Seedy Parts of Town

“So if I get her to bomb this post office, you’ll let me cum tonight?”

It was a half-joke from Anon, but nothing—and nopony—answered him. Yet he knew the score regardless. This engagement had commenced too often in too many consecutive Canterlot nights. Past the blindfold he was wearing —and nothing else—he could see hints of moonlight blaring around the wooden posters and sills around this bedroom. Even though the room was deathly silent, he knew the pony incoming would only be heard when she wanted to, as quietly as she wanted to. And most importantly of all, despite Anon knowing he was in for some more sexual escapades this night… he knew the pony giving it to him this time was not Vinyl Scratch.

“Look, I… I just don’t want Vin to get into any trouble she can’t get out of.” Now that part was all-truth. Anon knew not the depths of this other mare’s obsession with Vinyl, despite their many nights of passion. Yet, it clearly drove her every movement, if she could so reliably steal him away from the musical unicorn.

Anon’s ears perked, almost mistaking the echoing noise for a mouse’s squeak. Yep, perfectly paced, yet almost inaudible; whoever this ‘Octavia Melody’ was, she was in the room.

She hadn’t given any orders this time, though. Not like Anon could follow them much anyways; the four bonds keeping him rooted to the floor were strong though cushiony around the hooves. Idly, he wondered how much such luxurious bonds could set a pony back.

Then, an ear-splitting crack rang near his forehoof, and all Anon could think about was doubling over and hoping his suppliance kept her from punishing him.

‘Ah-hem, dick of Anon,’ the green stallion thought. ‘Punishing. The bad thing. Not something you should be throbbing out of your stupid sheath for—!’

“Good.” Also, no voice that stern should be so sensuous, but Octavia defied logic as well as visibility. “At least you haven’t burnt all that energy on your pathetic stunt in that alley.”

Anon, despite himself, looked up definitely at the term ‘pathetic.’ Now that was far from pathetic! He screwed one of the most talented ponies in Equestria in front of all to see! Did that mean nothing to her?

It did, as he could feel a hoof curl around his cock, hard enough to stop the bead of pre at its tip from swelling further.

“By Luna’s crown, you’re getting hard at that thought?” Octavia asked.

Anon didn’t answer, not even when another whip-crack at the ground next to him tried to scare him. Rule number one: you stay silent when I’m touching you. Octavia’s past words thundered hard into his mind, and he obeyed by instinct.

“You think plundering myVinyl’s juicy… puffy…. insides is a notch on your non-existent belt? Hm?” Anon couldn’t even tell if Octavia was complimenting or castigating him. It was so deep, so inquisitive… and yet so titillated. “That this insolent little dick of yours is suddenly worthy of any mare’s private parts?”

Her hoof left, and Anon swore he could feel his shiver of relief shake loose a kink in his back. “I swear, Oct, I didn’t even know you hated that, I—”

“You think this is hate,” Octavia said. It wasn’t a question. “You’re not important enough to hate. You’re a pest. A question nopony asked, in being and in cutie mark.” The hoof stroking up that very cutie mark of Anon’s was betraying possessive thought, and Anon bit his lip trying to keep from pointing that out. “And how anypony can fit that obese, obscenely long shaft of yours in them boggles the mind.”

Anon’s shaking shoulders nearly tumbled his forelegs out from under him. Again, he knew the game—Octavia had shown she could just tease him all night and leave it at that. He wondered if Octavia wasn’t a musician herself; the way her hooves flowed over his coat certainly reminded him of a viola’s strings being strummed.

Then the sharper tap of a rubber lump against his plot made Anon’s sweat start up again. That was definitely a crop pushing against his ass, sliding up and down his cleft, pushing against his hefty cum-sacks.

“Oh ho ho ho…” Octavia purred. “Very plump today. Perhaps the report about your fatigue is inaccurate.”

He was not in the mood to see how many beats Octavia put him through as a ‘tune-up.’

Then he felt a wet, bumpy surface run against his rigid fuckspire. He knew it was Octavia’s tongue, and a moan burbled at the base of his throat—but no further.

“Your filthy cock has no right to taste like that.” Octavia smacked her lips as she drew back from it, once again dry but still achingly hard. “At least your mouth knows how to keep itself under control.”

“Now tell me how Vinyl—”

“D-don’t you already know? You snatched me from her, Celestia knows how you do it so silentl—OW!”

The crack of the crop against Anon’s flank was almost lightning-fast, but the pain seemed to last like an eternity. Especially since his bound hooves couldn’t stroke the skin.

