Jen Simmons turned to look at the little girl who had called her. Her large brown eyes were wet with unshed tears, while chubby paint-covered fingers dug into the fabric of her cotton smock.
“What’s wrong, Lily?” she asked, moving to kneel in front of the girl. Jen tilted her head. “Are you hurt?”
Lily shook her head, causing her brown pigtails to whip against her small shoulders. Her lower lip jutted out ever so slightly. Jen had to fight back a smile.
“Then what is it?” she prodded patiently.
Lily lifted her arm to show the underside of it to her teacher. In the crease of her elbow was a streak of sky blue paint.
Jen giggled lightly. “That’s a nice color on you,” she said.
The little girl’s frown deepened. “But it’s not on my fingers!”
“I can see that,” Jen said, thoroughly amused. “You have nice colors on your fingers too though.”
“Ms. Simmons, it’s finger paint!” Lily exclaimed, placing great emphasis on the last two words. “But now, it’s not on my fingers!”
“I’ll help you clean up soon,” Jen promised, gently turning the little girl around. She gestured to the easel the child had been working at. “Why don’t you finish your butterfly until clean-up time? The poor butterfly only has one wing!”
After mumbling something about how the “other wing is in the back,” Lily obeyed and went back to painting. Jen allowed a soft chuckle under her breath before surveying her small classroom of five-year-olds.
Jen loved being a kindergarten teacher. It wasn’t the most glamorous job by any means, but she adored children and genuinely enjoyed being around them. Her parents had been far from supportive of her choice of occupation, saying that she should get a more respectable career in the sciences like they both had. They still discouraged it but Jen figured that at twenty-four years old, she shouldn’t allow her parents to make her feel ashamed of her personal choices.
Jen watched the little rugrats around her. It was her favorite time of the day, art hour. Ms. Simmons’ kindergarten class spent the long morning hours going over math and reading but the afternoons were reserved for artistic expression and creativity. Some of the kids, like Lily, chose to paint. Others were drawing, coloring, or making shapes out of brightly colored clay.
It was her favorite part of the day for a few reasons. The biggest was that the children loved it. She loved their happy chatter and humming as they worked diligently on their projects. It was also the least trying part of the day. The children worked independently while she got to watch and relax. The final reason was that it was the last thing that her parents would have wanted her to be doing as a child. They didn’t allow her to spend a lot of time on drawing and painting, saying that it was a waste of time and that she ought to spend more time reading and studying.
Jen shook her head a bit, refusing to obsess over how controlling her parents had been when she was living with them. She needn’t worry about that any longer. She clapped her hands to get the kids’ attention. “Alright, class! It’s clean-up time!” She grinned as little hands and feet scrambled to get the room back in order.
She was living a great life. She had a job that she loved, though it certainly wasn’t easy. She had some difficult children and parents to deal with from time to time, but overall, her job was extremely fulfilling.
She also had great friends, and although her parents were a bit overbearing, she knew that they loved her.
Above all of that, she had an amazing boyfriend named Will.
She had met Will in college five years before. She had been getting her bachelor’s in biology like her parents had suggested while he had been studying to become an engineer. Jen immediately fell in love with Will. He always knew what to say to cheer her up or get her heart racing. He was extremely handsome, standing at five feet, ten inches. He wasn’t too tall but since she barely stood above five feet, he was tall enough to make her feel small and cherished.
About an hour later, Jen waved as the last of the children left with their guardians. She looked at her watch. School let out at 3:30 but she always ended up hanging around for at least an hour after that, chatting with parents about their children or meeting with other teachers. She sighed as she grabbed her bag off her desk and slung it over her shoulder before heading out the door.
Will didn’t get out for at least another hour. That gave her enough time to take the bus to their small apartment and change. Today wasn’t just any old Friday after all. She needed to look presentable.
She had just exited the school grounds when a figure in the distance caught her eye. Her heart skipped a beat and she broke into a sprint when she recognized him.
Will grinned widely and opened up his arms as his girlfriend of five years rushed toward him. He let out a chuckle when she flew into his chest and bent to press a tender kiss to her forehead.
