Author's Note

Thank you to all who liked this story and got it featured, and held the number 1# spot for a good while. I hope you enjoy this chapter.

If you have ideas on which mares should be next and how Max would catch them, leave a comment or dm me

And to those who disliked this story, just know your suffering only fuels me more.

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Ch.2 First Day, First Mare

The next morning, Maxwell tucked and turned in his sleep before slowly waking up. His eyes blinked to help remove the blurriness and to focus his vision. Yawning he sat up and stretched his arms over his head, getting a few satisfied pops.

“Damn what a dream.” He groaned while licking his very dry lips. “It felt so real.” The memories from last night flooded his mind, and the deal that was made with Discord.

But surely none of it was real. Gaining the power of hypnosis and everything else he asked for from the lord of chaos. It all had to be a dream…..didn't it?

He got his answer when he pulled the sheets back and saw his newly enlarged member. The size was double what he woke up with the morning before, and even thicker.

“Well shit…..that really happened.” He said in bewilderment but somehow still calm. This meant if this was all real and the deal that was made was in fact also real, then he did possess hypnotic powers, and had a mission from Discord.

Then something clicked, a question that Max never asked Discord due to him being preoccupied. Grabbing the phone from his nightstand, Max opened his contacts and saw Discord's name at the top.

He clicked the call button and waited before hearing a voice. “I must say I wasn't expecting you to call this soon after our deal was made. Have you already found a mare to bang?” Discord's voice acting as though they have been doing this for a long time.

It took the human to mentally collect himself before asking the question that led him to call. “Not yet, but I had a question I never got to ask.”

“Go on?”

“How does having sex with mares boost your chaos powers?” Max asked while admiring his new cock.

“Oh, right I never got to tell you that.” Discord sounded actually surprising, no doubt having glossed over the idea at the time. “Well, when we shook hands, you were infused with my chaos magic. But to be more accurate your seed was infused, meaning if you fill a mare with your seed that magic will slowly begin to absorb into said mare.”

This caught the human off guard, and then had him worried. “Wait so when you say fill with my seed, does this mean I can impregnate mares now?” he asked, sounding nervous.

Discord laughed on the other end and took a few moments to calm down. “No no nothing like that, at least not yet anyway.” He quickly clarified before continuing. “No, what I mean is that all you have to do is cum in a mare, and your seed will get absorbed into their body, over time the mare's behavior will also change which will lead to an influx of chaos, which I will gain power from.”

This raised some questions for the human, given that if that's all it took to make sure Discord got power, then perhaps he had a plan. “Well, if that is the case wouldn't it be easier for me to target just one mare who I can easily mind control? All I would need to do is keep seeing that mare over till I level up.”

The creatures of chaos clicked his tongue and sighed. “I'm afraid it won't be that simple. As mentioned before, the strength of my magic is at a low, which also means the potency of your chaos seed is also not as potent. The best you could do is have sex with the same mare once a day, before needing for her to slowly absorb the magic injected into her. Plus, your hypnosis won't last that long at your current level.”

This quickly reminded Max that he asked for a means to check his progress. “Right and how would I check my skills again? You never told me how I would be able to check my progression.”

“Oh right, I have such a scattered brain sometimes. I added a new app to your phone, I believe you'll know what it is when you see it.” The way Discord spoke made it sound like he was excited by something.

Checking his apps, Max chuckled as he saw the app named Discord, except this version had an icon of him giving two thumbs up with a smile on his face. “Subtle, very subtle."

Clicking on it, he saw a character icon of himself. This includes his name, age, sex and other small information. But it was the second tab labeled “skills that really had his interest.

When he clicked it, he found himself slightly disappointed. There was only one skill currently visible. “Just one?” He asked.

“Well sorry, but giving you a better cock and charm boost, didn't exactly leave me with a lot of magic to give out to freely. Besides, it's the thrill of earning your skills that makes them fun.” Discord said with a high level of enthusiasm.

Rolling his eyes, Max clicked on the skills to get a good look at it.

