A New Family Dynamic

[CuddleBunns]

Thank you for the kind words, Sissyboy1212 and Sissy Little Girl. I have a few humiliating ideas in mind for Lilly in the next couple of parts, although I would be lying if I said I had it all planned out in my head already. Needless to say, his sister Jessica is going to love getting the little sister she never had growing up. Maybe even a little too much, to Lilly's dismay.

[dolly bo peep]

CuddleBunns,

I enjoyed reading the newest addition to your story.

Mommy Andrea seems to be following her interpretation of what Lilly, then Nate, wrote in his journal.

Now that wet and messy, stinky diapers, chastity, and having his activities severely controlled and limited with spanking for punishment, Lilly is finding out that when fantasies turn into real life, it's not as peachy keen as it seems when it existed only between the ears.

All of us readers are interested in how Lilly's re-introduction to big sister Jessica will go.

I think that Jessica will love her baby sister to the point of great annoyance to Lilly.

What other fantasies will slowly come to life for Lilly? Will they also not quite turn out what was imagined before it all started coming true?

[CuddleBunns]

You are quite right about his sister, dolly bo peep. I think she's going to become a much more frequent presence in Lilly's life now that she has a little sister to coddle and dote over. If Lilly doesn't learn to accept his new role things could get pretty hard for him.

[CuddleBunns]

Part 12

 Lilly remained seated in the cramped play pen as the evening drew nearer and nearer. Unlike the rest of his baby furniture, it was not sized for an adult, meaning he had to curl his legs slightly to sit inside of it. By now his diaper was soaking wet for the fourth time that day, and although he had told his mommy about it, she dismissed him on the grounds that it could take much more wetting. All in all, he was not having a great experience with his new life so far, and wondered how long he would really be able to take it before he snapped.

 The monotony was soon broken, however, by the ringing of Andrea's cell phone and the news that his step-sister Jessica was on her way and would be arriving in a half hour. Andrea hung up the phone and immediately started preparations. Lilly now found himself being removed from his play pen and carried up the stairs by a now clearly elated Andrea.

 "I'm so exited sissy. Jessica works with little babies like you, so I know she's going to love how you've changed in the last two days. I mean, why wouldn't she? It was her idea.", Andrea beamed to Lilly as she carried him up the stairs. It was true, Jessica had a full time job as a senior staff member at a local daycare center, and she had always loved babies in particular. Maybe it was because she had not had luck having one herself, but Jessica seemed to instantly dote over any baby that she saw, to an extent that even Andrea had to roll her eyes sometimes. It was the other thing she said that most disturbed Lilly though. Her idea? What role did Jessica have in all this. Lilly had to ask.

 "What do you mean her idea mommy?", Lilly asked as Andrea began to carry him into the nursery. She plopped him down on the changing table, removed his overalls, and started to change his diaper as she continued the conversation. "Well you see baby girl", she said, "I wasn't being completely honest earlier when I said that I found your journal. It was actually your sister who first discovered it, when I let her clear out your room after you moved out. At first she just told me about it and we had a good laugh, but when she noticed how lonely I was, she was actually the first to come up with the idea of regressing you back into a little baby girl. It took some convincing, but I'm glad I listened to her. This new look fits you SO much better".

 Lilly laid there dumbfounded for a second while he processed what his mommy just said. He knew by now that Jessica was in on this somehow, that much was obvious, but the thought of her directly reading his deepest, darkest fantasies right from the source made him want to sink into the floor. As far as he was concerned his old life was already over, and feeling intense shame and humiliation was all that would lay in his future.

 Andrea, for her part, could sense his discomfort and decided to leave the topic of their conversation behind for the time being. She resumed his diaper change, this time changing him into one of his thick night time diapers, and topped it off with a new addition that Lilly had not seen before; A pair of pink ruffled panties. Lilly could only imagine how sickeningly sissyish he must have looked as his mommy lifted him off of the table to inspect his newly ruffled behind. Satisfied with the way that it fit, she next exchanged his pink t-shirt for a soft yellow dress with puffy shoulders and a layer of petticoats to top it all off. For her final touch, she began to do his hair and placed a pink bow on top of it, a proverbial cherry on top.

