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Regarding Q.1:
I usually lay on my back and let my 'girl side' arm (well, wife side now) be straight out under her neck (her on her back also), as kind of a bicep neck pillow. This should be comfortable for you to sleep, even if she's laying on her back, and it puts the ball in her court:
if she rolls with her back towards you, you can spoon or bend your elbow and grab a boob or shoulder
If she rolls into you, she can put her head on your chest and you can curl your arm around and put it on top of her hip.
It is more awkward with a first time companion, but I seem to remember following that general flow chart in my singler and more promiscuous days with great success.
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twisted no more
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