Becoming Little Jenny (A Dark Age Play Romance) (My Little World Book 2)

by Becca Little

  “My bottom still hurts from yesterday!” She said as he sat down and took her by the wrist.

  “Don’t be ridiculous.” He shook his head. “I didn’t spank you that hard.”

  It was a white lie, of course. The spanking had certainly hurt when it was administered, but she didn’t feel anything by that point. He took her across his knee and slid her pajamas down, exposing her bottom. The bedtime spanking began with several hard smacks and she wrapped her fingers around her quilt, holding on tight as she was punished. Once the spanking started to really sting, she silently vowed to do better the next day and avoid ending up across his knee before bed.

  “I’m really sorry, Daddy.” She whimpered as his hand continued to fall.

  “What are you sorry for?” He asked.

  “I’m sorry that I didn’t work harder.” She held the quilt tightly in her hand, forcing the words out between a grimace.

  The spanking was methodical, moving from one side of her bottom to the other in rapid fashion. His hand would come down in the same spot a couple of times, but he mostly alternated unless he was delivering one of his very painful smacks in the middle which stretched across her whole bottom. He tilted his knee and kept her bottom in the air, refusing to let her slide off his knee when she got dangerously close to doing just that. The tears started to appear in the corner of her eyes again.

  “I only want the best for you.” He stated firmly. “I’m spanking you so there is a little more motivation tomorrow when you realize you haven’t completed all four assignments.”

  “Four more tomorrow?” She groaned.

  “You can do four in one day.” He replied. “Even if there is some reading to do between them.”

  “Yes sir…” She whined.

  It wasn’t an impossible request. Jenny could have done it if she hadn’t gotten so sidetracked during the day. It would be her mission going forward. She didn’t want to disappoint him, especially when her bottom was on the line every day if she didn’t do what he asked. The spanking continued and his hand started to fall harder—much harder than it had the previous day. She couldn’t fight the desire to try and stop him, so she threw her hand back.

  “That’s too hard!” She squealed, tears streaming down her face.

  “You said your bottom was still sore today and I know that was a lie.” He took her wrist in his hand and pinned her arm to the small of her back. “Tomorrow, you won’t have to lie.”

  “Daddy, I’m sorry! I didn’t mean to lie!” She squealed and squirmed in his grasp.

  “Liars go to bed with very sore bottoms.” He said firmly.

  Jenny soon learned that her Daddy considered her lie a very serious offense and it wasn’t as harmless as she thought when the words passed her lips. He turned her bottom redder than ever before he started to finally slow down. The spanking had been a lot harder and a lot longer than the previous night. She wasn’t sure she could even focus on sleep at that point when he cradled her in his arms once it was over. She cried a lot harder than she had the previous night with her head pressed to his collar.

  “Never lie to me, Jenny.” He said as he rubbed her hair.

  “I’m sorry, Daddy.” She whispered through her tears. “Never again.”

  He held her a lot longer than he had the night before and she let go of her emotions while she was cradled in his arms. There was something about them that seemed safe and each time she was there, she felt more and more attracted to him. He was her Daddy, but she realized he was so much more. He was one of the most eligible bachelors in the world, a man that women fantasized about, and she was in his arms. He had chosen her to be his little girl. He had chosen her to be the one he protected. Jenny felt very special, even as she crawled into bed with a sore bottom.

  “Tomorrow will be a better day, Daddy.” She whispered as he walked to the door.

  “I hope so. I’ll see you extra early—don’t forget.” He flipped off the lights and closed the door.

  Jenny stared into the darkness, the covered forming an outline around her well-spanked bottom. It was even redder than the night before and she was sure she would feel it in the morning. It would serve as a constant reminder all day long while she did her schoolwork. She was determined to make the next day better and avoid going over his knee before bed. She had a lot of work to do, but she was even more motivated than she had been the day before. She drifted off to sleep with nothing but thoughts of being his good little girl running through her head.

  CHAPTER 13: JENNY IN DIAPERS

  “It’s time to get up, Jenny.” Daddy’s voice roused her from her slumber.

  “It’s so early.” Jenny rolled over and immediately grimaced when she felt her bottom on the mattress.

  “Yes.” He said as he took her by the hand. “It’s early for me too.”

  Jenny was led into the bathroom where she saw a tub already running with water. Daddy dumped some bubble bath into it and suds started to form. He started to undress her and she didn’t resist. She was getting more comfortable around him, so she didn’t try to hide her nakedness. When she was totally exposed for the first time, he took a moment to admire her body, turning her around so he could see her bottom, which was still pink from the night before. He reached over and turned off the water before turning back to her.

  “You’re very pretty.” He said as pushed the hair out of her eyes.

  “Thank you…” She blushed and looked down at the floor.

  He took her to the tub and helped her inside. When he said he was going to bathe her, she expected it to be humiliating, but it was quite nice to have his hands on her body. He lightly scrubbed her from head to toe with a washcloth and then a bath brush that had a long wooden handle. When he got close to her pussy, he avoided it for the most part, which sent some tingles of desire through her whole body and made her feel slightly aroused. After she was soaped up, he picked up a bottle of shampoo and washed her hair, leaving it soapy and clicked back on her head.

