Best Laid Plans

Story Info
Passionate young couple says goodbye at the train station.
5.9k words
3.87
16.2k
14
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
RubyRyan
RubyRyan
10 Followers

I can't believe it's finally today.

I can't believe this is actually happening.

Ok, breathe, Jessica.

Breathe.

Just have a seat on the bench until the train arrives.

Breathe.

People make it out of their hometowns all the time.

This is not a weird thing.

I'm almost there.

Let's make a mental success list while we wait: I graduated . . .

Wow. Is this bench vibrating? Good lord. It IS vibrating. How funny. Oh, I bet it's some kind of machinery beneath the floor. Right. Focus. So, I graduated, and then the breakup with Jack could not have gone better. Like, I never, ever dreamed it would go like it has. He's been so good, helping me with everything. You know, I can't help but think that if he'd been like this all these years, I don't know that I would have worked so hard to get out of this town.

Damn, the vibrating stopped. Well, ugh. That was starting to feel good. Did I just say that? Or think that? A vibrating bench felt so good? Really, Jessica? Sitting in an empty train station, regretting that a bench stopped vibrating. Maybe I really am just a trashy girl at heart. Well, let's be honest, it's not far from the truth. The breakup certainly didn't keep Jack out of my panties. Maybe that's why it's gone so well, I laugh to myself. He has still been able to fuck me pretty much anytime he wants. So, not much has changed.

Oh, god. There it goes, again. Mmmhhhhmmm. I cannot believe how good this feels. I guess one good think came of me not wearing my favorite jeans this morning - this skirt is so much thinner. Maybe if I shift my weight just a little, I can feel it against my clit . . .

Ugh. It stopped. Jesus. I'm practically panting.

Ok, let's get a grip. Slow your breathing and try to ignore the throbbing. Keep thinking:

I got a job in the city and a great new apartment. All those years of working part time paid off. I used almost every cent of my savings to get set up. And the new furniture . . .

Yes, thank god, I think. That machinery beneath the floor is about to make this day even better. Yes, keep vibrating. Oh, god, yes. I'm just going to rock a little, too. mmmmm, mmmm, oh, god, this is crazy, yes . . .I think I caught a long cycle. This is the longest it's run so far. Oh, god, I'm so close. I just need a little more pressure. Oh, please. God, don't let it stop.

No, no, no, no, no.

I am so close. This can't be right. I am so close. Oh, god. Oh, god. Noooooo. I start to reach into my skirt when I remember I'm sitting in a train station, and my eyes pop open in horror.

I'm still the only one on this platform. I'm ok.

I can finish out that orgasm tonight in the privacy of my own apartment.

Oh my god, this is so exciting! My own place.

Everything is going to be fine.

Just a few more minutes until my train arrives, thank god.

(Slow train sounds)

"Jess? Is that you?"

I think I hear my name and turn to see Jack and his brother walking toward me on the platform.

"Oh, hey there!" I turn. "You almost missed me. I think my train is just pulling up," I blurt excitedly, meeting them halfway.

I'm so surprised and excited by the turn of events that it barely registers with me when Jack's brother plucks up my suitcase and walks away.

"Where have you been lately, Jack? I've really missed all the fun we've been having," I whine suggestively.

"Awww, baby. It's your period week, right?"

"Oh," I gasp, blushing crimson. "Right. Right. I didn't think about that." Is it my period week? Was it supposed to be my period week? I am so confused.

"So, today's the big day," Jack starts, distracting me from my thoughts and drinking me in from head to toe. "My little lady is leaving me behind," he whispers into my ear, pushing me back towards the bench, but at least she's wearing my favorite skirt!

"My fat skirt? You are so weird," I counter, pushing him playfully.

"Mmmmhmmm. I was hoping you'd be wearing it," he purred.

"You just like it because it promises easy access. You are not fooling me," I tease.

"I have no idea what you mean, sweet girl," winking and kissing my forehead, Jack continues to push.

"Any idea where Jason is going with my bag?" I huff as we backwards dance, and I try to catch a glimpse of his disappearing brother.

"Jess. Baby," he sighs and rolls his eyes. "He works here. He'll take care of it. Everything will be fine," He soothes.

And just like that, I'm back sitting on the sometimes-vibrating bench with my very tricky ex, my bag has disappeared, I am unbelievably horny, maybe late for my period, and my train out of this nowhere place is nowhere to be found. How is this happening? I cannot get sidetracked. I may just have to forget the bag. Orgasm at the new apartment. Just find the train. Everything is going to be fine . . .

