Breaking Little Emily (Dark Age Play Romance) (My Little World Book 4)

by Becca Little

  “Yes sir.” I nodded quickly.

  “Good, I thought you would.” He smiled.

  “So, what about Ms. Hattie? Won’t she find it odd that you have me chained up here wearing a dress and a diaper?”

  “No.” He shook his head and smiled. “Let’s just say Ms. Hattie has used this very same method to find her a nice little girl to service her needs as well.”

  “What?” I blinked a couple of times.

  “Like I said, this was common practice at one point. Ms. Hattie’s family is from the old country as well.” He walked to the door. “She’ll be here shortly.”

  I finished getting myself ready for the day and loaded up the laptop he had provided me with. I quickly found that everything I could access except for the school website and a few literary sources were blocked. There were no options for me to check social media or even look at the news. As I sat there going through the laptop, I heard a rustling sound from the hallway and saw an older lady power-walking towards my room.

  “You must be Little Emily.” She said with a smile. “Aren’t you just the darnedest, sweetest looking thing.”

  “Hel…Hello.” I said awkwardly.

  “Don’t be nervous my dear, we are going to be great friends.” Her smile was warm and inviting, but I felt like there was something sinister beneath her emerald colored eyes.

  “I think my first class is about to start.” I said as the laptop blinked to life.

  “Good. You pay close attention. There might be a pop quiz.” She nodded. “I’m going downstairs to make a bit of tea.”

  I paid attention the best I could. The professor was a nice, older man with a bald spot that was visible to me due to the angle of the camera. He talked fast, and I felt like I needed to be taking notes. Most of the local classes I had attended didn’t do much on the first day except introductions and overview. He went right into the lecture as if everyone already knew the syllabus. I saw it on the desktop of the computer so I loaded it up and quickly tried to catch up.

  “How’s it going, dear?” Ms. Hattie asked when she returned.

  “I think it’s going okay. I’m trying to keep up.” I replied.

  “Make sure you do.” She said as she sat down and drank her tea.

  She stayed with me during the day, through all three my classes. She seemed to be paying careful attention to me. My last class wrapped up close to one in the afternoon and I was very hungry. I normally got food around eleven-thirty so my stomach was rumbling and breakfast was not keeping me going. I finally closed the laptop and Ms. Hattie took it from me, putting it on a desk in the corner. I heard Stark coming up the stairs a few minutes later.

  “How did my favorite college student do today?” He asked as he walked into the room.

  “It was good—” I started to speak.

  “I wasn’t talking to you, Emily. Know your place.” He pointed his finger at me and turned to Ms. Hattie.

  “She was dreadful.” Ms. Hattie stated. “She wasn’t prepared, she didn’t take hardly any notes, and she practically zoned out through her entire third class!”

  “What?” I replied. “That isn’t true.”

  “Really?” Ms. Hattie turned to me. “Then tell me what book your literature professor recommended that you read before the end of the week?”

  “Um.” I tried to remember, but she was right. I wasn’t paying close attention. “It’s on the syllabus.”

  “You shouldn’t need the syllabus. You should have written it down.” She put her hands on her hips. “See, I told you. She was dreadful.”

  “I see.” Stark nodded. “Well there will be no lunch today and you will be caned immediately.”

  “Stark!” I shook my head. “Come on!”

  “I’ll wait downstairs.” Ms. Hattie said.

  Stark walked over and removed the chain. I struggled as he fastened the leather straps to my legs and lifted them up. There was little I could do once I was rolled back on my neck and my feet were strapped to the bedposts behind me. Even my hands couldn’t really protect me in that position. He removed the diaper, threw it in the garbage can, and carefully pulled my dress away from my bottom.

  “You don’t have to can me!” I said with an urgent tone. “I’ll do better tomorrow, I just haven’t been to school in a while!”

  “You should have done better today.” He said as he pulled a cane off the wall and turned back to me.

  “Please don’t…” I begged as he positioned it against my bottom.

