The Mail Lady Plot

by OccasionalClopfic

Rating: mature
Tags: Self Insert, Derpy Hooves, Sex, Human, Slice of Life, My Little Pony: Friendship is Magic, Second Person
Length: 3168

When a scantily clad Derpy Hooves shows up at your door to deliver the mail, an interesting opportunity presents itself to you. Soon, you find yourself spending an unforgetable day with the woman of your dreams.

You've always had a crush on the ditzy, but cute and incredibly attractive mail lady of Ponyville, Derpy Hooves. An otherwise boring Sunday takes a turn for the interesting when she shows up at your door to deliver a letter, half-naked and wearing clothing four sizes too small for her. Soon, one innocent question about her current state leads to the next, and you both discover that you are interested in the same, not quite so innocent thing.

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This is a relatively old clopfic I wrote a few months ago, but never got around to publishing anywhere. Going through my old works, I read it again and figured someone might get a kick out of it, so here it is. Hope you enjoy.

Contains: Humanized Derpy on Self-Insert 2nd Person OC, Vaginal and Anal Fingering, Huge Breasts, Milking, Breastmilk-based Snowballing, implied Impregnation, and copious amounts of Porn Logic

Published 2017-04-23 18:40:01 UTC
Last updated 2017-04-23 18:40:01 UTC

Chapter 1

It is a normal, completely average day in Ponyville, and you are half-asleep on the couch in your living room. The sun warmly shines onto you from the window. You’ve done pretty much nothing all day, and are just pondering what you’ll do with your free time, when there suddenly is a knock on the front entrance, interrupting your thought process.

Quickly, you run over to your door, wondering who it could be. None of your friends wanted to visit, did they? Were there any appointments you forgot? You open the door.

Before you stands the local mail lady, and perhaps most gorgeous woman in town, Derpy Hooves. You’ve always wanted to get to know her a little better. Heck, so does everybody else you know. Her body, from head to toe, is just perfect. She is slightly chubby and slightly taller than you, with thick, bodacious curves in all the right places. Her butt is large and jiggly, yet sits firmly in its place. Her boobs are huge, reminiscent of small watermelons, and look as soft and squishy as marshmallows. Atop a warm, slightly pale face of pretty, feminine features rests a head of luscious, beautiful blonde hair, hanging freely down her back. It is wild and enticing, reaching down as far as her behind.

The only thing not utterly perfect about her are her eyes, which stare cross-eyed in two different directions, usually towards the bridge of her nose. But despite this small disability, they are utterly beautiful. Their glowing, golden colour perfectly underlines the innocent kindness and cheerfulness that fills them, and you find yourself falling in love with them every time you see her.

“Special Delivery!”

But this time, something is different about her. Well, not about her, necessarily. Rather, about her clothing. She is not, in fact, wearing her mail lady uniform. She is wearing the top of one, which is at least four sizes too small. It barely covers her down to her belly, and her boobs are successfully trying to push out of it. Her cleavage is on full display, bulging so much that you think they’ll just pop out any moment. And underneath her clothes, you can definitely see her nipples poking against the fabric. Weirdly enough, she seems to have deposited a huge amount of letters between her boobs. Now why would she-

Wait a second.

With how much her boobs are bulging out, you were too distracted to notice it at first. She’s not wearing a bra. Holy Celestia she’s not wearing a bra! Looking down, you notice something else. She’s not wearing any pants either, just having put on a large pair of grey stockings and some sandals. Her bottom is uncovered, revealing, thankfully, some underwear.

However, it is only a thin, white bikini bottom.

You notice that you have got an erection. A really strong, painful one, pushing against your underwear. You now also remember that you are only wearing underwear yourself.

“I’ve got a letter for you!”
Thankfully, she does not seem to have noticed yet. Derpy is kind of a ditz like that. A feature that somehow only makes her more loveable. Oblivious, she grabs one of the letters from her cleavage, and hands it to you. It is warm, and covered in a thin sheen of her own sweat. As you hold it closer to yourself, staring in disbelief, you notice how heavily it smells of her. It seems to be some kind of bill or something, but who really cares? Derpy is almost naked, right in front of you!

