First-Time Guidance

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.

So when I saw our high school's poster in the Omegle video, I instantly think, "Holy shit I must know her." I start furiously scrubbing through the video to see if there are any better views of what she looks like, but it seems like she's done a decent job of not letting the camera capture her face. After just a few moments of frantically trying to search the video for more clues, I decide it's easier just to watch the whole thing through. I rewind to the beginning, grab my sock, and start watching the 7-minute long video with unprecedented attention. My heart was beating so hard I could feel it in my chest. Part of me knew it was wrong, but I'm sure that just added to the sexual thrill, and I couldn't resist watching it.

The video capture starts off from the very beginning of the Omegle chat. When they first appear onscreen, the guy is sitting in a chair and appears to be shirtless and in his boxers. The girl is sitting on a bed fully clothed, as she's wearing a shirt and shorts. When the guy sees who he's matched up with, he smiles and gives her a wave. She somewhat nervously waves back before the guy starts the conversation by typing, "hi. I'm Will"

Any hope of an immediately massive clue gets dashed as she responds back, "hi" but doesn't give her name.

Will leads the conversation and starts by giving her a number of compliments about how pretty she is. The girl responds by thanking him and also saying that Will is "totally hot." The small talk continues and Will asks her where she's from, to which she responds "east coast."

That's a pretty vague answer but it does line up with our location. Will clarifies, "eastern US?"

It's at this point when the clue that cracks the case comes. She responds, "yeah, USA" but then adds "but I was born in South Africa"

When I saw that, I realized it was a major clue. This young women was clearly trying to obscure her identity on this chat, but she just gave a way a very unique detail about herself. And while I didn't know off hand of any students from South Africa, I was pretty sure I had the means to find out exactly who she was now.

I paused the video and switched over to login to our school directory that I have access to. I'm super nervous as I'm doing this as it takes me three attempts to even get my password right. But I get in and immediately bring up the first name I see, and start scrolling down that student's info. And there it is right in our directory, "Place of Birth". I knew I had remembered seeing that before, and to this day I don't know why it would be included, but there it was.

So I take a second to regroup, and then I decide that before watching any more of the video, I need to investigate this clue. I start by filtering the directory to only include seniors and then I just start going down the list of females one by one. I realize shortly in, that not every entry has this birthplace field populated (maybe 10% of students were missing it?), so I consider the mystery Omegle person could be someone with a blank field. The first couple female blanks I get to are pretty easy to rule out. I know both of them, neither of them is into theatre, and they also don't resemble what I've seen of the person in the video. Everyone who has a place of birth listed that's not South Africa though, I feel confident in ruling out. I keep scrolling through checking one by one.

After I'm probably 2/3 of the way through this list of senior class females, I'm about to click on the next name, but when I see it, it makes me go "hmmmm." It's a student named Emily that I've already met with a handful of times. What made me pause was I distinctly remember her describing herself as a "huge theatre nerd". Not only that, but from what I remembered about her appearance, it seemed at least plausible that she could be the one in this Omegle video. So before clicking on her record, I think to myself, I wonder if she's going to have a blank answer under her birthplace. I go ahead and click, scroll down, and it practically jumps out of the screen at me, Place of Birth: Johannesburg, RSA.

"Holy fuck." I audibly say to myself. My thoughts then immediately go to what I know about Emily. We specifically had talked about how she was doing the school play, but that it would be good to expand her extracurricular activities beyond just theatre. I remember she's definitely not into sports. She's a super nice and sweet person, and she's quite smart. I remember we discussed what it would take for her to become either valedictorian or perhaps salutatorian. All of it was very normal conversation I might have with a student, but now every detail was somehow much more relevant.

Ironically enough, I don't remember much about her appearance, and specifically her body. I can definitely picture her face, and my recollection was she was relatively pretty. I remember she has brown hair, but I couldn't tell you much else specific about her appearance. Again, nothing about her body stood out in my memory. I remember her being of average height, so I'm guessing she's like 5'5"? She was probably on the skinny side, but wasn't athletic either as she clearly wasn't into sports. She definitely didn't have a body that would stand out among other high school seniors, but from the perspective of a middle-aged man, it's hard to imagine her not having a very appealing figure to someone like me. Either way, there was no question the person's body in the video could've matched hers, plus there were points where I could see the young woman's hair in the Omegle video and it looked like it could be the same shade of brown that I remembered too.

