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Author Topic: A New Family Dynamic  (Read 77933 times)

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CuddleBunns

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Re: A New Family Dynamic
« Reply #84 on: July 02, 2020, 04:03:43 PM »
Part 27

 The sound of Lilly's rumbling stomach could be audibly heard from the back of Jessica's car as the two of them continued to drive down busy streets. It was around 2pm now, which was about two hours after Lilly normally ate lunch. To make matters worse, it was now around the time that Lilly would usually be at home napping in his crib. These factors combined were beginning to make Lilly somewhat cranky, a fact that Jessica's many years of experience in childcare made it easy for her to pick up on. To help stem his hunger and possibly soothe him to sleep, Jessica had given him a bottle of formula from home that she had brought with her in her diaper bag, as well as put on a CD of children's nursery lullabies over her car stereo. The formula certainly helped, but the lullabies did nothing to soothe Lilly's temperament, and in fact was probably only serving as an annoyance to the poor sissy, who dearly missed the sounds of the various bands and artists that he used to listen to.

 Jessica adjusted the rear view mirror so she could get a better glimpse of the tired, carseat faring baby behind her. "I'm sorry precious, I know you're very tired and hungry. Big sis is looking for a restaurant that we can go to right now, then I'll feed you a nice lunch before we go do anything else. For now, just try to get some rest", she said to Lilly, who continued to gulp down formula with an impatient, cross look on his face.

 The formula would begin to do its trick however, and Lilly soon found himself hypnotized by the passing bumps in the road that were slowly massaging him into an increasingly tired state. As the last of the formula exited the bottle, Lilly soon felt his eyes droop and he became lost into a state of deep, well earned sleep. When he finally awoke, he found himself not safely tucked away in his car seat as he remembered, but instead being carried in Jessica's arms through some sort of parking lot. "Mfffm mmmph", the audible sound of his grunts were quickly muffled by his pacifier, which Jessica must have re-insearted into his mouth at some point after he fell asleep.

 "Oh hey sis! You're awake", Jessica beamed to him with a cheery smile, "I finally found a place where we can have a nice lunch. Hope you're still hungry!"

 Lilly quickly turned his head around and noticed the large brick building behind him. It was festively decorated with big glass windows featuring green shudders as well as a large, two sided front door at the entrance. "Great", Lilly thought, "This must be an Applejacks". The smell of sizzling entres and fresh salad dressing immediately hit his nose as Jessica pushed the front doors open and the two of them entered into the restaurant. They were promptly greeted upon their entrance by an overly enthusiastic server, a somewhat plump young woman who looked about Lilly's age (although obviously not the age that Lilly looked) with a gigantic, unnatural smile plastered across her face. "Hello, welcome to Applejacks, your neighborhood's favorite bar and grill! Will your little one require a highchair this evening?", the server practically yelled out with so much enthusiasm that it immediately made Lilly start to feel uncomfortable.

 Jessica smiled at the server and nodded her head. "Yes please, and if we could possibly get a booth that would be great", she politely responded. The served grabbed a high chair from the corner and guided them to a booth near the side of the restaurant. It was seemingly the only booth left in the whole establishment, surrounded on all sides by lots of busy tables that we're absolutely chopped full of people. Lilly felt himself growing more and more embarrassed by the second as his server placed the small plastic high chair at the booths end and Jessica guided him in. It was a very tight fit for Lilly, but he was just barely able to fit into it with the tray locked into place, although he was basically left with no breathing room to speak of. The server quickly headed back and grabbed two menus from her stand. The first one was a large adult menu, obviously meant for Jessica, while the second was a tiny paper children's menu plastered with pictures of cartoon animals and simple games to entertain children while they waited for their food. There was no question who the second menu was for.

 The server returned and handed Jessica her menu before turning to Lilly and placing his menu on the tray of his high chair, along with a pack of crayons. "I know she probably cant read", the server said thoughfully, "but I figured your little one might like to color while she's here. Can I start you off with anything to drink?"

 Jessica looked at the menu for a few seconds before deciding that nothing caught her interest. "I'll just have a water, and if you don't mind...", she trailed on while digging in the diaper bag for Lilly's empty bottle, "could you please fill this up with milk for the baby?"

 The server grabbed the bottle from Jessica's hand and gave her another large, unnatural smile. "Certainly! I'll be back with your drinks in just a minute!" Before she could leave, however, Jessica quickly tapped the servers shoulder to once again get her attention. "Oh sorry, one more thing", Jessica said with a mischevious smile, motioning to Lilly with a sly, casual wink. "Its her birthday today!"

