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

by Becca Little

  “I’m so glad you’re here, Jenny.” He said in a soft whisper. “I’m going to take good care of you.”

  “Thank you, Daddy.” She said in response, even though the words felt fairly forced. After that, he was gone. Sleep came quickly as she lay in the silence of the night.

  CHAPTER 8: STARTING OVER

  Jenny’s eyes opened and she had to sit up straight at first. It took a few minutes to remember exactly where she was, why her hair was in pigtails, and why she was wearing pajamas that looked like they belonged on a little girl. The realization finally settled in and she sat up. It was her first day as Damien’s Little Jenny. He was her new Daddy. She struggled with the idea and wondered if it was the right decision. Everything he said made so much sense. The moment her life changed was when she found out her father had died. She had been nervous that when he came home from his trip and saw her report card, she was going to be in a lot of trouble. Instead of him at the door, it was a man with a badge. Her mother collapsed on the spot and their world was shattered.

  As the memories flooded in, her door opened and her new Daddy walked in. He was dressed in a blue button-down shirt that was unbuttoned all the way revealing an undershirt that seemed one size to small as it struggled to contain his bulging chest. His pants were black and held up by a thick leather belt. She remembered what he told her and knew she was going to start her rebirth. She would get to go back to the moment she lost and start over as if it never happened. She looked up at him as he folded his arms and leaned against the frame. There was a look of disappointment on his face. She wasn’t sure what she had done wrong.

  “Good morning, Daddy. Is something wrong?” She wondered if he had changed his mind and no longer wanted to go through with it. She thought she would be the one questioning it, not him.

  “You tell me, Jenny.” He walked in and closed the door, holding out a piece of paper.

  Jenny recognized the paper. It was her report card, the one she had dreaded her father seeing. She had no idea how Damien even found it. It had to be buried in her things somewhere, but it must have taken a lot of work to find it. She held it in her hands and moved her fingers across the aged ink, tracing the grade she feared most, a F in math. Her father was gifted in math, and he tried to tutor her every weekend, but his job often took him away. She came to depend on the tutoring and when it wasn’t freely available, she struggled to keep up.

  “Where did you find this?” She asked as she stared at it.

  “It was on the counter. I’m sure your mother left it there for me to see when I got back from my trip. I’m very disappointed in you, Jenny.” He tilted his head and flexed his jaw muscles.

  Jenny began to realize what he meant when he said starting over. It wasn’t just an expression, it was literal. He expected her to go back to that moment and relive the experience, with a different outcome. She wondered if that was even possible. She knew it was the moment her world collapsed, but she wasn’t sure how going back to it could change anything. The only thing it would bring was bad memories, memories she tried to suppress. She fought to maintain the character he had laid out for her. She was Jenny, she was his little girl. He was her Daddy—not her father—he was something more. That was the expectation and she didn’t want to disappoint him.

  “I’m sorry, Daddy.” She placed the report card back in his hands.

  “Why didn’t you study more, Jenny? If you knew your grade was in trouble, you should have spent every day working on problems and practicing. I bet you spent most afternoons at home in front of the television and barely cracked the book.” Her new Daddy sat down beside her.

  That part was true. She knew it was the reason she failed, but she kept thinking everything would be okay with a tutoring session. When her father’s job took him away, she let that be an excuse, but it really wasn’t a good one. She knew that now, even if she didn’t recognize it back then. She struggled to find the right words, but the only thing that came out was another apology.

  “I’m really sorry. I’ll do better next time.” She felt exactly like she did back then, defeated and weak.

  “I’m going to help you. We’ll spend all weekend working on this and make sure you are caught up and able to put this behind you. The next time you take a test, you’ll get an A.” He put his arm around her.

  “Thank you.” Jenny smiled and snuggled against him. He smelled like a freshly smoked cigar, but she didn’t care. Her blood was begging for nicotine and even the second-hand aroma was something. His loving touch was one she hadn’t felt since she was a child.

  “But first we have to deal with the grade you earned. This is unacceptable.” Daddy removed his arm from around her shoulders.

  “What do you mean?” Jenny asked.

  “I’m going to have to punish you, Jenny.” Daddy looked her in the eyes.

  Jenny’s eyes got big. Daddy’s contract had mentioned discipline was part of the process, but she didn’t expect to be on the receiving end of it the very first day, especially for something she did years before.

  “No, I…” She tried to process what he was saying.

  “Did you really think I was going to let you bring home an F and not punish you?” Daddy tilted his head and stared at her again.

  Jenny fully understood what starting over really meant. Not only was he going to take her back to the moments when she made terrible mistakes and bad choices, he intended to punish her for them. There were an awful lot of bad things in her closet, and that could mean quite a bit of punishment. She had to trust him. He said he had done this before, rebuilt others before her. If he could give her a chance to start over and wash away the mistakes, then maybe it wouldn’t be so bad after all. She nodded in understanding.

  “Roll up my sleeve.” Daddy said, presenting his right hand to her.

