ok I use to be a really shy kid = LOL had lots of problems but yeah if you push it all at once he will become scared and we will turn away, so I would suggest go to dinner or something and when ever the best time give him a nice kiss == if he is shy about that just make sure he does not expect it - and hold his head so he cannot run away --- easiest way to let him know he is safe and he does need to be embarased kissing you and trusting you. Men are wierd creatures - being one is even worse LOL.
If you do want to have sex with him tho the situation would be so wierd I would have to tell you that you will need to give him some time. If you do want to get him in bed and want to have sex with him again take it really slowly - I would say get together in the morning and go out somewhere sit in the park - make sure u spent the whole day with you - this way he feels more relaxed with you if he is smiling a lot = he has fun meaning he is not feeling any awkward feeling. So after you have dinner again kinna delecate situation. Get to his house/ your house again talk a lot tease - kiss and from that point on you can start the sexual moves = which again need to be very slow because some guys can get embarassed about thinking that the girl doesnt l like their penis size and **** --- again man are from another planet wierd creatures. If he is embarassed he will not be able to get it up so just take it slow and dont worrie his body will take care of the rest and he will enjoy it a lot!!!
I know this is long - I use to be very shy and at the end of highschool I didnt get a kiss from a girl on the lips at all = But again there is was this girl that liked me and the first night I was kinna of embaressed and didnt go quite well but the second night man I thought that it was the best one of my life so far

so yeah take it slow