Sadly, I don't know rigging my self, I hate doing it.

Look up some tutorials for rigging.

I remember doing what you described in Maya, but I'm not sure how to describe it. It's been a long time since I practiced 3D, kind of neglected that skill. It has to do with constraints, you should be able to simply lock one of the axis on a bone to prevent it turning that way. There's a more complicated method that works better... but that's what I can't remember right now.

Tutorials are still your best bet to learn alone, it's faster and more efficient. Shouldn't be hard to find some.

Want to officially start branching into 3D art eh? Awesome! Aren't there a few scaley 3D artists that are around? They'd probably be happy to give pointers.

You should get in contact with  foxypaws. He could probably show you which tutorials to see and give advice on the complexities of 3D modelling.

I cant quite understand; if its in a hierachy then all its rotations will automatically be relative to the parent; so what are you trying to do when you say 'restrain in relation to its previous bone'? Do you just want to lock an objects pitch and yaw so an animator can only roll it?

If so, that's just locking two axies. I don't know how to do it in Max but a quick google search on how to lock a rotation axis/channel will yield immediate results.

Ahh thanks I googled those keywords and found a solution

It honestly sounds like there's a hierarchy issue, which would only happen if you're using Customized Bones and not one of 3DSMax's built in presets.
If your bone is not rotating in relation to the previous bone, it's probably also constrained to the world Origin and not the previous bone's origin [and the previous bone's origin could be the world or another bones origin, and so on].

The presets themselves are extremely customizable as well, and is one of the advantages of using the program in the first place over Blender.

Ya I googled a bit and found a solution, it was under the hirarchy, that's exactly what i was looking for

You'll want to upgrade your copy of Max to, erm, I think it's 2011 or higher that has the CAT animation system.
It's much like Biped in that it's a series of premanufactured parametric rigs, but unlike Biped, CAT has the benefit of having a much wider range of rigs, including quadrupeds and non-standard spinal attachments like proper tails, long necks, digitgrade/plantigrade feet and so on. Plus it ties together all the accessories you want to add on, such as wings and whatever else.

Rigging really isn't easy. You're going to have to sit down for a few weeks and LEARN how to do it properly.
I strongly suggest you set your real models aside, make some super basic characters, and mess around with those first, because if you try and rig your real passion as your first model, you'll end up tableflipping and never finishing it. Rigging is infuriating, slow, boring, tedious and hard.

Yea I can definitely see that. I have tried myself at rigging before but failed, though now I'm making some good progress finally.

One issue I have right now is that adding new bones suddenly seems to break the model. Like I wanted to add bones to Sam's teats but every time I assign the Verticies to them they suddenly jump to another location away from the actual bone.
Same with her forearm, I redid the bones there but they are still connected to the previous bones, but whenever I apply the verts they just slide a bit out of place.

As hard as it is I may end up redoing the entire rigging

It's good that you realise you may have to have throw the whole thing out and start again, don't be afraid to do that.

Time and time again in the past I've had a crash, lost a whole load of work that took ages, and then had to do it all over again... but in doing so, I figured out much more efficient ways to do it all and ended up making something much better for it.
Unless you're intending on animating the tits in peculiar ways, it may be better for you to look into 'weights and springs' if all you want to do is give the tits some inertia.
If you just want to be able to control nipple erectness, then I would use a morph modifier rather than do it with bones, it'll be easier to handle that way.

I'm off to a convention in a couple of hours, and will be gone for a week, when I get back though, if you need any more help just let me know, I've been using 3ds Max since version 3 :) (Now currently on version 18)

Also I should tell you this now.
Go into the Customize -> Preferences menu.
Now on the file tab, on the left select "increment on save" and make sure "backup on save" and "compress on save" are checked as well.

This will cause Max to add an incremental number on the filename each time you save.
This has 2 major benefits - 1. If the program crashes and corrupts your file... you won't of lost ALL your work.
And 2. It means you have a sort of pseudo undo catalogue in case you screw something up, don't realise for hours, and then need to go way back in time and reimport something that you've irreplaceably messed up.

Also worth increasing the number of autobak files it's set to save (again, file tab, bottom left section) and decrease the backup interval to 5 minutes or so.)

This has saved my life on more than one occasion :)

Ahh thanks thats good too know ^..^