Derpy Hooves' Rocky Evening

by Steel Quill

Rating: mature
Tags: Porn, Rockhoof, Derpy Hooves, Slice of Life, Sex, My Little Pony: Friendship is Magic
Length: 8783

Derpy works hard to make ends meet. Sometimes that work involves work she doesn't talk to Dinky about.

It can be said for anypony living in Ponyville that in one way or another, you know Derpy Hooves. She's the cute mailmare who brings you your packages. She's the pegasus with bubbles on her flank and muffins on her mind. All this is true, but there's more to her than meets the public eye. In a life where you're a single mother trying to give your daughter the good life you didn't get to have for yourself, you do whatever you can in order to make it happen. It means some sleepless nights out in town. It means doing things you told yourself you'd never do unless you absolutely had to. But through it all, Derpy does her best because she has to.

By the end of tonight, she just might feel better about the whole thing. And not be left asking "what went wrong" when something finally goes right for once.

A rough piece to show I'm still alive and writing, just occupied with various projects. I was motivated to write something positive for Derpy, and so here it goes.

Artwork by Moonlitbrush. Pre-read by Graymane Shadow! Edit 3/26/2021: Featured same day! Thank you!

Tags: MxF, Feral ponies, Escort work, unexpected pairing, tender moments, vanilla sex, cunnilingus, huge male endowment, large insertion, cum inflation, creampies aplenty, fun positive sex, happy ending.

Published 2021-03-26 19:50:01 UTC
Last updated 2021-03-26 19:50:01 UTC

Derpy Hooves' Rocky Evening

It was another night in Ponyville, the crowded but pleasant country town that was home to more magic and royalty than you could shake a stick at. A Princess of Friendship, Elements of Harmony, more visits by the Royal Sisters than you could count; it leaves a pony wondering if somepony swapped the profiles of Ponyville and Manehattan or Canterlot. You could scarcely go anywhere in town without bumping into somepony of high social importance. But over time, you got used to seeing them, and most would treat them with the same casual care and relaxed air as a simple neighbor. They tended to appreciate that, especially given how chaotic their days can be.

But while those higher class ponies did have everything they could ever want or need in life, the normals among the populace still had needs to see to. They had jobs to work, bills to pay, fillies and colts to feed. It was why Derpy Hooves was waiting in the lobby of one of Ponyville’s casual restaurants, but she wasn’t there as a server, a cook, not even a janitor. No, Derpy’s purpose was a little more adult than the basic part-time setup other workers there would have.

With such high value and highly regarded figures walking among Ponyville’s populace, it wasn’t long that some elements of less family-friendly repute snuck into town and set up shop. One such line of work that seemed to swell overnight was the escort service. Of course, Ponyville being Ponyville, you couldn’t expect things to be as seedy or questionable like in places elsewhere. In fact, sometimes, the business itself wound up finding itself booked more with wholesome, genuinely innocent requests than the lascivious and raunchy one might expect. Some just wanted a companion to walk with them, to bend an ear and let them be heard.

Derpy would never have expected to fall so easily into the rhythms of the business of being an escort. All she saw herself as was a mare working to give her daughter Dinky the best life she can despite being a single parent. Sometimes things worked out swell, and she felt like she had a grip on her life. Other times would leave her relying entirely on just how unburnt the toast she’d left in the toaster was as a measure between life being good and everything being bad. When she’d heard the whispers about the escort business, she had at first dismissed such ideas as something she couldn’t try.

But then Dinky needed more money for school. The grocers started charging higher prices for their goods. The mail service started to hire more ponies to keep up with demand, and her hours were spread out. It was thoughts of making sure Dinky was happy that pushed Derpy to finally inquire into the business, and to learn the ins and outs of being an escort.

The first trick of the trade? Know how to hide yourself if you’re a known face in town. Not the easiest thing for the “Muffin Mailmare of Ponyville”.

‘I hope I did everything right this time.’ Derpy thought to herself as she looked at her reflection. It certainly wasn’t Derpy Hooves looking back. Derpy Hooves didn’t have oak brown hair brushed this well, a silvery coat that looked soft as silk, or an elongated tail. Gods, she wished she had that long a tail, it’d be so neat and pretty! Even her cutie mark was disguised, replaced with a simple stack of books. All thanks to a simple magic disguise bracelet the business had given her. She’d used this librarian ponysona a few times, and so far, it’d worked out fairly well.

...except for the one time she’d actually been paired with an actual librarian at Ponyville library. That had been interesting to play out.

“Miss Hoofsy?” A male voice snapped Derpy out of her daydreams and she turned to look at the maitre’d standing nearby. To him, she was looking with both eyes. But behind the magic cover Derpy had on, she was seeing him, as well as the floor to his left.

“Y-yes? Sorry, my mind was elsewhere.” She said.

“Your table and guest are ready, madame. The back corner, as requested.” He told her, offering a smile. It was a knowing smile; she wasn’t there just to indulge in some salad. “Shall I lead you?”

“No that’s ok! I’m familiar with things enough. Thank you though!” She assured him before going on her way. Once far enough away from the stallion, Derpy allowed a disappointed look to cross her expression before she could help it. That particular maitre’d knew what she was doing, and knew the business she was employing. He’d employed it himself once, though Derpy hadn’t been his escort. Word through the grapevine though was he fancied himself as a fantastic lover, yet couldn’t even get Roseluck to climax once.

