Little Jessy & The Cowboy (Western Age Play Romance) (My Little World Book 6)

by Becca Little

  “Please…” My scream rolled out of my throat in a sob that caked my vocal cords. “I’m sorry.”

  “Every time you disobey me, you will be punished. Starting tomorrow, you will get a spanking before bed just like the disobedient little girl you are.” His words were calloused and firm.

  “Yes sir…” I sank into my despair, realizing the switch was only the beginning of my punishment.

  When the switch finally stopped landing fire-streaked agony on my bottom, I let out a sigh of relief. It still hurt, but I was glad the worst of it was over. He helped me stand and hugged me close. I cried into his shoulder has he held me there. The physical release of the emotional pain had left me feeling strange. It was almost like I needed to feel it to find that focus again. It felt so good to be held in his arms. They were strong and made me feel safe, even though he had just punished me with little mercy in his touch.

  “I’m so sorry…” I whimpered as the tears fell.

  “I was trying to teach you self-control; I wanted you to learn how to take your pain and release it.” He said as he referenced the enema I had flushed out.

  “I’m ready…” I said with a nod. “I’m ready now.”

  He took me back inside and tended to my bottom with some ointment. It took the fire away, even if the pain was still present. After that, he put the enema in again and filled me with a colder fluid. It cramped worse, but I was determined to hold it. There was no way I was going to disappoint him again—letting it go without permission again would be disappointing myself. I stayed there for what felt like an hour with my body wracked with cramps and chills from the cold. It would have been a lot easier to just hold the warmer liquid from earlier.

  When he finally showed up and let me find release, I felt like the weight of the world had been lifted off me. I felt like such a foolish child for my actions, and I realized he was just trying to help me. He put the diaper on me, and then helped me put on a pretty dress that hung right below the cloth. He took me to the kitchen and fixed himself some food. I knew I wasn’t getting any, so I smiled when he handed me the old glass bottle. He put me on the floor next to his feet instead of letting me sit at the table and then handed me the bottle. I looked at him with confusion, but I was past asking questions. I just accepted it and nodded.

  “What is this for?” I asked as I held the warm milk in my hand.

  “You no longer get to sit at the table.” His words were firm. “You will have to earn that right again.”

  I sat at his feet while he ate and I drank my meal from the bottle. I felt quite a bit of humiliation, but I trusted him. I was already strong and more emotionally stable than I had been before he started trying to heal me. I knew there was more in my heart than love for the man who had taken me as his Little Jessy. I wanted more than that. I wanted a permanent place with him. I wanted to repay him for his kindness—and his firmness—by satisfying him for the rest of his life. I felt like I belonged with him, regardless of the circumstance. I wanted him to be the man I married, I just didn’t know how to get there from the position I was in at his feet.

  Chapter 8

  The next day, I tried my best to be the perfect little girl for him. I didn’t want to disappoint him in any way with the promise of a spanking hanging in the air. I had only been spanked a couple of times, and it had been a long time since I had one. My trip to the woodshed for helping myself to pie was the last time I had been punished at all. I remembered them being a lot longer than the trips to the woodshed, and they made my bottom hurt quite a bit. When I walked upstairs after dinner, I knew why he followed me. There was no way of escaping the inevitable. When we got to my bedroom, he took me by the arm.

  “You’re not going to try and go to bed without what we talked about are you?” His tone was firm.

  “No sir.” I shook my head and stared at the floor.

  “Remove your dress and put on your gown.” He pointed at the gown hanging on the chair.

  Once I was dressed, he led me to the bed and sat down. He pulled me across his knee and pulled my gown up until the diaper was exposed. Any hope of getting a spanking on the thick diaper was extinguished when he started to remove the pins. Once it was on the bed beside me, I was naked from the waist down. He positioned me on his knee so that I was hanging across it with my bottom in the air. I swallowed my pride as I prepared to have my bare bottom spanked by his large, powerful hands.