Hypnosis Level 1

This level of hypnosis can only work on one target at a time. Those under the influence lose free will and require commands in order to move.

Upon waking up from hypnosis, the target will have no memories of what transpired and will act as though nothing happened.

Duration 30 minutes

Cool down time 24 hours (per target)

Warning

This level of hypnosis is weak, meaning should the target suffer any blows to the head, or hear the voice of someone familiar calling out, the hypnosis may be broken.

“Wait so I can hypnotize each mare only once per day, and the effects only last half an hour. That seems kind of weak.” Max added while getting out of bed, still naked and moving to the bedroom window.

“Well excuse me princess, but most stallions wouldn't even last ten minutes in the bedroom, so a whole thirty minutes should have been more than enough time to get the job done.” Discord said in a snarky tone, yet it was playful. “Besides, I think you are the only creature on the planet with such a high endurance.”

Max took that as a compliment and had to really think about his next move. He saw that he would need over five hundred experience points in order to level it up. “So, I assume the earning of EXP for my hypnosis is also limited per mare each day?”

There was an awkward silence as Discord said nothing, giving the human his answer. “Look, all you need to do is find some easy mares to grind for points, and you will level up in no time. Remember that difficulty level I mentioned?”

Thinking back to last night, Max remembered the order in which certain mares could be hard to hypnotize. “Yeah, what about it?”

“Well, if you managed to find say a dumb unicorn with low will power, you'll gain more point than you would fucking a pegasus or earth pony.” He added quickly.

So, depending on the breed of mare he slept with, influenced the points he could earn over all. This information was quickly filed away as he peaked out his window and saw something that made him grin. “Alright Discord, I think I get the idea. Before I hang up, can you do me one more favor?”

“And what might that be?” Discord asked, sounding genuinely interested.

“Can you snap me up a basket of muffins?”

Derpy Hooves was skipping her way through her rounds, delivering packages and letters while also leaving them in the wrong places. She left a package on top of one house, letters inside a flower bush.

Now this wasn't intentional nor out of malice, Derpy was just clumsy and made mistakes. One such mistake was skipping over to the house of the local and only human. She liked Max since he tolerated her goofy mistakes, and enjoyed talking to him whenever she had the chance. Luckily for her she had a package she needed to deliver to his house.

Trotting up to the front door she knocked on it and waited while holding the package in her hands. “Oh Max, I have a package for you!” She called out.

She waited for a few moments before the window to the left opened and Max poked his head out. “Hey Derpy, nice to see you. Hey um listen I have something important to take care of right now in my room, and I can't sign for my package just yet, can you maybe drop it off inside for me?” he asked in a pleading tone.

Derpy needed to think about it. “I don't know, mail pony protocol says that we shouldn't enter a client's house to make a delivery.”

Max looked sad and nodded his head. “I understand, shame too since I bought some fresh muffins on the counter, and wanted to share them with you, plus I have a package that needs delivering.”

All it took was the word muffins, and the mare had already opened the door and walked inside. “I can leave it on the counter, please make sure your package has the right number of stamps!”

The human smiled and made sure not to waste this golden opportunity. He had placed the basket of muffins on his kitchen counter in order to make sure the mare wouldn't see him coming.

Walking down the hall still naked, his member now growing rock hard with excitement. He peaked around a corner and saw the mare eating some of the muffins from the basket, her back turned from him. “Perfect.” He thought to himself.

Derpy had a rather shapely body, she had a nice bubble butt that had been the envy of most mares, and two large bouncy breasts. If he was not mistaken Derpy had kids which technically made her a milf.

Getting as close as he could, he leaned his body into her, his arms moving to wrap around her waist. “Are the muffins good?” He asked softly and in a friendly tone.

Derpy was slightly taken aback for a moment by his presence, but relaxed when she felt him hugging her. Giving hugs was something they did from time to time. “Mmm *gulp* hehe they sure are, I really appreciate it Max, I forgot my breakfast at home…again.” She continued to eat without knowing the condition her “friend” was in.

