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Here is the next chapter! :) 

Chapter Six

Jack awakes to the sound of a bird chirping loudly outside his room. The light is bright from the sun, and he rolls over, trying to close his eyes once again, but it is too late. He sighs as he sits up and lets out a giant yawn and stretch. He shifts his weight as he reaches down to feel the thick pink diaper that was in-between his legs. He frowns when he feels the warmth from his touch – he wet in his sleep again.

What is going on? He wonders if subconsciously he was doing it on purpose? But why…the last thing he wants is to make Aunt Jennifer feel as if he needs to wear diapers…right?

A few moments later, he hears a knock on the door.

He gulps as he pulls the blanket on top of him, staying quiet, hoping that she will think he is asleep and walk away.

His luck isn’t that good, and Jack hears the door open, and Aunt Jennifer walks in. She is wearing jean shorts and a blue tank-top; he notices that she isn’t wearing a bra either.

“Good morning, Jack.” She says as she closes the door behind her.

“Good morning, Aunt Jennifer.” He says in a small voice, hoping that she leaves soon and doesn’t try to inspect his diaper.

“How did you sleep last night?”

“I slept well enough,” he says as he tries to hold himself together, “what about you?”

“I slept alright, had a weird dream though.”

“Oh yeah?”

“Yes….” She gives him an odd look but doesn’t elaborate on what her dream was about. She then walks over to his bedside, tracing her fingers along with her blanket.

“Time for breakfast, eh?” Jack lets out stifled laughter.

“Oh yes, but first I need to check the state of your diaper.” Aunt Jennifer replies as she pulls back his blanket to reveal his pink diaper. His cheeks turn as bright as the diaper is.

She leans forward and places a hand on his diaper before he could move; she clicks her tongue together a few times and shakes her head. She looks up at Jack and smiles.

“It seems like I was right to diaper you.”

“That’s not…I mean!” He tries to find words to protest with, but he knows that it doesn’t matter. He did wet his diaper after all. He feels himself sink lower, but also flinch slightly at the feeling of her hand against his diaper.

“I’m going to change you before we eat breakfast.”

“What?!” He screams out, before covering his mouth, his cheeks are on fire now.

She stares at him, her hand still on his diaper. “I said I’m going to change you. I need to make sure that you clean up properly; otherwise, you might get a rash.”

“I don’t think that…”

She gives him a stern look, and he remembers the conversation from the previous night.

“I mean, yes, ma’am.”

“That is a good boy,” she replies, before patting his diaper, “although would a boy really wear a pink diaper?”

“You put it on me!” He protests, not fully understanding what she is trying to imply.

She leaves the room for a moment, returning with a box of wipes. “Spread your legs so I can get in-between you, it will make things easier.”

He obeys, unable to face her as she positions herself right between him, reaching over and pulling at the tabs of the diaper and bringing it down – revealing his wet diaper – and his hard dick.

“My, my, what is this?”

For a moment, he believes she is talking about his obvious hard-on, which she has witnessed several times before.

“It looks like someone had another type of ‘accident’ in his diaper…”

It was at that moment he remembers the previous night…and what he did in his diaper. He looks at her who is wearing a devilish grin upon her face. He feels himself shrink, and he wishes he could run away from this moment.

“Was it because you saw me naked yesterday?” She laughs as she pokes his penis. “I’m guessing you liked what you saw. Can’t say I don’t blame you.”

With that, she reaches over and starts to wipe him down, which makes him feel even more embarrassed and little. How much more of this can he take?

“You’ve been so good lately.” She says, “I feel like I should reward you.”

“Oh?” He turns his head to look at her. What could she mean by that?

It was then she pulls down her shirt, revealing her sizeable perky breast, dangling not that far from him. “I asked if you were thirsty before…”

Did she want him to suckle on her nipple? He licks his lips as he watches her bring down her breast closer to him, but as soon as he was about to reach for it – she pulls away and lifts her top.

“Perhaps another day.” She gives him a wink before she gets up. “Get dressed; time to get ready for the day.” She then leaves the room; he closes his eyes, his heart racing a million miles a minute.

Nothing unusual happens for the rest of the day – in fact, Aunt Jennifer plays it off as if nothing happened between them that morning. It was then he remembers the previous text he got from his friend for a party, it started at six, and it was a quarter till then now.

“Aunt Jennifer?”

“Yes?” She hums as she looks up from the couch.

“My friend invited me to a party at…am I allowed to go.”

