Derpy Shows the Doctor How

by Clopficsinthecomments

Rating: mature
Tags: Derpy Hooves, Sex, My Little Pony: Friendship is Magic, Doctor Whooves, Romance
Length: 4555

Derpy and The Doctor go on a first date - things get steamy!

Based on a pic by ZippySqrl at derpibooru

Derpy and the Doctor go on a date which goes swimmingly, and Derpy take the Doctor down to his lab to ravish him.

Because this is a new experience for Doc in his current body, Derpy needs to help him out a little bit, but its all in good fun.

Published 2017-07-03 19:10:06 UTC
Last updated 2017-07-03 19:10:06 UTC

First Date

Derpy’s ears perked up upon hearing the *rap rap rap* at her front door that she had so nervously been waiting for.

She hopped off the couch quickly, rushing over to the hallway mirror to check her mane and tail. She licked her forehoof and smoothed down a wilder part of her hair, only for it to spring back into its original position immediately. “Perfect!” Derpy chirped with an upbeat flick of her tail - nothing was going to dampen her spirits today.

As Derpy rushed toward the door, she suddenly remembered her most precious muffin and she banked hard back toward the living room, bumping over the coat rack as she did so and tumbling hard into the center of the room. She slid nose first across the carpet, a jumble of wings and limbs right up to where her daughter Dinky had been idly building a house of cards. Derpy’s nose stopped millimetres from the cards, and for a moment all seemed to be well… before she let loose with a titanic sneeze.

“I- I just don’t know what went wro-”

Derpy was interrupted by Dinky placing a hoof over her mother’s muzzle as she gestured to the house of cards, still completely intact. Having long since become a veteran of living with her mother, Dinky had been gluing the playing cards together as she assembled her tower.

Derpy squeaked happily and planted a kiss on her precious daughter’s head. “That’s my clever little muffin! Now, Rarity and Sweetie Belle should be over shortly, and I’ve left some dinner in the fri-”

Dinky once again silenced her mother with a single hoof before looking up at her with a smile. “Stop worrying Mom, I’ve been on my own hundreds of times… you’re just nervous about the big date. Which you shouldn’t be, the Doc’s a great stallion and he’s been goo-goo over you for months now.” Derpy blushed and pawed at the carpet.

Dinky saw an opportunity to tease her beloved mother and adopted a mischievous grin. “And make sure you don’t come back early Mom... you and the Doc should really drain all that pent up energy with a good, hard, buck.”

Derpy’s wings flared out a little as she turned beet red. “M-muffin! Y-yes if things went well, I was going to… I mean hoping to… er w-well… Wait! Where did you learn about that sort of thing anyway, Dinky!?”

Dinky scoffed and tilted her head up in pride and smugness. “I’m not a little foal anymore mom - well… not so little anymore anyway. Hurry up or you’re going to keep your stud-horse waiting!”

Derpy frowned as she looked down at her precious treasure, she knew it was all a part of growing up, but she’d still need to have a talk with her later. Derpy had run into some trouble herself in that part of her life because she’d been thrust into adulthood faster than she’d been ready for… though she didn’t regret her reward one single bit.

Derpy bent down to snuggle Dinky one last time and smiled determinedly, “Well, I’ll try my best. But you and I are going to have a little talk later, Muffin. Have a fun night!” Derpy called over her shoulder as she trotted to the front door.

“Go get him Mom!” Dinky waved as her Mom opened the door.

“Mademoiselle!” Doctor Whooves bowed, full bouquet of daisies in hoof, as the door opened. “It is my privilege to take thy hoof on a soiree with the best and noblest of intentions, at the permission of thy sire or the matron of thine esteemed household.”

Derpy’s mouth hung open and her eyebrow arched as she looked at the prostrate pony in front of her with confusion, “Uhhh, Doc? What are you doing?”

“Why, exactly what the Ye Olde Equstrian Wedding and Bedding Tome described… why? Is it because I couldn’t find a four wheeled chariot? I knew it, the evening is ruined! If only there we-” Doctor Whooves was interrupted by Derpy leaning forward and planting a deep kiss onto the doctor, letting her tongue slip into his open mouth and play clumsily in his for a moment before she withdrew.