“I thought you said you wouldn’t be able to get off early today!” Jen exclaimed when they pulled apart.
“I might have lied,” Will said mischievously. He pulled her to him again so he could whisper in her ear, “Happy anniversary.”
She beamed up at him. Although they had already greeted each other that morning, she definitely didn’t mind hearing those words again. “Happy anniversary,” she said happily, wrapping her arms around her boyfriend’s neck.
“Where do you want to go?” Jen asked as Will helped her into the passenger side of their car. He just kissed her, before shutting the passenger door and walking around to the driver’s side.
He put on his seatbelt and paused for a second, turning to grin at her. “I thought we would make it a surprise. I’d blindfold you, but I’d rather not make it look like I’m abducting a child.”
Jen pouted at that. Will was always making fun of how small and childlike she was. He claimed that he loved how cute and small she was though, so she was able to relish in it as well.
She looked down at her plain white blouse and knee-length purple skirt. “We aren’t going to stop at home then?” she asked. “I wanted to change out of my work clothes first.”
Will pulled out into the street before reaching one hand out and resting it on Jen’s knee. “You have little faith in me,” he said, although Jen could tell by his smirk that he was joking. “Everything will be taken care of. I grabbed a few of your favorite dresses for you to choose from. Besides,” he added before giving her a brief, appreciative glance, “you look beautiful.”
“But where will I change?” she asked, ignoring his compliment.
“Everything will be taken care of,” he repeated simply. He gave her knee a light warning tap. “Trust me, okay, angel? No more questions now. I’d hate to have to pull over and teach you a lesson in obedience on our anniversary.”
Jen blushed at the thought of being spanked on the side of the road. “Yes, sir,” she murmured.
About an hour later, Jen was donning a deep maroon gown that she had completely forgotten she had. She gave a little twirl in front of the mirror in their hotel room. She had assumed that they were just going out to a nice dinner, but Will had surprised her with a weekend away at a five-star hotel on the beach.
She looked at herself in the mirror. The dress was one of the most mature pieces of clothing she owned, but even this one had some childish qualities. While the bodice complemented her small, but full breasts, the skirt flared out at the waist and stopped at her knees, making it comparable to a little girl’s dress.
She squeaked when Will came up behind her to wrap his arms around her waist. He nipped lightly at her earlobe, making her giggle.
“You’re so cute, my little,” he whispered, nuzzling her cheek with his.
Jen’s grin widened. She loved it when Will called her that. Although Jen was twenty-four years old, it made her feel safe and treasured when her boyfriend treated her like a child.
Jen didn’t have the best childhood. Her parents were cold and strict, often forcing her to stay home and study instead of going out with friends. She was also the eldest of four children. As a result, Jen had to grow up at a young age in order to care for her younger siblings.
She put on a tough facade as a young adult, getting a job at a local bookstore in order to pay her way through college. The little inside her longed to be coddled and cared for, however.
Will saw through her shell not long after meeting her in their sophomore year of college. Jen couldn’t fool the observant engineering major. Her bright, bubbly personality immediately had him directly questioning her about her choice of biology as a major. They had only known each other for a few months at that point, but Jen reluctantly admitted to being forced into the major by her parents. Will had been horrified by the confession. When they began to date, he gently and gradually convinced her to find something that she loved and pursue that.
It took four years, but together, they were able to discover Jen’s love of teaching and children. Just a few months shy of graduating with her biology degree, Jen realized that she didn’t want to work in a lab for the rest of her life like her parents. It took some serious persuading, but Will was able to convince her to get her teaching credential right after she graduated.
“Ready to go?” Will asked, green eyes lighting up as he held out his arm for the young woman to take.
Jen smiled back, looping her arm through his. Will led her out of their hotel room and down the hall. The restaurant they were going to was in the hotel and was supposed to be amazing.
“How was work today?” Will questioned as they walked arm in arm. He chuckled a bit when the girl began to talk animatedly about the day. He loved asking about her job. She loved it so much. Teaching was truly her passion.
