His mom, who knew all too well about his sissyish tendencies, decided that triple thick cloth diapers and plastic baby pants at night were the correct answer. Between that solution and a crinkly vinyl mattress cover, she finally managed to successfully keep his bedding dry. He was embarrassed having to wear the humiliating diapers but his mom had her mind made up.
They had a routine every night when Denna would report to his bedroom at 7 00.
But as time went on, Denna fell into the dismaying habit of wetting his pants during the day as well and his mom was forced to re-evaluate his situation. She decided on training pants initially and she ordered a batch of various cute designs from Ebay.
Denna managed to soak right through these so after a sound spanking, his mom began putting noisy plastic panties over the training pants, hoping the added humiliation would encourage Denna to try harder.
Her efforts notwithstanding, he would arrive home after school, with wet spots on the seat of his pants where his pee had soaked through the thin layered training pants. With a heavy sigh, Denna's mom realized more serious measures were needed and only a thick, thirsty pair of diapers would be enough to keep his pants dry throughout the day.
But Denna was having still other problems at school. The stress of trying to live up to being a boy was apparently too much for the youth and he tended to cry over the slightest provocation. After being picked on by the other boys and teased about being a sissy, his mom considered pulling him out of school. She was at her wit's end and unsure of what to do with her prissy son when she hit upon an idea.
As it turned out, her good friend happened to be a tutor and one day, over some drinks around their swimming pool, she agreed to teach Denna at home for a fraction of her normal fee.
When Denna came home that afternoon, his diapers soaked as usual, his mom brought him into their kitchen to meet his new tutor.
Denna blushed with shyness at his new teacher. He had always had difficulty holding eye contact with attractive women and this stunning stranger was certainly no exception.
"Hello Denna, my name is Heather," she said in a voice reserved for toddlers, "I'm sure you and I are going to be the best of friends," she greeted him warmly, "And I'll bet you're anxious to get out of those wet diapers and into some dry ones, hmm?"
Denna's face burned hotly with embarrassment. Up until now, nobody knew about his shameful habit except his mom and his anger at her was exceeded only by the crushing shame he felt as Heather looked down at his bulging hips and smiled knowingly. It was only with great effort that he fought back the tears blurring his vision.
"Aww, don't cry little Denna," she said as she leaned forward, giving him an excellent view of her fabulous cleavage, "maybe you can show me where your mommy keeps your diapering supplies?"
"What a wonderful idea!" his mom gushed, much to Denna's chagrin, "And what a great way for you two to get a chance to know each other better."
With his cheeks blazing with shame, Denna reluctantly led Heather back to his room with her close behind him. He'd totally forgotten that he'd left his pink teddy bear on his bed and as they entered his room, he momentarily panicked. Doing his best to shield it with his body, he quickly threw it on the far side of the bed but it was too late.
"What a lovely teddy bear!" she remarked eagerly, "Why don't you hold that for comfort while I'm changing your pampers?"
Poor Denna was far too weak-willed to say anything to oppose her so he held his teddy in his arms as she gently laid him down on the bed and began taking his pants off.
"You can call me Ms. Heather, from now on, Denna," she said as she pulled his pants down and exposed his bulging, wet diapers, "And from now on, I'll be your teacher and nanny and there's going to be a few other changes around here as well."
As she reached down to peel his clinging plastic panties off his diapers, Denna could hardly return the look her in the pretty eyes.
"Now that you're out of school, and away from all those teasing boys, there's no need for you to wear all these extra clothes. You and I are going to go shopping and we'll pick out some cute diaper shirts and tops that will make changing you easier. Won't that be fun?"
Denna gasped with humiliation at the future she was painting for him but again, he was too much of a coward to say anything to stop her.
"I'm also a big believer in spankings so I expect you to do as you're told, without question--Do I make myself clear?" she asked, her tone serious now.
"Ye-yes, Ma'am," he squeaked weakly as he clutched his teddy bear to his chest tighter.
Quickly and efficiently, she cleaned up his damp bottom and groin before taking a fresh stack of diapers and positioning them under his rump.
"We'll start today on your new warddrobe. It just so happens I know of a store across town called Babies And More that will have all sorts of cute outfits in your size. You've made it clear to your mommy that you want to be more of a baby so I'm going to make sure you get what you've been asking for."
Denna started to protest, his mouth trembling as he struggled to think of a way to prevent what was happening to him.
Taking a big pink rubber pacifier out of her purse, Heather plopped it into Denna's gaping mouth and beeped him on the nose playfully.
"And now let's get you diapered and ready to go--we want to be sure to beat the crowds downtown," she told him as she began pulling his plastic panties up his legs.
What had his mom gotten him into? Was this the end of Denna's attempt to reach maturity?