  “You will get six of the best.” He said in a dry tone. “It is a traditional method of caning naughty schoolgirls.”

  “Six isn’t so bad…” I said lightly to myself, but then the first one landed. “OUCH!”

  “Yes, these a little harder than the ones you got the first time I caned you.” He said as the second one came down.

  I squealed and squirmed as the can continued to fall. I didn’t realize six strokes could hurt so much. By the time he was done, there were red marks across my bottom and a few of them had started to raise up as welts. The skin wasn’t broken, but it felt like fire. He left the straps there as he got a fresh diaper and slid it on me. The material was rough against my bottom and made it continue to sting. He finally released the straps and hooked the chain back up.

  “Are you going to do better in school now?” He asked.

  “Yes sir.” I nodded.

  “Good.” He said as he turned and left the room.

  Sitting there with no dinner was agonizing. My stomach felt like it was practically eating itself when he finally appeared with my dinner tray. After I ate, I got the laptop and went through each syllabus, taking notes and planning the assignments out. It was going to be a lot of work, but I certainly didn’t want to get caned again. One lesson about school was enough for me to commit to being the best student I could be.

  Each day, after my studies were done, Ms. Hattie would give Stark a report of my progress. If he was satisfied with it, I got a hug and my lunch was served. If he didn’t like what he heard, I was caned and there was no lunch offered. After lunch, or the lack of lunch, I was expected to learn piano and practice singing. I was always a mediocre singer at best, but Ms. Hattie found online instructional videos for me to watch, and she offered the support she could.

  In her youth, she was apparently quite the magician with the piano keys, but her age had made her bones too stiff to churn out beautiful music. Stark would sometimes come and listen, but he rarely stayed for the entire lesson. Usually, he was too busy at work, and his only moment away was to get his progress report on my education. It was nice to know he cared enough to keep checking on me, but I did not like it when I disappointed him. Outside of my immediate family, nobody had ever put that much effort into my future.

  Chapter 6

  When the lessons were done each day and Ms. Hattie took her leave, I was allowed to have time to myself until Stark returned with my dinner tray. He changed my diaper if it needed it, and then cleaned me up. His fingers would usually explore me a little bit during those sessions, so I did my best to have a dirty one for him just to feel his touch. He never brought me to orgasm, but it was nice to have that bit of stimulation, especially the way he did it. One day, after I had been going to school for several weeks, he arrived at dinnertime with no tray.

  “I’ve got a surprise for you.” Stark said as he walked into my room.

  “I hope the surprise isn’t that I’m not getting dinner.” I said as I looked at his empty hands.

  “Not at all.” He smiled. “I would like for you to join me downstairs for dinner.”

  “Really?” I felt giddy as he removed the chain.

  It was strange seeing the house again. I really didn’t have much of a chance to see it the first time he brought me inside. I noticed that it was decorated with many Victorian era items. The couch and chairs weren’t from my lifetime, and an old fireplace had a large wooden mantle that not only sat on top of the fireplace, but also extended up to create
carved shelving. A quick peek in one of the rooms we visited revealed a vast library of books. We finally got to the dinner table and he placed a plate in front of me.

  “Did you decorate this place yourself?” I asked.

  “Not really. I added a few things, but that was about it.” He said. “The craftsmanship in this stuff was meant to last forever.”

  “Yeah.” I nodded.

  After dinner was over, he walked over to a humidor and pulled out a cigar, lighting it up as I continued looking at the decor. After I made a circle around the living room, he motioned for me to join him on the couch. I couldn’t deny feeling a little excited when I sat down next to him on the couch and cuddled me. We really didn’t have enough of that in our arrangement and I missed the intimacy that went with a traditional relationship—outside of sex, of course. He draped his arm over me and pulled me close as we watched television.

  “I want to talk to you about something.” He said as he exhaled a large cloud of smoke.

  “Yes sir?” I had quickly learned that yes sir and no sir was the best way to give him the respect he deserved.