Jen looked very much like a little girl on Christmas when Will led her to a fancy-looking sushi restaurant. She was even more excited when they were led past all the tables indoors to a door that went outside. Will kissed her on the cheek when the waiter opened the door to reveal a single table on a balcony overlooking the ocean.
The waiter couldn’t help but chuckle when Jen immediately ran over to the balcony, so she could look down at the beach below. After taking the drink orders from Will, he left the two alone.
Will grinned as he watched his girlfriend rise up and down on her tiptoes as she looked out at the scenery. Sunset was approaching so the sky was an array of striking pinks and oranges, making Jen appear to glow in her glittery dress. He approached her slowly and wrapped his arms around her from behind.
“Are you happy?” he whispered in her ear.
Jen nodded happily. “I couldn’t be happier,” she said sincerely, turning in his arms so she could throw hers around his neck.
Will chuckled before pulling away slightly to look into her eyes. Her breath caught at the amount of love in his eyes. “I could be,” he said.
Jen blinked in confusion but before she could question him, the waiter returned to take their food orders. Jen was starving and became immediately distracted by all of the extravagant rolls that she could choose from.
About twenty minutes later, the happy couple was enjoying their meal. Soft music played in the background on their private balcony. It was a warm, comfortable night. The sun was just about to set when Will suddenly stood.
Jen stared up at him in confusion. “Will?”
He just smiled at her before pulling her up out of her seat. His eyes were glassy as he took both her hands in his.
“Jen,” he began. “We’ve been together for five years today and they’ve been the best five years of my life.”
Jen smiled up at him, trying to fight back her concern at his sudden seriousness. “We’ll always be together,” she promised.
Will nodded firmly and took a deep breath. “I’m going to make sure of that,” he said before getting down on one knee.
Jen gaped at him with large eyes as he reached into his pocket to produce a tiny velvet box. He held it up, the bottom lying flat in the palm of his hand.
“Jen, I love you,” he said, looking directly into her eyes. “I promise to take care of you and love you for the rest of my life.” He lifted the lid then, causing Jen to gasp at the ring that sat inside.
An oval diamond sat in the center, surrounded by shimmering amethyst stones. The white-gold band was decorated with intricate swirls.
“Will,” she whispered, barely audible.
“Marry me?” he said, holding the ring out to her.
Jen’s vision blurred as tears gathered in her eyes. She opened her mouth to answer but a sob escaped. She nodded vigorously, rubbing her eyes with the heels of her hands.
“Shh,” Will murmured. Jen hadn’t even noticed that he had stood up to gather her in his arms and press her to his chest.
It took Jen another moment to compose herself. When she did, she pulled away to smile widely at Will. “Yes! Yes, I’ll marry you!”
Will pulled away so he could remove the ring from its box. Jen couldn’t help but notice that his usually sure hands were trembling just a bit as he gently slipped the ring onto her finger. He then pulled her into his arms again, more firmly than he had just moments before.
He was never letting go.
“Jen, we need to talk.”
The young woman looked over quizzically at her new fiancé, trying to process the reason behind his serious tone and expression.
They had just come back to their hotel room after spending the day on the beach. It had been full of bliss and fun. They frolicked in the waves and built sandcastles before getting ice cream at a local shop. They had planned a quick nap before dinner.
They had just showered together, and he was sitting on their large king hotel bed. His light brown hair was damp and slicked back. He had on a pair of dark pants and a navy-blue button-down shirt.
“Is something wrong?” Jen asked. She had been brushing her waist-length brown hair and stepped away from the small vanity to approach her future husband.
“No, angel,” he said. He pulled Jen toward him and guided her to sit on his lap. He toyed with the bow on the back of her knee-length purple dress idly as he spoke. “You’re going to be my wife soon and I thought it would be beneficial to talk about what that means.”
“It means that I’m going to be yours,” Jen said, her confusion doubling. She knew what being a wife meant.
“Yes, that’s true,” Will said. He lowered his hand down to rest it on her knee, making Jen squirm a bit. That usually signified the start of a punishment.
“Am I in trouble?” she asked in a small voice.
