Murphy's Law

  This is a story about Bobby and how he spent six weeks of his summer vacation dressed as a girl when he was fourteen. He had always had a fascination for female clothing as early as age four. He has a sister, Abby, that is two years older. She always wanted a baby sister so when Bobby was a baby, and until he was four, she would dress him up in her clothes every chance she got, and they would play together until their mom would find them and made him change. No matter how many times she scolded Abby, whenever it was too quiet, she’d find the two of them playing and Bobby would be wearing a dress.

His mom took him shopping for new clothes for his very first day of school. As they shopped, they passed by the girl's section and Bobby spotted this pink satin dress with shiny white tights and black patent leather shoes.

“Buy me this one mommy,” he said.

“I can't buy you that,” she said.

“Why not?” he asked.

“Because those are for little girls,” she replied. “And you are a little boy.”

“But I like it,” he insisted.

“It's bad enough that you let your sister dress you up in her clothes every chance she gets. I’m not letting you dress up on your own either. She knows it's not right,” his mom stated.

“I don't mind, really. I like to play dress-up with Abby,” he said. “It's fun and it makes me feel good.”

“What do you mean by that? Makes you feel good?” she asked. “Just how does it make you feel good?”

“Well. I like the way her shiny satin dresses and tights look, and I like how they feel against my skin,” he replied. “They're so soft and smooth. And her boots are way better than mine too. They go all the way up to my knees and they're shiny too.”

“I think you just like shiny things,” his mom stated.

“Yeah, I do. So how come they don't make shiny clothes for boys?” he asked.

“Because as a rule, boys don't wear shiny clothes, only girls do,” his mom replied.

“Please! Just buy me that one dress with those tights and shoes,” he pleaded. “I promise not to ask for anything else the rest of the year.”

“I will not buy you that outfit or any other girls' outfit,” his mom stated. “You are a boy and that's final.”

Bobby begged and pleaded with his mother, but she wouldn't budge. So, they went home with a few new pairs of pants, some shirts and a new pair of sneakers.

As he got older, he would go into Abby's room and take her clothes and put them on. He would lie on his bed for hours reading comics while wearing Abby's dresses, tights, panties and boots. Then he had to stop for a while because Abby was getting suspicious because her clothes didn't fit. Deep down he thought that she might suspect that he was taking her clothes and wearing them, but she never said anything.

One summer day he was home alone, he was fourteen now and his mom had to go out for a while and Abby was spending the day at a friend's house. He had to use the bathroom and while he was in there, he saw one of Abby’s dresses in the laundry basket, it was made out of this semi shiny artificial leather material, it was brown, with a narrow ankle length skirt, long sleeves, high neckline, with a zipper running up the back and back buckles at the waist and neck.

He had always been fascinated with this dress. He absolutely loved it when Abby would wear it and he often dreamed of wearing it too. He finished his business, took the dress out of the basket and took it to his room then he went into Abby’s room and took a pair of her black knee boots, a pair of her black satin panties, a pair of black tights and some of her make-up, fingernail polish, lipstick, foundation, eye shadow and mascara, the whole nine yards. He returned to his room and got undressed. He put on the panties, tights and then the boots and zipped them up. Then he slipped into the long brown dress, he had to attach a string to the zipper pull in order to zip it closed but he managed to secure it.

The dress was lined with a soft smooth nylon, and it felt smooth and silky against his skin. Abby was quite a bit taller than Bobby so the dress that was ankle length on her, was touching the floor on him. And it was a bit snug around his hips and knees as well. This made the experience all the more pleasurable. As he reached back and fastened the buckle at the waist and then the collar, he noted that the sleeve length hindered his arm movements slightly.

Once the dress was secured, he carefully put on the make-up, like he had seen both his sister and his mom do many times before. He looked in the mirror, the sight of the semi shiny brown dress covering his entire body along with the boots and make-up took his breath away. And he really looked like a young, fourteen-year-old girl.

Bobby stared at his reflection until he suddenly felt himself getting excited. He sat on the bed and rolled onto his back. He was caressing his now dress-covered body, it felt so smooth and tight, he laid there feeling good. He dozed off for a little while and he woke up to the sound of his mother’s voice calling for him. It took him a few seconds to remember what he had done.

“Bobby! You up there?” she called.

“Yeah mom, what do you want?” he yelled back through the closed door.

“Supper will be ready in an hour,” she replied.

“Okay. Thanks mom,” he yelled back.

Bobby had planned on wearing the dress for the rest of the day. But it was time to take it off and get cleaned up before supper. So, he reached behind him, found the string that he had attached to the zipper pull and started pulling on it. The zipper pull tab broke off. In his excitement, he forgot to undo the buckle of the collar.

“Crap, I forgot to undo the buckle,” he muttered. “Okay. Now what?”

He undid the buckles and then reached for the zipper mechanism, but the long sleeves of the dress and the tight skirt limited his movements, and he could only just slide it an inch or so before he would lose his hold on it, (“damn, how do girls do it?” he thought). He zipped it back up. Now he was stuck, literally trapped inside the dress. His heart was racing, it was nearing supper time and his sister would be coming home soon too. No doubt she would see that her dress was missing from the laundry basket. But that was the least of his worries. Hard as he tried, he could not get the zipper down little more than an inch.

“I guess my wish would come true about wearing the dress forever,” he thought.

He had to do something, but what? He had to find the string and try to reattach it to the rest of the zipper mechanism.

