Milking The Milkmare
Chapter 1: The Milkmare Of Trottingham
Load Full Story Next ChapterIt’s been a long while since you first traveled to Trottingham. The last time you visited, was when you were just a little boy, traveling the world with your parents. You don’t remember much about it, only that the air, the atmosphere, and the inhabitants seemed very peaceful. You also remember there not being as many humans in the town. Unlike Baltimare and your hometown of Applewood, Trottingham had way more ponies than your own kind.
Now, you have arrived. Off the train station, and into the town. You always wanted a change of scenery, being stuck in cities for most of your life, save for the now defunct family trips, you figured it would be nice to just see something more calm and tranquil than what you have been experiencing for the past decade.
Trottingham is even better than you remember it. That familiar scent of apple pie and roses rise into your nostrils, and you take it all in without a second thought. You walk through town, carrying your suitcase alongside you. The thing only has the necessary essentials; toothbrush, toothpaste, clothes, socks, underwear. Really, you only plan on staying in a motel for a couple of days before moving on to the next town. You notice more humans than you last remember, hanging out with various ponies. What’s even more curious, is that some of them appear to be couples!
Now, human and pony relations are not exactly uncommon for you, but you were raised by a family who forbid such behavior; parents that were part of rallies, and tried to pass that ridiculous law of making it illegal. You held your tongue during those years, silently nodding your head, when they would ask for your thoughts. But in all honesty, you really did not share the same opinion as they do. While the most common argument against this kind of coupling, is that the two species cannot create life together, who are you to judge what the heart wants? Same sex marriage never bothered you, why should human and pony relationships?
You spot a motel. It doesn’t look like the Ritz, but it does promise comfortable beds, room service, and the best television programming Trottingham had to offer. Plus, it looked relatively inexpensive, and it's only for a couple of days anyway, so why not?
As you inch closer to the motel, you hear the sound of paper bags being dropped, and a pained moan not too far away from you. You turn around to see a yellowish mare with a blue mane, hunched on the ground, barely able to move. On instinct, you run up to her.
“Are you okay, Miss?” you ask. Always the best thing to start off with. She shakes her head, something is definitely wrong, but she can barely get the words out. “Are you hurt? What’s wrong?” You ask more questions in rapid fire panicked succession.
“I...I have to get home.” The mare says in a near whisper.
“Are you sure? You don’t need to go to a hospital?”
“No.” she shakes her head once more, “I just...need to get home.”
You ask where she lives, and she weakly tells you the location. She was in no condition to move, so you hoisted her on your back, grabbed her groceries, and your suitcase, and carried her to her home. You’ve never done anything quite like this before, running around with a pony on your back. You're no stranger to rough housing with ponies, especially in your former middle school days. But this? Never.
A couple things have caught your attention. One being that you are wondering why she’s in so much pain, and two is wondering why it feels like there are two large soft mounds of something pressing up against your back. She didn’t appear to be holding anything else. No time to think, it's time to go. Besides, it's been a while since you've carried something of this weight, and your legs are ready to give at any moment.
You get to her home, which looks like a nice little place, and open her door. The house was unlocked, which was surprising to you. You figure the possibility that everyone knows everyone in this town, so the prospect of burglary is slim to none. Inside is a cozy looking living room, and a couch that seems like it's seen better days, but hasn't lost its comfort.
“Couch…” she says. You back up, and set her down on the couch in the living room.
As you turn around to ask her what she needs, you notice fairly quickly why you felt that unusual pressure on your back. The mare has unusually large mammary glands centered around her crotch. They could almost pass for human, if they weren’t located down there. Your eyes cannot help but be drawn to them for a few brief seconds, before you realize that you’re supposed to be helping this poor girl.
“What do you need?” you ask. You list off any possible solutions; water, medicine, the toilet.
“A bucket.” she answers. You assume she wants to vomit, and offer to take her to the bathroom. She refuses, demanding that you get her a bucket. Whatever pain she’s in, it’s reaching its breaking point. It's not hard finding the bucket; as it's in the middle of the kitchen. You set it down in front of her, waiting for what she wants next.
“The next part…might be a little strange.” she tells you.