"Jess? Are you in there? Were you meditating?" He laughs and scoots down the bench.

Putting his arm around me, we make small talk. I ask about his family, and he really starts talking, really just on an on. And I am so glad, honestly, because I can space out and focus on the growing warmth between my legs. Oh, my god. I think I might make it this time.

My eyes start to glaze over as he talks, and I smell his familiar aftershave right before I hear him chuckle into my ear, "You're almost there."

"Damn it, Jack!" I shout as I try to get up off the bench.

"Oh, no, no, no, sweet girl. You know it's rude to hop up and leave during a conversation," he mocks, tightening his grip and fixing me more firmly to the spot. "You need to sit here and let me finish telling my story," He continues. "You wouldn't want to be rude to me on the day you leave, would you, baby, hmm?" As I relax against his grip, he purrs into my neck, "That's my good girl. Mmhmm. Look at those hard nipples. Jesus, your tits look amazing," Jack gushes, cupping and roughly kneading my tender breasts, "I'm going to rub those little nipples."

"Jack. Please don't." I plead.

He does not listen.

"I'll just do it on top of your shirt. No one can see us, baby. Just relax," he offers.

"Just be gentle. They are so sensitive . . . Oh, Jack. It does feel so good," I groan and start babbling incoherently, trying to fill the quiet with something other than my moans: "My clit is throbbing. My nipples are so tender. I couldn't fit into my favorite jeans this morning. This bench vibrates occasionally. I don't know if you've noticed, but I certainly have, and I can tell you it's never gone this long before. I think I might be able to have an orgasm."

"Mmhmm, baby. This is so hot. Let me watch. Fuck, I really don't remember you ever being this horny on your period before. You are so hot. Don't worry, I'll keep working on these nipples," he whispers and winks.

I can't spend too much time thinking about the period comment or why or if I should be publicly masturbating with my ex. I just know that I have to catch this orgasm. I was already overdue for one when I fell prey to this damn bench. Mmmmmmm.

"I'm not on my period. I'm just regular horny," I say. "I think your calculations must be off," I tease him, laughing and starting to flush.

"Oh, yeah? Hmm," he considers my statement briefly and shrugs. "That's my girl. Look at you leaning into it. God, you are amazing," he coos, never taking his mouth away from my ear or his hand off my tender nipple.

"Oh, my god. Oh, my god," I moan, finding the right cadence and pressure on the bench

I feel Jack move away briefly, and then he is between my knees with his mouth on one nipple and his fingers on the other, kneading and pinching mercilessly. When did he get my shirt and bra up like this? Jesus, he's so fast. But my god it feels so good.

*Upstairs in a dark station office, overlooking the platform*

"Alright. That's the signal," Jason announces after spotting Jack. "Count to 5, and then we cut the power to the old boiler.

"What's left?" asks Chris, a guy on the crew who does actually work at the train station.

"Ok," Jason runs down his mental to do list, "I gave her bag to you. We wait until he has her inside the old stationmaster's office, then we lock that door from the outside behind them and head out. You'll need to take her bag and put it in the backseat of his truck," Jason explains calmly.

"Kind of presumptuous to think she will go home with him after all this, right?" Chris remarks, indignantly.

"She doesn't really have a choice, Chris," Jason replies flatly.

"Dude. Don't you think this is a little fucked up?" Chris asks.

"Eh," Jason shrugs without judgment. "That's my brother, and Jess is his woman. I don't ask those kinds of questions. It will be fine, though. Just wait. You'll see," Jason explained with a look that spoke of experience.

"Well, now that I've lodged my morality police complaint, I'll also say that this is Hot. As. Fuck. Jess on that bench will definitely be on my mental hard drive for a long time," Chris confesses with an appreciative chuckle.

"Here's a tip," Jason begins, putting his hand on Chris's shoulder. "Keep that shit to yourself. I know you are new to our crew, but it's smart to keep thoughts, words and deeds related to THAT girl to yourself and if not, they should be as pure as the driven snow. He's put people in the hospital for less than what you just said."

Raising his hands in surrender, Chris backtracks, "Got it. My bad. Won't happen again."

But Jason continues, laughing, "No, I get it. We ALL get it. Trust me. She's been his for so long that I forget normal people can see her as something other than Jack's."

"And so you're telling me that three months ago, completely out of the blue, she decided to break up with Jack and start a new life somewhere else, all by herself? What the fuck?" Chris asks, confused but also chuckling.