The Doctor was frozen in shock before Derpy explained with a bright smile on her face, ”Doc, I’m no expert on dating rituals either so let’s just get all that tension out of the way now and have a good time tonight, OK?”

“Yeah!!! Go Mom!” Dinky pumped her hoof in the air as she watched from the hallway, cheering her mother’s forward move at the Doctor.

Derpy moved forward, pulling the Doctor who was still stuck in his stupor with her forehoof. ”C’mon Doc, or we’ll be late for our reservation. See you later Muffin!” Derpy called over her shoulder to her waving foal.

========================================================================

It had been a fantastic date, with plenty of amusing and impossible stories from the Doctor, and the food had been fantastic. Derpy had managed to put her hoof in her mouth a few times rambling on about her daughter or the latest Equestrian mail delivery system, but the Doc always stared deeply into Derpy’s eyes as she rambled on, infatuated with her passion and cheerfulness.

After a late night sundae, the pair had walked back toward the Doctor’s lab, where he paused at the entrance before looking to Derpy.

“Err, well my dear. ‘Twas a positively delightful evening, and I would love to do it again soon, or even do it again now, or if I could… do it again earlier - like yesterday? In any case, mademoiselle I bid you a great evening.” he bowed and looked up at Derpy with a nervous smile.

Derpy looked down at him with a bit of a skeptical and disappointed glance, like a mother would give to a foal who has been caught in a rather telling lie. ”Really Doc? I thought we were past this - you don’t need to go through the whole first date etiquette with me.”

Derpy put a hoof under the Doc’s chin and lifted him up so they were both standing on their hind limbs, enveloping each other in a bipedal hug (Derpy knew the Doc preferred those) before she leaned in and planted another deep kiss on him.

This time the Doctor was more involved, using his powerful tongue to tackle hers and press back into Derpy’s mouth, exploring and twisting with hers as he clutched her tightly to his body in a leaning-over, movie-poster style kiss.

“Phew! Did I ever need that. I was hoping so much that you’d see through that polite veneer of mine. But how did you know anyhow?”

Derpy chuckled and grinned with a flushed face as she responded, moving one of her hooves down the doctor’s chest and pawing a very fleshy, sensitive area before responding. ”Well you may have been buttoned up this evening, but little Doc here has been peeking in and out all evening and letting out quite the musk.”

As she spoke, leaning in to the Doc’s face, Derpy’s hoof rubbed the fleshy tube sultrily. The Doctor, once again a bit shocked by the circumstances, was paralyzed in all but one organ as his penis extended out of the shaft, flopping onto Derpy’s rubbing hoof like a limp salami.

Derpy leaned in and planted another kiss on the Doc as she continued rubbing his junk, tracing carefully down to his testicles. The Doctor stifled a groan as Derpy coaxed the shaft until it uncoiled to the extension of medial ring and began filling with blood. With each throb of his powerful stallion heart, his cock pumped larger and hotter, and in a few moments it throbbed out to its full engorged extension. The 11 inch long, thick and veiny black tube with a prominent medial ridge and a fatter cockhead was trapped between his and Derpy’s chests. It easily came up to Derpy’s breastbone and she gave it a quick love peck. “Why hello there, not so little Doc.”

Derpy unlatched her arms from the Doc and dropped back down to all fours, and the Doctor did the same. As he landed his erect penis bounced down and nearly hit the ground making him grunt audibly. Ponies were passing on the other side of the street and all pretense of not displaying a massive erection was lost as the flower shop trio tittered and gestured at the Doc, while Lotus and Aloe smiled sultrily at his blushing state.

“Jeez Doc, keep it in your pants or you’ll have the Mop Head and Bucket List,” (the town janitors) “working overtime following mares around on clean-up duty.”

The Doctor coughed in a flustered way as he tried to re-adjust himself. “Pants! Yes, those WOULD be handy right about now, unfortunately this dimension seems a bit prejudiced against their use.”

