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Railroad To The Hershey Highway

Category: Anal Sex
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It was a strange train ride to begin with. The Metro North is always packed to the brains with every type of person you can think of heading home from the City, but tonight I couldn’t even seem to find a seat. I hate having to sit with someone I don’t know; they invariably turn out to be some sort of schizophrenic who won’t shut up, asks you strange questions (“Would you like to know your future?”), or just plain smells.

So I kept walking back, through car after car, until I came to the very last car. The strange part was that it was empty, and only half lit. Puzzled, I looked around for some sort of sign that said it was off limits or something. Perhaps everyone just assumed that because it was half lit. Convinced I was alright to stay there, I took a seat and pulled my hat down over my eyes a bit. Soon, I drifted off to sleep. Last stop, New Haven.

I awoke with a start as the train stopped at Greenwich, and in walked trouble, as the cliché goes. She was the very epitome of having been born with silver spoon in mouth, hand, and with several to spare. Her long brown hair was done up in an elaborate bun, and she carried an expensive-looking purse with an “LV” on it. Probably French or something. Her shoes were fashionable heels, perfectly polished, and she had jewels all over; earrings, bracelets, necklace, and rings. She was completely decked, not to mention stacked. She wore a conservative navy blue business jacket-skirt combination that hugged her every curve. She had amazing legs, sans hose, that were strong and firm-looking, with just the right amount of tan. Her hips and ass completed the deep hourglass curves, and her tits were about bursting out of the blazer she wore. She took a place across the aisle from me and a little ways forward in the car, in a seat facing back towards me. Her cleavage was deep and also tanned, showing no evidence of a blouse underneath. As she crossed her legs I got a quick flash of red panties; her skirt was pretty damn short for the business-like air she gave off. I found myself getting hard, and cleared my throat as I adjusted myself. She looked up at me for a moment, and her proud eyes filled with scorn. I suppose my baseball cap advertising a hometown landscaping company and my punk-rocker clothes weren’t exactly appealing to someone of her stature. I saw her eyes dart down towards my crotch for a second before she sniffed and held up her nose. I scoffed a bit, noticing the bulge in the Dickies was heading down my right pant leg.

“Is something funny, boy?” she sneered at me. What a bitch. I could tell already. From her voice and looks, I’d give her about 30 years. 5’6”, probably 130 with those tits. A bitch, but a foxy bitch if ever there was one. I decided to play with her, see if she’d leave my car and me in peace if I made her mad enough.

“Just noticing you checking out my package, that’s all,” I said, pushing my cap back and folding my hands across my broad chest. She gaped at me for a moment and spluttered, her face turning a little red. I shot a fake, winning smile at her.

“Why you!…you ill-mannered little…shit! I did nothing of the kind,” she retorted, turning up her nose a bit again.

“Why, I detect a hint of defensiveness in your voice, lady!” I laughed. “An innocent person would have been confused and insulted, not defensive.”

She spluttered again, then stopped. “Fuck you,” she said with a sneer. “Leave it to your farm-boy upbringing to breed some sort of…overgrown gorilla penis,”

I laughed again. “Actually lady, gorilla penises are about one inch long. But seeing as how you’re ignorant, I’ll take it as a compliment,” I said. She was getting really mad now, having been shot down twice. “I think you’re curious! Wanna have a look?” I made a mock move to unzip my pants.

“Ha!” she scoffed, “And see the socks you’re stuffing your crotch with? I’d think you’d be embarrassed to prove to me that you’re faking, boy.”

“Pff! You think I’m faking this?” I said, giving my crotch a baseball-style grab for emphasis.

“Yes! Anybody can see that. Only a freak would have a penis that big. It doesn’t make sense,” she said, turning up her nose.

“You want proof?” I offered again with a laugh.

“Go ahead, boy,” she sneered back. “You don’t scare me.”

“Ooookay, bitch,” I said, rolling my eyes. I stood and sat down in the forward-facing seat directly across from her. She crossed her legs the other way, giving me another flash of red. “Nice panties,” I added. “Your mother buy those for you?”

She just sneered at me. I unbuttoned my pants and jerked down my fly, then pulled my cock out of my boxers with some difficulty, watching her eyes get wider with each inch. Finally, it sprang free, wobbling obscenely, sticking straight up a full 8 inches and as big around as an empty tube of toilet paper.

