Ohhhhhhhhhh, here's one to get my amateur philologist dander up! (Great idea, Red! ;-) )

Fast - The original sense is 'firm, secure'. From 'firm' to 'strong, vigorous', from thence to 'quick'
Bolt - OE 'arrow' In the sense of 'secure', it's the similarity of form (long & narrow); in the sense of speed (of horses, veg, et al) it's from the notion of 'fly like an arrow'.
Cleave - This is an interesting one. Split. Cloven (as in hoof) is directly related. The opposite meaning derives from a word related to both clay & climb i.e. stick to!
Sanction - this is simply "to approve". Positive or negative is beside the point. It derives from the Latin "to ratify".
Sanguine - Another odd one. Literally 'of blood'. So bloody, bloodthirsty is fairly obvious. The cheerful aspect of the meaning comes from the medieval theory of humours (oddly enough, I was talking to someone down the pub about this yesterday in reference to melancholy!). Sanguine types were seen as having ruddy complexions (blood again) and optimistic personalities. Hence, cheerful. Although that sense is usually used in the negative ('not sanguine').
Ravish - to seize & carry off. So either literally (with implications), or 'of the senses'.
Try - the origin of that word is in an Old French word meaning 'to sift'. You can sort out your own interpretations of the various uses!
Blunt - Sorry, Sen, there's nothing pointed about blunt. Dull or insensitive are the OED definitions.
Endorsement - 'write on the back of...' As with sanction, nothing in the word itself says it should be positive or negative in application.
Execute - Simply, to carry out. Executing a sentence doesn't necessarily mean killing someone!
Refrain - Another good one. In sense 1 (from the French), 'bridle' i.e. something that can stop something. In sense 2, also from the French, to break up (in the sense that a refrain 'interrupts' the narrative of the verses). The French origins are different words but, I suspect if you could track it back one step further, the convergent sense is obvious.
Fatal - This does originate in the word fate, but the only given meaning of it is 'causing death'. There is no sense of 'determined by fate'.

I hope this dreary exposition is of some interest. I had fun looking up some of the ones I wasn't sure of! ;-)