As Anna sipped her glass of wine in the easy chair, a pleased, satisfied smile slowly began to appear across the features of her very pretty face. She twirled her long, silky dark hair in her free hand as she gazed off toward the hallway, listening intently. In the room next over, the harsh, rhythmic slaps of a hard wooden paddle could be distinctly heard, swatting the tender bare bottom of Francis, her neighbor's 15 year-old sissy boy. His mother had left the door wide open, so that every crisp swat of the paddle, every sobbing howl of the boy being so thoroughly punished, could be easily heard. And howl he did. With Francis' high pitched voice, he sounded more like a five year-old schoolgirl than the teenager he really was.
And while Anna couldn't actually see the tears now streaming down his face, she could plainly hear the penitent tone of his crying, accompanied by the hard, angry swats of his mommy's paddle on his soft, youthful bottom.
To be sure, he was now regretting his earlier bluster and rudeness towards Anna. That, and his quite silly claim when he had boasted that he didn't need to wear diapers for bedtime. She had laughed out loud at him when he had said it but his mommy had take a much more serious view of it. Now he was in his nursery, prissy shorts and panties down, bent over her lap, and getting a much needed lesson in truthfulness and manners.
Occasionally, the spanking was interrupted so that his mommy could make a specific point to her errant son. This was always followed by a particularly hard swat from her paddle to emphasize her remarks, in which Francis let out another piteous howl of pain. Anna could easily imagine him, crimson bottom in the air as his feet kicked and thrashed about wildly, his panties tangled around his ankles, helpless to stop the assault on his stinging, defenseless cheeks. The paddle would be leaving fresh, angry marks on his buns with each blistering smack, until the entire surface was a hot, blazing inferno of cherry redness.
At long last, the humiliating punishment was finally over. All that could be heard now were Francis' sobs and crying as his mommy dressed him for bed. It took about five minutes, during which time, Anna patiently sipped from her wine.
With his mommy leading him by the hand back out of his nursery like a little child, Anna beamed with amusement as she took in his humiliating makeover. It was a sniffling and defeated sissy that now stood before her, all of his previous bluster, a thing of the past.
Gone was the delicate silk blouse he had been wearing before. Now he had on a short, frilly fleece top decorated with bunnies and giraffes that barely extended to his navel and a hem ending with a flouncy white ruffle. The top's overall pink color was set off by the short puffy white sleeves that accented his toneless, skinny arms. On his feet were lacy pink anklets, giving him the further look of little girly-ness.
But what really stood out was the big, fat, bulky diaper now securely and shamefully pinned around his narrow hips. It was quite wide between his smooth, hairless legs and it forced him to toddle about with a very baby-like waddle. The thickness of his diapers hinted that a long night of wetting likely awaited the incontinent boy. His shiny white nursery print plastic panties covering his diapers were stretched to the limit; they were snug, yet well fitted, and his mommy had taken great care to make sure all of the voluminous cotton cloth was contained within them.
As he stood before her, still sniffling, he stared at the floor in abject shame while he held his stuffed teddy bear in his hand and a baby bottle filled with warm milk in the other. His cheeks and neck were blushing a deep shade of red and he couldn't bear to make eye contact with his stunning next door neighbor.
Looking him up and down closely, she smiled and crossed her sexy, shapely legs, dangling a high heel within his field of vision.
"Francis would like to make a confession to you," his mommy announced, standing alongside him with a chart of some kind in her hand, "Go ahead, honey...what do you say to Miss Anna."
Anna smiled sweetly and sat up forward to better look at the emasculated sissy.
"Yes Francis--what would you like to tell me?" she asked sweetly.
He swallowed hard and tried to clear his throat.
"I...um.....ah...."
Never having been seen before by his neighbor while wearing his shameful nighttime diapers was absolutely mortifying for the bedwetting teenager. And her having been such an intimate witness to his spanking only made matters worse. He could only hope the floor might suddenly open up and swallow him, abruptly ending his humiliating misery.
"Honey, talk to Miss Anna--not the floor," his mommy chided him as he shuffled his feet.
