Trevor shuffled down the street, the humiliating, soggy wet feeling of his thick diapers squishing between his legs and surrounding his little package.
In moments, the two of them were standing on his front porch, ringing the doorbell, as they waited for his mom to answer. It didn’t take long, and as she pulled the door back, her mouth dropped open in shock as she beheld her sissy son for the first time in his adorable baby outfit.
“Trevor was bullying the girls next door—again—and I decided to take matters into my own hand. Looks like all that was needed was a fluffy set of pampers and a baby dress to get him under control.
“And sissy Trevor’s been enjoying his outfit so much, he’s already managed to wet his diapers.”
His mom shook her head in disbelief as she looked down on her prissy son, now so thoroughly pacified.
“Trevor, I’ve always thought you belonged in diapers—and the fact you’ve wet them only proves it. It’s obvious that you enjoy wearing them so it looks like it’s time for some changes around here.
“Your bullying days are over but your potty-training days are just beginning,” his mom told him, her arms crossed over her chest.
“I’ll be happy to help out until you get the stuff you need,” Jordan offered, “I’ve got plenty of diapers, plastic and rubber panties, a crib for afternoon naps and a hard oak paddle for those times when Trevor gets fussy or sassy.”
Trevor gulped with fear to think that he could expect to be getting spanked on a regular basis now.
“Excellent. That’s just what he needs,” his mom readily agreed, “Trevor, I’m going to box up all your big boy clothes today and put them in the attic.
“It’s time everyone sees you for the bedwetter you are.”
The flustered teenager’s cheeks flushed hotly at her blunt, humiliating announcement.
“I’m not a bedwetter!” Trevor protested vehemently.
While it’s true that Trevor’s bedwetting days were (mostly) behind him, he was mortified to have that history revealed to Jordan here on their porch.
“If you’d like, I can take sissy Trevor back over to my house, change his wet diapers and put him down for his nap,” Jordan offered helpfully.
“Thank you so much—that would give me time to get online and order up a big supply of the diapers and panties he’ll be needing now,” his mom replied gratefully.
Trevor stamped his feet in frustration. Now that Jordan had inserted herself into his life, he was helpless to prevent the strict, maternal discipline she had planned for him.
Reaching down, Jordan squeezed the fat seat of his wet diapers.
“Come along sissy, lets get those soggy pampers changed,” she told him.
Trevor’s lower lip thrust out, and he pouted in helplessness as Jordan took his hand and led him waddling across the street.
“I don’t wanna be a baby!” he complained bitterly.
“Well that’s too bad, sissy boy, because that’s exactly what you’re going to be from now on. You can count on diapers and baby outfits, bottle feedings and early bedtimes—oh, and a nice, long, soapy enema every morning.”
Trevor shook his fists as she led him inside and down the hallway towards the nursery. Just as she was reaching under the frilly lace hem of his baby dress to pull his plastic panties down, the doorbell rang unexpectedly.
“You stay right here,” she ordered him as she left the room to find out who was at the door. Trevor felt foolish standing around in his wet diapers and a quick glance at the full length mirror made him blush all over again—he looked just like a little toddler girl!
Several minutes later, Jordan returned with another woman behind her. Trevor recognized her as Leanne, one of the parents in the neighborhood who’s child he had routinely bullied.
“Well. I had to see it to believe it,” the woman said, “Looks like Jordan has finally put you right where you belong—in diapers and dresses.”
Trevor blushed even redder as he looked away in shame.
“Sissy Trevor wet himself and needs a diaper change before his nap,” Jordan explained, “but now that you’re here, maybe I should give him another enema for all the trouble he’s caused your children.”
“I think that’s a wonderful idea,” Leanne agreed wholeheartedly.
“He already got his bottom paddled this morning for terrorizing another girl but a second enema will do him a world of good,” Jordan said as she took the red rubber bag and went into the bathroom with it.
Trevor could only fret and wait in angst as Leanne glared down at him, eager to see him get his long, overdue punishment.