Derpy gave the Doc a hip check and nipped his ear playfully, ”Come on Doc, let’s get you inside you stud-muffin you.”

“Allons-y!”

========================================================================

Derpy stumbled walking into the Doctor’s lab, careening off of two different experiments and bowling into the flummoxed doctor, tackle-hugging him until she was straddling him in the center of the lab.

“Doc, I don’t know if I’ve said this before, but... I love you.” Derpy nuzzled the brown earth stallion. Blushing, the Doctor responded immediately.

“Derpy, my truest and bestest pony friend, I love you too.”

Derpy pulled back to look at the doctor and squee’d, clopping her hooves together. She began to lean in, and the Doctor braced himself for another kiss. At the last moment, Derpy broke off, and bent lower sliding her muzzle down the Doctor’s neck and chest, through his chest floof and down to his belly, and the tip of of erect cock.

“Doc, I think its this guy’s turn, he’s been waiting very patiently.”

“Great, wickering, stalliooooOoonnnnsssss...” the Doctor moaned as Derpy assaulted his member.

Her big tongue sloppily coiled under the head ridge of his cock, making the Doctor glad he had scrubbed every nook and cranny before going on this date. Wrapping her tongue partly around the shaft like a wet pink rag, she slid down the shaft, and over the prominent medial ring. He groaned as she did so, precum and other juices now freely running out of his tip and oozing down his stallionhood, preparing his length for later activities. Derpy continued down his organ her tongue no longer able to even come close to wrapping around him as he became thicker at the base of his shaft. She went down further and kissed his heavy hanging testicles sloppily before suddenly popping back to the top of his flagpole and trying to engulf his cockhead.

Immediately the Doctor winced as his sensitive organ bumped into Derpy’s teeth. The head had fattened quite a bit and was proving difficult to slip into her muzzle. A second attempt nearly drew an audible yelp from the doctor, so he quickly grabbed Derpy by her shoulders and pulled her up to eye level.

“My turn, my dear.”

The doctor spun her about so she was facing away from him on all fours. With her tail raised high into the air her plump, dark grey marehood was exposed for him to see. Derpy was an athletic mare, from all her time spent delivering mail at breakneck speeds throughout the day, but her predilection for sweets did leave her with a bit of a bubble butt. The mix was the best kind of rump - medium sized and well toned. The Doctor took a moment to appreciate this fact before plunging his muzzle into those beautiful asscheeks and sticking his nose right into the zone between her delectable tight ponut and the entrance to her marehood. This gave his tongue and lower jaw the perfect positioning to take Derpy’s winking and throbbing clit into his mouth.

“Oh Doc, DooOoooc… c-careful I’m… *squeak* unf...”

Derpy moaned and squeaked as her marehood coiled and convulsed with the Doctor’s tongue lashing. On a particularly strong wink, the Doctor clamped his tongue around Derpy’s rather large love button and began to suck as hard as he could.

“DoooOooooctorrrrr, something’s c-coming, coming, CuMmiinnnnnnggg~~**!!!”

Derpy’s moans went incoherent and her wings convulsed as she began to orgasm from the Doctor’s tongue lashing. The doctor felt the clitoral and vaginal throbs become completely spasmic and tighten around his tongue, as if trying to milk it like a cock. Derpy’s squeaks became more insistent as she began spraying lube-like mare juices from her vagina. The Doctor had to shut his eyes as she gushed onto his face and chest, soaking him bodily. As the convulsions began to subside, and Derpy’s marehood unclenched from his face she let out a big sigh and slumped bodily to the floor, nearly sitting on him.

“Wow Doc, *huff huff* I didn’t know you had such a skilled tongue… *huff huff*...” Derpy breathed heavily as she looked back at the Doctor with a goofy grin on her face. She was now laying with her belly flat on the ground and her legs splayed out in all directions as the Doctor stood behind her with a smile on his face.