 The server gasped and slapped her hands against her cheek. "Wow! Well happy birthday sweetie!", she told Lilly in an over the top, exited voice. "I'll bet you're so exited to be another year older today!"

 Lilly looked over at Jessica in complete confusion. Although it was becoming increasingly difficult for Lilly to gauge he passage of time, he knew there was absolutely no way it was his birthday right now. But why would she say that it was his birthday when it clearly wasn't? The server traded a few more pleasantries with Jessica before quickly leaving to grab their drinks. When she eventually returned, she handed Jessica a glass of water as well as the full bottle of milk as had been requested, and still seemed just as overly cheery and optimistic as when they first saw her. "Do you need anoyher minute to look over your menu? Or would you like to order now?", she asked with more enthusiasm than was necessary.

 "I'm ready to order now, thank you", Jessica immediatley responded. "I'll have the steak fajitas with peppers and onions, as well as a side of fries. Make the steak medium rare if I have the option." The server jotted down her order before looking over to Lilly. "Anything for her?", she asked Jessica curiously. It was clear to Lilly that the server must believe him to be an actual infant, as she seemed to talk to Jessica about him as if he couldn't talk or make any choices for himself. She was absoultely right about both of those assertions, of course.

 "Oh it's all right, I already have some food for her with me. Thank you though", Jessica replied. The server then took their orders back to the kitchen to be processed, leaving Lilly alone with Jessica as well as the sea of nameless strangers that surrounded him. As he waited for the food to come, he felt the curious gaze of many of these strangers point in his direction, making him more and more uncomfortable. Jessica paid his worry no mind and eventually began to dig through his diaper bag, producing a sissyish pink bib, a jar of baby food, and a small plastic spoon. She strapped the bib around Lillys neck and started undoing the lid on the baby food, scooping up a small bit to present to him.

 "Alright baby, I'll just feed you your num nums now so you don't get hungry", she told him tenderly. She brought the spoon full of infantile mush up to his face and tried to shovel some into his mouth. Lilly noticed that some of the tables around them were starting to watch the spectacle at hand, and tried his hardest not to accept the food being offered. Because of his reluctance, the spoon would instead meet his closed lips, smearing colorful baby food all over their sides as Jessica tried to force her way in. "You silly baby, you know I'll have to spank you if you don't open up, so start eating your food right now. I'd hate to make a scene", Jessica said to him in a stern, dissapointed voice.

 Sensing that a spanking would be a much worse alternative, as well as attract more unwanted attention, Lilly soon realised he had no choose but to accept the meal he was being offered. On her second attempt to shovel food into the pathetic sissy's mouth, Lilly finally accepted Jessica's spoon full of mush and closed his eyes in embarrassment, reluctantly swallowing it down. "Good gir! That's more like it", she praised, continuing to feed him spoonfull after spoonfull from there on after. By the time she was done, his face as well as his bib were absolutely coated with baby food.

 Just as she was about to clean him up however, Jessica turned around to face the isle, where she noticed a lot of commotion going on. A gigantic grin soon appeared on her face when she realized what was about to happen. In addition to their server, who was quickly approaching with Jessica's fajita platter, there were about three or four other employees trailing behind her carrying sparklers and balloons. Jessica knew what was about to happen was a bit cruel on her part, but the the thought of it gave her too much joy to care. She could not wait to see the look that would appear on Lilly's face in a few seconds.

 Lilly soon noticed the racket as well, but before he could even turn around, he was immediately surrounded by a sea of Applejacks employees, each one with an elated, celebratory look on their face. They began to sing at the top of their lungs in unison:

"Happy Happy birthday!
From all of us to you!
Happy Happy birthday!
Hope all your dreams come true!"

 The employees clapped their hands while joyfully repeating the stansa two or three more times, causing Lilly to almost shut down completely in shock and embarrassment. By now, the entire restaurant was staring in their direction, watching with entertained expressions as this sissy boy, who was clearly not an actual infant, was forced to endure more unwanted attention than any sane person could ever ask for. A few scattered laughs could now be heard throughout the restaurant, with the topic of most conversations soon changing to the scene that was going on at Jessica and Lilly's booth. It was all so overwhelming to Lilly; The singing, the clapping, the stares and the sparklers, that he was completely helpless to stop himself from wetting his diaper in fear from all the intense stimuli surrounding him. This only made him more upset, and he wanted nothing more than for all of the attention to stop.

