Happenstance

True to my earlier suggestion, Octavia grabbed me by the tie and dragged me through the lobby behind her, presumably to her room. It wasn’t the cute kind of dragging you’d see in movies either. You know what I mean? The kind where the feme fatale gently leads the dashing protagonist by the collar in a show of dominance? Nothing like that. In fact, if the excitement to get to our destination wasn’t driving my legs to keep up with her lengthy stride, I would likely have been strangled.

Down the halls we went to the elevators, drawing glances from the few ponies still wandering the hotel this late. Most just sneered at the obscene display, but one guy winked and gave me a thumbs up.

Thanks dude.

As soon as we boarded the empty elevator, my captor whipped around and drew me into a ravenous kiss. Instead of leaning over slightly to reach me, she decided to use her ridiculous strength to bring me to her. I struggled to keep a toe on the ground, but my weight rested solely on her surprisingly strong arms.

I might have felt emasculated had we not been in the middle of swallowing one another’s tonsils. As it was, she could have bridal carried me down the hall and I would have happily thrown my arms around her.

The elevator dinged behind us, luckily on our floor and not in front of some unsuspecting bystander. I’m not saying we would have stopped if somepony else walked in. I just would have felt a little bad.

A short walk later, I found myself thrust against her doorway. I don’t know where she kept her key card, but I doubt she managed to find it in her purse one-handed. Either way, she brought us both in and slammed the door behind her.

I got a chance to look around when she threw me into a seated position on her bed. It looked like my room but with a bigger bed and without all my clothes sitting in a pile around a suitcase. What size beds do ponies have? Earth pony sized? Was there a princess size?

My new bedfellow tossed my tie aside and crawled onto me, making bed sizes seem very uninteresting. She stopped inches away from my face, giving us both a moment to catch our breaths and stare at each other.

Neither of us said anything. We just sat there panting on one another. I mean, what could we say? “That was nice. Let’s keep doing that.” “Yeah. I sure do want to have sex with you.”

I actually managed to contribute when we once again brought our lips together. And thanks to the bed, I finally had a chance to explore her without holding on for dear life. I almost felt bad running my hands through her mane, but I’d do it again. Soft, smooth, and not a single knot. I wasn’t too familiar with horses back home, but I’m fairly certain they didn’t feel like that.

Wandering downwards, I traced my hands along her neck and shoulders, squeezing where I’d imagine ponies built up tension. They didn’t quite feel like the muscles of someone who’d just held me against the wall.

My mouth descended as well, leaving a trail of nips down her jaw to her neck. It was strange. I could distinctly feel a pleasant fuzziness from her fur when I caressed her with my hands. Yet I felt nothing but skin as I kissed it. A blessing, I suppose, seeing as I wasn’t getting hair in my mouth.

I must have been doing something right if her gasp was any indication. I wanted to hear it more. However, my hands met only the comparatively rough texture of her dress. That wouldn’t do. I fumbled around for a zipper and hoped she wouldn’t mind if I undressed her.

That’s when I realized my coat and shirt were entirely unbuttoned.

“So many layers,” she grunted in annoyance when her hands met my undershirt and not my chest. “Were you cold?”

I didn’t get a chance to answer. She pushed me back against the bed and straddled my waist, tugging at my remaining collar with a finger.

“Off,” she commanded.

“Yes’m,” I replied meekly. There wasn’t much force behind her words. If I had only heard her, I might not have been so intimidated. It was her face that really did me in. The mussed mane, the lightly clenched jaw, and the hunger in her eyes made it very clear who was in charge.

I shed my unbuttoned garments and struggled to pull my undershirt over my head from my pinned position. When it finally passed over my eyes, I found Octavia already out of her dress and fiddling with her bra behind her back.

I was all too happy to see the gown go. Sure, it showed off her curves and legs, but I was ready to see more. And boy was there more to see. Proportionally, her breasts seemed larger than average. I’ve never committed to memory what cup sizes looked like. However, when you factor in that she was just bigger than me in general, those things were nearly the size of my head.

And then the bra joined the rest our clothes on the floor. Now, I’ve heard plenty of people throw around “I could die happy” when something nice happens. I never got that. I always thought that if I saw something that gave me that much joy, I’d want to live as long as possible to keep seeing it.

