Who knew that you would get into all sorts of crazy situations after high school? Who also knew that you’ve struck it big on top of all that? Well, you’d have to chalk it up to that fateful day that when you had that lustful encounter with the dean of CPA. From there, it was a job at the CSC and a sensual night at a spa that bumped you up to being the assistant of your boss: Ms. Harshwhinny.

But, there was one stipulation to that arrangement.

As was agreed upon, your sexual night with Ms. Harshwhinny resulted in her getting pregnant, just as she desired. Over the next four and a half months since your return from a state mandated vacation, her belly grew bigger over time as the life within her developed. Though she was prone to mood swings and the occasional cravings, she kept them under control. But still, you saw that she was going to be a good mother… and a damn sexy one at that.

It was medium paced day at work, making your rounds and verifying data gathered by financial. The days were becoming more hectic, but you kept your cool through all that. Why were things becoming increasingly busy? Well, It’s because the Canterlot games were due to happen in the next two months. Around those times, the CSC’s efforts are kicked into high gear, ensuring that their efforts are always at 110%. Because of you being Ms. Harshwhinny’s assistant, you get some hard tasks on your hands, but it all provides your brain a worthwhile challenge and freedom from boredom. Everything was optimized and in order. As far as you were concerned, all was well.

*BUZZZZ*
*BUZZZZ*
*BUZZZZ*

Your phone buzzed and rang in your pocket. Answering it, you were greeted by a familiar voice.

“Hello, Mr. Crunch,” said Ms. Harshwhinny. “I trust that things are going well over in financial.” The tone of her voice sounded more casual to you than it was five months ago; almost into friendly territory.

“Yes, Ms. Harshwhinny,” you answered. “Apart from a few minor discrepancies, all the numbers seem to be in order.”

“That’s good to hear. Your talents are were they should be. Now, come to my office. There’s an assignment that I need your assistance with.”

“Alright, I’ll be there in a few.”

Hanging up, you wondered what she wanted help with. Could it be a personal matter, something job related, or something of a more lewd nature? Well, there was only one way to find out.

You arrived at the double doors to her office, so grand and fitting for a Opening them, you saw a casually relaxing Ms. Harshwhinny, five months pregnant and reading a book. As the doors closed, her attention was directed towards you.

“Ah, Mr. Crunch,” she warmly greeted you as she rubbed her belly. “so nice of you to join me.” For others, she would’ve been a lot more professional than she was. But for you and due to the fact that she’s carrying your child, she was more cordial. With a wave of her finger, you walked over to her, placing a hand on her warm and bulbous midsection. It was clear she had a sort of affection towards you, but in an arm’s length sort of way. So, the relationship was professional on the outside.

“So, how’s the baby?” you asked.

“It’s doing fine,” she replied. “I had an ultrasound on top of my checkup last saturday. They asked me if I wanted to know the sex of the baby but I told them that I wanted to be surprised.”

“Hmmm, didn’t know you were like that.” In response to your statement, Harshwhinny gave you a quick peck on the cheek. You blushed, but not for long.

“There’s a lot of things you don’t know about me, Mister.” Then, her face snapped back to her serious and professional expression. “Now please, take a seat.” Doing as you were told, you sat back on the couch, relaxed but alert. Clearing her throat, Ms. Harshwhinny prepared to speak. “You may recall that the Canterlot Games are due to take place in the next two months.”

“Yes, no wonder things are in a bit of a rush as of late.”

“Indeed. Now, we get our funding from not only the business we do, but private organizations, private entities, tourism, and the event itself. Most of the time, we end up with a surplus which we can devote to other functions related to the event. With you being my assistant, I’m putting you in charge of the overseeing of these factors.”

In your current position, you expected this eventuality. Due to how long you’ve been working on things too easy, this would be a welcome task. After all, idle hands are the devil’s playthings.

“Really? W-Well, I won’t disappoint you, ma’am,” you replied with a tinge of excitement.

“I know you won’t, considering that your *Ahem* ‘skillset’ would be fit for this assignment. One of our financial benefactors is Filthy Rich and his wife, Spoiled Milk. He owns a lot of businesses around town and in a few other nearby cities. When it comes to making decisions, it would be a mutual agreement between them… and that is where the problem lies.”

