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 2: The Lost Boy Emily was wide awake well before the alarm clock sounded. Her excitement defeated any chance of falling back to sleep and after a few minutes she gave in and hopped out of bed. She made her way down to the kitchen to find Mr. and Mrs. Whitman sitting at the table talking over coffee. "Good morning," they said in unison. "Good morning," Emily replied. Emily noticed Mr. Whitman's eyes stray from her face and blushed slightly in realization that she was still in her pajamas. It was a bad habit from living in an all girl's college dormitory and one she would have to break; especially considering the way Brian had stared at her yesterday. "There are some fresh rolls on the counter and plenty of coffee in the maker. Please help yourself," Mrs. Whitman said, apparently not fazed by Emily's apparel. Emily thanked Mrs. Whitman and made her way over to the food. The rolls consisted of a variety of muffins and croissants that practically fell apart in her hand. "Yummy," she thought to herself and filled a plate before sitting down opposite Mr. and Mrs. Whitman. They proceeded to make small talk about their upcoming trip and Emily was relieved when Jacob came screeching into the kitchen as she had just about exhausted conversational topics. "Good morning Miss Emily." "Good morning Jacob," she replied smiling. He ran up and before she could react gave her a big hug. She reddened for the second time when Jacob pressed up against the thin material of her pajamas. "Well, we had better get a move on if we want to get to the airport in time," Mrs. Whitman announced and stood up from the table. Emily released Jacob and helped Mrs. Whitman with the dishes before walking with them to the door. Brian and Trevor already stood at the front door bleary eyed. Mr. Whitman must have woken them up so they could say good-bye. Emily watched as everyone hugged each other and said their goodbyes. They shook Emily's hand one last time and wished her well before grabbing their luggage and heading to the waiting limousine. Emily closed the door and turned to the kids. Her summer was finally about to begin. After his dad woke him up, Brian stumbled downstairs and stood next to Trevor in a zombie-like state. Brian silently cursed his parents. They always did this. They would leave early in the morning and force him to wake up to say good-bye. Why couldn't they just wait until noon to leave like normal people? What he did not realize was that getting up this early would have its perks. He watched his parents enter the foyer with Emily and Jacob behind them. His eyes immediately shot to Emily, still in her pajamas and obviously not wearing a bra. He was enthralled with the sway of her unconfined breasts under the thin material. Sleep was now the furthest thing from his mind. His gaze barely left the nanny while he said his good-byes. "Well it looks like summer has begun," Emily said after closing the door. "Brian and Trevor, there are some rolls in the kitchen if you're hungry. I am going to get dressed; can you keep an eye on your brother?" Brian barely heard a word she said, but murmured, "Okay." He was far more interested in her thinly-covered body and was crestfallen when she turned to leave. "I may have to start getting up earlier," Brian thought. Jacob bolted from the room the second Emily left his eyesight. Brian figured he was probably going out back to the trampoline or something. He contemplated heading upstairs and back to bed, but his stomach overrode that idea and sent him towards the kitchen instead. He would check and see if Henry was awake afterwards. There was work to do. Emily pulled the t-shirt down over her bathing suit, relieved to be covered. She would not make the mistake of going downstairs in her pajamas again. Just thinking about it made her blush. She was thankful that she had brought her one-piece swimsuit. After seeing Brian's reaction to her nightwear, she doubted her bikinis would be getting much use this summer. Anyway, enough dwelling on this morning, it was time to start enjoying the perks of this new job. She grabbed her towel and practically skipped to the pool. Along the way, she stopped in the kitchen to check on the boys. Brian was busily cramming a roll in his mouth, but his eyes lit up when she entered. He grunted a hello with his mouth full. "Disgusting," she said to herself before asking, "Where are Jacob and Trevor?" Brian swallowed the bite and answered. "Um, Trevor went back to bed and Jacob ran out back." "Alright, thanks for keeping an eye on him. I am going to take a dip in the pool, please let me know if you leave." "Ok. I might have a friend over in a few hours." Emily told him that that would be fine and was relieved to hear it. Hopefully that would keep him busy and out of her hair. She was beginning to think that he might end up posing the biggest problems of all the boys and was still thinking about it when she reached the pool. She admonished herself. Here she was worrying about some horny, little brat when she should be enjoying this wonderful day. She pushed the concerns from her mind, removed her t-shirt and lay down on one of the patio chairs to get a little sun. "Ah, now this is more like it!" she thought as the warm rays of the sun washed over her. Emily woke up a while later. She had no idea how