3 Mart 2024

How It Was Ch. 06

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Milf Squirt

This is a follow up to “How it Was” Ch.1-5 so it might make a bit more sense if you read those ones first, as it makes references to characters and situations in the earlier chapters, but I think you can stroke to it without that information.

This story is pure fiction written to explore sexual fantasies without the moral and ethical constraints of real life. It purposefully ignores real world consequences of unprotected sex with multiple random partners. In your non-fiction life, you should obviously take suitable precautions and treat people with respect.

CW: This story contains some depictions of rough sex.

If you are not legal age to read erotic fiction, please leave now and do not continue reading. For everyone else, I hope that you enjoy it and have fun. Constructive feedback is welcome.

All materials presented herein copyright the author.


Friday had finally arrived. I stood at the bus stop in front of my high school in the sultry evening air waiting for Mr. Walters to pick me up. In the gym bag next to me I had a change of clothes and a six pack of beer that I had bought from Trent, the college age dude who hung out at all the high school parties, selling alcohol and weed and pills. I usually didn’t go in for that kind of stuff, but this was going to be a special night and I wanted to be relaxed. Two empty Miller cans lay crumpled on the curb beside me, glinting faintly in the golden light.

Mr. Walters pulled up in a tan Mazda 626, the tape deck blaring AC/DC’s “Sink the Pink”. My normally stern biology teacher leaned over and popped the door open, smiling up at me, and I admired the way his arms and shoulders filled out the tight black t-shirt he was wearing. He looked me over as I slid into the passenger seat, his large hand running over my arm and down my leg.

“Looking sexy,” he said in his deep voice, and he waggled his eyebrows at me. I bit my lip and fluttered my eyelashes at him, my hand on his acid washed jeans.

“You too,” I replied, moving to cup his bulge. He pulled away from the bus stop with squealing tires and soon we were flying down the highway heading south. The sun was setting on my right and I watched the highway signs pass, thinking about my trip down this same road yesterday, and whether I should risk going down on Mr. Walters, since the traffic was so much heavier than the day before.

As I was coming to the decision that I should definitely risk it, I read a sign that said “Rest Stop — Closed”, and I briefly glimpsed what looked like headlights flashing behind the trees. The cruising spot that my gentleman friend had introduced me to yesterday morning seemed to be gearing up already. The thought sent a jolt through me and I let out a little whimper, shivering.

I looked over at Mr. Walters and he was looking back at me quizzically. I leaned closer to him, stroking his growing cock through his jeans.

“Have you ever gone cruising?” I asked him, slowly pulling down his fly. He cocked his head and shuffled in his seat to give me better access.

“You mean, like at the rest stop? How do you know about that?” I popped open his button and saw the base of his thick cock stuffed down the leg of his pants. He wasn’t wearing underwear and his pubic hair was neatly trimmed. A Ford Escort station wagon passed slowly on our left. I caught the eye of the driver, a tired looking middle aged man wearing wire-rimmed glasses. I leaned over into Mr. Walters’s lap, kissing the shaft of his cock as I gently worked to tug it free.

It flopped out, semi-hard and pulsing in my hand, the head half sheathed in a cowl of foreskin. Unable to resist, I took it between my lips and he let out a hiss of satisfaction, his member plumping in my mouth. I ran my tongue over it, drooling saliva, pushing gently at the hood, sucking the head, easing it to the back of my throat, then slipping the rim just past the seal of my lips and back in again. His breathing quickened and his hips pushed up into me, slowly fucking my wet mouth.

I came up for air, a string of spit running down my chin, and I glanced over to see our neighboring motorist still keeping pace, his head pivoting from the road ahead of him to the show in the next lane. I winked at him and began stroking Mr. Walters with a slightly exaggerated movement, wanting to be sure our voyeur knew what I was doing.

“Well, I happened to get a ride out there yesterday, had a pretty fun time too,” I finally replied. My hand played over Mr. Walters’s slick meat, jacking him with a backhand stroke, then slipping down and rolling his balls in my hand. I nuzzled into his neck, kissing his ear, eliciting a soft moan. “This older guy picked me up at Bean Around the World and we drove out here, I was busy sucking his fat cock so I didn’t notice where we were going. He parked in this gravel parking lot and he fucked me so good in the back of his Lincoln.”

