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Aunt Jennifer's Offer


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Hello!! This lovely commissioned story was submitted by @diapered jay! It is a very interesting premise and it's both like my normal style - but also a bit different! I think you all are going to enjoy this!

If you have a story idea and enjoy my writing style - I still have commissions open! For $3 per 500 words! If you're interested, please either PM me here or email me at redqueen.bdsm@yahoo.com :) 

I will be updating the chapters every Wednesday & Friday!

Enjoy the story!!

 

Chapter One

“I can’t believe my little boy is all grown up and heading off to college!” His mother proclaims with a small cry as the small family sits at the dinner table.  Jack and his father give each other a knowing look and shake their heads. His mother was always a bit overdramatic – he was her only child after all.

    “I’m not a little boy anymore, ma.” He mutters under his breath as he stabs a piece of meat with his fork before eating it.

    “Oh, I know that!” She sighs. “You’re 18 now. It’s hard to think of you not being here anymore…it’ll be so lonely without you.”

    “Hey, I’ll be here now.” His father interjects.

    “You two know what I mean!” His mother snaps back, but then calmly adds. “I’m just going to miss you.”

    “I’ll miss you too, ma. I’ll visit…it’s only a few hours away. I’ve been applying for jobs around there.”

    “I just can’t help but worry about you, Jack! What if you can’t pay your bills? Why don’t you let us loan – “

    “No!” Jack counters with a shake of his head. “I’ll be fine. I’ve been saving up all summer, and with a job, I’ll be able to make it.” He tries to sound confident, but he cannot help but be a bit worried. He knows that rent was expensive, even with roommates. Even though he had been saving his money, he would be lying to himself to say he wasn’t worried about making it on his own. The last thing he wanted or needed was his parents’ help. They’ve already done so much for him already.

    “You know, dear. Jack is going to be fine.” His dad says with a shake of his head. “No need to be worried so much.”

    “I can’t help it! I would just feel more comfortable knowing that he was with someone we trusted…not strangers…”

    “You know, your Aunt Jennifer lives right next to that university.” His father suggests, and Jack feels his cheeks burn slightly.

    Aunt Jennifer. The woman he has known since he was born. She wasn’t really his aunt, but she might as well be. She had known his parents since before they got married. She was this beautiful woman, who always liked to treat him like he was little – despite his age.

    “Oh!” His mother’s face suddenly lights up. “That’s right! She does live right next to the university! We should give her a call and see if she can give you a place to stay.”

    “W-what?!” Jack almost spits out his drink. “I don’t think that is…”

    “That’s a great idea,” his father replies, “would save you a lot of money on room and board…plus it would help your mother’s anxiety…which in the end, will help me.”

    His mother shoots her husband a look before looking back at her son. “It will be perfect! Aunt Jennifer, I’m sure, would love your company. She’s always adored you.”

    “I don’t know mom…” Jack says shyly, trying to hide the fact he was blushing slightly. Him living with Aunt Jennifer? It wasn’t as if he disliked her, quite the contrary. But…it  would take a weight off his shoulders if he could stay with someone he knew, didn’t have to worry about paying bills and focus more on college instead.

The more he thinks about it, the more it feels like the right move to make. Perhaps it wouldn’t be that bad…and after all; he was pretty much an adult now. He was confident she would treat him like one.

    “Okay, actually, that doesn’t sound like a bad idea.”

    “Great! I’ll give her a call in the morning and ask her about it. I’m sure she will be perfectly okay with it.”

    “You better behave yourself though,” His father chimes in with a wink.

    “Oh, should I give her a warning about….you know…the problem?” His mother asks with a worried look on her face, and he could feel his face starting to turn red.

    “Mom…that hasn’t been an issue for a while now!” Jack exclaims, unable to look at her directly. Why did she have to bring it up? It wasn’t an issue anymore; the doctors said he would most likely outgrow it, and they were right. How long has it been anyway? Over a year at least…

    “Just in case! I know stress can be a big part of it and you’ll be in college…and so far away from home…” His mother replies. “I’m sure she won’t care! She used to work at a daycare, remember? Accidents are nothing to her. Perhaps you should take some protection just…”

    “Please, mom stop!” Jack raises his voice, trying to remain calm, but could feel his face turning a bright shade of pink.

    His mother and father exchange looks before his mom reaches over and pats him on his arm.

    “I’m sorry dear; I know it’s a sensitive topic. It was just a suggestion.”

    “I understand that,” Jack retorts as he threw a napkin on his plate feeling a bit frustrated, “I’m finished. I’m going to go take a shower and head to bed.”

