The advice below can help you minimise the risks associated with webcams and video chatting.
some webcams and chat rooms take a while to load...
The weirdest thing is that picture is not stored on my i Phone.
Judging by the comments, restoring the phone and manually re-installing all the apps doesn’t help. I, for one, would not be happy about my i Phone taking pictures of me when I haven’t told it so.
It's also possible, if you record the conversation, that the video will end up in the wrong hands if for example your computer is stolen or things like that, but I do not think this is a huge risk.
(and of course, you do not need to record it)To be blunt, I think the biggest practical concern you have is to what degree you trust your boyfriend.
They started advertising for models on Craigslist a while ago, so I have little doubt other operators will follow suit, some of them potentially big names in the adult industry.
You'll need a Visa or Mastercard, plus all the requisites for Face Time (Wi Fi, i Phone 4) and preferably a private place to have your conversation.