I do it all the time.

I would be turned off. Might be better to bring speakers as well so you both can listen, but the best is to ask. I'm sure some providers could care less.

Did you visit the lady to privately listen to music or to get laid? Perhaps you are used to sitting on the toilet with your Ipod and wearing your hand out?

I plugged it into the radio at the hotel room.  Of course I asked the provider if it was OK before I plugged in.  She actually appreciated my playlist of sensual music

YES! You can't give it break for 30 min, an hr or something. If you like music that much as the female if she has some music or can go on imeem or something and whip up a quick playlist. I saw a guy who was way addicted to texting and I said if you can't put that away for the hr you're here you can do....it's just weird.

Not sure why anyone would think it weird to want a little background music. I had my iPhone playing my first time and my provider didn't seem to mind at all. During our second encounter (incall this time) she provided the music, Stevie Nicks...I loved it. So...just be sure and lose the headphones, and go for it.