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Strangers in my Bed

Strangers in my Bed

Literotica

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Anna Walton hasn't had an easy life, but that all changes when she applies to be the caretaker for Jack Weston. The last member of a wealthy family with a rare mental illness. Each day Jack believes he is a different person, but one thing remains constant: his lust for Anna. His loyal caretaker, she fulfills his every need, but after each night she's left wondering: will she ever really know this stranger in her bed?

Chapter 1 Mr. Weston

I fell in love with him when he was Jack. I don't even know if he ever really was Jack, or if "Jack" was just another one of them. The doctors say his condition is rare. Therapy might help, but there's no guarantee he would ever fully recover.I only knew a few things to be absolutely true about Jack.

He was the last living member of an old and incredibly wealthy family called "Weston," he lived all alone in a humongous mansion hidden in the forests of Canada, he had an incredibly rare mental illness that made him believe he was a different person nearly every day, and I was hopelessly in love with him.I met him by accident. I was twenty-six, broke, and on the verge of being homeless. I wasn't close with my family but did keep close ties with one friend from my hometown: Sara. She was one of the few people I felt comfortable enough to confide in.When I explained my problems she offered a solution. Her great uncle was retiring from his job as a caretaker soon. A lot of people had applied, but few made it past the first three days of the week-long training, and none past the sixth. Apparently, he was getting desperate and asked her to search around. Well, begged might have been a better word than asked.I asked her what the job entailed. She said I would be required to live in a giant, luxurious mansion in the middle of 500 acres of Canadian wilderness, completely rent-free. I would be paid eight hundred dollars daily for my services, meals and other expenses related to my work would be complimentary. My sole responsibility was to care for a mentally ill man. He was neither dangerous nor abusive, but his changing moods and various demands were something many people had trouble adapting to.I'd always been an adaptable person. I asked her how to contact her uncle. My initial interview took place over the phone. General questions about my health, experience, etc. I was honest about having absolutely no experience in this area, it surprised me when he actually asked when I'd be willing to start.By that next week, I was flown in a private jet to an out-of-the-way airport in a small Canadian city. Sara's uncle picked me up and drove me to what would potentially be my new home. In a limousine of all things. As we drove, the buildings and houses of the town slowly began to thin out. Before I knew it, there was nothing but the forest surrounding us. The trees blurred together into a wall of green as we drove past them. I was beginning to wonder if they would ever end. Suddenly, I saw a dark silhouette rising above the tree line. The mansion.I stared in awe as we approached it. As we drew closer he stopped the car and got out to open the large front gate. The walls surrounding the place were huge and made of stone, the gate was a solid, but intricately decorated slab of iron. The gate was impressive, but it paled in comparison to what was on the other side. Acres of green grass spread in every direction. Shrubs, trees, and flower patches were dotted throughout. It was so large I couldn't even see the other walls that were supposed to surround the place. A breathtaking view, but I barely noticed it as the actual mansion came into view.It was a beautiful old mansion styled in the Victorian fashion, but was so well cared for you would have thought it was brand new. More beautiful stonework made up the outer walls, large columns helped to support the sloping roof. I almost couldn't believe the size of them. Gothic windows dotted the outside, though most were covered by heavy curtains. A pair of heavy, wooden doors guarded the entrance of the home. It was like something out of a classic romance novel.The interior was just as gorgeous, but I had little time to admire it. No sooner had we stepped inside than the caretaker turned to me. He looked serious."There are certain things you must know if you are to care for Mr. Weston," he started. "The first is that he has no family. He is the last of his bloodline and, therefore, you should immediately reject any 'family' that comes asking for financial help.