Wandering to the back corner of the restaurant let Derpy’s mind wander to her own encounters behind closed doors. They were...far and few between. It wasn’t that Derpy didn’t know what happened in a bedroom, but more that the bedroom always led to one accident or another. One stallion wound up knocking himself out when she’d tried to rush and wound up sitting on his head harder than she’d expected. A mare who wanted to try a fancy new sex toy discovered how much voltage the batteries had when drinks were spilled on them. Funny enough, she seemed to actually enjoy the shock before falling unconscious.

“Maybe this time, it can go better. I can do this. He might just be an old timer noble wanting a pretty mare to sit across and spend time with him. That happens. Right? Right.” She muttered to herself as she entered the enclosed area of the restaurant, half obscured by glass and furniture save for an open entryway left deliberately without doors. It was considered a more romantic setting than out in the regular public space, some dates taking advantage of the space to be especially loving, or just wanting the spot to swap spit without judgment in public.

Stepping inside, Derpy was surprised to see that she was the only pony present. Given the time of day and with it being the weekend, such a space usually had a few extra occupants. She looked to her left and saw there was indeed one pony in there waiting for her. But it took a couple extra blinks to see that the pony inside was real, despite being so...huge.

“E-excuse me? Mr...Rockhoof?” she tried.

The behemoth of a stallion turned at being addressed. His face bore a rich goatee and beard that ran along the border of his jaw and cheeks, matching the faded orange mane he had atop his head. It looked carefully groomed, as if somepony had managed to force the hairs to behave and not fan out wildly. There were a couple lighter streaks along his hair, dashes of fading yellowish white, signifying his age. His grayish cyan coat was trimmed short, and looked clean. He had put in a fair bit of effort himself for this, like she had done. Granted, hers was done via a magic bracelet, but the thought still counted in her head.

More occupying Derpy’s mind in the moment was that the stallion was just...massive, in every definition. Broad chested, wide shoulders, and with enough heft and bulk to occupy a whole restaurant bench by himself. The wooden seat creaked in relief as he got up from it, approaching her. He seemed to loom over her, shadowing himself due to the light overhead being blocked by his head. She wasn’t sure how to react, until he reached out and took her hoof in his gently.

“They told me to wait for a flower to wander into the room. You’d be the first bloom of the day I’ve seen. Miss...Hoofsy, is it?”

The gentleness in his grasp defied the strength that radiated off of him. It was him. It was Rockhoof, a Pillar of Equestria pulled from Limbo and legend into real life. She managed to weakly return his grasp and nodded.

“T-that’s me! Miss Hoofsy. Or just Hoofsy if you prefer.” ‘They gave me him? Him?! I don’t know how to entertain a legend!’

As it turned out, keeping a pony like Rockhoof entertained was actually a lot simpler than she’d imagined.

When being taught the tricks and lessons escorts have in their repertoire for entertaining a client, Derpy saw herself doing best in handling small talk, being a good listener, and being a pleasant presence for the pony in question. Knowing this and making it part of her escort listing is what helped to give her clients that wouldn’t be difficult for her, instead of a mismatched pairing that would leave both parties dissatisfied. It helped being a social pony herself outside of the business: the mailmare was the one pony who usually got a peek into just about everypony’s lives, public or private.

Rockhoof was an anomaly to all this experience, but in an unusual way. The listing given to Derpy had stated he wanted company to occupy his time and to be a friend. Nothing else forced or demanded otherwise. Of course, everything was still kept on the table as an option in this line of work, but Derpy – or Hoofsy as she was – wasn’t sure what fit that bill when it came to him. I mean, how do you keep good company for a pony whose legend is known to everypony and who’s actions literally helped shape the world you lived in today?

Apparently, explaining the silly day to day things of Derpy and her filly did the job plenty.

“And so this teacher believed these little...blocks, will teach the child how to count?” Rockhoof questioned as the two walked together. They’d left the restaurant a few minutes ago, full bellies and happy spirits carrying them into the world outside. Derpy did her best to keep her attention entirely fixed on Rockhoof; her disguise made this easy, but past it, she had to push down the habit of watching two different views simultaneously like she was so used to.

“Uh-huh! A lot of kids start out using those. A sorta hooves-on thinking kind of thing.” Derpy told him. She stayed close to him, obeying the first lesson to the letter: keep near your client always. They wanted you for a reason, so keeping within hoof’s reach was important to maintain. “What was it like for you, back in the day?”

“Well, I can tell you this much: if you could count beyond the lot of lads and lassies in your home, you were considered a clever pony.” Rockhoof replied, urging a giggle from Derpy. “Things are a lot more hooves-on now than in my time. A lot less chaotic too. Funny considerin’ I just saw Discord in the park two days ago.”

“Did you ever meet Discord before in the past?”

“Ha! That old Draconequus was a fuss of a mess. He seemed to always be ahead by three steps, but it never stopped us from doing good for others or fixing the chaos he left behind him.” Rockhoof told her. “He’s the reason the Minotaur nation both like and dislike mazes.”

“Really? Why?” Derpy questioned.

“Well, they dislike it because of the old stories being all folks know about them. That and being considered violent behemoths. But they like the mazes because it’s theirs. You can ask for many a guide into a maze, but a minotaur will never let you get lost in one.”

Derpy nodded at the concept. “It would hurt my eyes too much to be in a big maze. Even the hedge maze out by the park makes me dizzy.” She said before catching herself and looking back up at Rockhoof who was watching her. “T-too many turns. I’m sometimes bad at directions. Ehehe.”

