Lisa's Descend into Adult Babyhood Pt.1

Intro

Lisa was the kind of girl most people were jealous of, she was the kind of girl who got everything she wanted. Her parents were loaded, easily able to afford sending Roxanne to the best college there was without a single worry about student loans. They even bought her a luxurious four-bedroom apartment in an upscale part of town. Her father, a well renowned investor saw a good opportunity in this. The apartment was ideally located and would only gain value. Real estate always was a good investment to begin with, the fact that it meant his precious daughter and only child got to go to college and live in the utmost comfort was another bonus.

On top of that Lisa also was a gorgeous girl. She wasn’t tall, standing at about 5’2” but she was fit due to the years of cheerleading. She had nicely toned legs, a cute bubble butt, a flat stomach and while her breasts were only an A-cup they looked good on her as well. Her face was a thing of beauty as well. She had natural flawless honey blonde hair reaching all the way down to her mid back. She was very proud of that, her hair and used only the best products to take care of it. Her nose was pretty cute with its slightly upturned button look separating a pair of big steel blue eyes that seemed to pop out on her sun kissed skin.

Years of being spoiled had turned Lisa into somewhat of a brat though, she treated waiting staff and the maid that cleaned her apartment in a quite arrogant way. According to her thinking they got payed to serve her, so she didn’t need to put any effort forward to be nice right? She didn’t help putting everything on her plate to make clearing a table easier and she certainly didn’t even consider making her apartment even somewhat presentable when the maid came over which was on Tuesdays and Thursdays. In fact most days when she was around when the maid was cleaning she only nagged her complaining about vacuuming too loud or ordering to fetch her drinks.

At school she was one of the popular girls though a lot of girls kind of disliked how Lisa always had to be the centre of attention but she did throw the best parties and took them places they usually wouldn’t come like some fancy lounge bars so they put up with it. When it came down to relationships Lisa burned through one boy after the other. Her standards look wise were really high but even then, she was very demanding until now no boy had ever been able to put up with her long enough to get serious leaving her an 18-year-old virgin.

Status and how others saw her meant the world to Lisa she always was dressed in clothes of some kind of designer brand, instantly buying the new collections. Afterall as an added gift she had gotten a credit card from her dad that gave her practically unlimited spending budget. No matter how much she spends she never even got a text to say she should tone things down. It simply didn’t matter even with her elaborate lifestyle her dad made money of his investments way faster than she could give it away.

Chapter 1

Today was a Monday and while that usually didn’t really count as a party day it had certainly turned out to be one. Today was the day the cheer captain was announced, and she had won with a unanimous vote. Not that it was that much of a surprise given how she had basically rigged the vote by giving everyone allowed a vote some fancy gift. Still a new status to be proud of meant a party and the whole team was invited over at her apartment to celebrate. Some of the girls had some mixed feelings about Lisa becoming cheer captain since it was her first year at college and on the team. Especially since she hadn’t even showed her worth yet and had gotten the spot over some girls who had worked really hard for it.

At least the party made up for some of it even it was only a small consolation compared to their work paying off. The only thing they could really do about it though was enjoying themselves on Lisa’s costs. Lisa in turn hadn’t saved any expenses at all. Upbeat music blasted to the expensive sound system that her livingroom was equipped with. Usually it served as the sound system for her home cinema together with the huge flat screen on the wall. Her livingroom was huge and was connected to a balcony with a perfect view over the city skyline. She had opened up her bathroom for the girls to use as well as the jacuzzi on her balcony. In the spacy open kitchen there was also a bar where she had hired one of the city’s best bartenders to make cocktails for the guests. Instead of the pizza you got at normal college parties Lisa had hired a Sushi chef that made rolls on demand during the first half of the party.

Everyone, even the girls who kind of disliked the fact that Lisa had become captain had to admit this was a party unlike any other they had ever been to. Besides if Lisa hadn’t gotten the spot she would have probably made a huge fuss. The girl really could act like a big baby sometimes when she didn’t get what she wanted. A group of girls laughed to themselves as they looked at Lisa who was dancing on top of the dinner table, a bottle of champagne in one hand and a cocktail in the other. The girls just rolled their eyes. Typically Lisa needing to get all the attention.

The party went on till early morning, most of the girls had left already, the sushi man was gone as well as the bartender. There was still enough booze left but with only a few girls remaining the party was over. Lisa had been laying blackout drunk on the couch for nearly an hour but the three girls who had originally contended for the spot of head cheerleader before Lisa had bribed the vote were still there. They had vowed among themselves that they would take advantage of the things Lisa had provided as much as they could. Each of them was pretty wasted as well as they giggled among themselves how much champagne they had drunk and what a fortune it must have costs.

“I have drunk at least two bottles of champagne.” Amanda, a 5’9” raven-haired girl boasted.

“Oh my god, that is like a couple of hundred dollars at least. That stuff has to be imported from France and it didn’t look to have come from one of the cheaper sellers either.” Roxy, a 5’6” gorgeous redhead joined in.

