... to be an expert Pickpocket?

Wouldn't constant fist-bashing (or clawing) affect the dexterity of hands?

in real life, it would. the game mechanics wouldnt have an effect on it though.

but i assume since youre asking, you want it to be as realistic as possible, right?

Why not? After all this is Skyrim we are talking about, where one can become and Archmage who is also as master assassin favoring a greatsword...

You could image that a Fortify Unarmed enchantment could protect against that sort of wear and tear; "magic" is a great deus ex machina for role-playing efforts. You'd imagine this would particularly true if you use dual Fortify Unarmed and Pickpocket enchantments too, so go crazy. I'm also playing unarmed with thievery and hadn't even factored this kind of physicality, but if I had what I mentioned was probably how I'd rationalise it.

ha ah magic, the easy way to explain anything on Nirn.