“What could be the problem? Ms. Harshwhinny let out a long annoyed sigh before explaining.

“As of late, their marriage has run into shall we say… ‘problems’. Judging by the last time her and I spoke casually, it’s that not only has her husband been increasingly busy as of late, he’s also been ‘unsatisfactory’ if I may use that term. As a result, the stress of the situation has rendered Spoiled unwilling to contribute to the funding, which leaves us slightly underfunded.” Judging by the tone in her voice, the situation annoyed her greatly. From what you could understand, It would mean that she would have to make changes to the budgetary baseline. Moreover, when she mentioned your ‘skillset’, you could already tell what she intends for you to do.

“So, what do you need for me to do?”

“Spoiled Milk is doing some chores around town this afternoon. You’ll be tasked with chauffeuring her around as she accomplishes her tasks. You’ll be advised to help her around and maybe take her to lunch on your dime. If she hasn’t calmed down by then, do what you do best at your discretion.”

‘Do what you do best at your discretion.’ basically meant she was giving you liberty to sway her attitude toward the funding, even if it meant giving her some carnal pleasure. Though it would seem to be not too difficult of a job to accomplish, you would only resort to sex as a nuclear option.

“Alright, I’ll do it” you agreed with a nod.

“Excellent,” she replied with a wry grin. “Now, for this plan, I’ll permit you to go home early to prepare yourself. Make sure your well cleaned and dressed in your best suit. Be sure pick her up at 3:30 PM, to use your new car and oh, watch out because she’s a bit quick to irritate.”

Quick to irritate? Well, that can complicate things. But then again, you’re a patient man. Getting home early would net you two hours to prepare, more than enough. Shaking her hand, you left for your car, a Jaguar F-Type. It was an expensive car, but Ms. Harshwhinny just makes things happen.

Arriving at home, you took a few minutes/hours to rest up before making yourself look like a million bucks. You showered, shaved, and anything to make yourself the most presentable since your interview. Once all that was done, you hopped in your jaguar and drove off to the address Harshwhinny gave you. It was an incredibly fancy mansion, one that stuck out like a sore thumb. It was almost made in a way to assert the owner’s superiority.

Giving the horn a few honks, a woman stepped out and boy was she a sight to see. Thick thighs, ample cleavage, a lovely dress and flowing magenta hair. However, the only blemish you saw was the sour look on her face. Aware of her irritable nature, you took a deep breath and braced yourself.

“Afternoon, Ma’am,” you greeted as she entered your car.

“You’re a minute late!” she said with a huff of self superiority. “Then again, I never expected Julia’s assistant to be so… young.”

“I actually get that quite a lot.”

“Indeed. I hope you’re smart enough to follow simple orders Now, I want to hit the nearby clothing store on 8th Street. I certainly hope you know where you’re going.”

“I do, know the town like it’s in the back of my head,” you said as you revved the engine. I’m not an idiot… bitch.

Following her instructions, you drove Spoiled Rich to her destination. It was a ritzy clothing store that only those with deep pockets could afford to go. For an hour, you and the rich MILF roamed around the store, seeing her try on shoes and clothing of varying types. When that was done, you walked out hefting six bags of the stuff she purchased.

“Hmmm, you’re not even breaking a sweat. I’ll give you that,” Spoiled said as you loaded the cargo. “So far, you’ve proven a reliable servant.” The last part she said was with a condescending tone. It infuriated you, but you had to stay your hand of anger and not screw up. Hopefully by the night’s end, you’ll walk away with her renewed commitment towards the funding. “Now, I’m a little peckish. Take me to Lorenzo’s Villa. I’m in dire need of some good chicken cacciatore.”

As you command, Mrs. Bitch.

Driving about ten minutes away, you reach the eatery she informed you of. You recognized it from your occasional walks or your trips to the smoothie bar. At first glance, it was a pricy place. Hell, you’ve looked at it’s menu online at it was quite expensive, but the reviews say the food was good. Even during those trips, the scent of its kitchen enticed your curiosity. But hey, her wish is her command. After getting seated, you both ordered your drinks and food. An awkward moment of silence lasted for minutes after before Spoiled broke the silence.