 Andrea looked her sissy son up and down, admiring her handiwork. She checked her phone and realised they did not have much time until Jessica would arrive, so she put her plan into action fast. She began to dig through the closet until she found a mysterious looking piece of cardboard with some words written on it, although Lilly could not yet tell what it said. She next carried Lilly and the piece of cardboard down the stairs and out the front door, right into their front yard in the middle of broad daylight. This absolutely terrified Lilly, who had yet to leave the house in his babified and sissified state.

 Andrea plopped Lilly down onto the grass and began to explain what was going to happen next. "Okay baby, your sister is going to be here any minute now, and I want you to be the one to greet her!", she explained to a visibly upset Lilly, who had hoped his mommy would be the one to do most of the talking. Andrea continued to explain his next humiliating task, "See this sign here Lilly? I know you're still too young to read, but it says 'BABY SISTER WUVS HER BIG SISTER'. Don't you think she'll love It? Look, I even drew some little hearts!"

 Andrea gave the cardboard sign to Lilly and pointed to a few large illustrated hearts. This did not change Lilly's expression in any way, which was one of nervous bewilderment. She simply ignored his lack of a response and continued. "I want you to stand here and hold this sign until your sister gets here. To really drive the message home that you're her LITTLE sister now, I think you should also suc-k your thumb when you greet her, I just know she'll find that so adorable. Can you do that honey? Can you suc-k your thumb?"

 Lilly did his best to comply and stuck his thumb in his mouth, although it took a bit of further prompting to get him to actually suc-k on it. "Good girl. You look so adorable honey. I don't think I'll ever be able to get her off of you", his step mommy replied with praise. The praise would soon be interrupted by the approaching sound of an automobile that was pulling into the driveway.

 Andrea gave Lilly a pat on the back, signalling that it was time to hold up the sign for his sister Jessica. Lilly tried his hardest to overcome his fear and pointed the sign in the direction of Jessica's now parked car. The drivers side door of the car soon opened and out walked Jessica, who instantly put her hands over her mouth and squeed at the sight of her feminized and babified sissy sister. She closed the car door and nearly sprinted towards the two of them on the grass, making incomprehensible high pitched noises the entire time. By the time she reached the two of them she could barely contain herself and gave her mom a quick hug before turning in the blink of an eye towards Lilly, who she instantly began to dote over with the excitement of a kid on Christmas.

 "OH MY GOD. OH MY GOD! What did you you do to him? He's so cute!", Jessica said in a manic frenzy as she inspected and analysied every square inch of his sissy outfit. Lilly could only stand there speechless as she had her way with him, poking and prodding at seemingly every point on his body before taking notice of the diapers. "You did it! You actually did it! Oh my god I think Im going to faint! You actually put him in diapers!", she said with a laugh as she started to pat his diapered behind.

 "Oh you'll find she's quite the good little girl now", Andrea replied, "Look, she's even got a sign for you." Jessica stood back for a second while Lilly held the sign back in front of him. Jessica gave it a quick once over and an enormous smile appeared on her face. She practically leaped forward and embraced him in a warm hug. "Awww, I wuv you too little sis. We're going to have so much fun together, now that you're just a wittle sissums. And a very pretty wittle sissums at that. I could just about eat you alive! ", Jessica beamed down at a frozen and confused Lilly, who was not used to his sister being this excited to see him.

 "What do you say to your sister Lilly?", Andrea asked him pointedly. Lilly shuffled his feet a bit before working up the courage to respond. "Th...thank..." Suddenly he was cut off. "Thumb in your mouth, baby girl", Andrea reminded him. He stuck his thumb back into his mouth. "Fank youu sisuah Jessica, youwe pwetty too", Lilly replied almost incomprehensible around his thumb. This caused Jessica to clap her hands and envelop him into another hug. "Can I please carry her inside mom? She's so cute that I simply can't let her go!", Jessica asked her mother excitedly. "Of course you can dear", Andrea responded, "but that's exactly what I was afraid of".

 Jessica laughed at her mother's little remark before sliding her arms around and under Lilly, picking him up as the three of them headed inside.

