If I fill out the first two items manually with no blank line between
them and then using M-RET to edit the third I get what you want.

1. First
2. Second M-RET
3. 

Using
Org-mode version 6.36trans (release_6.36.141.gbc53b)

It does not look like it is a customizable option AFAIK.

-- 
Mikael Fornius

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