Thanks! The added embarrassment of having to actively participate just seems right for this story ;)

Making some small revisions on the next part now to post soon.

Chapter 3

Nanny gave one of her sweet smiles and took Doug by the hand. “Take off your trousers, sit down on here” she said, leading him to Charlotte’s play mat. “I am Charlotte’s nanny not yours, so you are just extra work. If you want to behave like a baby then you will be treated like one, so you can sit in your wet pants and learn what it feels like to be a baby again. I know this is going to very difficult for you but you will thank us all in the long term, when you can keep yourself under control and not dribble and soil your underwear. However, I am not going to tolerate any outbursts, so you will have to be punished for your rudeness. Now, you will have to stew in your mess until you next need to go to the toilet when we can repeat the exercise all over again.”

“But that could be a long time” whined Doug “I might get a rash”.

“I don’t think so” said Nanny “but to speed up events why don’t you have a drink of juice. Here take this drink that Charlotte didn’t want because it wasn’t in her baby bottle.” Doug looked at the large sippy cup warily but decided not to make a fuss. The ‘Nuby’ cup fizzed and hissed as he greedily suc-ked on the soft silicon spout (half way between a teat and a plastic drinking spout) and the air fought its way back into the vacuum created by his drinking. The twins looked at him open mouthed as Doug looked even more babyish sitting in his wet training pants on a colourful plastic play mat suc-king on a baby beaker which he held by the two large handles. Nanny could not suppress a grin and had to look away before a small chuckle could escape her. She took her mind off things by snuggling her nose into Charlotte’s tummy and blowing a raspberry.

Doug had annoyed her from the very first day that she had arrived. He moaned and moaned about losing his bedroom that had an en suite bathroom. He went on incessantly about how small and dingy his new room was. The walls were pink, his posters would not fit, he had nowhere to put his computer and on and on he went. Eventually Nanny managed to settle in to her new room and arranged Charlotte’s cot and clothing so that the two of them could coexist comfortably in Doug’s old room.

It was true that Doug was in the second division compared to Kate’s family; it was only natural that a mother should favour her own children over that of her partner. The twins naturally doted over their new sister and tended to leave Doug alone. So it was that Doug became more and more isolated as Charlotte took over the family focus. Nanny with the baby, Nanny having planning meetings with his stepmother, and the twins drifting between them all.

Nappies, plastic pants, bibs and baby wear were all over the house. The family bathroom was full of girly stuff, he barely had any room for his toothbrush. Slowly but surely he was feeling ostracised and isolated from what used to be his family home. How he missed his mother and how he resented her new lover now husband who wanted nothing to do with him any more.

So it was decided that he would begin a programme of mischief. He knocked over the carefully folded stack of nappies in the nursery (his old room he reminded himself) and ruffled them up. He took the jar of dummies and hid them under Nanny’s bed, he smeared nappy cream over Nanny’s mirror and shook baby powder all over her jewellery case. Silly, aggravating, pointless acts that thoroughly irritated Nanny.

Around about this time, he started to take less care with his hygiene and even he had to admit that his underwear was starting to take some damage. However, and more worrying, was that all this tension in his life was starting to impact on his sleep. One night he woke up just as he was about to wet his bed. It was enough to leave a patch on his pyjama trousers. He decided that to be on the safe side he would wear underpants under his jammies ‘just in case’ and that is why the staining in these garments was intensified.

Doug had been watching a programme created for young children and was watching with Charlotte because there was nothing else to do. He had been told not to move and was following instructions until his bladder started to send urgent messages. What should he do? Go and find Nanny, make a run for the toilet, shout for help? He decided to call out.

Nanny appeared much to his relief, her hands full with a basket of freshly laundered nappies that she was taking outside to hang on the line. “I’m just going to hang out Charlotte’s nappies, then I will come straight back and attend to you” she said, secretly pleased to see the boy in huge discomfort. Doug looked distraught at this news as he was very close to reaching the end of his bladder’s tether. However, there was worse to come and his previously quiet rear end was now starting to protest very loudly. A break of wind trumpeted an intense desire to release. He rose to his knees in an attempt to prevent a disaster. He looked through the French windows as Nanny completed hanging the tenth nappy, the basket was still half full and there were still the plastic pants to hang after the terries.

