Filled for the First Time : 45 Books Bundle/Box Sets (Medical, Older Man, Menage, Taboo)

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Filled for the First Time : 45 Books Bundle/Box Sets (Medical, Older Man, Menage, Taboo) Page 43

by Sansa Gold


  I knelt to the floor, desperately trying to resemble the pieces together. It was all hopeless, there were too many pieces and many of them were beyond repair. How was I going to cover this up? I couldn't possibly afford to lose this job. My family and I depended on the money I would make from this job. I felt the tears drip down the side of my face. Why was I always such a fuck up? I wiped them away and headed down the hallway to face the quickest release of employment known to man.

  Once I reached the end of the hallway I faced a closed door, I pressed my ear against it. Inside I heard some light music and nothing else to give me a hint at what else awaited me. I knocked on the door as I held the pieces of the broken statue in my hand.

  The music stopped and then I heard his voice, "Come in."

  I pushed on the door until it gave way. I was greeted by a library of books and a large wooden desk in the middle of the room. Richard sat in a large brown chair, his eyes locked on me.

  "Well what do we have here?"

  "I'm sorry." Was all I could muster as I dropped the pieces onto his table. He leaned closer to them and turned them around, examining every piece.

  "Well, this is most unfortunate. That piece was worth at least $20,000."

  My mouth dropped. Had I really damage something that valuable? I knew that I was completely screwed now, I was probably facing more problems than just being let go.

  "You have signed the contract right Vanessa?"

  I nodded my head.

  "Alright, then I'm going to have to give you a punishment."

  "What kind of punishment?" I stuttered back at him, as hand grasped into one of the drawers. Out of it came a wooden paddle, I could see the fine finish on it by the way the light hit it. What exactly did he intend to do with that?

  "Come over here Vanessa. Its time for your punishment."

  I moved around the desk and stood by his chair, waiting for him to tell me what to do. I knew that he could come up with any punishment that he saw fit. I just didn't understand how the paddle fit into all this.

  He pushed back on his chair until it rolled away from the table, "I need you to lay across my knees. You've made a huge mistake and you need to be punished for it."

  "Excuse me?" I asked back, not entirely sure if he was serious.

  "I'm going to spank you Vanessa. Its the only way to make sure you learn your lesson."

  "Your going to spank me? I think not. I never agreed to any of this."

  "Of course you did. You signed the contract after all. The contract stipulates that I can choose any form of punishment that I see fit. This is the form of punishment I give to all my maids."

  I let his words roll through my head, "Yea, I quit if that's the only option."

  "Alright, that's fine." I turned around and walked toward the door, already regretting that I had wasted my morning and all my time with this job. "As long as you can pay me the $20,000 for the damages you incurred."

  I turned around, completely speechless by his words. "What do you mean?"

  "Well, since your not letting me give you your punishment I'm going to need you to pay for the damages, otherwise I'm going to have to go to the police."

  "I-I can't afford that. I took this job to help my family. There is no way we can come up with that kind of money."

  "Well, that's unfortunate but I still need you to pay for it. Otherwise I'm going to have to call the police."

  I stood there weighing the options that were placed before me. There was no way in hell I could afford to pay that twenty thousand, it would take years for me to make that much money. I ran my fingers through my hair, the frustration building up through my body. I was completely and utterly screwed. I walked toward the side of his chair once more.

  "If I take my punishment I don't have to pay you back?" I asked.

  "That's right. You also get to keep your job. But, only as long as you take the whole punishment that I have planned for you."

  I had to do it, not for me but for my family. They were depending on me to help them get through this tough time.

  I sighed and placed my knelt down, "Alright." I whispered.

  I lay my stomach across his massive thighs, trying to get as comfortable as I could. This had to be the most embarrassing event of my whole life. I definitely won't be telling anyone about this. I just wanted it to be over at this rate.

  "You ready Vanessa?"

  I nodded my head, closing my eyes as I readied myself for my punishment.

  I heard the paddle get tossed onto the table, I opened my eyes. I saw as he rolled up his sleeves, taking his time to make sure that they were even on each side.

  "The first part of your punishment will be by hand."

  He raised the back of my skirt, revealing my neon panties to him.

  "Tsk tsk... This isn't part of your protocol at all. Your making this real hard on yourself."

  I didn't argue. There really was no point at this rate.

  The first slap was swift and hard on the left cheek. I slight cry escaped my mouth, the pain was too great. Before I knew it another two fell down on the other cheek and one in the middle. A tear welled up at the side of my eyes. I bit my lip and tried to hold my sounds, I didn't want to give him the satisfaction of this.

  I dropped my head down trying to concentrate on something else as the torrent continued. With each slap I could feel the burn spread up my body. The stinging was growing and growing, just as the tears in my eyes. I had lost count of how many slaps he gave me. There was no way I could keep up. Every time I had tried to start the count, the pain overcame my concentration.

  I turned my head and looked at his face. It was completely concentrated on my bottom as he struck away, his face had long turned red. I dug my face into the side of his stomach, wiping away the tears that had formed. After several more minutes of the pain I began to hear his voice countdown with each slap.