[sarahpenguin]

Hmm they should find him a bigger playpen so he can at least crawl around in a circle and high enough he can't get out for when baby doesn't have someone to watch him in the room :)

[CuddleBunns]

That's a great idea, and he probably will get one of those eventually. I only used the portable one in this instance because there's something very humiliating to me about actually having to sit in a play pen made for an actual baby. At 4 foot 9 inches, he can't fit in many things made for actual babies, so he's going to have quite the arsenal of sized up furniture by the time he's fully settled into his new life. 

[CuddleBunns]

Part 13

 Lilly remained in Jessica's arms as the three of them entered the house. The first thing Jessica noticed upon entry was his tiny play pen sitting in the middle of the living room floor. "What's the matter, did the furniture website I gave you not work", she asked her mother with a concerned tone. Andrea just laughed. "Oh heavens no dear", she replied, "I just thought it'd be easier to have something small and portable to keep her in when I want to watch her more closely. I've been thinking of getting her a larger play pen though, since she could easily escape that one. If you want to see some of the furniture I ordered, wait until I show you the nursery". Andrea motioned them up the stairs and Jessica nearly bounced up and down with glee.

 When they arrived in the nursery, Jessica was amazed. She had seen the pictures on the internet, but seeing it all in real life was a completely different feeling. She imagined the little sissy in her arms being locked in her crib or being changed on the changing table, which made her feel happy and excited. In truth she had not cared all that much for Nate before, but now that he was Lilly, she imagined him almost as her own real life doll to do as she pleased with. She soon noticed a number of diapers on the shelf next to the changing table and thought to herself for a second.

 "Wait, so are you making her use her diapers as well?", she asked her mother with a curious tone. Andrea gave a small chuckle to herself and stepped on the pedal of Lilly's diaper bin, opening the latch and exposing her previous two days worth of messes to a now hysterical Jessica.

 "OH MY GOD!", Jessica yelled out between fits of laughter, "That's so gross! I guess you weren't kidding when you said you were going to go through with it!". Lilly began to tear up at the humiliating situation unfolding in front of him. Jessica didn't take much notice to this however, and looked one last time at the diaper pail before her mother closed it. "SHE POOPS IN HER DIAPER TOO! OH NO THIS IS JUST TO MUCH", Jessica practically screamed out, unable to contain herself in between fits of hysterics. By now tears were starting to flow down Lilly's face. Clearly there was no going back from this. Even if he were to resume his life as an adult man tomorrow, his sister would remember this moment forever.

 His mommy shook her head and rolled her eyes. "Honestly Jess, you work in a daycare. The fact that she messes herself makes her a perfectly normal baby in my opinion. You probably change a hundred messy diapers a day", Andrea said to Jessica, who was beginning to regain a little composure. "I guess you're right", said Jessica. She turned her face to look directly at Lilly's. "You can't help it can you little sis? Babies like you can't control when they make wetsies and messies. Speaking on which..." Jessica cut herself off mid sentence and stuck a finger underneath Lilly's pink panties and checked his diaper for wetness. "Aw man, completely dry. I was looking forward to changing you", she said with disappointment.

 "Oh believe me", said Andrea, "there'll be plenty of time for that later. Would you like me to heat up a bottle so you can feed her?" Jessica's eyes lit up at the mention of this idea and she agreed that she would love to feed him his bottle. They made their way downstairs where Andrea told Jessica to place Lilly in the play pen temporarily while she showed her how to prepare his bottle. Lilly sat defeated in their absence, realising that Jessica was enjoying this way more that he thought that she would.

 Meanwhile in the kitchen, Andrea was giving Jessica the rundown on preparing Lilly's bottle. "You see, I start with a base of regular infant formula", said Andrea, "but the real secret sauce are these little things I have right here". Andrea pulled out a pill divider with various medications all sorted by type. She began to explain their function to Jessica. First she picked up a blue pill. "This first one here is sort of like an estrogen pill and a testosterone blocker all in one, but it's been specially designed to only feminize her so much. Basically I want to smooth out her features without having her you know, develop." As she said this she shook her breasts causing Jessica to giggle at the thought of her brother with a full rack of boobs. "Now I know it would be pretty funny to see that", Andrea continued, "but the goal here is to basically undo her puberty and make her a bit less masculine, not to turn her into a full grown woman".