 Eventually the signing would stop. Although it had lasted maybe all of 30 seconds, Lilly felt like the ordeal had gone on for hours, and was exhausted and trembling by the time the commotion ceased. Not a second after the song finished however, an employee pulled out a Polaroid camera and snapped an instant photo of the upset sissy, who's face was still absolutely caked with babyfood, and who's wet diaper could very clearly be seen under his fluffy pink skirt in his high chair. She then showed the two of them the photo, before taking it and tacking onto a section of the wall that was labeled "Birthday Wall of Fame". It was all highly amusing to Jessica, who was looking on with an expression of pure, unadulterated joy as the entire thing progressed. She thanked the employees for their extravagant show and promised that she'd tip them well. Even after the employees left, all eyes would seem to remain on Lilly for the rest of their meal. He sat there stupified in frozen terror, forced to watch Jessica eat sizzling fajita after sizzling fajita as he gulped down his bottle and felt his diaper grow colder and colder by the minute. By the time Jessica paid the check and left, he was happy to be strapped back into his carseat, ready to leave this entire humiliating experience behind. He wondered what his sister had planned for him next, and hoped that it wouldnt be nearly as embarrassing as this whole experience had been.


Sissy Little Girl

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Re: A New Family Dynamic
« Reply #85 on: July 02, 2020, 10:23:35 PM »
CuddleBunns, All I can say is, "poor Lilly."  Having endured the embarrassment of the theater, she now had to endure lunch at AppleJacks.  That wasn't mortifying enough for Lilly, she gets fed a bottle, baby food and then has a surprise birthday celebration by the waitresses.  No wonder that Lilly wets herself so much. ;) ;) ;) ;) ;) ;) ;) ;)


CuddleBunns

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Re: A New Family Dynamic
« Reply #86 on: July 03, 2020, 11:04:11 PM »
Part 28

 Once again, Lilly found himself strapped into his car seat as Jessica continued to drive down the road to an unspecified location. He wondered internally where they were even going, as Jessica had given him no such information and didn't seem particularly interested in keeping him "in the know". Ever since he had began his transformation into a little girl, nobody seemed to bother telling him any relevant information anymore unless it was absolutely necessary, figuring it was all beyond his control anyways. Now that he was not even allowed to ask questions, Lilly was finding himself more in the dark than ever, subject entirely to the whims of those around him.

 His questions would soon be answered when Jessica pulled into a nearby plaza and parked the car near a large brick building that appeared to house many stores. The closest of such stores featured a sign much larger than the others surrounding it with pictures of toy blocks that spelled out "Howe's Toys, Games, and Books". Lilly did not know for sure, but he had a hunch that this would be their next destination. Jessica began to hum to herself as she turned the car off and began the process of removing Lilly from his carseat. As she was doing so, she noticed that his diapers looked a bit wet, and decided to give him a quick diaper check before they headed into the building.

 "Lilly! When did you wet yourself, baby girl?", she said in a surprised tone, feeling the dampness of his diaper against her finger. Lilly expected her to give him a quick change, but she instead simply unbuckled him and threw him over her shoulder. He could certainly take more wetting, she figured, and knowing his body's scheduel there would soon be another suprise present in his diaper, on account of the time that had passed since she had fed him. Jessica closed the car door and began to make her way to the front of the building, where there were a selection of carts assembled for customers to grab at their leisure. She studied the carts for a second before deciding that none of them would be large enough to seat Lilly inside of. A sad frown soon appeared on Jessica's face, realising that the adorable image in her head of her feminized and babified step brother being pushed around in a cart like a true toddler girl would not become a reality. That is until she noticed a second rack of carts out of the corner of her eye. These carts featured two large plastic seats on the end for slightly larger children, almost as if they were a mix between a stroller and a cart. She decided to try her luck with these and placed Lilly into one of the plastic seats, standing back for a second to give it a good look. Lilly looked a bit large and silly sitting in the tiny seat that was clearly made for children much younger than him, and the buckles holding him in seemed very right and uncomfortable, but otherwise it was a perfect fit. Jessica's frown disappeared when she realised that she would get her wish after all, and she began to push the cart inside the store with a very satisfied look on her face.

 As the two of them entered the store, Lilly looked on in amazement at the ocean of colorful cardboard and plastic that began to surround them in every direction. Toys, board games, video games, and children's books of every type seemed to line the isles to infinity in every corner of the gigantic retail establishment. Jessica immediatley seemed to notice the twinkle that had appeared in Lilly's eyes. She began to speak to him in a cheerful, positive voice. "Like what you see little sis? Since you've been so good, big sister is going to buy you a nice little treat! Do you like the sound of that, baby? Does wittle Lillykins want a nice new toy?"

 Lilly gave her a smile at the positive attention, but was caught off guard when he felt the cart come to a complete halt. Jessica's smile had disappeared, and she now looked at him with a cartoonishly exaggerated frown. "Aw, so you don't like the sound of that after all? Baby sis doesn't want a nice new present from his big sister?"

