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FWIW, here's the way we do bedtime...
I think they key is to have a routine. Kids (and adults!) are often much more comfortable with a routine. Not a to-the-minute schedule, but things generally happen in the same order at about the same time.
CR usually finishes up his homework after supper, so then it's:
1) Make sure room is clean.
2) Shower
3) Pajama's
4) *if* the above is done before 8:15(ish), he gets a story
5) In bed (by 8:30ish)
6) Reading in bed for 15 minutes/or until 8:45
7) Lights out at 8:45(ish)
8) Song
Yes, we sing to all of the kids - it relaxes them, gets them ready for bed, makes them feel loved, etc. We also give them a chance to talk for a few minutes after song, though they tend to like to try to drag that part out. Each child usually fixates on a song for awhile - right now CR likes 'beautiful morning' from Oklahoma.
With this routine all of the kids do *fairly* well at bedtime. Sometimes they will pop up 3 or 4 times for drinks of water, 'Daddy, I have a question...', etc. But usually they are pretty good about it. Our 4 year old also sometimes gets up in the night and climbs into bed with us. We put him back into his own bed if we wake up enough to, but generally don't worry about it too much.
Another thing that might help is changing his sleeping arrangements. Our 9yr old has outgrown the 'cuddling' thing, but he also sleeps in a loft bed, so it's physically impossible for us to baby him like that.
You're in a bit of a tough situation though, since you aren't the kids dad - it sounds like from your message that you aren't really in a parent kind of relationship with the kid, so I think you need to respect his mom's 'parent' status. Not to say you should give in, just disagree...respectfully. :-)
Good luck!
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