“So, Mr. Crunch,” she asked. “How did someone so young such as yourself became Julia’s assistant?”

“Well, I was junior level accountant for two years. She noted how my skills was being underutilized and decided to bump me up to her personal assistant.”

“Hmmm, I see. I would see that you’re not as dumb as your body makes you out to be.” That quip of hers infuriated you. At that point, you wanted nothing more than to just reach across the table and clock her. However, you didn’t want to get into untold fathoms of trouble. Thus, you decide to endure her swath of denigrating language.

“Well, I’ve found that a good body and mind go hand in hand.”

“Interesting. But, how did you become her assistant in such short amount time? Then again, her being the president of the CSC, she calls the shots.”

“Yes ma’am. Though, I do feel you know what this is about.”

“I know. I’m still pissed that my shriveled up sack of impotency of a husband is on yet another trip!” She blurted out with a slam of her fist. Her eyes spelled the irritation of a unsatisfied wife, a dangerous prospect. “What about me?! All he ever talks about is business. He had the nerve to ask about the games last week. So, I told him to stuff it and I’m not changing my mind until I say otherwise!”

“Sounds like your relationship with your husband is contentious.”

“You don’t know the half of it,” she replied as she took a sip. “I know Julia wants the funding. I’m open to reconsidering my stance but that’s a ways off. At the end of our time together, I may or may not so don’t be upset or surprised if I decline.”

Her anger and discontent was made clear in her tone. It was clear that it would take way more than just a few good gestures to crack the shell. You knew then and there that you’ll inevitably have to resort to the nuclear option. Though you’ll have to wait for the right time. Before you could further muse about the situation, your meals arrived.

After dinner was done, you drove her to another couple of places. Everywhere she went, you followed like a pack mule. For her, that’s all you were. Your strength was more than enough to keep up, but her usual string of insults towards you made your anger climb ever higher. Still, to avoid problems, you had to endure them to the same degree you endure pain in a workout.

After a trip to a jewelry, you drove her home. You followed Spoiled in, hefting all those bags of merchandise she purchased. You could barely see ahead of you but she was cautious enough to lead you around. After off-loading the cargo in her room, you both met in the living room. Your anger was still present after her choice of words.

“So, Mr. Crunch, you did good for someone of your... calibre,” Spoiled said with a hint of sarcasm.

“Well, I aim not to be a slouch in my work,” you shot back.

“And it certainly shows.”

“Thank you. Now, as for the situation about the funding…”

“I know you want to know about that. As of now, I see no reason for me to change my stance. I’m still stressed as it stands.” Spoiled got up from her seat with her voluptuous chest jiggling about. “Now, I’m going to go freshen up in my bathroom and skinny dip. Don’t come for me until I say so. If you’re going to help yourself to a drink, clean up or I’ll make you regret it.”

“If you say so,” you said as Spoiled walked away from your sight. “Bitch.” Feeling a little parched, you grabbed a tea from the fridge. As you took a sip, you mused how Filthy had the patience to put up with someone as insufferable as Spoiled. Though nice looking on the outside, inside was pure bitchasaurus rex. Sometimes, you just have to bless someone for their high degree of patience.

As you began to kick back on the couch, you heard a moan coming from one of the bathrooms. It wasn’t like a normal stressed moan. It was more guttural and driven. It kept on going and going, sometimes accompanied by a sharp yelp. You want to go to ensure she was alright but her wrath is what you feared the most. After a while, it eventually subsided into silence and her footsteps were heard getting more distant. As soon as you knew the coast was clear, you made your move.

Taking a peek inside, the bathroom was spotless with a fresh floral scent. It was like she wasn’t there at all. You scanned your eyes around until you found something at the corner of your eye. It was a light yellow object with a light earth brown base. Taking a whiff, two scents became apparent: one was musky while the other was of ginger. Putting two and two together, it became clear what she was doing.

“Heh, how naughty of her.”

Arriving at the pool house, you opened the door with a deft movement of your hand. Walking in, you saw her: Spoiled Rich, naked, swimming around with water running down her hair. Your presence didn’t go unnoticed however as the moment she saw you, she screamed and covered her mounds and lower lips.

