I find the most amazing females on relatively anonymous dating sites and Reddit [MF]

First post here, and I’m an older guy who really is no Adonis whatsoever. I should foreshadow this….

I’m recently divorced, and recently recovered from a neurological condition which left me in a wheelchair for a while. That condition impacted my life, forcing me to learn to walk again and requires me (still) to stay in good shape and such. I’m in the gym 6 days a week. I’m not terribly old, but I’m not young either. There’s a good amount of grey peppered into my goatee these days and I suppose if I didn’t shave my head, the same would apply for the dome. I’ve got a few kids, left a nice big house to the ex which is almost paid off, there’s 1-2-3, 4 cars including mine in the driveway if I happen to be there, and a nice big ass backyard with a pool.

It’s probably no surprise *cough* Reddit *cough* that my background is in technology and I’ve spent the last decade and a half straddling between sales and engineering roles. I’ve been blessed and done fairly well for myself career-wise;well enough that I’m compensated more as a result of my experience and expertise versus how many hours I contribute to a task or a problem. You’re paying me a premium because I can save you the time you’re likely to sacrifice or already have sacrificed by throwing bodies and resources at things. If that doesn’t sound boring enough, or already gotten your panties sopping wet, I’ve also been the contributing editor on a bunch of technical books and I still get those opportunities here and there. Changing those sheets yet? So sometimes my workload is almost nonexistent, leaving me plenty of spare time. This is not absolute or always the case, but generally my work week is about 12 hours. That leaves me quite a bit of ‘free time’, more so now that my kids are older and I’m living elsewhere. If I absolutely needed to- I could *probably* get liquid for thirty or forty thousand dollars in a few hours. For me that’s absolutely an achievement and a benchmark in terms of where I’m at. I don’t “need” to work; I enjoy working and I enjoy mentoring those who trail behind me. Life certainly has changed from running around NYC 14 hours a day fixing desktop pc’s, living in a 6 story walkup studio apartment, and trying to figure out how to make rent this month.

I think it’s safe to say that whoever you are in life, I understand your struggle. Anecdotally, a few months back I started having some good banter with this amazingly descriptive and explorative 26 year old whom “oopsied” and unknowingly revealed her main Reddit account, which of course I spent time ‘reviewing’. Turned out she had lent a substantial amount of money to another redditor, like $900 , and been burned by that person. I anonymously pm’ed her offering to recoup her loss at an interest rate of half of what she had charged. She bit, paid me back in a month, and I sent her back the difference between the interest minus the fees imposed on me. It felt great. I felt like I may have even restored her faith in the ability to be randomly kind. I never mentioned this to her and she never discovered that this was me. I still do this occasionally in situations where I see a lender get burned on /r/borrow but it’s infrequent and I don’t advise anyone do this. The real takeaway here is this: Always be kind because you never know who you might actually be corresponding with, especially on a platform as pervasive as Reddit. Sometimes, those people have the ability to change your life.

Alright, let’s move on to why you actually clicked versus scrolling past. I have developed a higher than usual libido for a male my age. Subjective? I suppose but compared to many of my friends and other folks who I’ve had the opportunity to discuss this with, including my own doctor- I have a ‘very healthy’ sex drive. I’m going to say that I always have, but I’m not sure that’s true. I believe that following this recovery I’ve been through, that there has been some impact as a result- likely the result is a direct correlation to my diet, and the amount of exercise that I do but I’m not a doctor so don’t take my advice. And I’m guessing you’re asking yourself, “How exactly are you measuring this?”, to which I’ll respond as follows: If the opportunity presents itself, which it frequently does these days, I can manage to jerk off anywhere between 5 and 9 times in a 24 hour period, no alcohol or meds necessary. A micro dose of an edible doesn’t hurt but it’s hardly a requirement. Secondly- my refractory period is really brief, maybe anywhere from 45 seconds to a minute or so. Granted, if I have one particularly overwhelming orgasm it might be longer than that but on average it’s about a minute. Third – I tend to go through these periods of being insatiably horny, like when I was 17 or 18. Sometimes it’s a week or two; other times it’s ongoing for a couple months. There’s no rhyme or reason to it.