long she had slept and immediately checked her watch. "10:48! Holy shit!" she thought, unable to believe she had slept so long. The sun felt amazing and she noticed that her already tan skin had darkened further. She laughed at the thought that she was getting paid to tan. Her friends would be so jealous. She stood up and stretched away some of her grogginess. "I better check on the boys," she thought. Without even thinking to put her t-shirt back on, she made her way around the pool and into the backyard playground area. There was no sign of Jacob or the other boys. A tinge of worry crept into Emily's mind when she found the other areas of the backyard empty as well. "Calm down, they are probably just inside the house," she told herself, but her pace quickened nonetheless. She made her way back into the house to find the kitchen empty aside from a few dirty plates on the table. She made a mental note to discuss chores with the boys. The family room, entryway and living room were also empty. She figured that Jacob must be in his room and headed upstairs. When she found Jacob's room empty her concern really started to take hold. "Damn stupid kids, can't they watch themselves for an hour or two?" she thought as her eyes started to water. She took a few deep breathes to try and calm herself. "He has to be here somewhere," she decided. She rushed to Trevor's room and felt some of relief to find Trevor sleeping soundly in his bed. "Well, that's one down. The others must be downstairs," she concluded, her confidence coming back. Brian nearly crapped himself when Emily crashed through the theatre room door. The movie had already made him uneasy and the last thing he was expecting was someone to burst into the room. "Have you seen Jacob?" Emily blurted out. He stood there confused from her sudden appearance and anxious tone. His bewilderment slowly faded into realization. "Did she lose him?" he questioned silently. Brian figured his brother was probably at his "secret fort" down by the creek, but since Emily was new she had no idea the secret fort. He realized that she actually thought that Jacob was lost and was about to tell her not to worry when something in his mind clicked. Here she was, standing before him in her swimsuit, afraid that she had just made a monumental mistake. Perhaps he should play along a bit and see what happens. "Uh, no, I haven't seen him. Did you check his room?" Brian asked. "Of course I checked his room. I checked the whole damn house!" Emily snapped back, "When was the last time you saw him? Do you know where he might be?" He was taken aback by her tone and slew of questions. Brian was beginning to see just how worried Emily really was and the magnitude of situation dawned on him. "This may be just the opportunity I need," he thought evilly as a plan began to take form. "I've been down here watching a movie, so I haven't seen him since this morning," he replied. Her face dropped dejectedly and he could only imagine what must be going through her mind. It was time to put his plan to the test. "I can help you look for him, but you have to do something for me," he said. Emily did not immediately comprehend what Brian said and even after she did, she decided she must not have heard him correctly. "What did you just say?" "I said, I can help you out, but you have to do something for me," he repeated, this time much slower and emphasizing the "do something for me". She definitely did not like the smug look on his face. How dare he attempt to use this situation to manipulate her! This little shit thinks he can make demands now? She would put an end to this insubordination right now. "Now you listen to me. You WILL help me find your brother or I WILL call your parents," she declared angrily. "There... that should put an end that nonsense," she thought. "Be my guest and while you're on the phone you can tell them how you lost Jacob in the first place. It's not my job to watch him," the boy commented mockingly. Emily could not believe her ears. He had the gumption to arguing with her. Well, she was not about to be bullied! She would definitely deal with him after she found Jacob. "Fine, if you won't help me, I will go get Trevor and you can bet your parents will hear about this little episode." She stormed from the room in a rage. How dare he make demands of her? She was in charge! While, she figured he simply wanted to get out of doing chores or his curfew, it was the principle of the whole thing. She was not about to be bullied by a fifteen year old; especially one whom she was babysitting. Unfortunately, one thought persistently kept coming back to her. Brian had a point. The Whitmans would not be happy if they found out she lost Jacob only two hours on the job. She was caught in a minefield and did not know which way to turn. On one hand, if Brian told his parents about this episode they might fire her, but on the other, if she did not punish Brian for his disobedience, she would be setting a dangerous precedent. To top it off, she still had no clue where Jacob was! The fact that Brian started up the stairs right behind her only served to make everything worse. "Good luck with Trevor, he is about as much help as a rock. Hell, he rarely even leaves his room. You would probably have to describe what "the outside" is to him," Brian told her. Emily remained silent as Brian laughed