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.
After completely undressing, Emily leans forward and types into the chat, “what’s next?”
Will continues jerking off with one hand and types with his other, “play with your pussy.”
“ok” Emily responds and then scoots herself even closer to the camera. She takes her elbows and uses them to spread her legs as wide as they go, and then she starts rubbing her clit with her hand. Again, the resolution isn’t great so it’s not like I have a clear look at all the details of her pussy, but there are few things I can make out. It’s noticeably pink, like the whole region has a flush color to it. She also has big meaty labia that look so deliciously suckable. She has quite a bit of pubic hair, as her mound is pretty well covered with her pubes. She doesn’t seem to have any hair to the sides or below her pussy, so it seems to be just a full bush above it. There’s no doubt though, her pussy is gorgeous and watching her rub it makes it even hotter.
Will continues to masturbate and types that he’s about to cum. Emily responds that she wants him to and that she will too. She then leans back and lies down on the bed, but she makes sure to put her hand up in front of her face to obscure the camera. Once she’s down on the bed, she continues to rub her clit and even lifts her knees up to help with the process. After about 30 seconds of this, I can see her hand stop moving. She takes a second, sits up without revealing herself and types, “I just came.”
When Will sees this he steps up the intensity of his jerking and while sitting in his chair he starts cumming himself, shooting sperm up onto his chest. While this is happening, I can see Emily sitting still and I’m assuming watching intently. The whole scene is hot and surreal.
There’s only 30 secs left in the video so I watch it through to the end. Will thanks Emily for helping him and mentions they should chat again sometime. Emily responds “sure” and then closes the chat and the video stops. I’m so blown away by what I just saw, and there’s a ton to process, but first I really need to cum. I rewind the video to queue it up to the part right before Emily lies down and cums, and then I reach and grab my sock. I don’t hold back, and when she orgasms from her fingers, I furiously jerk and blow an enormous load into the sock covering my dick. It’s a huge release and feels so good to cum at the same time as Emily.
Immediately after I finish orgasming, I start feeling guilty about what I just did. I think about how it’s very likely Emily has no idea this video is on the internet, let alone that someone who knows her has seen it. And I start to wonder, should I try to do something about this? I still have the video open in my browser, and on the page I notice there’s a “report video link” so I click on it. The link takes me to a page for the pornsite where I’m presented with a list of options for why I want to report this video. I can check as many criteria I want and then there’s a “submit” button.
Looking over the options, there are two that I consider. There’s one that says, “actor or actress is not of legal age” and another that says “video was uploaded without performer or copyright holder’s authorization”. I know the first legal age complaint wouldn’t really be true, but how would they know? I figure the second one is definitely true. I’m not sure why but I select just the copyright one and click submit. I have no idea if it’ll have any chance in getting it removed, but there’s no doubt submitting the complaint helped me feel less guilty. Before closing the browser, I make a mental note of the title on the video listed on the website so I can search later to see if it gets removed. The person who uploaded it had named it: “Innocent Omegle Girl Cums For Hot Guy”. It was a fair enough description and one I figured I could remember without having to write it down.
The next week at school, to say I had an eye out for Emily was an understatement. I kept looking around the hallways at various points during the day to see if I could spot her, just out of pure curiosity. I did end up seeing her a few times and couldn’t help but try and reconcile what she looked like there in school with what I had seen online. Not surprisingly, she looked and acted totally normal in the few instances where I caught a glimpse, and why wouldn’t she? The more I saw her though, the more I tried to analyze her appearance and what she looked like. There still was nothing that set her apart physically from her classmates, and I got the sense that she didn’t garner much attention from the guys in her class. If anything, I think this was probably due mostly to her clothes, as she seemed to wear very modest and unremarkable outfits. And when you compare that to the attire that some of the other high school girls would wear, it’s no doubt the guys never paid any attention to Emily. But for me, I couldn’t help but find her to be very attractive physically. Part of it is there’s just a fundamental difference between the youthful appearance of an 18 year-old’s body, compared to someone my wife’s age, so I couldn’t help but be enthralled, even if her male classmates took that for granted.
I had spent a number of years, not just in this high school, but other schools as well, and I honestly couldn’t remember being attracted to a student like this before. So it’s safe to say my obsession with Emily was 100% related to knowing this secret of hers. To me, the idea that a young woman would have this hidden perverted side to her was so damn appealing, and it made me realize what I’d been missing all these years with my wife Amy. It made every aspect of Emily attractive to me, from her sweet personality to her teenage body. As the days passed by, I couldn’t help thinking more and more about her.
There was no doubt I was becoming obsessed with her, and as a result I definitely started to have doubts about whether I was crossing some seriously immoral line here. I kept asking myself if 18 was too young for a middle-aged man to fantasize about, even if it is just a fantasy? But then I asked myself, if not 18 then what’s the cutoff? 21? 25? There should be some hard line somewhere, and it sure seems like our society has concretely determined that 18 is that line. I mean after all, 18 year-olds can vote, can join the military, and can pretty much do everything else in society except drink. Who am I to argue with that? It certainly may make me pathetic, but I concluded that what I was doing wasn’t immoral. At least that’s what I kept telling myself.
At home that week, there were again a couple of nights where I was on my own and I spent them repeatedly searching through more and more Omegle videos. I was hopelessly trying to find if there were any other possible videos of Emily out there. Despite a handful of hours looking, I hadn’t uncovered any new ones. At the end of each night of hunting, I would inevitably search for the original video of her, confirm it was still there, jerk off to it again, and then submit another complaint to take down the video. This pattern repeated probably 3 or 4 times. I did start checking both of the complaint reasons before submitting, as I thought that might be more likely to result in it getting deleted. Despite the fact I would lose the best piece of jerkoff material of all-time, I genuinely was hoping the movie would get taken down.
The following week started out with more of the same, but soon enough there were two big developments. After a night of tons more Omegle videos without anything new of Emily, when I went to conclude with yet another watching of the original video, it was nowhere to be found. I had no idea if my reporting the video was ultimately responsible, but regardless, I felt relieved that it was finally gone. Somehow it brought closure to the whole ordeal and also made me feel like my good actions could possibly have outweighed my bad ones.
Knowing that her video had been removed didn’t actually do anything to dampen my overall horniness though, and the very next night I was right back at it, clicking through links of more Omegle videos. And that’s when the second big development of the week happened. In the middle of my searching, I finally came across a new video with Emily in it. There was no question it was her, and the date on it showed that had been uploaded only 2 days before. Holy fucking shit. Again.
This video was a different format than her first one though, as the screengrab only showed the video chat of Emily. It had no visible text conversation and no view of the other participant. After watching that first video of her over and over, I had no problem at all recognizing both Emily’s body and her bedroom when I saw them in this new video. Ironically, this video was filmed at a slightly different angle and that all-important theatre poster that originally tipped me off was not in view. In fact, if not for the first video to match it to, I don’t think I ever could’ve known the identity of this young women in the second video was Emily.
While it was harder to tell what all was going on without the full screen grab, it was pretty hot to have a higher resolution view of Emily in this new video. In it, there was a few minutes of her sitting and appearing to type, but shortly into the video she starts undressing. This time she went completely topless first, then just in her panties, then totally nude. Once she was naked, she wasted no time spreading her pussy open again. With the better resolution, I could see even more detail and it was just a glorious vagina indeed. Big beautiful juicy pinks lips, and a nice natural look of pubic hair on top.
Not only did I get a great look at her pussy, but halfway through in this new video Emily flips over and gets up on all fours with her ass to the camera. And yet again she managed to reposition herself without giving any sort of a clear view of her face. She clearly took the idea of not showing her face very seriously. In this instance, I’m guessing she got on all fours because she was instructed to do so, as next she proceeds to pull her ass cheeks apart with her two hands, exposing her gorgeous virgin butthole. This seems like the sort of thing the guy on the other end of the conversation must’ve instructed her to do. Now, despite her apparent lack of shaving around her pussy, there didn’t appear to be any hair in sight around her asshole or ass crack, so I assume she was still just naturally bare there.
