As a general rule you get much better service if you take the lead. Most lasses prefer that as long as it's not done in a too rough way, they get turned on more, and it's easier for them. If you want the woman to take the lead, it matters more that's she's fresh & energetic.
So you might find it makes a difference if you try and book your WG's when they're fresh - i.e. get the first booking of a day, & especially if it's on their first day back from a break (even if that's just one or two days.)
Alternatively, you could learn to take the lead yourself. You say you're not comfortable asking for things - fair enough. But that sort of confidence can be learned. And punting is easy mode for this. Chose a WG that advertises as a sub, and after introductions, a complement or two etc, say 'down on your knees' in a commanding tone of voice. You probably won't sound that confident, but she should still obey. Next time you'll be more confident, and after awhile you should be fine to take the lead with regular WG's who dont advertise as subs. (I was like you once. After I learned how to be mildly domineering, the improvement I had in service was huge, and it even led to me having some success with civvy girls, which I never had before.)
All the other advise here looks good too. Happy punting.