Based on the huge South Africa clue and the theatre connection, there was no doubt the girl in this video is Emily. But then I realize there's one HUGE detail I still haven't checked. I'm still on her directory page so I quickly scroll up and check her all-important birthdate. I'm genuinely relieved to see her birthday is September 19th. She's just past the typical cutoff date, so that means she's old for her class. And most importantly of all, I confirm the math on her birth year and she's been 18 for a few months now. Thank god.

I switch back to the Omegle porn video and check the date on it. It was uploaded 10 days ago. I'm again relieved as it seems like the timing all works out and Emily was certainly 18 when this video was made. If she hadn't been, I'm pretty sure this whole story would've ended right here. But as luck would have it, she was legally old enough to be doing what she was, and I certainly wanted to see exactly what she had done.

I go to hit play to resume the video, but to be honest I probably did hesitate for a brief second to think, "Should I really be watching this? Isn't this such an invasion of Emily's privacy?" Maybe a stronger person would've closed the browser and never watched it, but I certainly wasn't that strong. I just couldn't help myself.

The video picks up right where I had left off. This guy supposedly named Will is continuing with the small talk and Emily is answering his questions without hesitation. Will steps up the line of questioning and asks, "are you a virgin?"

"i am" Emily types in response.

Will follows with, "do u masturbate?"

"I do. do you?" Emily asks.

"of course" Will types. And then he adds, "would u want to help me right now?"

It's such a classic line from these Omegle movies. The guy asks the girl to help him masturbate, which is basically his way of asking her to get naked.

Emily simply respond, "sure" and then immediately stands up on the bed and drops her shorts down. She kicks them off to the side and sits back down making sure her face never dips below the top of the camera's range. She is still wearing underwear and a t-shirt, but now her legs are on full display with her underwater the only thing left hiding her pussy. Her legs are beautiful. They look long for her height and yet they appear to be so tiny, as her thighs are noticeably skinnier than my wife's thighs. I also couldn't help but notice that Emily knew exactly when to start stripping for the guy after he simply asked for "her help" which made me think she had done this sort of thing before.

After seeing her take off her shorts, Will stands up and takes his boxers off revealing his cock. It looks to be a decent sized cock, but the main thing the dude had going for him was being in great shape. He has legitimate abs and clearly was someone who worked out a lot. This was not lost on Emily as she wrote, "you have such a hot body"

"thx :)" Will responded. And then he said, "so i'm dying to know, what are you gonna take off next, your shirt or your panties?"

With that, Emily immediately slid off her basic white panties, tossed them off the bed as well, and wrote "my shirt ;)"

"your hilarious" Will wrote back "and so fuckin sexy!" He then complimented her now visible vagina, "your pussy looks delicious!"

With this, the video was clearly getting hot and I couldn't help but imagine the previous conversations I had had with Emily in my office. I have a desk where I sit behind and there are three chairs that face it. I have three because sometimes I'll meet with a student and their parents, but sometimes it's just the student. I'm now looking at this video and see Emily sitting on her bed with her legs spread and her pussy visible and I'm picturing her in that same position but instead with her sitting in a chair in my office. It's so fucking hot I have to stop holding my own cock or otherwise I'd cum.

One minor downside of this super hot porn discovery is the video quality isn't great. The resolution is grainy, and there's no sound, but in the end it doesn't really matter. All that matters is this 18 year-old girl is so sexually curious she's chatting with a complete stranger online and showing him her vagina. And I know how sweet and responsible this girl is in real life, and the combination of the two is just so fucking hot to me. I'm sure the fact that my wife would never in a million years do something like this makes it even more desirable. Being with Amy for so long has certainly made me jaded into thinking women just aren't sexual, but this was a real life reminder that there are actually females out there that are every bit as horny as I am.

At this point, Will starts pumping his cock up and down and this time without being asked, Emily lifts her shirt up over her head. She's not wearing a bra so now her tits drop back down and are hanging out in all their glory. I certainly had never pegged her for a girl with big boobs when I had seen her in person, and even in the video they were deceptively larger exposed than what I would've expected. They were perfectly round, bouncy, and looked pillow soft. I'm confident they were C cups. Definitely bigger than my wife's B's and probably not a D cup. They were milky white, in fact her whole complexion was quite pale. Again she wasn't athletic in the least, so I'm guessing she didn't spend much time outside in the sun. Now that I could see her completely naked, I could see she didn't have any significant tan lines either.