“Well I think it serves her right” Amy, a 5’7” brown-haired girl said nodding her head at Lisa who was laying passed out on the couch. “If she would have had to compete fair and square or if the votes would have been given according to effort she wouldn’t have stood a chance against us.” She continued, the three former rivals all agreed upon that one. At least if either one of them had won it would have been fair. Sure the others would be disappointed for a bit but Lisa really didn’t deserve this. None of them would ever publicly admit it, and they would still act as her friends out of fear of being excluded but in secret the three girls loathed Lisa.

“Pfff even if she had lost she would probably just have made a fuss every practice ruining the team like that. She really is a big baby when it comes to losing” Roxy sighed.

“Speaking of a big baby, are you guys thinking what I’m thinking?” Amanda asked with a devious smirk looking at past out Lisa.

Her two friends instantly agreed giggling, “This is perfect” Roxy laughed as they approached Lisa and started stripping her down. The drunk girl didn’t even really react to the sudden movement of her limbs as she stayed past out.

“Well it isn’t all that much, but it certainly does count for something. Besides it’s going to suit her, just look at those tiny breasts” Amy laughed. 

Once Lisa was completely naked the girls scared out over the apartment before all joining together again with the items they had collected. Amanda was carrying a big sheet of white bed linen and some safety pins. Amy had found some pastel pink ribbon, a hair brush and pair of plain white knee-high socks. Roxy on the other hand had found a rather large teddy bear Lisa once had received as a gift from a boyfriend that didn’t last.

Giggling loudly the girls went to work on passed out Lisa, Amanda shoved the big sheet underneath Lisa’s bottom, bunching it up so it looked big and full before securing it with the safety pins. Stepping back she laughed at the result. The white cotton together with the way she had it bunched up really resembled a diaper. At least if you didn’t look to closely.

In the meantime Amy rolled the knee-high socks up Lisa’s legs while Roxy brushed the girls hair out into two fluffy pigtails which she tied off using the pink ribbon. To make the picture complete Amanda took Lisa’s left arm which was hanging off the couch and wrapped it around the teddy bear shoving the thumb of her left hand in her mouth.

The three girls stepped back and had a good laugh at Lisa’s expense the look they tried to accomplish worked out so well, the girls small frame and tiny breasts fitted the outfit perfectly, especially since her bubble butt was hidden away by the makeshift diaper. Sleeping peacefully the girl really looked like the big baby the girls thought she was and laughing their asses off they also left closing the door behind them in the knowledge Lisa would probably have a good scare when she woke up and saw what she was wearing.

None of the girls could have guessed the proportions of the scare or how life changing they would end up being for Lisa when a few hours later the maid arrived to start her work day. Even in the hall the evidence of the wild party was noticeable. Suzan sighed deeply as she realised today was going to be a hard one. Cleaning up after the brat, like she liked to think of Lisa, had a party was always especially hard. Not only was the apartment way dirtier, it also meant that Lisa would be home skipping her morning classes to sober up if she woke up before noon at all. Having to put up with a cranky hungover Lisa was no pleasure at all. Working with a normal Lisa around was already difficult. She knew she had no choice however. Being a maid for this brat and a few others in this building payed the bills. Suzan really couldn’t afford losing her job and so she would just have to put up with Lisa.

Suzan was 48 years old, and it showed. She had a few wrinkles here and there, her figure wasn’t what it had been anymore, over the years she had put on quite a lot of pounds. At first she managed to pull it off with how tall she was standing at 5’11” but even that past and now she could only be described as chubby. Her brown hair which reached to just below her shoulder blades had a couple of grey streaks in it and she was starting to have to deal with some sag here and there. After all this time finding a man seemed pretty much impossible and having a child was impossible she had always wanted a baby but as she past 40 she knew she would have to find peace with the fact that that wouldn’t happen. Suzan had never had the luxury of going to college or chasing her dreams and as a result she was stuck with this cleaning job to support her.

Needless to say Suzan was shocked when she stepped into the livingroom only to find Lisa laying there in what looked like a diaper, hugging a teddy bear and sucking her thumb. She really didn’t know what to make of it as she froze just looking at the sight in front of her. This was simply indecent. The young girls breasts were even on display. At first the sight disturbed her greatly but the more she looked the fonder she grew of that sight. She had to admit that the look really suited the girl, it looked so peaceful and cute even. It almost made it hard to believe that this was the same girl that made her have such a hard time doing her job, treating her like just a lesser person simply because she paid her. The thought of all those nasty things made her angry and as those two feelings mixed an idea struck her.

Looking at the entire picture this had obviously been a prank pulled on Lisa, the countless empty bottles and the makeshift outfit sure all pointed in that direction. A more radical version of drawing something on someone’s face. By the looks of it Lisa would probably not have a clue what had happened or why she was in this situation. Which meant that if Suzan played her cards right this might actually turn into something great. With a swift movement she fished out her phone and zoomed in on the girl laying on the couch snapping several pics of her and a couple of videos, careful not to show any signs of the party or any other context. These pics would make it look like this was just a perverted thing Lisa enjoyed. That she had dressed up like this for bed like some weird fetish. In other words perfect blackmailing material.

