Eyes on the Prize

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This specific Friday had followed the weekend formula to a T for the Mayor’s office. The office work had been stopped up by a few days, and it was up to a few critical members of the office to bring everything back into order for next week. It was quite the shocker that this small town could get up to so much.

The papers from the Monday before lay squashed under piles of reports and requests. Anon’s hand flashed across the soft parchment, using the quill he’d been given to quickly sort through the mess. See, while it was really supposed to be “a few critical members”, the numbers quickly dwindled. A barrage of excuses and promises of repayment led poor Anon into this situation. Though the office comfortably employed dozens of people, the Fridays left the place in darkness, save for one sole light above a shiny green head.

Another stack of papers smacked against the pile, seemingly clambering to eventually overtake him. He stopped scribbling on the papers he’d been rushing through to look up to the messenger of his demise.

“Derpy just came by, late as usual.” The voice was commanding and smooth. The Mayor wasn’t one to be looked down upon. Her long grey hair was a testament to her experience, yet you wouldn’t be able to guess her age if you looked at her wrinkle-free face. Her lightly tanned skin hadn’t withered in the slightest, and most surprising, her soft blue eyes didn’t seem the least bit fatigued, despite being half of the workforce there that night. The other half frowned slightly, his forehead creasing appropriately.

“Of course. I expected that from her,” replied Anon, slipping papers from underneath his quill into the folder they needed to be in. He placed the folder to the side, then sighed deeply, placing his chin in his palms to rest. “I’m sure I shouldn’t ask, but how’s your work going?” It was quite dark, but he knew his boss’ face well enough to know she was closing her eyes.

“About the same as you,” she said, crossing her arms over her now ruffled top. He could remember seeing her in the morning, dressed for work, but her attire getting more chaotic was another staple of Friday nights at the office. “You seem to be moving a bit slower than normal, though. I expected you to be out of here soon.”

“I guess it’s just a slow day for me,” Anon said with a chuckle. The Mayor hummed to herself, seemingly thinking something over.

“I suppose you need a motivator, then?” Her eyes drifted sideward, where a bright alarm clock was positioned on the wall of the office. The time was 7:30, printed in red. “If you finish quickly enough, I wouldn’t be too opposed to you joining me for dinner.” Anon raised his brows in surprise. This was quite a deviation from the normal schedule. Throughout his time at the office, he’d never seen the Mayor invite anyone out to eat. Not even the more senior members. He averted his eyes from hers and offered a shaky laugh.

“Erm… to be honest, I’m a bit shocked,” he answered. “I haven’t been here that long. Why invite me?” The Mayor chuckled, tapping her chin and looking up as if searching for an answer herself.

“I’ve been meaning to reward you for your constant work, so it’s really my treat.” She pressed her fingertips together. “So, it’s like repayment. I really would appreciate it if you took me up on this offer.”

“I-I’d be glad to...” He still had his reservations, but Anon pulled the next stack of papers from their folder, then began reading through them. “I’ll get these done in no time, Mayor.” He could hear a faint chuckle before her heels clicked against the floor, and she walked away.

“Then I look forward to our outing.”

The clicking went away into silence, as Anon was left to sit alone within it. His hand had stopped by now, and his face was down where he could hide it fully. He took deep breaths trying to calm his body down.

By all means, it’s not unnatural business practice to invite a subordinate out to eat, and Anon knew this. But it was something about the way she walked, something about the class she walked with. Anon bit the tip of his feather quill, tapping his foot quickly against the floor.

Was she interested in him?

Even thinking that sentence was enough to debunk it, surely. But… he couldn’t stop his fantasy from running a bit wild. A cataclysm of “what if”s poured from his mind, the idea of thrusting himself over her naked, willing body and giving her a night she would remember to the grave crossed his mind over and over, scenario after scenario.

By the time he’d finished, his foot was tapping enough to play the fastest drum solo. He was lucky to be wearing his work pants because he was sure that anything he had at home wouldn’t be able to stop his Dwayne from poking right through the fabric to say hello.

“What the fuck…” he whispered to himself, slapping his head on either side before shaking it viciously. “I gotta hit the spank bank when I get home …” He pressed the quill back against the parchment, scribbling on the parchments once more, the thought he’d pushed back never truly leaving for good.

