I'm not to sure about being very ticklish everywhere but over time if you are exposed to something you become more accustomed to it. So a lot of tickling can actually make him less prone to it.
For the handjob thing it could be because he is so used to his own hand or he rarely touches the head. It may take a while for him to get used to someone else and their grip. If you use lube while giving him a handjob make sure to stroke it very light and gentle near the head and eventually, slowly build up the pace. Ease him into it.
I wouldn't worry to much about the virgin thing and penetration. Chances are he will probably be using a condom (which may help reduce friction) and you two will take it slow for the first few times anyway getting more comfortable with each other.
Ya there is really nothing you can do about him being ticklish except do your best to make you move movements deliberate and refrain from any light touches. My friends girlfriend tickles him for fun sometimes because he's so ticklish but being that ticklish seems very inconvenient not just for you imagine how he feels not even being able to get a hand job from you.
i think if he has an orgasm with you, maybe that would calm his nerves?
also, you should have him hold your hand, guiding it in stroking motions... cause you know how its impossible for anyone to tickle themselves? maybe if he's holding your wrist using your hand on himself, it will trick his brain, then when he lets go, maybe it will work. idk... totally random theory haha.
My boyfriend is also so ticklish- OK not to such extremes but I can't massage his body at all. Sometimes we will be getting intimate and he will start to giggle because I'm unintentionally tickling him. Which kind of puts me off.
I don't think sex will tickle your boyfriend though.
I get that your partner is ticklish and i may be a diff sex but im also that ticklish my fella is always tickling me during and after sex but the more he tickles me the less it tickles so id say tickle him mess around etc as that is the only way i can handle it is if i have been tickled for a while