his jeans to become even tighter.

"I'm ok. I just..."

"What?" Emily asked, her hand still lightly touching his arm. "You can talk to me."

"I just...I feel like..."

"Yeah?" Emily said squeezing his arm lightly.

"Nothing. I'm fine."

Emily let go of his arm and reached for the paper in front of him.

"Wait!" Mark said grabbing the paper back.

"Why?" Emily asked. "What is it?"

"Nothing. It's stupid." Mark made an attempt to hide the paper behind his back.

"Come on, I promise I won't say anything bad. What is it?" Emily stood and reached behind Mark's back, leaning over him to grab the paper, one of her breasts pressing against his shoulder. Mark's dick went from 0 to 60 in half a second. His pants were now sporting a huge tent, which he was trying to hide beneath the table while also trying to hide the paper. Unfortunately only one could be saved and as Emily pressed her breast even harder into his arm as she reached behind him, Mark was forced to relinquish the paper.

"Ha! Got it," she said taking a look. "Wow. This is really good. It's Sarah, right?"

"Uh, yeah. I just...it's just a sketch."

"It's really good Mark. Wow. I didn't know you could draw like this."

"It's nothing," he said trying to get it back without having to stand up as his erection was still at full mast.

"No, it's really good," Emily said, looking at the sketch again more closely. "You've got skills."

"It's stupid."

"It's not stupid. It's sexy," Emily said looking at him again with a more serious expression.

Mark couldn't move for a second. His cheeks burned a bright red as the word 'sexy' seemed to reverberate around his brain like a tennis ball. Did she just say he was sexy? Did Emily Parsons think he was sexy? No. She just said his drawing was sexy. Right?

Mark was just about to say something when Carl walked into the kitchen.

"Blood Axe IV is on TV tonight. Can I watch it?" the eight year old said with a look of desperation.

"What's it rated?" his babysitter asked turning her magnificent body away from the still blushing Mark.

"R, but they don't show any of the gross stuff on cable. Please! I promise I'll go to bed right after."

"Would your parents be ok with it?" Emily asked turning back to Mark.

"Uh. Sure. I guess."

"Yay," Carl said jumping up and down. "Blood Axe!"

Twenty minutes later the three of them had gathered in the family's newly built home movie theater in the basement. The room was impressive. Surround sound speakers, HD projection screen, a couch and two lazy boy chairs, both a deep brown leather. It was even sound proofed. Mark's father had built it only the year before so that the family could have "cinema night," as he called it. Mark supposed there were worse ways for his Dad to have a midlife crisis.

The lights had been turned down, the movie had started and the three of them were watching a girl being followed down a darkened street by a faceless killer with an axe. Carl was sitting in the overlarge chair, while Emily and Mark sat on opposite sides of the couch.

Mark was absentmindedly eating popcorn and pretending to watch the movie while he surreptitiously stole glances at the blonde beauty next to him. He couldn't help it. In the dim light she had an almost ethereal glow about her.

Thankfully Mark had placed a blanket over his lap, as he was still sporting a massive hard on. If this kept up he'd probably have blue balls tonight. But had she really said his drawing was sexy? This had transformed from the worst night of his life to the best night with one simple gesture.

"Can I have some?" Emily whispered to him from across the couch. When Mark nodded, offering her the bowl, Emily instead moved closer to him, and reached in the bowl. "Thanks," she said.

The brunette in the movie had found a deserted barn to hide in. She was breathing heavily behind a tractor, her breasts heaving and her panicked eyes darting left to right as she tried to listen for the killer.

Mark couldn't escape. On the TV was a beautiful girl with her breasts almost out and next to him was the girl of his dreams, the plunging neckline of her sweater offering him a fantastic view of the cavernous valley between. Emily was completely focused on the screen as Mark tilted his eyes to get an even better view of her cleavage. Her perfect, glowing skin, creamy and smooth, arched out at her collarbone. The v-neck gave him the most amazing view between her breasts, and if he squinted he could just barely make out the edge of a white bra encasing her huge...

"Mark?"

He looked up to see Emily looking at him with a smirk on her face. Again the teenager went deeply red as he stumbled out an explanation, "I – there was some popcorn – and I didn't know if you saw it – but I –"

Emily grinned at him. And winked. Then she turned back to the movie.