Should I tell him?

So me and my boyfriend have been together for around 8 months, and I am very open with him except for this one thing.

I am a young, very very small business owner. It is an extremely nerdy business that has to do with computer games, and only one of my closest friends knows about it. For this business I use kik, skype, and paypal, and I don’t want him to think I am cheating over skype or kik. He’s seen the apps on my phone, asked why I still used it in a joking matter. I lied and said its old and I never deleted it. Should I tell him myself or wait till he really asks?

Edits: The reason why I am hesitant to tell him is because it ended my last relationship and this guy means a lot to me.