  "Five." Slap "Four." slap "Three." slap "Two." slap "And One." Slap. "Alright, are you ready for the next part of your punishment?"

  I turned my head and cleared my throat, "Yes, Sir." I wanted him to know that I didn't see him as a friend anymore. He was not the same man I had met this morning.

  He grabbed the large paddle off the table, it must have been as large as his arms. I knew that each swat with that monstrosity would completely cover my ass, both cheeks at the same time.

  I pushed my knee hard onto his knees, bracing myself for the first paddle. I felt the air around me move before I felt the paddle hit my bottom. But, when it hit I felt all resistance leave me. I could no longer restraint myself so I cried out. As he rose it back into the air my bottom stung much more than before.

  It felt as if every paddle on my bottom equaled to more than ten slaps. I turned my head and bit into my shoulder, hoping that it would help me get through it all. As the paddle hit my bottom I through my legs into the air, no longer being able to sit still through all the pain.

  "Now, now, Vanessa be a good girl and take your punishment."

  He pushed down on my legs and held them in place, as I felt his other arm going up into the air. I knew this one was going to hurt, I had to pay for insubordination.

  With the next paddle I felt the world around me grow dark on the outside of my vision, I couldn't handle much more of this. Before I could turn around and object the next one paddle burned onto my ass, sending the world around me colliding.

  I no longer felt the pain of his paddling instead I just felt my body floating in the air. A cool breeze hitting against my face, I didn't know where I was going but I didn't mind it at all. It was better than where I was.

  Before, I knew it I was staring at the bottom of Richard's feet, as the air around me moved. The paddle landing once more onto my bottom, I nibbled on my uniform. There was hardly any pain now, instead it was replaced by pleasure. I could feel it build up from the point of pain and stem through my body. I rubbed my legs together and could feel how wet my core was. I was surprised at how much this was turning me on, th
e pain was still there just not as present as before.

  Another paddle hit my ass, I had lost count long ago of these. Who knows how many hit my bottom when I was in my dream world.

  "Yes. Harder." I found myself saying back to him.

  "Are you sure Vanessa?"

  I turned my head, "Yes, Richard please spank me harder."

  A smile spread across his face and he nodded. He brought down the paddle once more, sending a shock through my body. He now began to deliver them in rapid succession, no longer caring about winding them up. I just relaxed my body over his and took my punishment, I was after all a very bad girl.

  After several more swift paddling, he threw onto the table and took his hand off my legs.

  "Are we done, Richard?" I asked in my most disappointed voice.

  "No, you still need to receive your final punishment." I smiled at him, hoping he had another paddle tucked away within the table.

  It was then that I felt his fingers climbing up the side of my thigh, I turned my head around. They rose between my thighs and traced my panties to the seam. His hand gripped onto them and pulled them down, my cunt bare for him to see. His eyes fell on the marks on my bottom, there was severe redding in the middle with hints of purple on the outer edges. His fingers gently pressed down on the bruises.

  "Owww. That hurts." I responded.

  "Good." Was all that he mustered.

  He raised his hand up and struck my bare ass once more, his firm hand grasping my ass at the last second. I could tell that he loved to watch it jiggle with every slap he gave me. I felt his hard cock push up against my stomach, he was completely turned on by this.

  After he got his fill, his hand moved down until a finger found my passage. He pushed into it, curling it against my spot. I grabbed onto his trousers as he began to slowly caress my g spot. The tightness grew in my stomach and my breathing grew more shallow.

  "I know what you were doing in the bathroom. Your such a dirty maid."

  "Mhmm. Keep going. PLEASE."

  The knot in my core restricted, until it could no longer. I felt the orgasm release through my body as it began to writhe in pleasure.

  He picked me up and threw me against the oak table, not giving me any chance to recover. I turned around and saw as he rapidly unbuckled his pants, revealing his enormous cock. It must have been at least nine inches long and five inches around, I had never taken anything that big before. Where exactly was he hiding that thing?

  He pushed it into my pussy, his hands grabbing hold of my ass. My tight cunt grabbed onto his prick, he began to stretch me out harder than anyone ever before. He began to pound me into the table, my moans and his grunts reverberating through the room. I grabbed onto anything that I could to hold down the surge of pleasure within me. I was quickly coming to my next finish.

  Both his hands landed on my ass with quick thumps, in succession. He continued this for several minutes until I felt his body grow more rigid, his pace increasing.

  "I'm going to come now."

  It was then that I realized that he was not wearing any condom.

  "Don't. Your not wearing any protection."

  But, it was too late. I felt his hot jizz hit into me, sending convolutions up my body as I finished with him. I tightened my cunt, hoping to squeeze out every last drop of him. There was nothing we could do about it now, he had already finished inside me without protection. His body fell onto mine, pushing his flaccid cock into me.

  He lowered himself to my ear and whispered, "How was your punishment?"

  All I could do was respond with one simple word, "Deserving."

  Book 24: Step On Taboo

  I laid back in my bed replaying the last couple weeks in my mind, knowing full well that soon I would confess my feelings for him. Every night for the last couple months had been torture. He would come home and I would rush to bed, knowing that it would give him some time alone. After several minutes, I would get out of my bed and sneak to his bedroom door.

