I'm gonna go out on a limb and guess...

that when she says 'Why don't you get comfortable?' then you take them off after removing your pants.  But that's just me

Seriously I think I can see how this could be disconcerting. Although not the same thing, I often fly through a striptease moment when with a provider. My typical strip sequence at home is to first remove my pants and then my socks.  This of course leads to the brief but  unattractive socks/undies look.  I have to try to remember to reverse the sequence when with a provider else risk that ridiculous looking moment. But sometimes they take off my clothes and they always remove my pants before my socks and... well you get the picture.

I have never experienced hobbying in absolute frigid climes so I guess the layering situation is different during the stripping phase.  But sooner or later you are buck ass naked so I suppose it does not matter how you get there.  But I wonder if shrinkage is a bigger concern in freezing hotel rooms?        

Is that by you or by her?

A Union Suit, with the backside flap raises alot of interesting possibilities.  

Seriously, having lived in a Utah ski town, flesh on flesh generates, and preserves more heat than thermals.

jazz32

Face it, in colder climates, the necessity speaks for itself... I would think it make zip difference to the lady and may even be appreciated as you will be warmer and more cuddly - and there is the added factor you are taking her comfort into consideration also.  During the winter months, when visiting a lady I make it a habit to adjourn to the bathroom and take extra care to wash my hands with warm to hot water before starting the session... cold hands can be a turnoff for anyone.