 Lilly remembered what had happened earlier at the movies and realized that she most likely wanted him to respond with some sort of baby talk. He mentally prepared himself for the humiliating gesture he was about to partake in, before removing his pacifier and looking directly up into Jessica's eyes. "Da! Da! Da! Goo!", he yelled out in the most ridiculously sweet and babyish voice he could muster, forcing the best look of excitement on to his face that he could. Jessica's smile quickly returned to her face upon seeing the childish gesture. She brought her hands up to her cheeks and pressed them together, tilting her head and giving Lilly one of those cutsie faces that one uses to entertain a toddler. "Awww so wittle sis does want a pwesent!", she said in an equally cutsie voice, "Otay baby! Only because you're soooo cute!"

 Jessica continued pushing the cart down the aisles until she came to a section that was absolutely filled to the brim with baby dolls. She studied the aisle curiously and began to grab a selection of baby dolls off of the racks. She held three select ones up to Lilly's face gave him an exited look. "I know it has to get sooooo boring sitting in your playpen alone all day. That's why I thought it would be great if I got you a pretty little friend to play with. It'll be so cute watching you hold a little dolly and rock it in your arms. You'll finally get to know how me and mommy feel! Any preferences, sis?"

 Lilly looked over the options in front of him and pointed to the doll in the middle. It had blonde curly hair and a cute purple dress with lots of ruffles, as well as a puffy white diaper that flared out from under the dress. On the front of the box sat a big pink nametag featuring the words "Hello mommy, my name is Ashley". Jessica gave a second look at the doll and nodded approvingly. "Ashley, huh? That's a very pretty name for a very pretty dolly. Good choice little sis!"

 Jessica returned the other dolls to the rack and handed the one Lilly had selected to him, instructing him to take the box in his arms and give it a big hug. Lilly knew it would look quite rediculous, but complied with her demands anyway. In actuality, even though he knew deep down that he shouldn't be as exited as he was to receive a baby doll as a present, he had reasoned that it would at least be more fun than the extremely simple blocks and other baby toys that his mommy forced him to play with. There was also a part of him that had come to enjoy the dolls he often played with during his frequent visits to Sophies house, and he had secretly been wanting one of his own for a long time. He did not know why, but something inside of him was making him feel much more soft and nurturing lately, and the games he was beginning to imagine when left to his devices were begging to reflect this sudden change, often taking on much more of a domestic bend than they had before. This was a point that deeply embarrassed Lilly, however, who was in deep denial about how much he had actually psychologically sunken into the roll that had been chosen for him by everyone else that still remained in his life.

 Lilly continued to hold the doll close as the cart made its way to the other end of the store, which housed a small, well-decorated area with slightly lower shelves filled to the brim with children's books. Jessica began to browse the shelves and select various picture books of all different types, throwing them into the cart when something good caught her eye. She noticed Lilly looking on curiously as she carried out her shopping, and gave him a light pat on the head. "Sorry baby", she said with a slight tinge of regret, "but these books arent for you. We're running out of books to read for storytime at the daycare, so I need to find some new ones so the children don't grow bored. If you want I could give your mommy some of the old ones we've already read. I'd love to come over and read some to you sometime".

 "Guu!", Lilly responded happily with a large smile. Even though his sister was no stranger to humiliating the poor boy, Lilly greatly appreciated the lengths she went to show her love for him. She seemed to genuinely like being around him and nurturing him in a way even Andrea didn't always seem to, and despite his occasional anger at his sister's schemes to expose and humiliate him, during times like this when she was nice to him he had begun to subconsciously try to make her happier. His sister returned his affectionate gesture by lightly pinching his cheek and giving him a heartfelt, adoring look. "Awwwww you're too cute for words. I love you baby girl."

 After Jessica felt satisfied with the selection of books she had chosen, the two of them soon found themselves stuck in a long line as they waited to be cashed out. Lilly could not help but trade glances with the people waiting behind them, who were looking at him with skeptical glares as if something seemed off. The genuine feelings of acceptance and happiness he had felt just minutes before were now beginning to wear off, and the unnaproving stares of the other patrons were sending his brain crashing back into reality. Jessica noticed his expression was becoming much more reserved and shy, and after spending so much time together was beginning to feel a little bad about it. She reasoned that she had humiliated him enough today, and figured that it would probably be best to get him back home as soon as she could to spare him any more hard feelings. It would still be absolutely necessary to break him down enough that he would act like a total infant in public, she figured, but also knew that if she pushed him too hard it would do nothing but make his intense feelings of shame and anxiety worse. A nice session of tender cuddles in Jessicas lap was definitley in order for Lilly when they got home.