Seeing her spread asshole was just amazing, and it also caught me totally by surprise. So much so that I couldn’t help myself and basically started cumming on the spot. While I had already been gently masturbating as I watched this second video, seeing Emily in that position instantly pushed me past the point of no return and I had two choices. Remove my hand immediately and risk a brutal aborted orgasm, or just give in and explode full force all over myself because I wasn’t prepared for the cum. I chose the latter and exploded with pure pleasure, but since my trusty sock on my cock was nowhere to be found, the shirt I was wearing took the brunt of the mess I made. In the end it was no big deal and totally worth it though.
But what to make of the fact that there was now a second Emily video out on the internet? So many questions ran through my mind. How often does she chat on Omegle? How many captured videos might there be? Have any of her classmates ever found one of these?
It was that last question that I really started to think about. I was assuming both that Emily did not know these videos existed, and even if she did she certainly wouldn’t want people she knew to see them. She went to great lengths to hide her face in the two that I had seen, so I think it’s safe to assume she valued her anonymity. How mortified would she be if some senior guys found it and shared it around school? That would have to be horrifyingly embarrassing.
I did my due diligence on this new video and clicked the report link, just like I had with the first one. I made sure to check both the copyright and underage reasons again as well. But even after doing that, I started seriously thinking that perhaps I needed to warn her that she was creating this catalog of porn videos online. I genuinely wanted to do it to help her, but I was at a loss as to how.
My first thought was that I could somehow leave her an anonymous note, warning her that her Omegle chat sessions were being uploaded to the internet. But the more I thought about this option, the creepier I realized it would have to be. There was just no way for a warning like that to come anonymously and not be creepy as fuck. If she got a note like that, she’d have to be terrified not knowing who sent it. But I couldn’t possibly send a note and sign my name to it either. That would not only implicate me directly but also document it with undeniable proof.
Then I started thinking about the only other option I could come up with, which was somehow warning her in person? If I did that, there would be no evidence of a note, and I also could control the way I explained it better. I’d be able to see her reaction in real time and adjust my approach if necessary. But how the fuck would I do this? How could I possibly explain all of this to her in person? And then I started questioning my intentions. Am I considering this because I legitimately want to help her, or am I getting some secret thrill out of this idea as well?
The only good news is that I had a built-in way to meet with her one-on-one. She was legitimately overdue for a sit down to discuss her current application statuses, so I’d have no problem getting a meeting scheduled. Could I do this though? I spent a week or so debating whether I wanted to go through with discussing this with her or not. I considered the possible benefits, which was mainly helping her avoid an embarrassing discovery by one of her classmates, as well as putting my conscience at ease for jerking off to her in the first place. The downsides were obvious too, embarrassing her greatly by making her aware these videos exist, as well as putting myself at risk by bringing up this clearly inappropriate conversation with a student.
One thing I was confident about was there should be zero criminal risk for me in this instance. I know some states in the US have actual criminal laws in situations where a school employee has a sexual relations with an over 18 student. Obviously, all states have criminal laws for under 18 relationships. But a few years back our high school had a well known scandal between a female teacher and an 18 year-old male. Long story short, the teacher lost her job but had no criminal consequences.
This situation is much weirder than your typical illicit student-faculty romance. In this case, I was simply looking at pornography online, which is clearly my right, and as a result of something I learned I would be trying to help a student in need? I get that that is a very sympathetic spin on what I would be doing. And if this all somehow became public, would I expect people in the community to see my point of view? Ha. Fat fucking chance. I’m sure everybody else would see me as some pervert who deserves to lose his job. But to be totally honest, I am a pervert, so they wouldn’t be totally wrong. After a few days, I thought it over and basically decided, Fuck it, I’m going to very politely, maturely, confidentially, and perhaps vaguely, explain to her that there are videos of her on the internet and she might need to be more careful going forward. My mind was made up.
The next day at school, I asked our assistant to set up meetings with about a dozen students I was due to sit down with, with one of those being Emily. The various time slots got added to my schedule, and as luck would have it they added a timeslot to meet with Emily right before my lunch, which meant there’d be no issue if it ran long, and maybe more importantly, there wouldn’t be another student waiting outside when she came out, in case she was shaken up.
The day came for our appointed meeting and I was nervous to say the least. I was able to get through the earlier meetings on my schedule without letting on how distracted I was, but 11:15 rolled around and Emily knocked and came into my office. As I had mentioned, I had met with her a few times before so to her this meeting was totally routine, but to me it certainly was not.
The first thing I took note of what was she was wearing. She had normal looking jeans on (no holes or anything too trendy) and was wearing a very modest sweater. As she walked in to sit down, I couldn’t avoid a brief stare at her crotch, where I was trying to imagine the pubic hair I knew existed to be hiding. As she came over to her seat, I stood up and shook her hand like I always do to anyone I’m meeting with. I tried to keep eye contact but now I was left thinking about her tits beneath her sweater. Once again I realized how deceptively big and nice her boobs are because the view I had gave no indication there were solid C’s under there waiting to fall out. All in all, it was so arousing to see her up close.
“How’s it going?” I started off the conversation with.
“Great!” Emily responded. “I think I have my final list of schools all set.”
“Awesome. Is Georgetown still your first choice?” I asked.
“Yep. Georgetown and Wake are my top two. Either one I’d be super pumped if I got in.”
One nice thing about Emily that was totally unrelated to everything else was she had very attainable “reach” schools. A lot of times I deal with kids that tell me Princeton is their reach, when I’m not even sure they’ll get into Rutgers. Emily was the opposite, as I thought there was a decent chance she’d get into every school on her list.
“That is great.” I let her know. “If you just keep up what you’ve been doing, I’m very optimistic.”
And with that she gives me the biggest smile, and oh my god her innocence just compliments her secret sexiness just so well to me, it’s such a huge turn on.
We discuss a few logistics about the application deadlines coming up and what she still needs to do. There’s honestly not much to go over in the meeting so it gets to the point where it would normally wrap up pretty quickly. And it’s at this point where I realize it’s now or never and I have to decide whether I’m going to say anything. I silently take a deep breath, come to my decision, and decide to take the plunge.
“So Emily, I have one other thing I wanted to talk about briefly here.” As I say this, she seems totally fine and I continue. “To be honest, I debated whether I should say something or not, because doing so is probably putting my job at risk.”
This causes a minor look of confusion to come across Emily’s face, but she still seems relatively at ease.
“But as inappropriate as my saying something may be, I thought it was more important to warn you than risk not saying anything at all.” I try to preface this conversation as best I can, and Emily at this point seems slightly alarmed but very attentive, which is probably what I was hoping for. I then start to explain everything, but purposely keep it in the abstract.
“So there’s a video chatting website called Omegle.” And with this sentence I see Emily’s mouth kind of slowly drop open and I swear the color in her face immediately retreats to leave a ghostly white expression.
“Now there’s absolutely nothing wrong with people chatting on this website.” I stress. “But what a lot of these people don’t realize is that the other person they’re chatting with could be recording the video of their conversation so they can upload it to the internet.”
At this point I pause ever so slightly to see if Emily is going to say anything but she looks quite confused and not ready to say anything.
“And so all I wanted to let you know is that it’s important people know that other people might do this. That’s it.” I conclude, and after I’m done I realize I have no idea how that came across, or if this was a historic mistake I just made.
I give Emily more than just a few seconds so she can process what I said. I continue to wait for a response, but she’s not looking at me, she’s just kind of looking straight ahead at nothing. Eventually, I add “I’m so sorry if what I said is awkward. I debating not saying anything, but I decided I should.”
Another few moments pass and then Emily finally breaks her silence. “So this means… that you saw…” and with the word “saw” she kind of trailed off and didn’t finish her sentence.
