/jp/ - Otaku Culture

I'm an artist and a friend asked me to draw the art for a dakimakura. I'm sure I can handle drawing his waifu in bed in a cute/sexy pose, but this is something I haven't done before, and I don't think he has either, so I was hoping you guys could give some tips.

>He wants his waifu in sexy pajamas on the front, and a rear view on the back, because he tosses and turns a lot in his sleep and it would be weird for her to have gotten changed in the middle of the night. Autism is a hell of a drug.
>He's having the pillowcase printed at Cuddly Octopus, is that a legitimate operation?
>I don't know how hi-res the print needs to be for it to look good. Will the pillowcase printer tell me/
>Is it a mistake to honor his front view/rear view request? I noticed most dakis have two different poses/outfits on each side.

Basically I'm a pretty good artist but this is something I know nothing about and I want to do right by my bro. What do I need to know?