  “I don’t think I’m going to put the chain back on you tonight. I believe that you’ve earned the freedom to make this house your home. I’ve been very pleased with your progress so far. Ms. Hattie says that you are doing an excellent job with your studies, and I can’t deny how far you’ve come on the piano. I’m ready to trust you more, and give you more freedom, but you must show me every day that you are thankful for them. As you do, I will consider giving you more freedom.” He smiled and ran his fingers through my hair.

  “Thank you so much!” I could barely contain my excitement. “I promise I’ll be a good girl for you, and I’ll never disappoint you.” I hugged him tight.

  Serving as his submissive future bride meant little things like that were earned, and they meant so much to me. His simple gesture made me feel like the relationship had progressed to another level. The doubts clouding my head began to fade a little bit. There was something natural and organic about our role.

  Perhaps I had always known I preferred the role of a submissive, or perhaps it just had not been unlocked yet. With Stark, it came natural. I still couldn’t believe my sister had ever managed to submit to him in any way. I had to wonder if losing her was what turned him into such a careful man, so careful that he kept me locked in chains for months.

  Even as his submissive Little Emily, the punishment only came if I violated one of his rules, and I had quickly learned how to avoid it. There was a creeping part of me that often found my heart and body craving it. The pain had unlocked something primal inside of me that I attached myself to like some sort of urge. The few times I did do things to draw his wrath, I found it unnatural and I wasn’t able to fulfill the need which had begun to surface.

  “I want you to show me how thankful you are, Emily.” He moved his hand through my hair again. “Can you do that for me?”

  “Yes sir.” I knew exactly what he wanted. I had learned to pick up on his body language.

  I sank down to the floor between his legs and began to unfasten his pants. I loved showing him how thankful I was. Being able to satisfy him and bring him a sense of pleasure was the best part of our relationship—outside of my own pleasure of course. When his pants were unbuckled and his cock was pulled out of them, it began to swell in front of my eyes.

  I stroked up and down his shaft until it was hard as a rock in my hand. My smaller stature made his cock even larger than it would have been for some women. It was a monster in my hands, and a behemoth in my mouth. I parted my lips and extended my tongue, rolling it around the head and taking a little bit of it into my mouth. Over the course of the time we had been together, I had learned exactly what he liked and how to satisfy him in a way that always made him smile.

  I looked up and saw a look of satisfaction etched on his face as he puffed on his cigar so I started to take his cock deeper into my mouth. Learning to deep throat his large cock easily had been a chore at first, but I was a professional at it by that point. I no longer feared it, so I worked my way up to it and teased him the way I knew he liked it.

  “That feels so good, Emily.” He rubbed his fingers through my hair as he gasped.

  I slowed the momentum down as I continued to work him into my mouth. I let him linger there where he was only halfway in, and bobbed up and down on that portion of his cock. After sucking on it for several minutes, I pulled it out of my mouth and started to move my lips down the shaft, gently kissing and licking it as I did.

  Once I got down to his balls, I took them in my right hand while stroking his cock with my left. I kissed from one to the other and then extended my tongue out, rubbing it against it. I had found out early just how much he loved to have them played with and touched, so I made it a part of my ritual when I submitted my mouth to him. His cock swelled against my stroking motion, but I knew it was the teasing on his balls that was doing it. I licked around each one, and then took them into my mouth.

  “So very good…” He moaned.

  I gently sucked and caressed while rolling my tongue around the massive orbs until he was pushed to the edge. I let them slowly sink into my palm again and moved them out of the way so I could focus my tongue on the underside. I licked and traced with my tongue until I was down to his perineum. It didn’t take much action there until he was so engorged it felt almost painful.

  “You know just what I like; you’re the best.” He pushed his body forward on the couch and rested the cigar in his mouth. His eyes closed as his cock throbbed in my hand.