I interject and try to explain further, “It means that I’m the pathetic one who looks at videos like this online.” As I try to turn this on me a little bit. “And there was one time where I saw someone that I recognized, and so I closed the video and figured that I would let this person know what had happened to them.”
I blatantly lied with the part about immediately closing the video, but I was selfishly trying to make both of us feel better. I also didn’t think it was necessary to go into the details about how I reported the video and one got taken down, so I just kept it simple.
After what seemed like forever, Emily stood up and for the first time since I explained everything, looked at me and said, “Do you think you could make sure not to ever tell anyone about this?”
“Absolutely, I swear I will never tell another soul.” I assured her.
And with that, she didn’t say another word and slowly walked out of my office. After she left, I tried to take stock of how that went down. My first thought was a question, which was: Did that go how I was hoping it would? And then I realized I had no idea what I was hoping would happen, but that realistically it probably went as well as it could’ve. I was worried though that after seeing how she reacted, that I had seriously traumatized Emily and it wasn’t worth any supposed benefit. Needless to say, I was pretty distracted at work the rest of that day and the next few. I even took a break from my nightly masturbating and Omegle video hunts because I just felt super guilty about everything that had happened.
Eventually, about a week after our discussion, my mindset finally started to return to normal. But then, the next morning I come into work and look over my schedule for the day. And on it I see an appointment at 2pm for a student-requested meeting where the note the assistant put in was, “application questions”. The student is the noteworthy part though, it’s fucking Emily and she apparently asked to meet with me!
I have no idea what to think. This whole week I had been laying low because I didn’t want to casually run into her. What did she want to meet about? After thinking about what had happened was she pissed? Or maybe she just wanted more of an explanation? Or maybe it actually was a meeting regarding her college applications? That last one seemed pretty unlikely.
Anyway, 2 o’clock rolls around and I’m anxiously awaiting. I hear a knock and I signal for Emily to come in. My first impression is she seems ok, relatively normal, if not slightly more subdued than she had been entering our few previous meetings. She sits down and I great her, “Hey Emily, how’s it going?”
“I’m good.” she says with a straight face that doesn’t tip her hand regarding her mindset or the purpose of this meeting.
“So what can I help you with?” I say, basically putting her on the spot.
“I had a question.” She responds before pausing.
A few seconds go by and since she hasn’t continued, I say, “Ok?”
Emily then says while kind of looking down at the floor, and definitely not at me, “How do I know if someone is recording a video chat I’m on?”
I’m pretty relieved when I hear this question, because it clears up that she’s not upset at me. Plus, it’s a pretty easy question to answer.
“Unfortunately, you can’t.” I let her know. “If they can see it on their screen, then they can record it. And as far as I know there’s no Snapchat like feature that could alert you when they’re recording it either.”
“Ok.” She acknowledges.
Then I just kind of reiterate, “Yeah, you just have to assume everyone is recording you. It’s just the way it is I guess.”
I wonder if that’s going to be the end of our meeting because I don’t know what else there would be to tell her. But then Emily asks a loosely related follow up question, “When you chat, do you record your conversations?”
This catches me by surprise, but I have no problem answering it honestly, “I actually don’t ever video chat myself, I’ve just seen the videos other people post online.”
When I say this, it causes Emily to look up and make eye contact with me. She’s still got a pretty serious look about her and then she simply says, “Oh, ok.”
I expand a little bit and say, “But to answer it hypothetically, I’m sure if I did ever chat, I would never record it. I would be content just enjoying the chat in the moment and that would be enough for me.”
“Yeah, that’s probably what I assumed guys were like.” Emily says with a little more pleasant and normal tone than she had previously.
After she said that, I really didn’t know what to say next so I basically just kind of sat there and made a subtle what-can-you-do-gesture. Emily gave me a sheepish smile and didn’t immediately do or say anything either. I kind of assumed she’d get up and be on her way, but then she dropped the bombshell I’ll remember for the rest of my life.
“It seems like the only way I could know for sure I’m not being recorded is if I chatted with you?”
She delivered the line without a smirk, laugh, or any other inclination it was a joke. The only way to take it was that it was a serious proposition. Holy fuck.
“Uhhhhhh” I utter as I’m stalling for time thinking how in the world I should respond. “Yeah… I definitely wouldn’t record you. That. Is. For. Sure.” I say very slowly and somewhat quietly. And then I ask the only question I could think of, “Are you being serious?”
“Yeah, I think so.” she says. “Would you want to chat?”
Emily’s speaking somewhat normally here but my heart starts racing and I also significantly lower the volume of my voice as if I’m worried someone might hear us even though I doubt there was much risk of that being in my office.
“Wow.” I half whisper and half just mouth. My mind is racing. What do I say? I would fucking love to video chat with her. I mean it would instantly become the most erotic moment of my life. But could I do this? Ultimately any rational reasoning I may have had got steamrolled by sheer desire, and I responded, “Yeah, I could do that if you wanted to.”
And when I said that, Emily all of the sudden had a look of relief wash over her and she broke out into somewhat of a smile. “We should do that.” She said in a happy but more quiet tone as if she understood my nervousness.
“When do you normally chat?” I ask her, still speaking in a hushed tone.
“Anytime after 9 really” she quietly answers back. “Any night this week works probably.”
My mind is racing. I immediately try to remember my wife’s schedule and I’m pretty sure she’s got a work dinner the following night so I suggest, “How about tomorrow?”
“Ok.” Emily answers with a smile.
I then remember that one thing I do know about Omegle is they have keywords, and so I come up with a plan on the spot. “Tomorrow night, let’s say 9:30pm. Let’s both go to Omegle and add a keyword of ‘Georgetown’ to our chat topics. Are you familiar with how the keywords work?”
“Yeah I am, that works. ‘Georgetown’ it is.”
“Ok. I’ll see you then?” I conclude still practically whispering.
“Yep!” She says and turns and heads out the door.
Oh my fucking god I think to myself as she leaves and I’m left sitting there floored by what just happened.
That night I’m home with my wife and son and I’m pretty distracted to say the least. I’m horny as hell, but I’ve already decided I don’t want to jerk off before tomorrow just to make sure I have a huge build-up. Obviously, all I can think about is Emily and what our chat will be like the following night.
If it’s just the two of us, I assume she’ll show her face? Maybe she still won’t though? Will she want me to give her commands and instructions to follow like the guys normally do on these chats? If so, what should I have her do? In the two videos I’ve seen, she hasn’t used any objects on herself, would she do that for me? That would be so hot to watch her fuck herself! So many questions, and still a full day for me to obsess about it. And none of these even addressed by far the biggest question of all, is this video chat going to eventually lead to something more? Like a full blown in-person affair?
This potential chat with Emily came out of the blue so fast, I didn’t even bother to stop and consider if it was crossing some line regarding cheating on Amy. In my mind, I was just brushing that off as something I would deal with later. Maybe it was the state of our marriage that made me not care, or maybe it was how illicit the situation was regardless of my being married, but either way, the cheating on Amy aspect barely even crossed my mind. That’s certainly a sad commentary on the state of our marriage, but that’s just how it was.
The next day came and it felt like the school day was dragging on forever. I again was trying to avoid any accidental encounters with Emily so I mostly just stayed in my office. Once I got home, I was constantly checking the clock to see when I could put our son down for bed, and once that was taken care of I started prepping for the big event. I took a shower and tried to trim my body hair as best I could, but to be honest all of that was probably pretty pointless in preparation for just a video chat. I mean it’s not like she could smell me through the camera?
I checked in with Amy to see how her dinner was going, and she responded that all was good so it seemed like there was no chance her plans would end earlier than expected. She most likely wouldn’t be home until around midnight. Eventually, 9 o’clock came around, and even though it was still a half hour away from our agreed upon time, I grabbed my laptop and got ready.