You raise an eyebrow. What could she possibly want that could be so....
“I…need you to milk me.”
Yeah, okay. You almost fall over from hearing that. Almost. The only thing keeping you from doing just that, is your absolute shock.
“I’m sorry…what?” you ask. This couldn’t be happening. You just met this mare, and now she’s asking, no telling, you to milk her? From THOSE?!
“Please…” she puts a hoof on your shoulder, “I can’t...I can’t do it by myself now. Ah!” She grimaces in pain, hissing through her teeth.
You look down at those teats, and then back up into her pleading eyes. Surely, there was someone or somepony more qualified for this job than you. Maybe her husband, or coltfriend, or boyfriend…or the female equivalent of all of those. Then again, if she trusts you enough to do this, maybe there isn’t one of those in her life, giving her no choice.
No more time for thinking, you have to do this! Reluctantly, you slowly bring your hands to those large mammaries, and clamp your fingers onto her nipples. She gasps in pain…or pleasure. You don't know, and almost hit yourself for thinking the other option. She's in pain, you perverted fool! Help her!
You squeeze one nipple carefully, and a stream of milk suddenly shoots out, onto your shirt.
“Shit” you thought to yourself. Good thing you have spare shirts in that suitcase of yours. You look back at her, she doesn’t look any better. You aim a teat closer to the bucket, and try again. Direct hit. Much better.
Once you have a good grasp on things, you begin to milk. It's actually no different than milking a cow. Each squeeze brings out a surprising torrent of milk. Her heavy breathing gradually subsides with every passing moment, becoming more like sighs of relief and relaxation. The bucket fills up rather quickly, teetering on the edge of spillage, but she taps you on the shoulder, giving you the okay to stop, which you gladly do. Spent, she leans forward, and rests her head on your shoulder, calming down as normal breaths escape her lungs.
“Thank you…” she whispers.
“Uh..yeah…no problem.” you say, patting her on the back.
You move her off your shoulder and her muzzle brushes against your lips, which gives you great pause. With a tactful head-shake and throat clear, you ignore it, and excuse yourself to the kitchen, offering to put her groceries away, after you wash your hands. She allows you to do so, and tells you where to put everything. Her speech is more normal, and less painful. You wash your hands, put her groceries away, and get her a glass of ice cold water. You walk back into the living room, and spot her watching The Ponies Court on the television. You smirk, before giving her the water, which she happily takes.
Not one to want to just bolt out, you sit down next to her, and watch the program with her; keeping an eye on her just in case the pain returns. She smiles, as the court case you two are watching gets more argumentative, and more hilarious.
“You watch this show too?” she looks to you and asks.
You nod, and tell her that you watch the show on the days where you had nothing to do, and marveled at some of the stupidity the individuals get themselves into. You tell her that it’s more entertaining than The People’s Court, which she agrees with you wholeheartedly. You look down at the bucket of milk, and ask…
“So…when is the baby due?”
She looks at you, confused by your question. You tell her that you assume that she is pregnant, which is why she is producing milk. She laughs. That probably wasn't the right assumption, dummy.
“You’re not from around here, are you?” she asks. You shake your head with a chuckle. “It’s my…special talent.”
“Lactating?” you ask. A very odd special talent, to be sure.
“If you want to put it that way…yes.” she blushes, “I produce more milk than any cow, but one of the side effects are these…things.” she looks down at her large teats, “The other is that I have to be milked twice a day at a set time. I left the house an hour before my daily milking, thinking I had enough time. Well…you saw how that turned out.”
“I’m sorry.” you tell her, “I can’t imagine what kind of pain you were in.”
“It’s alright.” she assures you, “I’m normally not this reckless. This has only happened one other time.”
You ask her about this past event. She tells you that the last time it happened was a couple years ago, but nopony helped her, and she had to milk herself in the middle of Trottingham. She was embarrassed for quite a while after that. You let out another “I’m sorry” again, but she tells you to stop apologizing for things that aren’t your fault.
“I can’t help it.” you tell her, “It’s in my nature.” You look back at the bucket before asking “What do you want me to do with this milk?”
“Put it outside. The local cats like to come down here.”
