This may sound like a dumb question but I just got a new bike. After my first week of riding and putting on about 100 miles i oiled the chain today for the first time. After I oil it is the chain supposed to produce that black grease? I know the chain is supposed to stay clean and what not but it seams like after I oiled the chain its producing a high content of the black greasy oil. Is it supposed to be like this or not?

Kinda depends on the lube you used. Chains get dirty. Just wipe excess off with a rag after lubing to keep it from getting on you and your stuff as much as possible.

After lubing your chain (with TriFlow ), wipe it until it appears almost "dry". To do this turn the crank backward and wipe the chain with a clean rag. Keep changing the rag so you're wiping with a clean section of cloth.

Crappy chain lubes will do this. Good lubes like rock'n'roll will not. If you use something like triflow (which picks up a lot of junk) then be prepared to get your hands VERY dirty everytime you touch it. After you lube a chain, you should wipe it down with a rag. There should NOT be any lube anywhere you can wipe down on the chain. It only serves to attract dust/grime.

From my experience all chainlubes turn into a black mess. tri-flow does it after one ride even if the chain is spotless before the ride, but tri-flow is easier to clean, rock'n'roll will take longer to turn into the black mess but also takes longer to clean. My preferance is Pedro's Road Rage (road) and Pedro's Synlube (dirt). they are a pretty good balance of staying clean and ease of cleaning. Both of these lubes do alright in the wet also, triflow does not last very long in wet conditions. On a side note before I worked at a bike shop I would just put some oil on the chain and wipe off as much as possible. It didn't matter if it was WD-40, 10w-30, or 90wt, after working at a shop I hate dirty chains.

Cleaning the chain, cassette, and rings before lubing is more important than the lubing if you ask me. without a good cleaning you are wasting your time.

Whichever "oil" you use, drip it onto the pivots on the bottom run of chain, directly onto the pivots, takes longer, but the lube goes where it is needed, not where it isn't. The outside faces can get rusty, doesn't really matter. The lube needs to get into the bushings. I use Boeshield T9, I've even stopped taking off the original grease, it gets "wiped" off anyway. i just run the original grease until I hear the first faint sounds of dryness from the chain, then lube with Boeshield, about once every 500km in dry conditions.