I just boutht a 2006 Harley Davidson Street Bob and I was haveing trouble fineing the oil drian plug this forum was a big help

 

What has happened to your keyboard.....someone changed some keys??

 

Ha ha! man, I was swearing last night trying to get my drain plugs out and "Duhhh"
I did end up taking the two bull plugs out before refering to my manual
They were tight!! I put back in also with some blue lock tight and then drained the three correct plugs /frame bolt for engine/ tranny just behind to rear of bike /and primary just under the clutch disks.
I then went ahead and checked my oil on the stand thinking I over filled,,,ha ha "Duhhh" again!! after draining a bit of my $20 a liter motor oil, I then read in my manual to check on kickstand
READ FIRST DO LATER! Why is it so hard to follow that simple rule???
Oh and I broke my filter wrench trying to get the oil filter off and had to use pump pliers to get it off, man what a mess! Idiot put that one on, definetely wasn't only hand tightend.
2006 Night Train, Lovin it!
Hardly wait till winter is over

 

Another tip:
Drop the voltage regulator off your down tubes... 2 bolts and it's out of the way, allowing you to use a standard automotive filter wrench to loosen the filter.

 

This is what I do as well.

 

I bought the HD filter wrench for $8 and can get the filter with a 12" extension easily.

 

Sounds like the plug you pulled is a cast plug, it is referred to in the 07 Dyna manual as a Pipe Plug. It is a recessed allen head plug (no hex combo). On my Dyna (a 2007 non softail) you can't access it since the brace for the jiffy is too close to get at it.
I would think it would have drained at least some of the oil though since I have heard of guys (that have a bike that's accessible there) hooking an oil temp sensor up to the threaded opening. I always replace all three O rings when I change fluids, primary, trans, and crank. Some of my friends don't. But they don't cost that much so I do it.
Don't trust the cold dip stick reading for anything except making sure you have enough to start the engine. According to my 07 manual it should never be filled to more than half full (on the dip stick) when cold. Recheck it after warm (just in case you did not know that). I'm hoping you at least have a owner's manual.
Good luck.

 

The o-rings are a trade# 41 you can get at any hardware store, or home cheapo or lowes.

 

Last time I hit a screwdriver thru the filter with hammer
and got a good handle...