“Really? Violating rule two?” All the tentative interest in Octavia’s voice was gone—it was now somehow colder than the air wafting in from that open window. “Repeat it for me. Now.”

Anon swallowed thickly, hung his head, and complied. “In this room, you are me almighty—”

Another slap of the crop against his other asscheek, and Anon howled helplessly.

“—Invoke. No. Other.” The last three words of that rule dropped from Octavia’s mouth like anvils. “Close your legs, and I triple the whips.”

Anon shot a glare back at Octavia that would probably be more effective if a black band wasn’t over his eyes.

“Oh. Have I incensed you?” Octavia’s voice was daring now. “Do you want to leave? Go ahead, I’m not doing this for your satisfaction. You know the safeword. You know where the key is.”

How Anon was tempted to at that immediate instant. Just to show Octavia that all this waiting and whaling wasn’t something he longed for at all.

“Leave, Anon. Do it.” The soft creak of springs told Anon that Octavia had taken up a perch on her mattress. “Maybe you can see how well you evade the guards when I’m not telling them to take breaks right after slapping you in holding cells.” And another whap ricocheted off his hip, the crop’s strike far lighter than the others but still throbbing lightly.

Anon’s jaw ground incessantly, but no ‘clef-note’ left his lips to make Octavia relinquish her crop. His head vibrated in irritation, but it didn’t lower to the box located between his forehooves. Even with his ass feeling toasty, even with his sanity bending, he did not break.

“That is what I thought.” Again the squeaks of springs sounded, and the flicker of shadow let Anon know that Octavia was circling to his front. The heady scent of her coconut perfume also let him know that Octavia had kept herself in control long before she’d retrieved him.

“Now. Tell me what Vinyl did today. Then count each of the ten hits you take for your impudence. Fumble a number, and I double the limit.” Her lips moved right to Anon’s ear, the sickly-sweet tone she took a complete contrast to the words that spilled forth. “Lie to me even once…”

Anon would not be caught unawares again this night. “... And I take triple the hits.” That was Octavia’s third rule, and he never wanted to see what would become of his poor posterior if he ever broke it.

Octavia only tsked in approval, right before licking a wet trail along the shell of Anon’s ear. At this point, his cock was fully unsheathed, and only a couple of inches from touching the floor. A shuffling of hooves let him know Octavia was ready to punish.

And with bated breath, Anon spilled the beans.

“I-I woke up next to Vinyl today in the s-same party hall we fell asleep in.” Not feeling the prickling pain of Octavia’s crop, Anon went on, cursing how his voice stuttered. “After a quick blow, Vinyl left for a spell. I-I think she popped by Saffron’s to get us some grub, I recognized her pepper flakes on the grilled cheese we a—holy fuck!”

Octavia’s first disciplinary strike was her bare hoof, clapping against his ass as his hindlegs buckled. His hips twisted, desperate to grind his glowering ass against the rug and soothe planes of irritated skin on his flank, but Octavia’s hoof wrapped around his hip and tugged sharply. Anon was back on all fours, and he eventually stabilized himself.

Then he remembered the other part of what he had to do in this confession.

“O… one….” Anon growled. To whatever extent that his dick has softened before, it was concrete-hard now.

“Good boy.” Octavia’s hoof stroked at his sack again, drowning the pain under a slow tide of bliss, then retracted her limb again. “Continue. You ate breakfast, and…”

Anon’s voice came out like cannon fire, hoping he could finish before more hits came down. “And then… we had to leave. Lemon Hearts’ birthday was yesterday, and they only rented the hall till 8 AM. So, I collected Vinyl’s pay, we strolled the streets until I saw a guard and we took to the—AH! Dammit, two!”

Anon swore he could hear Octavia’s smile as she paced behind him. “How cute. First sight of armor and you’re still a mewling little foal. Then what happened?”

”W-we were only roof-jumping for a little while, the theatre was nearby, and we took the chance to slip in—Shit-fuck! Three—And we saw a film, I don’t remember the title—Gah! Fourohfuuck~”

Octavia pulled out two more hits in quick succession, Anon almost driven to his haunches at the barrage. His ass was a sparking red now, and Octavia made no move to soothe his torment.

“Number. Now.”

“Fuckin’...” Anon’s head nudged at the box, stopped, nudged again, and shakily pulled himself to all fours. “Five and s-six.”

