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

by Becca Little

  “I appreciate that, but I’m doing okay.” I faked a smile, which wasn’t hard since my face had actually formed a genuine one at his previous comment. My head was also still spinning from the orgasm, which was getting amplified from the wine. Despite practically becoming an alcoholic, I was still quite the lightweight.

  He told me stories about my father, and a lot of them were of his youth, before I was born. He had lived next door for a while before I was even a splatter in my mother’s ovary. Once he started telling me stories, I felt at ease with him. The wine he brought seemed to be a lot stronger than what I was used to, and as it warmed me up, I started to feel really at ease with him. It was so easy to talk to him, and I didn’t feel antisocial. We talked until the bottle of wine was gone, and my head was buzzing. I was ready to open another, but I didn’t think my legs would function enough to get me across the living room without some awkward stumbles. I looked at him, and perhaps it was the wine-goggles, but I still felt attracted to him. He was so handsome, despite being my father’s age. I was always a blabbermouth when I started drinking before I became a recluse, and the next thing I knew, I was spilling things probably best left unsaid.

  “I used to watch you…” I felt my heart racing as I said it.

  “I’m sorry, what?” I wrinkled his brow.

  “When I was younger... I used to watch you through your window with that girl you were dating.” I didn’t know if he would connect the dots.

  “Oh? Oh!” They quickly connected. “Penny, what you saw was something between adults…”

  “No, it didn’t bother me, I promise. I don’t even know why I told you…” I felt quite stupid. In my head, I thought it would be something we laughed about, but I could see he was getting uncomfortable.

  “Was it something that interested you?” He seemed to lose a little bit of the tension as he studied my face.

  “Maybe…” I picked up a cigarette and lit it.

  “What was it that you found interesting?” I could see he was intently watching my expression. I felt myself tingle a little inside.

  “Just… The way you took care of her.” I admitted. “Of course, I thought it was strange that you spanked her, but you seemed to care about her a lot.”

  “Sometimes a spanking is necessary when you care about someone.” He patted the seat next to him. “Come sit next to me.”

  I don’t know why I moved, but despite my shaky legs, I did as he asked. When I sat beside him, he rubbed my back a little bit and then took the cigarette from my hand, stabbing it out in the ashtray. He put both hands on my shoulders and started to rub. I had no idea how tense and tight they were. His hands were like magic, pushing and kneading years’ worth of stress out of me. After he was done, he took me by the hand. I didn’t know what was happening or if I even wanted it to stop. He picked me up in his arms and walked me towards the stairs. I was pretty sure we were about to have sex, and my mind was blowing up with confusion, but I didn’t fight it—I wasn’t sure I wanted to fight it. When we got to the top of the stairs, he walked with me into the bathroom.

  “What are you doing?” I asked as he placed me back on my feet.

  “I’m going to take care of you. Just relax.” He put a towel on the floor and started a bath.

  I was so dirty and disgusting. I felt ashamed when he pulled my clothes off. He certainly noticed the stains in my panties and the wetness between my thighs, but he didn’t say anything. I felt like a child, and it had been so long since anyone took care of me—I didn’t even take care of myself. He started with my father’s straight razor. I wasn’t extremely happy to have it near, but he cut along the edges of my hairline like a surgeon. He removed all the hair from under my arms, on my legs, and I closed my legs when he went for the hair around my pussy but after a little nudging, I opened them and allowed him to work. Within a few minutes, I was shaved bare from the waist down. After that he took me to the bath and placed me in the water. The soap burned the areas he had shaved, but he lathered and cleaned me until the water was dirty and I felt a little embarrassed to see how bad I had let myself get. He untangled my hair, washed it with shampoo, and when I was clean, he dried me off.

  “Can I fix your hair?” He asked as he rubbed the towel through my clean locks.

  “Okay…” I was willing to give myself to him. He was so kind and my fantasy was taking hold in front of my eyes.