The next is that his condition is a mental illness and incredibly rare. He believes he is a different person each day. You are to play along with whatever fantasy his mind has created, and, above all, keep him safe. That being said I, of course, will not ask you to put yourself in harm's way and there is an emergency phone if you require assistance from the police or the hospital. However, I wouldn't worry about it. In my twenty years of caring for Mr. Weston, I have only needed to do so twice.Finally, you must realize you are, in fact, a full-time caretaker. You have no holidays, no days off, no "free time" to travel around the cities. Except in the case of a 'family-emergency,' Mr. Weston will be your first, last, and only priority." He stared at me a moment upon saying this. After a few seconds, a smile crept across his face. "Now, on that note, he's also a very gentle and kind person. I think you will come to truly care for him after a short time if you see past his illness.We begin your training tomorrow Ms. Walton, so feel free to explore and familiarize yourself with the mansion. If we are both lucky, it will be your new home very shortly."I took a moment to take in the load of information he'd just given me. He waited expectantly. I perked up and nodded in understanding. He smiled and nodded in return before walking off somewhere into the mansion. I was completely alone. It felt somewhat intimidating being in that big house by myself. I wondered if I'd ever get used to it. He told me to explore, so I did.I must have seen dozens of rooms: bedrooms, ballrooms, libraries, galleries, and this was still only half the mansion. All to take care of some poor, sick old man? I wondered about this "Mr. Weston." How bad was his condition? Not only did he practically live alone, but it was also nearly impossible to find a caretaker for him. Exactly what had I gotten myself into?I was thinking over this when I wandered outside and into the garden. The sun was just starting to set and a field of roses became illuminated in its soft glow. Their scent filled the air. Any worries I had moments ago vanished from my mind completely. The scene was so perfect I could hardly believe I was there."Beautiful," I said breathlessly."Funny, I was thinking the same."I jumped at the unexpected sound of another voice. A well-dressed man was sitting on a stone bench in the garden. He looked about my age, maybe a little older. He was pretty attractive. Normally, I wouldn't mind a guy like this appearing out of nowhere, but why was he here? The words of the caretaker flashed through my head."Sir, I'm sorry but this is private property. You can't be here," I said, trying to sound professional.The man looked shocked. After a moment, a smile spread across his face."If it's private, may I ask what you are doing here Miss... Miss..." He paused a moment, waiting for me to introduce myself."Walton. Anna Walton. I'm here training to be Mr. Weston's new caretaker. Now, could you please tell me what you are doing here Mister..."He laughed. "Weston! Jack Weston and I had no idea that old fart would ever hire such a lovely young woman to care for me."I couldn't begin to hide the shock on my face. To be fair, no one had ever said that Mr. Weston was an old man, but I'd assumed he was. Living alone with no relatives and only an old caretaker just seemed to fit the image of an old man more.Mr. Weston was far from what I imagined. He was young but more than that he was quite handsome. His light brown skin shone in the light of the sunset, wisps of his short black hair fell across his eyes, and his voice was deep and soothing.

He smiled at me and I suddenly realized I had been staring, mouth agape, for far too long. I turned away, blush rising to my cheeks."Let me guess, you assumed I was some dirty old man?" He said, smirking. "Why does everyone assume that? Is it something about my name?"He seemed to be lost in thought at this."Honestly, Mr. Weston," I said, still refusing to look at him, "I think it's the position they're applying for. Caretakers aren't a common occurrence among young men."He turned back to me and stared silently for a moment. Panic ran through me. Had I said too much? Had I offended him? I had nowhere to go if this job didn't work out. Was I going to be fired before I even started?He stood and moved toward me. I was hoping he'd be kind enough to let me off with a warning. I looked at the ground awaiting anything he might have to say about my behavior. Instead, I felt his hand gently lift my chin until my eyes met his. I wanted to look away but feared offending him."Tell me, Ms. Walton," he said gently, "how will you care for me?"The tone of his voice made a shiver run through my body. I suddenly lost all power to speak. Time seemed to freeze. The over-exaggerated sound of someone clearing their throat broke through the moment. We turned to see his caretaker standing there."I see you've met Ms. Walton, sir," he said, simply."Thomas, I wish you told me sooner we would have a young lady staying with us," Mr. Weston grumbled. "I would have made better accommodations."I blushed. "That's really not necessary Mr. Weston. I'm only here to work, really."Perhaps it was my imagination, but I could have sworn he looked a bit disappointed when I said this."Well, work or not, please choose any room in the house as your own," he said, vaguely gesturing towards the large mansion. "They're all empty or will be as soon as Thomas retires. It would make me happy if you would begin to think of Weston Manor as your home, Ms. Walton."I merely nodded and walked back into the house. As soon as I was out of sight I thought I heard muffled arguing. I was curious if I was the cause, but I wasn't going to ask. I knew better than to rock the boat before I even had the job.As he suggested, I looked around the house for a room I liked. It was a difficult decision. The rooms were all grand and gorgeous, I could hardly decide between them. However, on the third floor, at the very end of the hall, I entered a room that was breathtaking, to say the least.The floors were black marble polished until they shone. The walls were high and covered in a dark red wallpaper in a Victorian pattern. A large stone fireplace was nestled between two giant bookcases taking up the entire west wall. The east wall was sixty percent occupied by a large window nook and the rest by a large set of double doors. But the most noticeable feature was the huge canopy bed in the center of the back wall.The frame was made of some kind of dark wood, an intricate design was carved into the posts and headboard. The curtains surrounding it were heavy, black velvet. Red silk sheets and a down comforter covered the bed. In the fading light, a large iron chandelier made itself known from the middle of the room. It was perfect.I sat on the bed, barely believing I could really be in a place like this. I felt the softness of the comforter beneath my hands. I suddenly became aware of how sleepy this whole day had made me. Seeing as my training started tomorrow, I didn't think old Thomas would mind if I took a short nap. I would move my things later. With that decided, I laid across the bed and quickly fell asleep.