“You’re so close,” Octavia said. To orgasm or completion, Anon didn’t know. Arousal and anguish battled to a maddening standstill in his noggin, sweat made his fur stick against him uncomfortably, and his lips were becoming sandpaper. “Ignore the movie. What did you and Vinyl do after?”

“Make a trip to Cinnamon Chai… the pepper of Saffron’s sandwiches was getting to me.” Anon braced for impact. Still, nothing came for good or ill. “A-and we ordered cappuccinos. Vinyl started talking about what place we’d tag today, and—”

“And she didn’t even once ask where you’d vanished to?”

Every time, about the tail end of his confessions, this question was voiced. And again, Anon answered the same, his words as truthful as they were hoarse. “None after I gave that excuse.”

For a while, only Octavia’s breathing punctuated the din in that room. Then… “What does Vinyl hold over you? Besides the sex, what?”

“W-what?”

“Why does Vinyl trust your excuses so fast?” Octavia’s voice had risen to a shout now. “She must be holding out for something else, now tell me what it is!”

“I don’t know what it is!”

“Don’t you lie to me, Anon—”

“I swear, Octavia! She just… really likes doing stuff with me! Enough that she gives me a wide berth.” And then something curious fired up in Anon’s memory, something he pursued without thought of how the mare behind him would take it. “I mean, if you talked to her, I’m sure she’d come around to you just as well—fuckfuckFUCKFUCK—!”

Four hits, and yet each fell upon Anon like a hurricane. Now Anon was definitely on the ground, too stunned by Octavia’s sudden rush of strikes to even safeword his way past more hits.

It wasn’t a problem anyhow, as he soon felt a different heat press flush to his hip; Octavia’s center, the divide between her legs damp and winking as it slid against his skin.

“Fuck you, Anon,” Octavia hissed, her voice uncharacteristically savage and low as she ground her pelvis against his hipbone. “Fuck you for not even sparking an ohm of suspicion from my Octavia. Fuck you for popping into this world just as I was about to leave. This. Life. Behind.” Each word was punctured by a greedy roll of her hooves against his ass, along his fuckspire, down the dip of his spine. “And fuck you for making me wait until Hearth’s Warming to leave this post and fuck the memory of you from my Vinyl’s mind.”

Despite the fear he felt at Octavia’s words, Anon didn’t miss the somber sniffle that slipped from Octavia’s maw after. Apparently, his ears were the best at detecting Royal Guards from five meters away and tissue-light sniffles from dominatrixes alike.

“Octavia…” he breathed, unsure if it’d restart Octavia’s crop-striking cascade again. “Are you…”

Octavia’s weight left Anon at once, and he tensed, that safeword ready on his lips. But no such pain came to force the issue. Instead, he felt two sweat-dribbed hooves close around his head. With a trained, almost nurturing motion, Octavia guided the green stallion’s head to her center.

The second the billowing musk of Octavia filled Anon’s snout, he knew what was coming. Or rather, who; if he played his cards right.

“You still think you’re a stud, you whining foal?” Octavia said. “Then let’s see how your tongue serves yourhandler’s needs.” A tap of her crop along his spine and Anon jerked closer between Octavia’s thighs. “Suck.”

Anon’s tongue obliged. His first swipe along the mare’s folds brought another familiar taste to his mouth, more familiar than Saffron sandwiches and Chai coffee—and far sweeter. The tart taste of Octavia’s twat was like manna for his parched lips, and his ears were getting a treat too, thanks to Octavia’s feather-light pants.

He’d need to be far more daring if he hoped to make this overpowering domme undulate.

So Anon changed tacks. Nipping along the edge of Octavia’s pussy lips, he brought up his snout to flick lightly at her swollen nub. Octavia’s wet clit winked, spreading further around his wet muscle, and he suddenly longed for his forehooves to be free so he could wrap them around Octavia’s hips. He never really knew just how much he relied on his clumsy hooves in situations like this, not until they were bound fast to the floor. And at once, he hated and loved it.

So did his dick, as shown by the patch of pre-cum-burbling against his barrel.

And what luck: Octavia would afford him this one mercy for further closeness, so it seemed. Pushing up the box at Anon’s feet, Octavia opened its lid with her teeth, the tinkle of a falling key following suit. Soon after, Anon heard the sweetest of sounds, a pair of rasping clicks. Over one forehoof, then the other, the strain against his front limbs slackened to nothing.

Anon rolled his hooves and confirmed what had happened—the second cold air washed over his once-bound forehooves, he squealedhappily against Octavia’s folds. The mare hissed in response, her jaw clicking as she brought the tip of her crop against her upper lips.