  He picked up my brush and my comb and started to remove the knots I had let my mangled hair become. After a few minutes of working on it, he had it perfectly groomed. The blow dryer was turned on and he worked my hair in his palms until it was dry and silky smooth for the first time in months. He picked up some ribbon from the counter—I hadn’t worn it in years—and he tied them into my hair, creating perfectly shaped pigtails. I instantly had a flashback to the girl I saw through the window. He took me to my room and dug around in my closet until he found a dress he liked. It wasn’t one I would normally wear, and it had been bought for a Victorian themed party years before. I went for panties, but he shook his head and helped me into the dress. The person looking back in the mirror was not one I recognized.

  “I look…” I shook my head.

  “You look like a very good little girl.” He smiled. “However, we both know you haven’t been a good little girl have you?”

  “What do you mean?” I looked at him in confusion.

  “You’ve been quite a naughty little girl. You let yourself become a filthy mess, didn’t you?” He sat down on the edge of the bed and looked at me.

  “Yes…” I nodded.

  “Yes what? I know your parents taught you respect.” His tone hardened as he said that.

  “Yes… Yes sir.” I nodded. They definitely did teach me manners.

  “Come over here.” He motioned towards me and I moved towards him. I felt almost lost in the moment I had only witnessed from a window. “I think it is time we corrected some of that naughty behavior, don’t you?” He pulled me across his knee and flipped up my dress revealing my bare bottom.

  “Are you…” I knew what was coming and I knew I deserved every bit of it.

  “I’m going to show you what happens to naughty girls.” He said as his hand came down hard on my bottom.

  In theory, a spanking was sexy and fun. In reality, it stung my bottom from the very first smack. I wiggled a little bit, but he held me in place and his hand started to come down rapidly on my bottom. As scared as I was, I had craved it for a very long time. I held onto his leg as he punished me. My bottom bounced underneath his hand and I could feel it getting warm to the point it was almost burning, but he didn’t stop. He landed one on the right side of my bottom, one on the left side, and then one directly in the middle. He repeated the motions over and over as I squirmed around and winced in pain. After he had delivered fifty to my bare unprotected bottom, he paused to adjust me on my lap. I had almost squirmed and wiggled away.

  “Oww! Ouch! That really hurts!” I said with a whimper in my voice.

  “Normally, I would not spank you like this, but I think you need a reminder that you are an important person in this world. You have to find your place and enjoy your life. Your parents would not want you wallowing about in the house, smoking and drinking your life away.” His hand started to fall again.

  His words left a stinging in my brain that felt worse than the spanking. He was right. My parents would have told me not to drop out of school, and not to let myself become the sad woman I had become. His words were backed up by his punishing palm as he rained down on my bottom. I felt tears in my eyes and then my eyes overflowed as sobs rushed into my throat. I had cried so much, but the tears he created with the spanking were different. They made me think and I quickly realized what he was saying made a whole lot more sense than the life I had been living. After fifty more smacks, his hand got harder and he started to land multiple smacks in one spot before moving on. My feet kicked and my whole body reacted to the punishment. After another twenty five, he slowed d
own and landed several extremely hard smacks before completely stopping. I lay across his lap, still sobbing, even though he was no longer spanking me.

  “I’m going to come back tomorrow, and I expect this whole house to be clean. I want to see fresh food in the refrigerator, and I want to see the vibrant young lady I know you can be.” He said calmly before letting me stand.

  “Yes sir…” I pushed tears out of my eyes.

  He hugged me tight and let his hands linger on my body. I couldn’t believe that my sense of shame from being exposed to him evaporated so quickly. I didn’t want him to let me go. I began to feel a deep connection that was probably just my grief manifesting and clinging to the only person who had shown me true compassion, but I didn’t want it to end. He took his leave, and with my bottom bright red and still stinging, I started to clean. I was up until nearly three in the morning getting everything scrubbed clean. The dress he had put on me was a mess of dirt and cleaning materials. I took it off and tossed in the wash before crawling into bed. I hadn’t been in my bed for so long that the soft blankets and sheets felt like a new experience. My bottom had mostly stopped hurting, but there was still evidence of the spanking. I propped myself up and began to move my fingers down between my legs. He was all I thought about as I pleasured myself, and when I was done, my body quickly fell asleep.