As such, you ask her about her clothes.

“Oh, this? I, uh, kinda got up too late? She throws an embarrassed smile as her cheeks flush red. “And I, uh, also forgot my uniform was, uh, still in the laundry. I borrowed this one from Raindrops.

Raindrops. The tiniest woman in all of Ponyville. Sometimes, you really question Derpy’s decision making.

It is now that she notices the letter in your hand is covered in her sweat.

“Oh no! Oh my gosh, I’m so sorry! I had also forgotten my bag, so I had to put my letters somewhere! Is there any way I can make this up to you?”

In your head, visions of porn scenarios flash by, ideas of Derpy falling on her knees and sucking you off as compensation for the sweaty letter, as you roughly grab her by her luscious hair and fuck her throat like-

Your erection twitches painfully, and you desperately clinch your legs to hide it as you whince. An effort which comes too late, as Derpy looks down with her one good eye, the other pointing upwards. Still, they both grow wide in surprise.

“Oh my gosh! You’ve-....you’ve got a boner! This has gotta be so embarrassing! I probably interrupted you and your girlfriend! I’ll think of something to repay you later!”

She already turns to leave when you get over yourself, and tell her to wait. You meekly explain to her that she interrupted nothing, and that you only got a boner because of her.

“R-Really? Oh, it’s probably because of the clothes, isn’t it?” She looks to the floor for a moment, embarrassed. Then, she slightly lifts her head, asking you a weirdly hopeful sounding question. “Do you, uh, really think I’m that pretty?”

You reel back a little at the question. But after calming yourself down, and thinking it over for a second, you say that of course you do. You tell her that there’s nobody in town who’d think anything else.

“R-Really?” she asks, crossing one arm over her breasts and looking away from you. “The last person who told me that was Sparkler’s daddy. I assumed everyone else thought I was….you know…..because of the eyes.”

You tell her that’s nonsense, and that she’s the most beautiful woman you know. In response, she look at you, trembling a little.

“Then do you mind if I….uh, come in….and we could….you know…...I want to help you take care of that.” She points down at your raging boner, causing you to blush heavily. “It’s been a long time, and I’ve only ever did it with Sparkler’s daddy. I’d kinda like to do it again…”

She doesn’t have to say more than that. You pull her into the house, and slam the door shut. Dragging her behind you, you rush back into the living room, causing her to shriek with a mixture of fear and excitement. You slow your roll for a moment, wondering if you’re doing this too quickly, but when you notice the eagerness in her eyes and the smile on her face, you give in to your base desires.

No longer hesitating, you rip open her uniform, tearing away several buttons in the process. You and Derpy will probably get an earful for this later, but you don’t care. Now is the time for pleasure, not worry. And indeed, her uniform pretty much jumps open, her huge breasts forcing their way out of it. The letters that were clamped between them are thrown into the air by the sheer force of it, dropping all over the floor. They are gigantic, each probably as large as your head, as supple and soft as they are big, both topped off with a big, pink nipple. Eager, you start kneading them as you lean in towards Derpy, pressing a passionate kiss on her lips.

She returns it, throwing her arms around you as she kisses you back, soon opening her mouth to push her tongue into yours. Not to be outdone, you do so as well, exchanging a deep, tongue-filled kiss with her as you play with her tits. She tastes sweet, of baked goods and berries, calling to mind her love of freshly baked muffins. And while her technique is rather crude and inexperienced, you love every second of it, playing with her as you do.

Eventually you retreat from her mouth, an action which causes her to look at you with needy, pleading eyes. She doesn’t just want this. She needs this. And the thought of that arouses you even further. You stretch out your tongue, licking from her mouth down to her chin, and then slowly moving down her neck. She shivers at this, giving several small moans. Soon, your mouth laps across the surface of her soft, jiggling tits, caressing them along with your hands. You take in the salty taste of her sweat, the spoils of a hardworking mail lady.