"Yeah, exactly," Jason starts, sharing Chris's amusement. "When Jack told his us that Jess broke up with him and was planning to move away, we were beyond shocked. I mean, no one even reacted. We just sat there, waiting to see what Jack was going to do. I guess we were waiting for his plan, really, because of course there was going to be a plan," shaking his head. "I'm telling you, man, Jack's rage was nuclear, or whatever it is when it's so hot it's cold. Like a fucking blackhole or something. I don't know. Whatever. I'm not a scientist. He was really fucking mad," Jason says, laughing and wiping the back of his hand under his eye.

"And so, Jack finishes talking through his plan, stands up, and asks the larger group if there are any questions. No one wants there to be any questions, and we are all just hoping to get the hell out of that room. And I'll be goddamned if one of our newbies didn't raise his idiot hand to ask a question! There was an audible groan and then we all turned to look for the dumb motherfucker asking a question," Jason continued, chuckling.

"I swear, that scrappy fucker piped up and asked the one question that was on everyone's mind:

"So, um, did she really think you were just going to let her walk away?"

"And just when we thought he might kill the newbie and us and anyone else who just didn't look right, Jack broke out into a big smile, raised both of his hands in the air, saluting his newfound comrade in confusion and said, "Thank you, my friend. Thank you."

*Downstairs on the bench*

"Are you ready to cum?" Jack purrs through a grin.

"Yes, Jack. Yes. Oh, my god. Yes, please make me cum. I need it. I'm so close," I pant.

And just like that, the machinery beneath the floor shuts off, and the bench stops vibrating.

Like a fiend, I rock on the wooden slats, frantically chasing the tail of that orgasm.

"Aww, sweet baby," Jack coos, leaning in to kiss my neck and pinch my nipples. "Come on. Let's go in the stationmaster's office, and I'll finish you off," he hops up and begins to pull me towards the office.

"Jack, I can't," I whine, "My train . . ."

"Sweet girl, your train isn't even here yet," he reassures me. "Come on, now. Be a good girl. Don't you think you owe me a little extra attention today? I know you certainly appear to need a little more of mine," he teases.

"Ok, but can you make it quick? I'm nervous about my train," I whimper, knowing that I'm taking a risky detour walking towards this office.

"Of course, baby. I know you've got big plans. I won't keep you any longer than I have to," he whispers against the top of my head, pushing me into the office and closing the door behind us with a firm click.

"Wow. I didn't realize how beautiful this office is. The old stained glass, and look at this," I say, pointing at the huge, stately wooden desk in the middle. "I guess no one ever figured out how to steal it," I say, running my hand along it's leather blotter top. "It's about the only thing left in here besides dust and trash," I note offhandedly, looking around.

"Kind of like this town, Jess? Is that what you were thinking?" Jack bit out with surprising venom.

"No, not just like this town. That's not how I feel about it. We've had this conversation before, Jack. Come on," I snap back at him with a little more heat than necessary. In response, I watch Jack's jaw set in a familiar line, and the change in his visage gives me pause. Holy shit. I am missing something here. Jack takes a deep breath, cracks his neck and continues his unnerving stalk at the perimeter of the room.

Sensing the dangerous shift in atmosphere, I take my shot and bolt for the door. If I can get to it a little before he does, I will give myself a chance at getting the heavy door open. My brain is screaming to move! Go! Don't look back! And when I reach the door, he isn't there. I have made it! I have a chance! I yank down on the large handle, preparing to pull that monstrous door with all of my strength and bolt back out to the platform. But instead, I find that the handle doesn't move at all.

The door has been locked from the outside.

I don't need to try it more than once. I should have known. I take a deep breath, brush down my skirt, and quietly back away from the door.

Jack doesn't say a word, having never even paused his pacing when I attempted to bolt. Why would he? He knows I can't get out of this room. He knew it would be locked.

I turn and face him, finding amusement on his face. "Jason, I'm guessing?" pointing a thumb back at the door, sheepishly. And so now I know I'm in trouble. I'm inside a game of Jack's. I don't know what's happening, but this does not feel good."

I watch him for a minute, walking and thinking with a deep scowl. I've known him all my life, but THIS Jack is new. This is a Jack I don't know.

When he turns his attention to me, I begin to back away, pleading, "Things have been so good between us, Jack. Let's not say goodbye like this." His expression only grows more amused as he closes the distance between us. I continue filling the choking silence with absolute nonsense, "You helped me get my apartment and pick out the furniture. I couldn't have done it without you, and we've had so much fun the past few months, Jack. . ."

