Training Little Abby (A Dark Age Play Romance) (My Little World Book 5)

by Becca Little

  “Discipline me? What do you mean?” I felt a little panic in my stomach.

  “I will not hesitate to put you over my knee for a spanking, or across the edge of that table.” He pointed to the dining room. “For a session with the cane...”

  “Wait, you’re going to spank me…and cane me!?” My panic turned into a thunderous thumping in my throat and ears as my blood pressure elevated. “You can’t be serious!”

  “I am very serious, Abby. You are receiving a very generous gift from me and until you graduate, I will be your guardian.” He lifted the cigar to his lips and took another plume of smoke into his mouth.

  “I don’t need a guardian! I’m an adult!” I squeaked my words out through my panic.

  “I think the fact I had to bail you out of jail completely contradicts both of those statements.” The smoke rolled out of his lips as he took another drink of his liquor. The glass was almost empty and he quickly refilled it.

  “That’s ridiculous. What are you trying to do, turn me into a child? Wait, is that what you’re trying to do?” Things started to click into place. Everything from the clothes to the guardianship and the mention of punishment seemed to indicate just that.

  “Is that such a bad thing, Abby? You’ve basically failed at being an adult, so maybe you do need to spend some time as my Little Abby so you can properly grow into the young woman your mother and father expected you to become.” His tone had no hint of sarcasm and he wasn’t laughing.

  Everything quickly became crystal clear. My mother had basically turned me over to a man she expected to become a new Daddy to me—a replacement for the father I never really had because he was taken away at such a young age.

  “I’m not sure about this.” I shook my head as confusion filled my head. “Can I sleep on it?”

  “Certainly… If you decide you want to leave, the door is not locked.” He stood up and took his leave, disappearing into one of the other rooms.

  Chapter 6

  I walked up the stairs, feeling the railing as my hands drifted across it. It felt so incredibly fancy. When I got back to my room, I started searching for a pair of pajamas. I found what amounted to a large sack with buttons in the back designed to easily go to the bathroom without completely undressing oneself. It seemed like something fitting of the decor, upgraded to modern times. I walked over and stared at the paintings of the Revolutionary War. The one of George Washington crossing the Delaware River was one I remembered from my textbooks.

  “Okay.” I looked over at the bed. “Time to sleep on this whole silly ordeal.”

  I crawled into the large, lavish bed and slid underneath the quilts. It felt amazing and my whole body sank into it, forming a perfect outline around me. The pillow felt like a cloud, pulled down from the sky and molded around my weary head. Most nights I would lay awake and think about things before I went to sleep, but the minute my head hit the pillow, I was enraptured by it. It felt like the bed was sucking my soul out of me. Before long, I was fast asleep.

  ***

  “Ah, Ms. Abigail.” A hooked arm extended towards me.

  “Huh?” I looked around the room in confusion.

  I blinked a couple of times. I was vaguely aware I was in a dream as I tried to focus on my surroundings, but it was vivid and almost surreal. There were people around me that I didn’t recognize and many that had faces of people I knew growing up. All of them were dressed in suits and gowns of the Victorian era. The man that had extended his arm was Mr. Addison’s butler, although he seemed to be in a much different role as he offered to escort me down a large marble staircase.

  “The Revolutionary War was a dark mark on our country, but nobody will be talking about the bloody Americans when we conquer Asia.” A hearty laugh sounded from my right and I looked over to see Jeremy’s face on a man dressed like a British soldier.

  I looked down at my feet as I walked and saw that I was dressed in a beautiful Victorian dress. It was even more lavish than the ones in the closet. The butler turned escort walked me across a dance floor where people in Victorian times were doing modern dances. I wanted to pull away and walk towards them, but my arm was firmly attached to my escort and I couldn’t pull away. Eventually, we walked to an old library where there were dusty books, large tables, and a man facing away from me.

  “Mr. Addison.” My escort released me from his grasp. “I have brought Ms. Abigail for you.”

