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

by Becca Little

  “I thought you used to hate these bedtime spankings.” He brought his hand down hard and then moved a finger between my legs, rubbing my pussy.

  “I didn’t look forward to them.” I let out a moan. “But I’ve missed it.”

  “Is that so?” He pulled his finger away from my pussy and brought his hand down on my bottom. “Maybe you need to start getting them on a regular basis.”

  “Maybe so…” I smiled and raised my bottom again.

  Even though he was mostly playing around, he still gave me a spanking that left my bottom stinging, burning, and sore when it was over. He stopped when it got to the point that I was almost in tears. The wetness between my legs was burning as hot as my bottom when he was done. I crawled off of his knee and he climbed on the bed behind me, holding my hips as he positioned his cock against my pussy.

  “This is what you really want, isn’t it?” He pushed it in a couple of inches.

  “Yes.” I nodded enthusiastically.

  He held me face down on the bed and started to drive his cock into my wetness. I was so hot for him after waiting so long, playing with myself, and spending time over his knee, that I couldn’t hold on very long. I had my first orgasm, clenching his cock as I spasmed, before he really got going. He picked up the pace, using the increased lubrication of my orgasm to pound me even harder than normal. His cock started to throb and pulsate inside of me, sending me dangerously close to another one as he continued to thrust.

  “You feel so good…” He grunted as he hammered his cock into me.

  It didn’t take as long as normal for either of us. I could tell he was close as his thrusts became more erratic and lingered deep inside of me. He leaned over me and started to drive himself in harder. I could feel his cock throbbing and then I felt the surge of his cum when he let out a growl. He unloaded inside of me, withdrawing and driving it in deep for another hard ejaculation that was even more powerful than the first. My body reacted by squeezing his cock as another orgasm started to form inside of me, causing my body to shake and spasm when it was finally released. He stayed inside of me for a bit after he was done, just slowly grinding his cock until his lust slowly started to subside.

  “I’m going to have to make an honest woman out of you…” He sank into the mattress beside me and pulled me close.

  “You just decided that now?” I smiled and looked up at him.

  “Well I don’t want any bastard kids…” He laughed and I narrowed my eyes at him.

  Epilogue

  John seemed to know I was pregnant even before I did. A couple of days later, he returned from town with a ring that fit my finger perfectly. I knew I was pregnant by the time the preacher came out to the farm and married us in front of several townsfolk. Sheriff Boyd was his best man, and Colt walked me down the aisle. His limp didn’t slow him down at all as he escorted me to my future husband. I took his hand and we said our vows, ready to begin our life together as husband and wife.

  “You may kiss the bride.” The preacher said.

  John took me in his arms and dipped me down as he leaned in for a kiss. It was a long one that caused an eruption of cheers from the people in attendance. I wished my parents could have been there to see me on the happiest day of my life, but I knew they were looking down from heaven. My father would have been proud of the way the farm was being run and my mother would have been happy to know I had finally found someone who made me as happy as my father made her.

  ***

  “It’s a boy!” The doctor held up our son and welcomed him to the world.

  “So, we are going with Caleb for the name, right?” I winked at John.

  “Like hell…” He squeezed my hand and glared at me.

  We settled on the name Colt Boyd Bradford, honoring those that were instrumental in keeping us together during our darkest time. I insisted on Boyd as the middle name when I found out Sheriff Boyd’s first name was Larry. Boyd had a much nicer ring to it. I didn’t want our son to grow up without siblings, so we were hard at work on a second child when the next winter came and the crops went to sleep for the season. It didn’t happen that year, but I was sure we would have lots of opportunities to keep working on it.

  The diapers and the enemas were gone from our lives, but I still dressed up as his Little Jessy often. The dress that barely hung past my bottom was a clear indication to him that I needed to go over his knee for a little bit before he spread my legs and slid inside of me. By the following winter, I was pregnant with our second child and Colt was already becoming a bit of handful on his own.