I took the computer onto my bed and got myself comfortable. I was wearing boxers, mesh shorts and a plain blue t-shirt. I opened up the laptop, brought up Omegle.com and entered the Georgetown keyword. It was only 9:05, so I was clearly early, but I figured I would log on now and see if perhaps Emily was also running ahead of schedule. I double check that the webcam on my laptop screen is pointed low enough it won’t show my face until I matched with Emily, and then finally I went ahead and clicked to join a chat.
Omegle tells me it’s looking for people with common interests, which takes a few seconds. Apparently, Emily wasn’t on yet because it fails to find anyone else searching for Georgetown and matches me up with a random person. Of course it’s a guy, and he immediately disconnects. Omegle starts looking for another common interest match, but fails again. And again. I’m not too worried because it’s still early.
A few dozen random matches and disconnects later, it’s roughly 9:15 and finally the moment I had been waiting for arrives. Omegle tells me it’s found someone with the common interest of ‘Georgetown’, and I see the chat open. For a split second, there’s a moment of doubt as the other chat window remains black, but then the video appears and Emily is there in her typical setup on her bed. I’m so excited to see her, and I immediately wave to her before raising my screen to show my face on camera. I can see I have a big smile as I couldn’t help but show my excitement.
Emily also had her camera positioned as to not show her face, but as soon as I raised mine she followed suit by showing her face as well. She looks adorable and unbelievably sexy sitting on her bed.
“hi”, I start the conversation off simply.
“hi :)” she responds with a real smile in addition to her text-based one.
I apparently have no intention of being anything other than honest in this chat as next I type, “I’m pretty fucking nervous.”
“me too” she writes back which definitely comforts me.
It seems like she’s leaving it up to me to lead the conversation so I figure I’ll start in with some questions. “So how many times have you video chatted on here?”
“idk maybe 10 or 15?” She answers. And then adds, “but I stopped when you told me about the recordings.”
“yeah, sorry again for deciding to tell you that. I know it was super weird.”
“I’m glad you did.” She responded. “I thought about it more and it must’ve been really hard for you to do that.”
And this point we’re just typing back and forth, but it’s a little weird being able to see each other while doing so. I guess we could’ve turned our microphones on and just spoke to each other like if we were FaceTiming, but something about the typing seemed safer or more appropriate to me maybe? Either way, I was fine with this text-based method of communication we had settled on.
We continued to chat for quite awhile, the two of us just sitting there fully clothed on our beds. I kept asking her questions, basically anything that entered my mind, with no filter. The majority of my questions were sex related of course. I asked her if she was a virgin, and she was. And then after some follow up questions, I found out she hasn’t even kissed a guy before. She mentioned that she doesn’t go to parties, like most of the people in her grade do, so she’s never had a chance to hook up with a guy at one of these parties. She claims that no one ever asks anyone out at school, so she’s never been on a date either.
One thing that didn’t come up, and I’m kind of glad it didn’t, was anything about the specific video I had seen of her online. She didn’t bring it up and I didn’t want to have to come up with a cover story to both hide the fact that I went out of my way to identify her in the video, and also the fact that I had watched it all (repeatedly) when I had told her I hadn’t. So when she failed to even mention it, I certainly wasn’t going to bring it up myself.
I did share a fair amount about my history and how I used to be as inexperienced as she was in that I went off to college having never kissed a girl. I mentioned that I had always masturbated a ton though, and then she shared that she was the same way and that she “masturbates pretty much every night”.
Holy fuck, when she typed this it just blew my mind. Again, I’m so used to being in an asexual relationship, that the idea of a female wanting to orgasm every single day is just literally unbelievable. Personally, I’m horny enough that I could easily maintain a routine of jerking off every night if I was so inclined, but if I was in a relationship where my partner also felt the urge to orgasm daily, then holy shit what a dream come true that would be. I would be in heaven being able to have sex, or have other sexual activity on a daily basis. So when I heard Emily claim this, I was just in disbelief.
“No way!” I typed. “Every night????”
“Yeah, the nights when I wasn’t video chatting I would still lie in bed and give myself an orgasm before falling asleep.” Emily explained.
“How do you masturbate?” I needed to know.
“I usually just lie on my stomach and use my fingers on my clitoris.” She describes to me. This whole scene is pretty surreal as I immediately contemplate how she might just show me this in a few minutes if I’m lucky.
“Do you ever use objects inside you?” I continue with my questioning.
“Not really. I’ve tried but they didn’t feel good.”
“What did you use?” I ask.
She paused to think before typing, “handle of my brush, markers, electric toothbrush.”
“Oh, like a vibrator? Did you turn the toothbrush on when you used it?”
“Yeah, but I didn’t like that at all.” She answered.
This conversation was turning me on so much I had to constantly shift my position to give my rock hard cock room in my shorts. Eventually, I felt like it was a good time to take the chat to the next step so I asked, “should we get naked?”
As soon as I typed that, Emily didn’t even bother to type a response back. Instead she tilted her camera up even more, before standing up on the bed in full view. She first lifted up the shirt she was wearing to reveal she wasn’t wearing a bra, as well as unleash her gorgeous, bouncy tits. And then in one quick motion she pulled her shorts and I assume also her panties down, and tossed them aside. She was now standing there on her bed completely naked and I could see everything from her legs up to her face. She had such a stunning youthful and innocent look to her, it was incredible.
I typed, “Wow! You are GORGEOUS!”
When she saw I had typed something, she sat back down so she could see the screen better and also adjusted the camera to show her in the sitting position.
“thanks :)” she wrote back.
“How much do you weigh?” I continued with my never ending stream of questions.
“idk. 115?” She answered.
“You’re literally the sexiest thing I’ve ever seen.” I continued with my praise, and to be honest that was a completely true statement.
“isn’t it your turn?” She wrote next, redirecting the conversation.
“Ha. You actually want to see this old man naked?” I joked.
“I do!” She encouraged me.
So with that I lifted my t-shirt over my head and threw it off the bed. I then slid my legs to the side and took my shorts and boxers off. I turned back towards the computer and sat with my legs crossed and my fully erect penis pointing straight up. After getting back in position, Emily gave me a couple of claps to show her approval. She didn’t ask, but next I sat up on my knees and moved my pointed cock to be right in front of the webcam on my laptop so it took up basically the whole view in my video. I left it there for a few seconds and she wrote, “nice penis!”
“Thanks. It’s not much but I have a lot of fun with it :)” I wrote in response. “Do you think I could see a closeup of your pussy?”
“of course” Emily responded. And next, she laid back and spread her legs open and lifted her laptop onto the bed with her. It took her a second or two to get the position right, but soon enough she had it where the view was entirely on her spread-eagled vagina. It looked magnificent and I couldn’t help jerking my cock while I inspected it.
She had such big luscious labia lips. It was the kind of pussy where if she was just standing there facing you, her lips would be spilling out of her folds and exposed from any angle. But when she was spread open, underneath those protective folds was the pinkest most petite opening I can ever remember seeing. It was safe to say this view far exceeded anything I had gotten in the first two videos I had found of her online.
I could see her soft brown pubic hair on top, but her lips and creases where her thighs met her pubic region appeared to be as smooth as can be. After admiring the view for a minute, I typed, “it looks soooooo good. I wish I could lick it!”
Once she realized I had typed something, she set her computer back down on her bed and responded, “me too”
“god I could cum right now” I let her know.
“me too” she responded identically to her previous comment. Then she added “should we orgasm together?”
“I would love that.” And then I suggested, “do you think you could do it while looking at me?”