“Oh, you’re tellin’ me! All these new roads and street names. It used to be just ‘oh, you’ll find so and so down the road, the hut with the vegetables out the side’ and so on.” Rockhoof waved a hoof about them. “If you asked me to point you to Town Hall or Cherrybuck Lane, I’d be spinning circles!”

The brown-maned mare giggled at the idea, evoking a laugh from the bulky stallion as well. With Celestia’s sun lowering on the horizon, the pair were treated to the sight of the castle as the sun’s glowing rays gleamed off it’s reflective surface, while it’s shadow stretched far into the distance. Derpy had to remind herself the stallion she was with did indeed still live at the Castle of Friendship, as might be expected for one of his station.

“She’s a right beauty, ain’t she? Looks almost like a Hearth’s Warming tree all lit up, but without the snow.” Rockhoof commented.

“O-oh! Certainly! It must be a nice place to live.” She replied. “I could hardly imagine being able to put this on my address labels. Uh, if I was a mail pony, you know. ‘Big Giant Castle’ might fit!”

Rockhoof chuckled. “Well, if it’s not too presumptive of meself, miss Hoofsy, maybe I could give you a tour of the castle interior? Show you a bit of life inside?”

Derpy swallowed and fought down the nervous sensation in the back of her mind. This was where things got tricky. Being charming and courteous was one layer to the practice, but going into a pony’s abode could lead to the bedroom. The bedroom would lead to close encounters. Close encounters could mean...problems.

Dinky’s hungry expression as she looked past Derpy’s shoulder to their empty cupboard seared in her mind’s eye.

“Sure! It’d be neat to see inside. Lead the way, Mr. Rockhoof sir!” Derpy insisted, earning a smile from the big pony as they went inside.

“And this here be my humble abode.” Rockhoof said as he opened a door with his namesake engraved above it, Derpy following in behind him and closing the door politely after she was inside. Derpy was expecting perhaps a bachelor’s pad of sorts for a stallion like Rockhoof, a place that any regular mare would swoon about being in alone with him. Perhaps a throw rug of a fallen beast or a trophy wall with his many adventures on display as victories and hallmarks of his history.

In all truth, however, it seemed to be more...homely. There was a carpet on the floor, but one you could imagine seeing in any old home. His mythical shovel did rest on a marked spot above a fireplace, still as solid and sharp as if it was just made. Bookshelves sat off to one wall, though as Derpy passed by them, she could see dust on the shelving. He wasn’t much for reading some of these books, she guessed, though some looked worn and well-read. His bed was at least matching for his large frame, capable of hosting at least four ponies Derpy’s size in comparison.

“It’s a cozy place for sure. Much more welcoming than my little house.” She commented. “I’d feel like a little princess living here.”

“You and your little one, hm?” Rockhoof replied, coming to sit beside her as she looked out the window to Ponyville beyond. “Do you think she’d like the castle too?”

“Gosh...Dinky would be running everywhere.” Derpy murmured in thought before she realized her slip-up again. “I-I mean, Dinky as in, uh...m-my daughter’s friend Dinky. She’s really energetic. You know, how kids are!”

“Mmhmm.” Rockhoof hummed as he nodded. “The same for all the wee lads and lassies out there.”

There was a quiet, pregnant pause in the conversation. Derpy felt her nerves light up as she reached mentally for something, anything to keep conversation going. Maybe she should just take the plunge after all and proposition him? He’d been a gentlecolt the whole time. Kind. Attentive. Maybe he would be gentle with her, and -

“Miss Derpy?”

The use of her name made her freeze up, her eyes wide in surprise. She looked to Rockhoof, who was watching her and continued speaking. “That’s your real name. Is it not?”

“It’s…” the brown maned mare tried to hold his gaze but gave in and broke it off to stare out the window again. A defeated sigh left her muzzle as she ducked her head down. “...yep. It’s me. I gave it right away, didn’t I?”

“Well, not many ponies got a daughter named Dinky out there. But I knew before then.”

“...what did I do wrong?”

“Nothing at all, actually.” Rockhoof’s answer made her look up at him. “You have to be aware, Derpy, I am not a pony easily tricked by disguises. It comes with the adventuring and journeys in the past, and even after 1000 years in limbo, these eyes stay sharp as ever. But it’s not the only reason.”

“...please don’t give me a bad report, Mister Rockhoof. Or tell anypony I do this. I-If you can promise me that, I’ll let you enjoy your evening.” Her forehooves trembled on the floor, the shakes carrying up her forelegs while the pit of her stomach turned to ice in the impending feeling of rejection and polite disappointment he’d give her.

She hadn’t expected him to reach out to her and embrace her trembling form against his broad chest, her shaking slowly easing as he continued to hold her. She could only blink in confusion and wiggled a little in his grasp, the magic bracelet on her foreleg slipping off and to the floor with a metal clink. Gone away was the earth pony mare, and in her place being held by Rockhoof was once again the blonde ditzy pegasus the town beyond knew.

“What’re you...I don’t understand?” Derpy said finally.

“Breathe, first. Please, Derpy.” She listened, and did as he instructed. Two deep breaths later had steadied her hooves some, easing her discomfort while privately enjoying being in the secure hold he had on her. He seemed to sense this, and continued speaking. “You haven’t done anything wrong at all. In fact, you’ve done terrific in all this business.”

“I have? Really?”

