I'm writing my first real short story right now and need some tips on plot development. I had about 2 and a half pages written and the flow was good but I wanted to lengthen the story. Now it's just about 5 pages long but I feel like I watered down the plot and that it doesn't flow like it did when it was only 2 and a half pages. How can I keep the length and fix the flow?
Well, first of all, what do you mean with story? The text lenght? Or the number of events/scenes? If you want to lenghten the text, but not the plot, it's going to be hard. Maybe you will need to create more character depth, or describe what the charater(s) feel/see/hear and maybe add some interesting conversation or description that defines the history of a character? You will have to take care not to overdo it though. It is hard to lenghten the text without lengthening the story. It will feel somewhat forced. So, my advice is: Add more to the real story, and not just to the text. And with that, I can't really help, since I don't know what the story is about.
The text length is where I'm having trouble. I feel like adding the new text weakened the story instead of strengthening it. I need some ideas on how to change that. What is something that you do when you encounter this?
The best plot advice I've been given is to figure out what you MC wants and why they can't have it. If you need/want to make the story longer simply add more obstacles, make it hard for you MC to get what they want.
I've written lots of short stories and I feel that every story has it's optimal length. Some stories are simply two and a half pages long, whilst others are seventeen pages long. Half the job in writing them is to let them come out naturally. Short stories usually have time to only describe one event, or cluster of events unified by a theme and a period in time. Like a year in high school, or a party or the first kiss or... you get the picture. All the short stories I write I look at them like that. In short stories, there's no room for subplots and the plot itself is a lot smaller than the novel. So worrying about having to extend a short story, in my opinion, is not the way to go. If you want a longer story, you'll have to think of another, where more stuff happens. That'd be my advice, anyway.
I agree with Jazzabel If you have a good story that is two pages long, why would you want to lengthen it? A tight short story is far better than a weak longer one.
Kurt Vonnegut's 8 rules of writing are a nice guide for this sort of thing. I like AmyHolt's advice as well.