“Is that what you do with the milk?” you wonder, “Give it to cats?”
“No.” she giggles an amusingly cute giggle, “I own a dairy in town. It’s called Milky’s Way. Like my name.” You smirk, while she remembers that she didn’t properly introduce herself. “Oh my gosh, I didn’t even tell you my name before that. My name is Milky Way. What’s yours?” You tell her your name. “Huh, that’s not the name I would have guessed, but it’s a nice name.” she smiles, “So, what brings you here?”
You tell her the cliff notes of your life story, all the way to the events of today. You tell her almost everything in an abridged version, from your upbringing, to your plans for the future. You felt yourself getting bored by your own tale, but she didn’t seem to mind as much. You tell her that you can stop at any time if she feels bored, but she says that she is perfectly fine. By the time you are finished she compliments on how exciting your life is, even though you don’t personally think so.
Evening approaches during your conversations, and both your eyes start to get heavy. She yawns, and thanks you for staying with her for so long, even if you didn’t need to. She tells you that it had been a long time since she had many visitors come to her house.
“Why?” you ask. “You seem nice. It’s because you’re a serial killer, isn’t it?” you joke. She laughs.
“No. It’s because of…well…look at me.” She’s obviously referring to her teats. “These aren’t natural. I guess that scared a lot of ponies off.” She looks at you. “You think I’m strange too, don’t you?”
You shake your head in disagreement. “No. Not at all. You seem like a perfectly normal pony, aside from THAT...” you glance down for a second, ”...but, it doesn’t bother me.”
“You’re just being nice.” she teases, sure that you are lying to her. You're not.
“No, I’m serious.” you say with the straightest of faces. “Sure, it caught me off guard when I first saw them, but weirded out? Nah. I’ve seen weirder things, believe me. I think that…well…for a pony you’re pretty…cute.” You blush at the admittance. You can't help it. Though you've only known her for a couple of hours, you have already become accustomed to her company. You wouldn't mind staying for a bit longer, that's for sure.
She smiles, and gives you a soft chuckle. Suddenly, she leans her head against your arm. You hear her relax, as her mane rubs against your flesh. Woah... wait a second.
“Why can’t all guys be like you?” she wonders. Your cheeks are flushed with red in a matter of moments. Is this really leading where you think it is? No, it couldn’t be. That's just you being silly. “You’re such a gentleman; even more than most colts that I have met.”
You start believing that this is some crazy dream that you are having; that you are still on that train to Trottingham, and will simply wake up before it gets really interesting, like most dreams tend to do. That’s when you feel it; her hoof making its way under your shirt, caressing your bare skin underneath. Oh, boy.
“Have you ever been with a pony before?” she asks. You shake your head, still wondering where this is all going. “I’ve always wondered what it would be like with a human man. Now that you’re here…” She moves her way onto your lap, straddling you. Her breasts pushed against your stomach. “Maybe I can find out…if you’re up for it.”
“Okay, maybe this IS actually happening.” You think to yourself. “This is usually the part where I wake up, but…”
"Oh my!" she looks down at the wet spot on your shirt. "I seem to have gotten some of my milk on your clothes. I'm so sorry. Let me take this thing off..."
She puts both her hooves under your shirt, and lifts it up, removing it from your upper body. “Yeah…this is real.” You tell yourself, as she feels your chest.
“Don’t move.” she says sternly, “I just want to try something.” She pauses, thinking about her actions. Slowly, she leans in, opening her mouth for a kiss. As if you were on autopilot, you open your mouth instinctively, and the two of you make contact.
It’s a long kiss, a long sensual kiss. It takes a while before your tongues touch each other, and lap up one another. You never imagined in a million years that you would find yourself lasciviously making out with a pony, but you did always wonder what it would be like. Besides, with your parents prattling on about how abnormal it was, you couldn’t help but think about how bad it could have been. Turns out, it's not bad at all. Turns out, it’s actually quite good.
She separates her mouth from yours, and a trail of saliva connects your two mouths together. Neither of you think to wipe it away, instead looking into each other’s eyes, taking in what you just experienced. She moves her tongue around her palate, as if evaluating the aftertaste of that kiss like fine wine. The question on your mind is; will it be perfectly aged, or horrifically spoiled? Painful metaphors aside, she comes up with an opinion.