The disbelief in her voice prompted a rapid nod from the stallion. “If you can believe it, it really wasn’t me who set this up. My friends, as kind as they all are, go out of their way sometimes. They know I’ve been lonely, even among the students and the other ponies here. There is a unique loneliness you can’t fulfill or correct with them. So they suggested I try this out. And so there I was, waiting for you in that restaurant.”

Derpy brought a foreleg up and rested it on Rockhoof’s, a gentle touch he seemed to reciprocate with a light nuzzle atop her head. “When I first saw you and saw the mare beneath the disguise, I had to think to myself: what’s a lady like her doing involved in all this? But I understood it in a way. We all have our needs out there. Mine were just involved in having somepony who wanted to spend time with Ol’ Rockhoof. Yours, well...you love your daughter dearly. You wouldn’t be here otherwise, I imagine.”

The blonde pegasus listened and spoke only once she could find her voice again. “I mean...if it’s all the same to you, Mister Rockhoof, there’s a lot of mares who’d be happy to keep you company. Mares better than me. Ditzy, clumsy Derpy.” She replied.

“Better in shallow terms, perhaps. But you understand me in ways they may not.”

“How so?”

Rockhoof released her from his grip and took a couple steps aside from her, leaving the pegasus to watch as he turned about to meet her stare before his form took on a white glow. It took a few moments, leaving Derpy to cover her eyes to prevent being blinded. When the light had faded, she lowered her hooves and felt her jaw slip in surprise at what she beheld. Gone was the bulky, muscle-ripped stud of a pony from myth and legend. In his stead sat a much smaller, thinner earth pony. The goatee part of his beard had gone away, though his beard remained if trimmed smaller.

“You’re not the only pony who has to wear a disguise to get business done. To be treated differently.” His voice was softer, but still the same foreign accent that Derpy told herself was charming to listen to. “All the world knows, in all the books and movies and myths, is the strong pony with legs like tree trunks and all the might in the world. Few, if any, remember the youth underneath the magic cover. There’s days I tell myself to lower the disguise, to stay me for a day, but I know the world outside thinks otherwise. They’d think a stallion like me does better behind a stall, or kept indoors.”

“Or like a mare who gets told to keep to her route. And to not think so hard or else her eyes will go more cross-eyed?” Derpy watched him nod, and a sense of relief and understanding seemed to wash over her all at once. Her wings extended out and went slack as she lowered her head and smiled. “...do you know you’re the first pony in awhile who I told myself really did think I was pretty? Even if I was in disguise?”

“You still are. Very much so.” she looked up at his bashful look, his cheeks turning a light red. “If ye don’t mind my saying so, that is. I have...thought it often, when I saw you about in town.”

Derpy’s eyebrows rose up. “But I’m...well I’m me! Ditzy Derpy! The Mailmare! The...the walking, flying accident!”

“Sticks and stones, Derpy. Sticks and stones. And I’ve trotted plenty of both underneath me as I helped pony after pony in times of crisis.” Rockhoof said as he walked back over to her and sat before her. “When you smile, when I have seen you with your daughter, I found myself witnessing a mare who found her heart’s calling. Who would do whatever she could to protect that bundle of happiness she’d brought into the world. And she did it with a smile that not even Mistmane, in her prime, could match to me.”

Derpy’s cheeks burned red with heat at the praise and comparison. “...y-you sweet talker.” She mumbled, making Rockhoof chuckle. He reached out to her, and this time, she returned his embrace. They stayed like that for a time, only easing when Derpy pulled back before she blinked in surprise.

“I’m...taller than you? Like this?”

“It would seem so. I never was much high off the ground before my magic came to me.” Rockhoof noted, shrugging a shoulder. “Only means there’s more of you for me to appreciate, from my view. I get to look up, and see a beauty above me.”

Derpy’s tail flicked behind her, and she took a moment to compose herself before bringing a foreleg up, the tip of her forehoof brushing Rockhoof’s bare chest for a slow pass.

“...you know...technically, I’m still your company for the time being.” Luna’s moon had started to rise in the distance beyond the window, but neither of them were looking outside. Rockhoof stayed fixated on watching the blonde pegasus in front of him. “I’m...not the most amazing mare in town. But...maybe we could still turn this into something good? Even with my screw-ups?”

“I’ve yet to see one mistake out of you yet, Derpy. Can scarcely any sane stallion say so either.” Rockhoof assured her. “But...if you’re askin’ what I think you’re askin…”

“I might be.”

“And supposin’ I said yes?”

“Is the door to your room locked?”

“It does it on its own.”

“Is the room soundproof?”

“Magic crystals n’ whatnot do it for us. At least in the bedrooms.”

Derpy smiled and stared into his bright eyes as a similar smile crossed Rockhoof’s lips.

Derpy wasn’t quite sure which one of them really initiated things. There was the hesitancy at first, because both of them did want to go further but were being mindful of the other. Then there was a kiss. It was a short one, a test, but one that made her go positively scarlet when she found him bringing her back in for another. His grasp of her body, even though he was just about her size, had all the strength of a stallion twice his size. It didn’t hurt her though; rather, Derpy felt herself sink into it and they soon had fallen back onto the bed.

A little bit of rolling had Derpy laid on her back, wings fanned out behind her and her head cushioned by a large pillow. She looked down to her chest, her body tingling and shivering as Rockhoof’s head slowly lowered, each inch marked by a gentle kiss given by the dutiful Pillar. It was a sensation made almost erotically torturous as his beard also tickled at her skin, tearing her between giggling and moaning. The latter became more prominent, however, when he got low enough to tend to her teats.