“Of course, you may. No need to ask me permission…however, do remember your curfew.”

He sighs, wishing he could somehow escape it, but decides it is best not to worry about it at the moment. “Yes, very well.”

“Have a good time then, and be careful. Don’t do anything reckless.”

“I won’t.” He says as he makes his way to his bedroom to get ready. He messages his friend to come to pick him up, and it only takes about five minutes before he is outside his door.

“Bye, Aunt Jennifer!” He calls as he leaves the house and hops into his buddy’s truck.

“So you’re staying with your hot aunt?” His friend, Isaac says as they start to drive to where the party is at.

“Yeah, I am. Just until I get on my feet.” Jack says.

“Lucky you,” Isaac with a laugh, “have you done anything yet?”

“No! I mean, she is my aunt.”

“No, she is not,” Isaac says, “not biologically. Dude, what is your problem?”

“I don’t have one,” Jack mumbles, feeling slightly embarrassed as he thinks back of what happened that morning. He doesn’t’ tell Isaac about that though.

They arrive at the house in a few minutes and get out of the car; Jack welcomes this as he stumbles inside, grabbing a beer as he socializes with people he knew in high school that is attending the same university as him. It is hard for him to grasp that he is no longer in high school, and in a few short days, he will be going to his first class for the semester.

But, also the thought of at home he is forced to wear diapers and be treated little by his aunt.

What is he going to do about that?

He tries to push the thought from his mind and have a great time with his friends. He drinks a lot, takes a couple of shots, they play a game of pool, a bit of dancing – soon time slips away from him.

“Wow, it’s close to midnight.” He hears someone calls as he stumbles to find a bathroom. He stops dead in his track.

“What did you say?”

“I said it’s almost midnight.”

“Oh shit.” He fumbles around to find Isaac, who was sitting on the couch between two pretty females. “Isaac, you have to take me home, my aunt is going to flip.”

“You’re an adult, mate. What is she going to do?”

He didn’t even want to begin to imagine what she could do.

“Come on now.”

“No way, I’m having a good time.”

Jack groans as he heads out the door, thankful that the walk wasn’t that long – but he was already late. Would she care? Are her threats empty? Will, she even remember, or will she let him go off the hook?

It takes him a bit longer to get home, as he drank quite a bit and is feeling drunk. He makes his way to the door and unlocks it with his key, trying to be quiet, but it is difficult as he drops the key and mumbles a few cuss words in his mouth before he can open it.

When he does, he sees his Aunt Jennifer standing there, her arms crossed.

“You’re late.” She says, her voice filled with anger and Jack knows that he is in big trouble now.

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Chapter Seven

“Aunt Jennifer I swear…” He starts to say, but she holds up her hand, shutting him up.

“Didn’t I tell you the rules when you first started to live here?” She asks, taking a step forward.

“Yes, but I mean…I was just having fun…I’m an adult you know!” He spits out, feeling the confidence bubble up inside of him, but he knows as soon as he said it, it was a bad decision.

“Oh, you’re an adult now? That means you can do whatever you want without any consequences?” She asks of him.

“No! I mean…yes! I’m thankful that you let me live here…but I shouldn’t have to be treated as a…as a…” He fishes around for the right word.

“A what?” she asks as she takes another step forward.

“A baby!”

“Oh, so you’re not a baby then.” She is now touching his cheek with her fingers, a smile upon her face. “Very well, we shall see. Go to bed right now. If you keep your bed dry, then I will let you do whatever you want. However, if you do have an accident…., you must do whatever I want.”

“That’s not…” Jack takes a deep breath. “Fine. Deal.”

“Good. No going to the bathroom before bed, though.” She gives him a sly smile.

“That’s not fair,” Jack grumbles.

“An adult can hold it even if they had a lot to drink.” Aunt Jennifer shrugs her shoulder.

“Fine! I’ll do it then!” He says as he marches to his room and slams the door. He takes a deep breath, trying to push away the feeling of his bladder. If he concentrates hard enough, he won’t wet the bed. He knows that he will be able to do this. He has done it before. He went through most of his life without any accidents in the first place.

He gets dressed for bed and climbs underneath the covers; it isn’t long before he is out like a light.

--

The following morning he wakes up, and he knows he is in trouble. He doesn’t have to move much to feel the wetness beneath him. He curses to himself and falls back onto his bed, wanting to cry out in both humiliation and frustration. What is Aunt Jennifer going to do to him now? He bites his lip as he hears her in the distance.

