Oldest to Youngest - Part 1 (Patreon)

Sometimes it was really difficult to be the oldest sibling. You were the first one to do all of the big important things in your family. First one to go to school, first one to drive, and first one to do most everything before your siblings did. Sometimes the pressure could become a little bit too much.

Sadie felt like that was the case more often than she liked to admit. She was the oldest of five children and the pressure of being the oldest often weighed down on her. Despite her own personal worries and responsibilities, her parents often put way too much extra duties on her shoulders when it came to helping take care of her brothers and sisters. Sadie could even remember some of the first several years of her life when she’d been an only child, but with every kid that had been born after that the attention that she would get from her parents seemed to decrease more and more. Specifically from her Mother whom she’d always been extremely close to.

By the time Sadie was 18 years old she had grown a resentment to her younger siblings that not even she fully understood. It took a bit of analyzing on her own to realize that she felt kinda jealous of them. She wasn’t sure exactly what that meant other than she missed the attention she used to get and she wasn’t sure exactly how to get it back.

After a while she began to observe her siblings in a new way. She still felt jealous of them, but her jealousy changed to more of a longing to be the way they were, to act the way that they were. All of her siblings always looked so happy and so free. She wanted to feel that way again... but how?

An answer, however convoluted she thought it might be, came to her on a day that she found out that the rest of her family was going out for most of the day and she’d be by herself for several hours.

She decided to go check out the children’s play room.

In a hopeful and cheerful mood, Sadie waved goodbye to her family and locked the door behind them. As she made her way to the playroom she felt strangely excited. She’d been in the play room hundreds of times, but with her intentions currently so pure and innocent she felt like she had an exciting new secret she was about to indulge in.

In the playroom, Sadie felt kinda silly for a while. For the first few minutes she just kinda stood there looking at the toys and stuffed animals in the room. The room was decorated for fun with little stars on the walls and foam play mats lining the floor. She was annoyed at herself for feeling kinda bored as she stood there, but when she thought about it she realized it was because she was still holding back. She needed to find something to help herself get into the mood.

She walked to the bathroom and looked in the mirror at herself. She wiped away all of her makeup, took her jacket off, and put her hair up into pigtails. She was surprised by how... adorable she looked.

She got another thought... then chastised herself for how silly it was. After reminding herself though that she was alone, she decided to try. She reached up and stuck her thumb into her mouth and began to suck. As she did so, she eyed herself in the mirror with one of the most genuine smiles she’d seen on her own face in a long time.

Sadie walked back into the playroom, now feeling herself in a safer mindset, and decided to push herself even further. She had gotten an idea that she knew could push her further than anything else. She tried to ignore every alarm bell in her head telling her that she was acting weird, because a piece in her heart told her how much she suddenly wanted to try this.

Snagging one of her sister’s pull-ups, she unfolded the cute little crinkly thing and pulled her pants down, and then her underwear, discarding the clothes to the corner as she slipped the pull-up over her pink socks. It felt so weird! So crinkly and plastic-y and new... but it felt so different and amazing in a good way.

Currently wearing just her shirt, pull-up, and socks, Sadie looked down at herself and rubbed her hands over her crotch. She felt very silly and childish, but for the first time in years she found that that wasn’t necessarily a bad thing. She was only worried about herself.

Feeling the crinkly pull-up wrapped around her bum made Sadie start to feel things she thought she’d long since lost. She wasn’t sure if it was her pigtails, the crinkling around her waist, or just the pure feeling of being in this room by herself with no other responsibilities; but Sadie felt so free.
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This story was written by Zander Chesney

You can find more of his content here :

https://zanderchesneyoriginals.tumblr.com/