I don't know how much time had passed by the time I woke up, but I could tell it was already dark. I heard a gentle crackling and the scent of smoke was faintly noticeable. Thomas must have lit a fire for me, how kind of him.I suddenly felt a gentle tugging at my hair. Did it get caught on a part of the bed? I moved my hand to untangle it, but instead felt warm flesh against my own.The shock quickly woke me. I gasped and sat up looking around in a blind panic."Sorry, did I wake you?" Mr. Weston's voice spoke from the dark.Was I dreaming? I rubbed my eyes hoping they would adjust. I wasn't. Slowly, his silhouette became clear."Mr. Weston! What are you doing in my bed?!" I cried, shocked.He laughed. "Funny, I was thinking the same thing, Ms. Walton. To clarify you are actually in my bed.""What?!""Amazing really," he said teasingly, "there must be over fifty rooms in this house and somehow you choose the only one actually occupied. I compliment you on your taste though."As the delirium from my sudden waking left I slowly began to understand what he was saying. I jumped out of the bed and hoped the firelight wasn't bright enough to show my blush."Mr. Weston, I'm so sorry. I-I had no idea, please forgive me," I stammered.How was I already screwing up so much on my first day? I hoped he would be understanding. I really needed this job."It's really alright Ms. Walton," he said, shrugging. "I don't mind at all. You know, I was actually discussing with Thomas the other day that I thought I needed something for my room, but I wasn't sure what. You've helped me realize what it was."I tried to answer with what little dignity I had left. "And what's that, Mr. Weston?"I heard his footsteps moving closer to me. I nearly died of shock when he put his hand on my waist. With the other, he gently moved my hair behind my ear."A beautiful woman to share my bed," he said in a low voice.Panic set in. I couldn't breathe. I couldn't move. It wasn't as if I'd normally be opposed to such an offer, but sleeping with my boss? My severely mentally ill boss? The first day of my training? It was too much. I gathered together what was left of my jumbled nerves to try to salvage the situation."I'm very sorry for the mix-up, Mr. Weston. I'll find a new room and move my things there immediately," I said, avoiding eye contact."That's really not-""I have to go!" I blurted out.I didn't run from him, but it was certainly much faster than a walk. I walked around the dimly lit hallway until I found the staircase. I had left my things by the door when I first got here, but now they were gone. Did Thomas find out what happened? Was he just waiting for me to take me back to the airport?"Is everything okay, Ms. Walton?" A voice asked.My heart nearly leaped out of my chest. I was getting really tired of being startled every few minutes. I turned. Thomas was there with an old lantern."I-I was just looking for my things so I could move them to my room," I sputtered finally."I've already moved your things to Mr. Weston's room," he said casually. "Everything's been taken care of."I went a bit numb. "But Thomas-""Your one and only duty is to care for Mr. Weston. Part of this submitting to his every whim," he said pointedly.