Several months ago I found myself diving into all the NSFW subs and just kind of lurked there for a while. Would I ever have the kind of balls to advertise my cock in photo format? Uh, nope. A video of me jerking off? Unlikely, albeit I’ve briefly considered it. Exchanging pictures for pictures? Still no. But what I did find most intriguing and drawing was the idea of some *actual* interaction between folks whether that be in person, video chat, kik, Skype, phone etc. I quickly went ahead and made a new alt account, joining every sub that included the word ‘dirty’ or ‘chat’ and a handful of others.

I’m going to estimate that I probably spent a good two weeks invested in answering and/or responding to any “F4M” chit chat offer or dirty pen pal request that struck me. I’d spend hours responding with all of my heart (sometimes with dick-in-hand). I was likely responding to 80% of the posts that even *vaguely* interested me, and following that two-ish week timeframe I did a little assessment- It turned out that many, no, most of my responses whether heartfelt or quick and dirty, simply went unanswered or ignored. Mind you, I did get a few results. There were a few ‘sellers’ who apparently expected that I was going to pay for their time to chat with me on Kik. No. There were the really quick, terse responses like, “you really have a way with words…”, to which I would respond and then get ignored. And there was a very short list of folks that I actually started talking to. So the 3% might actually get hot and heavy, often quickly enough and I remain in contact with about half of those chicks.

I also made a discovery- that 1.5 percent…. we really got and get along. It’s gone way beyond what I was seeking and it’s strange to say the least. We’d usually have some good banter going, texting or roleplay. In these circumstances, the chemistry was just right and it would often escalate into a voice conversation. On some occasions we would even exchange pics – I might send her a pic of the little droplets of precum on my cock or a photo of my hand wrapped around the shaft of my dick. Sometimes it was just the subtle outline of my cock in my gym shorts. But these particularly few individuals were special to me, and along the way I’d get to know them. I’d get to know a lot more than what made them moan, squeal, or whether or not they actually enjoyed sucking cock or not. I’d discover the things that might keep them up at night, or weighed them down emotionally. I’m no expert on the subject either but if I was taking a cross-section of these women, they shared some of the same attributes- they all enjoyed the attention I showed them but they weren’t desperate for it. They all pretty much fell between the ages of 25-37 (more on the 20-ish side though), they were fairly conservative on the exterior- nurses, government contractors, teachers and so forth.

I found myself going out of my way not to impress these women, but to extend my own experience regarding life *with* them. I helped rewrite some of their resumes or prepare for interviews as I have some excellent background in both resume writing and interviewing candidates. I’m finding myself at the post office mailing an old iPhone to Rebecca, or ordering some oddly specific ancillary item to Jessica. Samantha had expressed interest in making some additional income to help her finally pay down her student loans and shared with me her idea of selling her panties which of course I found kind of intoxicating and entrepreneurial at the same time. And she was onto something because she was incredibly shy, but incredibly photogenic and happened to get extremely wet and grooly when she was excited. So I helped her develop a plan, find a payment platform, develop an advertising ‘strategy’, find a great wholesale supplier of counterfeit VC panties, and launch using some of the porn sites you’re watching all the time. Six months later, she had a fairly steady residual income of ~$2000/month if she really had the wheels turning. It sounds like I’m bragging now, but remember, I’m after none of this. I wasn’t looking to make ‘Internet friends’. I wasn’t trying to build some Rolodex of good deeds, no more than I wasn’t trying to hear Jessica tell me how much she simply loved having her clit teased between the lips of a willing man. And how, in return what she really really loved was to quite literally suck your dick to the edge of orgasm, and then literally suck your hot load of cum out of you. Because she got off on the feeling of that load pulsing through your (my) cock and this would often send *her* over the edge. Her. Whoa.

I didn’t want any of that. What I really wanted was some fuck whore who had a brain between her ears, lived close enough that we could entertain the idea of having her sit on my face, and make it happen as regularly as I liked. Bonus points if she’s a brunette, a little chubby and wears glasses. You want to slurp my cum out of my dick, no problem. But my guests come first. Anyway, look, I’d completely failed to meet my initial objective and I’m veering off the course here.