The adorable sight melted Suzan’s heart yet the arrogant battiness made her anger. Since this was probably something Lisa wouldn’t like it would serve as perfect revenge while giving her a baby to take care of like she had always dreamed about. Hell she might even be able to re-educate the brat and teach her some manners and respect. A perfect opportunity to kill three birds with one stone Suzan thought to herself with a smile.

Now she just needed to set this up right deciding the best chance lay in re-enacting her first shocked reaction but then louder, waking the girl was the best opportunity, a bit of embarrassment certainly wouldn’t hurt. “Oh my god, Lisa?! Is that you? I can’t believe it” Suzan screamed out in feigned shock.

The girl reacted by slowly stirring awake her eyes small obviously still tired and hungover. “huh, wat e uck” Lisa babbled her thumb still stuck in her mouth. It took her intoxicated brain a minute to figure out that she needed to take it out to talk, and another minute to realise something was wrong. She never sucked her thumb but looking down she noticed it was completely wrinkled, her thumb must have been in her mouth for a long time. Looking down she also realised she was hugging a bear and wearing a… was that a DIAPER?! What the hell was going on here? Whit a shocked shriek she jumped up only now realising the full gravity of the of the situation. She was standing naked apart from the diaper and socks in her livingroom in front of the maid and she had no idea why. All her groggy brain could think about was running and so she did, clutching the teddy bear tightly in the hope of hiding her bare breasts, her cheeks bright red and all of it accompanied by her maid’s laughter. She was mortified as she disappeared in the bathroom spotting in the mirror that her hair was in pigtails as well.

Suzan just carried on laughing for a few minutes straight not bothering to call the girl back or even attempting to go after her. Instead she just started her work once she was done laughing. There was no need to push the matter right now. She had received the exact reaction she had hoped for and that was more than enough. Especially when she saw Lisa running past her half an hour early obviously escaping with the least possible interaction instead of a rude comment like usual.

Once outside Lisa felt relieve that had been one hell of an embarrassing way to wake up and she absolutely just wanted to forget about it. She felt kind of pissed that her maid had laughed at her like that but the last thing she wanted was to be confronted about her situation of this morning again. It took Lisa a while but eventually she managed to forget about the incident as she carried on with her day. Especially cheer practice was wonderful in that aspect. She loved assigning roles and telling people what to do and how to do it. It was all relevant information to the practice to improve the choreography and yet it made her feel powerful. Amy, Amanda and Roxy just exchanged looks thinking back to their prank of yesterday. It at least helped to make practice with this brat as head cheerleader more bearable.

Suzan’s day went by in a breeze as she walked around whistling all day long thinking about the things she could do to Lisa. She would never admit it but she actually also got a sexual thrill out of seeing the pretty girl nearly naked. Cleaning was almost no effort at all at the moment and that while she had been anxious walking in this morning fearing the terrorising brat. Eventually everything was clean and Lisa hadn’t come home yet so to kick the next stage of her plan into action she left a note for Lisa to be found.

“Dear Lisa,

I couldn’t help but feel shocked when I caught you all dressed up like a baby this morning. It is highly unusual behaviour and it made me feel rather uncomfortable. I have taken some pictures as proof to maybe file a harassment claim with the cleaning firm that employs me. Their standard practice is to send my full statement including the pics to the person who pays the bill. 

I am also contemplating whether or not I should contact your school’s student coach Afterall such deviant behaviour might be dangerous to other students. Do they know about this?

Before doing anything however I would like to discuss this with you in person. Maybe if you can explain yourself none of this would be necessary. I would like to do this on Friday 19 o’clock at my place. Be there or I am afraid I will have to take one of the earlier steps.

Yours truly,

Suzan

PS. I really hope we can resolve this between the two off us.

PPS. I am taking Thursday off to think this over. I do expect this to be a payed leave however, I’m sure you’ll understand”

With a smirk Suzan went home imagining the reaction Lisa would have upon seeing this. Sadly she wouldn’t be there to see. She was however curious to see if the girl would show up on Friday or not. Suzan certainly had given her the right motivation she thought although for what she had planned that motivation might not be enough.

When Lisa came home she was completely obvious to the note Suzan had left for her. It wasn’t until she was ready to head to bed that she spotted it and instantly her blood ran cold. That fucking bitch had taken pics of her?! Worse even she expected her to come over to her place on Friday, the nerve. Yet Lisa also knew that if she didn’t go there on Friday she was fucked. The firm would send the pics to her dad who would be pissed, let alone the fact that she would never dare to look him in the eye again and if the school counsellor found out there would probably be sanctions hell, someone might even pic a rumour which would destroy her reputation. No, she couldn’t risk that. She had to show up on Friday willing or not, since it was only just a maid she would probably be easily bribed, a thought that gave Lisa comfort as the rest of the week carried on as usual. Still as Friday evening started to approach she felt the nerves building up.