  Jenny’s heart beat as she reached out and caressed his shirt, then found the button. She pushed it through the hole and folded the silk fabric backwards. She pushed it up his muscular arm and folded it neatly, creating a seamless roll right below his elbow. As soon as she did, he took her by the arm and guided her across his knee. Once she was in position, her bottom was in the air and she felt like a little girl again, being put over Daddy’s knee for a spanking. They weren’t uncommon in her household, but she hadn’t had one since her father passed. Her mother believed screaming and grounding got the job done a lot better than corporal punishment.

  “I know it has been a while since you’ve had a spanking, Jenny, but I’m not going to go easy on you. You need to understand the importance of school and bad grades will not be tolerated.” Daddy placed his hand on the seat of her pajamas.

  Jenny flinched involuntarily from his touch. “Yes, Daddy. I understand.”

  With that, Daddy brought his hand down with a resounding smack. Jenny immediately flinched from the impact more than the pain. Her body was quivering with fear. She felt just like the little girl over Daddy’s knee when she was a child, and in many ways, that was exactly what was happening to her now as she assumed that role again. He was serious about not going easy on her. His hand came down again and again. It started in the center, and then moved to the left and the right. As it kept coming down, it got harder and started to hurt. Jenny tensed up; knowing that the worst hadn’t even began yet. Despite the pain, she began to realize that a spanking was exactly what needed. It had been missing from her life for far too long.

  “Oww.” She whimpered as his hand found his favorite spot, right in the center of her bottom, which had become rather tender.

  “Are you going to put your full attention on studying instead of television?” Daddy asked as he moved his hand to the right side of her bottom and landed several hard smacks before moving to the left and giving it the same treatment.

  “Yes sir!” She sniffled and grimaced. Her bottom was starting to sting.

  “Good girl.” The pattern continued with several hard smacks on each side of her bottom followed by one in the middle

 
“Ouch.” As he repeated the pattern over and over, her bottom hurt more and more. She had forgotten just how much a spanking did hurt. For some reason, she thought that just went away as you became an adult and got tougher, but she didn’t feel very tough over Daddy’s knee.

  “Now.” He said as he continued spanking her. “I’m going to unbutton your pajamas and spank you on your bare bottom.”

  “No…” Jenny whined. Her father always saved the bare bottom spankings for when she had been extremely naughty.

  “Jenny, I said I wasn’t going to go easy on you. It is very important to me that you learn the importance of paying attention in school and putting in the extra time at home.” Daddy continued to bring his hand down on the seat of her pajamas, causing her bottom to sting.

  “I’m sorry; I promise I’ll do better.” She whimpered out one final plea as his hand paused.

  Jenny felt Daddy’s fingers on the buttons of her drop-seat pajamas. He unbuttoned the right one, then the left, pulling the fabric down to expose her panties. Panties were the only thing she didn’t find waiting for her in her room, so she was forced to wear a pair she brought with her. They had a black floral pattern set inside the hot pink fabric. They weren’t thongs, but they were very close. She really didn’t have many pairs she would want to be seen in public wearing unless she had something covering them.

  “Jenny, what is this?” Daddy asked, pulling the fabric of her panties back and letting it snap on her bottom.

  “I couldn’t find another pair.” She admitted.

  “Didn’t I tell you that everything you needed was in this room?” He asked in an angry tone.

  “Yes sir.” She nodded.

  “So, if you didn’t find any panties, what does that tell you?” He asked.

  “I don’t know?” Jenny realized that his tone was turning to one of aggravation, not quite as loving as it had been moments before.

  “It should tell you, Jenny, that you don’t need any panties.” He snapped the fabric and sighed deeply. “Take them off.”

  Jenny stood and started the process of removing the drop-seat pajamas. It would be the only way she could get the panties off. As she started unfastening it, she felt ashamed. Daddy stood up and watched her until she got an arm free, exposing the side of one breast. It was the first time she had been naked in front of him in any capacity and she didn’t feel very comfortable. It was almost as if he sensed her apprehension and he stood up.

  “When I come back, I expect to find a bare bottom ready for a good, hard spanking.” He shook his finger at her and left, closing the door.

  Jenny was relieved to have a little bit of privacy, but there was still an overwhelming fear in her stomach as she realized that once she did finally get the panties off her bare bottom would be spanked. She tried not to think about it too much. The pajamas hit the floor, followed by her panties, which she kicked under the bed. Not knowing how long Daddy would be gone, she quickly redressed herself without her panties, leaving the back of her pajamas open. She looked in the mirror and discovered that her bottom was a dark shade of pink. Sitting wasn’t comfortable, so she stood awkwardly in the middle of the room with her bottom facing away from the door.

  Daddy returned shortly after she was dressed and she looked up at him as he closed the door again. He didn’t look happy that the punishment was interrupted because she didn’t do what he said. He walked back towards the bed, taking her arm as he did. This time he yanked her across his lap, instead of guiding her, pushing the drop-seat pajamas open until her bare bottom was exposed and protruding from them. He took a moment to position her so that her bottom was in the air and vulnerable. She felt a coolness on her bottom from the air, but that was quickly replaced by the calloused hand as it was placed on her bottom.

  “When I tell you something, I expect you to do what I say.” He said as he brought his hand down hard on the center of her bottom.