“yeah I think so” she said. Then she set her computer to be the right angle and spread her legs open. It reminded me of the first video I saw of her, except in this case she never leaned back onto the bed. She kept rubbing her pussy and staring straight ahead and soon enough I felt myself getting close so I typed with one hand, “gonna cum”
She saw that and yet again wrote, “me too”
When I saw that, it put me over the edge and I start exploding all over my bare chest. I keep furiously pumping my cock to get every last drop out, and I end up cumming so much that it leaves a large pool of semen sitting on my stomach and even filling my belly button. I can’t really tell from the video, but apparently Emily starts cumming right after seeing me orgasm. I come down off of my own high and lean forward trying not to let my collection of cum spill onto the bed, and I type “wow”.
Emily then types, “that was soooo hot. Seeing you come made me come”
Oh my god, what a thrill that just was. I probably would’ve liked the whole ordeal to last longer and have drawn in out some more, but I was just hopeless to stop myself from cumming.
“that was sooooo good” I type.
We end up chit chatting for a few minutes, still both sitting there completely naked, when she asks, “can we do this again sometime?”
Fuck yeah I think. But I tone it down slightly and write instead, “definitely”. I check the schedule on my phone and see that Amy will be out for work next Wednesday night, so I ask, “how’s next wed?”
Emily responds, “good. 9pm?”
“I can’t wait”, I write back. We then say our goodbyes and disconnect.
Over the next week at school, I barely see Emily at all. I’ve decided that our only correspondence should be through Omegle and as long as we setup our next chat on our current chat, there shouldn’t be a problem. She seems content with this idea too as she doesn’t attempt to reach out to me through any other means.
The next video chat date comes and it’s even better than the first. We again chat for a little bit before getting down to business. Having time to think even more about what I wanted her to do, in this second chat I made sure to have her spread her asshole for me, which I found to be so fucking hot. Her asshole is as virgin as can be as she explained that while she’s experimented with objects in her pussy a number of times before, she had never tried putting anything in her butt. I didn’t try to persuade her to experiment in front of me, so for now I was content just viewing her glorious asshole and imaging how good it must smell and taste.
We kept video chatting over the next few weeks, with roughly one meeting per week. I found our time chatting while clothed to be just as thrilling as the time spent naked in front of the camera. It was clear I was connecting more and more with Emily and starting to become totally infatuated with her.
Then one night at home, Amy let me know that she was going to have to travel for work and she’d be gone for three nights the following week. She normally would travel a few times a year so this wasn’t out of the ordinary, but as soon as she said that, only one thing crossed my mind. Should I invite Emily over when she’s gone? Could I do this? Or is this a terrible, terrible, idea?
Video chatting with Emily had been amazing, but if I had the chance to touch her, taste her, and explore her virgin body in person, I might just lose my mind with pleasure. God I would love a chance to be that close to her and not have to admire her beauty through a tiny pixelated window. Again, if there was any internal debate about whether I should take this next step or not, my biological urges bulldozed any rational fears or moral qualms I may have had and made up my mind for me. That question about whether I could do that to Amy? It apparently took about two seconds to decide I could.
A couple nights later, we had a prearranged chat date planned and as soon as we logged on, I brought it up.
“so I have something big to ask. And it’s totally fine if you don’t want to do it.” I start off with.
“ok. what is it?” Emily asks.
“My wife is going to be out of town next week for a few nights. Is there any chance you would want to come over?” I hit send on that message and wait. I can see her eyes reading it and then she breaks out into a big smile.
“Sure!” is all she types.
Holy fuck I think. I type, “oh wow. Ok! I think it would be amazing.”
“yeah it would!” She agrees. Then she adds, “would we have sex?”
I’m so overwhelmed here but I want to make it clear anything at all would be fine with me. “we could do whatever you wanted. No pressure at all. Promise.”
“ok that sounds good.” She writes back.
We ended up going over a few details in preparation. We pick the middle evening of the three that Amy will be gone. I give her my address, but we agree she should park a block away and walk over where I’ll be waiting to let her in. I ask that she not wear any perfume because I think it could linger after she’s gone? She says she never does anyway. Overall I’m just so nervous and excited I’m basically like a child. In hindsight it’s pretty pathetic, but I guess that’s just who I am.
I lost my virginity when I was 22, and it was to a girl who had plenty of experience. So not only have I never been with a virgin before, but of all the girls I have been with in my life, every single one had more sexual experience than I did, including my wife. There’s no doubt that I found the idea of Emily being a virgin to be very appealing. The fact that I would get to teach someone about sex was hugely exciting. Even the video chatting that Emily and I had done was something new to me, but something she was well familiar with. But real actual sex? I obviously knew more than Emily did about that one, and I was going to get to be the teacher for once. And as far as students go, I couldn’t possibly imagine a more willing or eager student than this beautifully perverted and horny young woman I was about to enjoy.
Leading up to this enormous night, I had a few details I wanted to take care of. I wanted to see if our son could stay over at my in-laws house, so I planted the idea in his head that he should have a sleepover. Sure enough, he started asking to stay at his grandparents and I was able to set that up for that particular night. That meant I was going to have the house entirely to myself.
Emily made it seem like it would be no big deal to get out of her house for a few hours as she often does to do school work. She thought she could come over from like 7 to 11pm without raising any suspicion, so we planned on that.
The big night arrives and I start getting ready. Of course I shower and shave and I think I brushed my teeth for like 5 minutes straight. I prep our bedroom and make sure to close all the shades so there’s no chance someone could spot something from outside. Overall I’m pretty paranoid but also so fucking excited. I purposefully haven’t cum in four days, which is an unusually long time for me to withhold myself, so I am bursting at the seams.
As it gets closer to seven, I setup by my front window, which gives me a view down our street. I want to make sure I can spot Emily coming and let her in discreetly with no delay, just to absolutely minimize the time she’s out front of the house. On the off chance that someone were to spot her, she’ll be carrying a USB drive that she’s going to pretend to drop off at my house with some application files. Yeah, I’m fucking paranoid to come up with all these ridiculous contingency plans, I know.
At 7:02, the moment arrives. I see Emily causally walking down the block towards my door. I can tell she’s taking a second to look at each house number to make sure she walks up to the right one. Soon enough she gets to ours and starts walking up the driveway. When she gets to the porch, I’m there to open the door and I let her in without delay. I close the door behind her and exhale.
“I can’t believe you’re here.” I say with a ton of nerves shaking my whole body.
“Yep, here I am.” She says with a big smile.
Hearing her talk and seeing her inches in front of me is such a huge thrill. I’ve never felt more excited, turned on, or alive in my life.
“Do you mind if we go upstairs? I feel a little exposed down here with the windows and everything.” I ask her.
“Yeah, no problem.” She responds.
Our stairway is just down the hall from our front door so I motion in that direction and she leads the way. She starts heading up the stairs and I’m a few feet behind her. Emily is wearing jeans and a simple long sleeve top, so nothing too revealing. As she heads up the stairs though I get an upfront view of her ass as I’m right behind and below her as we go up. I make no attempt to hide my gawking and I’m just in love with the shape of her lower body. Her legs again are so skinny and she has this wonderful thigh gap that leads all the way to her pussy. As I’m watching her ass climb the stairs, I keep thinking that I can’t wait to see that same view but when she’s totally naked.
We get to the top of the stairs and I lead her to our bedroom. The lights are on and the shades are drawn so it’s totally private. I ask her if she’d like a glass of water or anything else and she says she’s good. We stand across from each other maybe twelve inches apart and all I can say is “wow”.
Emily just smiles sheepishly and looks totally comfortable with everything, as she doesn’t appear nearly as nervous as I am.
After a short silent pause, I say, “I really want to kiss you.”
And when I say that, Emily leans in amd clearly gives me the go ahead. So I move in, close my eyes, and meet her mouth with mine. As soon as we touch lips, I feel her mouth separate mine and she instantly goes in with quite a bit of tongue. This catches me by surprise but I just kind of go with it. As we kiss a little more, it’s clear that she is going all out with the tongue. Her mouth is completely open and her tongue is basically exploring every part of my mouth.
