Note: This story was dynamically reformatted for online reading convenience. Nanny Dearest Author: YummyTiger Special thanks to my editor! * * * * * * * * * * * Story Codes: Mdom, Fm, Fm+, Reluc, 1st time Story Summary: This is a story about a young boy's efforts to manipulate his live-in summer nanny. This is a longer story so expect the pacing to be slower. * * * * * * * * * * * Chapter 1: The Arrival The taxi cab rolled to a stop in front of a large ornate metal gate. Emily pressed her head against the window straining to see the house beyond. She smiled as her eyes scanned the massive house in the distance. Now this was what she called a summer job. All she had to do was watch a few little brats and in return she would get to spend the whole summer enjoying all that this magnificent house had to offer. "I bet it has its own pool and hot tub!" The thought made her shudder a little with excitement. "Nice layout they got here," the cab driver commented as the gate rolled open. "Better than anything your immigrant ass could afford," she thought although she did not deem the cab driver worthy of an actual verbal response. She instead watched the house grow larger and larger through the window as the vehicle motored up the drive. "What a great summer this is going to be!" Inside the house, three boys huddled around the living room window. Brian, the oldest at 15, stood in the middle and had the best view of the incoming cab. His two brothers, Jacob and Trevor flanked him on each side. Trevor had just turned 13 last week and Jacob was only 7. Both looked up to Brian as their leader, a role he did not want. "Let me see too!" Jacob whined. "Shut up!" Brian replied harshly and Jacob instantly went silent. Brian was thankful that Trevor seemed content to quietly mope. "Whatever," he thought and turned his attention back to the window as the cab rolled to a stop. None of the boys had seen their new live-in nanny yet and when the gate buzzer sounded they had all rushed to the window for their first glimpse. He was hoping that she would not be an old hag like last year. His friend Henry had scored that summer when his parents hired a fairly attractive middle-aged woman. As both of the boys' sex drive had recently kicked in, they spent most of the summer devising ways to sneak peeks at her. To their dismay, they only caught the occasional glimpse down her blouse, but it was definitely better than nothing. Now that a new year had rolled around, both of them were eagerly hoping to score a hot nanny. Brian gasped audibly as the cab door swung open and a beautiful young woman stepped out. She was gorgeous! Her dark brown hair hung in curls around a face most models would envy. Inevitably, his eyes took a downwards course and found two lovely mounds waiting. Her breasts were bigger than Henry's nanny's last year! The fabric around shirt's buttons strained as if in danger of bursting open at any moment. Oh, what he wouldn't give to see those babies! The woman turned towards the driver to retrieve her luggage and Brian received his first view of her backside. Her jeans molded lovingly to the contours of her ass, forming a wonderful peach shape. It was an ass that demanded to be grabbed and squeezed. Brian was still gawking when she turned back and started towards the front door. He was so mesmerized; he did not even hear Jacob's renewed whining. "What a great summer this is going to be," he thought. Emily could barely restrain herself from running into the house as she stepped from the cab. She wanted to see the inside so badly. What was the pool like? Was there a hot tub? A theatre room? A house this luxurious had to be brimming with phenomenal amenities and she could not wait to see them all. She was ingrained in her thoughts that she was oblivious to the boys staring at her through the front window. "The fare has already been covered, Ma'am," the driver said, remaining before her expectantly. "Thank you," Emily replied. "Hah, a tip? I have a tip for you; take a damn shower once in awhile!" Emily thought, laughing to herself. She turned haughtily, ignoring the harrumph behind her and made her way towards the front door. Before she could even knock, the door swung open and three boys stood huddled inside. "Wow, they are older than I thought they would be," she thought. "Hello. Is Mr. or Mrs. Whitman here?" she asked formally. On of the older boys looked about to say something, when the youngest one interjected, "Are you our new nanny?" "Yes, my name is Emily," she answered curtly. "May I come in?" The older boy quickly pushed ahead of the other two. "Uhm... yeah, come in." Emily stepped into an immaculate foyer. Spotless wood floors ran into a large two story main room. Two staircases spiraled around the walls, leading to a second floor. Expensive looking pictures and paintings adorned every wall. Dollar signs flashed through her mind and she could not even fathom how much money must be in this room alone. The extravagance only made her more anxious to see the rest of the house. "Well, are your parents around?" She asked, turning her attention back to the boys. She noticed the oldest one's eyes were focused well below her face, but quickly shot up when she turned to him. "Great... I will have to watch this one," she realized. "Yeah, one sec. MOM! THE NANNY IS HERE!" the oldest boy shouted towards the back of the house. Emily heard a muffled response and again noticed the boy's eyes slide towards her chest. She set her luggage down, making sure to keep her back straight so that her blouse did not fall open. An older woman entered the entryway a moment later. The woman had long black hair flecked with a hint of gray. Emily could