I need advice. how to get back into cuckolds

Bambar

Male
Periodically I masturbate to photos of the time when she fucked with others. But I am afraid that I will be jealous, anxious and depressed again. It's embarrassing for me to ask her to cuckold me again, even though I really want to do it periodically.
Maybe someone had a similar experience of returning? How can I do this better and safer? What mistakes should I fix (maybe I shouldn't date women in parallel)? I will be glad of any constructive comments. Thanks