“I-I’m not the biggest mare...I-I hope that doesn’t bother you.” She managed to get out between little gasps as he nuzzled and licked at the sensitive mounds.

“You could be the biggest or the smallest: I’d ravish them all the same.” He told her before giving a playful growl and latching onto one of her teats to playfully suckle at the nipple there. Derpy’s head threw itself back and she squealed in delight, basking in the sensation as Rockhoof’s hooves went to work on massaging her other teat and her thigh closest to his head. His beard continued to tease at her skin with every motion his chin and head would make, but she didn’t dare stop him.

“Do you...do you do this for every mare?” she got out.

“It has been awhile since I last lain with a mare. But that just means I can give you all the attention you’re due and more.” He replied before giving the lightest of nibbles on her nipple, swapping teats to treat its sister and continue what he was doing. The multiple efforts he was enacting on her were doing their job: already she could feel her nethers heating up, her hind legs giving reflexive kicks into thin air while her forelegs felt for his head.

“Nopony’s ever - ah! - d-done it like this. Too quick. Always...fast.”

“And clearly not enough, because you can still talk.”

“W-what do yooOOOO!” Derpy’s train of thought crashed, rolled, and exploded into smithereens as she was treated to the sensation of Rockhoof’s tongue invading her marehood. She didn’t care if he was in his real form, his tongue still felt absolutely massive inside her. It spread her walls as it writhed about, pushing and prodding before penetrating deeper into her tunnel and making her whole body spasm. Her forelegs clamped onto Rockhoof’s head but her hind legs couldn’t follow up. He had been ready for it, and had placed both his hooves on her thighs to keep her spread apart. She was entirely exposed before him, but the idea only turned her on more.

‘Rockhoof is eating me out. Rockhoof the Legend is eating my pussy! Ohsunohmoonohmuffins!’ These thoughts rocketed around Derpy’s mind but none could be vocalized, pleasure keeping the connection from being made as he worked her over. It was like he was hungry at the restaurant all over again, but now she was his main course to drink up. He slurped and licked with a thirst that only Derpy could hear, her face flushed and mouth wide open to let her gasp as she tried to keep up with him.

“R-rockhoof-oh!” another darting shock of pleasure rocked through her as his tongue dove into her depths and hit sensitive tender pussy. Her body trembled and she tried again.

“Rockhoof!” Zap

“R-rock-” Zip

“Rrrr-” SlipandZip

Derpy’s body went on autopilot as she found herself barreling to an orgasm she was ill-prepared for. But Rockhoof wasn’t willing to stop, not for a moment. The panting pegasus could only grab onto his head and squeeze, pushing him harder into her groin as her hips bucked up in a vain effort to get more of him. He rewarded her efforts with a gentle press on her thighs before his tongue circled and stroked the roof of her pussy. It toppled Derpy’s resistance like an avalanche, and she could only manage high pitched gasps for air, rapid and keeping for only a moment before cycling into another breath. Stars exploded in her vision and were still fizzling by the time she came down, her arched back groaning silently in relief as she laid there.

“Now that is a finer drink than the oasis of Saddle Arabia.” Rockhoof said, though it took Derpy a moment to comprehend what a “drink” was and what a “Saddle” was and why it mattered to Arabia. She lifted her head, focusing her vision just enough to see the Pillar rubbing at his beard, his chin shining with her fluids. Her hind legs were finally allowed to move, but they could only manage a hesitant shake as sensation came back to them and the rest of her body.

“Rockhoof...I should...I need to. Get up here.” She mumbled out her wants to him, managing to lift herself up and over to be on her belly. Her marehood was still giving her little echoes of ecstasy that pushed her to act. “You had fun with me, now let me have fun with you.”

Rockhoof seemed hesitant, making Derpy pause as she saw him maintain a position on his belly like hers. “Well...you don’t have to if you don’t want to, lass. Yer not obligated to-” he started to say.

“Nuh-uh. You rocked my world. Now I gotta rock you.” Derpy insisted before giving a playful giggle. “Show me your pillar, Mr. Pillar.”

Rockhoof nodded slowly. “Well, a gentlecolt doesn’t tell his lady no.” And so, the hero of Equestria’s past rose up and turned over, leaving himself entirely exposed to Derpy’s gaze. She sat there and at first thought she had misjudged the coloration of his fur. But she could see his fur behind the throbbing mass that started at his groin and emerged from his sheath to reach almost his entire barrel in length. The musk coming off it swam into her senses as she drew closer, inhaling his musk in and feeling her marehood clench in want for him to fill her with it.

“...” There were no words Derpy could muster to describe Rockhoof’s member. Long, thick enough to surely fill her, and with a hefty pair of balls resting at the base, it was like she’d brought one of the old Playmare pin-ups to life. Only he was very very real, and very very cute, and very very very hard. A testing touch of her hoof to the side let her feel his warmth as it pulsed in her grasp.

“If it is too big, I understand. Of all the things about me that my magic changes, this is the one constant it cannot.” Rockhoof offered her.

“I want it in me.” She murmured out, bringing her other hoof up to stroke along its side like its partner was doing.

“I-I do not wish to hurt you.” He said, giving a huff through his nose as she rubbed his cock. Derpy licked her lips and lowered her muzzle to the blunt end of his length.