“Not bad.” she says with a grin, “Let me try again.”
She dives right in, this time with much more force. All you can think about was how amazing of a kisser she is. How could she have NOT had any potential suitors during her time in Trottingham? She was even better than most human women were at this kind of thing! Your hands travel down her back, reaching her shapely rump. You grab onto it, giving it a hard squeeze. She squeals with delight at your very touch. You can feel her grind herself against your crotch, making the eventual erection in your pants hurt like all hell. She stops the kiss and the grind, feeling your length rubbing against her.
“Oh?” she says with curiosity, “Really?” She looks surprised by the fact that you are utterly turned on by this, and so quickly too. “Well, I think I have to do something about this.” She looks at her hooves, then back at you. “Do you mind?” she glances at your crotch, “I don’t have the luxury of fingers.”
In an instant, you move your hands down underneath her breasts, as you reach the zipper. You pull the zipper down, and bring out your erection for some air. She parts her breasts to look at your length sticking straight up in-between her teats. She licks her lips in anticipation, and you feel a warm wetness on your lap. You can take a couple guesses as to what it is, but you’re only going to need one.
“My my my.” she says softly, “I believe it’s time I pay you back for all your help.” She raises herself up, her stomach meeting your face, and breasts heaving on your neck. “You milked me, I suppose it’s only fair that I milk you.” Your eyes widen at that impossibly cheesy yet erotic statement, as she slams herself down on your cock, forcefully invading her hungry moist sex. Perfect aim.
You both gasp in shock upon entry. You cannot believe how tight she is, even with all the wetness you felt on your pants. It’s an indescribably amazing feeling. She chuckles and moans in immense pleasure, feeling every inch of your length inside of her. You both look into each other’s eyes, and slowly, she begins to ride you. Your shaft moving up and down inside of her, slowly thrusting in tune with her grinds.
“You like this, don’t you?” she asks. You nod rapidly. “I bet your folks would be pretty mad, if they found out, wouldn’t they?” You chuckle, as you keep on plunging into her.
Your heavy breathing becomes moans of euphoria, as her grinding become faster, and your thrusts just a little harder. You want to go on longer, but you just can’t. The fact that ninety seconds have passed is amazing enough. You can already feel the pressure building inside of you. Her tight walls clamping down, refusing to let you go. Your moans become louder, and so do hers.
“I-I’m…I’m gonna cum!” you tell her. She doesn’t slow down, she wants you to cum. She wants you to cum hard, and inside. “Oh god!” you shout. You feel like you’re going to explode at any moment. She rides you even harder now. It’s too much to bear. “I..AHHH!” You grab onto her, pulling her in close, as one final thrust is enough to push you over the edge. The dam inside you bursts, and you spurt load after load of your hot cum inside of her. She can only breathe heavily, and giggle, as she feels your seed flow into her. After what feels like a five minute long orgasm, you finally stop.
“I…I’m sorry.” you say to her, “I wanted to go longer. But…”
“Shhh…” she quietly says, caressing your cheek. “Don’t worry about a thing. We haven’t even started yet.” She gets off of you, your length sliding out of her slit, drops of your seed pouring out. She lays down on the couch, spreading her legs, exposing her sex for you. “Now it’s your turn.”
She looks at you with sultry eyes, awaiting your next move. The most obvious thing she wants you to do is eat her out, but you have a better idea. You lean down, past her sticky sex, and grab onto those bountiful mounds just above. She gasps in surprise, as you gently massage her teats. But, that’s not good enough; not for you. Not even close.
Instantly, you wrap your mouth around her left nipple, causing her to moan with pleasure, and you commence sucking the milk out. Though you had drained enough milk from her to stop the pain, there was still plenty to go around. Sweet, sweet liquid shoots out into your mouth, and the taste is mouth-wateringly good the moment it hits your tongue. All you want is more. You alternate between teats, sucking out all the milk, massaging her breasts at the same time. You glance up to look at her, and she’s in absolute heaven.