I realized two things- Reddit was a great platform but there were a few others that I should explore, and two, women didn’t want a nice guy who happened to be literate and marginally successful. They said they wanted that, but not what they were typically looking for in the context of their posts. No, they wanted Shallow Raulo the biggest asshole in existence and the guy who disrespected, degraded, and lent them confirmation around their limited sense of worth. That. That is what they wanted, or at least what it seems they responded to. So go to hell with the 2500 word responses to your dirty pen pal post. I had completely wasted my time.

It took a lot to switch up my strategy, and swallow my better senses trading quick and dirty responses to which I drew attention more immediately and more abundantly than ever before. “Don’t even think of sending a dick pic”, which as you might imagine would be something I would never do. Welp, not anymore; I’m sending you a dick pic. A fresh one, maybe one with some jizz running down onto my balls. “One line responses are going to be ignored”, uh no they’re not. Because I figured out what you wanted to hear, and you responded again and again and again. Right Rachel? Matter of fact, Rachel lived less than two hours from me and two months later, when her ‘boyfriend broke up with her’, she came to my condo for three days. On day two, maybe 2 or 3 AM, we’re posted up at the condo complex pool a little tipsy and a lot high, and she’s straddling my face, whilst jerking me off all the while I’m signaling for her 25 year old ass to keep it down. That was a fun few days to say the least, evidenced by my cock being sore and almost painfully sensitive for the next three days. A few weeks ago I even started fucking the nanny who lives in my ex’s house. She didn’t work out long-term but I was surprised that it happened the 15-20 times it did.

What I realized was that I could get what I wanted, for the most part anyway. In fact I could even leverage my incremental improvement by piggybacking off my last experience. There were a couple of other Rachels, and they wanted to hear about the details… in detail. I guess that’s what you might call compounding your investment but it worked. Did it feel good? Initially. Over time? Not really. Two or three more after Rachel, one of whom I drove down to the Outer Banks in NC to join while she was house-sitting for a friend, a couple more who came to me for sleepovers, and one or three more who had me join them for lunch in my car. This equated to them giving me cautious head while I usually tried getting my hand down their pants or up their skirts. During the last encounter, on some rainy July afternoon in my car, while Jenny had quite dramatically teased my cock almost to exhaustion, I *finally* came, holding her ponytail in my left hand while my right had a death grip on her shoulder. My cock happy to unspool in her mouth as I let out a final, tremendously archaic groan, and then I relaxed, falling back against my cars seat. I actually remember how perfectly choreographed this one drop of rain was running down the windshield in unison. Then she starts to cry.

If I’m being accurate, it was more like a weep than an all out fit of crying, though there were tears. And there was the slightest bit of cum on the corner of her mouth. In another situation or setting I suppose this might be sexy or hot. But sitting here in my very expensive car, wearing flip flops, a worn out T-shirt and Old Navy cargo shorts, my cock out, and next to me this 27 year old girl who distinctly reminds everyone of Pam Beasley, is Susan. And Susan is crying. I remember feeling my dick almost retract inside me, and I felt fucking horrible. I’d no idea what I’d done (or didn’t do because I would have rather ate her pussy as originally discussed).

It’s really hard to offer solace in a situation such as this and the best thing I could manage was to ask, “what’s wrong”, with this huge smile on my face as I slid my boxers and shorts back up. It sounded insincere even to myself. It wasn’t meant to be, but it sounded that way. Uncomfortable, yes. Tremendously so. She sat there and cried for a good four or five minutes at which point I was saved by way of her phone buzzing. As things turned out, Suzy was working through some emotional issues that I’m not going to get into here. I left her that day at the entrance to her building, and I left feeling like not only the biggest loser ever, but like some sort of predator; an evil, selfish person. Since then, I decided to take a break. I really needed to understand things and back to Reddit I went with this story.

I just finished up an incredibly long and mundane project that was work-related so I’ve got some free time for the next foreseeable few weeks. Info is in my profile. I’m also finding some creative outlets again in /r/gonewildaudio so maybe you’ll hear from me on there. As I always say, the Reddit community has always been and remains special to me. There are great people here, kind and loving. Thanks to all of you for taking the time to allow me this opportunity again. Maybe I’ll hear from ya……..

Source: reddit.com/r/gonewildstories/comments/co1y6n/i_find_the_most_amazing_females_on_relatively