“This is worth being hurt by.” She whispered before kissing the tip. Her stroking continued as she tried to make out with the thick cock, quickly finding the flavor of him to be an earthy, but delectable taste on her tongue. She had to stretch her jaw a little to fit him into her mouth, yet the groan he gave was worth the effort. Her blonde mane swayed about her head as she bobbed around the swollen tip, lavishing it with long strokes of her tongue. Rockhoof throbbed in her grasp, but did his best to keep still for her.

Derpy hadn’t expected him to be so gifted, easily shooting past any of the past stallions she’d taken to bed before. There was a tiny tremor in her confidence of just how well she’d handle him, but the nervousness only seemed to heighten her excitement. It was palpable enough to make her pull off his cock, licking her lips while keeping his cock aloft with her hooves.

“I’m sorry I can’t quite. Um. Do a blowjob.” Derpy said. “You’re just so...does it hurt?”

“Nay. The only pain I’d have is if we stopped here and now. Your hooves are as soft as silk, lass.” He assured her. “But like I told you before. You don’t have to do anythin’ you don’t want to.”

“Well, if I can’t get it to fit in one hole...I’ll just have to try another, won’t I?” Derpy’s eyes held his stare as she used her wings to lift herself up just a little, floating with practiced light flaps that brought her to hover in the air above him while using a forehoof to aim his cock at her wanting marehood.

“Go slow. I would never want harm to come upon you, Derpy.” He insisted.

“I’ll try. There’s just so…” she trailed off as she let herself sink down, his blunt tip pushing against her folds before they accepted him. She tossed her head back and gave an eager giggle. “...so much!”

“Easy, easy!”

“It’s ok, I got this. I-whoop!” Derpy’s wings twitched and ceased trying to fly for a moment. It was enough of a moment, at just the right crucial moment of flight in such a spot, that it brought her down onto Rockhoof’s cock at a pace neither was quite ready for. Rockhoof held firm, catching her hips despite having several inches now sunk into her depths. Derpy, however, had an almost vacant look of shock on her face.

Now, Derpy knew a few things in life. She was actually quite good at math. You had to be to work in the mail business, for packaging and costs and whatnot. A rough guess by her eyes had wagered Rockhoof would fill her up with little effort, but the miscalculation was as evident as the pleasure shooting through her body as she clenched around his member. She was only halfway down him, and already he filled her up so much that she couldn’t fathom getting off. And if going up wasn’t an option, then it only left going down.

With a deep breath, Derpy unclenched and rested her forehooves on Rockhoof’s, getting him to ease his grip off her flanks and let her sink a couple inches further. She gasped out and he held onto her again. He wasn’t letting her go further, but she had to. She needed to.

“L-let me...let me. Please.” She let out, and he relented after a moment’s wait. Derpy’s rump wiggled as she continued to work herself down his length, and when she finally did stop, it was only with the certainty she’d sheathed him entirely. The pegasus gave another clench around his cock, and felt him shudder in his hooves on her flanks and in her own depths as he pulsed. She loved it; every time his heartbeat echoed through the literal pillar of cockmeat, she got to enjoy a shiver of pleasure as he shook her very core.

“Faith and Begorra.” she heard him swear, prompting her to open one eye she’d closed to peer down at him. “How can ye fit it all?”

“I’m a mom. Fitting beasts like this just...comes with the job-ohgoddess.”

“Does it hurt?”

“No. Not pain hurt. It’s a fun hurt.”

“Fun hurt?”

She grinned down at him. “I can feel every inch of you. It’s so...warm. So good.” She tried to wiggle, and the result sent a bolt up her spine before she sighed in delight. They sat like that for a moment before Derpy spoke again.

“You...you might have to help me move.”

“Are you ok?”

“I’m almost in heaven. But my legs are...a little stuck. Can you help?”

It took Rockhoof a moment to solve the dilemma caused by his dick, but Derpy was more than happy to let him control the pace. In that moment, she did really mean that moving was difficult. The jolts of pleasure coursing through her was scrambling every signal in her mind to try and move on her own. If that wasn’t the case, she’d be doing all she could to feel more of Rockhoof’s shaft. A firm grasp of her hips was his signal before he lifted her up, Derpy’s light weight a helpful boon to the Pillar of Strength. He only got her up to the middle of his cock, his medial ring stretching her open just a little more before he brought her back down, evoking an ecstatic cry from the pegasus.

“Yeah! Just...just like that!” She gasped out, eyes wide from the rough but pleasurable stroke. The stallion beneath her grunted as he lifted her again, the extraction of his cock from her depths evoking a moan from her and a desperate whine from her to shove it back in, which he fulfilled once he brought her back down. The pacing was slow, but with powerful enough force that Derpy could feel her breath get knocked out each time. He was the biggest she’d taken yet, and he was making it more memorable than any other as well.

“Tighter than a python, ya are, lass!” Rockhoof let out as he continued to work her pussy up and down his cock. “How do you do it?”

Derpy was sure the answer was something between pegasus biology, at-home exercises, and his own impressive gift, but could only manage a jumble of sounds as her wings flapped to try and get her body to move faster as she rode him. She needed more, she had to get more of him! Rockhoof found his rhythm with her wings movements, and it allowed for a longer stride in his thrusts up into her depths while allowing the pegasus to throw her head back. Her juices kept them both plenty lubricated, the squelching sound of her marehood trying to keep him inside filling the room between their grunts and moans.