 Eventually they got to the front of the line and placed their items on the counter to be wrung up by the cashier. The cashier looked at Lilly the same way that the other patrons had, but thankfully did not make any rude comments and carried on with their transaction as normal. Once everything was properly scanned and paid for, Jessica gave the cashier a polite goodbye and finally pushed the cart out the front door and into the parking lot, much to Lilly's relief. The cart slowly made its way across the lot before reaching the rear side of Jessica's car. She unlocked the trunk and began loading bags full of the books she had bought into it, but left Lilly's new doll out for him to once again hold onto. When it came time to finally load Lilly into the back and place him in his car seat, she instead shocked Lilly by picking him up into her arms and enveloping him into a big hug. She rocked his body slowly in the air and began to speak tenderly into his ear. "Thank you Lilly. I seriously mean it. You were so good for me today and I absolutely loved spending this time with you. I know it's not easy for you to act like a baby in public, but I want you to know that I love you and I would never let anyone try to hurt you."

 She then opened the door and buckled him back into his car seat, giving him a light kiss on his forehead before closing the door and climbing through the front door into the drivers seat. She adjusted her mirror so she could look at him and continued speaking softly. "I want you to know that... it's okay to be yourself, little sis. I saw how you looked when you were watching the movie earlier; How you cuddled into my lap and held on tighter when you got scared that someone would see you. How your face lit up when I showed you that little baby doll and told you it could be yours. As much as you try to fight it, I know deep down in your heart that you know this is exactly what you want, and what you've probablg always wanted. Otherwise why would you have said so in your journals? When we get home I want to have a serious talk with you. It's not anything you should be afraid of. I won't degrade you, or humiliate you, or make you do anything you don't want to do. I just want to have a heart to heart and listen to how you have to feel about things. Is that okay Lilly? Will you do that for me? Will you please let me help you?"

 Lilly felt very emotionally conflicted at everything his sister had to say. As much as he wanted to fight it, she was right about absolutely everything. Strong feelings began to overwhelm Lilly, and his eyes began to water as he tried to muster up as much of a response as he was allowed to give. "Guu-", he shakilly spat out before being cut off by his step sister.

 "No baby, you don't have to use baby talk right now. For the time being I'll let you speak to me like a big person, as long as you promise to be quiet for the rest of the car ride and think about what I said. Despite how you may feel, me and mom only want to help you, and we can't do that unless we figure out a better way to let you help yourself."

 "Alright Jess", Lilly replied through uncertain tears, "I'll do that. Thank you so much."

 Jessica flashed him a warm, sympathetic smile through the rear view mirror. "Thank you baby. Just suc-k your pacifier and think long and hard about what you really want. No more words until we get home, then I'll let you talk as much as you want to. Big sis loves you, and she just wants you to love yourself as much as she does." Lilly nodded and stared out the window deep in thought, trying desperatley to come to terms with himself as the two of them began to make their way back home.

CuddleBunns

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Re: A New Family Dynamic
« Reply #87 on: July 04, 2020, 01:17:00 AM »
Part 29

 Butterflies were swirling around in Lilly's stomach when the car finally pulled back into the driveway of his house. He knew his sister would soon force him to confront his feelings, and she had a tendency not to mince words. Jessica turned the car off and grabbed him from his carseat, looking down at him with a great deal of empathy as she brought him inside and placed him on the couch. She reached down and grabbed the box containing his new doll and opened it for him, handing him his new toy and giving him a light smile. "No need to be scared baby, everything will be alright. I want you to hold your doll close so you feel comfortable while I go and grab some things. I'll be back in one minute and we can have a nice long talk."

 Lilly instinctually held his new doll tightly while he waited for Jessica to return. He did not know why, but the sensation of holding on to something was actually having a legitimate soothing effect on him, and as much as he knew he was playing right into Jessica's plans by doing so, the calming effect it had on his anxieties made it very hard for him to stop. Eventually, Jessica re-appeared in the living room with a serious expression on her face. Jessica could sense that he was experiencing a great deal of negative feelings, and knew that she would need to tread lightly. She sat down on the couch next to Lilly and pulled him into her lap, wrapping her arms around him and giving him a big comforting hug.

 "Okay Lilly, I'm going to remove your pacifier and let you talk now, but you need to promise me that you're going to be positive and civil. Remember that I only want to help you, and I want you to be as honest with me as you possibly can. I'm still technically in charge right now, and I can still decide to punish you if you decide to act up and treat me badly. Alright?", Jessica asked Lilly in a firm, yet still empathetic tone. Lilly nodded and felt Jessica pluck his pacifier out of his mouth.