  I woke up early the next day and I immediately cleaned myself up. I put my hair in pigtails and found another dress. It wasn’t quite as immaculate as the one he had chosen for me, but it fit a similar motif. I went to the grocery store and carefully picked out some healthier food—at that point anything would have been since I was dining on pizza. Instead of wine, I opted for coffee when I came back home. I wasn’t sure what to expect when he arrived, but I wanted everything to be perfect. He didn’t even knock when he arrived. He walked into the house like it was his, and dropped a bag on the floor.

  “Good job. It looks like you’ve made some real progress.” He nodded as he looked around.

  “What is in the bag?” I asked as my eyes looked past him.

  “You’ll find out soon enough.” He motioned to the kitchen. “I’ll make dinner for us.”

  He turned the hodgepodge of food I had brought home into a functional meal while I sat in the living room and watched him. He was like a surgeon in the kitchen, cutting everything to fit into the meal design which emerged as he worked. A short while later, he called me to dinner and I sat down in front of a plate filled with vegetables and grilled chicken. It wasn’t my favorite, especially the vegetables, but I ate everything on my plate. It had been so long since I had real food that it tasted like perfection against my taste buds. It wasn’t long until he was taking me upstairs again with the bag in hand.

  “You’ve poisoned your body for so long, I think you need to be cleaned from the inside out.” He said as he placed me on the bed, positioned on my hands and knees.

  He pushed the fabric of my dress up off of my bottom and then removed my panties. When I saw the tank he produced, along with a giant bottle of murky liquid, I was scared. The bottle had a tube that went down to a hard rubber nozzle. He pressed it against me and then pushed the nozzle all of the way in. I realized he was giving me an enema. The murky liquid flooded through the bag and into my body where it stung and burned a little big. After he was done, he pulled the tube free and placed a finger on my asshole. I flinched, but I remained steady underneath his touch.

  “You need to hold it all inside. Don’t lose a drop. I’m going to leave you here to think about this for a little bit. Remember, not a drop spilled.” He left the room and I tried to remain still.

  He was gone for nearly an hour. Everything in my stomach seemed to cramp and gurgle while he was gone, but I did exactly what he said and I held it in. When he reappeared at the doorway, I could smell cigar smoke, and I assumed he had been downstairs enjoying one while I suffered in my room. He took me to the bathroom and let me relieve myself, then took me back to the room. This time he placed me on my back and reached into the bag once more. When he pulled it out, I saw that he was holding a diaper. I remembered seeing that through the window, but it still didn’t prepare me for my dress to be pulled off and the diaper to be fastened around me. After he was satisfied, he helped me to my feet. The final touch was a pacifier that he shoved int my mouth.

  “You’re going to wear this for a while.” He said as he smacked my bottom. The diaper did at least offer some form of protection against his hand.

  I followed him downstairs and he started a movie. He lit another cigar and left me in the floor while he watched and smoked. I badly wanted a cigarette, but it didn’t seem appropriate in my current role. After I played in the floor for a little bit, he brought me up on the couch and cuddled me in his arms. They were strong, but loving, and although I had no idea where our relationship was going, I wanted to take it to the next level. I placed the pacifier on the table in front of me, then moved closer as his arm tightened around my shoulders.

  “If you can’t keep your pacifier in your mouth, we’ll have to find something else to keep those lips busy.” He motioned to the pacifier.

  “Like what?” I asked.

  “Like a much bigger pacifier.” He said as he rubbed his hand across his pants.

  “Maybe that is what I want…” I wasn’t sure if it really was, but I definitely desired him.