Mr. Walters moaned louder as I went down on him again, trying to concentrate on steering the car over my bobbing head, his almanbahis hardness enveloped in my warm mouth. I sucked him smoothly, coating him with spit, charting the veiny surface of his shaft with my tongue, tasting his leaking pre-cum, savoring the throbbing flesh of his hot cock. Finally I pulled off him, saliva webbing my mouth and chin to the member I had just been worshipping.

“He wasn’t the only one that fucked me either,” I continued, “some random hiker showed up and watched us, then he took a turn after the first guy blew his load. It was so hot, I felt like such a slut. If there had been another ten guys I would have fucked them too.” My cock was painfully hard now and I wanted nothing more than for Mr. Walters to pull the car over and ravage me in the back seat, or bent over the trunk, or laying in the dirt at the side of the highway, I didn’t care as long as he fucked me hard.

“Billy,” he said sternly, turning his head to look directly in my eyes, “you have to be more careful. I know it’s exciting, strangers wanting you. It feels so freeing. At first. But listen to me,” he said holding up his hand to forestall my protest, “not everyone is going to be nice about it. Not everyone can be trusted. Didn’t you learn anything after that run-in with Wayne?” he turned back to look at the highway.

“How did you know about that?” I blurted. He looked at me from the corner of his eye and shook his head slightly, like he couldn’t believe how dumb I was.

“I live with Felicia,” he stated, as if that was supposed to mean something to me. Seeing my incomprehension he continued, “Ms. Jones, the school secretary? She came home the other day with Craig and Wayne and had a long talk with both of them.”

I was still trying to get my head around Mr. Walters and Ms. Jones living together. Were they roommates? A couple? Wasn’t he gay? I didn’t get it and I told him so.

“Look, we’re friends… and a bit more. We share rent, we make meals together and we fuck a few times a week. I love to fuck, Billy, you know what that’s like. It doesn’t much matter to me who it is, man or woman, I want both, I get different things from each.” He could see that I was still confused. “Are you telling me you never once did it with a girl? Jacked off thinking about Lucy Porter’s ass, or… Ms. Jones’s tits after seeing her in one of those blouses she wears? “

Lucy Porter had graduated last year and was widely held to have the most perfectly shaped ass in the school, a reputation enhanced by her strict wardrobe of skin-tight jeans. I had definitely jacked off thinking of Ms. Jones’s tits – every guy I knew had done that. But thinking back, there weren’t too many girls that really got me excited.

And, if I was being honest, Mr. Robinson wasn’t the first time I’d had the inkling I was into guys, it was just the first time I’d really acted on it. There was Sam Holt that I used to play soccer with, and that time behind the grounds shed at the out of town tournament when he convinced me to suck him off. I had knelt in front of him and grasped his hard-on, but he blew his wad before I could get him in my mouth.

There was jerking off to stolen skin mags with Andy Williamson, and the last time before he moved away, when he reached over and started stroking me, then took me in his mouth as I sat paralyzed, receiving my first blow job. I had spent many days afterward trying to recreate the startlingly pleasureable sensation of him wriggling his finger into my asshole as I came in his mouth.

But, like I said before, the town I lived in didn’t seem to have space for that kind of thing. You grew up, you did a bit of fooling around, you got a job, got married, got a house, got kids, got old, got dead. Everybody knew that. Nobody was gay; that only happened in the big city where life was so decadent and frivolous that any kind of debauchery was tolerated.

That’s what I had thought, anyway. But if I looked at what I had experienced in the last few days, I could see that wasn’t really true, it was just what I had been taught and had accepted without question. Now, Mr. Walters was telling me he had sex with men and women and I couldn’t make sense of it — if you let men fuck you, you were gay, a pansy; if you fucked women you were a real man, it was just common sense. I wondered if Mr. Walters just pretended to like women, to make himself feel better.

“Anyway, Billy,” he interrupted my spiraling thoughts, “you should be cautious of the rest stop. I’ve been in that scene before, when I was like you – young, dumb and full of cum. But there are weirdos lurking around, trawling for stuff that you wouldn’t like. The cops show up sometimes too, when they’re bored, and trust me, you don’t want a couple of deputies catching you getting double teamed in the back seat of your car.” My cock surged at the sudden image of young Mr. Walters doing the things I had been doing, and getting caught. I bit my lip at the thought of being at their mercy.