 "What did you want to talk about Jess?", he asked her in a nervous voice. It felt weird hearing his own voice form an actual sentence like that, it had been so long since he had been allowed to.

 Jessica felt the nervous tone in his voice and tried to speak to him as calmly as she possibly could. "I want to talk about you, Lilly. I want to know why it's still so hard for you to accept who you really are."

 "What do you mean accept who I really am?", Lilly said in an obviously upset voice. It was going to be hard for him to keep his emotions in check after everything that had transpired, but he knew he had to try. He attempted to dial back his anger as he continued to speak. "Im a 19 year old boy in a dress and a diaper, Jessica. No matter how much people insist otherwise, that's all I'll ever be. I know you and mom just like humiliating me, making me feel like I'm pathetic and insignifigant. Well you know what? It's working. It's...It's..."

 Tears were now falling rapidly down Lilly's face, causing Jessica to shake her head and cuddle into him deeper. She began to massage his belly and spoke to him in a sweet, but stern tone. "No baby. You know what's actually pathetic? Someone who ignores something so obvious and lives in denial when all the signs are right there in front of their face. Let's face it, you asked for all of this. Maybe not directly, but if you didn't want it then why would you fill an entire journal with pages and pages about how you 'don't feel like a man' and 'wish you could be a baby girl'? You're the one who wanted to wear diapers. You're the one who wanted to be called Lilly. You're the one who wanted to be dressed up in pretty clothes and dotted on constantly by me and mom. That was all you. So don't pretend this is some horrible punishment for you because we both know it's not. Me and mom just want you to accept yourself for who you really are so that you can finally stop sulking and feeling bad about yourself."

 Lilly looked back up at Jessica with an appearance of extreme embarrasment. Tears were still continuing to fall down his face at a greater and greater intensity. Eventually he would crack, but Jessica knew that before that could happen, it would be a long fight. "If you're only doing this out of love, then why do you humiliate me so much? You never cared for me before, you let me know as much almost constantly. Why am I supposed to buy that either of you actually care about me now?", Lilly said in a shaky, tear filled voice.

 Jessica gave her head a small shake and lifted him up so his eyes could directly stare into hers. She gave him a deep, comforting hug and patted his back lovingly in a rhythmic fashion. "Baby...", she began in a thoughtful, empathetic voice as she searched for the right words to say to him, "...I don't know anything I can say to prove to you that things are different now if you won't believe anything I say. I guess you'll just have to let my actions do the talking for me. I love you baby sis. The real you. This you. I'm sorry, but when you were trying to be a man, it was like watching a train wreck. When a man can't make his way in the world, can't find anyone to fall in love with him, can't stick up for himself or stick by his commitments...well I'm sorry, but that's not really a man. Finding your Journal was like a lightbulb going off in my head. I realised then for the first time that all of those times I was mean to you, it wasn't fair of me. It was just mean. I was trying to compare you to something that you're obviously not. You've always been so soft, vulnerable, wimpy, clingy, and dependent on others for everything. I'm sorry to speak so harshly, sis, but it's true. Those are horrible qualities for a man, but for a baby? For a little girl? That fits the description of a baby girl down to a tee, and I dont know if you've noticed, but... I really like babies. A lot."

 Jessica suddenly picked Lilly up and began to leave the living room. "Where are you taking me?", he asked her in a worried, surprised voice.

 "You'll see in a second. Just be patient", Jessica responded.

 She brought him upstairs and headed directly into the bathroom, a part of the house that Lilly had not seen for quite some time. She gave the light switch a quick flip, illuminating the room so that Lilly could now see his reflection in the gigantic bathroom mirror. He had not seen his reflection in a long time, and what he saw gave him quite a shock. Sitting there perched in Jessica's arms like the infant that she was trying to convince him he was, Lilly's skin had grown much more smooth and feminine than he had last recalled, and his facial features were now much more gentle and rounded. His hair had also grown considerably and had taken on a much more feminine appearance, making him look much more like the little girl he was being treated as than he had last remembered. He stared at himself absolutely stunned and transfixed by the adorable, diapered little girl that was staring back at him.

 Jessica noticed the gleam in his eye upon seeing his reflection, and knew that she almost had him. She let him take in his new appearance for a few more seconds before continuing to speak. "I'm going to ask you a few questions. Not to humiliate you, but just to help us understand each other a little better, but you have to be completely truthful with me, alright?"

 Lilly began to stammer upon being forced into this compromising position. "I....I....I don't kno...."