Part 4

     â€œOh Diane,” Susan spoke up, “I was thinking that it might be nice for Jamie to help you with Bobby’s finishing touches.” She elaborated, “after all, Jamie caused his fair share of problems last time too.”

     â€œThat’s a wonderful idea Susan!” Diane agreed. “Why don’t you come up here with me Jamie?” 

     Jamie looked at his mother in silent protest, but she simply smiled back and said, “Go ahead, dear. It will give you a chance to get a closer look at Bobby’s dress. I’m sure you must be curious!” Then she added, “you seemed to follow along with him so eagerly before; this will give you another opportunity to ‘team up’ with him!”

     Horrified, Jamie realized that he’d better do as his mother wanted. The unspoken threat was that he might find himself in a dress too! Slowly, he got up from his chair and walked over to Mrs. Green and Bobby. The two boys locked eyes again. Bobby seemed even more humiliated.

     â€œHere you are dear,” Mrs. Green said as she handed him a very elaborate blue and white hairbow. Jamie held the girly hairbow very tentatively as he stood next to his humiliated classmate.

     Noticing how gingerly he held Bobby's hairbow, Mrs. Green said teasingly, “It’s not going to bite you dear!” Several of the ladies chuckled again at that.

     With Mrs. Green’s guidance, Jamie stepped in front of his friend and fastened the oversized hairbow in Bobby’s curly blonde hair. Jamie’s hands trembled due to the awkwardness of the situation as he leaned over his classmate so closely. Bobby’s hairbow had a large alligator clip underneath to hold it firmly in place, but Mrs. Green insisted that Jamie add a couple of additional clips to hold it tightly in place for “extra security.”  Being forced to take such an active and personal part in his friend’s sissification was an awful feeling, and both boys had a swirl of emotions wash over them. When Jamie finally got the hairbow placed to Mrs. Green’s satisfaction, he stepped back immediately. Now, thanks to his classmate, Bobby wore the darling blue satin hairbow with lovely white lace accents in his curly blonde hair. He looked even more girlish and adorable now.

     â€œIt’s a shame his hair is still too short for more suitable styling,” Mrs. Green observed, “but I’ve decided that he’ll grow it out, so soon we’ll be able to put him in some proper curls or pigtails!”
 
     â€œOh, even with the shorter hair, he’s already so precious with that gorgeous hairbow!” Jamie’s mother exclaimed. Several of the ladies nodded in agreement. 

     It was then that Jamie realized how similar the colors of his outfit were to Bobby’s party dress. Their mothers had coordinated their clothes! Then he belatedly became aware that Daphne had been taking pictures the whole time with her phone! He blanched at the thought of any of his other friends from school seeing photos of this. He and Bobby would never live it down! Jamie wanted nothing more now than to run back to his chair and get as far away from his girlified friend as possible, but he quickly found out he was not done yet.

     Daphne put her phone down and next and handed Jamie a tube of lip gloss. “Here you go, Jamie” she said sweetly, “Bobby needs a touch of color to brighten up his look!” Daphne proceeded to guide Jamie in applying a lovely coat of understated pink lip gloss to his friend’s lips. She had her little brother pucker up and then supervised closely as Jamie was forced to apply Bobby’s lip gloss for him. It was an uncomfortably intimate thing to do, and both boys’ stomachs jumped repeatedly as Bobby’s lips were carefully coated with the creamy pink lip color. When Jamie was finally done, Daphne instructed Bobby to roll his lips together several times to get his lips thoroughly coated. Then, she had Jamie get a tissue and lightly blot Bobby’s lips to remove any excess. Jamie was left holding the tissue with his friend’s pink lip print on it. It nearly made his skin crawl. Meanwhile, Bobby’s lips were now a darling shade of pale pink.

