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Billy's Dilemma
#1
Billy's Dilemma

 
 
Billy fidgeted anxiously as his mommy undid his trousers, pulling them down past his clammy wet trainers and the colorful nursery print plastic panties that were doing such a brave job of containing his afternoon's incontinence.

He wasn't anxious because he had once again failed to keep his trainers dry during the day, nor was he upset over the thick stack of cloth diapers that were awaiting him on his mommy's bed--after all, it was a foregone conclusion that he would be wetting the bed, just as soon as he dozed off during his daily nap.

No, the reason Billy was anxious, was because he knew that Ms. Rosen, his mommy's friend, was just outside the door in the living room, waiting patiently for her to finish changing him so they could return to their discussion. His own bedroom was down the hall, which meant it would be impossible to avoid walking right past Ms. Rosen in just his t-shirt and fat, embarrassing diapers. Not to mention that he was certain that his mom would require out of politeness that he say his goodbyes to her, before being tucked into bed for his nap.
And although he believed his trousers were up to the task of hiding his trainers, he knew it would be totally impossible to try and pull them over the triple layer cloth diapers his mommy insisted he always wear to bed.

It was bad enough at the age of thirteen still having to take a nap during the afternoon, but having to do so in bulky, babyish diapers and plastic pants was unbearably humiliating to the shy sissy. And yet, they both knew that the only alternative was a wet bed when he woke up.

He whimpered weakly as his mommy tugged his soggy wet trainers and plastic panties down his legs, exposing his tiny little nub that so far, had stubbornly refused to grow past an inch, even when it was fully aroused to stiffness. He had thought for sure that this would be the year for him, the year in which his little baby-sized penis would finally start to grow along with those of the other boys but so far, he hadn't seen any indication whatsoever that that was the case.

His mommy led him over to the stack of fluffy, bunny soft diapers which, while he knew from experience would feel wonderful, would not alleviate the excruciating embarrassment he would soon endure when Ms. Rosen witnessed his inevitable entry into the living room.
He had really hoped to keep his bedwetting a secret, but it appeared his mommy had other plans for him.

Feeling both utterly helpless and frustrated, Billy bunched his fists in mute impotence as his mommy busied herself with the daily task of raising his legs up high and smearing a thick coating of diaper rash cream across his bashful bottom, followed by a generous application of fragrant baby powder all around his tiny little pee-pee. Billy briefly considered putting up a struggle but the nearby paddle on his mommy's dresser dissuaded him. It would be doubly humiliating knowing that Ms. Rosen would distinctly hear every harsh, biting swat of the paddle on his tender bottom, and then having to face her afterwards as the tears spilled down his face would just be too much to deal with.

Instead, he kicked a little and struggled but his mommy easily pinned the multiple layers of bulky, soft cotton around his hips after which she smiled down on her swaddled baby captive.

Billy was really hoping for the plain white waterproof panties today but such was not to be. Instead, his mommy picked out a pair that seemed deliberately designed to humiliate the poor sissy. With a smile, she held them aloft like a Nobel prize, and Billy gasped as he took in the babyish pink nursery print plastic panties with the soft ruffles around the legs and waistband.

"No!" he whined weakly as she began snaking the emasculating panties up his slim, hairless legs, working them over the soft, bulky cloth of his diapers. Billy hated these panties the most and it was just his bad fortune that Ms. Rosen happened to be visiting today.

His mommy shushed his protests as she worked her long fingernails around the snug elastic waistband of his panties, making sure her little bedwetter's nap time would be uninterrupted by leaks.

Billy tried to rise up, to put an end to this humiliating procedure, but his mommy pushed him back down, keeping him in place long enough to powder between his thighs and the fat, imposing diaper between them.

It was a blushing, red-faced sissy that was led out of the room by the hand of his mommy to say his goodbyes to Ms. Rosen.
The beautiful woman beamed at the prissy boy as he waddled awkwardly into the room.

He wanted to run for his bedroom, to escape the humiliating attention surrounding him but his mommy held him firmly by the wrist, ensuring he would get his full measure of shame and embarrassment.

With her free hand, his mommy bent down a bit and squeezed the very thick seat of his diapers, making him squeal a little.

