This is all hysterical...you really have to take it with a sense of humour!! And we're all human!
Between Skype, Facebook, Linkedin and Whatsapp, what made me accelerate my transition was a business meeting we had to do via Skype, rather than our corporate systems, and afterwards, a colleage in a partner company who attended the meeting called to say that my girl photo was flashing up every time I talked. He was one of the few who knew about me, but I started to out myself more deliberately from that point.
Actually, I had a complete plan for gradually outing myself: Skype photo, then Facebook (almost only friends), then Whatsapp (ditto), then Linkedin (work!) and then finally our company's corporate systems. There's always some mixing of people between those applications so I knew they would generate some chatter, which was also part of the plan. The result was pretty good - a bit like alpine skiing as an intermediate - you're mostly in control, but not entirelyyyyyyyyyyyyyyyyyyyyyy. That's part of the fun!