Then, two green hooves locked around the mare’s hips, and Anon’s tongue took the plunge.

“Anon, by fuck!” Octavia moaned, hips closing snugly against the stallion’s head. “D-deeper!”

Her wish was Anon’s command, his tongue hooking and darting deep inside those velvety walls of the mare. Anon’s tongue was soon bathed in endless waves of sweet juices, the pain he’d undergone now a ghost of a memory. His teeth playfully ground against the clit he was busy plundering, the spongy squishingof her fold sending a liquid thrill through his body.

Octavia’s hips were jutting into his snout, clearly wanting to ride Anon’s face but still possessing a fast-dwindling resistance to it. It wouldn’t take long for orgasm to bowl her over regardless, the tell-tale shudder of Octavia’s walls around Anon’s tongue a testament to his work. Her back arched in preparation, her body tight as a bowstring as her every muscle strained.

And then it was over: the mare’s bliss crescendoing in a flurry of “Fuck me, fuck me hard, fuuuuck!” and lolling tongues and white-hot pleasure spiderwebbing across her vision. Octavia's cum—far more than the small offerings slipped past her pussy walls before—sloshed over Anon’s lips and down his eager gullet. If Vinyl’s climax was known for its force, Octavia was distinct for its taste.

But far too fast, that heavenly fountain was yanked away from Anon’s grateful lips. And the power of Octavia was soon on full display as she pulled Anon up into a harsh kiss, her tongue dominating his mouth instantly. Before Anon knew it, Octavia’s hooves had slacked the bonds around his back legs - but only enough to push him into a sprawl-eagled position on the bed.

“O-Octavia, what in the world’s going—”

The shuddering rasp of another pair of closing cuffs rang out, and Anon’s forehooves were again struggling senselessly against the posters of the bed they were tied to. At least his body was in far softer recess now, the satiny feel of the blankets under his back and sore rump long-awaited. His breath came out in pleasured pants as he ground his ass against the sheets at last, the pain now like tantalizing sparks in the kindling of his lust.

Then, the mattress dipped tellingly, and Anon knew his work this night was far from over.

“If you cum before I do this time…” Anon could feel the sauna-like heat of Octavia’s drooling slit as it spread over his stallionhood’s head. Right before another telltale click brought another familiar—and frightening—pressure wrapping against the base of his erection. “That stays on until daybreak.”

Anon nodded feverishly, unsure of anything but the need to feel her sodden slit slip like a glove around him. Octavia wouldn’t leave him waiting long, bracing her hindlegs over Anon before sinking onto his lap with an ear-ringing plap.

A bestial how echoed over the room, and the fact that Anon couldn’t tell if it was just his voice or Octavia’s only made it hotter. It’s been proven many times in their secret past, but now above all, being deprived of his senses made moments like this as uprising as they were sensual. He could feel the strings of Octavia’s juices oozing over his lap, the warmth and scent sending his nerves into overdrive.

To hell with what he’d thought before! Fucking Octavia was just as amazing as Vinyl.

Both ponies started moving in seconds, Octavia bracing her hooves on her chest as she moved up and down in tune with his thrusts. With the orgasm he’d been denied all night, Anon was suddenly a little grateful for that ring—spewing his load inside this gasping mare would have been far too fast an end to this night. Would that he could be in a thousand deals with this Canterlot handler if they all were as erotic as this one.

It would only be for a little while, though—especially with what he heard next.

“Damn it—fuck yes—that hits the spot,” Octavia hissed, grinding her hips hard against the thick dick spearing through her folds. “Ruin me, you fuck, ruin me—”

Anon certainly tried to, his hips ruthlessly slamming against her as the springs creaked under them. Her pussy was unrelenting, wringing him like a dishtowel as she cursed him and begged him to never stop, all at once. His response was a series of inchoate wails, lust striking more of his vocabulary from his mind by the second. Octavia was a world apart from Vinyl, and not just in her government role; control was indeed everything to this mare.

And she showed how rousing it was with each hop, her cunt working Anon’s cock to perfection.

But despite the lightning storm of lust ravaging Octavia’s body, despite Anon squirming needily in his bonds, it seemed one final thing would be refused during this steamy night. It was starting to scare the green stallion, feeling his dick swell needily around the ring holding back his climax. Octavia’s voice was getting shriller, too shrill for him to be certain that she’d remember to release his seed.

