It dont think trying for a massage takes as much guts as say going in for a kiss. If you're suggesting a massage and she doesn't want to know I would roll off (punishment, cat string theory etc), then just continue where you left off!
just touch as your speaking... when im talkin i use my hands to talk with, i will touch them on the arm and say "you get what i mean" then carry on just learn to touch as part of ur normal speaking... then u can hug them after u tease and say "im playin with ya" really quick hug an release...
u dont need an excuse to touch them if thats how u communicate...
i.e ur talkin and u look and say (with hand on shoulder lighty) do you ever get that??? then let go
yea i think that could work
rather than just asking keep it going
like mystery says rather than build up to kino just make it apart of the way you act ...