    “Okay, I’ll let you know what Jennifer says in the morning.” His mom replies. “Goodnight.”

    “Goodnight.”

    Jack heads up the stairs and into the bathroom, leaning over the sink as he stares at himself in the mirror. Even though he is 18 years old, he looked to be about 15 with his baby smooth skin – as he was never able to grow much facial hair. He runs his fingers through his short, wavy brown hair as he undresses. He turns on the shower, before stepping in.

    It had been a while since he had seen Aunt Jennifer. The last time was around Christmas before he graduated high school. The present she gave him was one of those adult onesies that one wears to bed. It was perfect in the cold months, but of course, she had to comment on how cute and little he would look in it. Just thinking about it caused him to blush.

    What was it going to be like now?

    He exits of the shower, slips into his pajama pants and t-shirt, and slides into bed. He falls asleep quickly having a dream he later wouldn’t remember – something about Aunt Jennifer, pulling him toward her, his face leaning against her large chest.

    “Time to get up, kiddo!” He hears his mother outside his door. He opens his eyes slightly and groans as he rolls over; he looks down and notices his obvious hard-on pressing against the sheets. He places his hand over his dick, wondering if it had anything to do with the strange dream he had last night. He shakes his head. He’s had weirder dreams in the past that caused the same reaction. It was nothing new.

He waited a few moments before he got up and walked down the stairs, where his mother had a breakfast of scrambled eggs and toast waiting for him.

“There you are!” She proclaims in a happy mood. “I have some great news for you! Jennifer said she would be DELIGHTED for you to stay with her.”

“That’s good,” Jack replies as he reaches into the fridge for some orange juice before sitting down at the table.

“We’ll be driving you there next week – that gives you a bit time to settle in before college starts.” His mother continues.

“Okay.”

“She said she needed to get things ready for your arrival. I think she may spoil you.” His mother chuckles. “You used to follow her everywhere when you were younger.”

“Ma, please…” Jack mumbles under his breath as he starts to butter his toast. He knows his mother meant well, but she always says embarrassing things.

“I’m just saying!” His mother sighs with a shake of her head.

The rest of the morning was quiet, and Jack spent the remaining of the week slowly packing up to head over to Aunt Jennifer’s house. He was quite nervous about leaving home after 18 years, about going to college, to be living with her. He took a deep breath as he thought about it; trying to calm his nerves. Everything would be okay. At least he wouldn’t be living with a stranger.

The following week his parents packed up everything in their car, insisting they drive him (he had his license, but he doesn’t have a car of his own – most of his money saved up for school).

The next few hours were spent in silence, although a few times he could hear his mother crying in the front seat, obviously worried about her only son leaving the nest.

They finally pull up to a small house in a quiet neighborhood, only a few blocks from the university. Jack could easily walk there with no trouble. As his father pulls into the driveway, Jack notices Aunt Jennifer standing barefoot and smiling at the family by the open front door.

Is a gorgeous amazon; tall, athletic with curves, and large breasts. She wears her shoulder-length, wavy, brunette hair loose. She’s wearing a low-cut t-shirt and tight pants. Jack shifts his weight in his seat as his mother and father exit the car.

“Jennifer!” his mother squeals as the two women hug each other. “Thank you so much for doing this!”

“The pleasure is all mine!” Aunt Jennifer replies happily as Jack finally gets out of the car and makes his way over to her. Excitedly she asks, “We are going to have a lot of fun, right?”

The instant change in her voice as she talks to him, causes him to blush slightly.

“Thank you, Aunt Jennifer.” He shyly mumbles under his breath as he sees his father starting to grab his things from the car.

“Second bedroom to the left.” Aunt Jennifer calls out to him.

“You better be good,” His mother says, before hugging him tightly, “I’m going to miss you so much!”

“I’ll miss you too, ma.” He replies.

“Don’t worry, Denise, he’ll be in good hands. I’ll take care of him.” Aunt Jennifer reassures, causing his mother to smile.

“I know.”

After a few tearful goodbyes and many long hugs and kisses from his mother, he watches as they drive away. He turns his attention on the beautiful woman that was standing beside him.

She looks down at him (for she was a few inches taller than him,), and smiles.

“Well, we are going to have a lot of fun, aren’t we?”

He had no idea what was in store for him when he walked through those doors.

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Sorry for the delay for the chapter! This week has been hectic! Will try to get Friday's chapter on time as well! Anyway, enjoy!!