Let’s just say her chest made me consider exercising and eating healthier.

It took all the strength I had to push her onto her back. Or try to anyway. She drew her arms back to support herself while I slipped out from under her to grab at her newly exposed breasts. I heard her giggle as I licked along the gray flesh to reach a charcoal-colored nipple.

“Mmn,” she hummed, coaxing me deeper into her chest with a hand on my head. Her other hand crept down my back to grasp my bottom. Then, with a particularly firm squeeze and a flex of her arm, I was pulled out of her cleavage and up to her face.

She gazed through me with half-lidded eyes, chewing her tongue.

“That’s nice, Anon,” she began, now with both hands groping my ass. “But I’d like to see the rest of you now.”

Oh yeah. I was still wearing pants, wasn’t I?

She moved her mouth over to my ear. “These are getting in the way. Don’t you think?”

Then she bounced me against her, letting me feel some pressure between my legs up to the small of my back. Pressure that was very clearly not exerted by one of her first two legs.

It’s not that I forgot about it. It just didn’t cross my mind again after she pulled me out from under her dress. But now it was crossing my crotch as well as a good portion of my back. I briefly wondered if I’d gotten in over my head.

That uncertainty didn’t stop me from undoing my belt. And Octavia didn’t seem too perturbed either. As soon as there was nothing keeping them on, my remaining clothes were all but torn off me, sending me back onto my back with Octavia’s other leg springing up between mine.

I’ve seen them before back home on the closest thing we had to these ponies. I considered them about as much as I’d consider any farm animal. But seeing it jut proudly from the most beautiful creature I’d ever seen? I could do nothing but admire it in that moment.

It must’ve been longer than my forearm and a bit thicker too. Over a foot of cock the color of her mane sprouting out of a hefty sack housing two apple sized testicles. It extended from a deeper gray sheath at her pelvis, widening a bit around her ring less than half way up, and flaring ever so slightly at the tip. Though, if I remembered correctly, that particular area could get considerably bigger under the right circumstances.

My hands moved on their own, reaching out to caress the monstrous member in front of me. Christ, I couldn’t fit my hand around it anymore. She must not have been fully hard in the lobby.

My fingers glided along her flesh exploring the ridges along her tip and ring. The shaft was completely smooth save for a few oddly visible veins. I swore I could feel her heartbeat when I pressed on them.

I moved one hand up to massage her tip with my thumb while my other hand traveled down to fondle her sack. For some reason, I thought it’d feel more like leather. But it was about as smooth as her skin.

Then I tried to lift her sack and promptly dropped both it and my jaw. That thing was heavy. Even though I knew it wasn’t their function, I couldn’t help but imagine them being filled and sloshing with the slightest movement.

Then I imagined myself draining them.

As if on cue, a dollop of clear fluid oozed from her tip onto my thumb. I couldn’t find anything out of the ordinary with it. Aside from the volume, of course. That single drop was enough to nearly soak my hand.

Still staring at her cock, I absently brought my wet hand to my mouth and tasted the fruits of my labor thus far. Slick, warm, but not much taste to it.

I licked my fingers a little more. Yup. I could barely taste it.

Why did I feel thirsty all the sudden?

“Goodness,” Octavia sighed above me. I tore my attention away from her cock to find her biting her lip.

“That’s…” She trailed off. “Could you-?”

I didn’t wait to hear the rest. I pulled her with me as I scooted back to the headboard. She ended on her knees, straddling me once again. Only this time, I had full access to her cock.

That thing wouldn’t be fitting in my mouth. I’d have better luck fitting my fist in there wrist first. Still, I took what I could get and set about licking the head.

Octavia gasped and rewarded me with another release of pre onto my tongue. I lapped it up while my hands pumped the rest of her shaft.

Alright, I was wrong. There was definitely a taste. Hell if I could describe it, though. It lasted only an instant on my tongue before it dissipated. I needed more.

But she would not provide more. I slurped and stroked all I could, but her cock wouldn’t throb again to feed me. Switching methods, I brought my head down to her sack and licked for all I was worth.