“No!” Will exclaimed in shock, then realized where his hand was and retracted it before wrapping his arms around her middle. “I’m sorry, angel. No, you are not in trouble, but that’s kind of related.” He paused. “Do you like it when I treat you like a little girl?”
Jen blushed at that. “Yes,” she admitted softly.
It was something that the two had developed over their five years together as a couple. She craved the freedom that young children had, to be able to do things like color and play with toys.
Will discovered the desire in Jen by accident. They had been long practitioners of domestic discipline and one day, while Jen was being spanked, she’d accidentally called him Daddy. It had shocked them both, but since then, Will had been slowly introducing aspects of ageplay to his shy fiancée. It was a slow process. Jen had a hard time letting go and admitting this part of herself. Will was determined to change that.
“When we’re married, you aren’t just going to be my wife,” he explained carefully. He put a finger beneath her chin, so she was looking him in the eye. “You will be my little as well.”
Jen’s eyes widened.
Will stared at her unwaveringly. He raised an eyebrow when Jen shook her head.
“Will, we can’t,” she said simply, averting her eyes.
“Why not?” he asked. He didn’t sound angry though, just curious.
Jen shifted on her fiancé’s lap, still not looking at him. “I just can’t.”
“Look at me, please.”
Jen did so, with some difficulty but Will pretended not to notice.
Will took Jen’s tiny face in his large hands, cupping her cheeks gently. He placed a gentle kiss first on her nose then her forehead before staring into her chocolate brown eyes.
“I love you, Jen,” he began seriously, brushing her baby soft cheeks with the pads of his thumbs. “I love you for who you are: a sweet and strong young lady. That young lady is mature and responsible but that isn’t all that makes up who you are, is it?”
Jen knew where he was going with this but did her best not to react.
Will paused to allow her to respond. When she didn’t, he continued. “There’s also a little girl inside you who is begging to be let loose. I love her as well and want to nurture her and guide her. Will you let me do that?”
Will held his breath as he waited for Jen to respond. He knew it was a lot for her to take in. He let out a huge sigh of relief when she smiled, and tears filled her eyes. He tightened his arms around her, pressing her small body into his chest. He rubbed his cheek against the top of her head, loving the way her soft hair felt against his skin.
Will let her cry against his chest for several minutes. He whispered soothing words to her while stroking her back. He even bounced her on his knee as if she were a small child.
When her sobs eventually subsided, he patted her back. “I think it’s time for someone to take a nap.”
Jen shook her head against his chest. “I can’t nap now,” she protested with a sniffle. She pulled away to look up at him with red-rimmed eyes. “We can’t nap after all that. Let’s talk this out!”
Will shook his head. “We have plenty of time to talk,” he assured her. He lifted her off his lap easily and set her on her feet in front of him. “You’re exhausted. We’ll talk after our nap.”
Jen frowned, her lower lip jutting out just a bit. “I’m not tired,” she said firmly.
Will raised an eyebrow. “Yes, you are.”
“Jen,” he said her name firmly. “What happens when you argue with me?” He pinned her with a hard look.
Jen blinked. She knew the answer of course but chose not to give it. “I’m not tired,” she repeated instead.
Will’s eyes narrowed into thin green slits. “I just had you sitting comfortably on my lap, young lady,” he said. He patted his thigh. “I can have you in a similar position that won’t be as comfortable if you choose to disobey me.”
Jen’s temper flared at his words. She stamped her foot before yelling, “I am not your wife yet! I said I’m not tired and I’m not going to nap!”
Within seconds of the outburst, she was thrown face down over Will’s lap. She gasped and wriggled, immediately regretting her words when his large hand landed several times on the back of her skirt.
Will’s expression was hard as he spanked his fiancée’s bottom. Part of him was expecting an outburst after he had this discussion with Jen. He didn’t mind. It was the perfect opportunity to reinstall his dominance over his little girl.
“I didn’t think you enjoyed napping with a red bottom,” he said, flipping up the back of her dress to reveal pink cotton panties. He patted the thin fabric. “You consistently manage to prove me wrong.”
“I don’t like napping with a red bottom!” Jen whined, reaching a hand back to cover her little rear.