 

Chapter Two

“Well, welcome to my little abode!” Jennifer says as she opens the door and they walk into the house. Jack drops his bags on the floor as he looks around the house. It was indeed a rather small home, but it was quite apparent that Jennifer was very precise about everything. It didn’t seem like anything was out of place. His mouth felt dry, feeling a bit nervous that he would have to be extra careful not to mess anything up. He was also thankful, though, for the fact she is opening up her home to him.

It was then that Jack felt her hands slip into his, holding it tight as if he were a child as she takes a few steps into the living room.

“This is the living room. I have cable, Netflix and Hulu so you can watch whatever you like, I also have a crap ton of movies as well.”

“Sounds great.”

There was a large grey sectional couch against the bay windows.  A rug was laid out on the wooden floor, grey, black, and red. The TV she had was at least a 60-inch screen TV, with a large case next to it filled to the brim with movies.

“Now this is the kitchen,” Jennifer pulls his hand as she walks through the living. It was very open, with dark cherry cabinets and black fridge and stove. “Again, you can help yourself with anything in the fridge or the cabinets. I’m also a pretty good cook too!”

“That’s great to know; I don’t know how to cook anything,” Jack says.

“Don’t worry, I can teach you,” she pats the top of his head, Jack feels himself blush slightly as she drags him out of the kitchen and through the living room. She pauses for a moment as she points to a stand-alone room.

“This is my bedroom,” she says as she turns her head around to look at Jack, “this  area is off limits unless you wish to get a spanking.”

Her voice is cheerful and carefree, but there is something about her words that makes Jack feel like she might be slightly serious.

“I won’t.”

“Too bad,” she gives him a wink before they start to go down the hallway, she opens one door on the right-hand side, revealing a bathroom, “this is where the bathroom is,” she then opens the door on the opposite side, “and this is your bedroom.”

Jacks walks into the room and glances around. It was decently sized, with a full-size bed, a desk and a dresser.

“You can do what you want with it.”

“Thank you; I appreciate this all, Jennifer,” Jack replies as he begins to leave the room. He turns back to look at her as she gives him a particular look, but yet Jack cannot explain precisely what she is thinking.

Jack looks down the hallway and notices a third room, he waits for Jennifer to mention it, yet instead, she head s down the hallway and back into the living room.

“Let’s head over to your university; it’s only a few blocks away.”

“Sounds good,” Jack says as he turns and looks back at the door.“Hey, what is inside this room?” He goes to open the door but is surprised to see that it is locked.

“Nothing you should concern yourself with right now,” Jennifer replies with a knowing smile as she walks back over to him and grabs his hand once again. Jack frowns a bit as he turns back towards the door. What could be in that room? He always believed there to be something particular about her, even though she was still kind enough. Was there a deep dark secret he didn’t know about? Jack shrugs his shoulders, figuring it was nothing he should worry about.

The university turns out to be only about a half a mile away from her place, easily taking about fifteen minutes to walk there. Jack is excited to start university the following week, as well as a bit nervous. He knows it will be different than it was in high school. Once they return home, Jack tells Jennifer that he wishes to study a bit and prepare for the following week.

Jack feels it’s pretty stupid to give homework and assignments for classes that haven’t even started yet.

Jack spends a little over an hour, unpacking all of his things, setting up his computer, and working on assignments though it was a bit hard to concentrate at times.

It was a bit past five when he hears Jennifer’s voice calling from the kitchen.

“Jack! It’s dinner time!”

He sets his pencil down, closes the textbooks, and stretches before standing up and leaves the bedroom. He pauses for a moment and stares at the locked door still a bit curious about what was behind it.

“Something smells good,” Jack says as he enters the kitchen. On the table was a large bowel of spaghetti and two plates.

“Thanks!” Jennifer beams as she sits down. “Please sit and eat! We have a lot to talk about now that you will be living here.”

Jack felt deadness sweep over him as he nods his head, sitting down as he begins to fill his plate. What did she mean by that? Was she going to have a lot of strict rules that he would have to follow? If that were the case, he would much rather leave and stay in a dorm room with other roommates. He is18, after all. 

Silence falls over them as they eat in silence. Jack glances up once in a while from his plate, staring at her, wanting to know what she is thinking. A few times, she glances up at him right at the moment he does, and their eyes meet. She gives him a smirk, and it causes his cheeks to flush slightly as he stares back down at his plate.

He still found her quite beautiful.

“That was really good,” Jack says as he leans back and pats his stomach.

“Thank you,” She replies as she gets up and grabs the plates before taking them over to the sink, “are  you all settled in?”

“Yes, I am.”

“That’s good, now come with me to the living room. We have a few things we must discuss.” With that, she exits the kitchen and walks to the living room – Jack following her. She sits on the sofa and pats right next to her; Jack nods his head as he sits down.