His face blushed an even deeper shade of red as he looked up into his pretty neighbor's chestnut eyes. She smiled back at him with expectation but underlying that was smug confidence and superiority from having just seen him be so thoroughly put in his place by his mommy.
"I hafta wear diapers at night," he mumbled, the embarrassment nearly overwhelming him as tears of shame welled in his eyes.
"And why is that, Francis honey?" she asked innocently.
"Um....cause, um...I'm a be-bedwetter," he replied, once more staring at the floor.
Anna reached her slim, finely manicured hand over and gently patted the fat, bulging seat of his diapers, feeling for herself, the smooth plastic panties that would be retaining all his wetness tonight.
Her other hand went to his chin, delicately raising it and forcing him to look her in the eyes.
"And is that why you sleep in a crib with a waterproof mattress cover on it?" she asked tenderly.
He cringed as she made mention of his shameful bed meant for a baby.
"Yes, Ma'am," he replied between sniffles as he blushed anew.
He had SO wanted to keep this a secret from this woman he had come to idolize since she had first moved in next door last month. But now all the terrible secrets of his sissy lifestyle had been fully exposed to her, revealing just what a simpering pantywaist he truly was.
"Well. Now wasn't that easier than getting your little bottom spanked, hmm?" she asked the humiliated boy.
"Yes Ma'am."
Once more, she gently patted his thickly diapered bottom maternally, looking into his eyes which only made him squirm even more uncomfortably before her.
"Francis also wanted to show you his bedwetting chart," his mommy volunteered as she held the grease-board up with a monthly calendar superimposed in it.
"The Ws represent every morning that Francis has woken up with a wet diaper. As you can see, he hasn't had a dry night the entire month."
The object of her discussion bit his lip and stood fidgeting, his cheeks burning brightly with acute embarrassment as his childish habit was revealed before this beautiful young woman.
"Well, it certainly looks like you belong in diapers, Francis. Maybe when I come over to babysit you, I'll just get you changed--first thing," Anna suggested.
Francis shook his head vehemently.
"No! I don't wet during the day," he protested in his whiny, high pitched voice.
"I'm not so sure..." she said uncertainly, "I think just to be on the safe side, I'll put you into your diapers and plastic panties as soon as I come over. Especially since you have such cute panties to wear," she giggled as she fingered the pretty lace around the leg holes of his vinyl underwear.
"Mommy!" he cried desperately, "don't let her do it!"
She crossed her arms over her chest and scowled down at her diapered sissy son.
"When she's babysitting you--she's in charge, Francis. That'll be up to her.
"And maybe if you were diapered during the day, that might give you more incentive to stop wetting your bed during the night," she reflected.
"Come along baby," Anna said as she stood up, towering over the diminutive boy in her high heels, "it's beddie-bye time for you now. Let's tuck you into your crib and then it will be lights out."
Her voice had taken on a tone of voice reserved for ordering around toddlers as she led the defeated, spanked sissy back into his nursery.
Waddling awkwardly, Francis pouted but let her take his hand as she led him into the warmly lit room he spent much of his time in.
Taking a moment to marvel at the furnishings, Anna paused as she took in the full sized crib, painted in pink with white trim, the similarly painted dresser, stocked with a row of dolls along the top, and a low, sturdy changing table covered with practical, waterproof vinyl, along with stacks of diapers and plastic panties. The faint but stale smell of pee-soaked diapers could be discerned from a large plastic diaper pail in the far corner, despite it's closed top. There could be no doubt that a bedwetter slept in this room. Lastly, frilly pink curtains diffused the light coming in from the single window and Anna caught sight of the polished, well used wooden Spencer paddle hanging up next to the dresser.
She led him over to the crib and pulled back his baby blankets, tucking him in and making sure his teddy bear was close by to snuggle with. As she smoothed his ruffled blond hair out of his eyes, he didn't even notice as she coaxed the rubber nipple of his baby bottle between his lips and urged him in her sweet gentle voice to nurse on it.
"That's it, baby, sweet sissy dreams....night-nite."
Betty Pearl's Sissy Stories 20.1
Topic: Confession of a sissy bedwetter (Read 20772 times)
