I can say I recommend against headphones connected to anything. They isolate too much of your hearing and personally I have too much trouble getting my full face helmet on without messing up my squishy ear plugs - even less hard earphones.
I do know that some bikers do that with no problem.
Speakers like these would be what I would lean towards.
I'd work with an ipod or similar MP3 device with any speakers with a standard connector. The neat thing with these devices are the playlists you can make, plus the fact that you can advance to the next song fairly easily and there should be a few different options for you to mount the device if you need to.
Some more examples
http://www.bikeintercom.com/products/he ... akers.html
http://www.motorcyclespeakers.net/shop/category_28.htm
As far as not knowing how the iPod works and iTunes - that isn't such a big deal as long as you have a computer, internet connection and lots of Music CDs. You probably have all three.
For itunes - go to apple.com - click on ipod + iTunes button and then click on then click on Download itunes.
It will more than likely prompt you to create an account and stuff like that. then start putting in your music CDs and it'll rip them to apple music format and if you have an iPOD you can synchronize it to your iPOD.
Then you can start creating playlists. I tend to like the iPod Nano compared to the larger models - I think this would go for the motorcycle riding as well as other uses.
I haven't tried these kinds of solutions, but I will say this - every once in a while without speakers in my helmet my ear gets bent down and it hurts! I can only imagine this would happen more with speakers in that area of the helmet. But then again, I'm one of those people with really rigid ears.
RhadamYgg