(1) When talking to him, just hold out your hand to him. If you hold out your left hand, hold it out to his right so that he takes your hand with his right hand. It’s usually hard to not take someone’s hand when it is offered, and if you like them it’s enjoyable.
(2) Once you are holding hands, step in toward him and turn your back into him.
(3) Nestle your back onto his chest while holding his hand against your stomach.
(4) Options here are the lay-your-head-back-on-him thing, leaning your head off to one side to encourage your neck to be kissed and the traditional favorite of grinding your ass into his crotch.
(5) Enjoy for ten seconds…
(6) Step back out and away from him back to the starting position in (1) and keep your hand hold going. Make intense eye contact and the so-what-are-you-going-to-do-about-that face at him.
(7) If he has a clue he will initate something further. Enjoy.
Also this is easily transitioned to when you are walking together hand in hand somewhere and come to a stop together. Just take an extra step and pivot back into him gently. Pretend he pulled you there…