Max smiled, pressing his luck and moving his lower half closer to its target. “I'm glad I could help. By the way Derpy, have you ever got around to thinking about my offer?”

The pegasus mare stopped for a moment and sighed. Prior to this morning, Max had asked her out on a date, but the mare dodge the questions by saying the next time she'll answer. The truth was she didn't want to date after her husband cheated on her and left her while raising their two daughters.

She was going to turn him down when she smelled something. Her nose sniffed the air for a while and smelled something…familiar. It was a strong scent, one that she very much enjoyed. Not only that but she felt her heart getting warmer the longer she stayed next to Max. Could it be his pheromones?

Up till now she never once smelled them, and each time they hung out she never felt this warmth. Was this love? She hadn't thought about it since she did have girls to look after, but now she didn't need to with the youngest just turning 18 last year.

Then she felt something hard slightly brush up against her flank and gasped. She turned to look at the human, but felt her body stiffen. When one of her eyes caught a glimpse of his, all she saw were spirals of different shades of green.

Slowly one by one her eyes began to mimic his, her mind slowly growing fuzzy. For a while it felt like her whole body was spinning, yet she felt lighter than a feather.

Part of her wanted to resist, and she was going to voice her thoughts, when she felt herself being pulled in and her lips locked with the human.

She felt his tongue invade her mouth and slowly wrapped it around hers. Her breath was stolen, and she soon felt a hand move down to grope her flank. All this stimulation while still staring into his eyes. Before long, her mind faded and then.

PING!

That sound alone told the perverted human he had won, that victory was his and so was this mare. He saw a timer counting down from thirty minutes and knew he only had so much time with the mare. Yet this was his first of many hypnotize mares, so she needed to be savored.

He moved his hands to gently grab her breasts and slowly push them together, kneading them while getting some moans in return. “Don't worry Derpy you aren't on my hate list, so you'll get only finest treatment from me.”

Leaning back in, Max kissed her lips, and could hear her moaning as his hands still groped her breasts through her mail mare uniform. “Kiss me back my sweet, kiss me like I'm your true love.” He ordered.

Slowly the mare complied, her hands moved to hold the back of his head, while she pushed her tongue into his mouth to reciprocate the attention she was getting.

Max could feel the difference and very much enjoyed it. His hand moved to grab hers and guide it to his throbbing erection. “Jerk me off while you kiss, your lover demands it.” He ordered.

Obeying without hesitation, Derpy's hands moved to grip the human's cock, the girth not being to thick for one hand to grip, forcing her to use both.

Her hands cupped the tip before slowly sliding down along his member, before moving back up, and repeating this process over and over again.

The human moaned about getting such a treatment. Her lips hungrily sucked on his, her tongue moving into to caress his own, all while her hands stroked his newly enlarged member.

He was well aware no experience would be gained without him injecting her with his seed, but that didn't matter much to him, as he had been neglected too long to just rush in. But he wanted to make this more comfortable. He broke the kiss and stroked her cheeks. “Strip down and go wait for me in the bedroom. I need to make sure we won't be bothered.”

Upon hearing her orders, Derpy pulled away and undid her clothes, letting her large breast spring out of her tight shirt, and her bubble butt to bounce out freely as she slipped her shorts off. She turned on her feet and walked to the bedroom for her master.

Max wanted to ravage her body so badly, but he knew better than to get reckless. He made sure to lock the doors and close the curtains, less any peeping toms look in.

Before going to claim his long-awaited prize, he noticed the package on the counter. He then remembered what it was and opened it. Inside was a bottle of lube, that he ordered to help with his lonely nights of masturbation.

He smirked down at the bottle and looked back to his room. “Looks like I'll be using this for its intended purpose.” Walking into his room he saw the mare standing still waiting for her next order. Above the human could see he only had twenty minutes left. “Mmm worth it, after all foreplay is needed to spicy things up.”