Would this be how today ended? With Octavia so fuck-drunk that Anon went mad with the deprivation?

Almost immediately after that thought left his bliss-baked mind, Octavia moved to his hoof. Despite how the night started, this time Anon had never been more grateful to feel her hooves around his cock.

“You’ve been so good today, pet,” Octavia growled, her voice a whisper. It was almost muted by the sloshingof their sticky hips clapping together. Anon didn’t even know it could get that… gentle. “Do you want to fill my womb n-now? Is that what you’ve been waiting for, Anon?”

Anon could not lie to Octavia, not if he had the strength above his groin, too. He nodded frantically.

“Do you want to try and knock me up, like you did my Vinyl?”

Another nod.

“Do you want to punish me with your seed, for all the times I punished you tonight?”

Once more, Anon silently concurred. It felt like a volcano behind his stimulated shaft, his balls had to be the size of beach balls now, he was going to lose it—

A snip rang out, and suddenly, bliss supercharged his sweaty body in a millisecond. The broken band of leather pooled around Anon’s thighs, and almost before Octavia’s words came down, he howled in wanton lust.

“Well, since you’re so desperate—” Octavia crashed onto his lap in one mighty motion.

Mt. St. Anon erupted at last. His cock blasted rope after river after riptideof burning spunk deep inside Octavia, the lewd feeling making his blindfolded eyes roll in his skull. That pearly goo oozed to around his stallionhood, inside her womb, and around every nook it could find. Eventually, that opening had to be found outside of Octavia’s cunt, spurting out in dollops over Anon’s thighs and flanks.

And just as Anon thought that this was it, the peak of overwhelming bliss, Octavia’s walls became suffocatingly tight around his prick as she came again. The mare’s cunthoney sprayed out in fan-like bursts, pressurized by the dick still jammed up her pussy walls. Anon’s back arched at the feeling, almost as if offering to catch Octavia’s sap as she writhed and shuddered over him.

Alas, the twitch from Octavia’s afterglow gave way to a timber, tumbling bonelessly next to Anon as his fucklog slipped out of her slit. The soft wheeze of the pillows billowing under her form blew cold air over Anon’s sweaty face, a sensation he sighed merrily at. Oh, everything was going to sting like hell tomorrow, but this was definitely worth all the whipping and waiting.

“Hmmm….” Octavia’s breath washed over Anon’s face, her words still striking deep into his soul despite the hoarse tenor behind them. “Perhaps… this assignment of mine may be worth all the times it keeps me from… our Vinyl.”

If Anon wasn’t currently in a positing where his head would not be vertical to the ground, he was sure his jaw would be plowing through it, now. “I… guess I’m happy to help.”

Octavia let out another breathy sigh. When she spoke again, her voice was back in its authoritative tilt. “No. You’re happy to cum. You’re happy to fuck. You’re happy to make me sweat and swear and shatter under your big, bitch-breaking, marefriend-stealing tool.” She licked another trail over his ear. “And this little cat-and-mouse game staying ever in your favor? It depends on how long you keep me happy about that as well.”

Anon gulped, but nodded, understanding just what this moment was being done for. Octavia was raw, passionate, and experienced beyond any non-alicorn he’d met in this town. But it all predicated on maintaining control, slippery as the grip was. And he would not ruin that.

“I understand, Octavia.”

“See that you do during our next meet,” Octavia said. “I would hate for my reports to Luna about your talents to get more… accurate.”

Anon’s mind bristled at the thought of that. Then his ears perked in shock. “Wait, our next—”

“You tried to tag Jet Set’s house tonight. He had several Diamond Dogs guarding it this time, learning from his fiancee’s previous graffiti troubles. You got caught in a gate, and they got some scratches in. Do I need to repeat myself?”

Anon again understood. This was not just for his ears; Vinyl would still need to be kept in the dark about some things, same as him. “Yes.”

“Good.” Octavia’s hoof stroked down his cheek affectionately. “Rest. And if you’re good tomorrow, the blindfold might come off for the first time.”

Anon couldn’t help but jump for joy on the inside, and not just because of Octavia crawling over him, his face right up against her pillowy chest fluff. He wanted to pinch himself, but even if he wasn’t suffering from a severe lack of fingers, this was one thing he never wanted to wake up from. Even as oblivious began its ironic climb upon him from this thought, he knew that no matter where they opened, he would be in no serious harm, thanks to these two special mares known as Vinyl and Octavia.

Anon would be safe.

And thoroughly sated, no matter if he was giving or taking.