  There I would push the door slightly open, listening for his shallow breaths, while porn blasted on his computer. Tom was always bad at locking or closing his door at night, his mistakes lead to my perverted nature. I would watch as he stroked himself to some porn video, the sounds blocking my own moans.

  His body would shake as his arm feverishly moved, trying to bring himself closer to climax. Through the crack I would watch, my hand would already be down below pleasing myself. I would imagine that he stroked his cock with me in his mind. Lately, his choice was incest porn videos, which gave me hope for my circumstances.

  I know that wanting to sleep with your brother would freak out most people, but not me. Nobody else had someone like Tom in their life, he was one of a kind.

  So much of my time lately was spend watching him masturbate. So much in fact, that I began to recognize when he was close to cumming. His body would grow rigid and push back in his chair, a hand frantically grabbing for the tissue box. This would be followed by a grunt that would echo in his room, as he shot his seed. Spying on my brother while he jerked off was the only way that I could get off lately.

  I knew that it was wrong, but the guilty feeling that came with spying on my brother was long lost. Countless sessions of pleasuring myself to him, had assured that. The spying on him was slowly loosing its taboo nature, it had become almost routine for me.

  My fingers would grab my firm tits and work their way down as I imagined him entering me with his cock. There would be times where I tried to mimic his strokes with my fingers, imaging my hand becoming his cock.

  This turned me on more than anything, no man or porn could turn me on like my brother. After watching him play with himself I would run back to the bed, letting my mind replay the scene as I continued to play with my clit until I completely satisfied with myself. I was lucky Tom was still here for me, since he wasn't my real biological brother.

  Both our parents were divorced and met each other while working at a police department. Tom, my step brother, came into my life when I was 13 and he was 16 at the time. When we first met I didn't understand the feelings that began to well deep within me, over the years as I matured I came to the realization that I was sexually attracted to him.

  The next several years would be spent imagining the taboo relationship between the two of us. Then, in high school disaster struck for both of us. Our parents were killed in the line of duty, trying to protect the people of our city. It was then that I hit the lowest point in my life, depression and grief taking over. My feelings for Tom had wavered as I battled through understanding what happened to our parents.

  Nonetheless, it was Tom that stepped up for the both of us, dropping out of college to help us move on. He became both of my parents and nurtured me back to reality, helping me eventually come to terms with their death.

  Unfortunately, this meant that he worked two jobs that he despised just so he could pay the bills. After, I recovered my feelings for Tom resurfaced and I learned how deeply in love with him I was. Now more than anything I wanted to confess those feelings, but I was scared.

  So far I had done little to make him aware of how I felt, instead I used nights to spy on him as he played with himself. For a while this was the way that put my feelings for him to the side, but I had grown tired of it.

  This led to me coming up with a way to confessing my feelings, that have accumulated over the years. There was no way that he would cast me off to the side if he knew how I felt, that wasn't who Tom was. Sure, it could be awkward at first, but I'm hoping I could play it off as being scared of my first semester of college. How I didn't have any experience with any other guy.

  I closed my eyes and smiled to myself, tomorrow would be the day that I told my brother how I felt about him.

  ***

  He would be home any minute now, I sat under his covers re hatching the plan in my head numerous times now. There was no way that it wouldn't work. The only thing that I couldn't account for would be his reaction to seeing me l
ike this, but I hoped for the best. I was tired not telling him and just masturbating in the darkness, I much rather do that with each other. The thoughts skipped across my head, a smile burst out of me. That would be one of the best possible outcome out of all of this.

  I heard the front door open and him wipe his feet onto the old mat outside. It was time to set my plan into action. The moment of truth had finally arrived.

  "Jessica, you here?" He hollered for me.

  I pulled the covers closer to my bare body, hoping that he wouldn't see me when he came into my room. It was a good thing he wasn't a tidy person, otherwise this plan would have never worked. I heard him drop his briefcase onto the floor, his shoes hitting down at the same time.

  "Jess, I'm not in the mood for games. Please come out." He yelled through the house, his voice more quiet than before. He must be searching the house looking for me. I giggled to myself I was probably in the last place he would expect me to be, I hardly ever went into his room. It was something that I had always considered off limits, that trait would help my plan.

  I heard the door slam against the wall and the lights within his room flickered on. I could see his masculine outline through the thin covers, I instinctively licked my lips. I had waited for this moment for far too long. I saw his shadow undo his tie and slowly unbuttoning his shirt, timing my reveal would be crucial for this plan to work.

  I felt his shirt get thrown onto the pile next to me, all the shirts he had yet to give me for the weekly wash. It was then that I heard him plop down onto his chair, this would the time to act anything longer and it might get awkward.

  "Hi, Tom." I said, as the covers dropped and I could him swivel in his chair to face me.

  He jumped out of the chair, pulling his pants up with him, "Holy fuck, Jess you scared the shit out of me. What are you doing in my room?" He frantically buttoned and zipped his pants, hiding his already apparent boner away. I couldn't help but stare at it, knowing that if this night went well that would be all mine.

 

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