He moved his hands to grab her now exposed breasts and massage them. They felt smooth and easily squished under his grip. “Now Derpy I want you to sit down on our bed and put that mouth of yours to good use.” He gave a vague demand to see if he needed to be direct with his orders.

Without missing a beat, the mare plopped her flank down on his bed, and leaned in to start kissing the length of his cock. She moaned softly as her hands moved to stroke the base of his cock, and one moved to fondle his testicles.

Max hadn't expected the mare to perform this well, making him wonder if she was more experienced than he thought, or perhaps this was an effect of the hypnosis.

Either way he had no complaints when she moved her lips to the tip of his cock, and slowly opened her mouth to take it in.

Letting out a deep moan, Max moved his hands to the back of her head and gave his hips a thrust. He could feel himself sliding deeper into her maw, and did his best not to cum immediately. While it would earn him experience points, he prided himself on not shooting his load too easily or quickly.

Derpy began to bob her head back and forth each time, taking more of her master's shaft into her mouth. Each time she forced herself to take another inch of her master's cock deeper down.

Max couldn't handle it much longer, even after Fluttershy's blowjob the night before, his cock was sensitive to the feeling of an actual blowjob.

He pulled down on Derpy's head and crammed the full length of his cock down her throat, getting a satisfying gagging sound, as he felt her throat squeezing around his shaft.

After a good few seconds of trying to cram his cock in deeper by humping her face, he unloaded his first chaos infused load into Derpy's throat.

The mare gulped and swallowed his cum, her nostrils flaring trying to breathe from them. In a moment she felt the hard member slip from her throat, and gasped, panting and coughing hard. Max had to take a minute himself to really savor the feeling. A shockwave of pleasure shot up his body from the tip of his cock to the top of his head. A pleasure he so desperately missed.

As he tried to compose himself, he saw his phone vibrate. This made him check and saw a notification that read. “20 experience points gained.”

“Hmm only need to do that twenty-five more times and I'll level up.” Max added before looking back at the mare who had cum dripping from her mouth. “Swallow that up and then get on all fours.” As commanded Derpy swallowed what cum she had in her mouth and got onto the bed, presenting her plump round ass.

Opening the bottle of lube, Max gave his cock a nice coating and shuddered as it was still sensitive. He then moved to stand behind the mare and dripped some of the lube in between her ass cheeks. Moving his hand in, he used his pointing and middle finger to rub the lube against her ponut, before pushing them inside making the mare gasp and shudder.

“Heh if two fingers are all it took to make you gasp, then I can't wait to hear what this will get out of you.” Moving his throbbing member to the puckered and now lubed ass, Max pushed the tip in feeling it clench to push it out and hearing Derpy making a loud gasp. “Seems like you might not have let any stallion take this whole. Which means I'll be your first.”

The idea of popping Derpy's anal cherry was too much to resist. Grabbing her tail, he gripped it hard before moving his free hand to hook around her hips. Pulling and thrusting simultaneously, Max forced his shaft into the incredibly tight ponut, making Derpy let out power moan.

Max bit his lips as it had been so long since he felt this level of tightness. “Fuck, so damn tight!” The inside of Derpy's ass gripped him like a vice. If it wasn't for the lube, he'd be incapable of moving his cock.

Catching his breath, he began to thrust his hips, and moaned loudly as he pulled on Derpy's tail. This made the mare moan and grunt her body shaking, as her once virgin ass was now being claimed by the perverted human. Max knew the tail was a sensitive spot for pony's, and he made full use of that knowledge, tugging on her tail each time he thrusted in. Loving the sound of her gasping and moaning, a site he hadn't seen since his days on Earth.

Yet despite being in utter bliss, Max still kept his mind focused on the timer, there was only ten minutes left and he needed to make sure he finished with enough time for her to get dressed. “Derpy, I was you to slam your ass into me until i cum inside you.”

The command was heard loud and clear as Derpy began to push her ass back and forth as hard as she could. The sound of her ass clapping against his body filled the house, along with her moans and groans. “Fuck I can't hold out.” Max quickly grabbed Derpy by the waist with both hands, and held her down as he slammed his cock as deep as he could, before letting a gush of cum fill the mare's insides.