“Mr. Crunch, what in the hell are you doing?!” she yelled.

“I could ask the same of you!” you shot back with a mischievous look on your face. “For a rich socialite, you do enjoy some rather profane activities.” She starts to growl and fume with rage, rage over being interrupted during her private time.

“That is none of your business, mister!” she screamed as she climbed out of the pool. “As soon as I can, I’ll file a suit against you. I’ll have every single penny you have!” You began to laugh at her threats of a lawsuit, even as you pulled out a piece of shaved ginger root. The sight caused Spoiled Rich to freeze for a moment. “What is that?”

“You tell me. I’m not the one that turned to pleasuring myself with roots after years of dissatisfaction.”

“How did you find out?”

“Well, you should’ve thrown that other root away.” She began grow more alarmed with her eyes darting back and forth before attempting to run. However, you anticipated it and pinned her against the wall. Your already throbbing erection presses up against her snatch, though restrained by your clothes. You’ve spent a good while hiding it from such a specimen of MILFy goodness. Now, you were going to make her repay those insults.

“Unhand me, right now!” She protests.

“Oh no,” you said as you began unbuckling your pants, kicking them away as well as your shoes. “We’re going to address this, now! I have a feeling our little ‘meeting’ could make you more receptive.” With the miracle of just one hand, you unbutton your shirt. Then and there, you were completely nude in front of a woman that is prepared to sue you at any minute, but you knew you couldn’t walk away empty handed or Julia would have your ass.

You turned her around, wrapping your arms around hers and taking her to the ground with you. Spoiled struggles as she tries to break free but your strength made it impossible. Try as she might, she couldn’t break away, even as you put the piece of ginger root up her cooch. She tensed up from the surprise burning effect of the root’s juices. Each and every movement of the ginger gave her more burning pleasure than ever and lessening her resistance. Still, you had to pacify her and you want to do it fast and be done with it.

Using your other hand, you fiddled around with her clitoral nub. In that moment, her will to resist had eroded completely. For the longest time, Spoiled never felt that good before and her husband was to blame. Now here you are, filling the void he left. It didn’t take her that long to reach her climax as she soon soaked your hand with streams of her essence. Her moans subsided and gave way to panting and exhaustion. It became clear that Spoiled liked it, right where you wanted her.

“My word,” she panted while sitting up. “Filthy never made me feel this good.”

“What can I say, I aim to please,” you replied.

“Indeed. I can certainly see why she chose you to be her right hand.”

“How did you...”

“Know? Julia told me.”

“Oh. Well, I’m glad you liked it.”

“Hmmm, indeed. Now, I suppose it’s only fair if I repaid you.” Before you could react, she grabs hold of your erection. It throbbed in her hand, sensitive to her touch. For a second, you felt as if you were about to blow your load too early. But hell no, you weren’t going to give her ammo to mock you. “Shouldn’t you be kissing me, sir?”

And kiss her you did. Mashing your lips with hers, the sudden arrival of your smooch caught her off guard, leaving you with a window to invade her mouth with your tongue. Shaking at first, Spoiled eventually warmed up to such an amazing kiss. She eventually placed one of your hands on one of her breasts. Each squeeze and fondling of the bulbous mound earned a moan from her and an increase in the frequency of her strokes. You gave it your all, buckling down to endure as long as you could, never leaving the kiss.

Try as you might, you couldn’t last forever. With a final throb, your cock erupted ropes upon ropes of your sticky, life giving seed. You didn’t know why your hips involuntarily thrusted as you came. One could chalk it up to reflex action in the midst of an orgasm. Either way, relief flooded over you as your dick goes limp, still dripping a tiny bit of cum.

“Hmmm, that’s quite a lot and you’re… still hard?!” Spoiled remarked upon seeing your still hard shaft. Just the sight of it made her nethers salivate with her musky nectar. . “I have an idea: Get in the pool and allow me to take the lead.”

Following along, you climbed the ladder down into the pool’s deep end, resting your arms on the ledge. From the other side, Spoiled swam over to you. It was strangely arousing to see a woman in her natural form swim around in water. The very sight of her breasts and hair soaked in water made your member tingle and throb. The second she got to you, her arms wrapped around your neck and the entrance of her honeypot was parked on the tip of your spear.