tell that she had been quite attractive once and still looked good for her age. Emily tensed up slightly as the lady strode purposely across the floor and stopped behind the three boys. "You three better not be causing this lady any trouble," she said jokingly to the children. "Hello, you must be Emily. It is nice to finally meet you, I am Mrs. Whitman." Emily's tension eased as the woman seemed to be friendlier than her demeanor had initially portrayed. "Pleased to meet you Mrs. Whitman." "I see you have already met the boys, although I am sure they neglected to introduce themselves. This is Brian, my eldest," she said tapping his head. "This here is Trevor and the little one is Jacob." Jacob beamed proudly as she said his name. Mrs. Whitman then turned to Emily with an appraising look. "You are younger than I thought. Most of the nannies the agency sends are in their forties or fifties." "Yeah, I just started last month. I'm the youngest at the agency." "Ah, I see. Are you in college?" "Yes ma'am, I'm starting my third year over at the Harlington." "Great. A college education is one of the keys to success. I am always glad to see a woman taking the initiative to get ahead." Emily noticed Mrs. Whitman's eyes widen slightly as they fell on her suitcase. "Oh mercy, my apologies. I should let you get settled in. Brian, would you help Emily carry her luggage up to the guest room?" "Yeah, sure," he replied, looking away from her chest for the first time during the exchange. "Ugh, what a little pervert," she thought. "After you settle into your room, I am sure the boys would love to give you a tour of the house, wouldn't you boys?" she said in a voice that was less a question and more an order. All three boys quickly responded that they would. "I will be in the kitchen. Dinner should be ready in about an hour and I would love for you to join us Emily, if you haven't eaten yet." "It would be my pleasure." "Great, we can talk more then." Mrs. Whitman smiled once more before heading back towards the kitchen. Emily watched her leave then turned to the boys. Brian already had her suitcase in hand. "Uhm... the guest room is this way," he said pointing to the stairs. He turned and started up the stairs, with the younger boys in tow. Aside from Brian ogling her, at least they seemed well mannered. Hopefully they would not require much of her attention this summer. She did not want to have to spend the whole summer constantly looking after three stupid kids. Visions of boobs bounced through Brian's head as he led Emily up the stairs. The new nanny looked even better up close! He had never met anyone so beautiful; she looked better than most movie stars! While he had tried not to stare, his eyes uncontrollably kept dropping to her amazing chest. He loved the way her blouse adhered to every curve and how her breasts bounced slightly as she moved. He had hoped for a little peek when she set her suitcase down, but she had not bent over far enough for him to see anything. No matter, the whole summer lay ahead. The house had two guest rooms, but his mother had not mentioned which one he was supposed to lead her to, so he chose the one right next to his own room. "The closer the better," he thought. He remembered all those cheap B movies in which they would drill a hole in the wall to peep at the girls next door. "Who knows, maybe it really would work!" He passed his brother's rooms and then his own. The guest room was the last room on the left. The room was fairly plain by the house's standards, adorned with 2 dressers, a vanity and a king sized bed. A few rustic paintings complimented the light green walls. "Thank you," Emily said as he set her luggage down. Jacob immediately started jabbering and Trevor slinked into the background. "Ms. Emily, I am so happy you're our nanny!" Jacob gushed. "Thank you Jacob, I am too and as long as you behave, I think we will have a lot of fun this summer." "Oh, I always behave Ms. Emily! I won the student of the month four times last year!" Brian rolled his eyes in disgust and thought, "I won the student of the month, blah, blah." "That is wonderful." Brian butted in, "Would you like to start your tour now Emily?" Emily was about to open her mouth to comment on Brian addressing her by her first name, but then thought twice. This would be a long summer if the boys constantly had to call her by her surname of Draisen. "That would be great. Give me a moment to get settled in and I will meet you back in the foyer." Emily noticed all three faces drop slightly at her request for them to leave, but they did as they were told and slowly filed out of the room. "Good to see that they are disciplined," she thought, "even if the little one doesn't shut up and the older one stares at me like a rapist." Emily plopped her suitcase on the bed and snapped it open while her mind wandered. She was new to this whole nanny thing, but two of her girlfriends were nannies and raved about how easy it was. She didn't really like children, they were messy and a lot of work, but her friends had insisted that she try it out. "It's easy money," they maintained, so she had joined the agency. When she read about this opportunity on the job postings board, she had made sure to flirt with the manager. Men were so easy to control, all it took was one date and she received the assignment. That idiot had actually thought she was interested in him. Emily had not hesitated to flaunt her good fortune while basking in her friends' envy. Her mouth turned upwards into a smile just thinking about it. Her friends had ended up in run down shacks while she got this mansion. "Better to be beautiful than smart I guess," she gloated as she unpacked