I discovered Omegle/webcam dares just recently, so I don't have much experience.
I've been twice on omegle with a piece of paper with 'Dare Me' written on it... Just to experience a more 'real-time' dare slave feeling, instead of always doing the dares myself with no-one to see.
Mostly I ended up with guys jacking off and they weren't much fun, although there were some chubby gay guys asking me to undress and show off my body, or finger my ass.
Most of them, plus most of 'normal' people looking for a chat disconnect immediately. Maybe also because they only could see my torso up to my lips/nose. Probably makes most people suspicious about my intentions
Anyhow, roughly 5% of all strangers dared me; mostly to undress myself and/or showing my dick but also really stupid things. Like spraying hair spray in your eyes. I don't know why, but it seems to me that groups are more 'daring' and experimental than individuals. It adds in the humiliation though, when I have to put a clothes pin on my dick and swing it in front of the camera while two girls laugh their asses off and the other two are too afraid to watch, hahaha.
But once I got really 'lucky'. A cute, nice looking guy of my age was randomly selected and I thought he was the kind of person to 'next' me immediately. But he didn't! He asked what the 'dare me' was all about and shortly afterwards dared me to pull out my cock and so did he. He dared me to undress and show my ass, and he did the same. Again, he was HOT! I thought we made a great show together and I honestly didn't expect that to happen. He probably liked it too because we both jerked off and he came when I asked him to.
I wasn't allowed to cum he said... Too bad, but that was by far the nicest omegle experience