“I feel like this is going over your head,” he sighed, “but you need to understand almanbahis giriş this.” Mr. Walters looked me in the eye. “Where we’re going tonight is going to be safe, you’ll have fun, but you need to ask yourself how you ended up here, at this moment. You’ve followed your boner from one thing to the next, without thinking once of how it might go wrong, and even when it did, with Wayne, you kept going mindlessly anyway.” He turned back to watching traffic for a moment, gathering his thoughts. “I’ve been there, Billy, I know how good it feels to step away from what the world wants and just be who and what you are. But that euphoria doesn’t last forever, and believe me when I say that just fucking random strangers isn’t enough to really be happy.”

I mulled his words over for a moment, then glanced at our road mate, who was now swiveling his head back and forth constantly. I could see his right shoulder moving rhythmically. I glanced down at Mr. Walters’s slightly deflated member filling my hand and tried to remember the last time I had been as happy as I had been the past week. I couldn’t.

The driver’s eyes met mine and I licked my lips, looked at Mr. Walters’s lap, then back. He looked so pitiful, driving that shitty station wagon, thinning hair, rumpled office wear, the look of need in his eyes. I didn’t want to end up like that, like my parents, like so many other people I knew. Maybe Mr. Walters was right, and I would get tired of acting like a slut some day. But not today.

I opened my mouth and slowly slid my wet tongue over my bottom lip, flicking it up and down. The driver seemed to groan in response, his shoulder moving faster. I dove into Mr. Walters’s crotch and began sucking him like a maniac, drooling, working his shaft and balls, taking him to the back of my throat. I couldn’t see the driver, but I knew he knew what I was doing; I wanted him to know, I wanted him to go home tonight and replay what he saw over and over, I wanted him to wonder what it would be like to get his cock sucked by some random guy, or to take a thick cock in his own mouth.

Mr. Walters stiffened in his seat and I felt the car swerve slightly, then the first volley sprayed the roof of my mouth. I backed off, sliding and twisting my hand over the bulbous head of his cock, receiving four more splattering ropes of semen across my face. I sat up and looked directly at the driver, certain that the mess was visible. His head was thrown back and his arm moved urgently. Mr. Walters flicked the right hand turn signal and pulled onto an off-ramp. The station wagon continued on its way, and I gingerly dabbed at my face with a paper napkin from the glove compartment, unconcerned with how successful I was in cleaning up.

“I’m glad we had this talk, Billy,” Mr. Walters said, catching his breath. He made a left hand turn from the narrow side road into a tree-lined drive paved with cut stone.

We eased to a stop near a two story modernist house, all boxy volumes, rugged concrete walls, and floor to ceiling windows. A tall cedar fence ran from the side of the house around to the back yard. There were several other cars parked in front of us. He tucked his cock away and stepped out, re-buttoning his jeans.

We had only taken a few steps from the car when red and blue lights flashed behind us, accompanied by a short siren squelch. Mr. Walters froze, head slowly turning back over his shoulder, his hands open and held out slightly from his waist. Had a cop seen what I was doing on the highway, I wondered, panic welling up in my chest. I had been aware of the car drifting a bit when I was taking Mr. Walters’s load – was that enough to call the attention of the highway patrol?

I turned around a saw a large man approaching from the parked patrol car. He was wearing a t-shirt and jeans with polished cowboy boots. This was definitely a cop, but he didn’t look like he was on duty. He stopped a few feet away and I could see that Mr. Walters recognized him and had relaxed, but only slightly.

“This some fresh meat, Jakey?” the cop chuckled as he looked me over. I had the distinct feeling that meat wasn’t entirely metaphorical to this beast. I felt like a piece of tender veal as he circled around me, his huge hand running down my shoulder and flank, across my haunches, up my brisket, coming to rest with his thumb firmly on my jaw and fingers gently caressing my hair. My eyes were level with his clavicle, his bulging pectoral muscles rippling beneath the thin cotton of his white shirt. Whisky and cigars and musky sweat rolled off him and I could feel my lips trembling as he tilted my head up to meet his flat brown eyes. His smile was thick lipped and cheerless, his cheeks were ruddy beneath the blonde stubble that ran across his square jaw and chin.

Mr. Walters took a step back. I could hear his feet shuffling on the pavement as he cleared his throat and finally spoke.

“Larry,” he said with a mixture of fear and contempt, “I didn’t know you were coming tonight.” The cop didn’t take his eyes off me, but his lip curled slyly almanbahis yeni giriş as he answered in a drawling bass.