"You can't honestly expect me to-""As I have said before," he interrupted, "I will not expect you to put yourself in any harm. However, merely sharing a room with Mr. Weston will do no such thing. Even at his most unbalanced he knows better than to force you into anything... undesired.""This-this is too much," I said, shaking my head. "I'm not some plaything, I-""You are if you want this job, Ms. Walton," he said sternly, "and from what my niece has told me you need it."All I could do was stand there silently. He wasn't wrong, I did need this job. If I left now I'd be homeless. Even if I did find somewhere to stay I had no way of making money. Especially not money this good. Still, sleeping with my boss to get it? Desperate or not, I wasn't sure I could do it.Thomas sighed and began walking up the steps. "Ms. Walton, the care of Mr. Weston is unlike anything you would have ever experienced. Some of the best-trained caretakers on this Earth have been driven away due to his erratic behavior. I have cared for this boy since he was ten years old. He's like a son to me, but I'm tired... Ms. Walton, I'm so very tired."Perhaps it was the lamplight or the tone of his voice, but when he turned to look at me it really did seem that the man had never had a moment's rest."I did this as a favor for my niece, but also because I'm quite desperate, Ms.Walton. I need to know someone will be here to take care of him when I am gone. So, please, if I have to beg I will. Do as Mr. Weston asks," he pleaded. "Draw boundaries when needed, but if it does you no harm, please do as he asks."I felt bad for old Thomas. Twenty years following requests most servants would probably run from, twenty years separated from friends and family, twenty years raising a child that wasn't his own, and now being trapped in that situation because it seemed nobody could handle it but him.We stood in silence for what seemed like forever. After a moment I crossed my arms and looked at him seriously."I can set boundaries?" I asked cautiously."Of course, Ms. Walton," he said, smiling. "You are a servant, not a slave. I've let Mr. Weston have nearly everything he's ever desired in this world, but I've never let him think he is more than just a man. We all have limitations, even him."He tried to say these words with confidence, but I could hear the overwhelming relief in his voice. He really wanted me to stay. I wondered how desperate he must be to have gotten to this point. I wasn't trained, I had no clue what I was doing. I wasn't really worth fighting to keep around, but he fought anyway. I can't imagine how many applicants must have flat-out refused to stay, how many times he must have begged them for one more day.He gestured vaguely upstairs. I nodded and began to follow him. He took me back up to the room. He knocked briskly on the door."Come in, Thomas."The voice that spoke just now was so hollow I could hardly believe it was the lighthearted Mr. Weston I'd met today. Was he very upset with me? Perhaps Thomas had begged me to stay for nothing. As we entered he had his back to us, staring into the fireplace."She left, didn't she?" He said simply, shrugging."Mr. Weston-""Don't bother, Thomas. I already know," he said, letting out a deep sigh. "What's wrong with me, Thomas? Those others you brought didn't matter. I couldn't care one way or another if they stayed, but there was something about her. I liked her."We both stayed silent. I thought Mr. Weston had been toying with me earlier, seeing what he could get away with. Was he actually acting that way because he liked me? I felt a small twinge of guilt that I'd shrugged him off so easily. Maybe he didn't exactly act appropriately, but how much experience could he really have talking with people?

