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Well, from past experience I can tell you that what other females have done to me is ask for a shoulder massage, or back rub massage, and then as I'm giving them the massage with their clothes on, they say something like. 'I think it will feel better with my shirt off....', so she proceeded to remover her shirt.
The first girl that ever did that, I had no idea what that all meant, so then I continued giving the massage, and since I wasn't making a move (I wanted to but I wasn't sure if that's what she wanted), she said, 'that's so arousing', and well, that was enough for me to make my move.
The other couple of girls that did that, as soon as they asked for a massage, I knew what it meant.
Now, the other question is might be, how do you get to the massage topic? Well, once you're alone with him in his room or your room, or any other place where is just the both of you, then you can say. "My back has been bothering me lately, I could use a massage...", if he doesn't offer to give you one, then ask him "how are your massage skills..." and you go from there. Maybe there are other ways, but that's what I've experienced, and it worked for me----or I should say, it worked for the girl :)
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