While I’m not used to kissing like this by any means, and I initially thought it was strange, I quickly remember that she said she’d never kissed anyone before. And then I remember how I probably kissed the very first time and that I’m sure I used way too much tongue too. This just reinforced the idea that she was totally innocent and just figuring all of this out for the very first time. That turned me on even more.
I took her crazy tongue action and I ran with it. I started meeting her tongue with mine and then eventually returned the favor by pushing mine into her mouth as well. We kept at this for a couple minutes as I held her head with my hand. It was awesome making out like this and something I hadn’t done in decades.
Eventually I pull back and give her a big smile, and she smiles right back. I then ask, “Can I undress you?”
Emily doesn’t say anything but simply nods her head to give me permission. With that, I crouch down and move my head to be level with the top of her jeans. I unbutton the top and slowly unzip her fly. From there I take my hands and slide them inside the waistband and start bringing them down. As I get the jeans to her thighs, I can now see her underwear. She’s wearing basic plain white panties but I can clearly see her pubic hair showing their color through them. My face is inches away from her underwear as well and I have no problem getting the first whiff of her pussy. It smells so good.
I continue pulling her jeans all the way down until she’s able to step out of them and they’re totally off. At this point, I figure I could stand up and start taking off her shirt, but instead I just can’t resist and I slide my fingers into the waistband of her underwear and start sliding them down. As soon as I slide them down a few inches, I get my first up close view of her vagina and it’s gorgeous. Her big meaty lips look so suckable and I’m ecstatic at the prospect of getting to eat her out shortly. I finish sliding her panties all the way off and then I move my face into her crouch and take a huge whiff. Her pussy smells so strong and so good. I absolutely love it.
“Ooooh you smell so good.” I tell her.
As I say this she kind of pulls on my armpits a little as if to suggest I stand up. She’s standing in front of me with a shirt on but naked from the waist down. We start kissing again and after a few seconds, I begin to lift her shirt up. It comes up and over her head easily and now she’s left standing in just her bra. It’s a simple black bra but I already can see how great her tits are. I take a second and use both my hands to cup each of her breasts while still in the bra. I then decide it’s time to finish the deal and I reach around, and after a second or two to find it, I unhook the latch and let her bra come free. It falls forward off her boobs and finally she’s totally naked standing right in front of me.
There’s something extra hot about the fact that she’s now totally nude while I still have all my clothes on. We start kissing again as I use my hands to caress her beautiful naked tits. After a minute of this I move my hands and reach down to her bare ass and squeeze her ass cheeks a little. Ooooh this feels so good and the only downside is my cock is so hard it’s uncomfortable being constrained in my own jeans. So I finally relent and take a step back and start to undress myself.
I take my shirt off, followed by my jeans and boxers all in one motion. And soon enough I’m now standing there just as naked as she is. My penis is hard as can be and is sticking straight out at her. It’s impossible to miss, so Emily notices it and asks, “Can I touch it?”
“Of course.” I respond. Emily reaches forward and places her hand around the shaft and just kind of holds it there. As she does that I close my eyes and tell her it feels so good. After a few seconds, she starts very subtly just moving her hand up and down the shaft giving a very slight jerking motion.
“Does that feel good?” She asks.
“Definitely.” I let her know.
A minute later, I put my hand on her arm to let her know she can take a break, and I lead her over to the bed. I kind of motion to the bed and she climbs up on it, and then turns and sits facing me. I now have this beautiful 18-year old young woman sitting completely naked on my own bed in front me. The possibilities to choose from what to do next were endless and all equally enticing.
I start by just running my hands all over her body. I start by giving her hips a gentle pull so she’s a little closer to the side of the bed as I stand next to it. I run both my hands up and down each of her thighs. I can’t help but notice her skin is absolutely flawless. Her entire body is covered by such smooth, soft, and pale skin. There’s such a consistent look and feel about it that I couldn’t find a single blemish, wrinkle, stretch mark or any other imperfection anywhere on her body. I run my two hands up one of her thighs towards her pussy and it’s just remarkable how thin her thighs are. My two hands can practically circle her entire leg at its thickest part, and I don’t have particularly large hands.
When my hands reach her crotch, I start gently using the side of my four fingers to run against her wonderful protruding labia. As I do this, not only do I start to feel the wetness coming from her pussy, but I can see the glean of her juice being transferred from her vagina to my hand. After just a minute of rubbing, I pull my hand towards my face so I can take a breath and enjoy her wonderful smell that has coated the side of my hand now.
“Is it ok?” Emily asks nervously. In fact, overall she seems quite timid and on edge with the whole ordeal, so I adjust to try and make her feel as comfortable as possible.
“Oh it’s perfect. You’re perfect.” I quietly respond. And then I ask, “Are you doing ok?”
“Yeah. Just nervous.” She answers.
“I am too. Remember though, if you ever want to stop, just let me know and I’ll stop immediately.”
“I know.” She confirms.
After that exchange, I move back in with my hands and I use them to gently spread her two legs apart and pin them down towards the bed. She’s now completely spread open for me and I have the best view imaginable of her vagina. I had left the bedroom lights on on purpose, as I figured if she was fine with it, then I would love being able to see and inspect her as best I could. And boy was the view amazing at this point.
Her vaginal opening was the pinkest I could ever remember seeing, it almost didn’t look real. Inside it though, I could clearly see a white webby coating that was her own natural secretions and lubrications making their way out of her vaginal tunnel.
On top, she had her beautifully natural mound of light brown pubic hair. It was all neatly constrained to one section, rather than being an unkept bush that spreads everywhere like you may sometimes see in porn with hairy girls. I take my fingers and I kind of run the through the pubes, and I’m immediately caught off guard by how long the hairs are. Being in kind of a mat, I couldn’t tell just by looking, but when I ran my fingers through and uncurled the hairs, it was clear they were two or even three inches long. But when I would let them go, they would return to their preformed shape on her mound. Like pretty much everything else about her, I found this very sexy. I’m guessing she’s never shaved or even trimmed her pubic hair before like most women do, and I just loved this innocence about her.
After inspecting pretty much every detail about her pussy, I figured it was time to finally taste it. “Is it ok if I lick you?” I ask.
“Ok.” She responds, while still appearing nervous.
I can’t resist any longer so I move my face in and use my tongue to softly give one giant lick from her taint all the way up to her bush. I immediately notice she has a strong taste to her and it’s amazing. After having tasted only a single pussy for more than a decade, it was very obvious to me that Emily’s vagina had a completely different flavor to it. I went in for one slow lick after another trying to scoop as much of her flavor from inside her canal as I could. After I was satisfied with the amount of female cum I had consumed, I moved my mouth up to her clit and started focusing on that. I used soft slow circles on her clit to try and build up a little rhythm that might help her orgasm.
I’ve always loved licking pussy and I’d like to think it’s something I’m decent at. Between my wife and the few girlfriends I had before Amy, I never had a problem making women cum with my mouth. But after a few minutes of focusing of Emily’s clitoris, I notice there seems to be a lack of enjoyment on her part. Wanting to make sure that she’s still ok, I finally pop my head up, look at her, and ask “Is this ok?”
Emily admits, “I think I liked the part where you were touching me and just looking at me better.”
I instantly apologize and remove my head from her crotch. “Oh that’s no problem. I’m so sorry.” I say.
“Oh you didn’t do anything wrong.” She reassures me.
“Ok.” I respond as I now climb up on the bed beside her, while she’s still laying on her back. I softy run my hands up over her legs, across her hips, around her belly, and gently circle her breasts. “Is this ok?” I ask.
“Definitely.” She confirms.
So I keep using both my hands to touch her entire body while she’s lying face up. While there’s no doubt Emily is quite skinny, she does have the cutest pouch of belly fat that I can’t help but run my hands over. Her whole body is so soft from the skin to her body composition. Again, she’s not athletic in the least, so she has very little muscle tone, but I still found the combination of being skinny and soft to be yet another huge turn on due to its innocence.
