How lucky can you get?
Lucky Strike
By Henry Anthony Courtler
You couldn't believe it, but it really happened. After a close friend of yours over in Manehatten promised to introduce you to your idol, Octavia, you were simply expecting a chance to hold some small talk, but you ended up with more than you bargained for. The two of you had hit off better than you could have ever dreamed of. Several months later, you had finally managed to convince her to give things between you a chance and you had started dating.
Admittingly, she was drop dead gorgeous and didn't take much to know it. That's why it always felt surprising that a mare of such beauty and class would ever come to like you romantically. It was a one in a million chance, but she had proven to be your lucky strike. But not all things were perfect in your relationship. You have been dating Octavia for almost a year, but you haven't been able to make much progress on the intimate side of things. Octavia just seemed to enjoy winding you up, but always left you hanging. It was like a perpetual game of cat and mouse, only she made the rules. The most you had been able to do with her was merely french kiss in the occasional hallway or at some event, and anytime you took initiative, she would just brush her tail against your face and saunter off elsewhere, your eyes following the sway of her tight flank all the way.
Tonight was no exception in the slightest. You sat in the front row of the Canterlot Theater along with all the uptight V.I.P guests, who had made large contributions to pay for the show. None of it mattered though as you watched Octavia eloquently play the Cello with her hooves and mouth. Her hooves quickly and efficiently changed chords while she dipped her head gently across the Cello, the bow expertly strumming the strings with tenure. She had set her dark brown mane down from its usual slicked back style, allowing her mane to flow down into her shoulders. A tight, yet loose maroon colored dress covered her light grey coat, ending just above her seated flank. It took all your self-will not to become erect from the mere sight of her magnificent body. Thankfully the tux you were wearing forced you to control your breathing lest you wanted to break out in a hot sweat.
You had been focusing so tightly on Octavia, that you hadn't noticed that she had finished the last piece of the set until the stomping of hooves snapped you out of it. Stomping along with the audience, you look up just in time to catch your love gazing at your with her alluring brown eyes. Nodding her head towards the backstage, you silently acknowledge and wade through the crowd of ponies. After trudging through the thick crowd, you finally reach the backroom where nearly all the orchestra members are relaxing and talking amongst each other.
You politely greet the ones who you know are close to Octavia and respectfully nod towards the rest of them. Reaching the farthest corner of the room, you catch Octavia putting away her cello with her back towards you. Silently, you approach her until you can hear her muttering to herself about cleaning her instrument. Smirking to yourself, you try your hardest not to chuckle at her tendency to berate herself over the smallest of things. Decidedly feeling bold, you smack her tight flank causing her to yelp in surprise.
"How dare you lay your filthy hooves on m—" Octavia said with restrained anger as she turned around before noticing you, "Oh, I'm so sorry handsome, I thought you where one of those uptight snobs who think that I'm nothing more than a delectable treat to be had."
"Don't sweat it honey, you're not the only pony fed up with them." You say with a small growl. It always irked you to no end how some ponies acted as though they could just waltz right up to her and try whisk her away for the night as though she no more than a play thing. Key emphasize on try before you scare ‘em off.
She gives a sultry kind of laugh, "Somepony feels jealous, huh?"
You scoff in a pompous manner, "Not my fault that you catch every stallion's eye. Pretty soon you might have to reconsider beating them off with your Cello if you don't stop being so damn attractive."
"Awwww. You don't like me being 'attractive'?" She asks with a childish pout, "Guess I should go put my mane up in a bun, wear thick glasses, and call myself a librarian then?" Octavia jokingly says.
Looking her over, you try to imagine her as a librarian, but the mere thought just screams seductive in your mind, "I don't know Octavia, guess you should discipline me for all those late fees, huh?"
She slowly saunters up to you, her face inches away from yours, "Maybe..." Octavia begins with a slight purr, "You could teach me a thing or two about being a librarian, Mr. Scholar..." sensually, she bites her lower lip gently before walking by you, her long dark brown tail brushing softly against your muzzle.
You stand there feeling stunned by the vivid imagery implied by her simple jest, "You coming sweetie, or do I have to drag you along like a lost pet?" She teases.
'Y-yeah, I'm coming" you stutter out weakly, your legs shaking just a bit from the look of pure intimacy etched across her sharp features.
