There's nothing wrong with outright asking what gets him going (especially if you have something slightly odd that you're into- let him know you're ready to be open and have a laugh about it all, because sex should never be a strict, serious event... unless you like it that way, of course !).
Playing on your comfort zones might help build confidence- if you want to try dressing up role play style but aren't quite ready, why not let him see then end up blindfolding him so you can feel more relaxed ? If I'm wearing something for the first time, I often put my man in his blind and gag hood so I can get used to the feel of it on myself.
Excitement and spontenaity can make up for things not going to plan, so you could have a beach picnic (next summer) and end up fooling around by secretly touching up, or waiting until late when everyone's leaving to have boring old missionary sex with a twist ? (Please either do this where allowed or when you know you won't get in trouble if caught !). This also applies to things like a hot make out session just before going out to dinner- helps set the mood for the evening and gets him worked up and teased a little.
You've mentioned your discomforts, but what about his ? Buy him something you want him to use on or with you, or even dress up as; tell him a fantasy that gets you going like crazy (text it to him late at night if you're too nervous in person), and see how he deals under pressure while you're being fulfilled ? :p
Your sex and romance life is unique though, so as much as we're all here throwing our best advice, it might be better to just let yourself get caught up in any moment that next presents itself and see where it leads ?
Good luck ! <3