“Okay, so first of all,” Jennifer says with a clear of her throat, “you  must refer to me as Aunt Jennifer at all times – miss or ma’am – will be accepted as well.”

“What?” Jack stares at her, wondering if she was joking, but she does not change her expression. “Okay…,” why did she want him to continue to call her Aunt Jennifer? It wasn’t as if she was really his aunt.

“Number two,” Jennifer says, holding out two fingers as she continues to speak. “Your bedtime is 11:00 PM, sharp on the weekdays – on the weekends it is midnight. No exceptions.”

He stares at her for a long time when she says this. Has she gone crazy? It wasn’t as if he was one to party all night or stay late. But, at 18 years old, he felt as if he should have more freedom then if he were still living with his parents.

“Why?”

“Because I said so and this is my house. If you wish to stay here, you must obey my rules. For the most part, you can do as you please, but there are certain ways that I like my house kept, and I plan to keep it that way.”

“Yes,….ma’am.”

“Lastly, you must do whatever I say without question. I will not do or say anything to harm you in any way,” Jennifer says, “As I said there is a certain way I like to keep my house, and I will not tolerate any poor behavior. If you do break any of these rules, there will be consequences.”

“Yes, ma’am.”

“Also,” Jennifer says, “your mother also told me that you sometimes have a bedwetting problem. Because of this, you are to be diapered every single night – by me – so I can make sure that you are properly protected, and not wet my sheets. They’re very expensive, you know.”

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Sorry everyone for the late delay! Here is the next chapter! Enjoy!

 

Chapter Three

At that moment, Jack could feel his face grow a bright shade of red. He turns his face away from Jennifer, wanting to get up and run away, but his feet were frozen in place. Why did his mom have to go and tell her that information? How embarrassing! And to top it all off – why did she want to diaper him? The thought of her seeing him naked was almost too much.

“I don’t…”

“Don’t what?”

“That’s not really, I mean,” he fumbles around for the right words to say, he is still unable to look directly at her. “That’s not really a problem anymore.”

“But, it could happen, correct?” Jennifer asks as she folds her arms; he could feel her eyes staring right at him.

“It hasn’t happened in like over a year…” Jack mumbles.

“You want to live here? You need to follow my rules. This is one of my requirements.”

“But, Jennifer!” He shouts out and then sees the look in her eyes. He realizes what he has said and quickly tries to take it back. “Aunt Jennifer. I’m sorry.”

She stands up and holds out her hand. “I think you need to have a taste of what I mean; perhaps then you’ll be much more likely to obey.”

He stares at her for a few moments before holding out his hand to hers. She grabs it before dragging him to his room. What was she going to do? He felt his cheeks turn pink – was she going to try to put him in a diaper?

She sits down on the bed and pulls him over where he was almost across her knees. “Come on now.” With the tone of her voice, he did not want to argue with her. He sheepishly leaned across her knees. He felt as she grabbed his shorts and boxers and pulled them down, revealing his bare ass for the world to see.

One smack.

Two smack.

Three smacks.

He closes his eyes tightly, trying to focus on anything else. He had mixed emotions. On the one hand, he was utterly embarrassed that as an 18-year-old man he was lying across this beautiful woman’s lap as she spanks him – but another emotion started to stir underneath the surface, there was a bit of pleasure mixed in which just caused his cheeks to turn even redder.

Once she finishes with the spanking, she pulls up his boxers and shorts and stands him back up. He appeared small now as he looks directly in her eyes. It was then he notices that she is much taller than he was, that even with her sitting on the bed, he didn’t have to look down to her.

“I think I make myself very clear now.” She says, her voice was soft but stern. He knew that she meant what she said. But why did she want to treat him like this? But the bigger question was, why was he a bit turned on at the moment?

“Yes, ma’am.”

“Good,” she says as she stands up from the bed. “I want you to have a good time here; I want to help you save up money as you attend college. But, these are my rules…and I think eventually you’ll learn to appreciate them.”

“Yes, Aunt Jennifer.”

“Do you have any questions?” She asks as she lingers by the doorway.

I shake my head. “No, ma’am.”

She looks down at her watch. “You have a few hours before its bedtime. You may do whatever you want them. But don’t forget my rules.”

With that, she leaves him alone in his room, shutting the door behind her.

He stands there for a few moments, staring at the door and then back down to his bed. He could still feel the slight sting from her spankings on his bottom.

It was then he felt his phone vibrate in his pocket. He picks it up and notices that his mom was calling him. What was he going to say?

“Hello.”