And finally, after slowly making your way down her upper body, you reach them. Her nipples. Her beautiful, thick, bloated nipples. You know that Derpy is a mother. And while Sparkler has already been visiting Ponyville’s kindergarten for a while now, a strange hope fills your mind. Maybe, just maybe, she can still give milk.

“A-...ah….why are...what are you doing…..that’s what Sparkler did….”
Ignoring her confusion, you set upon sucking on her nipples, carefully taking them between your teeth and suckling like you would on a bottle. You even let your tongue slide across them over and over again, playing with them and wiggling them about. Taking Derpy with you, you drop back into a sitting position on your couch, letting her sit on your legs as you fondle her breasts. As she is a bit taller than you, they are perfectly level with your face now, a fact you abuse to its fullest.

You continue to suckle for several more seconds, occasionally changing breast when you feel that you’ve been on one long enough. Derpy continues to shake and weakly moan, occasionally questioning why she is so aroused by this act that used to be so innocent when done by her daughter.

And then, you feel it. Something trickling into your mouth; thin, sweet, and utterly delicious. You have extracted her breastmilk, which goes on to slowly drip into your mouth, but you want more. Increasing the intensity of your suckling, you begin kneading, pressing and caressing her breasts, moving your head rhythmically to pump what you can out of them while you do. Soon, you are rewarded by an ever increasing stream of wonderful, tasty milk, courtesy of the finest looking delivery lady in all of Ponyville.

It appears that she is enjoying herself too. Through her thin underwear, you can feel that her pussy is all but dripping at this point, her juices flowing ceaselessly over your knees. Already, she is starting to rub herself against your knee, desperate to get off. You decide to oblige her.

Removing one hand from her breasts, you quickly cup her ass with it, holding and wiggling it around for a moment, before giving it a short slap. “Eek!” she cries out, though in surprise rather than any real pain. Then, you move your hand to the other side of her body, slipping it under her panties and feeling around until you find her dripping slip. “Oh yes. Please!” she begs, but you don’t need to be told anything. Without a word, you slide in two of your fingers, slowly fingering her wet, gaping folds.

For a few minutes, you continue exploring her slimy, slippery caverns with your fingers, pushing in and out in a rhythmic pattern, all the while slurping down delicious breastmilk from the soft mountains of flesh in your face. You only stop when, eventually, you hear Derpy speak up again from in-between her soft moans.

“Oh my gosh. Oh my gosh! I’m cumming!”

An idea pops up in your head. Quickly, you take one last, huge sip of her milk, draining her boobs of all that you can. You don’t swallow, instead carrying it in your mouth, slushing it left and right, taking in its taste and texture. Then, you lift up your head, look Derpy straight in her mismatched eyes that are already twitching from the pleasure of her approaching a powerful orgasm.

“What are you-”

Not hesitating one moment longer, you press a deep, tongue-heavy kiss on her lips, pushing her own breastmilk into her mouth and letting her have a good taste of it. In this arousing, yet clumsy effort, much of the milk drools down her lips and her chin, getting all over her already torn uniform and onto your knees, but enough enters her mouth for her to notice the taste. And in that moment, your fingers finally push her over the edge and into a full-blown orgasm. She jerks upwards, jizzing hard over your hand while your tongue and her own breastmilk fill her mouth, the perversion of which causes her to freeze with pleasure.

When her orgasm subsides, her form collapses a little, weakened by the event. She pulls back, ending your kiss, though she manages to keep most of the milk in her mouth. You look each other in the eyes, horny and full of excitement. Then, she swallows her own milk with an audible gulp, and for a moment you swear that her eyes drift even further apart than they usually do. After that, you just look at each other for a while, Derpy basking in her afterglow, you with a raging erection pressing against her belly.

“I….haha….I had no idea my milk was so tasty…..maybe I should have it again with some muffins!....” A goofy smile spreads on her face and she hugs you, pressing her warm body against yours. You feel her soft skin snuggling up to you, and smell her slightly sweaty, slightly sweet smell.