She still wasn’t throbbing, but I took her moans as encouragement enough. I traveled upwards, dragging my tongue from her sheath to her ring and savoring all the textures in between.

I could smell her now. It was almost like her taste before.

Again, I dug my nose into her sack and licked upwards, having trouble inhaling and tasting her at the same time.

The sensations got to me, making me lose track of just how long I’d been servicing her. I’d forgotten about getting more pre out of her, content to lick and smell and savor.

Up and down. Up and down. There wasn’t a spot I didn’t touch. That I didn’t cover. It was alleviating my thirst, though not quenching it. I would’ve been happy to continue like that all night.

Octavia, however, wouldn’t.

“I-I’m sorry, Anon,” she said, pushing me back. “I need you.”

And I need you dammit now give me back your-

She reached over to her bedside drawers and produced a bottle with a white label. She popped the cap and squeezed its contents into my still-outstretched hands.

Lube?

“Please help me with this.”

Could she be…?

My hands were back on her as soon as she moved closer, sliding now much easier over her flesh. My mind continued to ask questions, but my body had already made its decision.

“Th-there’s no way I could- oof!”

Octavia shoved me down onto my back before I could finish, looming over me while I continued to lube her cock.

I glanced back and forth from her engorged member and her crazed expression. Her mane fell around her head, encircling her face. Dim light from her bedside lamp filtered in through it, casting heavenly rays around her.

“Octavia,” I panted. “I can’t-ngh!”

She didn’t want to hear it, reaching a hand down between my legs. Between my cheeks.

“It’ll be fine,” she assured me. “You’ll love it.”

I felt her lubricated finger enter me. I opened my mouth to cry out, but she just covered it with hers.

Although I was being assaulted on both ends, my hands wouldn’t leave her cock alone. The cool lube had warmed considerably on her as I spread it everywhere. Her finger was already more than I was used to. How the hell would I fare against this thing?

When it throbbed again in my hands, I realized I wanted to find out.

Octavia thrust her finger in and out of me, unaffected by my clenching. When I finally did manage to relax, she added two more.

I started to hear it. Wet slurping sounds from below to accompany her moans into my mouth and mine into hers. Despite my discomfort, I couldn’t deny that I was enjoying it. The way she stroked and prodded places I didn’t know I had just made the pain disappear like magic.

Like magic?

I’ve seen some weird stuff here. Like ponies floating around, floating other stuff around, turning into crystals and back like it was nothing. What was so farfetched about a big cock in a little hole? Or weird super lube? Maybe I really would be fine.

Octavia withdrew her fingers, seeming satisfied with her work of mapping out my ass. As she drew back her head as well as her cock, I began to feel woefully empty. My hands grasped at nothing. I needed her back.

She seemed to sense my hunger, lifting my legs and moving herself into position. I did my best to hook my feet together around her, but I couldn’t quite reach. Luckily, she had no shortage of curves on which I could rest my legs.

She dragged her cockhead along my crack, either teasing me or waiting for it to catch on an entrance.

No way. Magic or not, she’d need to do some guiding to get anything done with that thing.

While she grabbed her shaft to aim, I did what I could to spread out more for her. Although, once I felt her massive head against my pucker, I realized she’d have to do most of the spreading.

“Are you ready?” she breathed with a lick of her lips and an experimental prod against me.

“Fuck me.”

She pressed gently against me, showing restraint I greatly appreciated. It felt more like I was being poked with a baseball bat than penetrated. However, Octavia was insistent and had more than enough strength to back it up.

Her free hand gripped my thigh tighter and gradually increased the pressure of her attempted thrust. Slowly but surely, I began to open up for her.

Octavia growled at my resistance. She wanted in and I couldn’t get her there fast enough.

It hurt. Only slightly at first, but the pain grew with every additional stretch. Sharp jolts followed by dull aches. She was certainly slick enough, but friction wasn’t the issue.

Just as the pain grew alarming, her head popped in. I gasped, feeling some tension leave my gut. She was in.

“Okay?” she asked shakily, moving her guiding hand back to my thigh.

I glanced nervously at her hips and how far away they seemed. I had a lot more left to take. Then I saw beautiful face that had drawn me in before twisted in ecstasy.