the clothes she did not want to wrinkle. It was not long before half the contents of her suitcase were hanging in the closet. She took a moment to really examine the room she would call home for the next few months. The guest room was one of the nicer bedrooms she had slept in and that was saying something since she only dated men with money. The bedspread caressed her skin as she ran her hand along it. It was so soft that she almost purred. "Oh, there is nothing like comfortable sheets!" The country portraits and light green paint created a nice, soothing atmosphere. Two dressers stood against one of the walls and a huge vanity with a mirror dominated another. She examined her reflection in the mirror and made a few minor adjustments to her hair and shirt. "Looking amazing as always," she thought while flinging her hair into place. Deciding that the boys had waited long enough, she left the room to meet them downstairs. "Ms. Emily, Ms. Emily, you have to see my room first!" Jacob exclaimed the moment she entered the foyer. "Puleese!" "Who cares about your room? I want to see the pool," she thought but instead put on her best fake smile and responded, "All right, we can stop at your room first." Jacob started to jump around with joy. Emily noticed Brian give Jacob a look filled with loathing. Trevor meanwhile remained in the background drawing circles on the floor with his foot. She had seen his type many times; a typical nerd who was probably picked on relentlessly in school. At least she doubted he would be much trouble, nerds were usually the easiest to manipulate. Brian, on the other hand, she would have to be cautious of. His eyes were already roaming her body once more. "You wish," she thought with disgust. "Well, shall we start the tour Jacob, err, I mean Mr. Tour Guide?" she said. Jacob's face lit up like a light bulb at the title and he immediately assumed a businesslike posture. He motioned for her to follow and began marching up the stairs. Jacob's demeanor cracked immediately when he entered the first room in the hallway. The room was practically overflowing with toys and Emily was not exactly flabbergasted to hear Jacob exclaim, "This is my room!" "Wow, you have a nice room Jacob. That sure is a lot of toys," she said, feigning interest. "You wanna play? You wanna play?" Even though she could think of a million other things she would rather do than play with kids toys, she kindly replied, "Not right now, but I will later. You still have a tour to give?" Jacob's attention immediately shifted back to the subject at hand. He resumed his formal attitude and continued the tour. Emily followed Jacob and the other two boys from room to room of the gigantic house. Jacob's enthusiasm never wavered and he nearly burst at every stop. The house was even better than she had hoped. It had a huge pool in the backyard, a tennis court, a trampoline, which Jacob excitedly showed her how to use, and a large grassy area to play games in. There was even a hot tub and sauna inside a screened-in patio right off the pool area. All of that would have been awesome enough, but Emily's tour of the basement provided a nice bonus. The basement had a billiards room and decked out theatre room complete with tiered seating. The best part was that every aspect of this house was laden with top-of-the-line equipment. Emily concluded that if Heaven existed, this was it. After the tour, she was even more excited for the Whitman's to leave and the summer to begin. This house was the epitome of luxury; and she was getting paid to live in it! Brian trailed behind Emily throughout the tour, staring at the sway of her ass. His imagination ran rampant as he tried to imagine her without clothes. Aside from his daydreaming, the tour itself was pretty boring; he did get his hopes up for a moment when Jacob tried to get Emily to jump on the trampoline with him. That would have been a sight to see. Brian would definitely have to try and get her on it this summer. He made a few attempts during the tour to initiate a conversation with her but they were always cut short by Jacob's frequent outbursts. He did learn a few things, however. She had just turned 20 in February and was doing this to pay for school. He also learned that this was her first job as a nanny. He was excited to learn this as he figured her lack of experience might work in his favor at some point this summer. He just needed to figure out how to use it to his advantage. He was still dwelling on possibilities when Jacob led the group towards their final destination in the tour, the kitchen. "Perfect timing, dinner should be ready in a few minutes," Mrs. Whitman said when they entered. "I was just about to see if I could find you guys. Brian and Trevor, would you please set the table. Emily, would you be a dear and take Jacob to the bathroom to wash his hands?" "Of course Mrs. Whitman," Emily replied and quickly shooed Jacob towards the nearest restroom. Brian watched her go, envious that Jacob was getting to spend more time with her. "Earth to Brian, help your brother set the table." His mother's admonishment startled him and he hastily went about setting the table with Trevor. "So what do you think of the new nanny?" Brian asked Trevor as they were setting the table. "She seems nice." "Nice? She is hot!" "Uhm... yeah, I guess." Brian rolled his eyes. "He is so worthless," he thought, "What the hell is wrong with him?" Trevor had no friends and seemed content to hide in the background; a stark contrast to Brian. Sometimes Brian felt bad for him and would stick up for him, but it seemed a lost cause. Oh well, if he was not going to enjoy the nanny then it was his loss. "Hey Mom, is Dad