at his own joke. She was afraid of what she might say if she opened her mouth. Unfortunately, her silence did little to shut him up and his taunts continued. "Wow, lost Jacob on the first day. That can't look good. Didn't you say that you just started at the agency and this was your first assignment? Hmm, I bet they would be interested to know what kind of nanny they are employing." She had reached the stairs to the second floor when she erupted. "Listen up, you little shit! If you will not help me, then stay quiet. In fact, you are grounded to your room until I say otherwise! Go to your room now!" she commanded. The boy simply stood there smiling at her and her anger started to give way to fear. She was losing control. She never lost control. What should she do? Think Emily, think, she pleaded to herself. The only thing she could come up with to bring Brian back in line would be to call his parents, but how could she do that without admitting she'd lost Jacob. Running out of options, she tried to bluff. "I don't think you heard me. I said go to your room now, or else!" she commanded a second time and stamped her foot for added emphasis. "Or else what?" Brian replied smugly. Shit! Now she was really worried. He had called her bluff, which left her with only two options. She could either ignore Brian's defiance, which would admit her unwillingness to call his parents and seriously weaken her authority; or, call his parents and probably lose her job as a result. She wanted to both scream and cry at the same time and she could hardly believe it when she heard herself utter, "What do you want?" She watched in disgust as Brian's smile widened in response to her admitted defeat. His eyes shifted from her face to her chest and she became acutely aware that she was only wearing a bathing suit. The words, "What do you want?" were music to Brian's ears. His plan was working! He knew she was bluffing when she threatened him. How could she? She was the one who'd screwed up. Basking in his victory, he focused on the two plump mounds sitting just beneath her swimsuit. He knew exactly what he wanted. He wanted to see those wonderful titties. He mustered his courage and prayed that he was correct in assuming Emily could not afford to call his parents. "If you show me your breasts, I will help you find Jacob." Emily stood before him with a shocked look on her face. He watched her mouth open and close a few times as though about to speak, but silence was all he heard. He stood there doing his best to maintain a confident persona, when in truth his blood was rushing a mile a minute. The fact that she had not immediately rushed to the phone was a good sign and bolstered his assertion that she would not call his parents. After what seemed an eternity, Emily finally spoke. "Brian," she said in an outwardly calm voice, "You know I cannot do something like that. First of all, it is against the law and secondly, I am your nanny... perhaps we can come to some other arrangement." Brian chuckled to himself. She wished it would be that easy. He would be a fool to let this opportunity slip away. Emily had seriously screwed up and had no idea where Jacob was. She could not call his parents due to the consequences and her inexperience only compounded the situation. No, he would not settle for anything less than her exposure. Emboldened by his reasoning, he stood his ground. "I believe the deal is you have to do something I want, and really, all I want is to see your breasts. I'll make it simple. Either you show me your breasts or I call my parents right now and tell them you lost Jacob." The firmness in the boy's voice filled Emily with fury. Nobody made ultimatums to her! How dare this little piece of shit stand here and threaten her. She wanted to slap him until he cried, but she didn't; she couldn't. She knew that physically assaulting him would only make things worse. Inside her head two voices bickered back and forth. One voice argued to just call his parents and deal with the consequences, while the other reminded her of what she would be giving up. She would be losing thousands of dollars and this wonderful house. Not only did she need the money for next semester's tuition, but she had no other living arrangements setup. She was still weighing the pros and cons when Brian turned from her and walked over to the phone. He picked it up and turned back to her. "So what's it going to be? Should I call my parents?" In the moment of truth, her greedy nature won out. She was not willing to part with her luxurious summer house and all the money that came with it. She was going to give in to a God damn fifteen year old! How the hell did she let this happen? The phone emitted a little beep as the boy pressed the first digit. Her dream job was turning into a nightmare; another beep. Fuck! Just get this over with. "Alright, put the phone down. I'll do it," she said, shocked at how steady her voice remained. Brian was about to press the final digit of the imaginary phone number when he heard what Emily said. He was so astonished to hear her words that he stood there, his finger still on the button. "Well? Are you going to put the phone down?" Emily asked him, her voice trembling slightly this time. Brian recovered from his initial shock and what she had just said sank in. Holy shit! It worked! It really worked! He dropped