“Are you ready to go, Anon?”

Anon had been strapped in for the better part of fifteen minutes. Having finished his work even earlier than the Mayor, he was allowed to go ahead and heat up the car. The first minute in the car was just as stressful as the last. Unlike what her office would have onlookers believe, she kept herself neat and organized, with not even a single candy wrapper littering the floor. The chairs were comfy, and the heat melted the frost from the outdoors right off his bones.

But a few seconds after he entered, after admiring the interior for a bit, the problem surfaced. The car wafted her scent. It was immediately noticeable when he leaned into the car and only persisted with time. He never really noticed that the Mayor had a scent until now. A sweet coconut, with maybe a tinge of vanilla. A lovely scent, for sure.

That alone wouldn’t do it, though. He could feel the musk wrap around his body as tight as the coat he was wearing. It became easy to wonder what it would feel like to be gripping her back, covered in a sheen on sweat as he went to town on her.

And now she was in the car, getting comfy right next to Anon. She looked over and grinned. If she noticed his soldier at attention, she didn’t show it. So, he decided to finally answer her question.

“Er, yeah…” He breathed, turning away and immediately trying to focus on anything else to calm his red face. He’d definitely have to get home and hit the spank bank later. “Your work… did it take long?”

“Oh, I didn’t take too long, did I?” she asked, quickly shuffling to get herself comfortable. Once everything was in order, she reached for the aisle between them and gripped the gearshift. “I rushed to finish, but I knew I shouldn’t leave without a quick proofread.” Anon put up his hands and waved them dismissively.

“You didn’t really have to rush.” She pulled into reverse, the wheels crunching slightly against the snow. She didn’t respond, instead offering Anon a friendly smile as she pulled into drive and began down the snowy road.

The drive was quicker than he expected considering they were driving on snow. Every now and then, he could see the Mayor squint before pulling to an immediate halt at red lights, and her slight bite of the lip while she made turns with the crowd. Anon wondered if she realized that he was essentially staring at her. Still, the car eventually pulled over and into the parking lot of a small place.

From the car, all Anon could see were bright neon lights, unsure of their purpose or wording. The smaller sign just above the store’s entrance shed some light on their location, as it read “STEAK” in big bold letters, among other things. Anon turned to the Mayor, watching her pull the keys out of the ignition.

“Let’s head inside. They’re probably calming down from the dinner rush.” She left the car first, popping open the door to the frigid cold once again. Anon followed suit, his boots crunching in the now freshly fallen white snow. The cold was a secondary thought, as he could finally breathe without taking in all of his bosses’ scent. Still, she carried it with her when she went into the restaurant, so he made a note to keep his distance a few feet behind.

The inside of the Steakhouse( which Anon found out was named “What’s at Steak!?”) was just as warm as the car, but the juicy smell of meat cut through his body like a hot butter through a knife. His body seemed to melt too, his mind nearly forgetting all about his earlier thoughts. The Mayor walked forward, garnering the wide-eyed stare of the clearly tired waitress right in front.

“Oh! Um, Miss Mayor?” The Mayor returned one of her signature smiles, which only seemed to make the lady panic more. “H-How can I help you, ma’am?”

“A table for two, please.” Her voice commanded respect as it did at the office, but it was softer on the ears. Like she had said, the restaurant was all but deserted save for a few groups and couples. The lady scrambled, quickly grabbing two menus before quickly rushing to an empty seat. It was quite the spectacle to see people freak out over the Mayor. To him, she just seemed like a respectable elder.

His cheeks heated back up, remembering how vivid his descriptions of the very woman sashaying in front of him were. He took a few deep breaths, calming himself down before his fantasies got too carried away. Respectable elder. Respectable elder.

“Do you think we look like a couple, Anon?” He could hear the chink as it was made in his armor. He gulped, but kept his eyes forward and alert.

“No way,” he said, blankly. “Er, I mean, you’re so much older than me and all.” The Mayor’s smirk turned slightly devilish.

“Come now. I’m only 55.” Anon's eyes widened, as did the Mayor’s. “Ah… I don’t believe I’ve ever told you my age, have I?” Anon shook his head, and the Mayor simply waved it off. “I don’t really mind if you know, but try not to spread that around much, hm?”