"What do you say, Billy," she prompted him.

"I--I have to take my nap now," he stammered with his cheeks blazing crimson, his eyes unable to hold the glittering gaze of his mommy's intimidating friend.

"Aren't you just the cutest thing," she gushed, "Come over here, little sweetie."

Billy was mortified to have this gorgeous woman drawing out the moment of his humiliation and he gulped hard as she easily scooped him up and placed him on her lap like he was just a toddler.

"There's nothing like a freshly diapered boy--you smell like baby powder and plastic, and you certainly look well protected for your nap time," she effused, "These cute pampers really suit you. When I come over to babysit you next weekend, I think I'll keep you in diapers and plastic panties around the clock--what do you think about that?"

Billy whimpered and squirmed in her lap, his cheeks only burning a deeper shade of red.
"And I just might bring over a cute little outfit for you to wear too," she said with a playful beep of his nose, "Something to go with these pretty panties."

Billy blushed furiously at her comments and attention--the absolute last thing he wanted today before his nap. It was obvious that she thought of him as nothing more than a hopeless bedwetter who couldn't be trusted without his diapers and plastic pants.

He fidgeted on her lap as he struggled to think of way to make his escape.

"Billy, why don't you tell Tasha here why you're wearing diapers now," his mommy prompted him.

Her sissy son tried hard to look away from the stunning woman holding him in her lap but she seemed to be all around him--her pretty blue eyes stared into his own and when he looked down, her sexy high heels and silky legs only seemed to intimidate him further. Turning back, he tried to think of something dignified to say but he couldn't think straight as he stared into the deep, yawning cleavage between her two bountiful breasts.

"I'm up here sweetie," she said as she placed her perfectly manicured finger under his chin and redirected his attention back to her pretty face.

Billy swallowed hard. Her perfume surrounded him and he felt overwhelmed by her beautiful, very adult presence.
"I-I-I sometimes...w-wet the bed," he admitted shamefully, the humiliation practically crushing him.

"Awww, well some little boys just never outgrow their diapers and plastic panties, sweetie pie jr.," she said sympathetically, albeit in a syrupy, condescending tone of voice.

Billy didn't quite know what to say to that remark so he squirmed some more and blushed even deeper.

"But at least you get to wear some really cute panties, hmm?" she said with a smile.

Billy had never been so embarrassed in all his life.

"I-I guess so," he replied unconvincingly as he stared down at her lap and pouted.

"Is it difficult finding diapers in Billy's size?" she asked his mommy as she softly patted his generously padded bottom.

"Oh no, you'd be surprised what's available these days online," his mommy replied, "Billy's a heavy wetter, so I put him in three diapers, plus a couple of soaker pads in between. With a good, snug pair of plastic panties like he's wearing right now, his bed remains dry, even through a long night of wetting."

Billy's cheeks were blazing hot, having to listen to this mortifying discussion about his most private of secrets. It certainly didn't help that Ms. Rosen was gorgeous, as well as sexy, and her hand was roaming over his diapers, checking the fit of the vinyl panties around his waist and patting his fat, puffy bottom affectionately.

"Here you are, baby," she said as if reading his mind, "I brought you a little something to ease your troubles."

Before poor Billy could react, Ms. Rosen popped a big pink rubber pacifier into his mouth, ending all possibility of a dialogue between them. His mommy chuckled and thanked Tasha for her thoughtfulness, lifting her diapered sissy son up and setting him on the ground.

Billy, now completely defeated, waddled numbly as his mommy took him by the hand and led him back to his bedroom where his waterproof covered mattress and teddy bear awaited him.


THE END
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#2
Awww I love that story Bobby. Yours are always a cute read. Thanks.
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#3
Another great story, Bobby. He clearly is not a fan but Ms Rosen knows him better than he knows himself and deep down I think he has probably made peace with that at least.
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#4
Ah, Bobby. It's another masterpiece. I really love your stories.
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#5
Thanks Bobby.
Always look forward to your stories.
Poor Billy, another long night in his thick nappies and plastic pants with only his teddy and dummy to comfort him.
Can't help but put myself in Billy's place!
Jiff
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