  The farm was doing so well that John didn’t have to do much in the fields, and people were coming from further away to negotiate prices once we started planting more crops and raising more livestock. The small Cartwright Farm that only made enough money to keep us fed in my father’s time was transformed into the much larger Bradford Ranch. I couldn’t wait to grow old there with my husband and my children.

  The End

  Bonus Content: Little Penny & The Convict

  When I got the news that my father had passed away, I was absolutely heartbroken. He had been a shell of a man after my mother passed two years prior, so I guess it didn’t surprise me. With the phone in my hand, I slipped down against the wall and bawled my baby blues out. I was all alone in the world—an orphan at twenty-five. My life had been absolute chaos after my mother passed, and his passing just brought me further into the despair I had been teetering on the edge of. He was my rock for so long, and I was always a daddy’s girl. After my mother passed, I tried to be there for him, but living two hours away and trying to maintain a budding career made my trips home less frequent than I had hoped. I called him every single day, and I could always sense the sadness in his voice. I asked him over and over if he wanted me to come home and he always told me no. He said he would be okay, but I guess that was a lie. I’m almost positive he died of a true broken heart. My mother was his soul mate.

  Being an only child, I had to come home and make the arrangements. No child should have to bury both of their parents before they are thirty, and they certainly shouldn’t have to bury them within such a short span of time. The funeral was as beautiful as I could make it with my meager salary. I knew there was a life insurance policy, and he hadn’t even spent what he got for my mother. It was a considerable sum of money, so I decided that I was just going to take some time off from work. I was a mess, and the thought of trying to be friendly for eight hours a day was horrifying. All of his friends and the remaining members of my extended family came to the ceremony. They said it was beautiful and I did a great job. Of course, they promised to be there for me if I needed them, but within a few weeks, they were back to ignoring me like they had done all my life. I was okay with that, because what I really wanted to do was sit in the dark, drinking wine and smoking cigarettes. When I did eat, I ordered a pizza and chewed on it for a few days.

  After a couple of months, I was mostly just a recluse. The two insurance policies were enough to keep me out of work for a long time since I wasn’t really spending them on anything but cheap toxins to slurp, inhale and eat. I knew I needed to pick myself up off the floor and try to move forward, but there was just on drive left in me. Some days I barely got out of bed. I bought what I could in bulk because I didn’t even want to leave the house. I didn’t shave anything, I hardly bathed, and even though I knew I smelled like shit, I didn’t care. I pictured myself growing old and dying in that very spot, just like them. The family line could end with me for all I cared, because I didn’t have any interest in trying to mingle with other humans. I did want comfort, but finding comfort was such a long and arduous road filled with pretending. Even if I invested the time, I might just find an asshole that used me until he was ready to move onto someone else—that had been my experience with the dating scene since college at least.

  One day I wandered out of my abode for the usual monthly stocking of various items. I had been flirting with the idea of just buying some fro
zen dinners in bulk to avoid even having to deal with the social interaction of the pizza delivery guy, so I hit up a Sam’s Club and started stocking. As I was pushing my cart through the store, I caught sight of a man that instantly sent me into a mental tailspin. I knew him, and I knew him well. He was my old neighbor, Edward Watson. I didn’t know when he moved away exactly. It was sometime while I was in college. Memories immediately flashed in my head, and I remembered one of the craziest events from my past. During the summer after I turned eighteen, I was still in rebellion mode, and I loved to sneak out at night so I could smoke cigarettes on the back porch. I’m fairly confident my parents knew, but they didn’t want to confront me about it. Every night it was the same ritual, but one night I witnessed something extremely bizarre.