After rubbing my hands all over her hips and stomach, I move them up and start fully caressing her boobs. They’re so big and soft they’re truly wonderful. She has quite large areolas that become nice and erect as I continue to run my hands over her. In fact, I use my fingers to feel the texture of the tiny bumps on her nipples, and it’s so sexy. Her tits are big enough that while she lays on her back, they kind of fall off to each side of her chest. And while they’re like this, it feels so good to take my two hands and grab the sides of each and sort of pull them back towards the middle where they can be together and make some wonderful cleavage.
After feeling them in person, I realize her tits are even bigger than I was giving them credit for. So while she’s lying on the bed, I ask Emily, “What size bra do you wear?”
“You mean like the letter?” She responds.
“Yeah, like are you a C or a D?”
“My bra is a D” She answers.
“Oh wow. That’s so sexy. Do you think they might still be growing?” I ask.
“Yeah maybe. I used to wear C bras until a few months ago when they started feeling too small.”
Holy fuck, that’s so sexy I think to myself. Now after all this time enjoying Emily’s perfect chest, I contemplate what to do next. I figure if she seems to actually like this way I’m examining her, then who am I to argue, because I absolutely love doing it too. So I take my hands away for a second and kind of motion to her and ask, “Do you think you could get up on all fours?”
“Ok.” she confirms yet again with the simplest of permission. With this she sits up at the waist and then spins herself around so she’s now kneeling on the bed while holding her head up with her arms. Seeing her in this doggy-style position is so fucking sexy. Her back is horizontal with the bed and I start by running my hand up her thighs, over her ass, and around on her back. It’s not just her legs that are notably skinny, as I take my hand and run it over her shoulder and down her arm holding herself up, and I can’t help but notice I can almost fit my hand all the way around the circumference of her upper arm. She’s so lanky and soft it’s unlike any body I’ve ever seen, let alone touched.
I then move my hands to her underneath side and I cup her wonderful boobs that are hanging down like udders. They’re big enough that I can see them stretching down under the pull from their own weight. I then take turns lifting each one up and pressing it against her chest to feel how heavy they are. Next, I run my hand over the soft pudge of her belly that is also hanging down due to the gravity of her position. All of her softness is so damn sexy, I love it.
Finally, I start rubbing my hands around on her ass cheeks. Her ass is definitely on the flat side, but that doesn’t mean it’s not heavenly. I position myself to be a little more behind her so I can get a better view of her ass, but I notice that how high she is on the bed is inhibiting the view a little. So I gently put my hand on her upper back and ask, “Do you think you could lower your chest onto the bed while keeping your legs up?”
Emily doesn’t say anything but she does as I asked. She kind of scoots her knees in a little bit in the process and now her ass is riding high in the air, completely exposed.
“Oh that’s perfect.” I let her know.
I move directly behind her on the bed and now her ass, asshole, and pussy are all spread wide open. It is the single most perfectly erotic sight I have ever seen in my life. Her virgin pussy has a nice visible gape, while her equally virgin asshole looks as tight as an asshole could possibly be. I take a second to just admire the view before I start running my fingers slowly over every sensual part of her that’s exposed.
I use my hands to caress her ass cheeks in a nice circular motion, while every so often running my fingers up or down her ass crack. I make sure I’m just barely making contact as I run them over her asshole. I try to gauge for any reaction from Emily but she’s totally silent with her face on the bed. After a few minutes of exploring every inch of her with my hands, I can’t help but move my face closer to her ass. After seeing how licking her pussy went, I knew there was no way I could attempt to lick her asshole, but I still could get close enough to experience it.
I move my face to be about an inch away from her butthole before taking a huge inhale through my nose. It smells like a combination of pussy and sweat, with to be honest the slightest hint of shit, but I love it. It makes me feel so dirty and alive that I’m not the slightest bit grossed out. If I could’ve, I would’ve given anything to be able to devour her asshole with my tongue. But I was able to restrain myself and eventually move back away from her ass. I then mention that she could turn back over and lay on her back again, and that’s what she did.
After she turned over, I was about to ask Emily how she was doing, but before I could say anything, she actually spoke up. “Do you want to have sex?” She asked me out of the blue.
I had already decided that as nervous and reserved as Emily had seemed thus far, I wasn’t going to push things to go much further than they already had. I had accepted that I would be content with at best some mutual masturbation, and just getting to experience touching her beautiful body. But when she asked me this, I immediately had to reconsider.
The first thought that entered my mind was, why would she want to have sex when she’s seemed borderline uncomfortable this entire time? Is it possible she’s actually enjoying this a lot but it’s not coming across? Or maybe she doesn’t want to have sex, but she’s doing it just to please me? And then I thought, maybe she’s made up her mind that she really wants to lose her virginity tonight and she wants to just do it and get it over with?
No matter what her thinking was, I needed to try and make sure she was ok with this. “Are you sure? We definitely don’t have to. I really mean that.” I try to stress to her.
“No, I want to have sex.” She assures me with more confidence than she had spoken with most of the night. “It’s actually the one thing I was looking forward to most.”
When she says that, it makes me think it was the last of those possible options I had laid out in my head. “You’re absolutely 100% sure?” I reiterate.
“One hundred percent. I promise.” She says.
I think to myself, she claims she really really wants to, and holy shit it would be amazing to fuck her, so I might as well? I decide that despite my earlier reservations, I guess it’s ok after all.
“Ok.” I say. “Again if you want to stop, just say the word.”
“Ok, I will.” Emily confirms.
I use my hands to gently position her hips right in front of me on the bed. She’s lying on her back and I’m on my knees in position to give missionary a shot. After getting her legs spread open, I use a finger and probe inside her vagina to sort of feel around and perhaps loosen it up slightly. The inside of her pussy feels amazing. It’s super lubricated and feels reasonable that I’d be able to fit in. I don’t have a large penis by any means, so I’m not too worried, but I take a moment to use two fingers on her first. Once I’m able to get those comfortably inside her, I figure it’s time to give it a shot.
I want it to slide in as easily as possible so I discretely spit into the cup of my hand and use it to wet the head and shaft of my penis. After that I lean forward onto my hands so my face is just above hers and I ask, “Are you ready?”
“I am.” She responds.
And with that I switch to holding myself up with one arm and use the other hand to guide my cock into her virgin pussy. The rock hard erection I had, combined with the wetness on both her and me, leads my cock to slide in surprisingly easily. One slow motion and it’s all the way in.
The warm feeling of her wet, tight, pussy surrounding my cock is just pure heaven. I close my eyes for a split second and just enjoy the comforting thrill. But then I realize I have to check on her so I open them back up to look at Emily. She seems ok, but has an intense and concentrated look on her face as one would expect. I ask, “How does that feel?”
“It feels good.” She responds affirmatively and somewhat believably. “You can keep going.”
So I switch to holding myself up with both of my arms and I start a slow in-and-out rhythm. Each thrust takes me all the way out to where I can feel the cold air of the room before plunging back into the warm, wet, heaven inside of her. There’s so much wetness all around that the repeated thrustings make a glorious slurping sound too. I keep doing this for a minute our two, enjoying every single time I leave and enter her body.
Eventually I figure it’s time to try somewhat of a different position. I pull out of her and then reposition Emily’s legs so they’re more pressed against her body instead of spread apart and open. This kind of naturally tilts her back a little but still leaves her pussy accessible. I raise myself up and use my hands on her legs now to support myself. This gives me more of an elevated position in relation to her and once I get settled, I’m able to slide my cock back into her pussy without any problem.