“More,” I whispered.

Octavia sighed with relief as she pressed onward. Her tensing arms and shaky grip told me how much she wanted to force herself in, but she held back for my sake.

With her head inside, my ring had comparatively little trouble swallowing her smooth shaft. Though, I felt a new pressure in my gut as she dug deeper than anyone was meant to go.

God, she was endless. I was already acquainted with her girth, but she had every intention of introducing me to her full length in this one drawn out thrust.

And what a length it was.

I couldn’t deny my own pleasure beyond the background of pain. There was something about engulfing that big club between her legs that was so satisfying. A large part of that may have been her cock rubbing a spot within me I’d only really considered in textbooks.

Octavia leaned in, now hovering over me for more leverage. As she moved her hands to my waist, I hooked my own arms around her neck to draw her closer.

The change in position forced her cock deeper. It hurried forward, only stopping at her ring when my unprepared ass denied it.

“Nhh,” Octavia grunted, wiggling her hips. “Anon…”

My grip on her tightened in every respect. My nose dug into her neck while my heels pressed against her back. Among the ever-growing aches, I worried more and more that I really couldn’t take her.

“Oc-ngh-tavia,” I whined through winces.

She didn’t respond, still grinding into me and coaxing frustrated throbs from her cock.

“You’re so-oh! So big! It’s too-ooohh!”

My pleas devolved into gibberish under the overwhelming sensations. I didn’t know if I was close to climaxing or splitting in two. Or both.

Seemingly defeated, Octavia began to retreat, once again dragging her throbbing cock through my insides.

“S-sorry,” I stammered as her cockhead approached my entrance in reverse.

I received no response, save for a trembling inhale above me. She squeezed my hips and shuffled on her knees.

Oh no.

“Wait! Oc-!“

In an instant, she sheathed herself up to her ring within me. My words died in my throat as she again failed to overcome my resistance.

Pain this time. Sharp and burning. I couldn’t stretch fast or wide enough to accept her. Yet, she continued to make her offer.

Again, she repeated her retreat and thrust, drawing agonized cries from me.

Again.

I raked my too short nails across her too tough back in desperation.

Again.

Every part of me was shaking.

Again.

“Please, Anon!”

Again.

It hurt.

Again.

Too much.

Ag-

Or not. Despite my feeble bracing for another thrust, I didn’t feel her move. Just the rise and fall of her heavy breath atop me. That and the lingering pain.

Octavia didn’t give me time to contemplate my situation too much, grabbing my chin and pulling my mouth to hers once again. It wasn’t an assault like last time. In fact, it was the gentlest she’d been with me up to this point. A meeting of lips instead of a devouring.

Our tongues met on equal terms, cordially slipping by one another. As I savored this fresh sensation, I found her taste once again. The elusive scent and flavor I’d witnessed while I’d serviced her cock.

I still couldn’t place what it was even though it lingered longer this time. Nearly sweet. Nearly sour. Nearly everything, really. A taste I’d never experienced before.

But not just a taste. A soothing sensation spread through me from her mouth. For some reason, I knew it was the same as the taste. The feeling. The whatever. All I know is that the whatever rapidly replaced all the pain.

Octavia thrust her hips forward once again, though slower this time. I had time to savor the entirely pleasant sensations before I reached her ring.

She pressed onward and I readied myself for agony that never came. I felt pressure, sure, but nothing like the tearing of before. I’d liken it to the feeling of cracking a joint. You push it farther and farther until it eventually-

“Oh…” Octavia moaned as her hips met me with a slap. “Oh Anon…”

My mouth hung open in a silent cry. She was in, every bit of her. Pelvis against me with her heavy sack resting on my tailbone.

I came right there.

My body couldn’t process what happened, finding the flood of feeling far too much to handle at once. So, it replaced every sense I had with overwhelming bliss.

My own cock twitched and throbbed, releasing wildly on my abdomen. I idly noted that I hadn’t even thought about my own sex, much less touched it, throughout this whole affair. And it was already the greatest pleasure I’d ever experienced.

I saw that Octavia wasn’t quite there yet from the longing in her eyes. Still, she seemed just as happy as I was that she managed to hilt in me, giddily grinding her hips against mine. God, every time she wiggled, she pushed me back to the brink.