“Yes…oh yes!” she screams, “Keep going!” You do so. Your member begins to stand at attention yet again, almost ready for another round. Just to sweeten the deal, you insert your fingers into her slick and ready sex. “I can’t believe it! I-I’m gonna cum!” She announces. You continue sucking, moving your fingers inside her slit. “Oh my…nyah!” You have your last suck, when she lets out a powerful orgasmic moan, her walls pouring out a wave of her thick juices. You open your mouth and let it all in, the taste being as sweet as the milk from her teats.
“That was amazing…” she says under her breath. You’re not done yet. You are as rock hard as you have ever been, and there’s something else you want to do.
You unbuckle your pants, and take them off. Now you’re as naked as she is. You position yourself, like you’re about to go missionary on her, but that’s not what you’re doing. Not yet anyway. You place your shaft in between her breasts, and push them around your length. She looks at you with a grin, knowing what you are planning.
“Dirty…” she says slyly, enjoying every moment.
You start thrusting. She moans with every pump you deliver. Her soft mounds, coupled with the sweat she had sustained, make the feeling of her mammaries around your cock astounding. You go faster now, and her moans become more pronounced.
“Sweet Celestia!” she yells, “Why didn’t I think of this before?!”
Suddenly, you stop thrusting. She looks at you in confusion, eyebrow cocked up.
“W-why did you stop?”
Without warning, you pull your shaft from between her breasts, and drive it back into her moist sex, and begin pounding her with all your might. She lays her head down, and screams in pure bliss. She is still incredibly tight, but you are ready for it. You have learned to keep control when inside her.
“Nyah…don’t stop!” she wails. You flip her on her stomach, shaft still inside, and you continue thrusting. You lean down, and kiss her neck. She leans up, and invades your mouth with her tongue. You grab onto her breasts, squeezing them tight, as you continue to pound into her, hammering against her perfectly round plot. You can only hope that any passerby cannot hear what is going on inside the house. You even glance at the window for a brief second. No one and no pony is watching. Good.
“Have you…ah…ever had a-uh…marefriend before?” she manages to get out between moans.
“No-uh! But I’m-ah…warming up to the ide-ah!” You see her smile, glad at what you just said.
“I-I’m cumming again!” she says, “Put me on my back!” she demands of you.
You’re not one to disobey an order, so you flip her onto her back, and you stare into her eyes, as you pump into her further, her breasts heaving up and down during your throes of uncontrollable passion.
“Th-That’s better!” she smiles.
Looking into her eyes, you feel that familiar pressure building up into your loins again. It’s even stronger than before, it’s almost unbearable.
“Y-You’re cumming too, aren’t you?” she asks. You nod. “Let’s do it! The same time! I’m almost there!”
She grabs onto you, wrapping her legs around your hips, shoving your shaft deeper into her, making you barely able to thrust the same as you were before. Your eyes widen as you feel the pressure build up faster now, you fight to keep yourself from cumming; not until after her. She holds onto your face, and brings you in for a nice sensual kiss. That’s enough for the both of you. Her walls clamp down hard onto you, and you explode into her, as her juices soak your cock. You both open your mouths wide, and exhale a loud moan into each other during the longest, hardest orgasm you two have ever experienced. Both of your fluids burst from her parted slit, and pool onto the couch.
Finally, both of you subside, and you lay on top of her, keeping you softening length inside her…just in case she isn’t completely ready to stop. The two of you are drenched in sweat and satisfaction, breathing heavily from everything that you did.
“You know…” she breaks the silence, “This wouldn’t have happened if you didn’t milk me…and I mean that in a good way.” You chuckle in response. “How long are you planning on staying in Trottingham?”
“A couple days.” you answer, “You caught me while I was looking for a motel.”
“Well…your stuff is already here. How about you stay with me for a little while?” You look up at her. “And…I could use the extra help around the store.” You smile. She smiles. “One condition; you do it the same way we just did, from here on out.”
A perfect compromise.
“I…I guess I could stay in town a little bit longer.” you tell her. The two of you laugh, before going in for another passionate kiss.
Say hello to your new home. You’re going to be living here for quite a long while.
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