He was practically alone out here, and Thomas was used to him by now. Plus, all these caretakes going in and out. It must be hard for him to connect with others. Even harder if they ran off. Like I did. I should have tried better to understand him, I should have tried harder. After all, did I expect this job to be easy?"I think I spoke to her wrong. I told her I wanted a beautiful woman to share my bed," he mumbled, running his hand through his hair. "I wasn't lying, but perhaps I should have said it better. Is there even a good way to say that, Thomas?"Thomas stayed silent for a moment. "None that I can think of, sir.""I didn't think so."He went over to one of the armchairs and sat down. He stared into the fire. Its crackle was the only sound filling the growing silence. Mr. Weston let out a deep sigh."I really liked her, Thomas," he said sadly. "Can you call her back? Offer her more money? I have more than enough. Promise her I'll behave better. I will. I absolutely will."Thomas turned and looked at me with desperate eyes. I swallowed the lump in my throat and walked toward the fireplace. I stopped just behind him."Thomas, do you think I can ever get 'better'?" He asked.I cleared my throat. "There's really nothing wrong with you, Mr. Weston. You just need to realize female servants will have more boundaries.""Anna?!" He gasped.He turned around in shock. We both started at the use of my first name. He cleared his throat and looked away awkwardly."Ms. Walton, I thought you'd left," he mumbled."I thought about it, Mr. Weston, but I think I'd like to try being your caretaker for a while," I said, smiling.A smile spread across his face too. "Thank you. I'll have your things moved to a proper room immediately.""That's alright, Mr. Weston," I said, waving off the offer. "If you wish for me to stay here I'd be more than happy to.""Is-is that really alright, Ms. Walton?" He asked cautiously.I nodded. "Of course, sir. After all, it is my job to serve you."My nerves were still shaking with every word, but the smile that filled his face helped calm them a bit. He stood and took my hands in his."Thomas," he said without taking his eyes from me, "you can go now. Ms. Walton and I will go to bed for the night.""Of course, sir," Thomas said simply.He bowed, shooting me one last desperate glance before closing the door. It was just the two of us now. The crackle of the fire filled the silence again. I could see in his eyes he wanted to speak to me, but he held back. I'm sure he feared that the wrong words would make me run off again. I spoke first."Where can I change, Mr. Weston?" I asked.I saw a flash of something in his eyes, but it happened too quickly for me to identify it. I waited for him to answer. He stayed silent. It felt a little awkward. I bit my lip and looked down."Please speak to me, sir," I begged. "I'm sorry if I behaved rudely before, but I was just a little shocked. I'm sure I'll get more accustomed to you as time goes on. So please, speak freely to me as your caretaker.""Your behavior was fine, I was in the wrong earlier. I just don't want to upset you," he said cautiously."I promise if I am, I will simply tell you," I assured him.

