2018-07 BCTS July Staycation Story Contest

A special thank you to Penny Lane for suggesting a shorter story. This is a semi-prequel to a longer story that was what I was originally going to submit to the contest.

version 3.0

He was just over eight-years-old and stuck at home for his summer vacation. All alone in his big home, without any parents or guardians. It was normal for him, but this time something in him changed.

Little Toby Jones was a curious boy. He had no parents and lived with his extremely frugal grandparents, two tightwads who claimed that they couldn't afford to buy a lot of the things that he needed such as underwear and socks or even a TV.

He was small for his age, and had long hair that would often cause people to mistake him for a girl if they didn't know his gender already. He hated being mistaken but after getting people angry at him for their assumptions about him being false he stopped bothering to correct people.

He was left all alone for hours on end by his grandparents and was forced to find his own sources of entertainment, even if it meant breaking the rules and going places he was forbidden to go especially in his own home. He would go for long walks through the neighborhood and through the town, with most looking at him with disgust as his grandparents' neglectful nature were well known.

Before summer vacation, he would travel miles just wasting away his afternoons before going home to a small dinner then an early bedtime. He was often in ragged clothes and had a wafting body odor that would make people turn away from him or cross the street if they saw him. He hated that but with his grandparents being too cheap to buy decent soap he could only take a couple of baths a week and only after they had gone to bed for the night.

His grandparents would complain that they had to buy him basic things. He never complained nor did he fight back, they'd lose interest in a bit then move on to something else.

They would do this frequently when he lingered on clothes and toys in the stores. The managers took their complaints seriously and suspected him of stealing which made him avoid most of downtown while he went on his long walks when his grandparents were out or asleep in their room. He hated that he was seen as a bad seed, he didn't deserve the reputation nor the abuse that came with it.

Toby had read every book in his house and on his summer reading list within two days and was in search of new fun. He had explored his house and yard so much that he knew the nooks and crannies of the basement and yard to the point of offering the birds bits of yarn and sticks and squirrels some nicer acorns which led to them coming out in force to see him and get treats from him.

One place he hadn't seen was the attic. His grandparents forbid him from ever going up there but he needed the adventure and they couldn't punish him any more without hurting themselves legally. To his eight-year-old mind it was like the ultimate prize for exploring especially with the danger of his grandparents getting angry and punishing him.

After his grandparents had gone out to their daily bingo game in the hopes of winning some big prize like a free trip to Caribbean or thousands of dollars in cash, he crept upstairs and finally steeled his courage and opened the door. There wasn't any special glow, any special music, any chorus singing as he entered what was this lost oasis in his home- it was just another room, albeit dimly lit with only the sunlight beaming through the two windows.

The room was filled with boxes of clothes, all of them dresses and skirts and blouses in various sizes from ones toddlers would wear to a prom dress a teenager would drool over. They had to have been his mother's clothes, ones long since worn but in a variety of sizes and shapes. They were nicely cut as well, either homemade or top quality and looked to last the ages.

He held up one dress and felt the soft material. It was the softest fabric he had ever felt, it made his skin feel good instead of rough and was unlike anything he had ever felt before. He had to feel more of it, he had to try it on.

He got undressed and looked at something in his size, putting the beautiful red dress over his head and feeling like he was on top of the world as it slid down his thin body. It was amazing, he felt like he had transformed into a new person and as he looked into an antique mirror close by he gasped then giggled at himself as he mistook his own reflection for one of a girl who had caught him in the act.

Toby got undressed and put the dress away, telling himself that he was a boy and boys didn't do what he had done no matter how nice it felt to wear the dress and how cute he looked in it. This was a one-time thing and he'd never do it again no matter how much you paid him.

That was a lie, deep down he knew he'd be back. He couldn't do it one time without trying it again and again. It wasn't in his nature to give up so easily, especially after feeling right wearing that dress.

Toby went back downstairs and acted like nothing happened, going for yet another walk through town and doing all he could to avoid people especially ones who knew him and who would ask about his being alone. He hated that he was known to the town for all the wrong reasons, but he couldn't change that. People didn't like him because he was a small boy who looked strikingly like a girl, one you could blame for all of the troubles in the world and it would be accepted as the truth by others.

Toby kept to himself but the curiosity to try dressing again kept nagging at his subconscious. The urge built up for days until he couldn't take it anymore and went upstairs to the attic and put on another dress and walked downstairs. He saw himself in the mirror and rushed to the bathroom to shower with special attention paid to his hair to ensure that it was washed, dried, and styled right.

He looked in the mirror and saw a pretty little girl looking back, with neck-length sandy-blonde hair and a pretty smile. He loved that image. She was him but she wasn't really him, she was Molly.

Toby decided that Molly would be his new name when he dressed, he couldn't call himself Toby and she was practically a different person even to him. She was pretty and people would not say bad things about her nor would they try to hurt her like they did to Toby. People didn't do that to pretty girls, Molly would be able to live her life and enjoy her walks through town without question.