the phone and gawked at her soon-to-be exposed bosom. "Well, let's go to my room and get this over with," Emily said with resignation. Brian just nodded his head, afraid that any minute he would wake up and this would all just be a dream. He still could not believe that she was really going to go through with it! He watched Emily turn and start up the stairs without another word. Brian bounded up the stairs right behind her, his heart beating so fast it threatened to burst from his chest. His eyes remained locked on her luscious body all the way to her room and one word kept repeating in his mind: "Awesome." It was all Emily could do to not scream in frustration. Was she really about to do this? What choice did she have? She could not afford to have Brian tell his parents what had happened. It will just be a quick flash. She tried to convince herself that it was just a minor thing. Yet, she walked down the hall like a death row inmate walking to their doom, each step requiring more and more effort. How had this happened? She could still turn back. She reached the doorway to the guest room and paused as her doubts crept back in. Deep down she knew this was a mistake, but again her greed forced her doubt from her mind and she stepped into her bedroom. She closed the door after Brian entered and turned to find the boy sitting on her bed staring at her in anticipation. Dread crept through her body; she needed to get this over with before she lost her nerve. Emily positioned herself in front of the boy and reached up to the two shoulder straps of her bathing suit, her hands trembled slightly betraying her nervousness. She felt her cheeks redden and she slowly slid each strap from her shoulders, not to be erotic, but to delay the inevitable as long as possible. She then pulled her arms free and the swimsuit straps fell to each side which left her swimsuit clinging dangerously to her breasts. She gripped the top of the suit and braced herself for what would come next. Brian sat widemouthed while Emily stripped out of her swimsuit straps, his pecker rigid against his pants. It was happening! She was about to show him her breasts! He watched her fingers delicately slide under the swimsuit's top and hesitate. "Do it!" He mentally ordered and then it happened. Emily's hands shot downwards and her swimsuit followed. Her breasts popped out of the suit and two pinkish nipples appeared briefly before the suit was quickly pulled back into place. After it happened all he could think was, "What the fuck! All this and he had barely seen anything!" "There! I did what you wanted, now you hold up your end of the bargain and help me find Jacob," Emily demanded as she slid her right arm back under the suit's strap. "What was that? I did not see anything!" Brian blurted out. "You need to show me longer than that if you want my help." "Now you wait a God damn second! I did exactly what you requested. I am not about to stand around topless for your amusement," Emily replied outraged. "Well you are going to have to show me longer than that!" How could she think that he would be satisfied with that skimpy show? Hell, he had barely gotten to see anything. Aggravation replaced Brian's earlier lust and he sat before Emily determined. Emily remained silent as well and like two gunslingers they stared at each other waiting for the other to act. While stoic on the outside, Brian's mind kept repeating, "Come on and just give in." Emily cracked first and rolled her eyes in exasperation before finally saying, "Fine, one more time and this time I will count to ten, but this is the last time!" Judging from the hostility in her voice, Brian decided it would be dangerous to press it further. Ten seconds was shorter than he wished, but it would have to do. "Agreed," he replied. He noticed Emily's hands did not tremble this time when she slid the straps back off her shoulders. None of her previous hesitation was present and she immediately yanked the suit downwards. Emily's tits bounced free for the second time and Brian barely heard her begin to count as he stared at the two firm orbs before him. Her uncovered breasts contrasted with the darker skin around them, forming an erotic outline of where the suit normally lay. The pink areolas that had so briefly appeared earlier now stood bare for his enjoyment and her nipples thrust out proudly. His eyes devoured the scene as he burned the image of those stunning breasts into his mind. If he were to live until 100, he knew he would never forget this moment. "... 8... 9... 10." He watched longingly as Emily pulled her swimsuit back up and covered her amazing bosom. Wow! Before now, he had only seen pictures of naked women from the Internet. The real thing was so much better. He continued to stare as Emily slid her arms back through the arm holes and adjusted her suit back into place. Two lumps in her suit signified that her nipples had not softened yet. "There, you got what you wanted. Now help me find Jacob," she said in a voice dripping with contempt. He knew it was time to uphold his end of the bargain. His penis was still rock hard and the sooner he got Jacob back, the sooner he could take a moment to seek relief. Anyway, the summer was just beginning and he'd gotten Emily to show him her breasts within the first few hours. Something told him that this was going to be a great summer!