Well, this is quite interesting. It was being discussed on Reddit and I found this story.
Before I jump in, I need to address few things, Omegle is a fun place to be, I have been there numerous times, I have trolled, done some stupid stuff but as far as I can recall I haven't fapped there. I mean sure I did get a hardon with few lovely encounters but it never really got me off. To me this is normal, I don't care if you fap there or not but for others this might be something disgusting or new. So, keep an open mind while reading the stories.
"First, a caveat: I have never fapped on Omegle, but I used to do it a lot on chat roulette. I started using chat roulette when I was 20 and I used it like a normal person, trying to strike up conversations and meet interesting people for a few minutes. I actually really liked that about chat roulette and the rare good spin was worth wading through the muck (aptly named, I think).
So after a while of using it and becoming exposed to my fellow naked brethren, I started to wonder this same thing: "Why are they doing this? What's the big deal with polishing your lamp for people?"
The curiosity was not insurmountable but there also seemed to be no harm in sating it.
So at this time, I was also a virgin and while I don't recall feeling sexually frustrated, I definitely was. I also suffered from really bad body image issues. I was pretty overweight while in high school and had spent the past 2 years working out, eating well, and getting fit. While I can look back on that time and understand that I looked great, I didn't think it at the time.
So back to my getting naked and dating Mrs. Palmer and her five daughters: I had never used my webcam before and spent about 30 minutes making sure that there was nothing identifying about me in the view. I did this the first time during the day standing a few feet away from my webcam so my entire body was exposed besides my face and I could easily walk forward and turn shit off if need be without being seen.
The first time I tried this, I stood, in my underwear (tight, dark-blue boxer briefs with a gray trim. Very sexy) in my chosen spot and let the roulette wheel spin. It landed on a few people that clicked away without even an eyebrow raise. Eventually, someone stopped and waited. They typed something but I couldn't see it cause I was too far away.
I started to do this stupid, slow strip-tease sort of thing. I wasn't really moving or dancing but just slowly turning a little bit, flexing a little bit, moving my hands up my chest and eventually down into my boxer-briefs. The whole time I'm doing this, I am watching myself and not the person but I know they're there and the fact that they haven't clicked away excited me. It was like approval. Oh shit I forgot to mention I had the sound turned off. I didn't want to hear their objections, if any (lol).
Anyway, this process would turn me on quite a bit. The exposure, the risk, and what have you. Not surprisingly, I now thoroughly enjoy sex in public. But that's a different story.
So eventually I would drop trout and flog the molly. This, in the style of my previous showmanship, was also very slow as opposed to any other time where I'm just trying to get off. This time, there was an audience. Inevitably, I would pick up the pace a bit.
By this point, I have probably captivated some lonely guy who is enjoying the show but not before about 30-40 other people have clicked through me. Some making foul gestures and whatever. Like I said, I was usually watching myself so I didn't really care what they were doing.
The first time I ejaculated, it was the best jerkin' session I had ever had and the most powerful orgasm. (Remember: virgin at the time).
Well, after that experience, I decided I liked it more than just looking at porn and decided to keep doing it. Eventually, my IP got banned and I stopped. I had sex with another person and have never sometimes thought of doing this again.
I guess the TL;DR might be that I used chat roulette as a way to really appreciate my body for the first time by enjoying the approval of another person appreciating it, too. Probably narcissistic as fuck but whatever, man.
Hope this gives some insight."