  “You will be going to bed with a sore bottom every night until I feel like you can obey me properly.” He placed a hand on my exposed bottom.

  “Yes sir…” I gripped the side of his leg.

  His hand came down hard in the center of my bottom several times before it started moving to each side, landing a firm smack each time it came down. The sting of the switch had faded, but it was still buried beneath the surface of my skin. His hand started to reignite that fire, creating lines of agony that reminded me of it quickly. Having my bare bottom spanked was as humiliating as I remembered. My concerns with that started to fade when my bottom really started to sting underneath his hand. I squirmed and twisted on his knee, trying to find a moment of relief, but all I got was another agonizing smack.

  “If you don’t hold still, we’ll keep going until the sun comes up.” His threat was enough to make me stop squirming.

  “I’m sorry!” I squealed.

  I didn’t want to be across his knee until the sun came up. The time I had spent there already had left my bottom stinging and sore, especially with the switch marks still fresh underneath the crimson glow I knew he was creating between them. I felt tears coming again, and they started to stream down my face. They started to once again wash the emotions from my thoughts and ground me in reality. I knew I deserved to have my bare bottom spanked, even if it hurt. I started to squirm again as the discomforting sting turned to a slow and steady burn covering the entire surface of my unprotected bottom, but I didn’t move enough to anger him.

  “I’ll do whatever you say!” I felt a sob erupt from my throat. “I won’t disobey you again!”

  It was easy to make promises as the result of my disobedience burned underneath his palm. The thought of being in that position every single night until he felt my obedience met his expectations was scary, but I wanted to earn his trust again. I suffered across his knee and my bottom burned with each well-placed smack. When it was finally over and I felt his hand slow down, I started to slow down my breathing, letting my body relax. My bottom still burned, but it wasn’t as bad as having his hand reignite the fire each time it came down.

  “Okay.” He patted my bottom. “Let’s get you back in the diaper.”

  “Can’t I have some ointment?” I looked back at him. “It really hurts.”

  “Not tonight. You need to think about why it hurts for a while.” He helped me off his knee and hugged me tight.

  I cried on his shoulder until he put me back on the bed and wrapped the cloth diaper around my waist. The cloth didn’t do anything to help the stinging in my bottom. He slid a pacifier into my mouth—one made of wood and the same texture as the top of the bottle. I let it rest against my tongue, feeling comfort as I sucked on it. When he finally blew out the candle and closed the door, I reached into the diaper and rubbed my punished bottom. It was warm to the touch, but it wasn’t as bad as I thought it would be. I pushed the diaper down slightly and tried to see what it looked like. I could see redness in the moonlight, but the light was too dim to really see what he had done. I lay on my stomach letting a few more tears fall into the pillow before I finally drifted off to sleep.

  Chapter 9

  Every day I started with a bath, followed by an enema. I held it every time, never wavering from his expectations. Most of the time it wasn’t the medicine, and it didn’t cramp as much, but it was still very uncomfortable. I ate my meals from the bottle, drinking down the nourishing mixture he had created for me while sitting on the floor at his feet. When dinner was done and the chores were over, he would often read to m
e from one of my father’s books. The stories were glorious tales, and I regretted never taking the time to learn how to read the complex books. The stories were incredible, but my basic knowledge of words wasn’t developed enough to comprehend them without him explaining everything.

  “I want to learn to read these books…” I picked up the one he had closed. “I want to be able to read to you.”

  “Go ahead.” He stood up and grabbed one off the shelf. “I’ll help you with any words you don’t understand.”

  I understood numbers a lot better than I understood what I tried to verbalize as I struggled through the lines of text. Numbers were easy and words like meat and eggs were common enough for me to recognize them, but the rest of it was a little tough. Each time I hit a word I didn’t understand, he would help me make sense of it and then make me read the sentence again. After several weeks of trying, I could re-read things I had previously read, and comprehend what I was saying with his guidance.