  He had never said I was the best before. I had to suppress a smile and stay focused on my task. My mission was to make him cum, and after I had worked over his balls and his perineum, I started working my way back up the shaft of his cock. When I got the head again, I opened my mouth wide and let it slip inside.

  I let it sink past the midway point until it hit the barrier in the back of my throat and then I pushed past it until he was all the way in. My lips touched his balls as his cock was pushed to the back of my throat and past the barrier. It always took a moment to adjust so that I didn’t gag, but I learned how to control my reflexes quickly. After he sat there for several seconds, I could start moving up and down his shaft, taking him all the way into my throat with each motion.

  As I sucked his entire length, I traced his balls with the tips of my fingers and gently rolled them in my hand. The combination was always enough to keep him hard and throbbing in my mouth and that time was no different. I felt his sigh and moan as he was nearing the point of no return. I pulled his cock to the tip of my tongue and then down into my throat over and over until he gasped.

  “I’m going to cum…” He placed both hands on my head and puffed his cigar a few times as it rested in his teeth. There was something so masculine and sexy about that. Sucking his cock always made my pussy tingle, but images of his extreme masculinity just made me gush with desire.

  I could feel him taking control as his hips gyrated and his cock was pushed into my throat. I did everything I could to help bring him the pleasure he was hunting, but I was ultimately just there to satisfy his lust in that moment. I was okay with that. I knew I would get a reward before it was all over, and I would serve him in any way possible until that point.

  I let him guide my head until my mouth was providing him the maximum level of comfort. He pushed me forward and leaned into my mouth. I opened it for him slightly because he loved to see his seed deposited on my tongue. He looked down at me and I brought my eyes up to meet his. That was what he desired.

  He wanted to see me hungry for his cum and ready for it. The first spurt landed on my tongue and I moaned, begging for more. He dumped more directly into my mouth as he watched every wave of stringy cum land in my mouth. After he had filled my mouth, he wiped the last remnants on my lips and watched as I licked them clean and swallowed my prize. When it was done, I opened my mouth and presented myself for inspection. He looked,
pulling my gums back and forth and then nodded.

  “Good girl, Emily. I’ll make you a treat.” He stood up and adjusted his pants while I remained on the floor.

  Chapter 7

  I wasn’t sure what kind of treat I was going to get. When he returned a short time later with a bottle in one hand and a glass of whiskey in the other, I opened my eyes wide. I had been subjected to diapers and frilly dresses, but I had never had a bottle before. He sat down on the couch and ran his fingers through my hair as he looked into my eyes. The dominant, possessive man I loved seem to fade as he stared at me and I felt genuine love in his touch.

  “This is a special bottle.” He said as he gave it to me. “I think you’ll find it to your liking.”

  I stared at it for a moment and then finally tilted it up. The first thing I tasted was milk, but after a few sips, I realized it wasn’t just milk. There was something strong and sugary hidden beneath the dairy-coated flavor. As I drank more of it, I realized it was spiced rum. I hadn’t had alcohol at all since I had been in the house, so I drank the bottle slow once I realized what was in it.

  “You won’t be my Little Emily forever.” He said as he sipped his whiskey. “One day you will be my bride.”

  “Will I be able to come and go as I please at that point?” I asked.

  “Only when you have a driver and a bodyguard.” He replied. “I’m still very paranoid.”

  “I understand.” I nodded.

  “I have everything situation so I can run the business from here for the most part.” He nodded. “When I’m not working, we will have a normal life. We’ll go to the movies, go dancing, all of that stuff.”

  “That sounds wonderful.” I said with a smile.

  I cuddled beside him and sucked on my bottle while he rubbed his fingers up and down my body. He ran his fingers underneath my dress and stroked my pussy through the diaper while we watched television. It was a subtle gesture, but it felt so good. I leaned against his warmth and spread my legs open, drinking the bottle rapidly as he lightly stroked me. When I got near the bottom of the bottle, I was tingly and tired from the rum, but extremely turned on from the attention he was giving me.