     â€œThat’s perfect,” Daphne said with approval, “Your lips are so kissable now little brother!” She added, “and the good news is that’s a long-lasting lip stain, so that color should last a good day or two!” Addressing Jamie, she asked teasingly, “perhaps you’d like to try some too?” Instinctively, Jamie shook his head furiously.

     At this point, Jamie realized that his mother had her phone out as well. Every bit of this horror show was being captured in photos! Then his mother spoke again, seeming a bit carried away in the moment, “Oh why not Jamie? You ought to get a little taste as well. After all, what’s good for the goose is good for the gander!”

     Caught by surprise and seemingly unable to speak, Jamie stood motionless for a moment. Before he fully comprehended what was happening, Daphne had grabbed his chin and began putting the pink lip gloss on him too! It felt so slick and creamy on his lips, and it had a sweet strawberry taste. He felt so helpless and emasculated in that moment. She had him roll his lips just like Bobby had done, and then she had Bobby blot Jamie’s lips with a tissue just like he had done to Bobby moments ago. Then, Daphne picked up a small hand mirror and held it so Jamie could see the results. Jamie gawked in dismay as he saw how girly he looked with his fresh pink lip gloss!

     â€œAww,” Daphne said with a little chuckle, “that’s adorable, Jamie! Now you’re just as sweet and kissable as my darling little brother!” 

     Bobby looked as if he wanted to cry, and Jamie realized he was still holding the tissue with Bobby’s pink lip prints between his fingers. Jamie wanted to sink into the floor.

Chapter 2

A large box of plastic pants lined with thick terry towelling arrived within days along with the biggest pink potty that Doug (or Nanny) had ever seen. They were identical to the first stage nappy pants that would be used by a toddler in the first weeks of potty training but a size appropriate to a young teenager. Nanny unpacked them and stacked them in a huge pile next to the huge stack of terry nappies that were used by Charlotte during the day, moving her larger thicker night time nappies further along the shelf. The two piles of fluffy terry helped to disguise the new stack of protective wear. Twelve pairs of lined plastic pants now stood as tall as the stack of over twenty daytime nappies.

Also delivered was what Doug assumed to be some sort of yoga mat or agility mat, but was somewhat surprised when it was unrolled to see that is was covered in a babyish design with little teddies wearing nappies and was clearly designed for changing very large children.

“Let’s get started, trousers off, pants off, lie down, arms back behind your head and legs wide on the mat please,”ordered Nanny. Doug did as instructed and before he could utter a word he found himself being shaved with an electric razor until he was baby smooth. He was turned and manipulated until all signs of any hair had been totally erased. “Now you need to be protected from any rashes” said Nanny rubbing in a thick white cream that barely was absorbed into the skin leaving a thick white residue that was sticky and oily.

“Lift up” she commanded flapping out one of the new pairs of underwear as she pulled them up his legs and over his bottom. The towelling protection was soft and comfortable, it almost felt sensual as the soft vinyl rustled quietly but noticeably. “All done, upsydaisy, trousers on and tuck in your shirt”.

The trousers barely fit over his new protection and every move came with an associated rustling. He looked in the long mirror that Nanny used to check her immaculate uniform each morning and he could detect the padding about his loins. Charlotte who had been taking a nap in her cot chose the moment they had finished to awake from her slumbers. Nanny sprang into action and made for the baby. “Off you go Dougie” she chirped “when you need to go, you must ask me for your potty so we can practice your exercises, but you must leave it until the very last moment like your mother explained. Now I know it might be difficult in front of the others or in company, so you must ask me if you could have a ‘private word’ with me in the nursery. This is the way we can keep it all a secret.

The two girls, Charlotte in her high chair, Nanny and Doug all sat at the table for a lunch of cold meats and salad. Charlotte wore her pink bib with the little lamb on it and ate her chopped up meat and bread cut into narrow slices with her stubby little finger. She stopped at intervals to drink from her baby bottle which she preferred to use over her sippy cup. The twins were in mischievous mood and like most teenagers were eager to make mileage out of what they had seen.