  “Sit on this towel.” He put a folded on one the edge of the tub and another on the floor.

  “What are you going to do?” She asked as he helped her out of the water.

  “I’m going to shave you.” He said, reaching for a razor.

  She was caught between fear and curiosity when he started to lather up her legs. He quickly made the hair disappear and then he pushed her legs apart. She knew what was coming even before he started applying the shaving cream to her pubic hair. She let him open her legs and lather every inch of her inner thigh and her labia. The razor shaved her bald in a matter of minutes, leaving no hair behind at all. When he was done, he helped her back into the water and picked up the washcloth.

  “Okay, let’s get you good and clean.” He ran the cloth along her freshly shaved legs.

  Jenny pushed her hips forward when he started to move up her inner thigh. She was anxious to feel his touch after getting aroused, even if it wasn’t skin on skin. He rubbed her pussy with a careful touch, washing away the last bit of shaving cream. By the time he was done, she was on fire with desire for something more than just the touch of his hand. She let out a sigh when he took his hand away and started to drain the tub. The suds went down and he helped her up, starting the shower.

  “That was so nice…” She said as she stepped into the shower. “You could join me if you wanted.”

  “It isn’t about what I want.” He replied. “This experience is to help you. If you want me to join you, I will.”

  “I do.” She nodded as she stared at him.

  Daddy stripped off his t-shirt and her head spun as she stared at his amazingly hot body. Her eyes followed his muscular arms down to his hips where he started to unfasten his pants. They hit the floor and he was dressed in nothing but his boxers. When he pushed his hand into the waistband of those, her eyes were ready for the grand reveal—she wasn’t disappointed. He had a cock like a sledgehammer hanging on top of a large set of balls. He stepped into the shower and pulled the curtain closed.<
br />
  “Can I wash you?” She asked.

  “If you want.” He nodded.

  Jenny lathered up the washcloth and started moving it across his torso. Her pussy was getting so wet the shower couldn’t even remove her excitement. She focused on the upper torso and then his back, admiring his form. She had never been with a man so well built or so handsome. She certainly had never been with a man that had a cock like his. Just looking at it made her wild with the thoughts of having it inside of her. After she washed his back, she moved down his ass and then his legs, lifting between his thighs.

  “I think this needs a little more than soap.” She said as she moved her hands towards his cock.

  “You can clean it however you want.” He said as she ran a fingernail down the edge of his balls.

  She pushed him back out of the water and knelt in front of him. Her lips started to kiss his thighs and his cock started to get hard. She opened her mouth and extended her tongue, tasting him for the first time. Once his cock was fully engorged with his desire, she started licking along the bottom and swirled her tongue around the head. It was enormous and so thick she struggled to get her whole hand around it. Her lips kissed the side and then she opened her mouth to slide it inside.

  “Are you sure you want to give yourself to me like this?” He asked. “Once you go down this road, there is no going back. I will claim you and I will use you for my pleasure whenever I want.”

  “You already claimed me.” She said with a smile. “Now I’m claiming you.”

  Her mouth opened wide and his cock slid between her lips. She massaged the bottom of it with her tongue and worked it further into her mouth. It was so thick she struggled, but after working on it for a few minutes, she could get half of it down her throat. She couldn’t believe she was sucking a billionaire’s cock, a man who could have any woman in the world with one quick snap of her fingers. She was claiming him and his enormous cock as her own, and she didn’t care what that meant outside of that moment.

  “That feels really good.” He let out a moan. “You’re being a very good girl.”

  Hearing his praise was a motivator for Jenny. She started pulling his cock in deeper, massaging it more and more until his whole cock was almost in her throat. She pushed past the barrier and he slid deeper than any man had been before. Her throat muscles hurt from his girth, but she was determined to please him. She started working on his cock furiously, pulling it in and out of her throat, letting it rest on her tongue for a quick massage before she pushed towards his pelvis again. Her lips met his pubic hair and she pulled back until she was almost to the tip of his cock, immediately pushing it in again.

  “So good...” He put his hand on the wall and braced himself. “You’re going to make your Daddy cum.”

  Jenny picked up the pace hearing his words, but she could already feel it. His shaft was throbbing and the head of his cock was becoming even more engorged when it smashed into the back of her throat. A few seconds later she felt the first stream of cum erupting into her throat. She swallowed, forcing the drops of cum down her throat as he unloaded in her mouth. The grunts came faster as he continued to ejaculate long streams of his lust in her mouth. When he was finally done and every drop had been swallowed, he sank back against the wall and sighed.

  “I picked a very good girl…” He put his hand on her head.

  Jenny cleaned his cock and then the shower was turned off. Daddy dried her off first and then dried himself. He used a hairdryer until her hair was dry and then tied it into two long brown pigtails. Once that was done, he leaned in and nibbled on her neck for a moment before taking her hand. She followed him down the hallway and he pushed the door open to a new room, one that she hadn’t seen the inside of since she moved in. Inside of the room was a crib, a large table, and several packs of diapers stacked in the corner of the room.

  “What is this?” She looked around with a strange curiosity.