He hesitated. "Well, if you're sure it's alright. I do have one request.""Of course, Mr. Weston.," I said cheerfully. "What can I do for you?"He let go of my hands and walked to the set of double doors near the window. He opened them to reveal a large walk-in closet. He looked around for a while before returning with something in hand. It was too dark for me to see what he had."If you really don't mind submitting to my requests, Ms. Walton, then I request that you wear this to bed tonight," he said with a mischievous smile. "It is yours after all."He handed the item to me. Dread filled me as I felt it unfold in my hands. Why had I even packed this for a caretaker job? It was black satin lingerie. The edges of the bust and skirt were trimmed with black lace. It was almost skin tight and incredibly short on me."Is there a problem?" He asked.Thomas' desperate plea echoed in my head. Do as he says, but set boundaries. I could do this."No problem, sir," I said confidently, "but I will change in the closet."He smiled. "Of course, Ms. Walton."I securely closed the doors behind me and did my best to change in the dark. It was okay. He wouldn't do anything to hurt me. I just had to suck it up and do what he asked. As much as I thought this, I still couldn't help the knot forming in my stomach. It only grew larger as I felt the smooth material hugging my bare skin.I exited the closet, but he was nowhere to be seen. I noticed the curtains were closed around the bed now. I walked over and pulled them back. He smiled up at me from the bed."It really does suit your figure," he commented.I felt myself blush deeply, but this had almost nothing to do with the compliment. It seems he had changed for bed as well. The difference was he was wearing nothing but a pair of black boxer shorts. I turned away and looked at the floor."Sorry, I've gotten used to sleeping in my underwear," he said. "Is that alright?"His tone was half-teasing but I could hear a hint of real concern in his voice. I walked around to the other side of the bed, keeping myself as far away from him as possible."It's fine, sir. This is your room and I am here at your request. If there will be nothing else, then I wish you goodnight," I said quickly.I closed my eyes and pretended to sleep. I could feel his eyes on me for a while before I finally heard the soft and even sound of him breathing deeply. He was asleep.This day was exhausting. I just took a nap a few hours ago and already felt tired again. Everything about this job was very strange, but I suppose there was nothing bad about it. I had a beautiful home, a well-paying job, and an "interesting" companion to say the least. I suppose there were worse jobs than having to share a bed with a handsome man. I smiled at this thought. It helped me relax enough to finally sleep.I wasn't sure what was happening in my dream, but it was nice. I was in this hazy place, but couldn't focus on my surroundings. All I could focus on was the burning heat between my legs and the pleasure it sent through my body. I heard my name being called by a raspy voice.Anna. Anna!The voice half-woke me. I realized I wasn't in some hazy dream world anymore. Slowly, my mind remembered where I was. I was back in the canopy bed in Mr. Weston's room. However, the pleasure between my legs was still there and getting stronger. I felt something hard pressing against my thigh."Anna. Anna!"This time I recognized the voice. It was Mr. Weston. The shock completely woke me. Blush filled my cheeks as I realized what was happening. He was still sleeping deeply, so deeply he wasn't aware that he was touching my body.The heat between my legs was from his hand that had slid under the skirt of my lingerie and begun to rub me. And the hard thing against my thigh? Well, it wasn't too hard to figure that out. He called out to me again."Anna. Anna!" He cried longingly.The sound of his lust-filled voice didn't help to relieve the heat between my legs. If he was doing these things unconsciously in his sleep, then what was he doing in his dreams? His other hand slid over and cupped my breast over the lacy material. I let out a stifled gasp.What should I do? Should I wake him? He wasn't doing anything intentionally, but what was I supposed to do? I didn't really have a chance to decide.The hand on my breast slipped below the lingerie and made contact with my skin. His hand felt so hot against me. As his fingers rubbed against my nipple I could feel myself becoming more aroused.This was wrong. I should stop him. I tried turning around to shake him, but all this did was press his hardness further into my thigh. He let out a low moan and began pawing more furiously between my legs. I gasped, the sensation was becoming too much. If I couldn't wake him I'd just get out of bed.I tried to sit up but he was holding me down too firmly. Fine. I'd crawl to the edge of the bed then. I slowly tried to spread my body across the bed and pull myself to the edge. However, as I did this his body reacted and tried again to pull me closer. His strong arms pulled me forcefully back to him and in the process, his fingers slipped below my panties."Anna," he moaned.The desperate sound of my name on his lips made me shudder. His fingers began to explore the new region they had discovered. I blushed at the embarrassment of the situation, but more so at how I was reacting to it.As his fingers explored my lower lips I could hear the sounds of its wetness. The shame and pleasure were such a strange combination. I couldn't help but wish for more. He was happy to help. His fingers brushed against my clit and a desperate moan escaped my lips. He responded. His fingers began moving quicker as if they were begging to hear me again. I pressed a pillow to my face and bit it as the pathetic whimpers refused to stay in my mouth.He tried harder. I could hear the sweet wet sounds his fingers made as they moved against me. I didn't realize I'd begun to rock my hips against his hand until his body started to match my movements. His hips moved in time with mine pressing his hardness into me more and more. By this time pleasure had overtaken my reason. I longed for his hardness to press into me, to fill me, to stop the ache of emptiness I felt deep inside.He began to press against me more furiously. I heard ragged breaths escape his lips as he called out to me."Anna! Oh, Anna!" His voice was desperate.The warmth between my legs grew and he rubbed my clit greedily, begging for more. I felt the heat building inside me like I would explode at any moment. I felt his hardness move from my thigh to my panties. As he thrust quickly against me I could just feel the tip pressing my lips, teasing them. It was too much.The heat that had been building inside me suddenly burst through my body. It clouded my vision and melted the ice on my tongue."Jack. Jack!" I gasped as my orgasm overtook me.The waves of pleasure made me buck my hips furiously. As my wild movements pressed his hardness further into my panties I heard his moans grow. A moment later he held me tightly to him, I couldn't move. He pressed himself against me one more time before crying out in ecstasy."Oh, Anna!" He moaned loudly.After a moment he loosened his grip and his fingers slid from my panties. Only the ragged sound of our breathing remained. A short while later his breathing steadied and became deep and peaceful again. I turned and looked at him. He was sleeping peacefully, a faint smile on his lips.As the rest of the heat faded from my loins I let out a small sigh. Maybe this job wouldn't be so bad after all.

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