 Jessica held him tighter and began rocking him back and forth slightly. "I'm trying to help you baby. Can you please just promise to be truthful?", she asked him hopefully

 Lilly sighed and tried to compose himself. If he had already been dragged this far, what was the harm? He decided to surrender to his sister's demands. "Alright Jess. I promise I'll tell the truth".

 Jessica gave a breath of relief and began to hold Lilly up even closer to her, speaking to him in a tender, loving way to prove that she clearly meant no harm. "Be honest with me baby", she asked, "do you like the way you look right now?"

 Lilly began to sweat uncomfortably. He wanted so badly to say no, but it simply was not true. He loved everything about the way he looked, and he absolutely knew it. He struggled to come to terms with himself as he spat out his answer. "I....I...um...Honestly? I...don't know", the tears began to return to his eyes. There was no hiding it. It was too hard for him to lie to his step-sister. "Fine! I'll admit it! I like the way that I look now! Happy?"

 "What about the way that you look? What about it do you like, Lilly? Tell me exactly

CuddleBunns

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Re: A New Family Dynamic
« Reply #88 on: July 04, 2020, 01:24:53 AM »
Part 29 (continued)

 "Everything, okay? I like the clothes, I like the way my skin and hair look, I even like the way the fluffy pink and white of the diapers stick out from under my pretty pink skirt! I hate the fact that I like it, but I do! I absolutely love it!"

 By now he was full on sobbing. Jessica felt bad for him, but she knew in the long run that it was all necessary. For now she would continue trying to get him to accept himself, no matter what it took. She began to rock him even more tenderly and continued asking him questions.

 "Do you like it when I hold you like this?"

 "Yes..."

 "Does it make you feel more safe and secure?"

 "Yes...it does."

 "What about when you sit on my lap? Mommy's lap? Does that make you feel safe and secure as well?"

 "Y...Yes. It does."

 Jessica gave a light, knowing glimpse of a giggle and kissed him on the cheek. She could tell that admitting these things was in a way therapeutic for Lilly, who was still crying but was beginning to grow slightly more calm and collected. She would continue to dig deeper and ask him more questions.

 "Do you like it when people refer to you as a girl?"

 "I...think I do."

 "You think?"

 "Okay fine, I do. I enjoy called a girl."

 "What about when people call you cute? Pretty? Beautiful?"

 "Yes. I like it when people call me all of those things."

 "Would you rather be called cute or handsome?"

 "........"

 "Answer me Lilly. There's no wrong answer to the question. Would you rather be called cute, or handsome?"

 "Cute. I'd rather be called cute."

 Jessica gave him a loving smile as she continued to hold him up to his reflection in the mirror. "All right", she thought, "now I'm getting somewhere". Her questions began to become much more rapid fire. Lilly felt his ego breaking down as he answered each and every one. His grip on Jessica became more and more tight as he answered each one, slowly realising that he was fighting a losing battle. It was beginning to appear that she was right about everything.

 "Do you think most men would rather be called cute or handsome?"

 "Handsome..."

 "What do you think most girls would rather be called?"

 "Probably cute"

 "Do you think you look cute, Lilly?"

 "I...maybe..."

 "Oh don't be modest! I think you look adorable! Admit it!"

 "Fine! I look cute. I look incredibly cute"

 "Do you think your diapers make you look even cuter?"

 Lilly blushed. He could tell exactly where she was going with this, but he still felt powerless to stop himself from telling the truth.

 "Yes, I think my diapers make me look cuter"

 "And who wears diapers Lilly?"

 "Jess please..."

 "Come on Lilly, it's not that hard. Do I really need to answer for you?"

 "Fine, babies. Babies wear diapers."

 "And you wear diapers too, Lilly?"

 "I do."

 "If babies wear diapers, and you also wear diapers, then what does that make you?"

 Lilly paused for a second, struggling to give Jessica the answer that he knew she was looking for. Jessica simply continued holding him and rocking him back and forth, confident that eventually he would give her an answer. Eventually he conceded and finally broke the silence.

 ".....A baby."

 "What was that little sis? Could you repeat that?"

 "A baby. It makes me a baby."

 "Alright sis, as long as you admit it! Do you enjoy it when people call you a baby?"

 "I think it's humiliating."

 "Of course it's humiliating. My question was whether you enjoy it"

 "...Fine. Yes, I enjoy it."

 "What about when people treat you like a baby? Do you enjoy that?"

 "Not in public."

 "What about at home?"

 "Truthfully? It's....alright. Other than the boring parts."

 Jessica's ears perked up at his unexpected answer. "Boring parts? What do you mean by that?"