  He began to unfasten his pants to give me what I asked for, and when they were open and his cock was exposed, I found myself marveling at the sight. He put my college boyfriend and the few men I had been since to shame. I started to wonder if I had asked for something I couldn’t even handle. I dropped to my knees in front of him and pulled his pants off of his legs. I took his cock in my hand and moved up and down it for a few seconds before taking the tip into my mouth. I got my mouth around several inches with a little bit of struggle and then started to roll it around in my mouth while moving up and down his length. It was definitely a pacifier to be proud of. After several minutes of sucking, I got him into my throat and started to try and force him down the rest of the way. It took some gagging and several attempts, but I finally got it. After I did, I started moving up and down his cock with relative ease, stroking it with my hand and it went from the edge of my lips down into my throat.

  “You sure do know how to be a good little girl.” He said with a sigh.

  I concentrated on the task at hand, but I felt warm and fuzzy inside as he complimented me. I pulled my mouth off of his cock and started to kiss down the sides. When I got to his rather large balls, I licked them several times and then took them into my mouth one after another until he was moaning and groaning against the pleasure I was creating. I moved my lips and my tongue up the entire length of his cock while he caressed my head. He started to force himself in faster, and I knew he was about to cum. His cock throbbed and pulsated against the back of my throat several time before he took a pigtail in each hand and started really driving it in. I let him guide me up and down his cock as hard and fast as he wanted until I felt the salty pre-cum on my tongue. He forced his cock deep inside my throat once more and then I felt shooting jets of cum. I swallowed as quickly as I could and once his breathing returned to normal, he released his grip on my hair.

  “Come up here and cuddle with me.” He said and I quickly moved onto the couch.

  He smoked and watched television while I nestled against his chest. I loved the feeling of being his arms and having my stroke my naked flesh. He squeezed my breasts and twisted them a few times leaving them perky and hard. A few times his lips drifted down to my neck and sent electricity through my body. When I needed to use the bathroom, he told me to stay and use the diaper. It was quit humiliating, but I did as he asked. I wanted to be a good girl for him and I didn’t want to end up across his knee again. After a little time passed, he took me upstairs and stripped the diaper off. He used a baby wipe to remove all the residue and I felt myself getting hot and turned on from the feeling of him rubbing my pussy.r />
  “Do you want to be a big girl for me?” He asked as he rubbed my pussy with his finger.

  “Mmm hmm.” I said quickly as I chewed on my lips.

  He rubbed my pussy for nearly ten minutes getting me wet and then he put his mouth on my clitoris. His tongue rolled around it until I thought I couldn’t take anymore. He pulled his mouth back and climbed on top of me. I had never fantasized about sex with him, but once his gigantic cock started to slide inside of me, I knew I wanted it more than anything else in the world. My whole body felt alive with pleasure I hadn’t felt in years as he expertly began to move in and out of my pussy. Everything tingled and quivered as I burned with desire for him. He brought me to the edge numerous times and then slowed down to enjoy the experience. By the time he had me to the point of no return, I started moving my hips, trying to force him deeper. He obliged and started to hammer my pussy harder than any man had before. Within a few minutes, I felt my body reacting and then I had an orgasm while he continued to fuck me. I didn’t stop there—he drove me to the edge over and over until my body was wracked with orgasm after orgasm. Just when I thought I couldn’t take anymore, his breathing intensified once more and his cock throbbed inside of me. His cum began to spew, and I was surprised he had anything left after what we had done downstairs. Once he was done, he pulled himself off and lay next to me, pulling me close once again.

  “Would you like to be my Little Penny?” He asked as he rubbed his hands across my body.

  “I’ll be anything you want…” I let out as gasp as his fingers drifted across my ribcage.

  Despite the strange nature of what we did, I never had any regrets about it. He was significantly older than me, but he treated me like a little girl when I needed it, complete with a trip over his knee when necessary, and he treated me like the woman I was destined to be when it was over. There were so many layers to him that I struggled to peel back, but I needed to see them. He opened up about things in his life, and in that strange encounter, I found the love of my life. I didn’t need the games men my age played, I needed his maturity and his strength. I was a lost soul, and it was difficult for me to let go of the past, but he helped me find my own future. He played so many roles over the course of our relationship from boyfriend, to stern “Daddy”, and eventually he became my husband. I gave myself to him, and he gave me my life back…