As soon as I reenter her though, a thought crosses my mind. At no point did either she or I bring up the question of using a condom. For me, I kind of take birth control for granted because I’ve had a vasectomy. Shortly after our son was born, Amy and I came to the decision that one kid was enough, so I went off and got snipped. Emily doesn’t know this though, and the topic never came up in any of our chats. So as I’m now directly above her with my penis deep inside her, I realize that she must have such complete trust in me that she didn’t even mention the idea of condoms. Although, then I realize that maybe despite her not being sexual active, she might be on the pill and that’s why she wasn’t concerned? I wasn’t sure what the reason was, but realizing that we were having unprotected sex without even discussing condoms was yet another turn on for me.
With this thought on my mind, I looked down as this beautiful teenager beneath me. Her flawless skin, her huge tits, and a nervous if slightly more comfortable look on her face. Even though it made no sense logically, I started thinking about the idea of impregnating her. I had seen “breading” type porn online before, but it never made much sense to me. Who fantasizes about getting someone pregnant? Isn’t that just a buzzkill? But here I was looking at Emily and her tiny thin arms and legs with her cute little pudge on her belly and I couldn’t help but picture her as the cutest pregnant teen. With each thrust straight down into her pussy, the fantasy just got hotter and hotter.
I realize what is happening and I look down at Emily and say, “I think I’m gonna cum.”
“Ok.” She says yet again, almost like a broken record.
I close my eyes, realize that I’m actually fucking a high school senior, and an adorable one at that, and I just fucking unload inside her pussy. While I’m doing it, in my mind I’m envisioning every squirt is going straight through her cervix and right into her young, fertile, womb. I cum so much that the subsequent squirts seem to never end. Just when I think I’m done, I get yet another shiver through my body and push one last bit of my spermless semen into her vagina.
Finally, once I’m sure I’m done, I open my eyes up and look at Emily face to face. I lean down and give her a kiss and it’s a soft sweet kiss with no tongue. I ask her how she’s doing and she says she’s great.
I realize her pussy is probably filled with so much cum now that I don’t want to make a huge mess, either on her or on the bed. So as I pull out, I hold her legs back so she remains tilted back with her vagina pointing straight up. I ask her to stay put for just a second as I reach over to the bedside table and grab roughly a million tissues. Once I have this huge wad of tissues in hand, I place it right below her pussy and then tilt her back down. All the cum, both hers and mine, comes flowing out and gets soaked up by the enormous clump in my hand. I’m able to fold it over though and then give her vagina a second clean wipe to where I think she’s in pretty good shape. After that, I toss the disposable cum rag onto the floor and lie down next to Emily.
“Thank you.” She says to me as soon as my head is next to hers.
“Oh, no problem. I didn’t want you to have that mess all over you.” I said.
“No, I meant for having sex. Thanks for having sex with me.” She clarified.
“Are you serious?” I say quietly. “Having sex with you was literally a dream come true. I should be the one thanking you.”
“Ok, well that’s nice of you to say.” She then said. “I’m sorry if I didn’t seem like I was enjoying it, it was just a lot to process and kind of overwhelming.”
“I totally get that.” I responded. “I feel bad that you didn’t orgasm though. Would you like me to touch you a little bit?”
“Oh I’m good.” She answered. “You don’t need to do that.”
We laid there for a few minutes not saying much, when I then mentioned, “It’s too bad you can’t spend the night here. Under different circumstances that would be pretty nice.”
“Yeah, I know.” She agreed. But then she said, “I probably should get going before it gets too late so my parents don’t start wondering where I am.”
I look over at the clock in our room and it’s only 8:20, but I’m not about to point out that it’s actually not that late.
“Ok.” I said. And then I asked, “Do you think we could do one of our video chats next week?”
“Yeah, definitely.” She responded.
I checked my schedule and we agreed next Tuesday would work, 9pm as usual. She was about to get up when I mentioned, “This is weird, but my wife always pees after sex. She says it helps prevent against getting a UTI, so maybe that’s something you’re supposed to do?”
“Oh, ok. I can do that.” Emily says. And then she finally asks that question I was waiting for, “Was it bad that we didn’t use a condom?”
“I promise it’s fine.” I assure her. “I’m actually infertile as I’ve had a vasectomy, so there’s no possible way I could get you pregnant. Just out of curiosity though, are you on the pill?”
“No, I’ve never taken birth control before.” She admits. And when she said that it just confirmed how much she must trust me to have allowed me to blow that huge load up in her pussy without knowing anything about whether we were protected or not.
Anyway, after that brief exchange, Emily got off the bed, grabbed her clothes from the floor and took them into the bathroom. A few minutes and an audible flush later, and she emerged fully clothed. I quickly got dressed as well and we headed downstairs. I confirmed that she felt fine to drive home and then mentioned I can’t wait to chat with her next week. She agreed, we kissed goodbye with a fair amount of tongue, and then I escorted her out and watched as she walked back down the street towards where she had parked.
I sat down and exhaled, totally overwhelmed by what had just happened. My initial reaction was that it didn’t go that well, mainly because she seemed to not enjoy most of it? But the more I thought about it, the more I came to rationalize how it went down. I had to remember that this was not only her first time having sex, but her first time having any physical contact with another person whatsoever. Of course she was going to be totally overwhelmed. She kept saying she was fine and enjoyed it, so maybe I should just take her at her word? Going into it, knowing how sexually curious and even kinky she had shown herself to be, I was envisioning a night of lots of experimentation and multiple orgasms for both of us. But in the end, I came to realize that was totally unrealistic. Experiencing something as powerful as sex for the very first time is guaranteed to take someone out of their comfort zone, and there’s no way she’s going to get much enjoyment out of it if she’s clearly not comfortable. At least that’s what I concluded and tried to convince myself of.
Either way, I was looking forward to getting to chat with her some more and to see where our relationship might go from here. Obviously being able to meet in person a second time was far from guaranteed, but if it did happen I was optimistic things would get better and better.
The following Tuesday came around and I logged onto Omegle, keyword ‘Georgetown’. But something unexpected happened that night, that perhaps deep down my subconscious could’ve seen coming. Emily stood me up. She never logged on. I know because I was on basically from 9 all the way through until 11pm, just in case she was running late. I thought maybe there was a chance she got the day mixed up, so I logged in the following night at 9pm, but nothing then either.
At school, I was already keeping a low profile and now that I was worried she was upset at me, I stayed even more out of sight. I did see her once from afar, so I knew she was totally fine, at least not sick or hurt or something. But I couldn’t understand why she wanted to end things with me, which is how I was taking getting stood up to mean. I figured that if she wanted to talk to me, she knew how to, so I would leave it up to her.
With things between Emily and me apparently over, it led me to reevaluate the state of my marriage with Amy. When presented an opportunity, it was clear I had absolutely no qualms about cheating on her. And while it’s easy to say this was some sort of once-in-a-lifetime scenario, I don’t think that really mattered in the end, and it’s totally possible I would’ve cheated if given practically any opportunity. That didn’t make me feel good, but it motivated me to try to be better in our marriage and confront the issues we had with an open mind of hoping to find a better coexistence. It’s an ongoing process, so we’ll see how that goes.
About a month and a half went by, and with no contact from Emily of any kind, it was pretty clear that she wanted to move on. Even if I was curious as to what her reasoning was, I was willing to accept that. Then I heard the news that she got accepted to Georgetown, and I was delighted for her. I figured if I did see her now, it would be totally reasonable for me to congratulate her on that and then let her be. So because of that, I maybe ventured out a little more to see if I might spot her.
The next day I was in the hallway when I saw her. But that was far from the most notable part. I saw her walking past the cafeteria, but she was holding hands with a senior guy, as if they were clearly in a relationship. How interesting was that!
I’ll admit, I was a little bit jealous, but mostly I was just excited for her to have a boyfriend. In fact, I was ok enough with it that I even approached them as the two of them were walking towards me.
“Congrats on Georgetown!” I said to Emily with excitement.
“You heard? I know!” She answered back totally normally as any student would have in that situation. And then she said very sincerely and more quietly, “Thanks for all your help.”
“It was my pleasure. I’m so excited for you.”