“T-To be honest,” Anon sputtered out. “You look damn good for 55!” Immediate regret had never come swifter to a man. He was thinking of what to recant to, though he couldn’t get anything out. Though, weirdly, he didn’t seem to have to.

The Mayor's eyes seemed to shift to the ceiling, then back forward as the waitress seated them. As Anon slipped silently into the booth, he finally got to see her face fully.

She was… annoyed?

“You can order now if you want!” The waitress chipped in eagerly, placing the menus she’d brought onto the table. Anon picked his up and failed comically at trying to hide (while also admiring the selection of steaks, it was quite amazing). “Take as much time as you like…”

The waitress scurried off almost immediately. Anon could faintly hear her freaking out in the kitchen, but he had his own battle to fight.

“S-Sorry for what I said.” Anon thought he might as well use this moment to finally apologize for his words. She didn’t respond, instead, keeping her eyes closed. A few more moments of silence passed before he quickly added. “I probably shouldn’t have said that out loud like that, even if the restaurant is near empty.” Suddenly, her friendly smile reappeared, and her eyes slowly opened.

“I don’t mind it, really,” she said, pressing her hands in her lap and tilting her head down. “Thank you for the compliment, Anon.” Again, her tone felt almost strained, but again, Anon didn’t mention it.

“N-No problem…” The Mayor’s smile hadn’t wavered, and Anon was at least thankful for that.

Due to the place being practically deserted, the waitress got back to the pair quickly, still not over the fact that the Mayor of the town was eating here. The food came almost as quick, both of them getting their steaks and an assortment of sides.

Anon had just taken out one of the utensil sets to dig into his steak when the waitress swung by one more time with a glass stein frothing to the tip with a yellow liquid. Anon easily recognized it as the beer she’d ordered with her meal. He didn’t expect them to bring out the big guns, though. She placed it right next to the plate she gave the Mayor just a second ago before waving goodbye shyly and escaping back into the kitchen.

“I didn’t know you were a drinker, Mayor.” Anon quickly stabbed his steak and pulled the meat from the bone. The Mayor picked up the stein and he slipped the meat into his mouth. It damn near slipped right back out when The Mayor lifted the glass to her lips and took a hefty swig. Enough to get the glass down to half. Anon managed to pick his jaw up enough to speak again before long. “M-Mayor Mare? Are you okay?”

“Oh, don’t worry about me,” she said, placing it down with a thud. “A nice drink before a meal ever hurt anyone.” Anon was sure he could google it and prove her wrong, but he voted against it. “Do you drink, Anon?”

“A bit, I suppose.” Anon tried to remember the last time he drank more than a few shots for a holiday and came up with nothing. “I’m not sure I can really match you, though, Miss.”

“That’s no fun,” she responded, fingering the rim of her glass. Her eyes turned shockingly sharp as they turned to Anon. “How about we have a little competition, you and I?” Anon’s brows furrowed.

“What do you mean?” He asked, confusion written on his face. The Mayor’s gaze drifted downward, her eyes emphasizing the glass in front of her. It wasn’t too hard to figure out her competition idea. “Oh… I really don’t drink all that much,” he repeated. He tried to play it off with a chuckle. “B-Besides, one of us has to drive back.”

“Do you think I haven’t noticed?” She countered, a hint of that devilish smile returning from earlier. “It was quite the shocker to find out what you think of your boss, Anon.” A jolt of ice-cold ran through his veins, though he gritted his teeth behind his lips to conceal it.

“I don’t know—”

“When you get to be my age, you learn to pick up on the habits of liars,” she said, hiding her mouth behind interlocked fingers. It was still pretty clear that she was smiling. “Though, I understand. When you’re young, it’s healthy to have an active libido. Yours is on a whole different level, though. Quite admirable. And desirable...”

Anon had no reply to her words. All he could think to do was glance downward and pick at his food. He was sure his face was flushed by now, and even in the dead of winter, he felt like stripping a layer down. Mayor chuckled and reached her hand out to caress Anon’s face. She lifted it slightly, bringing them eye to eye. Her smile turned softer like he was used to, but her eyes were more… predatory.

