Why is it that when X-23 sheaths her claws, he hands bleed but when Wolverine sheaths his his doesn't ?

Artist interpretation, I'd say. 

They don't tend to. Are you referring to something from a specific issue? It might have been pivotal to the plot or if her healing factor had been reduced.

I've just seen a few pictures like this one, not sure where its from are from:

I believe Wolverine's claws do bleed, but I think he has a little housing, cap area where his claws protrude as well, so possibly that might be the reason he doesn't as much? I think X-23 also does this a lot (sheathing and unsheathing) as a way to inflict pain. Plus its somewhat of a plot point with her to focus on the pain she is causing herself. So we would probably get more panels with her observing this. I do recall a few Wolverine arcs similar happened. 

Wolverine constantly where his blue glove maybe he used it to hide some.

Wolverine does bleed hes just wearing gloves so the blood isn't visible. I'm sure hes made a comment that it hurts every time he pops his claws. 
Laura seems to like feeling the pain though which is why there's a greater focus on this

 @Dragoness1993:
Wolverine's claws do bleed.  I think the when the claws are fully extended, or fully sheathed, the healing factor seals the wound.  If the claws are in transition then bleeding can occur, but the transition is usually quick... 
Here's an image from Uncanny X-Men 524.  The scene is Kurt's funeral.   Logan is standing with his claws partially extended.  I assume it's one of  those times he's so angry he can't get his claws to sheath.  Notice he's bleeding.
 

Yes, I've wondered the same thing before.

Hmmm... Shortage of red ink to some? :P

@Dragoness1993 said:

I've just seen a few pictures like this one, not sure where its from are from:

Thats from X-23 10.

She bled in Target X as well

@saturnssailor: In the bleeding image, there wasnt a reference to pain or emotions at all. This it was just a Yost thing because Yost is a good artist