“Elementary, my dear… I am known throughout time and space as the most cunning of linguists, able to deal out the most vicious of tongue lashings if need be.”

Derpy rolled her eyes with a smile and slid her hind legs further apart while lifting up her tail, revealing her sopping marehood, still drooling liquid out onto the floor. She bit her lip as she looked into the Doc’s eyes.

“Alright then my stud-muffin, why don’t we see if little doc is as skilled as you.”

The doctor hesitated somewhat, and then walked overtop of Derpy, his stallionhood throbbing and still drooling copious amounts of juice. He awkwardly lowered himself onto Derpy, ending up resting his heavy balls and shaft right along her back.

“Errr, just a moment my dear…”

“You’ll need to slide back a bit there, you big goof…” Derpy chuckled as she felt her stud’s heavy ballsack resting in front of her tail.

“Ah, of course, of course...”

The doctor stepped back carefully, dragging his cock back along Derpy’s back, leaving a slimy trail from the head. He reached down awkwardly with a hoof and tried to push his shaft under Derpy’s body as it slapped up against his own chest with excitement.

Watching with bemusement, as the Doctor fumbled with his equipment, Derpy assisted him by carefully rolling up on her side and lifting her left hind leg to let him slip his throbbing shaft under her body. Derpy felt him slapping the hot thick meat against her belly and her breasts as he continued to struggle.

“Hmm, no.. no- that’s not right… perhaps…”

With another chuckle, Derpy scooted forward a bit and twisted her hips up to open herself a bit more. Now the cock head was bouncing about in the right area at least, two slippery organs sliding around on one another. Derpy moaned out a few times when her clit winking would open her marehood more and the Doctor’s cockhead would tantalizingly align with the opening before bouncing away. He was a bit too large to slide in, and Derpy knew he’d need to align himself and hold position with a good thrust to get in even if she was this wet.

“Almost, right… no left… down? No up a bit, a bit more… there we go!”

Derpy’s amusement turned to concern very quickly as she felt the heat of the Doctor’s penis at an entirely different orifice.

“Doc!? D-d-d-doc wait wait wait, not there -”

The cockhead smushed up against her tight ponut, and Derpy squeaked in pain, pulling away and twisting quickly, causing the Doctor’s stallionhood to mercifully slide up and into her dock. As she pulled away and spun to look at the Doctor.

“Not there?”

“W-well, not tonight at least… I need to prepare and do a little spring cleaning before we do that.” Derpy said with a blush and an accusatory glance at her stud.

“Oh? OH! My apologies my dear… it seems my targeting was a bit off... too far North it would seem… confound this po-”

The Doctor was interrupted in his little rant by a kindly hoof to his muzzle. “Doc, can you tell me something? Its nothing to be embarrassed about either… is this… is this your first time with a mare?”

The Doctor scratched behind his head as he blushed even more heavily. “Well technically… with a mare…” Derpy looked at him with an arched eyebrow, as she wondered at the implication, “NO! No, not what I meant. I’ve not been with any stallions. I meant that this is the first time… in this body… with a mare…” the Doctor threw up his hooves, knowing how difficult it would be to fully explain himself in this moment, and gave a sigh of resignation. “...yes.”

Derpy wrapped the Doctor up in a giant hug immediately, as she nuzzled him. “Doc, that is the sweetest, most romantic gift you could give me. I can’t believe such as sexy-stallion like you hasn’t been snapped up. I’m a lucky mare.” Derpy planted a kiss on his nose as she reached down and rubbed his fat cock. She looked at him hungrily and spoke with a sultry tone “Especially when you’re packing big equipment like ‘little doc’ here… want to know a little secret?”

The Doctor nodded as Derpy continued massaging his throbbing, drooling cock. “Doc... you’re my first too.”

The Doctor scrunched his face and looked in confusion at Derpy, knowing the physical impossibility of that statement because of the little foal he’d grown to love so much. Before he could say anything, Derpy placed a hoof over his muzzle to silence him.

“That time didn’t count.” Derpy said sadly, “I was drugged… not even awake and I don’t remember a thing… I decided it didn’t count.”