  There was a noise coming from his house, and one I couldn’t really place. It sounded like whimpering, followed by the sound of skin being slapped. I was intrigued and worried, so I crept over to his house and peeked in his window. I couldn’t see much, but I could see a line of his living room through his curtain. Mr. Watson had his latest girlfriend—and they were usually a revolving door—over his knee spanking her. I couldn’t tell if she was into it or not, but that wasn’t the strangest part. What caught my attention was what she was wearing. She was dressed in a one-piece pajama suit that had a flap in the back. The flap was down and her bottom was glowing red underneath his hand. Her hair was tied in two pigtails and when she looked back at him, I saw she was sucking on a pacifier. I stood there and watched them for nearly thirty minutes before I decided I should get back inside my house. The last thing I saw was him fasten the flap back on her waist and hug her while she cried on his shoulder.

  It wasn’t the only time I spied on them. After that, I spied on them nearly every night. Sometimes she would be wearing those pajamas, sometimes she would be wearing cute dresses that looked like they were made for a child, and sometimes she would be completely naked except for a diaper! I never saw any sort of sexual contact between them; it was like they were roleplaying some sort of daddy-daughter thing. He took care of her and she was always happy and smiling if she wasn’t getting spanked. I wasn’t sure if she was getting spanked because she had been naughty or if it was just part of the experience, but I often found myself dressing in loose pants so I could push my hand in them and pleasure myself to the sight of her over his knee. He was so incredibly attractive, and she was so beautiful that it was like watching some strange celebrity movie. One day, I found the house dark, and then I never saw her again. A few times I saw him drinking in the living room, but that was it. The lights stayed out, she never returned, and he moved away at some point while I was gone. Somehow, I managed to suppress that memory until I saw him picking out groceries an aisle over from me. As much as I hated human contact, I wanted to talk to him.

  “Mr. Watson?” I pushed my buggy down the aisle. It was packed with a case of wine and a bunch of pizzas by that point—the tobacco aisle was going to be my final stop.

  “Um, hello?” He stood up holding can of ravioli and adjusted his glasses to look at me. “Do I know you?”

  “You used to, yeah. I lived next door to you…” My voice trailed off, and he instantly put the pieces together.

  “Oh my goodness. Is that little Penny Reynolds all grown up?” He smiled and shook his head. “Wow, I haven’t seen you in a long time.”

  “Yeah, I saw you over here so I thought I would say hello.” I started pushing my buggy past him. It was hard to believe the awkwardly shy man standing in front of me was the same one I watched so many times.

  “How are your parents? I’m ashamed to say I haven’t kept in touch even though your Dad used to invite me over all the time.” He dropped the can in his buggy and pushed his alongside mine, matching my stride.

  “They both passed away.” My voice took on a somber tone the minute I was forced to say it out loud.

  “Oh no! Was there an accident? I don’t keep up with the news much.” He stopped his buggy and looked at me with a stare of concern.

  “No, nothing like that… My mother passed away a couple of years ago, and my father passed away just a few months ago.” I stopped my own buggy since he seemed interested in talking. For some reason, it actually felt nice to have some human conversation, despite the fact I had shied away from it since my father’s death.

  “I’m so sorry, Penny. I had no idea. I wish I would have known…” He shook his head sadly. “Are you staying in your old house? Didn’t you move away?”

  “I did, but I’m back now. Sadly, I haven’t been able to let go of everything yet.” I felt tears and I wanted to get out of there before they started. “It was good seeing you.”

  “Can I stop by some time? I know I wasn’t much of a neighbor to you, but I did like your parents. Maybe we can…” He looked in my buggy. “…have a drink and talk about the old days.”

  The old days I remembered weren’t exactly open for discussion, but I found myself agreeing. He did seem genuinely sad to hear the news about my parents, and he did know them for a very long time. I didn’t expect him to actually show up. I figured his words were just like the ones I had heard from my family members who said they would be stopping by every week to make sure I was okay, and I hadn’t seen a single one of them in over a month. I finished my shopping and went home. I wasn’t really hungry, so I popped the cork on a new bottle of wine and lit up a cigarette. The television was still on so I sat in front of it like the zombie I had become. After finishing the bottle, I slumped over onto the couch, which had become my bed, and drifted off to sleep. That night I dreamed about what I had seen with I was younger. Seeing him in person made them real again, and I woke up in the middle of her red, bouncing bottom. My panties were saturated and I pushed them down. For the first time since my father passed, I started to touch myself.

