"Play with it" is such a powerful phrase because it encapsulates something that's so key to this: trust.
Jealousy hurts because we believe the other person is disregarding us. Learning to put on a show, perform, and make it playful, turns it into pleasurable and scandalous stimulation.
I remember that first time I strongly encouraged Mrs. E. to try sunbathing topless by the pool at a hotel in Europe. She knew what I was interested in playing with and went with it, albeit reluctantly, knowing there was a pack of college-aged guys caddy-corner ogling her. Lotioning up and pretending she had no idea they were staring, until she finally got self-conscious and put her top back on. It was only when I got up to get us drinks that I realized I had a massive hard-on, and we ducked back into our hotel and 69ed the afternoon away.
You've crossed the first taboo boundary, intimate touch, with a light heart.