  “Ouch! Yes sir!” The hard smack on her bottom made every hair on her body stand up.

  Daddy brought his hand down on her bottom several times in quick succession. He concentrated on the middle most of the time, but he ventured out to each side generously giving it a break, although the break just meant she got spanked in another tender spot. He continued spanking her until tears were forming in her eyes. Her bottom burned like it hadn’t burned in years. She twitched and moved, trying to avoid his hand, but each time she did, he found the right spot and delivered a sound smack.

  “Do you like having your bare bottom spanked?” Daddy asked.

  “Oww! No!” She wiggled her bottom, wishing she could rub some of the fire away.

  “So, you’re going to pay attention in school?” He asked as he continued to punish her with hard, painful smacks.

  “Yes sir!” Jenny felt tears overflow from her tear ducts and roll down her cheeks.

  “Good girl.” Daddy kept spanking as she lay limp across his knee and cried.

  The spanking continued for a little longer and then Jenny realized it had stopped. She kept sobbing, holding onto the bedspread with her hand. A few seconds later, she felt his hand rubbing her bottom. It was hot to his touch and hurt. She wiggled to pull it away but he held her tighter and rubbed it until the burning had started to subside a little. He finally released his grasp and patted her bottom a few times.

  “Okay, Jenny. I want you to stand in the corner and think about why I had to spank you. Once you’re done, I want you go to your desk and write me a letter thanking me for your spanking and explaining why you’ll never end up in this position again for bad grades.” Daddy allowed her to stand.

  Jenny stood and nodded to her Daddy. She walked to the corner, stepping gingerly to avoid any part of her bottom bouncing and sending more shock waves of pain resonating through her already sore bottom. She assumed the position in the corner and stood while he watched for a few minutes and then left. Jenny noticed a clock next to the bed and she watched as it turned the minutes slowly.

  When ten had passed, she walked to the desk and tried to sit. The wooden chair was cool to her bottom, but it still stung. It felt good, so she didn’t bother to button her pajama pants. She started a letter with ‘Dear Daddy’ and poured her heart out, explaining why she had made the bad grades and how foolish she had been. When it was all done, she felt a strong sense of relief wash over her. She folded the letter and headed downstairs to deliver it to her Daddy.

  CHAPTER 9: KINDNESS

  Jenny walked downstairs with her letter and handed it to Daddy. He motioned for her to sit down across from him in a chair while he sat on the couch and read it. After every few words, he would lift his cigar and make the end glow. He already had a drink poured, which Jenny thought was strange since it was so early in the morning. He wasn’t dressed for work at all. Jenny had a sneaking suspicion that he wasn’t going to work. As the smoke drifted over and entered her nostrils, her heart pounded. It was going to be a very difficult day without a cigarette, especially since she had been smoking so much recently.

  Dear Daddy,

  Thank you so much for showing me how important it is that I do well in school. I’m very sorry that I let you down. I promise that I will do everything I can to make it up to you, and with your help, I know that I will be able to get an A before the end of the year. You are a wonderful Daddy and I am thankful that you took the time to spank me. I know that you love me very much, and I will not disappoint you again. Please forgive me.

  Your little girl,

  Jenny

  PS: I’m sorry I misunderstood your instructions about my attire.

  She really wasn’t sure what to put in the letter, so she kept it brief and followed his instructions. The post script was her own idea, but she thought it fit. After he finished reading the letter, he folded it and placed it on the table. He looked up and studied her face for a moment. She had removed all makeup and her only flair was the two pigtails in her hair. She felt quite ugly without her makeup, but she didn’t find any in the room, so sh
e had to assume it was not part of the arrangement. Having him stare left her feeling nervous, like he was judging the package he bought. She hoped she gave the illusion he was looking for. She really didn’t want to be out the street after her first day.

  “Daddy has a surprise for you.” He said finally.

  “You do?” She hoped it wasn’t another teddy bear. It was a nice present, but she hoped a billionaire’s daughter got spoiled rotten. It would make the time go by quicker.

  Daddy opened his laptop, which was on the table in front of him. He turned it towards her and pushed it over. Jenny had to focus on it. Her contacts had not been removed the night before, and they weren’t as clear as she hoped. After reading for a few seconds, she realized it was some sort of application. She moved her finger on the touch pad and scrolled to the top where she saw that it was a school website. It was an application for college.

  “College?” Her eyes lit up. “You’re sending me to college?”

  “I’m sending you to school, Jenny. I picked the educational level that I thought fit you best. This is one of the top online universities in the world. It isn’t the same as taking traditional classes, and it requires a lot of work. I will expect you to spend at least ten hours a day watching lectures, studying, and working on your assignments. Do you understand?” He took a drink and puffed his cigar.

  “I do! Oh, my goodness, Daddy! Thank you so much!” Jenny was ecstatic. The years had revealed how badly she needed a college education.

  Jenny wished she could go to an actual campus, but she knew that wasn’t going to be possible with the current setup. What he offered was the next best thing. She knew that with the changing times, an online degree was as good as most traditional classes. Several interviewers asked her why she didn’t just go to school online when she told them she wasn’t pursuing a degree.