  “You’re a natural.” He smiled as he lifted a glass of whiskey to his lips. “You really should have gone to school.”

  “I liked school.” I admitted with a sigh. “There was just so much work to do and I felt bad leaving my parents to do all the work.”

  “I’ll teach you.” He smiled. “Don’t worry about it.”

  We continued our daily ritual for two months. I found myself trying to read more of the words until my eyes could barely function because I knew the end of the evening meant a trip across his knee and a sore bottom when I went to bed. It got to the point I expected it, although I still tried to rationalize an escape in my head. Every few days he would ride off to town and pick up more supplies. The weather was getting cooler, which meant there would be less work to do, and less workers around. The livestock still needed us every day, but the fields were going to be barren when the first snow came.

  Over time, our life became quite mundane except for the way I lived my life. Each evening, he usually drank and we read books or talked by the fireplace. The yearning inside of me got more and more intense as the days went by, and I had no idea how to control it or explain it. I found myself excited when he was near, tingling when he touched me, and wanting him to do so much more. I knew marriage was usually customary for the sort of desire I had, but I didn’t care about the title—I just wanted to be his. One night, I couldn’t stand it anymore. The book closed and as he held me close, I moved towards his lips for a kiss.

  “What are you doing, Jessy?” He pushed me away.

  “Daddy, don’t you want me? Why are you doing this if you don’t love me.” I crawled into his lap.

  “Jessy, I care about you…” He shook his head. “Of course, I love you, and I want you, but this may complicate things.”

  “Why?” I put my hands on his shoulders. “I care about you too.”

  “I’m a very possessive man.” He leveled his gaze on me. “If I take you as my own, I’ll never let you go.”

  “What if that is what I want?” I moved closer to his lips.

  “Have you ever been with a man?” He placed his hands on my hips and started moving them up my ribs.

  “No…” I admitted. “I don’t know what to do, but you could show me. I’ll do whatever you want.”

  “Kneel down between my legs.” He removed his hands and watched me.

  I was torn between apprehension and excitement. I wanted to please him. I wanted to be more than just the little girl he watched after, but I had no idea how to do it. He kept his eyes locked on me as I slid off of his lap and sank to my knees. I had been at his feet before, but never between his legs like that. I stared at him as his hand went to his belt. He unfastened it and left it loose in his hands.

  “If you really want me to take you as my own, you have to show me how bad you want it.” He started to push his pants down. “That starts by showing me you can take all of my cock into your mouth.”

  “Okay, Daddy…” I moved closer as he started to push his pants down.

  Once his pants were pushed past his hips, I got my first view of a man’s penis. It was a rather large extension of his body, tight and almost pulsating. My mother had tried to haphazardly explain it to me when I was younger. She told me I would learn more when I got married, but I should let the man take the lead the first time. I was ready for him to show me what I had to do to please him. I reached out with my hand and started to rub it with my fingers. He leaned back on the couch and started to sigh with pleasure hanging beneath his drawn breath. I leaned forward and kissed it, dragging my tongue along the side.

  “Just like that…” He smiled. “Show me how bad you want it.”

  I kept moving my tongue against it, sliding up to the head. When I ran my tongue across that, I could tell he really liked it. I felt my pussy getting wet and tingling with desire as I caressed his cock with my tongue. It seemed to get tighter and harder when I moved my tongue across it. He sighed with pleasure, and I could tell he was enjoying it. I continued the motion as it seemed to almost throb against my lips. I used my tongue to move up and down the shaft until I got to the fleshy orbs at the bottom.

  He put his hands behind his head and let out a moan of pleasure when I pressed my lips into them. I started to lick them, just like I had been doing with his cock. I could tell from the grinding motion and moans he made that his pleasure was intensifying, so I continued to work them around in my mouth. After he seemed to be buzzing with excitement, I dragged my tongue up his long shaft, watching his reaction as each spot was touched. I started to understand which areas of his cock brought the most pleasure, so I moved my lips and my tongue across them repeatedly.