“What if I gave you what you wanted?” Courtesy of her hand, Anon couldn’t look away from the Mayor. With her other hand, she lifted the half-drained glass again, then raised her eyebrow. “A bit of drinking, and we can have quite the night, don’t you think?” Anon continued staring, not saying anything. He closed his eyes, grasped the drink in his hand, then downed it completely. With a similar thud, Anon laid the stein down, looking at the Mayor’s growing smile.

“Alright, Mayor… Game on.”

And they did have quite the night.

Too bad he couldn’t recall anything past that.

He was certainly awake and judging by the absolute bashing of his head as he opened his eyes to the morning light, he was drinking last night. Although thinking straight was a hardship, he mustered enough brainpower to at least think about looking around.

This was most certainly not his own room. It wasn’t closet-sized, for one. The light was coming from the left where a big window was blowing cool air into the hot room. Directly across from the foot of the bed was a large vanity above a dresser. Luckily, it was pointing directly at him.

He was shirtless.

In fact, there didn’t seem to be a single article of clothing on his body. Even under the fluffy white covers he was draped in. He lifted the comforter to confirm that his morning wood indeed stood tall.

Right next to it, though, was quite the marvelous sight. Another pair of legs also bare and connected to the one woman he’d been thinking quite a bit about recently.

“M-Mayor!?” His voice came out as a weak croak, and he was thankful for that. He didn’t want to risk waking up the sleeping beauty. She was similarly in the nude, and her breathing was light and warm against his neck.

Anon slipped out of bed, extremely carefully. The wind blowing through the open window sent a strong chill up his spine. Looking for clothes would have to be his first priority.

“Oh, you’re awake.” Anon jumped out of his skin, nearly falling over from the surprise. He turned back to the bed, meeting the eyes of his boss as she got out of bed. It was hard to tell before, but her body was amazing. Large, supple breasts, a slim figure, and a neat, healthy bush over what was sure to be a delicious pussy. Of course, his depraved glare didn’t go unnoticed. Mayor Mare yawned, then slid off of the bed, standing naked just as Anon was. “It’s quite early. If you’d like, I can make us some breakfast before heading out to the office.”

“W-Wait,” said Anon, blinking a few times. Mayor looked confused, tilting her head to the side slightly. Anon gulped, then addressed the elephant in the room. “Did we… what happened last night?” Her eyes widened with surprise, and she put a hand on her breast.

“You don’t remember? Were you that drunk?” She hummed to herself, then shook her head. “Even though you went down on me so savagely…” Just the thought was enough to make his soldier salute. He looked away, biting his lip.

“I can’t remember anything past… leaving the restaurant. I think I fell asleep in the car.” He looked down at his feet and clenched his fists. “I missed my one chance.” Mayor Mare chuckled, then shook her head.

“Sorry,” she said, smirking. “That wasn’t true. I do like messing with you young ones.”

“Then why are we both naked?”

“It was to sell you on the joke,” she said, innocently. “Perhaps I took it a bit too far.” Anon opened his mouth but didn’t say anything, quickly closing it again. This was a little extreme for a simple joke told at the expense of your employee. She stretched, once again pulling Anon’s lecherous gaze to her chest, before walking over to his side of the bed. He were a bit apprehensive until he saw her reach for the closet behind him. “Well, I’ve had my fun. It’s time to get dressed and get ready for work.”

Anon reached out and grabbed her wrist. He didn’t grip too hard, but definitely enough so that she was deterred from snatching it away. Mayor met with Anon’s determined glare, a small, devious smirk slowly crawling onto her face.

“Might I ask what you’re doing, Anon?” She turned towards him, exposing her entire body clearly for the first time. They were close enough for Anon’s dick to tickle her stomach at full mast. She glanced down, taking note of this, before looking back.

“Last night, you said that you’d let me have what I wanted,” he said, confidently soldiering on. “And what I want is you.” The surprised look Anon expected Mayor to have was instead filled by a dangerously sexy pair of bedroom eyes. She leaned in closer.

“Ah… when I get in the mood, I’ll be there for hours.” She spoke in a voice slightly higher than a whisper, sending a delightful shock down Anon's spine. “In fact, we might have to take the entire day off.”

