I am not the sort of person to randomly meet people I’ve chatted with online. I’ve never gone to any of the Meetup gatherings I’ve bookmarked online and the few dates I had through sites or dating apps were either unremarkable or disastrous. For most of my adult life I had been in a couple of long term relationships that ended for the reasons relationships end, and I was in the worst sexual drought of my life. Years of neglect and denial. I was miserable. Keep reading. I promise it gets better. ;)
I moved to a small city in a new part of the country to take my first academic job. It’s been nice, but I work so much I rarely have the opportunity to meet new people and so my sex life was still non-existent. I bought a Fleshlight online on a whim. It felt surprisingly good, but mostly just made me long for the real thing again.
One night I installed an anonymous app that allows you to see posts made by others near your location. I replied to a few posts here and there, not expecting much more than to assauge my loneliness. I knew, though, that even if I did hit it off with someone, I’d likely not have the courage to meet them in person. They’d be dissappointed with my appearance. I’d be nervous and say something stupid. It wouldn’t be fun. I was certain it wouldn’t lead to anything.
One night in late November of last year I replied to a post made by someone about fifteen miles away. It said something like “Bored. Really wish someone would distract me.” I open a chat window and can see it was posted by an 18-20 year old woman. I am in my mid-30s, a gray-haired academic with a dad bod and a face that suggests I may have been handsome once, as a younger man, but am certainly nothing special. By my own estimation I am neither attractive nor unattractive, and my face bears the evidence of years of stress over grants, papers, deadlines, students, and failed relationships. There was no way this young woman, if she even was a woman (as opposed to a man impersonating one), would be interested in talking to a guy like me.
But to my surprise we hit it off. She was charming, smart, very funny, and said nice things about my pictures, though I suspected these comments were borne of pity and charity more than anything else. Soon the pictures we exchanged became more risque, and I could see that not only was her face devastatingly beautiful (with big, beautiful, glinting, almond-shaped eyes, a heart-melting, bright smile, pale, unblemished, perfect skin, and raven black hair so perfectly kept it looks like it couldn’t possibly be real), her body was to die for. The curve of her neck leading to delicate shoulders that framed the biggest, most impressive pair of round, white, natural DDD tits I’d ever seen. Her ass was sheer perfection: juicy, round, and big enough to create the perfect cushion for doggystyle pounding. An ass made to be worshiped. On top of all of this, she told me she was fairly short. I jerked off to her pictures many times, and continued talking to her, but strongly suspected “she” was a he who was catfishing me. After all, if it seems to good to be true, it usually is. She had previously told me she was married, though, and had shared some personal details that seemed too specific and real to be made up for the purposes of catfishing. I was getting to know her and I desperately wanted to believe she was real.
One Sunday afternoon I was lazing around at home doing some work when I started chatting with my new friend. I joked that I was having a hard time being productive because of how horny I was. “Well, if I were there, I’d definitely let you use my tits,” she told me. I pulled up the one of her pictures and started fantasizing about what her big, soft, perfect tits would feel like in my hands, my veiny dick pumping between them while she looked up at me smiling. I refocused. “Haha. I wish.” I said “And what would your husband think about that?” She replied “He wouldn’t have to know.”
At that moment, my pulse quicked and my cock instantly hardened. I felt a rush of euphoria course through my body, butterflies flitting about my chest. I asked if she was serious. And asked again. She asked for an address. I gave her the address of a nearby park and told her when I could be there. She replied with a description of her car and said “See you there.” My first thought was “I can’t go” for so many reasons. “For one, I am almost certainly going to be murdered,” went the first thought. “I’m going to end up on the news and the police will put together a story to tell my family, an embarrassing one about how I was dumb enough to fall for some catfishing guy who caved my head in with a crowbar in order to take my wallet.