“Doug seems to be looking a bit chubbier today” said Hannah. “he looks like he is wearing a nappy” exclaimed Gina. “Or perhaps he is back in training pants” giggled her twin sister. “I heard a definite crinkly noise when he sat down” said the other, reaching out a hand to probe the person sat next to her. “Oh my goodness! He is wearing a nappy, I can feel his plastic pants”.

Doug shot up in a state of shock.

Nanny immediately stepped in “Doug has a problem with is waterworks and is very brave to try and make it better with some exercises that your mother has instructed him to perform. Now sadly that will mean that he will have to wet himself a little bit, while he tries to strengthen his muscles. Now I think he is being very brave and you should not make fun of him please”.

The twins apologised, Doug who was blushing intensely sat down and everybody tried to ignore the crackling of his plastic pants.

By mid afternoon the pressure in Doug’s bladder had reached a crescendo and he was getting desperate and summoned Nanny to his aid. They went to the nursery as the twins played with their sister. Doug was writhing with the urgency and clutching himself in order to prevent any leaks. Nanny calmly unrolled his changing mat and positioned the enormous pink potty in the middle. Doug was becoming frantic and could already feel a warm dampness creeping into his new pants.

“Nanny, I’m starting to go”, he warned “I don’t think I can hold it very much longer”

“One more minute, then I will count three, two, one and you will release as I count one thousand, two thousand, stop and then you will clamp down. We will then pull down your pants and we will sit you on your potty and you can finish doing your wee wee.

Doug was almost crying as Nanny started her count down. On the words ‘one thousand’ he released and a flood poured into his underwear, hot, streaming it radiated out beneath his hand, ‘two thousand’ and he was in full stream, ‘stop’ and he tried with all his might to clamp down on the flow but it continued for another second or so before he managed to control it. Nanny brushed away his hands to reveal the front of his plastic pants showing the wet yellow towelling contained within. She pulled down his pants and slipped the potty under him as he squatted down. He had not fully shut down his release and as soon as his bottom hit the rim of the potty he finished off the performance. There was as much wetness in his pants as there was in the potty.

“Pull up your pants, I’ll change you shortly, but I need to measure how much you have saved for the potty so that we can see whether you are improving or getting worse as time goes on. Nanny measured the volume and emptied the potty down the toilet that was en suite to the nursery.

Doug felt the freshly wet towelling against his skin and couldn’t wait to wear a clean pair of training pants.
Suddenly there was a shout from downstairs followed by a cry from the baby. “Follow me!” shouted Nanny as Doug was forced to pull up his trousers and tuck in his shirt as they ran down the stairs. In the lounge the twins were comforting their sister who had stabbed her foot on one of her toys.

Nanny picked her up and immediately noticed that the shock of her little accident had cause her to soil her nappy which was usually quite a rare event these days. She comforted Charlotte patting her back and cuddling her to her breast where the crying slowly subsided into sniffles.

The twins turned their attention to Doug who was still trying to tuck his voluminous pants into his trousers and secure the zip on his fly. They could clearly see that not only were his pants wet but that the smell of his accident was also detectable. He looked so miserable that they decided to say nothing, it couldn’t be any fun being in his position.

Nanny seemed to be away for ages and when she returned, Charlotte was sweetly smelling of baby powder and luxuriating in a fresh, clean, fluffy, dry nappy. This was a long way from Doug who was stewing in his damp, smelly prison wrapped about him.

As Charlotte was being put in her play pen Doug had a sudden burst of rage and shouted out “what about me? You only care about HER, you never care about me. I am going to change myself because this is stupid and I am not doing it any more. He stamped his foot petulantly and Nanny was not impressed. The consequences of his outburst were not going to be liked…….

Note: A prequel to a previous story can be done!

Fun beginning! Except I think Doug may wind up getting potty UN-training LOL!  I think there's a great chance he regresses while baby sister progresses!

I think so as well, but said it the way I did because I can see him having to follow little sisters schedule for a bit before nanny makes him wait longer and longer until he loses control