  “Wonderful.” The man turned and it was Mr. Addison, with a glass of liquor in his hand.

  There was something different about him in my dream. He appeared happier and he looked at me with eyes I was certain were undressing me. Just looking at him made me tingle inside and I could feel my pussy getting wet underneath my large, lavish dress. He placed his glass on a table and crossed the distance between us, taking my hand in his. He lifted it to his lips and stared into my eyes.

  “Are you ready to begin?” His voice was haunting, like it spoke directly to my soul.

  “Begin what?” I got lost in his gaze.

  “Your education of course, Ms. Abigail.” He turned and walked me to a table where several books were laid out, along with a paper and an ink quill.

  My days started moving in fast forward, almost like a montage. I spent days in that library, studying and learning all of the subjects he piled on top of me. Mr. Addison walked around with a long rattan cane in his hand, slamming it down on the table if I didn’t do what he asked. Over time, I found myself getting more attracted to him, longing for the sessions with the books while he watched over me.

  There were nights I attended balls, designed for popular women of the era. I was always part of the scenery and nobody ever asked me to dance. Occasionally, a man would look my way, but as he approached, he would always be interested in the girl next to or behind me. It was a terrible letdown, even in my dream. The dream accelerated with more lavish balls, more studying, and more potential partners choosing someone else over me. As the height of my frustration grew, I didn’t even bother to look up when someone approached.

  “Ms. Abigail. May I have this dance?” I heard a voice say. I looked up to see Mr. Addison standing in front of me.

  “Why certainly.” My turned from concern to a smile.

  We danced the night away—literally. By the time we were done, the sun was coming up and the rest of the people at the ball were either passed out or headed towards their horses. Mr. Addison took me by the hand and walked me towards the library. Despite being awake for at least twenty-four hours in my dream, I wasn’t tired at all. When we entered the library, Mr. Addison turned me around and pressed his lips to mine.

  “I want you so bad, Ms. Abigail.” His lips briefly parted from mine and he let out a sigh.

  “Mr. Addison…” I muttered. “I’m a virgin.”

  “Not for long.” He lifted me up and took me to a table, dropping me on it and sliding between my legs.

  “We shouldn’t do this.” I felt a sense of wrong, but it felt so right when he started kissing my neck.

  He moved from the layers of my dress easily and before I knew it, I was naked underneath the dress and his cock was hard against his pants. He reached down and unfastened them, letting his cock fall free from the fabric prison. I felt scared and apprehensive when it was pressed against my pussy. He slid me forward and entered my pussy with a thrust, easily sliding past my hymen. In my head, I knew it was supposed to hurt, but I didn’t feel anything was pleasure. It felt just like real life, although my mind still knew it wasn’t reality.

  “Mr. Addison…” My words turned into a drawn-out whisper. “That feels really good.”

  His cock penetrated me deep, and I could feel his body against mine, the heat of our embrace amplifying the experience. What I didn’t know about sex, my mind filled in the blanks with random sensations of pleasure. I had explored my pussy on my own with my finger, but I was always timid when I felt my hymen. Mr. Addison shattered it and started thrusting, unwilling to walk away unsatisfied. My hi
ps moved against him, feeling the same sense of lust from within that his engorged cock was indicating he had.

  “Ms. Abigail.” His words formed an echo in my head. “You’re so beautiful.”

  He started to pound my pussy as my hands moved across his large frame. He was almost like a giant from the stories I read as a child, so much larger than my five-foot four-inch frame. His cock felt enormous. I looked down to try and see what his cock looked like as it fucked me, but my dress was clocking the view. All I could do was lay back against his arms and succumb to the pleasure. My brain was in overdrive as it tried to rationalize what I was feeling and the sensations of his cock.

  “You’re being very good to me, Ms. Abigail.” His teeth gritted. “You’re going to make me cum.”