“Nnh Anon! I need to move again!”

I mumbled an affirmative, surrendering to my lover’s desires. Although, I don’t think I had much choice to begin with.

She pulled back with delectable slowness, letting my orgasmic twitches massage her. She freed maybe an inch or two of her cock before plunging back in, setting me off anew.

“Mmm. You’re squeezing so much!” she cooed in my ear.

“C-can’t stop!”

Octavia pushed against my shoulders, prying me off her to beam at the mess she’d made of me.

“Anon!” she laughed. “You came?”

“Cu-huh-ming!” I corrected, partially cut off by her next shallow thrust.

She dragged a finger along the modest puddle I’d left on my stomach and sucked it clean.

“Good,” she mumbled, grabbing my legs by the knees. “Keep cumming for me.”

As Octavia pushed away my only remaining hold on her, the Amazonian mare loomed farther and farther over me. A few more thrusts later, I found my ankles alarmingly close to my ears. Of course, I wasn’t too concerned with this in the throes of my prolonged orgasm.

There, with all the leverage and dominance in the world, she still wouldn’t even pull out to her ring when she thrust. Instead, she kept with those short, gentle pokes while peppering in a few hilted grinds just to tease me. Given her needy tone before, I had expected her to pound me as wildly as possible the first chance she got. But now it was like she was deliberately edging herself inside me.

I suppose I couldn’t rightly call it teasing if I was cumming all the while.

The constant exertion was taking its toll on my tired eyes. The human body wasn’t made to last this long if my dry ejaculations were any indication. Yet, when I looked up from the breasts bouncing before my face, I saw Octavia sporting the same blissful smile she had when she first squeezed into me.

My pleasured convulsions grew less frequent as my stamina waned. My lover took notice.

“Anon,” she complained, pouting at the loss of her constant massage.

Octavia reared back to her ring and launched back in, slapping my ass with her sack and my face with her tits. My body rewarded her efforts with more pulsating tightness while my cock resumed its steady throbbing. Her rod responded in kind.

“Oh yes, Anon!” she cried. “More!”

And more she would receive. Her new pace had me squirming and moaning all over again. However, as my pleasure reached another stellar plateau, I began to worry. If those little pokes had kept me going this long, what could she do if she tried?

I closed my eyes and took in the scene. I lay pinned to the bed in a mating press beneath this big beautiful mare spreading my legs and stretching my rear without even trying. If this wasn’t what nature intended for me, then she wouldn’t have made it feel so right.

“Am I boring you?” Octavia asked with a hint of sarcasm.

My eyes fluttered half open to peer at her grin beyond her breasts. I wanted to offer my compliments, but my ability to speak was long gone.

“I suppose I’ll need to pick up the pace,” she mused, grinding into me. “If I want to keep your attention.”

Oh god yes.

Flexing her hips, my lover dragged her cock back out of me, hesitating slightly once she reached her ring. The rigid flesh popped out of me without much complaint on her part and only minor whimpering on mine. I had more to say when I reached her flared tip, finding the cold emptiness that replaced her member unbearable.

I grunted, managing to squeeze around her beyond my involuntary spasms. Her cockhead prodded experimentally against my resistance only to relax and remain inside.

“You don’t want me to leave, do you Anon?” she teased. “Well don’t worry.”

Her hips dropped onto my ass, hilting her cock in me in one delightfully swift motion.

“I’m not going anywhere.”

The slapping, the stretching, the satisfaction of feeling that glorious cock glide back into me. I wanted to feel it again. And boy would I ever.

Octavia proceeded to lift her hips and fall back again, leaving little time between thrusts for me to adjust. Although I didn’t feel completely full or empty for long, the constant movement let me appreciate the lovely textures rubbing and massaging my prostate.

Over and over she pushed and pulled on my insides, filling the room with the erotic squishing sounds of our sex. And with the elevation of our passion, I somehow felt even more elevation in my pleasure.

I’d been at what I thought was the peak for so long. Yet here Octavia sat, driving me to greater heights with each savage thrust. I could only hope she was feeling a fraction of my satisfaction.

