When you insert a picture via Insert|Picture, Word leaves the picture selected. You need to de-select the picture (e.g. by pressing the right-arrow key) before inserting another one. Even then, if you have Word configured to insert the pictures using a wrap format other than 'in-line with text', the cursor won't appear after the picture. For the insertion setting, see:
File |Options|Advanced>Cut, copy, paste>Insert Pictures As.

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Cheers,
Paul Edstein
[Fmr MS MVP - Word]