  There was a lot of bottled up unreleased sexual energy inside of me. My finger started to rub my clitoris and my pussy just continued to produce more and more slippery juice. I pushed a finger inside and finger-fucked myself for several minutes before moving back to my clitoris and circling it with my saturated finger. I was surprised at how quickly I got close to the edge of an orgasm. Usually masturbating was a twenty or thirty minute ordeal of pleasure, but after ten minutes, I was moments from cumming. I moved my finger back down my labia and stroked my pussy, trying to prolong the experience. It had been so long that I felt an overwhelming desire to enjoy it for a little bit. I rubbed around my vaginal cavity, then finally pushed my fingers back inside. After a few minutes, I couldn’t stand it any longer so I rubbed my clitoris until I felt my body quivering and tightening. The orgasm was one of the most powerful ones I could ever remember, and rivaled the naughty ones I had watching Mr. Watson and his little plaything. When I was done, I was absolutely exhausted, but brimming with a new energy.

  When the knock came at the door, I shot up on the couch like a rocket. I had no idea who it could be. I was fairly certain it was a family member, and I didn’t care if they saw the mess. I pulled my panties up, slid my jeans back into place, and threw a blanket over the wet spot I had created. The smell of booze and cigarettes was enough to cover anything I had left behind. I walked over to the door and looked through the peephole—I almost crumbled into a pile of confusion right there because the eye staring back at me was Mr. Watson. I walked in a circle with my hand in my tangled hair. What the hell was he doing there? Of course I invited him, but I didn’t expect him to even show up. The house was an absolute disaster—I was an absolute disaster. My legs were already turned to jelly from the orgasm, so I could barely even walk. I finally just relented and opened the door. I had seen his secret, so I decided to show him mine.

  “Hello Penny, I hope I didn’t wake you. I thought about you when I got home last night, and I really just wanted to make sure you were okay.” He had a warm smile.

  “Come on in, Mr. Edwards.” I pushed the door open. “I’m really sorry about the mess.”

  “
Oh it is okay—” He couldn’t even finish that sentence when he saw how bad it actually was. “Wow.”

  “I know. I’m a freaking slob.” I walked to the couch and plopped down, lighting a cigarette. It would have probably been customary to ask if he cared, but the thick smell of burnt tobacco was a permanent fixture in the house, so it wasn’t going to add anything to the toxic atmosphere he had already stepped into.”

  “I brought a bottle of wine. I saw you had plenty, but this one is a little better than what you’re used to.” He placed it on the counter next to several empty ones.

  “Thank you… There are some clean glasses—well, I can clean some up.” I looked around and grabbed a couple of used ones.

  “Penny, isn’t it a little early? It is ten in the morning!” He seemed confused that I was offering him a drink, but it was already late for me to start.

  “Don’t worry about it. Time is just a function of life.” I smiled and cleaned the glasses. He popped the cork and we sat down with our glasses. He actually sat on the couch which made me nervous, because he was sitting right on my big puddle of cum. Thankfully, I did throw a blanket over it.

  “You don’t look well.” He said as he sipped his glass. “I noticed it yesterday, but I see so much sadness in your eyes.”

  “Thanks, I invited you over so you could tell me I look like shit.” I actually smiled at it. He was still so damn awkward, which didn’t fit the motif of the man I had seen so many years before.

  “I didn’t mean it like that; I just mean that you clearly aren’t getting past what happened with your parents. I have a friend who deals with this sort of loss. I could get you an appointment.” He sipped his glass again and then reached into his pocket. He pulled out a cigar and motioned to ask if I minded—I certainly couldn’t argue with a burning cigarette pressed between my fingers.