Spy mode on Omegle is a feature that allows you to type a question (or in this case, an order - 'stranger 1 and 2 have sex') to the two strangers in the chat. Then the Strangers use that as a topic of discussion.
From your description, it sounds like he might have been on omegle, which lets you chat with strangers much like chatroulette. It has a video feature too, but your description sounds like he was using the text-only feature. Maybe he was flirting with strangers online?
Much more than that: I have written code to pit Cleverbot against Omegle users and I am sorry to say most humans aren't nearly as interesting or engaging as Cleverbot - they just want to sex-test with make-believe female partners.
If you're wondering about AI on AI though check this out.
What I'm suggesting is a confirmation dialog, like you see on tons of websites. If it's not clear what I mean, try going to Omegle, starting a chat, and closing the tab. For me, at least, I get a message saying "Confirm Navigation: Leaving this page will end your conversation. Are you sure you want to leave this page?" Same thing happens if you start editing something on Wikipedia and then try to close the tab; and Wikipedia even has an option to disable that feature (here, if you have an account).
A bit like chatroulette; you get connected to random strangers to chat with about a certain interest/topic or to answer and discuss questions. Sometimes it works out, but most people just seem to join and leave in a matter of seconds. There you go.
Also don't know if this is helpful but the ban screen is http://omegle.com/static/ban.html
It doesn't look or sound official, as you can see I also have a non-secure connection. Is this a legit ban or did someone hack it?
Fuckkkkkkkkkk im too late, but I still feel I must share. My SO and I actually met on omegle. It was awkward for about 10 mins. Then she lost her pants (shes a skeeze). Fastforward a few years and I'm enjoying the mind numbing tedium of family life.
I like to do something similar. I'll dress in a tie and button-down, visit Omegle video chat, and offer people free advice*.
I figure it's a nice way to relieve some people from the constant stream of penises, and improve their day, even if insignificantly.
*I don't offer psychological help/advice; I'm in no position to give that sort of stuff.
Did you know that you are popular enough for someone to impersonate you on the http://omegle.com/ chat website? They actually did a pretty good job promoting RiffTrax live and had all the facts straight.
Of course if that was really you.... :O