And then I realize I can't back up any farther. He's pinned me against the desk.

"There we are," Jacks says with a satisfied grin. "Now you should be a little easier to manage," he rumbles, pushing down on my shoulders with both hands, giving the universal sign for "suck my cock."

I slide down to my knees, complaining that I thought the point of coming into this office was to finish ME off, not him.

Jack chuckles dismissively and wastes no time stuffing his dick in my mouth.

"Awww, fuck, yes. That's what I'm talking about, baby girl. It's been way too long without getting inside you. Ahhhhh. Damn, I love this mouth," he groans, shifting his hips forward, bottoming out in my throat and pinning my head back against the desk.

Looking down at me, Jack tips his head to the side mockingly and says, "I'm sorry, baby girl. I don't think I heard your complaint the first time. Maybe you could try saying it again with a mouth full of my cock? It would at least be amusing that way, don't you think?"

Jack waits to check my submission before he releases the pressure on my head. I take a deep gulp of air around his dick and settle my hands on his thighs. Jack wastes no more time and begins to slide his cock in and out of my mouth.

"Oh, yeah, Jess. Suck my dick. Fuck, this is the best view in the world. Oh, you know what? It needs those naked titties. Pull that shirt and bra back up so I can see them while you suck my dick," he demands. I comply and start pulling them up, but Jack pops his dick out of my mouth and roughly yanks both bra and shirt over my head, tossing them off onto the floor out of sight.

I whine and start to issue a complaint when Jack chuckles and simply puts his dick right back in my mouth.

"There we go. That's much better. Right where you belong," Jack groans. "Those big boobies swaying while you're staring up at me from the end of my dick. Fuck, yes! Oh, but look. You're all dusty and on your knees, and it looks like you've lost your shirt and bra, little girl. And here I was thinking you're a fancy city girl, not a dusty, little small-town whore," Jack coos sadistically. With an amused laugh, he lets his head fall back and enjoy a series of thrusts before sliding his dick out of my mouth and patting the desk. "Get up here on your back," he encourages, in a much sweeter tone.

"Jack. You are being such a dick," I whimper as I climb up onto the desk.

"I know, baby. You're right. Let me make it up to you. You get up there and lie back. Scooch way down for me. I'm going to make it all better. Hold those legs up and out. You know how to do it. That's my girl," he cooed as he began to kiss up the inside of my right leg. "Oh, this pussy is marvelous. It feels so long since I've had it," he muses, running his fingers along my swollen lips, just shy of where I want. "You're so fucking needy right now," he says admiringly.

Jack surveys his prize and then, leaning forward, smoothly pushes down on my upper body, settling me back before him on the desk. Apparently enjoying his handiwork, Jack runs his hands over my splayed body, grinning at me with a look of satisfied ownership. Finally bowing his head to my pussy, Jacks murmurs, "Oh, fuck. This is going to be so good."

Licking up and down in ever smaller circles, he barely grazes my clit with each pass, methodically working me into a frenzy before even turning his full attention to my clit.

"Jesus, Jack!" I scream.

Approaching with a broad, flat tongue, Jack presses his mouth against my desperate core. My body convulses in overwhelming pleasure, bowing up only as far as his upper body strength will let me.

"Oh, yes. That's it. Oh, Jack. How do you know how to do this to me?" I beg.

Resting back on the desk, I moan the relief of someone who knows they are in knowledgeable hands.

"There she is. There's my good girl. I'm about to make you cum, Jess. I own this pussy and you know it."

"Oh, my god, Jack. Oh, my god," I begin moaning, letting my head fall back while my hands find my nipples.

"That's it. Tell me about it," He growls.

"Oh, fuck, Jack. You make me feel so good," I wail, drunk with lust.

"Tell me who owns this pussy, baby," he demands.

"You do, Jack. You own my pussy. It's yours."

"mmhmm. That's right baby. This is fucking mine," he growls.

And with a series of quick flicks of his tongue, the spark blooms out of my core and sets me on fire.

"OH, MY GOD, JACK! I cry.

"Tell me now, Jess. Tell me who owns this pussy," He demands again, quieter this time, shifting his body around subtly.

"Oh, Jack. It's yours. My pussy is yours . . ." I groan, barely louder than a whisper, closing my eyes and basking in the retreating waves of my orgasm. My sex quakes and spasms in relief, and the slightest hint of a tingle still glows around my clit.

RubyRyan
RubyRyan
10 Followers
12