The Doctor spoke softly, “Derpy, I’m so sorr-”

Derpy cut him off again, “Don’t be! I got my most precious little muffin-treasure from it… and now I’ve got you.”

Derpy reached in and gave the Doctor another deep kiss, as she continued to stroke the full length of his stallionhood under his body. Breaking the kiss off with a contented and happy look on her face she trotted a few paces away from him and planted her four hooves firmly into the floor. Looking under her legs to see the Doctor she smiled brightly.

“Alright, my stud-muffin… since your targeting needs some practice and we BOTH want to get to the good stuff, how about I increase your hit zone a bit?”

Derpy reached back with her wings, digging the partially prehensile feathers into her soft rump and grasping her asscheeks, before flexing her wing joints to spread her wings. The effect was immediate and pulled her asscheeks apart, pulling her still wet marehood wide open, revealing her plump, pink, pony pussy and her swollen clit and sopping urethral folds.

DERPIBOORU PIC OCCURS HERE NSFW - #1476133

Derpy’s bright friendly smile turned into more of a grin. “Now get over here and rut me you stud-muffin.”

The Doctor wasted no time and crossed the room in a bound. With Derpy now on all fours and spread so wide, evolution took over and the Doctor found his hooves sliding into their natural position on Derpy’s shoulders. Also natural was how easily his fat, swollen cockhead, eager for mare-pussy for the past 20 minutes, slid right into Derpy’s willing folds. Unable to prevent the millenia of evolution ingrained into the very wiring of his Stallion body, the Doctor thrust forward immediately and buried himself halfway deep into the grey mailmare’s snatch.

Derpy had an amazing view of the Doctor’s heavy hanging black balls slapping up against her body on the first thrust as they were coated with the built up juices pouring from her aching marehood. The thick and throbbing cockhead slid into her tight love tunnel and she felt an awkward soreness as he inner walls stretched to accommodate this male intrusion into the most deep part of her body.

Her head snapped up in a moan, bumping against the Doctor’s own snout as she moaned.

“Ohhhh Doc, y-you’re so BIG.”

He was indeed, fairly big for the little pegasus. As a well endowed earth-pony stallion, he was probably a bit too much for the more lithe and aerodynamic pegasi race… particularly one a tad on the small size like Derpy, with limited sexual experience.

Derpy’s marehood refused to concede defeat, however. With each bumping thrust… as the Doctor drove his fat cockhead against Derpy’s cervix her vagina lengthened and shifted to support his length and girth.

6 inches, 7 inches… Derpy’s eyes rolled out of her head as she felt her insides coiling and shifting around the Doc’s fat cock… her clit winking heavily as it tried to swallow more of the hot black shaft. 8 inches… 8 and a half inches… Derpy’s mouth hung open and her tongue lolled out of her in pleasure. Yes, it was uncomfortable, but a strange and pleasant uncomfortable as she felt her deepest self being filled with stallion. 9 inches… his balls were slapping up against her with each thrust, sometimes kicking off mini orgasms as they connected with her lovebud.

9 and a half inches, and he began to withdraw the shaft, pulling back out of her with loud squelching sounds and splatters of their combined sexual juices hitting the floor. Her body felt empty as he withdrew, she felt her inner walls coiling and grasping at the cock head, desperate to keep him in her. She tried to thrust her hips back at his, but was hampered by all of his weight resting on her hipbones, but still she tried hungry for the return of his dick. All at once, the Doctor reversed his removal just before fully exiting and thrust all the way back into Derpy roughly as he bit into the base of her neck.

10 and a half inches slammed into her and she was launched into the throes of an orgasm like she’d never had before. “Ohhhh DoooOoOooc….” The Doctor groaned as he felt the coiling and throbbing marehood begin to try to milk his entire shaft and head, suckling he organ to try to get it to spew into her. Derpy’s wings flipped right open as she began shuddering and starting to stumble forward. The Doctor pulled back halfway, unable to pull back any more because of Derpy’s contractions before slamming all the way back in. She screamed out as her vagina gushed out a blast of liquid, blasting the Doctors testicles and hindlegs.