“You’ll have all of me tomorrow,” said Anon, letting her wrist go and snaking around to her back. Anon's touch seemed to be arousing her as much as her figure did to him. He was so close that he could feel her subtle breath against his lips. “So today I’ll be taking all of you.”

“Then… I suppose I should come clean,” she muttered. “As you probably guessed, this wasn’t a joke. Last night I said that I’d recognized your libido as extremely desirable. The way you undressed me with your eyes would never fail to send a chill up my spine.” She reached up to him, then cupped his cheek in her palm. “But despite that, you never made any advances towards me. Even on that night, when you were drunk out of your mind, you didn’t even let it slip that you wanted to pound me into the ground.”

“So, I set up this little experiment,” she explained, looking over to the bed. “If I couldn’t get you to unleash your desire while splayed out in the nude, then I would simply have to give up on you.” Anon smiled.

“It’s good that it worked then, hm?” asked Anon.

Anon finally kissed her, hungrily seeking more and more as seconds went by. His tongue danced with the Mayor’s, exciting his dick to the point where it indented the soft skin on her stomach. He could barely allow himself a moment to breathe. Every moment he was away from her was a moment he could be indulging in her sweet lips.

Despite this, he was pushed backward, stumbling until he fell backward onto the bed. Mayor Mare licked her lips, her eyes becoming even more devious and hungry than before. She quickly slid onto her knees, pressing his twitching, eager cock against her warm cheeks.

“Good, good! So young and full of energy,” she grasped the shaft and quickly pumped a few times before licking the pre that had dribbled over right off. Anon could barely keep his groans contained as she took the entire shaft in her throat all at once. She didn’t pause once until her lips reached the base of his cock, and his pubes tickled her nose. Her tongue deftly swirled around his cock, quickly dousing every inch of him in her sticky saliva until she was satisfied. She pulled back slightly, then jammed him back in.

He could feel every contraction of her throat as she all but swallowed his dick. The sensation of warm, wet, and active muscle reminded him of what he looked forward to down below. For now, he was happy to have his cock so masterfully attended to.

Anon ran his hand gently through Mayor Mare’s hair, subtly guiding her head up and down. She responded with a pleasing growl and sped up her head. He wanted to compliment her skill, but opening his mouth only led to a guttural moan.

Finally, she pulled herself off of his dick with a resounding and satisfying pop. She lifted her hefty breasts, slipping his slick dick right in between them snugly. She began by pressing them together but quickly escalated. Every one of Anon’s heartbeats came with a hefty slam of Mayor Mare’s breasts against his thighs.

“Cum!” She spoke through grit teeth, saliva wildly running from her mouth and her eyes hungrily eyeing the helplessly pleasured look all over Anon’s face. “Cum all over me… now!” Her commanding voice pushed his right over the edge and into the abyss. Cum shot straight up into the air, indiscriminately painting the Mayor’s face, tongue, and breasts with long strands of clear-white. Anon couldn’t do much more than grabbing at the sheets of the bed while she absolutely drained his balls.

“Fuck me…” moaned Anon, slowly calming down. Mayor pulled herself away from him, leaving small strands of cum all over his thighs. She chuckled as she stood up straight, slowly lapping what cum she could reach with her tongue up.

“Amazing vigor. And even more impressive volume,” she said. “But I think it’s time for a quick shower, don’t you think?” At first, Anon felt disappointed. After getting himself worked up, he’d have to wait however long for Mayor Mare to get out of the shower.

But after she walked a little away from him, he understood her words. Her legs were quivering and several lines of ladycum were already dribbling down her thighs. She paused for a moment to look back, her devious smirk returning once again. Anon got up, reinvigorated and excited.

Anon barely even waited until the two had entered the bathroom to begin his attack on her body. After opening the door and revealing a small shower, Anon slipped behind her, snaking his hand to her front and pinching her clit slightly. She looked just about ready to collapse there, but Anon kept her on her upright. He slipped one finger past her folds, then fit two. He began pumping in and out, getting a feel for what was beyond those heavenly lips.

She shakily turned the water on, leaning on the wall to avoid falling forward in pleasure. Even though they were dirty with his seed, Anon pinched at her nipples, ripping depraved moans from her each time he did. As close as he was behind her, his cock could feel the drips of precum coming from her pussy. It wouldn’t handle this foreplay for much longer.

