Why does he keep humping me? We have messed around but he keeps wanting to poke me and hump me (with my clothes on or with his skin against my underwear). The last time I saw him he tried to do it on the sligh, at first he denied doing it, but then continued a few more times. We have always had fun together, but nothing like this. Believe me I don't want him to stop, how should I take it? Just having fun or something more?
He's seeing how far he can push the line. He wants to see where you will stop him, and how far he can really go and get away with. He figures he can keep slowly moving and pushing the line until he can get some.
I may be going out on a limb here, but it sounds like he's hoping he'll get lucky. If you don't want him to stop then don't stop him.
He's probably just having fun wanting to see how far he can get, but it's also possible he's interested in you. If you can keep him from humping you long enough you should ask him what his intentions are. If his agenda falls in line with yours then go from there.