“Hey, sweetie! How are you doing? Are you settling in? Jennifer was so excited for you to be there! I’m sure it’s been a bit lonely for her living by herself.”

“Oh yeah?” Jack says with a sigh as he thinks about the fact that she has lived on her own for as long as he could remember. He remembers a few times she had brought home or mentioned a boyfriend, but they never seemed to last. How lonely it must be to come home to an empty house every night.

“Is everything okay, Jack?” He hears his mother on the phone; he shakes his head, realizing he had got lost in his thoughts.

“Yeah, everything is going great. I got everything set up, and Aunt Jennifer even showed me where the university it, its super close.”

“That’s great, honey! I’m sure the two of you are going to have a great time!”

“Thank you, mom.”

“Okay, I’ll talk to you later. Have a good night. Love you!”

“Love you too, mom.”

 He takes a deep breath as he gets on his computer, trying to get a bit more work done. A few hours later, he hears a knock on his door.

“Come in.” He calls as he shuts down his computer.

“It’s almost bedtime,” Aunt Jennifer says.

“Okay,” Jack replies as he gets up from his chair and stretches. When he turns around and looks at her, it is when he notices she is holding something in her hand.

A diaper.

His cheeks flushed a bright pink, he almost forgot about that! She wasn’t serious, though, right? He hadn’t needed to wear diapers since he was a young teenager, back before he got his bed wetting under control.

“Oh,” he looks down at the ground, unsure what to say, “if you insist, Aunt Jennifer. But, I promise that I haven’t had a problem in a long…”

Before he could say anything else, Aunt Jennifer was right there in front of him, looking down.

“Do you wish for another spanking?” She asks, and he takes a large gulp, shaking his head.

“Then I guess you better lay down on the bed so I can put you in a diaper. I need to make sure it’s on correctly; otherwise, you could leak all over my sheets.”

He gulps, unsure what to say to her. He felt like if he didn’t do as she says, she would kick him out of the house and where would he go? He starts school in a week that was not enough time to get his own place. He couldn’t go back to his parents’ house either, and he couldn’t tell them what was going on, that would be embarrassing! Plus he already paid for the first semester of school…

He feels as if he is trapped between a rock and a hard place.

There was no way out of his situation.

He figures though that after a few dry nights, perhaps he could convince her he didn’t need the diaper anymore…it was at least worth a try.

He slowly gets onto the bed and lays down.

Aunt Jennifer lies the diaper down next to him on the bed as she slowly begins to pull down his shorts. He bites his lip as he turns his head away from her. He feels her pull them off and watches as she tosses them on the floor. She then grabs hold of his boxers and slides them down next. He feels his cheeks burn, and he wants to shrink down. When he agreed to this whole arrangement – this was the last thing on his mind!

He was secretly thankful though that his dick wasn’t sticking up as he was a bit turned on not that long ago.

Aunt Jennifer doesn’t say anything or make any unusual expressions when she sees him naked. Instead, she reaches for the diaper and opens it up, before grabbing his leg and pulling it up so she could slide the diaper beneath him. She yanked up the front of the diaper and taped it snuggly against his hips. The feeling of the diaper between his thighs was a strange one.

“There we go,” Aunt Jennifer smiles as she rests her hands on her hips. “That should protect you from any accidents. Now get into bed you go. You need to get used to an early bedtime before school starts.”

“Yes-ma’am.” He says in a weak voice as he crawls to the other side of the bed, getting beneath the covers.

Aunt Jennifer walks over the door and pauses, before turning and looking back at him. “I’m delighted that you are here, Jack. I think you’ll soon understand.”

“Thank you for having me.”

“Goodnight, Jack.”

“Goodnight, Aunt Jennifer.”

With that, she shuts the door, leaving him there alone. He shifts his weight, trying to get comfortable. Every time he remembers what he is wearing, it causes his face to flush. He was glad that no one else would find out about it. He was determined that after a few dry nights, he would talk to Aunt Jennifer about not wearing diapers anymore – it was too embarrassing! He would pay for any cleaning if it happened he did have an accident.

It didn’t take long for Jack to fall asleep.

The following morning, he heard Aunt Jennifer knocking on the door, letting him know he had 10 minutes to get up as breakfast was ready. He let out a stretch when he suddenly remembers he is wearing a diaper.

He reaches forward to touch his diaper.

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Someone's going to get a surprise and I bet another spanking because Aunt

Jennifer is going to think he lied about wetting the bed. ? "I wonder is she

lonely for a man or the fact she never had a baby of her own. I hope it's the

later. Would love to see him treated like a real baby on the week ends, Diaper

changes, bottle feeding maybe have him suckle to make her feel like a Mommy

not an Auntie.