He whimpers as she flings open the door.

“Now will you listen to what I say?” She asks, there is no need to check his bed, for his room smells of urine. “You don’t know better. It’s quite clear to me that you are doing this because you enjoy the attention you get…you enjoy wearing diapers…you really got excited by the thought of suckling on my tit. What kind of man does that? Especially the time you wear pink diapers. I have some fun plans in store for you…that is if you want too….”

“What plans?” Jack asks.

“You can continue to live here, rent-free – go to school, get a part-time job, save up money – on the outside world you’ll be a normal college student. BUT. Once you walk through those doors your under my command and must do everything I say. You behave and listen – I’ll give you a generous reward, but you misbehave, and you’ll have to face the consequences.”

Jack stares at her, trying to figure out what she means. What does she want from him?

“Just tell me….what exactly you want from me? Is it just you want me in diapers or…” Jack pauses when he realizes that Aunt Jennifer is holding something in her hand…it looks like a big fluffy pink dress.

No.

“This is what I want from you.” Aunt Jennifer smiles, “I think you’ll make a cute diaper girl, don’t you think?”

“What, but I! I’m a boy!” Jack complains.

“Boys aren’t hairless!” Aunt Jennifer gives him a wink as he remembers that she shaved almost every hair off only a few days off. “If you agree…I’ll give you a reward right now.”

“I don’t know…” Jack says. “I don’t think…”

“I know you’ve had a crush on me,” Aunt Jennifer says, “I’ll admit…you’ve always intrigued me. I know that you enjoy this. I bet if I check you’ll be hard right now…you’re always hard when you’re around me…when I diaper you when I change you when you saw me naked…come on, be my sweet little girl and I’ll make your dreams come true.”

“But what if I don’t like it?”

“I won’t do anything you truly don’t enjoy,” Aunt Jennifer tells him, “so long as if you give it a shot. But, based on everything I’ve witnessed and know from you – I think it won’t be long before you’ll both accept and love this new you.”

“I…I…” Jack stammers, not sure what to think. His head slightly hurts from drinking the previous night. Should he say yes? If it was to wear diapers, he could handle that; he has to admit they did feel soft….but a dress? How humiliating was that?! But…why did the thought turn him on so much? He curses at himself, not wanting Aunt Jennifer to know that she was partly right.

“Fine.” He gives a defeated sigh.

Aunt Jennifer leans over and pats him on the head. “What a good little boy…or should I say, girl.” She giggles as she helps him pull off his shirt and put on the dress. It was satin, a light pink that fluffed out at the bottom with white lace. She also places a pink clip in his hair to go along with it, as well as another big pink diaper between his legs.

He felt foolish as Aunt Jennifer stands before him, looking him over.

“Perfect! And from now on, you shall be known as Jessica.”

“Jessica?”

“Yes, it’s cute, but now you have been a good little girl and listened to Auntie Jennifer. I’ll give you a nice reward.” She sits down on the bed, pulling down her top, revealing her breast. “Come sit on my lap, and I’ll feed you.”

“R-really?” He asks as he stands there and watches her. She nods her head and pats her lap once more. He walks over to her and gently hops onto her lap, she holds him close as she brings him closer to her breast. His heart is pounding in his chest, and he licks his lips - wondering if this was really happening. He soon wraps his mouth around her nipple and begins to suckle as she brings him as close as she could to him

She then places her hand upon his diaper bottom and begins to rub and pat, causing him to wiggle slightly.

“That’s right, fill up that tummy!” Aunt Jennifer giggles as she continues to rub and pat at his diaper crotch; he knows that she can feel his dick beneath it. He moans as he continues to suckle on her nipples.

It feels amazing. He can’t explain it. The way she is holding her close to her body, her nipple in his mouth, her soft pats on his diapered bottom – even the dress and the hairpin – is driving him crazy.

“I knew someone would enjoy this.” Aunt Jennifer whispers as she grabs hold of his dick through the diaper and begins to rub it, causing him to let out a long moan.

“Such a dirty little girl,” Aunt Jennifer continues, “I knew all along…if you just listen to what I say then you would be enjoying more stuff like this.”

He nods his head as he suckles, but it’s getting harder to focus as he knows he is about to cum in his diaper.

“I think a naughty little girl is going to fill up her diaper soon.” Aunt Jennifer giggles as she continues to rub at his penis through the diaper, it feels so good, he can’t control himself, and it isn’t long before he feels himself release in the diaper. He breathes hard, catching his breath. He can’t remember a time he came like that before. He looks up at his aunt, who is beaming down at him.