“Shall we?” Slowly, your member was engulfed by her vagina. For an older woman, Spoiled was pretty tight, another sign of an unsatisfactory husband. She bounces up and down on your pole, splashing water around in all directions. As it went on, her motions became more wild and unbound. Starved and crazed, she moaned and groaned. Suddenly, her inner walls clench and let out a loud wail as she came. However, you were nowhere close enough to cumming.

“Why… why didn’t you cum?!” she gasped.

“Well, I didn’t want to disappoint you,” you shot back. “I want you to enjoy this.”

“Quite the charmer.”

Taking a few moments of reprieve, she resumed her ministrations, bouncing harder than before. She clearly wanted to feel your hot seed inside her and she was going to get it, even if she has to endure multiple orgasms. Holding you tightly, she uses the power of her hips to do the job, letting her give you a very hungry kiss. She would orgasm several more times before you feel your cock about to explode. She was starting to slow down but you aided with some thrusts of your own, matching with her rhythm as best as you can.

Soon, your cock quivered and exploded once more with your essence. You thrusted a few more times for good measure, seeing Spoiled collapse a bit, exhausted yet satisfied. You carried her out of the pool and onto a bench, allowing her a few moments to get her bearings.

“Oh my word,” she wheezed. “You’ve done more for me than what my husband did in a while.”

“The pleasure is all mine,” you replied as you dried yourself off. “Also, I’m willing to excuse your choice of words.”

“Fair enough.” Then, a thought occurred to you. You’ve done it without a condom and it was likely she didn’t take any pills.

“Are you going to be alright if you get... knocked up from this?”

“Don’t worry about it, kid. If I do, I’ll just say it’s his.”

“You sure he’ll buy it?”

“Yes. If not, it’ll be all the reason more to spite him.”

“Fair enough.” You got your clothes back on. Though they were a bit damp, they looked fine for the most part. “So, about our arrangement?”

“Yes, you can tell Julia that I’ve changed my stance. Our little dance earlier actually made me feel much better.”

“Good to know.”

“Indeed. Now, It’s best if you leave now. My daughter will be home soon.” Before you could lay a hand on the door, Spoiled’s voice called forth once more. “Also, I might be needing your services again. Don’t worry, I’ll come to you.” Nodding, you walked away and into your car. As you drove off, you dialed up Ms. Harshwhinny.

“Hello, this is Ms. Harshwhinny.”

“Julia, how were things at the office today?”

“They’ve been good for the most part. So, how did negotiations go with Mrs. Rich?”

“Swimmingly. She changed her mind and it looks like funding will be back on track.”

“Splendid. I knew your oratory skills would be optimal for job.”

“Why thank you, ma’am.”

“Likewise. I’ll be expecting you in tip top form tomorrow.”

“You know me, I’m hardly ever a slouch. Heh. See you tomorrow.”

You hung up the call, focusing on the road ahead. Since you lived on the other side of Canterlot, it was a ways away to your house. As you hit the stretch of road near the forest, you saw a car and it’s driver standing next to it, a blue haired woman. She looked to be struggling with her phone, calling for a tow. The moment she saw your car, she waved you down.

“Mister, would you mind giving me some assistance, please?”

Author's Note

Whew, been quite a while since I'v written anything for this story. To be honest, it took me quite a while and my motivation to write this story started to falter a bit. I do apologize for keeping you waiting like this. Again, thank you for the reception you've given this story of smut and MILFery.

Here's a short teaser of Milky Way's chapter:

Once Milky was done with the breast pump, you were briefly able to see a sight of the nipple. Though you were slightly aroused, the fact that you've just met her made you fear those thoughts. You looked the other way, causing her concern.

"As I've said before, I'm used to receiving looks because of my 'things'." said Milky. "I'm not even the least bit offended."

"Well, it's that we've just met." You replied. You've heard a click and a ruffling of cloth. Turning around, you saw Milky Way, no top or shirt on, baring her breasts to you. They leaked a bit of milk out of the nipples as if welcoming you to taste some of the ichor within. You struggled to react but the sight of such a large pair of breasts made you indecisive.

"Now, do you want to feel them?"