  “Since you got so distracted yesterday, you’re going to be able to sit in one spot all day without interruption.” He took her to the table and scooped her up.

  “I don’t understand…” She looked up at him.

  “You’ll see.” He spread her legs and started applying baby powder to her pussy, which was burning with desire after what she had done for him.

  Jenny felt like a child in his hands as he powdered her and then pulled a diaper from one of the packets. She had no memory of ever wearing one but the smell brought back memories she couldn’t quite place. It was a strange sense of calmness mixed with the aroma, as if her brain was reconnecting with something she had lost years before. He slid the diaper around her waist and pulled the Velcro tight before fastening it. Once she was done, she looked down at it with uncertainty in her eyes.

  “I’m not sure about this…” She stated.

  “You’re my little girl.” He said as he helped her up. “Sometimes that requires regression to the earliest incarnation of your life to help you succeed.”

  “So, I just…use these?” She asked.

  “Yes. You have no reason to get distracted.” He patted her head. “Let’s find a dress for you.”

  He took her hand in his and she waddled back to her bedroom. The diaper felt strange, but the baby powder kept the diaper from rubbing on her sensitive areas. Daddy picked out a beautiful dress and she put it on. The diaper was hardly visible underneath it, but she knew it was there. They ate breakfast together and then he left for the day. Jenny walked back to the living room and sat down in front of her computer with Mr. Fluffy after the kitchen was clean and she had made a cup of tea.

  “Okay.” She said firmly. “I’m going to do this today.”

  There was a new energy in Jenny as she worked. Her fingers danced across the keyboard. She was still feeling that strong need for relief between her legs, but knowing she had pleased her Daddy helped motivate her to be better for him. She finished her work a couple of hours before he got home and even had time to sneak in a quick nap. When he came through the door, she couldn’t wait to show him all of the work she had done.

  “Daddy!” She said happily when he entered.

  “Hey, you are certainly happy.” He smiled.

  “I got all of my assignments finished!” She exclaimed, practically dancing on her toes.

  They sat together on the couch and she showed him all of her assignments, brimming with enthusiasm each time. Daddy wrapped his arm around Jenny and held her tight while they reviewed each assignment. After they were done reviewing the assignments, he made dinner and they ate together. Jenny was brimming with energy, just so excited to have his praise and admiration instead of having him come home and immediately decide she needed to go to bed with a sore bottom. She hoped those days were behind her, at least for a little bit.

  CHAPTER 14: TAKING LITTLE JENNY

  For the next few days, Jenny did everything right. She got bathed, showered with her Daddy, and swallowed his cum. After that, she worked on her schoolwork until she was done, and then when her Daddy came home, they had dinner together. Her bottom had healed and the last spanking was completely forgotten. She still helped herself to caffeine in the morning, but she was no longer needing a cigarette every time she drew a breath. It seemed that her Daddy had also given up his cigars, at least when she was awake. Things seemed to be moving at a good pace, but she was still concerned that they hadn’t had sex.

  “Daddy…” She said as she sat up in bed on Saturday morning.

  “Yes, darling?” Daddy asked.

  “When you first let me move in here, we talked about a lot of things…” She began slowly.

  “I don’t like hints, just tell me what you’re trying to say.” He looked over at her.

  “I thought we were spending a lot of time getting to know each other, and you said I belonged to you—in every way.” She stated.

  “You do.” He nodded. “You are my Little Jenny.”

  “We still haven’t done anything…” She said. “I thought that meant
we would do more than just fool around in the shower.”

  “What do you want?” He turned towards her.

  “I mean…” She stammered over her words.

  “Tell me what you want and you’ll get it.” He said, almost interrupting her.

  Jenny had no idea how to ask for sex. It was never something she had to initiate. She was normally the one saying no when a hand was moving under her skirt. The times she didn’t say no, she normally woke up with a hangover and a lot of regrets. She knew what she wanted with her Daddy, but finding the words without a little liquid courage in her veins was especially difficult. She took a deep breath and searched around in her head for the right thing to say.

  “I want you.” She said after a brief hesitation.

  “Then you’ll have me.” He took her by the hand and moved closer.

  In an instant, his lips were pressed against her neck. She sighed as he started getting turned on. He slid his hands underneath her pajama top and caressed her breasts while his lips moved to her ear. It was so simple, yet she had struggled to find the right words. Once they were said, he took control of the situation. For the first time since moving in with her new Daddy, she felt like she had a little power. She could command his attention with her words, although she knew it was a dangerous game to push her luck. He could have had her at any time, but he made her ask for it.

  “This is what you wanted?” He asked as he moved to her lips and kissed her.

  “Yes.” She whispered when their lips finally parted for a moment.

  Once the words were said there was no turning back. He stripped her pajama top off and eagerly kissed her breasts, taking one nipple between his teeth and then the other. They started getting hard between his lips and he pushed her back on the bed, sliding his fingers into her pajama bottoms. They came off quickly, landing on the floor beside the bed. She was thankful she didn’t have to wear a diaper to bed. She spread her legs open as an invitation and he started removing his clothes. She leaned forward and assisted with pulling his t-shirt over his head.