Tiffany Johnson took another sip of the dark coffee in the china cup before gently setting it back down on the end table.
Sitting opposite to her, was her good friend Lisa, an attractive woman in her late thirties with long brunette hair and a body that still turned heads. The two were catching up with each other and enjoying a relaxing evening chatting.
Playing on the rug before them, was her 14 year-old son, Tommy, although his present attire certainly would have set him apart from any other teenager; he wore a cropped yellow top with short, puffy, elasticized sleeves that emphasized his soft, toneless arms. His feet were clad in lacy white anklets and glossy yellow Mary Janes but perhaps most conspicuously, was the fat, shiny diaper and plastic panties swaddling his hips.
Tommy was on his hands and knees, pushing his toy truck along before him but as he passed in front of Tiffany, she reached down and gave his soft, diapered bottom a squeeze.
"Feels like mommy's little boy wet his diapers," she announced.
Tommy blushed furiously as he looked away, regretting his close proximity to his mommy's beautiful guest.
"Tommy--am I going to have to start your potty training all over again?" Lisa asked, her voice filled with exasperation.
"Tell me," Tiffany said, changing the subject, "Have you ever considered getting him fitted for a chastity device?"
"Chastity? For Tommy?" she replied with surprise.
The subject of their topic suddenly grew apprehensive--he was only vaguely aware of the concept of chastity but he was certain it wouldn't bode well for him.
"Oh yes, he's passed puberty now--although you'd never know it by his outfit," she chuckled, "and I'm sure he's become quite the little masturbator."
Lisa's features darkened, and she looked down on her diapered son with disapproval.
"You think so?"
"Oh yes, most sissies like Tommy, once they've been put back into diapers, come to find them irresistible. With their hormones raging out of control, they become chronic masturbators and do it every opportunity they can.
"One look at Tommy, and I'm sure he plays with himself several times a day."
Lisa looked shocked and confused.
"Wh-what should I do?" she asked.
"I think you should get him fitted for a secure chastity device as soon as possible. Remember when you told me the other day that you didn't think he was trying hard enough to control his bedwetting? I think it's because he secretly enjoys the feel of his soft, cushiony diapers, and he loves masturbating in them," she explained.
Tiffany reached down and grasped Tommy's wrist, pulling him to his feet. He was blushing a beet red at their discussion and she forced him to sit on her lap. The diapered boy had always been extremely intimidated by Lisa's friend; she was very pretty, with a phenomenal body, and he was always staring at her big round breasts.
Now, as he sat down across her lap, he landed with a wet squish and he swallowed hard, trying not to stare down her low-cut top at her sexy, very adult cleavage.
"How about it, Tommy?" Tiffany asked as she looked at him directly, "Have you been playing with yourself a lot?"
Tommy's cheeks burned all the more hotly and he shook his head violently.
"N-no!" he stammered, although his body language betrayed his protest.
"Tommy...Tell the truth...do you like rubbing the front of your diapers?"
Tommy looked away, unable to hold her gaze. A bead of sweat appeared on his brow.
"Tommy? I asked you a question," Tiffany said has she used her long nailed finger to bring his chin around to face her.
The diapered sissy couldn't look her in the eyes and instead, he stared down at the yawning cleavage between her big breasts.
"Umm, I...uh, well maybe..." his voice trailed off.
"You like to masturbate in your soft, fluffy diapers, don't you?" she pushed him.
Tommy squirmed in her lap. In a match pitting their personalities against each other, Tommy was woefully out of her league.
"Um...I guess," he mumbled, his voice barely a whisper.
"Lisa, as you can see, your little boy is using his diapers to play with himself on a regular basis. The only way to put a stop to it, is to get him fitted for a chastity device and keep it locked 24/7."
Her friend nodded gravely, clearly shocked by these revelations.
"Why don't we change his diapers--I can go out to my car and get a few devices I think will fit him--with any luck, I've got one that's small enough for his little wee-wee."
Without waiting for an answer, Tiffany got up, forcing Tommy to do the same as he stammered and protested what was happening.
"B-but--wait--wait, Mommy," he whimpered.
"Come along Tommy," she said firmly taking his hand, "This is just what you need."
Pouting miserably, Tommy waddled after his mommy as she led him down the hallway to his nursery. He cursed himself that Tiffany had so easily maneuvered him into admitting to his shameful habit. And of course, she had pegged him exactly right--he did masturbate daily, often several times a day, rubbing the soft, cushiony front of his diapers until he'd explode in an eye-crossing orgasm.
And now Tiffany was threatening to take all that away!
Muttering under his breath, a fussy Tommy stood in place as his mommy yanked his damp plastic panties down his legs, tossing them into his diaper pail.
Tiffany soon returned, carrying a medium sized cardboard box in her arms. Lisa unpinned his wet diapers and deposited them in the same container as his plastic panties before sitting him unceremoniously down on his changing table.
Tommy fidgeted as his mommy cleaned his damp genitals with a baby wipe as Tiffany fished through her box of devices.
"I just got one called the Baby Nano that I'm pretty sure will fit him," she said as she produced a very small stainless steel cage and cuff ring.
Tommy squirmed as his mommy placed a thick stack of fluffy white diapers under his rump, his bald little package shriveling in fear. Tiffany took a small dab of baby lotion and rubbed it on the tip of his short, stubby pen-is, sliding the tiny cage over it so that the back ring of it captured his head completely.
The other piece was a hinged piece of steel that when closed, formed a solid ring behind the back of his genitals. Tiffany tugged his sack forward and swiftly positioned it in place, after which she pushed the caged head of his pen-is back to mate with the cuff ring.
Tommy gasped as he stared down at the terrifying device--it compressed his little pen-is completely and he suddenly realized no erection of any kind would be possible.
"Oh!" he squealed as he waved his hands in the air helplessly.
Ignoring him, Tiffany slipped a clevis pin through the holes at the top and added a brass lock, clicking it shut with a broad smile of satisfaction on her pretty face.
"There, my little sissy boy," she said as she rubbed her hands together with smug glee, "No more masturbating for you!"
Lisa bent down and grasped the metal device, amazed at how well it trapped his little package.
"This is really ingenious," she marveled, "This will totally put an end to his erections.
"Maybe now, you'll try harder to stop your wetting," she scolded her son.
Tommy was squirming in place, filled with anxiety as he tried to conceive of a life without masturbation. This was truly a terrible situation!
"And now its diaper time!" Lisa said as she began powdering his front area.
THE END
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Betty Pearl's Sissy Stories 20.1
Topic: The Case For Chastity (Read 17997 times)