Nervous as hell, I walked to the meeting spot and saw her van. And there she was, the ridiculously hot young thing from the pictures. I couldn’t believe it. I got in the passenger seat and introduced myself, unable to look her in the eye but also unable to take my eyes off of her. She had on black yoga pants and a tight top that showed off her impressive rack. We made some small talk and I suggested we move to the back, where one of the sets of seats had been removed and there was room for us both. Within moments I was sliding my hands along her thighs, feeling the heft of her big naturals in my hands, squeezing her ass lightly. I was keeping it together reasonably well, mostly repeatedly telling her how gorgeous she was and how surreal it was to touch her. She smiled sweetly and slid her hands down to the aching, stiff cock in my pants. She reached in and pulled it out, her silky hands sliding over the engorged head and soft foreskin as I let out a groan. She jerked it slowly, varying the pace of her stroke to match my moaning and looking at my face to see the effect of her diligent work. I continued to grope her 20 year-old body, completely overwhelmed and unable to put sentences together. At a certain point and without any clear idea what I intended to do, I slid her pants down halfway and admired her pussy in black, lacy panties. Not only did it look delicious and inviting, it smelled like heaven. I could tell she was dripping wet without even touching her. I contemplated sliding them off and having a taste (or more) but didn’t want her to feel pressured, given that we didn’t really talk about going that far. I restrained myself for the moment.
She leaned back and pulled her shirt off, her big round tits smooshed together and supported by a bra that had to contain titanium, I thought. She then proceeded to pop them out, one at a time, so they rested on her bra like a shelf, her nipples hardening before my eyes in the slight cold. Meanwhile, outside of the van, by the river adjacent, two young guys in their 20s were having a conversation. If they’d bothered to look they easily could have seen us and surmised what was going on. Now I was even more nervous but knew that if I didn’t stuff my big, rock hard dick between those perfect tits I would regret it for the rest of my life. She leaned back, squeezed a few thick globs of lube between her DDDs, and wrapped them around my cock. I have never felt such a perfect, enveloping, warm softness. Her big brown eyes looked up and she smiled as I started thrusting back and forth, my rock solid hardon sliding in and out of her cleavage. And with every thrust I watched the swollen, purple head come within inches of her soft pink lips. And with every pump I wanted more and more to just pull back and stuff it in her mouth, fucking her beautiful face the way I’ve never been allowed to by ex-girlfriends.
Not normally being the type to randomly hook up with people I don’t know, and obviously aware of how dangerous that can potentially be, I told myself I wouldn’t do more than let her jerk me and fuck her tits. The temptation was unbearable though, and thankfully her incredible tits worked their magic before I had time to make the inevitably reckless decision to just go for it and violate all of her tiny, juicy holes the first time I met her. When I signaled I couldn’t take it anymore she firmly gripped my shaft and milked me with long, vigorous strokes that made me know it was game over. I awkwardly and exasperatedly reached for my phone and asked if I could video the cumshot. “Sure!” she said. I hadn’t even pressed record when I lost it, thick ropes of cum blasting her neck and chest, one after another. “Two hands! Two hands!” I begged and she responded with a double fisted pump that completely drained my balls, about a cup of pearlescent jizz pooling in her cleavage. So. Much. Cum. All I could think was what it would look like leaking out of her.
I felt like I hadn’t shot that hard since I was a teenager. She looked down at the mess and we both laughed at how much there was. Just then all of the anxiety about us being half naked in a semi-public setting rushed back in. She pulled out a roll of paper towels and we both cleaned ourselves up. I thanked her profusely and, true to my age and slightly paternal disposition I gently warned her about meeting strange men (like me) alone, and how important it was that she be safe. I’m not even entirely sure what I said. It was completely overwhelming and stunning. We said our goodbyes and I walked on the air all the way back to my apartment.
A week later we met up again, driving to a parking lot, where she gave me the longest, most loving and sloppy head of my entire life before spreading her legs for me and telling me, without words, that she needed me to fuck her. To find out what happened, keep your eyes peeled for part II.
Source: reddit.com/r/gonewildstories/comments/alsr7n/the_20_yo_bombshell_and_the_dirty_older_professor
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I can’t wait? Will you post the cumshot?
Great story :) Cant wait to read part 2 :)
I’ve actually met up with some pretty horny women off of Whisper myself ?