  I was way ahead of him. As his cock started to throb inside of me, I started to orgasm. It felt like it was centered in my clitoris, despite the fact he was deep inside my pussy. I focused on each thrust, feeling myself getting closer every time he drove himself in deep. He let out a roar and I knew he was ejaculating inside of me. My hips started to move faster and I felt spasms in the wall of my vaginal cavity. I clenched on his cock and felt myself milking the last drop out of it as he slumped against the table.

  “Time to wake up…” He whispered into my ear.

  My eyes flew awake and I sat up in a panic mouthing my displeasure. I pushed the covers off me and I found that I was soaked from head to toe in sweat. I slid out of bed and I saw a wet spot where I had been laying—exactly where my pussy was. I slid my hand into my pajamas and found that while I was dreaming, my orgasm was very real. I pulled my hand back and stared at the result. I was completely filthy with sweat, and my pussy was soaked with my imaginary dream-fueled lust.

  The thoughts of what Mr. Addison said I real life started to appear and I really needed to think about it since I was wide awake. I decided the best place to think would be that wonderful tub—especially since I was so filthy, so I stripped off my clothes and climbed into the warm water again after the tub was filled. After I calmed down a little bit, I stifled a laugh at the thought of Mr. Addison making love to me. He was younger than my father, but he was still older than me, and although he was quite attractive, I had never really found myself attracted to someone his age. Besides, he had threatened to spank me!

  I found myself once again enjoying the pleasure of the sprayer, rubbing my clitoris while it stimulated all the nerve endings in my vagina. I had orgasmed in my sleep, and the result was on my bed, but I was still turned on. My mind betrayed me and right when I was at the point of no return, the faceless muscle-bound hunk who was taking my virginity stared into my eyes with Mr. Addison’s steel colored orbs. I tried to shake it out of my head, but I was already in the middle of my orgasm and I got the full mental image of Mr. Addison fucking me as hard as he could, just like he did in my dream, before I was done.

  “Well that won’t make things awkward at all…” I said to myself with a disgusted sigh and leaned back against the edge of the tub.

  Since I was awake and in the afterglow of a very pleasurable experience, even if it had a strange ending, I finally let my mind clear and consider the situation. What Mr. Addison was offering was strange, but incredibly tempting. There was no way I could deny what he had said. My life wasn’t great, and even though I tried to gloss over it, with a little soul searching, I couldn’t help but admit he was right. Mr. Addison was extremely wealthy, and there were people who would kill to get such an offer from him.

  I could truly make something of myself if I took advantage of his generosity. My mother wouldn’t have sent me to live with him unless she did trust him, so that had to count for something. It would be that hard to go to college, study, and do a few chores around his massive house. After that, I was practically living in the lap of luxury. Would America have embraced British rule if it came with mansions for all and free education—maybe? I decided that I was going to accept his offer. I would let him take on a role as my guardian, and I would let him spend all the money on me he wanted. It would almost be like living as the daughter of a Lord or something.

  Chapter 7

  “Mr. Addison?” I walked downstairs and looked around what appeared to be an empty house.

  “Good morning, Ms. Abby.” A voice startled me from behind. It was the butler from the night before—I smiled when I thought about his role in my dream.

  “I was looking for Mr. Addison.” My eyes scanned the room I was in and the adjacent rooms.

  “I’m afraid he has already gone to work for the day. He should be home this evening. He left some paperwork in the living room for you to review, and if you have any questions, I can answer them for you.” He folded his hands in front of him. “Would you like some breakfast?”

  “No thank you, I’ve never really been one for breakfast.” I gave him a warm smile. “Hey, what is your name anyway?”

  “My name is Walter, Ms. Abby, although I’ll answer to pretty much anything.” He motioned towards the living room, so I walked in and took a seat. There were multiple stacks of paperwork on the table.

  “All of this?” I asked.

  “Yes ma’am. Please read them carefully and let me know if you have any questions at all.” He stood stoically nearby as I thumbed through them.