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Chapter Four

 

As soon as he places his fingers against the diaper, he could feel his cheeks burn as he felt the wetness. Sometime during the night, he had an accident. The diaper was cold to the touch, which told him that it happened a while ago. How did this happen? He was positive that he wouldn’t have an accident. He bites his lip as he pulls himself out of bed, knowing he needs to get out of this wet diaper before Aunt Jennifer spots him and claims that she was right all along that he needs to wear diapers.

But it would already be too late.

Before Jack could slip the wet diaper off of him, he hears a click from his door.

Aunt Jennifer walks in.

“Well, well, well.” She clicks her tongue as she folds her arms in front of herself; her eyes were focused right on his wet diaper.

At that point, he wishes he could crawl underneath the covers and hide forever.

“It looks like I was correct about your need to wear diapers,” she replies as she gives him a smirk.

“It’s not…I mean…” Jack tries to fish around for something to say, some excuse, but he was left with nothing. How could he argue when he is literally standing in front of her in a wet diaper?

She holds her hand up, which silences him.

“I think you’ll know better not to question my ways now,” Aunt Jennifer says with a shake of her head, “now hurry up and get out of that wet diaper so we can have some breakfast.”

With that, she turns around and leaves the room, but not before glancing one more time at him.

Jack sinks onto the bed as soon as the door closes, putting his face into his hands. How can he ever face her again after what happened the previous night and what she saw this morning?

Part of him wants to call his mom up and tell her to pick him up – what excuse could he tell? And what would he do about college then? He bites his lip, he wants to go, and this was an excellent opportunity for him. Did he have any other choice? Perhaps he should stand up to Aunt Jennifer and let her know that this is nonsense; that he was an adult and Jack didn’t need to be treated as such.

He gets up from the bed and pulls off the wet diaper, throwing on a pair of boxers and shorts, before he heads to the kitchen.

Aunt Jennifer is already sitting down with a stack of pancakes in the middle of the table.

“Looks good,” Jack says as he sits down, trying to play off like what has just transpired didn’t happen.

Aunt Jennifer has her hands folded and stares at him as he reaches over to grab a few of the pancakes and places them on his plate.

“Y-yes?” He asks hesitantly, feeling as if he was going to regret this.

“You know I’m doing this all in order to help you?” Aunt Jennifer tells him. “I care about you, Jack. I really do. If you wish to continue to live with me…there are things you’re going to have to do. If you wish to call up your mom and dad to pick you up, you are free to do so….however, I will be informing them about the little accident you had this morning.”

He drops his fork and stares up at her, was she serious? Was she giving him an ultimatum? Stay here and do whatever she says…or his parents finding out he wet in his sleep again? He felt his cheeks burn once more, unable to look at her directly in the eyes. He didn’t have much of choice, did he?

“I um…” He tries to find the courage to speak what is on his mind.

“Don’t worry,” Aunt Jennifer says, “I’ll take care of everything, and if you’re good, there will be rewards in your favor. But, based on your reaction last night….I don’t think you can say you hated it.”

She is right, though. Even though being spanked was embarrassing to the max, there was a mixture of satisfaction that mingled with it.

“Yes, Aunt Jennifer.” He sighs, what else could he do? They finish their meal in silence, Jack unable to eat much more, suddenly losing his appetite.

Once he finishes, he excuses himself and heads to the bathroom to take a shower. The warm water feels good against his skin as it helps wash away all the troubles and thoughts that were going on in his mind. What was Aunt Jennifer’s end game? Did she get a kick out of doing this? Has she done this with other people before? He bites his lip; everything was confusing right now.

He turns off the water, getting out of the shower and wrapping a large towel around himself. He opens the door of the bathroom – to find Aunt Jennifer standing there.

“Aunt Jennifer..what…” His cheeks turn pink as she takes a step closer, placing her hand upon his cheek, feeling it.

“Do you trust me?” She asks him, her voice was like honey, so sweet. He feels as if he is going into a trance.

She steps even closer; her face was right up against his, he knew that if one moved their head just an inch, their lips would be touching.

“Yes…” He says.

“Good, now follow me,” she grabs his hand and leads him into his bedroom; he is clutching the towel to make sure it doesn’t fall off, “lie down on the bed.”

“Why?”

“Because I thought that it would be easier to help clean you up when you’re all nice and smooth.”

“What do you…” Jack starts to ask her, but she soon holds up a razor and a bottle of shaving crème. His face doesn’t grow much hair, so what did she mean….he feels his cheeks flush as he realizes what she means.