The two of you wade through the crowd, saying your good evenings and goodbyes as you make your way towards the side exit. Once you follow her through, she heads down a short flight of stairs and out into the back lot where several chariots are stationed for the orchestra and the guest. She walks past the chariots with that same breathless air about her, turning heads left and right as she goes. Bringing your hoofstep in line with hers, you notice some of the jealous looks from other stallions and even a couple of mares once they notice the flirtatious smile Octavia flashes you every now and then. Grinning to yourself, you feel proud that you can say 'I have a great gal that turns heads everywhere she goes' without being ridiculed by your peers.
"Where are we going? The chariots are that way." You say, pointing a hoof at the distancing lot.
Octavia giggles flirtatiously, ignoring your comment as she saunters onwards down the nearby street corner.
As you both walk several blocks down the street, everypony that happens to be out this late continue to turn their heads as you both approach a nearby hotel. You realize as you are lead in by your beautiful marefriend, that it is a five star hotel, the Canterlot Hotel to be exact. Octavia walks right by the check-in desk, and walks towards the elevator, and rings one up.
You eye her up questioningly, "Aren't we going to check-in?"
She merely giggles again just as the elevator opens up. You follow her into the elevator, feeling just as confused as before. Octavia presses a button on the panel, but it isn't till the elevator starts to ascend that you notice what floor she picked—the top floor.
You look at her, but don't say anything. The two of you stand next to each other, enjoying the amicable silence, until her tail keeps caressing your back gently. Looking over at her, you notice Octavia smiling gently at you with half-lidded eyes, lusting eyes.
"You look positively dashing in that tux of yours." She comments seductively as she runs a hoof across your shoulders.
Shuddering slightly in delight you reply, "And that dress you're wearing is driving me positively crazy."
"Oh really now?" She asks incredulously, "so if I do this," Octavia says as she tosses her hair over to one side, reminding you of the classic jazz singers, "Does that really drive you crazy?" She finishes with a confident, sexy smirk.
Instead of answering her, you push your beloved up against the wall of the elevator and ensnare her soft, luscious lips in a heated, passionate kiss. As you kiss the mare of your dreams, you gently run your hoof through her hair, enjoying how she flinches in surprise before kissing you back with equal vigor. You keep it up until you're both left gasping for air. As the two of you separate, a thin trail of saliva is the only thing left to show for the intense moment of passion you had just shared.
Octavia looks over at you with a calculating gaze, a small smile tugging at her lips, “Something must have possessed you to take so much... control, honey.” the words seemed to drip with desire as started to press up against you once again.
The praise alone seemed to do wonders for your confidence, “What can I say ‘Tavi, I’m the kind of stallion that loves to please. ”
A slow, luscious laugh escapes her lips as she wets them sensually, “You did an excellent job at pleasing, darling...so well in fact, that you’re making me feel so...wet.” she breathily whispers into your ear.
Your body shakes like an earthquake as you feel all the tension melt away. The way she says the words you've so desperately yearned to hear just feels right to you. Her brown eyes seemed like melting pools of chocolate passion as you ensnare her in another kiss. She pushes you up against the elevator door and wrestles with your tongue for control, her hooves running deeply through your mane.
Suddenly, the elevator door slides open and the two of you fall into a tangled mess of hooves, but yet you persist to kiss her. It's only when you feel her pull apart from your lips with a wet pop that you remember the need to breathe.
Helping Octavia to her hooves, she drags you along softly up a small flight of stairs and into the open air roof of the hotel. A large in-ground pool was built at the left side of the roof, reflected every ounce of moonlight that penetrated the lightly clouded skies above. All kinds of plants were spread out to help create a more tranquil atmosphere.
Octavia turned to address you, "So stud, are you gonna give me a piece of you or do I have to take some?" She said seductively, further pushing your buttons.
You take several confident steps towards her until your faces are centimeters apart, "I think I'll have a slice or two of you." You growl out huskily as you ensnare her in a smoldering kiss of fire and hunger.
“Then come and get some.” Octavia teased.
Every last shred of your self-restraint seemed to break in that moment as you ferociously made out with her, dropping to the floor as you battled for dominance with your tongues. Each caress of her tongue pushed you further along and each caress you returned brought her passion ever so higher. As you two rolled along the ground, neither of you paid attention to the direction you were heading in until both of you fell into the pool with a surprised yelp.
Once she realized where you two were, she giggled seductively and pressed her body against yours in the shallow end of the pool. She flipped her wet mane to the side and gazed at you with her chocolate eyes.
“Never thought our first time would be in a roof top pool of a hotel.” you comment with a small laugh.
Octavia laughed as she gives you a small kiss, “A lot of things are unexpected in life, darling.”
You kiss her back, “Oh really? Care to give an example?”
“Certainly.” she says with a devilish smile.