 "Now that's the only pill that I add to every single bottle, but I have a few more at my disposal when I need them. For example, this one." Andrea held up a red pill to show Jessica. "This one is a muscle relaxant for if she ever tries to walk around like a big girl. I figured it would be fun for the game we were going to play tonight. You brought all the things we need right"

 "Yeah mom, it's all in the car. I can't wait to see the look on his face when he realises what we are going to make him do", replied Jessica.

 "Excellent", said Andrea, "It'll be cute to watch him stumble around everywhere. Anyways I have one last pill here. This one is a pretty basic laxative. I don't think I have to explain to you what it does, just be prepared to cover your nose". Jessica tried to contain her laughter as her mom crushed up not one, but two of the laxitives and added them, along with the blue and red pills, to the bottle of formula. She gave it a good shake before heating it up in the microwave, and the two of them headed back into the living room.

 "Hey there little sis, time for your baba" Jessica cooed as she approached Lilly's play pen and picked him up, sitting down on the couch and placing Lilly down in her lap. Andrea handed Jessica the bottle and she wasted no time guiding it right to Lilly's lips. He began to suc-k down it's contents while he looked directly up into Jessica's eyes. It was very embarrassing being bottle fed by his sister, although Lilly had to admit that it was at least a bit better than the cold shoulder treatment these two women usually gave him. Jessica, for her part, gave him many loving words of affirmation as she encouraged him to suc-k all of the contents out of the bottle. By the time it was all gone, Lilly had not even noticed that his mommy had pulled out her phone and was recording the whole thing.

 "Okay, up we go baby. Time for burpies", Jessica said lovingly as she picked him up and placed him over her sholder, producing instant burps when she began to massage his back. Jessica had a lot of experience burping babies, and in this moment strangely found herself seeing him no different than any other baby, completely innocent and dependent in every way. It almost made her feel bad for what she was going to do to him later.

 Once the feeding was done, Jessica continued to snuggle up with Lilly on the couch. She wanted to see Lilly with her pacifier, so Andrea went back up the nursery to retrieve it, plopping it into Lilly's mouth as he lay there on his sister's lap enveloped in her loving arms. Lilly almost drifted to sleep as he lay there listening to his mother and Jessica talk, but he was rudely jolted out of his drifting state by a familiar feeling in his stomach. It was happening again.

 "Mmm...Mommy, Mommy! I gotta go poopy", Lilly blurted out, immediately embarrassed at what he just said, but also too distracted by the urgency of his situation to really care. Jessica just giggled and held him tighter. "Awwww, she even calls you mommy!", she said to Andrea as the sissy began to writhe in pain on her lap. "Its okay baby girl", said Andrea, "Your sister has seen lots of babies make poppies."

 "Yeah", added Jessica, "I see babies make stinkies for me all the time. From where I'm sitting I don't see why you'd be any different." The struggle continued for a few minutes as Lilly tried to hold out, but once again the laxatives had won. Tears began to fall like raindrops from Lilly's face as a gigantic mass of mushy poop began to release into the back of Lilly's diapers. Andrea and Jessica knew from the smell alone that he had finally let go almost immediately.

 Jessica placed her hand on the back of Lilly's diaper and felt it expand as she whispered encouraging words to her clearly distressed baby sister. "Come on baby, that's it. Just let it out. It'll all be okay princess, big sister is here for you. You don't have to cry. It'll all be okay", she spoke softly as he continued to cry and release messy poo into his diaper. Worse still, by now his bottles had caught up to him, and he began to wet himself as his sister continued encouraging him to use his diaper, making him feel more babyish than he ever had in his entire life. Jessica genuinely did feel bad for her new baby sister, who was clearly distressed at the whole situation, but she knew that in order for her and Andrea's plans for full babification to work, Lilly needed to be broken down psychologically in a way where he could never see himself as a man again. The only real consultation she could give right now was her loving affection, which she had in spades.

 After he was all finished messing, Lilly lay in Jessica's arms quietly sobbing into her sholder, with Andrea hitting stop on her phones video recorder and looking on with mixed feelings. On one hand she hated seeing him suffer like this, but on the other hand, she knew that she had just broken a psychological barrier. If she planned on having him completely regressed by the end of the week, she needed to go through with her plans. "Alright", said Andrea, "Let's get the baby changed and then we can all have some dinner".