“Jesus…” she gasped softly. I chuckled and stood up as I moved to put it back in my pants. I thought that was sufficient for a lawsuit, let alone getting the rich bitch to leave my car, if for no other reason that the fact that I was obviously crazy. However, in standing up I brought the tip no farther than a foot from her face. My cock jerked slightly as I looked down her deep, full cleavage.

“I should have bet money,” I said, taking myself in hand and starting to put it back in my pants.

“Wait!” she protested suddenly, after her silence. And suddenly her warm, soft rich-girl’s hands were wrapped firmly around my throbbing member.

“Whoa!” I gasped. “Jesus, lady!!”

“Shut the fuck up and sit down,” she commanded, looking into my eyes.

I gulped. “Um, yeah…yeah ok,” I stuttered. How the tides do turn! I sat down in my seat again, her hands still firmly wrapped around my shaft, and she followed me over, ending up on her knees on the floor of the train car. She gave my tip a wet kiss, making me gasp.

She didn’t say a word, but took a hand away and began to unbutton her blazer. I just stared. She had me under her spell, no doubt. There were only two buttons, and after the second her blazer fell open, exposing a massive set of all-natural boobs the size of healthy grapefruits, restrained with a lacy red bra. She smiled for the first time as I reached out to touch her. She recoiled slightly and smacked my hand away. “Do you like my tits?” she asked, licking me once from the bottom of my shaft to the top and hefting one breast in her hand. I nodded again. “Wanna see? I swear I’m not faking,” she said with a devilish smile.

“Ohh God yes,” I gasped. With a twist of her wrist, she undid the front clasp of her bra, and the most beautiful tits I’d ever seen popped free. She released my cock and took both her breasts in hand, straightening up a little bit as she wrapped the soft, warm flesh around my cock and slowly began to stroke me up and down…up and down…the soft, smooth skin sliding over my turgid shaft.

“Ohhhh man…” I gasped, letting my head rest back on the seat. I gasped as I felt her lips on my tip in addition to her tits on my shaft, and looked down to find her slowly giving me the most amazing blowjob of my life! The combination of her soft breasts and her hot mouth was driving me insane! Suddenly, she stopped, giving my cock one last suck before releasing me and standing up.

“Don’t think I’m going to make it that easy for you, boy,” she taunted. You’ve got to give me something first.”

“Anything!” I breathed. She pulled up her skirt a bit and pulled down her panties to her knees, then turned her back to me and looked back over her shoulder.

“Put it in my pussy,” she said softly, with a wicked smile. I took myself in hand and held my shaft straight up as she slowly lowered her hips down onto my lap. I felt for the hole to make sure I hit it right, finding that she was shaved smooth! Man, what these rich girls get up to! I had barely time to finish the thought before I felt her slick, wet lips suddenly envelope my tip and slowly slide down my cock, engulfing me in her hot pussy! She didn’t stop until her butt was resting on my abs. “Ahhhh yessss!!” she hissed. Putting her hands on my knees for balance, she slowly began to bounce her hips up and down on my cock, my shaft sliding smoothly in and out of her hot, rich-girl pussy. She was so wet that it was running down over my balls and making hot little noises as we fucked.

“Uh! Uh! Uh! Yes! Yes! Oh, yes give it to me!” the lady cried, her head back and her eyes closed, her butt bouncing up and down on my cock with a nice rhythm, my shaft slipping easily in and out, in and out of her tight, wet pussy. “Ohhh fuck I’m coming! Yes! Yes! Uuuhhh God yes!!” she cried, her rhythm faltering as her orgasm washed over her, her body shaking and her pussy squeezing my cock for all it was worth. But even after she came, she kept going! The insatiable bitch probably hadn’t had a good fucking for years! All those up-tight rich boys don’t know how to really let a girl have it! I took hold of her hips and pounded up into her pussy on the down stroke, making her squeal with pleasure. Suddenly, she stopped, breathing hard, and took to swiveling her hips around on my shaft, buried deep in her vagina. She looked back at me.

“My stop’s coming up…” she breathed, “But I’m not done yet! I’ve still got one more hole to plug…”

I gasped. Without a word, I wrapped my arms around her and picked her right up, never losing the connection, and we traded places. Now, she was kneeling on the seat, her delicious ass sticking out invitingly. Her buns were nicely tanned, smooth and hairless. Even her ass crack had been waxed! There was slight evidence of a tan line from a skimpy little thong, too.