“Mmf! That’s it darling! Gods, you’re incredible!”

Finally, she was showing some sign of fatigue. It’s not that I wanted her to stop. I just wanted to get started on all those orgasms I must have owed her at this point.

And maybe I wanted to feel her cum.

My jaw fell open as Octavia added even more strength to her thrusts, letting my tongue loll out and latch onto one of the breasts smothering me.

Above, my lover seemed to lose her composure again. She wore the same overstimulated expression that I must have had, tongue out, mane wildly mussed up, and eyes very nearly in the back of her head.

Damn I’m good.

I half-giggled and half-whimpered up to her, hoping she’d understand my wordless beg.

“Oh soon, love! So bloody soon!”

Her measured full strokes gave way to wild, short thrusts deep within me. She was on her final stretch and seemed intent on making me remember it.

While her crotch collided with my ass faster and faster, I felt a pressure building up in me beyond the throbbing cock rearranging my insides. It hurt even through the magic her hilted rod had worked on my stretched hole. But I wanted it this time.

I screamed as the feeling grew. This climax among climaxes. The ‘little death’.

“Yes! Anon!” she howled back. “Take me!”

I flung my hands to her hips, frantically searching for a hold to pull her closer. Though, my feeble strength could do little against her onslaught.

Fortunately, her arms must have given out as well as she fell onto me. There, crushed under her full weight, suffocating under her tits, and at the mercy of her thrashing cock, I found paradise.

Octavia froze, bottomed out inside me and clutching me like I was her last link to this world. A guttural moan grew in her throat as her cockhead flared in my depths. Stretched anew and reaching my final peak, I moaned along with her.

It throbbed again and again, seeming to swell and shrink significantly with each ecstatic convulsion. My own cock followed her lead, twitching in time with her.

Our moans harmonized when I felt the first pulse of her cock. With her flare spreading me wide, she was free to pump her molten love into me without fear of losing a drop.

Wet warmth exploded in my gut, rushing to coat the remaining parts of me her cock somehow couldn’t reach. As her molten love coursed through my body, so did her taste. Her scent. Her touch. Her. Her. Her.

Octavia dominated my senses, each pump of her cock only renewing the fabulous rapture she’d bestowed on this mere mortal. ‘More!’ my soul cried. ‘More Octavia!’.

I heard her sob into the pillow next to mine, perhaps feeling a fraction of my delight. But it was enough to keep her throbbing and gushing into me.

I hadn’t noted any deformation of my stomach during our affair. No imprint of her member bursting out of my abdomen or chest if I were to consider her size. However, no inexplicable pony nonsense could hide the voluminous load this mare was producing.

When her cum overcame the resistance of my body, it offered a choice: make room or lose it. Naturally, my stomach readily expanded to accept the flooding embrace of Octavia’s spunk.

No. Spunk wasn’t the word. Spunk is gross. Feeling it warming and stretching my core, I could only call it nectar. Especially thick, viscous, heavenly nectar.

I still couldn’t see my stomach, but I felt it press more and more against Octavia’s as she continued to pump into me. Her soft fur brushed and tickled my ballooning belly.

Over and over, throb after throb, load after load. I grew until I was more Octavia than Anon. I swore I could hear the groaning of her member as it filled me. But even the impressive flare of her even more impressive cock couldn’t hold back the torrent she was building in me.

It began to leak. Slowly at first, with a thin stream escaping her cockhead’s seal through the path she carved out within me. It grew each time she released another jet into me until I heard it splashing onto the bed.

It pained me to waste her precious load, but what could I do? There was far too much for me to hold and she showed no sign of stopping. Hopefully she never stopped.

As I lay there drooling, I felt my earth shattering pleasure give way to earth shattering fatigue. Octavia had already gone quiet, her weight resting limply on my body. Maybe she was asleep already, despite her ongoing orgasm into me.

Would she pull out when she finished? Or would she just stay where she was, stuffing me with her flaccid cock? What if she just kept cumming in me all night?

It didn’t matter. My tired mind was slipping away, content to leave my body crushed under this beautiful mare until morning. Though, I had one more stray thought before sleep took me. One rather worrisome question that’d be answered when I woke.

What if she wanted to go again?