On the next powerful thrust, Derpy stumbled forward and into a table. Placing her forelimbs on it as if trying to escape from the overwhelming hormonal flood she was experiencing freed the Doctor up to shift more weight onto her upper body, pushing her head into the table as she dizzily looked to the side, her brain awash in dopamine and mindless to the pleasure of her body being fucked senseless.

The Doctor pounded Derpy into the lab table, as he was also now a slave to instinct. Derpy’s rear end barely cushioned his savage thrusts, but even she was thrusting back at him. On a particularly hard thrust, the table screeched against the floor before sliding into the wall. The sudden shock/stop of hitting the wall and forced him and Derpy even closer together and he hilted in her at a full 11 inches. His cockhead was mashed up against Derpy’s cervical opening once again, which had now shifted as deep as possible into her body. This triggered an almost epileptic response in Derpy’s marehood, all muscles firing randomly and releasing contracting randomly, causing a swirling, dripping, cumming mess to engulf the Doctor’s completely embedded shaft.

Derpy thought that she had been seeing fireworks before, but now her mind exploded. For a moment she had trouble catching her breath as she simply let out a deep and guttural moan of pain, pleasure, hope, despair and joy that local ponyville residents could hear from blocks away. Awash in this sea of ecstasy, Derpy’s marehood came to its senses and locked down completely, Derpy’s tail wrapped around the Doctor’s flank, doing everything it could to pull him in and keep him in.

The Doctor moaned, “Derpy, I’m going… I’m gonna...”

“Inside! Inside Doc!”

The torrent began with a blast. Derpy *squee’d* louder than she ever had before and shut her eyes tightly as she felt the Doc’s already fat cockhead flare to nearly twice its size inside her, embedding itself up against her uterus in a way that felt permanent.

Jetting directly into Derpy’s cervical orifice it began to fill her. Thick, heavy jets quickly painting Derpy’s uterus, then filling it entirely. Jet after jet packed the full void as Derpy felt the heat inside her building and building, while her own lust was being sated like a cool drink on a hot day. She began to feel almost uncomfortably bloated as the Doctor continued moaning and spurting into her, now into his 10th heavy jet. Though she wasn’t actually physically swelling, she felt like she should have been with the amount of cream pumping into her.

Finally she felt her muscles unclench ever so slightly, and felt, as well as heard, the thick splatter of stallion-cum pouring out of her. It would splotch and plop to the wood floor with each convulsion by the Doctor, as he kept ejaculating into her… 15, 16,17… with each mini-thrust she groaned… loving the feeling of complete fullness and the naughty sounds of his cum splattering to the ground since there was no room left inside her for it. Finally, shot 19 was a bit weaker, and shot 20 was the last before she heard the doctor take in a deep breath.

“You *huf* OK there stud- *huf* stud-muffin? *huf* You shouldn’t *huf* *huf*, hold your breath like that.” Derpy wheezed as she teased the Doctor.

She felt his cock rapidly shrinking and receding from her love-tunnel with a bit of regret, the heavy still flared cock head spreading her lips and straining them briefly before coming out with a loud squelching pop. The obscene sound and feel of what felt like a full pint of cum sloshing out of her and splashing onto the ground made her chuckle.

“Wow, Doc when you said I was your first I didn’t know you had saved up for me this whole time too!”

The Doctor also began to chuckle and leaned down to plant a kiss on Derpy’s forehead.

“You little scamp you, I’ll have you know I ‘practiced’ just this morning for you, this is only a half-load!”

Derpy wiggled her hips seductively, “You’re gonna have to prove THAT to me Doc, tomorrow you’re forbidden from any ‘practice’... I wanna see this ‘full-load’!”

Derpy stretched her head up and stole a kiss from the Doctor. “I love you, Doc.”

“I love you too, Derpy”

Author's Note

Second iteration of my weekly (biweekly? daily? monthly?) Derpibooru commentfic writing adventure.