He found the string under the bed with the broken pull attached to it; but how was he going to reattach it to the broken zipper mechanism when he could barely reach it with his hands? Try as he may, he could not thread the string through the small hole in the zipper mechanism. He was starting to get frustrated and hot now and starting to sweat. He frantically looked around his room; if he didn’t find something soon then he would have to face the music and call out to his mother to help him get out of Abby’s dress.

How embarrassing would that be? Him, a fourteen-year-old boy wearing a dress, and not just any dress but his sister’s dress; as well as her panties, tights, patent knee boots and her make-up. And then having to have his mom help him get out of it. Not to mention trying to explain to her why he was wearing Abby’s clothes in the first place.

By this time Bobby was beginning to regret his decision to wear the damn dress, but hindsight is always twenty-twenty. Well. If he was going to have to ask his mom for help then he had better, at least, take off the boots, panties, tights and make-up. Then at least it wouldn’t be too embarrassing with just the dress on. He started to pull up the bottom of the dress so that he could take off the boots when he realized that it had one of those narrow bottom hems. "Damn, screwed again,” he thought. He couldn’t even get the bottom of the dress up past the top of the boots to access the zippers.

He flung himself back onto the bed in tears of frustration; now he was starting to get excited again. Somehow, knowing that he was stuck inside the dress, trapped and unable to remove it, got him excited. It was like a shiny brown prison, but he knew that he had to try and figure out a way to remove the dress without wrecking it, and soon, because Abby would be home within the hour. If he couldn’t, then he would have to ask his mother for help.

Bobby’s stomach tightened into a knot at the thought. His mind was racing, and he was starting to hyperventilate. He had to calm down and think, the last thing that he wanted was to pass out and then have his mother, or worse, his sister, find him like this.

He frantically searched for a solution to his predicament and then he saw his tackle box and fishing rod, “that’s it!” he thought. He quickly opened the tackle box and frantically started searching, finally, he found one of those snaps that you tie on the end of the fishing line to attach to lures. He tied the snap onto the end of the string but try as he may, he just could not thread it into the zipper mechanism. The dress was too tight. By now he was soaked with sweat and exhausted, so he finally called out to his mom.

“Mom. Could you come up to my room for a minute?” he sheepishly asked.

“What's the matter sweety?” she asked.

“Um, I'm sort of stuck and I need some help,” he replied.

“Okay. I'll be there in a minute,” she replied.

“Thanks mom,” he said.

He sat there waiting for what seemed like forever and then he heard her come up the steps. She stopped outside his door and knocked.

“Mom. Promise you won't be mad,” he said.

“What is it?” she asked. “What's wrong?”

“Come in and you'll see,” he replied.

His mother cautiously opened the door and stepped in. Bobby was sitting on the bed in tears. She walked over and sat down beside him and put her arm around him and then pulled him to her chest.

“What happened?” she asked. “Why are you wearing Abby's dress and boots?”

He explained to her what had happened between tears and when he was finished explaining she stood up.

“Well. Supper will be in twenty minutes,” she said. “Stand up.”

He stood up expecting her to unzip the dress but instead of lowering the zipper she zipped it back up and re-fastened the buckles on the back of the dress.

“What are you doing?” He frantically asked.

“Well, you're going to wear the dress to supper tonight,” she replied.

“But mom,” he stammered.

“No buts,” she said. “Now go into the bathroom and fix your make-up and don't forget to wash your hands.”

She marched him into the bathroom and then she went down to finish supper. Bobby was sitting at the table and when Abby came home, their mom went out to meet her before she came inside. Abby came into the kitchen and gave Bobby a look over.

“All those years of me dressing you up finally paid off,” she said. “You look pretty good as a girl. I always wanted a sister mom. Can we keep her?”

“Very funny Abby,” he retorted. “As soon as we're done eating, mom is going to help me out of it.”

“Not so fast young man,” their mom said. “I think Abby is right. That dress was getting a little small for her anyway. I think it would be nice to have another daughter around for a while. If you like to wear girls' clothes so much, then wear them you will.”

“I have a lot of old clothes in my closet too,” Abby stated. “Panties, pantyhose, shoes, dresses and bras. I think I can find some stuff for “Bobbi” there.”

“What do you mean bras?” he asked.

“Bras,” Abby said. “If you're going to dress like a girl then you need to wear a bra as well. Although we'll probably have to pad them.”

“And we'll have to let your hair grow out too,” their mother added. “That way you can get it styled.”

“You're kidding right?” he asked. “You’re trying to teach me a lesson, right? Lesson learned. You're not actually going to make me wear dresses and stuff? Are you?”

“Absolutely,” their mother replied. “I told you back when you were five that you had to stop. Obviously, you kept on wearing them. So, for your punishment you will spend the next six weeks of the summer as a girl. And that's final.”

Bobby could tell that his mom was serious, so he finished his supper in silence while his mom and Abby discussed the details of his punishment. Their mom took the clothes that Abby had picked out and she altered them so that they could not be removed by Bobby. And every morning, for the next six weeks, when Bobby got up, he had to put on the outfits that were laid out for him. His mom would then secure them in place. He even had to wear them when they went to the store. The worst part about the whole ordeal was that he couldn't go and play with his friends or have them come over to play. Abby's friends, on the other hand, got so used to seeing him dressed as a girl that they forgot that he was a boy. They did make-overs and he was forced to participate. They even brought over some of their old clothes for him to wear. And after the summer came to an end, and it was time for school to start, it was hard for Bobby to give the clothes up. His mother packed them away and placed them in the back of his closet.

“If I catch you wearing girl’s clothes again your punishment will be even worse,” she stated.

So, he just made sure that he never got caught.