“I can do that!” He almost yells at her but catches himself as he clears his throat and continues. “I mean…I can shave myself. It’s no big deal.”

But, she shakes her head. “No, it will be much easier for me to do it. I want to make sure that you are completely clean – everywhere.”

“Aunt Jennifer  I-“ the look she gave him though, causes him to shut his mouth as he meekly nods his head and climbs onto the bed.

He turns his head away from her as she begins to pull back the towel from him, leaving him there wholly naked – this was the 2nd time she saw him in the past 2 days.

He wiggles around a little bit when he feels her start to put the shaving crème all over his privates and down his legs.

“Lift your legs, please.” She tells him. “It will make shaving you a lot easier. Stay still as well; you don’t want me to cut you accidentally.”

He nods his head as he lifts his knees, feeling even more vulnerable as he feels her run the razor over his private parts. She is very carefully, taking her time, wiping off the blade, and applying more shaving crème when necessary. He is partly thankful he wasn’t super hairy down there, to begin with, which should make it easier for her.

He lets out a slight sigh when he feels her touch his manhood, pressing it upwards so she could shave his balls. He bites his lip, trying to concentrate on anything else besides the fact a beautiful woman was touching him.

A few minutes go by, and he then feels her start to wipe him all down with the towel.

“I think we are finished! Have a look!”

Jack pulls himself up and looks down at him, feeling his cheeks turn pink as he notices he is utterly hairless from the waist down. Why did she shave his legs as well? He decided it was best not to question her.

“T-thank you.” He replies, still unsure about everything that was happening. It was then that Aunt Jennifer leans down and kisses him on the cheek.

“Thanks for being such a good boy,….for now.” She gives him a wink as she walks over to the closet, pulling out a pair of dark blue shorts and a light blue t-shirt.

“Here, put this on,” she says as she throws the clothes at him, “then you may do what you will for the next few hours.”

Once she left, Jack got dressed – feeling a bit silly with what he was wearing. It seems a bit…kiddish, but decides it was best to go with the flow of things. He places a hand upon his cheek; it was still burning from where she had kissed him.

He wiggles a bit as he notices he is getting hard by thinking about her touching his penis, her kissing his cheek, that moment in the bathroom when she was so close that he swore she was going to kiss him.

He bites his lip as he sits down on his computer to try to distract his mind.

He couldn’t help but wonder what else Aunt Jennifer has in mind.

 

 

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I'm happy everyone is enjoying the story! Here is the next chapter!

 

Chapter Five

Jack spends the next few hours organizing his room, watching TV, and getting a bit of homework done before the upcoming school week (which is only a few days away). Every once in a while, he leans down and touches his legs; the smoothness always causing him to blush. He couldn’t help but remember Aunt Jennifer so close to him, touching him – it excites him. What was wrong with him? She was a much older woman, his parent’s friend, and he grew up calling her ‘Aunt.’!

He sighs as he pushes himself away from his computer desk, taking a deep breath. He needs to get a hold of himself and stop having these kinds of thoughts.

Jack looks at his phone; it is 4:00 PM, about an hour or so away from when he would eat dinner with Aunt Jennifer. It was then when he notices a text from one of his high school buddies that was attending the same university as him.

Hey bro, there is a party tomorrow night. You in?

Jack pauses as he stares at the text. It has been a while since he’s been able to hang out with any of his friends, and it would be fun. He remembers the rule Aunt Jennifer has set for him, but he shakes his head, knowing that he could probably talk her into letting him stay out later.

Of course, what time and where?

He shoves the phone in his pocket as he heads out of his room, wondering what his Aunt was up too. He hears the TV on in the living room and makes his way over, spotting his Aunt sitting on the couch with some mystery TV show on.

“Hey, Aunt Jennifer.” He says, a bit embarrassed to be around her.

“Hey, darling,” she replies as she turns her head to look at him, giving him a broad smile and patting the seat next to her, “come sit and watch TV for a minute. I have some chicken cooking; dinner should be ready pretty soon.”

“Okay,” he says as he sits down next to her, wiggling a bit, noticing how close he was to her. She is wearing a short skirt, and since she was sitting down, it caused it to rise a little bit; he knew that if she was to move too much, he could probably spot her underwear. He gulps as he tries to focus on the TV, but he couldn’t help but glance at her every once in a while – and whenever he does – her eyes are staring back at him.

“You getting hungry?” She asks, and he nods his head.

“Yeah, that chicken is starting to smell good.”

“I guess I should go check to see if it’s ready.” Aunt Jennifer gets up from her seat and heads over to the kitchen. Jack stays where he is and watches her. He takes a few deep breaths as he tries to calm himself down before he also walks into the kitchen.