Will’s response was to grasp her tiny hand in his much larger one before pinning it to her back. “When you misbehave, you are implying the opposite,” he said. He raised his hand then and brought it down hard in the middle of her bottom. He watched with satisfaction as Jen’s pantied cheeks bounced in response.
“I’m sorry!” she cried out. She mewled as Will began to alternate fast swats to each cheek.
Will decided this wasn’t going to be an extremely hard spanking. He could tell that Jen was nervous about the prospect of letting the little in her shine. He was sensitive to that. However, disobedience could not be tolerated if they were going to have a happy and healthy marriage.
However, this spanking wasn’t to be taken lightly. He concentrated the majority of the smacks to the lower half of her cheeks. They were moderately hard spanks, loud and stingy, even over panties. He paused after a few dozen, when he could feel the warmth of her bottom through the thin panties.
It took Jen a moment to realize that the spanks had stopped falling. When she did, she looked over her shoulder at Will. He was rubbing her panties in slow circles. His firm expression made her realize that he wasn’t done with her yet.
“Why are you getting punished?” he asked.
Jen whined at that. Her fears were confirmed. Her bottom wasn’t safe yet. She wiggled a bit, trying to word her response carefully. “I didn’t want to take a nap.”
Will’s fingers found the waistband of her pretty panties. “You’re not getting spanked because you didn’t want to nap,” he said before swiftly pulling the thin fabric down to her knees. Her firm and round buttocks bounced into view, causing the young woman to cry out.
“Because I disobeyed you!” Jen corrected quickly. “I’m sorry!”
“Very good,” Will praised before staring down at her bottom fondly.
It was a very cute bottom. Jen was a small woman, barely five feet tall, but her bottom definitely wasn’t tiny. It wasn’t gigantic but it was fleshy and round. Each cheek fit in Will’s palm perfectly. He told her often how perfect he thought it was. Jen disagreed however, often complaining that her tush was too big. She was very self-conscious about her bottom, often wearing long shirts and skirts to conceal it.
Will grasped Jen’s right bottom cheek in his hand. He kneaded it gently before smacking it sharply.
Jen gasped and clenched her cheeks together.
That earned her a harder smack to the same cheek. And another to the left one. It took Jen a moment to figure out why the smacks had gotten so much harder, but when she did, she struggled to loosen her muscles.
Will rewarded her by fondling the two cheeks. “Are you going to nap when I tell you to from now on, little one?”
Jen moaned. “Yes, sir,” she managed to say.
“Good girl,” he said. “Almost done. You’re only getting ten more.”
“Yes, sir,” Jen squeaked, clutching the bed sheets in her small hands.
Will didn’t make her wait for long. He circled her small waist with one arm and lined up his opposite hand to the very center of her tush before letting it land sharply. He ignored Jen’s gasp and continued, leaving just a second between each smack. His large hand made it so he was able to spank every inch of her bottom twice.
Jen did her best to stay still for the final swats but each one made her bottom burn worse than the one before. By the fifth smack she was wriggling violently and flailing her limbs.
Will sped up the final swats, sensing his fiancée was almost at her limit. Jen’s bottom was a bright pink and emanating a nice amount of heat. Will hated to leave marks on her bottom and very rarely did but he wanted to make sure she felt the effects of the spanking after it was over. After the tenth swat, he kneaded the soft mounds, making the young woman moan. He waited for Jen to catch her breath. When she finally did, she looked over her shoulder at him. He was smiling gently at her.
“Alright, little one, up you get,” he said with a light tap to her tush.
Jen rose enthusiastically, sensing she was forgiven. She hopped up and immediately began to rub at her punished bottom. She dug her fingers into the hot flesh and pouted at her fiancé petulantly.
Will chuckled a bit and wrapped his arms around her, pulling her close. He kissed her cheek and looked into her eyes. “Ready to nap now?” he asked.
This time, Jen obliged immediately. Will scooped her up easily before falling back on the large bed. Jen giggled when he rubbed his stubble against her cheeks as he tucked her against his chest.
Despite all the fuss she had put up about napping, Jen was fast asleep in seconds after Will had her settled in his arms.