eating here tonight?" Brian inquired. "Not tonight, he's finishing up a few things at the office before we leave tomorrow," his mother replied while scooping food onto serving plates. Brian never understood why they did all the cooking and cleaning. Most of his friends had maids who did these things for them. The one time he had asked his mother about it, she had launched into a tirade about the importance of learning to take care of themselves and how maids were a waste of money. It still annoyed him, but he had learned to just avoid the house when she was cleaning. Emily and Jacob returned to the kitchen as he was finishing up. Brian ate his food in silence while Emily and his mother discussed what was expected of her this summer. He listened for anything that he could use to his advantage, but they mostly discussed emergency contacts, grocery delivery schedules and cooking. Boring, boring and boring! He finished his food before anyone else and politely asked to be excused. "Clean your plate before you leave," was all his mother said before turning back to Emily. Brian wasted no time after dinner heading to Henry's house. He peddled furiously down the street and up Henry's driveway, which was no short distance. Dropping his bike to the ground, he dashed around the house and through the back door. Brian was practically a member of the family and usually just let himself in. Henry was in the games room playing a video game. "Hey, what's up?" Henry asked when Brian entered. "You would not believe how lucky I got!" Brian responded excitedly. "Your nanny?" Henry asked eagerly. "Hell yeah, dude, wait till you see her, she is freaking hot!" "Thank God. Mine showed up today and she is a wrinkly old hag." Henry replied dejectedly. "I was afraid we both might get shafted." "Looks like you'll be spending a lot more time at my house this summer and trust me, it'll be worth it. I plan on getting more than a few glimpses down her shirt this time around." "You got any ideas?" Henry asked as his eyes lit up at the prospect. "Nothing yet, but I did find out this is her first nanny job and she doesn't seem very intelligent. We'll just need to figure out how to use it to our benefit." "Well, at least we have plenty of time," Henry replied. He grabbed the second controller and held it out to Brian. They played a few games, but Brian's mind was elsewhere and Henry devastated him. After an hour or so, Brian decided that he should get home. Since his parents were leaving tomorrow morning, they would probably want him to be there tonight. He said good-bye to Henry and raced back home. Emily excused herself after supper, telling Mrs. Whitman she had to finish unpacking. Actually she was almost done unpacking, but she wanted to take a break from Mrs. Whitman and the kids. She grabbed one of her celebrity magazines and lay onto the bed to read a bit. She had not gotten very far when there was a knock on her door. "Ugh, who is it now. Can't I have a little peace and quiet?" she thought. "Come in." The door opened and Jacob stood in the doorway dressed in his pajamas. "Ms. Emily, my mom wanted me to ask you if you would like to join us in the family room." "Not really," she thought but replied, "Sure, I'll be down in a few minutes." Jacob flashed a grin before skipped back off down the hall. Emily set her magazine down and slid off the bed. "Alright Emily, put on your happy face, you only have to deal with these people for one night." Emily stopped in front of the mirror to check herself and when she was content, made her way downstairs. She entered the family room to find Mrs. Whitman sitting on the couch with Trevor and Jacob. Mr. Whitman was sitting in a recliner chair sipping what looked like liquor. He immediately stood up when she entered and strode across the room to meet her. "Nice to meet you Emily," he greeted her and reached out to shake her hand. "Nice to meet you Mr. Whitman," she said as she shook his hand, "And thank you for allowing me to baby-sit for you this summer." "Now, now, call me Robert. Please have a seat and join us. Can I get you anything to drink?" "Water will be fine," Emily replied while taking a seat on the empty sofa. "Hello Emily," Mrs. Whitman said as Mr. Whitman made his way into the kitchen. "Glad you could join us, we were just about to watch a movie." "Sounds great," she said doing her best to sound enthusiastic. Mr. Whitman returned with her water as Mrs. Whitman put a DVD into the player. A couple of animated characters bounded onto the screen as Jacob squealed in delight. "This was going to be a long night. At least the couch is comfortable," she thought. She wiggled a bit to find her comfort zone and did her best to watch the movie. Brian showed up a few minutes after the movie started and of course had to sit right next to her. Emily was thankful when the movie finally ended and was able to escape back to her room. She read her magazine some more before drifting off to sleep while thinking about how awesome this summer was going to be. One room over, Brian was busily typing instant messages to Henry on his computer. All he could recall from the movie earlier was the intoxicating scent coming from Emily. He had spent the whole movie stealing glances in her direction and had been sad to see the movie end. Now he was working with Henry on ideas, but up to this point the well had remained dry. Brian was not overly concerned though since the summer was just beginning. He had an inkling that tomorrow would bring opportunity and after a yawn decided it was time to sign off. He said good-bye to Henry and plopped onto the bed. He drifted off to sleep thinking about how awesome this summer was going to be.