Derpy moaned out as she felt the thick warm cum, slowly coat the inside of her ass, before falling face first onto the bed panting.

Slowly Max pulled his cock out moaning and twitching after the best orgasm he's felt in a long time. The phone vibrated, but he didn't have time to think about it as he had to quickly make his next command. “Derpy, clean yourself off in my bathroom and go put your clothes on as fast as you can.”

He watched as the mare slowly slumped off the bed and walked to the bathroom to clean her hole, as she did, he could see her walking a little funny. Max took great pride in knowing he was the reason.

Quickly getting dressed himself, he ran to the living room to play his part. A moment later Derpy came back and picked her clothes off the floor. As she got dressed, Max recorded her naked form and her putting her clothes on. There were three minutes left. He walked over to her and could smell mint, meaning she used his toothpaste and toothbrush. “Gonna need to buy a new one.”

He joked before leaning in to kiss her lips one last time. “Don't worry baby, next time I'll fuck that pussy of yours next.” He gave her ass a spank and moved back to his room.

The timer ran out, the second it did Derpy's eyes returned to normal, and blinked a few times. “Mmah what h-happened, and ahhh!” She moved her hands to her ass feeling slight pain. “W-why does my butt hurt?”

“Everything alright Derpy?” Maxwell called out as he slowly walked in from the hall. “Did something happen?” he asked, sounding concerned.

The pegasus mare felt confused. Along with the pain her body felt warmer, and almost refreshed? “I-I uh don't know.” She moved her hands away from her flank and tried to make sense of the situation.

“Well maybe you should take a break.” Max leaned in to rub her back, careful not to touch her wings. He picked up the basket with the remaining muffins and passed them to her Derpy. “Here you can have these, it might make you feel better.”

The mare blushed for some reason. Something about the human was different, he seemed somewhat more attractive, and there was a rather pleasant scent to him. “T-thanks, I forgot my breakfast at home.” That made her feel odd saying that, like she said it before.

“Well, we can't have the world's beautiful mail pony going hungry now can we?” He flashed her a charming smile while his hand gently patted her shoulder.

The mare felt her heart skip a beat, something about his tone and the words he used made her feel giddy, and bashful. “Y-you don't mean that. I mean l-look at me.” Derpy knew what many ponies said behind her back, insulting her clumsiness, or how her eyes looked.

Max calmly moved his hand to brush her hair away from her face, and looked into her eyes with a smile. “I am looking, and I meant what I said. I think your eyes make you look cute, and you have a beautiful aura too.”

Derpy's heart nearly skipped a beat, she heard him say nice things about her before, but somehow this time they felt more meaningful. Her cheeks went bright red, and she quickly made her way to the door.

Before she opened it, she looked back with a bashful look. “Um w-when is your next day off?”

Max smiled and hummed. “I should be off this Saturday. Why do you ask?”

She fidgeted in place before replying. “I-I have that day off too, m-maybe we can go out together?” She asked, feeling nervous.

“I'd like that, shall I consider it a date then?” He asked in a charming tone with a playful smirk.

Derpy said nothing but nodded her head, before bolting out the door. All the while Max smirked before looking at his phone.

“20 experience points gained.”

“Derpy’s mind is now slightly weaker to your hypnosis.”

Both notifications gave the human an idea of his progress. “Seems regardless of what hole I fill the points are the same. Not to mention the more I hypnotize a mare, the weaker they will be to resist my hypnosis.” He smiled and made his way to his fridge to grab a bottle of water. “Need to stay hydrated after a good fucking.”

As he unscrewed the cap and took a sip of water, he peaked out the kitchen window, looking at all the mares out and about today. “Not even noon and I already fucked a mare, I wonder who to go after next?”

He thought to himself as he drank the rest of his water, and opened up the notebook app on his phone. “Time to collect some notes and make a list.”

Opening the door, he stepped out of his house, eager to see just who will be a notch under his belt.