A few minutes later, Jordan returned, the bag straining to contain two quarts of warm, soapy water. Trevor began softly crying as she pulled his wet diapers down and took him over her lap for the third time today. He was so utterly humiliated to be shamed like this and he squealed anew when he felt Jordan pushing more Vaseline into his quivering little hole.
Before long, Trevor was receiving his just reward as a strong torrent of sudsy water was again flowing deep into his rectum.
“Just what a big sissy needs,” Jordan said with obvious satisfaction as she patted his bruised, red bottom.
Trevor moaned weakly, trying to contend with both the growing cramps and Leanne’s superior gaze—she was clearly very happy to see this incorrigible brat punished and humiliated.To be sure, whatever tough-guy image he might have held before, had completely evaporated now and his reputation in the neighborhood would forever be in tatters.
Ten minutes later, the last soapy suds disappeared into the squirming sissy’s bottom as he whimpered helplessly.
Helping him to his feet, Jordan led him to the bathroom where she stood by and supervised his shameful release. Trevor’s cheeks burned with humiliation as she again wiped his messy bottom like a child and led him back to the nursery where a fresh set of diapers awaited him.
Setting him onto the fluffy stack of bunny-soft cloth, Jordan paused long enough to pick up a strange looking device next to the drawer of plastic panties. With practiced movements, she separated the device into two pieces, one which was tube-like and the other which was an irregular plastic ring. Pulling his shy little package through the ring, she positioned it behind his sack and then applied a dab of baby lotion to his tiny little shaft.
“Wha-what are you doing?” he quailed in fear.
“This will ensure you are all safe and secure inside your diapers,” Jordan replied.
Leanne instantly understood the restrictive chastity device that her friend was fitting him for and she grinned down on him broadly with smug satisfaction.
Trevor fidgeted and kicked as Jordan mated the two pieces together, compressing his tiny little shaft inside the even tinier tube (which was more of a cap really, than a tube) and locking them together with a unique, narrow key.
“Sissies that wear diapers shouldn’t be experiencing erections and this will make sure you can no longer masturbate, either.”
Trevor gasped and bit his lip with embarrassment.
If only they knew just how often he played with himself!
“No!” he wailed miserably.
Grasping his ankles together, Jordan swung them up and over his head as her right hand snatched up the paddle and brought it down harshly, swatting his bare bottom with a terrific crack that filled the room.
Trevor howled with pain and desperately tried to kick his feet free from her grip as the paddle slapped each of his defenseless cheeks hard once more.
Sobbing like a baby, hot tears tumbled down his face as she set his legs down and began powdering his diaper area.
“Serves you right, you little brat,” Leanne told him unsympathetically.
Trevor cried softly as Jordan brought the thick cloth up and pinned it snugly around his hips.
“Don’t cry, little sissy,” Jordan said in a syrupy voice meant for toddlers, “these are a bedwetter’s best friend.”
Pulling a frilly pink pair of rubber panties up his skinny legs, Jordan ran her fingers around the waistband to make sure all the soft cotton cloth was contained inside.
Removing the prissy baby dress he was wearing, she replaced it with a fuzzy fleece top with baby bears playing on it. After removing his Mary Janes, she helped him into the crib, tucking a stuffed animal under his arm and pushing another bottle of milk against his pouting lips.
“Make sure you drink that all up, baby boy,” she instructed him as the two of them left the room.
Trevor did as he was told, reflecting on just how far he’d fallen in the space of a few hours. Was he doomed to live the life of a toddler in diapers from now on?
A half hour later, the exhausted youth was sound asleep, clinging to the soft, fuzzy Koala bear in his arms and dreaming blissfully as his bladder relaxed and slowly but surely, released all the milk he’d been given during the day into his thick, fluffy diapers.
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Betty Pearl's Sissy Stories 20.1
Topic: The Terror of the Neighborhood (Read 32987 times)