Waiting for her to do something, you gasp quietly in surprise when you feel something tug your erection. Looking up, Octavia flashes you a seductive grin, eyes slightly lidded like a hunter about to strike at its prey. Leaning up, you try to kiss her, but she pushes you back into the water, hoof gliding up and down the length of your penis. Your eyelids droop slightly as you revel at the electric ecstasy travelling out from your erection. The way her hoof expertly serves you leaves you panting softly for breath. Taking notice of how much pleasure she causes you to feel, she leans down and enraptures your lips for another tightly locked kiss.
“Enjoying yourself there, darling?” Octavia ask with a wink.
Instead of responding, you grunt softly, your hind leg bending upwards and rubbing into her marehood softly. She gasp softly before slowly moving her crotch in the opposite direction of your rubs, creating a slow, steady rhythm. Her hoof begins to squeeze tighter around your shaft as she pumps you harder, trying harder to reach her prize. You try once again to lean up, and she allows you to this time, not expecting you that you would shower her with hot, short kisses from her face down to her chest, mixing in long licks with the building passion.
Suddenly, you feel your dick throb excitedly and you know your climax is imminent, “‘Tavi, I’m going to c—”
“No, you most certainly are not. If you really want what you have been waiting for, I request that you last or you’ll have to wait even longer.” she added with a slight growl that just managed to stir your loins even more.
You whimper pathetically as you feel her try to push you over the edge, but you try your hardest to resist, eyes squeezing shut as you concentrate on anything but the pleasurable stimulation. She bends her head down and gives your stallionhood a tentative lick and you could have sworn your load was going to blow over both of you when all the excruciating stimulation suddenly stopped.
Opening your eyes, you watch Octavia remove the dress before tossing it by the pool edge, “That suit needs to come off you know...” she whispers into your ear.
Quietly you stand up and feel her removing the cuffs before pulling off the tuxedo and dress shirt, feeling her rub your flanks and brush your side. Your erection twitches from the return of stimulation and you sigh eerily comfortably as you try to control your breathing.
Grabbing your hoof, Octavia drags you out of the pool and forces you to sit on a pool chair, your whole body stretched out relaxingly from head to hoof while your erection stood proudly, “Somepony seems excited to be here...” Octavia teases with a wink.
“Only for you.” you growl out huskily.
She merely smiles at you before climbing on top, her sopping, aching vagina ready for a good plowing, “I’m ready.” she whispers into the crook of your neck.
You smile as you kiss her gently, “You have no idea how bad I’ve wanted to hear you say that.” you say as you gently lower her torso by bending your high hooves.
She moans lightly when she feels your hard erection pressed against her sex, "Ooooohhhhhh...." she cooes out softly.
You wrap your hooves around her tight flank and thrust up while pushing down on her flank, forcing your length deep into her marehood. Octavia gasps, her entire act broken by your entry.
Pull out and pump back. You follow that simple rhythm until Octavia begins to feel the heat build, making her thrust her curvaceous flanks against yours to the beat of your every thrust to her pelvis.
“Ah! Right there, darling! Right there!” she screams in ecstasy as you consistently nail her most sensitive spot, a smirk of satisfaction forming on your face.
Deciding to get even bolder, you flip your bodies so that you’re on top while she lays on the bottom receiving it from you even harder, her hips keeping up one to one with the fucking of a lifetime you're giving her.
Sweat begins to pour down your face, dripping from the tip of your muzzle onto her sweat covered face, her coat having a plastic sheen-like quality to it from all the moisture. Her tongue lolled out uselessly as she submitted herself entirely to the powerful waves of pleasure she felt that made you wonder how you weren’t in the same state.
Her marehood was tight and gripped you like a vice from the moment you entered her, and you could have sworn you would have blown your load then and there if it you didn’t have better self-restraint. Either way, you were finally getting acquainted with the feeling of her love canal and you were loving every damn minute of it.
Suddenly, her walls began to constrict you further, “I’m...getting...close!” Octavia yells in a higher pitch voice.
You grunt as your balls tighten just at hearing her say that, “I’m getting...there too, ‘Tavi!” you growl back as you desperately fuck her before completely bottoming out as her fluids drench your pelvis and your thick creamy seed fills her sex before spilling out with her juices.
Falling onto your side, you merely grin at Octavia as you bring her in closer for a kiss. Octavia merely melts into your kiss and sucks lazily on your tongue before pulling back, “Was...the wait...worth...it, darling?” she asks between heavy pants.
“Hell...yes...” you pant out before starring lazily into the night sky, feeling like you had certainly scored your Lucky Strike.