For transitions between video clips (as opposed to still images) you need to trim some frames off the clips on each side of the transition. This is because transitions overlap onto what is called "residual video", that is the invisable video that remains when one trims a clip. That is, the trimmed out portion does not disappear, it just becomes invisible. The residual still remains. So if you want to make your transitions longer in duration, trim back the clips to provide more residual video for the transition to hook on to.
The above does not apply to transitions between still images. When one trims a still image one is changing its duration, but it still fully displays without any portion being made invisible. Thus there is no residual footage. For transitions between still images all that is necessary is that the still image be of sufficient duration to harbor the transition. So for a 5 second transition the still images must be more than 5 seconds in duration, or 2.5 seconds on each side. If they are not, then you would drag to increase the duration, whereas with video clips you would trim back the clip to make it less duration.
As you probably know, to adjust the duration of a transition you click on the transition and set the duration in the little dialogue box that appears. If you set the transition duration beyond the available residual video, you will get a message that you can't do it.
-- Rich