“Good job,” she says as she leans down and kisses his forehead, “I knew you could do that. There will be lots of happy endings if you do everything I say.”

He blushes wondering what more can come with this. He hops down from her lap, even more, embarrassed now that he came in a diaper while wearing a dress and suckling from her nipple.

Aunt Jennifer holds out her hand for him.

“Come on; I want to see where you’ll be sleeping from now on.”

His face turns bright pink as he looks around. Is he going to be sleeping in her room now? “But I thought…”

She shook her head. “This was just a temporary placement for you. But this room is way too big for such an itty bitty baby girl.”

What had he gotten himself into?

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Another great chapter @Mamabug. I can't wait to read what Aunt Jennifer has in store for Jessica now. Is she going to take his virginity with a strap on? Oh the naughtiness of it is incredible. 

 

Thanks for sharing.

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This sure isn’t going in a direction I thought it would. That’s definitely not a bad thing either. Jack, or I guess I should say Jessica had to have some of these desires in him before Aunt Jennifer brought them out much more. I have little doubt that the next really big embarrassment is going to come when a friend sees her in a pretty dress and diaper. Very happy to give this a like and I am really looking forward to reading more. 

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Only 2 more chapters after this! :)

 

 

Chapter Eight

Jack stands there in front of the locked door; his heart is pounding in his chest as he feels his palms getting sweaty. He looks up at his Aunt Jennifer, who is fishing out a key in her pocket. What is going to lie behind this door? He isn’t sure what he should be feeling at the moment. Aunt Jennifer squeezes his hand as she places the key into the lock and turns it.

Because of the silence, the clicking of the door echoes in the hallway.

“Welcome to your new room, Jessica.” Aunt Jennifer snickers as she pushes open the door and they walk in.

Jack stands there in complete awe as he looks around the room.

On the left-hand side, there stands a sizeable looking crib; it was white wood, with some pink blankets inside. There was even a mobile attached the ceiling hanging down. On the right-hand side there stood what appears to be a long dresser, but with a mattress on top of it. He shifts around his weight, believing that it must be a changing table.

He turns to see the closet, wide open, filled with dresses! He sighs as he looks around the room. This is where he would be staying? The room was filled with pinks, whites, and purples. Even the girliest of girl would probably deem there is too much pink.

“I have to stay here?” He asks as he turns to look at his aunt.

“Not all the time,” she says, “you can use the other bedroom to work on any classroom work or for some TV and gaming time. However….” She walks over to the crib and pats it.

“You will be sleeping in here. Don’t worry; it’s comfy.”

“I don’t know….” Jack starts to say, but when his aunt gives him a particular look, he stops in his tracks, “I mean, yes, ma’am.”

She walks over to him and kisses his forehead. “It will all be okay! I promise! Aunt Jennifer will take care of my cute little girl!”

“Ummm,” Jack wiggles around, feeling the diaper in-between his legs, “about the diaper...”

“Oh, you’ll be in them from now on.” Aunt Jennifer says. “I have thinner one’s for you to wear to class.”

“What?! But I don’t need…”

“Little miss; you better stop it right now.”

“I can wear here,” Jack continues, “but at school, I would much rather I wore regular boxers…I don’t want…”

“That’s it!” Aunt Jennifer states, “I told you before that if you listen to me and obey, you will get pleasure – but if you don’t – you will be punished.”

“I’m sorry I –“Jack tries to correct himself, but it is too late. Aunt Jennifer grabs his hand and yanks him over to her room. Her room is rather simple, a large queen size bed, a TV, a dresser, a small computer in the back corner.

“Lean over the bed,” she commands of him, and he decides its best not to protest anymore. He nods his head as he leans over the bed, sticking his diapered bottom in the air. What is she going to do to him?

“I think a spanking will be too easy for you,” she says. “You will probably enjoy it like last time. I’ll be right back. Don’t move.”

He pushes his head into the bed, closing his eyes. He can hear her walk away, but it doesn’t appear she goes very far.

When she returns, he feels her pulling up his dress and yanking down his diaper, so his bare ass was showing.

“Spread your legs.” She tells him and once again, he does as she says, but he is still fearful, his mind with a million possibilities of what she is about to do.

He lets out a small squeal as soon as he feels something pushing up against his butt. “What are you doing?” He asks as he tries to get up, but she places her hand on his back, pushing him back down in the bed.