Molly dressed in a loose dress and sandals, finding a sunhat that would help give her some protection from the blazing sun and anonymity while falling in love with a pair of sunglasses that were old yet retro enough to be fashionable now. It was a bold move, but Molly needed to get out and enjoy herself and that wasn't happening there.

She walked to town, carefully avoiding houses but not noticing that her neighbors had already seen her and tried their hardest to keep their reactions to themselves. Molly wasn't in any danger, but they were shocked to say the least as they couldn't believe that a pretty little girl had been to Toby's home. She just made such a beautiful girl that several had trouble believing that someone so beautiful could want to associate with the dirty, lonely boy that lived there.

The townsfolk were kind to her as she walked through the center of town. There were dozens of people walking the streets, shopping, talking to one another and thankfully for her, she wasn't recognized by anyone that she knew. The few who said anything to her asked if she was new to town and where she was living, with Molly giving a happy "I'm new here and I'm staying on the outskirts of town with my grandparents for a bit."

It wasn't a lie since it was the truth, but they didn't need to know that. She was quick to move along and not give them much chance to question her further, but it felt nice to know that she could be treated as if she was a different person even if all she had done was put on a dress and sandals.

She enjoyed her time going from place to place and seeing how the town acted without the perception of "Toby the sissy" looming over your head. People went out of their way to help her as she entered shops and browsed the stores while looking at things to buy but not intending to buy anything.

Toby would get run off from the stores in town unless he was with his grandparents and with them he had to endure complaints about his physical condition, smell, dirtiness, and his grandparents' griping about him costing them money. He was under tight watch to the point that if Toby was in a store other kids would come in after him and steal whatever they liked while Toby was under watch. He would get accused of stealing but it was clear that he didn't have anything let alone stolen items despite claims to the contrary from the managers.

Molly had to fight off constant attempts to give her free samples of the candies, donuts, pastries, and other sweets in the candy store and soda fountain as the owners or managers tried to entice her business. She knew that she couldn't accept without being drawn in to buy something that she couldn't afford. It was the only disappointment to her being dressed as a girl, but it was an acceptable response.

As she was leaving, a group of older girls called her over and started to ask about her. Molly was quick on the draw and made up a plausible story that the girls would believe and leave them unable to ask much else without hurting Molly's feelings. The girls kept at it and for the first time Molly enjoyed being around girls her own age, especially ones who liked her for herself.

Molly spent a bit of time talking with them and noticed that they thought she was at least 12 or 13 rather than the eight-years-old that she really was. The dress that she was wearing caused her to look older, and the training bra that she added to help fill out the bust made the image stronger. Molly had to fight a blush as she couldn't believe how much she could change with simply changing her clothes.

The girls invited her to go to the library, which was tough to refuse as it was getting pretty hot in town and there was little else for her to do except return home and take a nap. The girls showed her off to other girls that they knew, both younger and older, and had her enjoying the movie that was set up for kids to keep out of the heat. It was pure fun for Molly, she was feeling"normal" for the first time and it caused her to see that maybe she might be better off as a girl than as a boy even if it could never actually happen to her.

The fun didn't last and after the movie ended and some more conversation Molly had to rush home to change before her grandparents returned. The girls were concerned about her suddenly vanishing, but one told them it was for her own good. She wouldn't say way, but being Molly's next door neighbor she knew that Toby had to reappear shortly even if Molly wanted to stay.

Molly rushed home and changed quickly, barely making it downstairs before Toby's grandparents came in to a loud yell of his name. He had been sly and ensured that the door was closed and didn't look like he had been up in the attic, but they still gave him a look that caused him great anxiety.

Toby ate and listened as they talked about a new preteen girl in town who was making friends with the town's girls. He acted like he didn't care but they droned on and on about her and how she had impressed the adults and kids. It was more of a gossip session than anything, they knew that he didn't care for other kids his age and only told him to ensure that he knew to avoid her at all costs or he'd upset the town.

When the meal ended and Toby washed the dishes, he went back upstairs and had to fight the urge to go into the attic again. It was too risky, his grandparents would know and he didn't want to be hurt for being unable to quell is curiosity and new desires to be the new person that everyone raved about.

He went to bed with tears in his eyes. He wanted to be Molly. He was Molly but she wasn't him. One day he might be her, but that was a long way off...


Toby woke up from his long sleep feeling terrible. He looked around the room and saw his grandparents upset and angry. He was in the hospital, with the doctor telling him that he had been sick for the past month with a nasty virus that put him into a coma keeping him in the hospital for much of his vacation.

His grandparents told him that he had passed out in town and been rushed to the hospital. They were upset that they had to pay a large hospital and ambulance bill due to his illness. It wasn't his fault, but they were still angry that he cost them money even if they could afford it.

It had been all a dream. His little staycation adventure was all just a fever-induced delusion. Molly wasn't real. She didn't exist, he never went up into the attic, he never put on the red sundress, he never spent a day in town, he never went to the library with the girls. Molly didn't exist, or that's what he thought.

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