 "Well you know...being forced to sit by myself in a playpen all day, spending half of my time in a crib, stuff like that. It's depressing."

 Jessica suddenly found herself deep in thought. She believed she might have a solution to that problem, but decided that now was not the right time to try telling him. She decided to ignore this tangent for now and get back to the questions she had planned.

 "Awww baby, that's too bad. I wish I could help you there. Do you think our mommy likes you better as a baby?"

 "Yes"

 "Do you think I like you better as a baby?"

"....Um, yeah."

 "Heh, we'll you're right about that one. Do you like being around me more when I treat you like a baby?"

 "Yes Jess. I do"

 "See? I knew it! And you like it when I call you cute? When I compliment your pretty diapers and dresses?"

 "Yes"

 "And who else likes receiving compliments on their pretty diapers and dresses?"

 "...Little girls?"

 "No Lilly, baby girls. And do you know what that makes you?"

 Lilly looked into his reflection with tear filled eyes. He did not know when, but at some point his tears had stopped being tears of humiliation and started to become tears of reluctant acceptance. He turned to Jessica's loving face in the mirror and saw that she had no expression of irony or of sadistic glee in her eyes. Instead she had an expression of genuine love and sympathy for her baby sister, who she held lovingly in her arms with a strong, protective grip.

 "Come on baby, say it! We both know you want to. There's absolutely no reason to be scared. Your big sis loves you so, so much. I just want you to be happy, and finally love yourself for once. Can you please just admit to me what you are?"

 "........"

 "Please? For me?"

 Lilly took a deep breath and prepared for his big moment of truth. He could fight it no longer. Jessica was right about everything. From the beginning, she could read him like an open book, and there was absolutely no use in fighting back. He closed his eyes and held her tight, readying himself for the inevitable.

 "I'm a baby girl...", Lilly mumbled.

 "What's that little sis? Say it louder. Say it like you mean it."

 "I'M A BABY GIRL!" Lilly was now yelling at the top of his lungs. "I'M A PRETTY LITTLE BABY GIRL, AND I LOVE TO WEAR DIAPERS AND DRESSES AND I LOVE BEING HELD BY MY AMAZING BIG SISTER AND MOMMY!"

CuddleBunns

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Re: A New Family Dynamic
« Reply #89 on: July 04, 2020, 01:27:54 AM »
Part 29 (continued further)

 By now, Lilly's psychological transformation was fully complete. She now understood what she was with every fiber of her being, and and could no longer insist that she was not a baby, nor a little girl. Jessica gave her back a few loving pats and buried her further unto her shoulder in a loving display of affection. "Thank you Lilly", she whispered into her little sister's ear, "You don't know how proud I really am of you. I know it took a lot of courage to say that out loud, and I want you to know that no matter what happens, no matter how you feel, me and mommy will always be there for you, and we will always love you for who you are".

 Lilly felt a weight lifted off her shoulders as she lovingly returned her older sister's hug. "Am I still allowed to talk big sis?", Lilly asked Jessica with a decidedly juvenile twinge to her voice. Jessica shook her head and sighed. "I don't know Lilly, what do you think? Do babies talk?"

 The subtext of Jessic's response was abundantly clear to Lilly, who stuck her thumb in her mouth as a nonverbal que that she had received the message loud and clear. Just then however, almost as a sign from the gods, the remnants of Lilly's lunch began to catch up to her and a loud fart automatically erupted from the seat of her already wet diaper. Jessica gave her sister a knowing look, almost as if this was one final test to confirm Lilly's status. Lilly knew that there was no use fighting it or feeling humiliated by what she was about to do. She had just admitted that she was a baby girl, and knowing the look that Jessica was giving her, was fully expected in this moment to prove it. Jessica soon let go of Lilly, who took the opportunity to squat down in front of her sister and begin pushing. Her face became more and more red as a gigantic wave of squishy poop began squeezing it's way into her diaper, filling the air with a pungent smell that would be extremely obvious to anybody. She looked up at Jessica as she squatted and continued to do her business, who was looking down at Lilly with a look of tender love and understanding, instead of the joyful look of amusement that Lilly had come to expect. When Lilly was finished, she waddled forward slightly with her thumb still in her mouth and hugged her sister's leg. Jessica reached down and picked her baby sister up, cuddling her into her shoulder once more. "That's right baby", she cooed as she gently rocked Lilly's body in the air, patting her hand against Lilly's squishy bum, "That's exactly right".

sarahpenguin

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Re: A New Family Dynamic
« Reply #90 on: July 04, 2020, 05:59:54 AM »
oooh a series of excellent chapters :)

 

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