Hi, Angel, and welcome to the Shelter. Trust me when I say you aren't alone in your problem with moving the story from Chapter One to THE END. Many writers come up with the most wonderful story ideas, then experience issues with telling that story in ink, pencil, or pixels. The middle of the story can be particularly bothersome for many. It can be overcome by understanding that it's a natural condition and nothing to stress over.
A lot of your problem may evaporate as you gain experience. You've already discovered that outlines are good tools for dealing with the issue. Playing the "What If" game is another fun way of advancing the plot. Just don't get discouraged or let it force you away from the desk. It's all a part of the growth process for writers. Please keep us posted on your progress.
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