The idea of even trying to figure out how close she was to a climax didn’t click in Derpy’s mind, only to keep the process ongoing as long as possible. She’d throw herself down on his length, the repetitive thrust of his lengthy member making her nearly yell were it not for being out of breath each time. Occasionally, she’d roll her hips or clench tighter on him, a heightened sense of pleasure crossing her mind and taking delight in hearing Rockhoof moan in response. His throbbing dick was swelling within her, getting close to his own climax. Too soon in her lust-addled opinion, but she wasn’t going to deny him his pleasure.

“Derpy!” He warned overtop the fevered sound of her rump slapping down onto his thighs. “Can’t...hold off!”

“Inside! Inside! Cum inside, please!” She begged, and he relented with a strangled bellow and a final pull down that hilted himself within her. Derpy’s wings froze in a stretched out state as his cum burst into her depths, flooding her with thick, heavy strands of cum. For just a moment, she thought she could actually see straight before the world turned into a dizzying flash of color, ecstasy overwhelming her senses as Rockhoof continued to flood her pussy. She could feel it pouring out around her stretched marehood, thick wads of seed splashing out onto their groins. It seemed unending, leading Derpy to press a hoof to her belly to feel it seem to swell a little from the sheer volume he was giving her.

“Oooh...oof…” Derpy groaned out before managing to work out an idea of extracting him. Laying herself overtop his chest and pushing the idea of just collapsing there aside, she worked her hips up and off each inch she could manage of his length. With a wet sounding pop, he did finally come out of her, leaving the still dripping length to flop against her rump. It was still big enough that the new positioning let the excess drip off his cock-end to fall on her lower back, dousing the base of her tail and fur with his essence. It didn’t bother her in the slightest.

“...I can hardly believe you took the entire thing.” Rockhoof murmured beneath her. Derpy wiped at her brow with a hoof and managed a grin at the stallion she could only hope looked sexy in her sweaty, weary state. “The few mares who I recall bedding considered it too monstrous.”

“Mom powers, activate.” She mumbled out before snorting. “Can fit...anything anywhere.” She felt him give a throb as another light drizzle of cum dripped onto her rump. “You’re worth the ride.”

“Y-yes, well...you were...very fantastic as well.” Derpy looked to his expression, and searched his eyes. He wasn’t dissatisfied; she knew that expression aplenty. But his wording suggested he wanted more from her.

“Think you got another round in the chamber, big guy?” She questioned, bringing a hoof up to rub at his firm chest. He was still very much an earth pony, bound in limber muscle and little fat, even if he was in what he considered to be a less magnificent state.

“I could very much go again. Especially with a beauty like this atop me. But...are you sure you do not need rest?” He asked. “To injure you would be my greatest regret.”

Derpy smiled at the concern, and worked to lift herself up off the stallion. It was a slow action, partially due to wobbling limbs and a growing attraction to just snuggling the warm stallion. But the temptation to really cut loose was too inviting to ignore. She turned about, letting her tail lift to the side and looking over her shoulder to the watching stallion and his cock.

“This rump right here?” She reached back and gave her butt cheek a light tap, “It’s broken whole buildings before. She can...I, can take you again. If you’d have me.”

Rockhoof clambered up and brought himself closer to her, adopting what Derpy knew to be the traditional way of mounting a mare. He was surprisingly gentle, even with his length already rubbing against her underside in a slow grind of desire.

“Tis a rump I’d plunder endlessly, for sure.” He remarked, and for a moment, Derpy felt her face burn at the idea of not just the lighter, smaller Rockhoof doing it to her, but the behemoth of a stallion turning her into his sexual plaything. Her winking lips urged out another dollop of the cum he’d already filled her with, and she was left to shudder as he nipped at her neck playfully.

“I want all of it. All of you.” She told him, earning a tender kiss from Rockhoof as they held there before he pulled back.

“Then you’ll get it all, my fair lady.”

The statement seemed to also be his start signal, as his grip on her tightened while he thrust his tip into her depths. She must’ve still been stretched enough to let him in with little work, something she was grateful for as her marehood was filled to the limit once again. The excess cum within her depths was sloshed around, her seed-filled womb welcoming his cock with a clenched grasp that made him growl playfully down at her. Even with all that between them, she could still make out the heat of his tool inside her pussy, and allowed a pleased sigh to escape her.

It was the approximate one second of pause she was allowed before he snorted and pulled back hard, making her gasp before he shoved himself back in just as roughly. Unlike the controlled pace before that let her acclimate, he was mating her with all the due intent of claiming her as his. They didn’t need to worry about hurting each other now, and all that was left was the bare and loving lust they were indulging in. Derpy moaned into the sheets beneath her muzzle, her front legs lowering as she kept her hind end lifted for him.

He took it in stride, his thrusts retaining the power they had as he quickened his pace. The bed was rocking now, the frame of it shaking in rhythm with Rockhoof’s motions. Derpy wasn’t sure how much noise could be made from the crystal room’s design, but by Celestia, it was like Rockhoof wanted to test the limits. The stallion was panting, sweating like she no doubt was as he claimed her from behind. He had been holding her around the middle at first, but now was on his hind legs and holding onto her grey rump for support. Her tail whipped and slapped against his forelegs at random, the only form of communication she could muster while her mouth was muffled by the bed.