  “These look pretty complicated. I think I need a law degree to even get through the first page…” I sighed as I tried to figure out the meaning of several confusing words.

  “Well as luck would have it, I do have a law degree, so…” He smiled.

  “Wait, you’re a lawyer?” My mouth fell open in shock.

  “Indeed. I used to work in Mr. Addison’s firm, but life called me in a different direction.” He saw my confusion and he took a seat next to me, pulling the stack closer.

  “His butler is a lawyer. That’s unreal…” I unintentionally said it out loud and tried to pretend I didn’t as he pointed at the first piece of paper. Luckily, he didn’t seem to care.

  One by one he explained all of the documents to me. The first set was a guardianship agreement, which allowed him to essentially become a guardian to an adult. Walter explained that the paperwork basically gave him the ability to give me things without the state recognizing them as gifts and charging me taxes. It was a little complex, but the gist of it was that he wanted to add me to his insurance, and get some tax breaks for everything he was doing. It sounded simple enough after Walter explained it but the paperwork still looked Greek to me.

  The second set was a little easier to understand. It was a college application and some forms so I could take placement tests. The last set was a lot more complex. It was a contract, and my heart started to beat when Walter explained the terms. I was agreeing to finish college, and if I didn’t, I would owe every dime Mr. Addison spent on my tuition back to him. It also had some provisions for me, like a meager allowance, clothing, food, and an agreement that Mr. Addison would have to offer punishment as an alternative to breaking the contract entirely if I violated it. I nervously signed the last document and threw the pen down.

  “There, I guess he owns me now?” I asked with a smile, but Walter didn’t smile.

  “Indeed, he does. Another pound of flesh for his collection...” Walter gathered the documents and disappeared from the room, leaving me a little uncomfortable about what I had just signed with his parting words.

  I met the maid next, a lady in her fifties named Gertrude. I had to jokingly ask if she was a lawyer as well—she wasn’t. She was actually the widow of an employee who worked for Mr. Addison and died in his early thirties due to heart complications. Mr. Addison offered her the position until she got back on her feet, and she enjoyed it so much she never left. She did such a great job that Mr. Addison never had any issues with letting her stay. It appeared that the butler, the maid and Mr. Addison were the only ones who lived in the house.

  The driver was always on-call, but he didn’t reside with them. After getting a good lay of the house, and the grou
nds which included a swimming pool I couldn’t wait to try out when it got warmer, I retreated back to my room to wait on Mr. Addison’s return. I was practically skipping down the stairs by the time he got home, anxious for some form of communication. The second I saw him, I had a flash to my dream, and my experience in the tub, which forced me to stifle an awkward look.

  “Walter said you signed all of the paperwork?” He entered the house and put his coat on a rack by the door.

  “I did, yes sir.” I nodded and walked with him to the dinner table where he poured liquor over a few large ice cubes and sat down.

  “Good, I’ll start making the arrangements for your placement tests, and I’ll have a tutor start coming by each afternoon to help you prepare.” He motioned for Walter to bring the food.

  “Thank you.” I was beginning to feel like the situation could work for me, even if it was a little strange.

  After dinner was complete, he took me on a tour of the house. It was like a large castle, with so many twists and turns I was sure I would get lost without him there to guide me. As we walked, I caught myself staring at him, studying the differences between the man in my dreams and the real version of him that walked in front of me. There were numerous differences, but also several similarities. Despite all my hesitations, I could feel myself developing more than just an interest in the life he had promised me.

  Chapter 8

  The next day I woke up to noise downstairs. I was alarmed by the commotion, so I changed from my pajamas into the dress I had worn the night before and walked downstairs. My hair was a mess and the night had not been kind to my makeup, but I still needed to know what the terrible racket was coming from downstairs. When I could see the entrance below, I saw an older lady with silver hair standing next to suitcases.

  “Abby!” I heard Mr. Addison’s voice carrying a rather jovial tone. “Come downstairs and meet your tutor.”