“Shhhh, accept this punishment…otherwise, it’ll get worst.” She tells him as she continues to push the butt plug in, it slides in quickly as she lubed it up before sliding it inside of him. He squeezes his eyes shut as he digs his head into the bed, trying to pretend he was anywhere else. Once the butt plug was all the way in, he feels her pull up his diaper and slaps his bottom a few times.

“There we go! Much better!” Aunt Jennifer says as she helps him stand up.

“How does that feel?”

“Weird,” he mumbles, every little movement he makes, he can feel the plug inside of him, “how long am I going to have to wear this?”

“Until I’m satisfied.” Aunt Jennifer grins as she reaches over and pinches his cheek. “Don’t give me that face. I’m sure if I reached in your diaper, I would get quite a handful.”

He blushes, knowing that she isn’t exactly wrong, but he doesn’t want to admit it.

“I think my little girl is getting a bit hungry; I think it should fetch you a bottle.” She says with a wicked smile. “Go wait for me in your nursery and I’ll go get you a bottle.”

“Yes, ma’am.” He says as they both leave the room, she heads to the kitchen as he then makes his way to his new bedroom. As he enters it, he glances around once more.

What is going to happen to him?

It was then that he hears Aunt Jennifer walk into the room, in her hand is a large bottle filled the brim with some juice.

“Here we go sweetie,” she says, “let’s get that tummy filled with some juice!”

Aunt Jennifer sits on the floor and pats her legs for Jack to lie across her. He nods his head as he sits down upon her lap, she pulls him closer to him as she places the nipple of the bottle into his mouth, and he starts to drink it.

“Such a good little girl!” Aunt Jennifer coos, which causes him to blush even more, “I’m sure it won’t be long before little Jessica fills up that diaper up!”

Jack can feel himself shrink down the more she talks down to him. Why does this excite him so much? The feel of the diaper against his crotch, the butt plug that is buried in his ass, the dress that he is wearing and now being bottle fed. It is driving him crazy. He wishes he could feel more of her…

“Is my little girl having dirty thoughts?” Aunt Jennifer asks, and the look on his face gives it all away.

“Perhaps as a reward, Auntie Jennifer will give you even more pleasures! But, until then you have to do as I say.”

Jack nods his head as he continues to drink the bottle; it doesn’t take long for him to empty it.

“Aw such a good little girl, I have! Great job, Jessica!” Aunt Jennifer leans down and kisses him on both of his cheeks.

“Thank you,” he mumbles with a blush as he wiggles a bit.

“Since you’ve been well, I’m going to let you go play in your room for a little bit,” Aunt Jennifer says as they stood up from the floor, “remember, you have to use your diaper for….everything.”

He feels himself grow hot, but what if he has to do number 2? He wants to ask her about it, but he knows he might get another punishment if that was the case. He decides to hold out and nods his head.

“Good girl, now go on and play. I need to take care of some housework.” Aunt Jennifer leans down and kisses his cheek – and even gives him a peck on the lips – before leaving the room.

Jack stands there and watches her leave, before heading back to his other room and starting up the computer, wanting to play a game.

He lost track of time, but it was probably about 30 minutes later when he suddenly feels the urge to go to the bathroom. His cheeks burn slightly as he tries to shake off the feeling, but it continues to press up against him as he tries to play his game.

However, it becomes too much for him, and another 10 minutes goes by – and he is unable to hold it back anymore. He feels his cheeks burn with embarrassment as he fills up his diaper. He places his hand against the diaper, feeling the warmth of it. He thinks about when Aunt Jennifer finds out – and he feels himself get a bit excited at the thought.

It is probably almost another hour before he hears a knock on the door; Aunt Jennifer walks into the room.

“It’s been quite a while,” she says with a smile, “are you having fun?”

He nods his head, saying nothing, shifting his weight in his seat. The wet diaper has been pressing on him for quite some time now.

She strode over to him and reaches down, going beneath the dress and touching his diaper.

“Hmm, looks like my little girl wet her diaper really well,” she says with a giggle, “I’m sure you’re expecting me to change you now?”

He nods his head.

“Hmm, I don’t think so. I don’t think that diaper is quite full enough….actually I think you’re going to need help to make it a real mess.”

“M-ess?” He takes a large gulp as he stares at her.

She can’t possibly mean…

“Come follow me,” she says as she holds out one of her hands for him.

 

 

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more clarity now...Jennifer is really into this, my guess is she has been planning this for a long time, and this might not even be her first baby...

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