You allow her to catch her breath for a few moments, only disturbing her to ask if she liked it. Her answer, despite its breathlessness, is very clear. “Y-Yeah….That was awesome…”

Eventually, she recovers a little, and she lifts her head to look you straight in the eyes. “Do you want me to take care of you too?” With her dainty, unmanicured fingers she points down at your still raging erection. The only answer you know to give at this point is a wantful nod, which she giggles in response to.

Then, she jumps off your legs, standing on her own two feet again. Smiling brightly, she swiftly pulls down her panties, kicking them off her feet in a hurried motion. With them out of the way, she jumps onto the couch next to you, crawling on all fours. She is turned away from you, her huge, jiggly butt pushed in your direction. She is presenting herself to you. Her tight, puckered asshole above, and her gaping, leaking pussy below.

You don’t have to think for one second. Moving just as quickly as she did, you get up, pulling down your underwear and throwing it somewhere onto the floor. Your freed erection bursts out much like Derpy’s tits did earlier, and you quickly line it up with her entrance, no longer patient enough to do any real foreplay. She’s had her turn. Now you want yours.

With one powerful push, you shove its full length inside of her, extracting a loud, throaty moan from her. “Owwwwww…..so good….” She is tight. Despite the plentiful lubrication provided by her wetness, despite the fact that she’s a mother, despite the fact that her pussy was gaping so widely to take you in, it is still extremely, wonderfully tight on its inside. Every nerve in your cock feels like it’s being stimulated at once, her insides rubbing all over you and embracing you with their strong grip. It is amazing, even better than you imagined all those times you jerked off to the idea of doing Derpy.
You make your initial thrusts, going slowly at first. This is an experience you want to savor, to use to its fullest. Maybe, if you do well, you’ll get to do this again sometime in the future. But even so, nothing will compare to experiencing her for the first time. Feeling her squeeze on you, you slowly pull out, all the way, until your dick is back out in the now seemingly chilly air of your living room. Then, at a just as glacial pace, you push back in, moving forward until you’re hilted, balls deep.

“Oooohhhhh….you’re filling me….can you go faster…?”

Nope. No, you can’t. Waggling your finger, you point out that she still owes you for that sweat-covered letter, causing her to gasp, before settling into a bashful smile. “Hehe.
I guess you’re right. Just please don’t do this for too long.”

As a matter of fact, you don’t. You manage to endure this slow pace for another minute or so, during which you extract several almost pained cries of pleasure from Derpy, but eventually you find yourself settling into a quicker pace. You grunt in primal joy as your balls slap loudly against her, and you find yourself grabbing her wild, flowing hair and pulling on it, dragging her head towards you. Of course, you don’t do it hard enough to hurt her, and she does seem to enjoy the rough nature of this action, as she goes on to beg you to fuck her harder.

So, you do, going faster, ever faster, speeding up with every passing minute, your animal-like sex reaching a loud crescendo. Another idea hits you. You let go of her body with the one hand that is not pulling at her hair, and quickly slobber its index finger with your own spit. When it is all lubed up, you use that hand to stretch apart her buttcheeks. And then, in a motion as swift as the one you used to push your cock into her pussy, you shove your finger into her asshole, making her gasp.

“So slimy…..ack….so weird..”

You start fingering her again, in her asshole this time, as you continue to fuck her as fast as you can. This way, you continue for several more minutes, your mind absolutely blank with pleasure, and only sounds that are filling the room being your grunts and moans, and the wet slaps of your bodies smacking against each other.

Then, you feel yourself tensing up, your cock twitching heavily. You groan one last time with pleasure, and then shoot your load inside of her, as she too screams loudly, indicating that she herself has reached a second orgasm. You shoot the thickest, heaviest load of your life, filling her up to the brim, and when you finally come to a stop your own cum is trickling from her cunt past your dick. You both collapse onto the couch, breathing, your cock still inside of her. Wrapping your arms around her, you give her a few happy kisses on the neck, and then on the mouth as she turns her head to look at you.

A strange thought settles into your head, and look at her, you feel like she’s wondering the same thing. That was wonderful. But…..you didn’t use a condom, did you? Yet, the innocent, happy smile on her face removes all the worries you have.

“Do you think Sparkler’s gonna get a little sister now?”