“There’s Vaseline in my bag. Hurry!” she whined. God, was she horny! Her pussy was glistening, and her tiny little gray-pink pucker winked at me invitingly. I reached into the bag and brought out the jar, slapping a big dollop of the greasy lube onto her pucker and rubbing it in while I put some on my shaft at the same time. She looked back at me over her shoulder and licked her upper lip, gnashing her teeth slightly before putting on a pleading face. My, how this uptight rich girl had changed in the last 10 minutes! I pressed the tip of my cock against her staunchly resisting pucker. A soft, piteous moan escaped her lips, followed by a wavering cry as the head slowly forced her open and popped into her ass. “Jesus!” she cried. “It’s huge!”

I took hold of her hips and slowly started to feed my meat into her ass.

“Uuunnnggghh! Oh!Oh!Oh! Uhhh Gawd, please! Be…be gentle!” she pleaded, looking back at me. The Vaseline worked well, and her well-lubed back door was eagerly accepting inch after inch of hard cock. With every passing second, the lady’s whines and moans became more piteous. “Uhhh Gawd!” she whined, her fingernails digging into the cushioning in the back of the seat. I didn’t stop until I felt her warm, wet pussy on my balls, my cock firmly planted in her tight backside. “It’s so…so…unnngggh! So deep!” She whined. “Do me,” she whined, looking back at me again. “Fuck my ass like it deserves to be fucked!” With a wry grin, I followed her orders. I withdrew my cock all the way to the tip, the slammed it back into her ass all the way to the balls. She bit the back of the seat and whined, my thrusts punctuated with little squeals of mixed pain and pleasure. I held her hips tight, our bodies coming together with a sharp slap as my cock plunged in and out of her booty, gliding smoothly back and forth in her greased rectum. Fuck, she was tight! Her anus was wringing the life out of my cock. Had I been a day older, I might not have had the stamina to keep her from cutting it right off!

In and out, in and out, over and over I fucked her ass. I could tell she wasn’t an anal virgin, but she sure as hell could have fooled me with how tight she was! She moaned and cried, whined and groaned, biting and clawing at the seat cushions as I fucked her ass faster and faster, my orgasm approaching quickly. She was rubbing her clit as I fucked her, and it was beginning to have an effect! She shrieked shrilly.

“Fuck!” she cried, “Fuck I’m coming!! Uuunnngghh!!”

Her rectum rippled around my cock as her second orgasm of the ride washed over her, her hot body quaking and shaking with the force of it. I couldn’t hold on any longer. Her ass was just so hot, so tight, and her selection of lube made it all the more intense. I watched as my cock slid quickly in and out of her bum, my mouth agape as my orgasm boiled up in my balls. She looked back at me.

“Don’t come in my ass!” she begged.

“Then we’d better do something quick!” I rasped, fucking her even harder.

“Ooo! Oh! Jesus! Uh! Ok! Ok,” she said. Suddenly, just as I was about to blow a monster load directly up her hot little derriere, she pulled away and whipped around, sitting on the edge of the seat in front of me. She grabbed my shaft and stroked me once or twice. That was all it took before the orgasm came. She looked up into my eyes as I blew the biggest load of my life. She held her tits with one arm while she stroked me with her free hand, my load painting her breasts with spurt after spurt of hot white come. It splashed on her neck and clavicle, slowly running down and pooling between her tits. Big white ropes lay criss-crossed all over her cleavage. She wrung out the last drops with her hand, making me gasp, then quietly re-clasped her bra and adjusted herself within it, making sure it was comfortable. The train began to brake.

“This is my stop,” she said, standing and whipping out a compact to check her hair before buttoning her blazer and pulling up her panties. As she bent over to do so, I watched my load run over her tits, draining a little down between them and running over her bare belly. I barely had time to stuff my greasy cock back in my pants before the train stopped and she stepped out, my come all over her prominent cleavage in plain view! She walked past several people who got onto the car, and none of them seemed to notice that she was sporting my load all over her tits.

I slumped down in a seat, breathing hard. I felt like I had just been hit by a tornado. My cock, still a little greasy with Vaseline, was sore; her butt had been that tight. My balls ached, too. I don’t think I’d ever had them drained quite so completely before.

“Sheesh,” I pondered aloud, chuckling a bit. “I didn’t even get the bitch’s name!” Only 15 minutes had passed since the mystery rich girl stepped aboard, and in another 30 I was back at my house at college, having a beer with my buddies. What a night!

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