This story begins with a night like many others I have had over the years. My wife was working late as she often does, our five year-old son was asleep in bed, and I was sitting on our bed masturbating to internet porn.
To say that my wife and I didn't have a great sex life would be an understatement. We're both well into our forties, as I'm 44 and my wife Amy is 43, and we've been married now for 11 years. Our marriage overall has had its ups and downs over the years, but it's never reached the point where either one of us wanted to give up entirely on it. By far, our biggest disconnect and incompatibility is with sex. While I often still feel as horny as ever, and have always found Amy very sexy, she often seems as if going the rest of her life without any sexual contact would be a perfectly acceptable existence for her. As far as I can tell, it's just how she is and nothing specific to me, but maybe that's naive and just wishful thinking.
It's hard to imagine Amy cheating on me or having an affair, mainly because she seems so genuinely disinterested in sex, but her job entails both many nights out and plenty of socializing, so I'm sure she's had opportunities over the years. And obviously, intimacy is about more than just physical contact, so who knows what would happen if she found another person to bond with and where that would lead. For me, I've never really contemplating cheating or finding sex elsewhere, but to be fair, I can't really remember an opportunity that presented itself to do so. I certainly don't go out of my way looking, but until I'm presented with an opportunity and turn it down, it's hard for me to say I never would.
So as a result of this whole state of our marriage, I've spent many nights masturbating alone to the endless supply of internet porn. Every masturbating night is a trip down a different rabbit hole where I'd find a video that catches my attention and then follow suggested link after link on each video until I finally find one I want to cum to. When I get to that point, I'd grab my preprepared sock from our laundry basket, place it over my cock, get to the best part of whatever video I was watching, and fill that thing with cum.
There are all sorts of porn genres I like. Some nights it would be wife sharing porn where husbands film their middle aged wives fucking ripped black guys with huge cocks. Other nights it would be oldje type porn where grandpas fuck super skinny Eastern European girls. I love casting couch videos where amateur girls get interviewed, get naked, and then get fucked. My favorite part of those movies is when they're instructed to spread their ass cheeks super wide for the camera. There's just something so sexy to me about a girl exposing her asshole on camera. Some nights I'll be really into bondage porn, or girls getting fucked by dildos attached to elaborate fucking machines. There was no rhyme or reason as to what turned me on from one night to the next, but usually when I started on a genre I would keep surfing within that genre until I came.
As luck would have it on this night, I was happily searching through Omegle videos. For those who aren't familiar, Omegle is a random and anonymous video chatting site, very similar to Chatroulette, where people repeatedly get matched up with total strangers to video chat. While I have attempted to video chat on the site myself, the problem is it's literally 99% guys on there, so if you're looking to chat with someone female, it's extremely time consuming, and in my opinion, not worth the effort.
But while it's difficult, it's clearly not impossible as guys who have more patience than I do will find actual women sometimes. And for the most part, I assume the ladies that do video chat on Omegle know what they're getting into and are probably looking for a little mischievous fun themselves. So if you do get lucky and find someone who's up for chatting, there's probably a half-decent chance she's also willing to flash you or even get naked for you during the chat. The hard part is just finding the woman in the first place.
I imagine some of these females are looking to experiment, and Omegle gives them a safe opportunity to have a guy see them naked for the first time, or perhaps for them to see a real life naked guy themselves. I'm sure others are well experienced sexually, and these Omegle video chats are just a means for them getting off. Either way, I think it's safe to assume that if a woman is getting naked on an Omegle video chat, it's because she decided ahead of time it's something she wanted to do, or at least try. One thing the site has going for it is if a girl does take off her clothes for the random guy on the other end, he's almost certainly going to be both appreciative and very complimentary because of the sheer difficulty in hitting the naked-female jackpot of the site. I can't help but think this positive feedback leads all sorts of women to come back multiple times and repeat their experience.
While these hard-to-find women chatters on Omegle are willing participants in showing off their naked bodies to some stranger, it's less clear if they realize just how many of these guys are recording their chats with the intention of uploading these videos to internet porn sites. Based on the sheer number of these videos that exist online, it's obviously pretty common practice for the guys. But if these women don't personally look at much porn online, or if they've just never seen Omegle porn, it's totally possible they don't realize that these chat sessions could ever be saved online, where they're the unknowing star.
I'm obviously a fan of these videos, as I've cum to them many, many, times. There are two main formats of Omegle videos you'll see online. The first is where the person who recorded the screen capture is showing both the conversation and the video feeds of the two participants. This gives the complete view of what transpired in the chat, but the downside is the resolution of the video, specifically the female participant, isn't as good as it could be. The second way in which Omegle videos are recorded and uploaded is where the entire video is just the woman's video feed. In this case, you get a great view of her, but you lack the full context of what's going on. Obviously, you can tell when the women is getting undressed and doing certain things, so it's safe to assume the person on the other end is instructing her to do these things. But personally, I've always found it hotter to know exactly what they are chatting about and to know what both video feeds look like at any one time, so my preference has always been for the videos that capture the entire chat.
On this night I was cycling through a number of Omegle videos. I remember one with two women together on camera, both topless and kissing each other. There was another with a middle aged woman talking with a college aged guy that was particularly intriguing as she was visibly showing him the cum on her fingers from her pussy. I almost came to that one, but thankfully I didn't, as there was a video shortly after that set a whole chain of events in motion.
I was watching a pretty typical Omegle video, but it caught my attention as it had a pleasant and somewhat innocent looking young woman in it. She was chatting with a really good looking guy, and maybe because of that she seemed to be quite the willing participant. I couldn't see her face, but I could see his. Her body looked very real and perhaps some would describe it as ordinary, but I've always found that amateur look to be extremely sexy. When watching Omegle videos, I usually will skip ahead in the video to see how long the video lasts, how naked she will get, and whether it might be worth watching all the way through. In this case, I might've ended up choosing this video to blow my load to anyway, but when I was skipping around the video I noticed something that literally made my jaw drop.
The young woman was sitting on her bed topless for her chatting companion, but behind her on the wall was a very specific poster. It was a poster from the theatre department at the high school that I worked at. Even though the video resolution wasn't great, there was no doubt I recognized the poster. I paused the video and I could clearly see the logo of our school's theatre department, as it has those two theatre mask faces you always see with the initials of our school behind it in big bold letters. I was sure that logo was unique to our high school, and I was sure that poster in the Omegle video had our logo on it.
To give you some background, I'm the college counselor at the public high school in our town. My job is to help the 90% of our graduating class that will go on to college, to find, apply, and get accepted to the right colleges for them. I spend about 2/3 of my time working with seniors, and the other third with juniors prepping for their senior year. I help them to set their class schedules, pick electives, figure out schools to visit, and of course help them with their applications. By the time each class graduates, it's safe to say I've gotten to know the majority of the class pretty well. Our high school has roughly 1000 students, so it's around 250 per class. It's a lot of people to get to know, but small enough where there are few unrecognizable names or faces.
