The next morning, Francis was woken by his mom. As usual, his diapers were absolutely soaked, and his mom had arranged a fresh set, laid out on his changing table. After a quick check to make sure his chastity device hadn’t been tampered with, she led him over and sat him down on the thick layers of cotton cloth.
“Francis, it’s become apparent that you have become comfortable with wearing and wetting your diapers every night. I think its time we take stronger measures to motivate you to try harder to stop your bedwetting.
“—Therefore, I’ve decided that you will spend your entire summer vacation in diapers,” she told him firmly.
Tears were forming in his eyes as she laid him down on the soft, fluffy stack of Birdseye cloth.
“B-but, I p-promise to try harder,” he bleated.
“I’m tired of hearing your promises, Francis. Maybe you need a few months of baby treatment to finally convince you.”
Powdering his chastity device and frontal area generously, his mom pulled up the bulky cloth and pinned it around his hips. Francis cried softly in self-pity as she pulled his babyish yellow nursery print plastic panties up and over his diapers. She had made sure to add more layers than usual so that his diapers were even fatter than normal.
Tying his shoes in place, she pulled the prissy top Jordan had made for him over his head and positioned it carefully around his waist, admiring the ruffled hem that remained a couple inches above his diapers.
“There will be some other changes coming around here—We’re going to be converting your bedroom into a proper baby’s nursery with a crib, playpen, and plenty of toddler outfits for you to wear. I’ll be boxing up all your regular clothes up and putting them in the attic until next Fall.”
Hot, salty tears tumbled down Francis’ cheek as he realized that his efforts to stop his bedwetting (insignificant as they were), had fallen pathetically short.
Several weeks later, Francis was over at Jordan’s house, being babysat by his childhood crush. She had been right on board with the baby discipline program from the beginning and she had come to enjoy bottle feeding her prissy nephew with warm milk several times a day.
For his part, Francis was now obsessed with the impositions of his enforced chastity and Jordan’s low-cut tops and short shorts were only aggravating the situation. It was mortifying for him to be seen and treated like an infant by her but compounding the problem was his gnawing libido, unrequited by his complete inability to satisfy his sexual needs. Every time he came in close proximity to Jordan’s big, soft breasts, he licked his dry lips hungrily as his tiny pen-is throbbed anxiously inside his restrictive
Sissy Trainer.
He had repeatedly begged and pleaded with both Jordan and his mom to unlock it, but they had rebuffed him every time. It was very frustrating for the prissy pantywaist to go without masturbating—something he had done every night in his diapers after his mom had tucked him into bed. But now, the self-gratifying pleasure had been taken away from him and he found himself perpetually horny and frustrated.
One day, Jordan had taken all she could of his whining and pestering. She had already given him an enema, but perhaps it was the skin-tight white halter top that she was wearing that was driving him crazy. In any event, his sexy aunt decided it was time to take other measures.
Calling the diapered sissy into her bedroom, she told him in flirtatious but vague terms that she had a special something for him. Excitedly, he readily submitted to having her take his rubber panties down and bending over her firm, silky thighs as she unpinned his diapers.
Taking a fat, pink jelly butt plug, Jordan swirled it in a jar of nursery KY before positioning it at his shy back hole.
“Just relax, Francis, and this will go in a lot easier,” she instructed him.
Not knowing what was coming, the naive sissy youth was filled with eager anticipation.
But as she began applying pressure with the butt plug, Francis quickly realized what was happened and he squirmed over her lap, his hands waving in the air before him.
“N-no! It’s too b-big!” he squealed.
“Spread your legs sweetie, I know you can take it,” she replied as she began exerting more pressure, twirling the soft, slippery invader and pushing harder.
“OHHHHH!!!!” he cried as the fat, malleable jelly plug suddenly slipped past his defeated sphincter, settling inside of him and stuffing him to capacity. It had a very narrow neck, meaning it was there to stay until Jordan decided otherwise.
He was panting as he came to grips with the feeling of fullness as Jordan re-pinned his diapers. Letting him up gently, she pulled his rubber panties up and over his bulky diapers.
“There. That should give you something else to think about,” she told him with her smug, superior smile.
Francis gazed in confusion at her two big round breasts, stretching her thin top to the limits as he flexed his cheeks, trying desperately to expel this strange, new invader. It no longer hurt, but the sensation certainly was foremost in his attention, keeping him occupied and making him feel very emasculated and defeated.
She led him over to the playpen and helped him inside, sitting him down and giving him his dollies.
“There, now why don’t you play with your toys for a while,” she said as she pushed his pacifier into the bewildered boy’s mouth.
After that, Francis’ punishment plug (as it came to be known) saw a lot of use, keeping the frustrated sissy plugged and compliant.