Rockhoof’s cock was like a battering ram to her womb, but the pleasure of his efforts overwhelmed any sort of discomfort that could’ve been felt. More personally, Derpy felt like she was actually being claimed by the stallion, as if they’d gone back to his time and the mighty warrior had taken his prize in a lustful passion with her. He’d take her all to his liking, and she welcomed everything he had to give. The pegasus found the right timing to start bouncing her rump back into him, provoking an approving groan from the earth stallion plundering her pussy.

“Faster! Please! I can take it!” She cried out to him. He obeyed without hesitation, and Derpy’s ability to speak melted before the rough and fast thrusts he gave her. The whole room seemed to be shaking, but that had to be just herself she reasoned.

Time faded from Derpy’s awareness as well, letting herself be overcome with a climax that slammed into her from out of nowhere and making her cling to the stallion’s cock in her marehood all the more. If it hindered Rockhoof at all, it didn’t show as he only gave a light slap to Derpy’s rump before resuming his pace. The slapping sound of his groin meeting her rump, as well as the occasional bump of his hefty balls against her underside became the tune in the pegasus’ mind. Again and again, in and out, in and out, he took her as his own. She loved it.

Who cares if she couldn’t walk for the next week? This one night was making up for months of stress and woe.

It was a truth that echoed through her being as Rockhoof leaned down and nipped at her neck, a silent but clear assertion of dominance she gladly submitted to. Gone was the worries of being undesirable, banished were the self-doubt and questions of worthiness. They all crumbled before Rockhoof, and she welcomed him wholeheartedly into her world. Her lust-laden mind even imagined scenarios playing out between her and Rockhoof: coming to pick up her daughter from a class with him, only to have him take her in the nearby closet. Bringing him a mailed package of chocolates for Hearts and Hooves Day, and watching as he ate a freshly melted chocolate piece right out of her marehood while she lavished his massive member with attention.

The imaginative thoughts popped out of her mind as the roughened pace Rockhoof had taken with her brought her back. He was flaring, she realized, and she closed her eyes to focus on the sensation as he gave a final bellow of release as his floodgates opened again. Once more, her womb was flooded with the earth stallion’s potent seed, the deluge now finding it even more difficult to escape her depths with him plugging her up so well. Her belly swelled, containing the cum within her from his explosive finish and immersing her in the warm sensation of bearing so much life essence.

Only when Rockhoof finally pulled back and slowly – even arguably regretfully – withdrew his cock from her plundered marehood did a flood of his cum escape her. The hefty goop strands fell out at their own accord, staining her marehood and the grey fur surrounding it white while he collapsed alongside her. She could only coo, a hoof resting on her swollen barrel before being joined by Rockhoof’s own as he cuddled up behind her. The tender nuzzle he gave her eased the pegasus as they laid there, and before she could think on it, she was in the world of dreams while buried in the warmth of the mighty stallion lover she’d come to treasure.

When morning had come, and the pair rose from the bed to finally comprehend the previous evening, Derpy wasn’t expectant of much. After all, in the run of things, she was still one of the ponies in the business who was set to a lower pricing. She didn’t see herself as such a catch like some of the other mares who partook in the escort work like she did. Which was why the mare found herself quite surprised to see Rockhoof giving her a sack of bits worth four times over her regular rate.

“U-um. Whoa.” Derpy found her voice as she looked up to the stallion. He’d adopted his larger form again, no doubt having a busy day ahead of him. He had taken the time, however, to treat the pair of them to a warm and gentle bath. She was very grateful for it, given how sore she was, and moreso for the tender way he looked after her with nary a demand of his own. “You know I’m...one of the cheap mares. Right?”

“Tis as big a lie as Ursa Major, Miss Derpy.” He replied, shaking his head. “In this stallion’s eyes, you deserve this and more.”

She tilted her head. “It’s not...you know. Pity money, is it?” She questioned. She had to; this was more than three month’s wages at the mail office, let alone her escort work.

“The only pity I have is on myself for not seeing you home today. Besides, I have little use for these bits everypony insists upon. There are more valuable things out there. And ponies.” He pointed out. Derpy smiled and sat the bundle of bits in her saddlebag for taking home. “I um. If I may?”

“Hm?”

Rockhoof looked bashful as he turned his eyes aside to look to the wall, making Derpy watch him while he seemed to work out his words. “If...perhaps some time...Miss Hoofsy or Derpy would be keen on sharing her company with an old legend, she would be welcome to stop by?”

Derpy stared in genuine surprise at the offer. “...really? Me? With you?”

“I know I am hardly the worthiest of stallions to know you or be with you. But...in you, I feel a kindred spirit. One who can take comfort in having somepony who sees through the layers of the world to the truth in all of us. The truth of being a hardworking mare looking after her young one. Or the truth of a stallion feeling actually safe to be himself, and not his legend for once.” He explained.

The blonde pegasus was left blushing at the extended offer, but smiled by the end and nodded slowly. Using her wings to lift herself up, she brought herself to his eye level and kissed his cheek gently before pulling back.

“It’s a date, mister Rockhoof.” She told him. “Now...I better go on ahead. There’s more packages to handle out there, even after the magnificent one last night.”

Rockhoof chuckled. “And I’ll explain to the rest of the castle how last night was merely an earthquake.”

Derpy glanced up and down the hallway where they stood, taking notice of several skewed paintings and pictures and even some fallen decorations here and there. She did her best not to laugh like he had, but a snicker was inescapable.

“That’s a good idea, I think.”

Author's Note

I was inspired to do this. I hope you all enjoy it a little, just something positive for Derpy!

If you're feeling charitable, feel free to add something to my Ko-fi!