“Do you need any help?”

“That’s so sweet of you,” she says as she leans over and pinches his cheek slightly, causing him to blush, “if you would like, you could cook the veggies. There should be some in the freezer.”

“Okay.” He mumbles as he goes over to the freezer and pulls it open, pulling out a packet of frozen veggies and placing it in the microwave.

“Hey – Aunt Jennifer…”

“Hmm?” She doesn’t turn to look at him; she is busy preparing the mash potatoes.

“Why do you live alone?”

At this question, she pauses and looks up at him, giving him almost a sad smile. “Guess I just never found that perfect someone. It’s okay though; I’m used to being alone – but hey! Now I have you.”

He blushes at that statement as he turns away from her, silence soon spreading over them.

He can’t help but wonder why she did let him stay here with her…was this her plan all along? What else did she have in mind for him?

--

Once the two of them finished eating, Aunt Jennifer comments that she is going to take a shower and that he needs to do the dishes. Once she finishes with her shower she is going to make sure he is adequately protected for the night.

He doesn’t argue with her and waits until she is out of the room before he starts pulling the plates from the table and into the sink.

About twenty minutes later, once the dishes were done, he walks over to Aunt Jennifer’s room, knocking on the door.

There is no answer.

He knocks again, but still no answer.

He opens the door, believing that she might still be in the bathroom – however, instead he finds his Aunt standing there only wearing a pair of dark blue panties, drying her hair.

“Yes?” She asks, casually, as if he didn’t just catch her standing there naked. His eyes are glued to her large perky breasts.

“I’m-sorry. I thought…I mean…” He knows he should turn away, that this is wrong, but he can’t help it. He is stuck in a trance.

“What’s the matter? Are you hungry?” She playfully asks as she touches one of her breasts.

“No. I’m. Sorry!” He calls out as he quickly shuts the door and rushes to his room, closing the door behind him.

His face was probably as red as it possibly could be at that moment; he also could feel his dick getting hard at the look of Aunt Jennifer – she is incredibly sexy.

A few moments later, there was a knock on the door.

“It’s almost time for bed, sweetie. I need to make sure that a diaper is nice and snug on you.”

He steps back away from the door, letting her open and come in. She is wearing a black nighty – it was a bit revealing, and he could see her panties and bra on beneath it. Is she trying to seduce him? Or is she just teasing him? He honestly didn’t know.

He nods his head as he gets on the bed, lying down. He knew she was going to notice his erection, but he also knows if he rejects her diapering him – she was probably going to give him another spanking...or maybe something worse! He didn’t want to think about it. He figures it was best to just comply with her and plan on how to get out of diapers without causing any trouble.

She pulls off his shorts and boxers, before she shows him the diaper that she was going to put on him – it was bright pink.

“I think it is more fitting, don’t you agree?” She asks with a sly smile. His cheeks burn and he wants to say no, but instead, he nods his head and lets her put the pink diaper between his legs.

He feels her gently touch his dick, causing it to jerk a bit with her touch. He bites his lip as she puts some baby powder on him, taping up the diaper, so it was nice and snug, before giving it a few pats.

“Much better, I’ll check on you in the morning. Goodnight.” She replies with a wink as she stands up.

“Good night, Aunt Jennifer.” He mumbles as he watches as she closes the door behind her.

All he could do was picture her standing there naked before him, her long wet hair falling her back, her large breasts and pink nipples, her curves, her ass, her lips…it was too much for him to take. The more he thought about it, the more he began to ache. As he was lying there, he was unable to handle it anymore. He slides his hands down his diaper and begins to touch himself.

He groans after a few moments, knowing that the diaper is stopping himself. Suddenly a thought appears in his mind, and he pulls his hand out of the diaper and instead presses his fingers against the diaper and his hard dick. He lets out a small moan and bites his lip; the feeling wasn’t as he had expected.

He bites his lip as he goes faster, the bonus of wearing a diaper – a pink one none the less – drove him up the wall. He can’t remember a time he was turned on like this before. He continued to pick up the pace, his breathing getting heavy, he closes his eyes, knowing he is about to cum any second.

He imagines himself on her lap, suckling on her breast – her words “are you hungry?” repeating over and over in his mind.

It doesn’t take long before he orgasms, cumming in his diaper.

His cheeks are red, thinking about in the morning when she comes to check on him – what will she think if he wakes up with a wet diaper, and will she know that he came in it? Will she understand why?

Soon he feels his body start to relax, closing his eyes, he is soon fast asleep.

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