“Nobody told me it was happening but I know what night it is, and Gordon is a creature of habit. I was on my way out here when I spotted your car on the highway and followed you. This little piece put on quite a show,” his thumb trailed across my lips. I realized that I had stepped closer to him, my head clouded by the sheer power of his presence. I opened my mouth slightly and pushed my tongue softly against his callused digit. His nostrils flared.

The firm hold on my head became implacable downward pressure as he pushed me to my knees, my face dragging roughly down his belly, his belt buckle, the zipper of his jeans.

“You know what to do,” he grunted, crushing my face against his crotch. My mouth formed over the warmth swelling in his jeans as I deftly unbuckled his belt and pulled open the snap. Looking up into his leering face, I took the zipper in my teeth and pulled it down, revealing white y-fronts with a growing wet spot at the peak of the tenting cotton. I reached for him and he batted my hand away with his big paw. “No hands, Meat,” he huffed.

A shiver ran down my back and I swirled my tongue over his tip, then grasped his waistband firmly between my teeth and eased it down, moving from one hip to the other, until he flopped out onto my forehead. He was thicker than any one I’d had yet, the bell shaped head flaring to just the same size as the shaft, fat veins forking down its length, about half erect and resting on my eyebrows. Even though he wasn’t as long as Mr. Robinson or Mr. Walters, I doubted I could get more than a few inches into my mouth before being stretched to the limit.

He tipped my head back with his thumb on my jaw, and I felt the front fender of Mr. Walters’s Mazda give way a bit. He slapped my nose with the flat of his cock, swinging it like a rubber baton, dragging his leaking member over my face with occasional swats to my cheeks, and mouth and chin. He forced his thumb into my mouth and pulled my jaw open and I could feel the drool gathering. I was hungry for him, this big, rough man, pushing his fat dick in my face. And he knew it. His eyes burned into me with feral intensity.

I whimpered and tried to slip my wet lips over him. He chuckled and pushed my face back, not gently, following up with a backhand cuff across my temple. I could feel my own cock dripping and throbbing in response to his dominance, and my mind briefly flashed to Wayne and the locker room, at his sudden outburst of violence. I hadn’t liked that part much, but up to that point I had kind of gotten off on his rough treatment.

Was this going to end the same way? At that moment, I didn’t really care. All I knew was that I wanted this towering man’s thick dick and I wasn’t too proud to beg for it. Like he could read my mind, the man in front of me rested the tip of his cock on my lips.

“Beg me for it,” he growled, “beg to suck this dick, boy. I know you want this in your mouth, down your throat,.” His pre-cum oozed and I flicked it with my tongue. I looked up and gave him my most innocent, wide-eyed expression.

“Please,” I moaned, the need welling up from my chest, “feed me your fat prick, let me suck you so good…ram it into my dirty whore mouth… fuck my face with that juicy, thick dong…”

Suddenly he was slamming his dick in my mouth, his right hand pulling my hair, his left locked on my neck. My jaw cracked open as he jammed his member over my tongue and into the back of my throat, my nose was crushed against his pubic bone, the blond hair curling into my nostrils, tickling and scratching until I thought I might sneeze.

Then my head lashed back for a moment, his cock pulling back until my lips caught on the rim of his head, my breath coming in sharp wheezes as his hand tightened on my throat. He started a mechanical rhythm, sawing me back and forth as he used my mouth, his hands in absolute control of my movement, the power in his body overwhelming any feeble attempt I might make to resist.

But I wasn’t resisting. My chin was drenched with a torrent of drool as my mouth ran up and down his pounding tool over and over again. The musky scent of his slapping balls, the damp sweat of his hairy belly, the pungent cigar smoke on his yellowed fingers filling my senses. I barely noticed the gagging croaks forced out of my windpipe each time I was slammed against his crotch. I was beginning to see stars and a red-black cloud crept around the edges of my vision. I vaguely heard the sound of retreating footsteps. As his ballooning cock lodged itself in my throat yet again, I briefly wondered if I was going to cum in my pants.

I was floating in my own mind, my body limp, passively accepting my role as the deputy’s fuck hole. It was so dirty, kneeling on a driveway and taking the cock of some dude I’d seen for the first time less than five minutes prior. I realized my hands were clinging to his ass, holding me upright, his muscles flexing in time with his invading thrusts. Nothing mattered to me except his cock in my mouth, my aching jaw forgotten and burning lips ignored in the blind moment when it seemed my whole world glowed in that shaft of gristle and vein and sloppy heat.

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