“Pass me my soap. I’ll wash off my front quickly.” Anon paused his toying of her body to grab the bottle to the side of the shower and pass it to her. She stepped under the flowing water of the showerhead, and Anon quickly followed suit. She turned towards the water, quickly washing away the cum from before. Anon grabbed his cock, then prodded her entrance. “I’m ready whenever you are, An—”

Contrary to her words, she yelped and nearly dropped her bottle of soap when Anon shoved himself deep inside with one thrust. His hands held firm on her hips, fearing that she would collapse without them properly there. Mayor Mare leaned forward, leaning on the tile wall underneath the showerhead. The water ran down her back, and Anon could see her ass expand and contract every second his cockhead mushed up against her g-spot.

“Yes, god yesss…” begged Mayor Mare. Anon felt himself lose any semblance of restraint as he gripped her hips. He pulled back and slammed into her again, this time, making her knees buckle and nearly cross. He leaned down, grasping one of her breasts in on hand and her chin in the other. He pulled her eyes to his.

“When I’m done with you, you won’t know anything but this feeling,” he said, thrusting in again. She moaned, then bit her lip with anticipation. “Every moment my dick isn’t pressing your womb, you’ll be wishing you were a rutted, sopping, begging mess of a woman.”

“Mmph, ooohh,” she whimpered. The deep, depraved breaths of Mayor Mare only served to make Anon harder, relishing the fact that just last night, all of this was nothing more than a dream.

No matter how much she trembled and quivered, Anon wouldn’t stop pounding into her eager and awaiting folds. Every time he pulled out, he could feel her body try it’s hardest to pull him back in. He’d oblige, squishing her g-spot into nothingness before repeating over and over.

Mayor Mare certainly showed her experience as well. She knew exactly when to squeeze herself down and pull the most pleasure out of Anon. Every few pumps, he’d pause for a break, and Mayor Mare didn’t miss the chance to shake and swing her ass around before he went back to breaking her in.

He pulled out, taking one of her legs and flipping her over. He slammed her back against the tile. He grasped her by the butt, lifted her properly, slipped in once again, and continued his assault. Now, her moans and growls echoed directly in his ears. As well as her pleas for more. Despite her age, he held nothing back.

“Fuck… fuck!” Growled Anon. His cock was twitching violently, threatening to burst again at any conceivable moment. Just the thought of flooding Mayor with his seed until she couldn’t hold another drop sent waves of pleasure through his body, giving him the last push he needed. “Are you ready, Mayor? I’m gonna blow every last bit of cum I have.” Mayor moaned a happy, yet shaky sound into his ear.

He held nothing back. He felt himself erupt into the deepest folds of her pussy, scalding hot seed filling her womb up by the second. It came in short but powerful bursts. Mayor Mare clenched her arms around Anon every time another volley of cum found a home inside her. It felt like hours, but could only have been moments.

Once it was all over, a wave of weakness fell over Anon. He couldn’t just drop Mayor Mare, but he slowly let her down from her position pinned against the wall. Once on her own feet, Anon fell back, leaning against the other wall.

“That was… divine,” he said letting the water wash away the sweat he’d worked up. He looked up at the Mayor, who was doing something similar. Her eyes looked empty and her body was twitching and shaking slightly. He reached over and caressed her cheek. “Sorry about all that stuff from before. I was… just excited and in my own head.”

“What do you mean,” she said, focusing her eyes on his. “You’re saying that as if you’re done.” Anon raised an eyebrow.

“W-We’re not done?” Mayor Mare chuckled.

“I do believe I said that we’d be taking the whole day, Anon.” Anon’s eyes went wide as she closed the distance with a kiss. The Mayor Mare whom Anon thought had been washed away in pleasure had returned in force. This woman’s force of will was amazing. “We can get cleaned up and get some breakfast, but make no mistake.” She grabbed him by the balls, giving them a loving squeeze and making him jump. “It’s going to take more than one load to properly breed a woman like me, understood?” Anon chuckled nervously but saw that she was 100% serious. He sighed, then nodded.

“Yes, ma’am.”

Easy Prey

by DrySpell

Eyes on the Prize