  “That feels really good, but I want you to put it in your mouth.” He reached down with his right hand and guided my lips to the head of his cock.

  I parted my lips and let the head of his cock slide between them. When it dipped into my saliva, it seemed to glide naturally between my lips. I opened my mouth further, feeling my own desires burning with the images of having it in my pussy. I had touched myself a few times in my life, and I was sure it could do a lot more than my fingers did. I worked his cock between my lips, caressing it with my tongue as he instructed. My lips started to get covered with saliva that dripped down my chin, but I kept up the momentum.

  I could tell from his body language that it was getting even better when I was able to get it further in my mouth. As the motions continued, I found myself struggling with his length and girth. I wanted to show him that I could take all his cock, but it was so massive I couldn’t get all of it down my throat. I was almost there, but the rest of it seemed like an eternity. I started to feel like a failure as I bobbed up on the portion I had been able to fit in my mouth. I started to whimper as I struggled, feeling the same as I did when I was unable to take the enema.

  “Do you want some help?” He asked as I struggled.

  “Yes Daddy…” I pulled his cock out of my mouth and nodded.

  I put my lips back against his cock and let them fall open as he put his hands on my head and forced his way down into my throat. Once it hit the point where I couldn’t get it any further, he pushed it against the barrier and then it went all the way in. I let out a moan of excitement as I felt him deep inside my throat for the very first time. I struggled not to gag and he left me there with his hands firmly on my head until I adjusted to his size and the penetration.

  After a few minutes, I finally felt like I could do it on my own. I started to move up and down his cock and every time I got to the back of my throat, it slipped in just like he wanted it to. He seemed extremely excited as I did it so I continued. I brought his cock to the edge of my lips and then took him all the way into my throat over and over until I could feel him grinding and getting faster against me. I felt something squirt in my mouth.

  “You need to swallow Daddy’s cum” He pushed my head down and I felt it squirt again. It didn’t taste like milk, but it was creamy and thick like the stuff I drank from my bottle.

  He
sank his cock into my throat and I felt it throb and pulsate for a couple of seconds and then he shuddered. He bucked his hips and exploded in my mouth. It filled my throat and I struggled to swallow it. Just when I thought it was over, he pulled his cock to my lips, released some onto my tongue and then shoved it down my throat again. Several more streams of his hot milky cum coated my throat and I swallowed it down. When it seemed like he was spent, I pulled his cock to my lips and sucked down the last remnants of his pleasure. I pulled it from my mouth and started caressing it with my hand.

  “Did I do a good job, Daddy?” I looked up at him with apprehension.

  “You did a wonderful job.” He smiled. “I think it is time I returned the favor.”

  “What do you mean?” I stared at him.

  “Let me show you…” He pulled me off the floor and into his arms. He leaned towards me and started kissing my neck.

  Chapter 10

  The feeling of his lips on my neck made me tingle with desire. The wetness between my legs started to burn with a passion for his touch. He removed my dress with his fingers quickly removing the strands of fabric that held it in place. He placed me on my back with my head resting against the arm of the couch. With a quick flick of his thumb he removed one of the pins on my diaper and then the other. He pulled it free and dropped it onto my dress that was crumbled on the floor. He pushed my legs apart and started kissing the inside of my thighs, making me moan with excitement.

  “I’m going to give you a reward for what you did for me.” His tongue moved further up my thighs. “This is a treat that good girls get when they take care of their Daddy’s needs.”

  He returned to kissing my inner thighs, moving further up them as I waited in anticipation. I wanted to touch my pussy and rub away some of the hunger I was feeling, but I was sure he was going to satisfy my craving. His tongue reached the edge of my pussy and start to slowly circle it. I pulled my fist towards my mouth and started to take quick, shallow breaths coated in the pleasure I was feeling. His tongue was so much better than my finger, and it made my pussy continue to resonate with my building list.