GREEN   28   0
   3492 21.17 KB    494

Derpcest

By Shroooomy
Created: 2025-08-16 01:29:26
Expiry: Never

  1. Derpcest:
  2.  
  3. Requested by: Anon
  4.  
  5. All characters in this story are 18+
  6.  
  7. > Dinky hooves had suffered through the awkwardness of living with her mom her entire life.
  8.  
  9. > But ever since she had reached sexual maturity, things have only gotten stranger in the hooves household.
  10.  
  11. > Derpy had sat Dinky in the living room and had placed a box of sex toys on the table.
  12.  
  13. > Derpy sat opposite of Dinky looking down at the sex toys nervously
  14.  
  15. > “So…Ummm….Where would you like to start?” Derpy asked, biting her hoof
  16.  
  17. > Dinky leaned her head along her hoof, which was positioned over her chairs armrest.
  18.  
  19. > Dinky stared with exhausted, lidded eyes at her mother who was wearing nothing but a red towel over her lap.
  20.  
  21. > “I ummm….I use this one the most…” Derpy began, pointing to a barbed purple dildo around ten inches long and four inches thick
  22.  
  23. > “B…But you’re much smaller than me….And haven't had any fillies of your own…So you're probably a lot..tighter than I am…”
  24.  
  25. > Derpy looked up at at Dinky who’s expression remained unchanged
  26.  
  27. > Derpy bit her tongue then picked up a book off the floor at her hooves
  28.  
  29. > The book was titled ”Standardized sex education manual for young ponies.”
  30.  
  31. > This was Dinky's book.
  32.  
  33. > Provided to her by the Equestrian Education Department to help developing fillies learn about sex in lieu of the proper sex education classes which had been removed from classrooms six years before Dinky was even born due to a number of controversies surrounding the program
  34.  
  35. > Dinky tried to hide the book from her mother because she knew something like this would happen.
  36.  
  37. > Derpy flipped through the pages, landing on a page with a series of questions which Dinky was supposed to answer privately in the allotted lined spaces below each question.
  38.  
  39. > Derpy began to read from the book out loud to Dinky
  40.  
  41. > “Do you…ummm….” Derpy stuttered “Do you ever feel…excited when looking at other ponies?”
  42.  
  43. > Derpy looked up at Dinky and smiled rather uncomfortably
  44.  
  45. “No, mom.”
  46.  
  47. > Derpy had a taken-aback expression
  48.  
  49. > “Okay…That's…Good?” Derpy replied, scratching her head
  50.  
  51. > Derpy looked back down at the book and continued
  52.  
  53. > “How does this make you feel?” Derpy muttered
  54.  
  55. > Derpy thought for a moment then began flipping the pages
  56.  
  57. > “But…You said you don't…Is their anything in the book about that?”
  58.  
  59. > Dinky’s lip junted upwards as she tried to contain her frustration
  60.  
  61. > “And.. What about sex toys…And…Oral sex?” Derpy asked “This book doesn't go over any of that.”
  62.  
  63. “It's an educational guide, mom. Not an in-depth- how-to-have-sex instruction manual.” Dinky explained flatly
  64.  
  65. > “But…What if you're ever in that situation?” Derpy asked as she frantically flipped through the pages
  66.  
  67. > “To perform oral all I do is put “it” in my mouth and suck.” Dinky replied
  68.  
  69. > Derpy's eyes jumped back at Dinky
  70.  
  71. > “How did you know!? Is there another book you’ve been reading?”
  72.  
  73. “No mom, I go to school.” Dinky snapped “The ponies in my class aren't exactly discreet about their sexual activities. And they’ve been having sex way before the school sent us this stupid book.”
  74.  
  75. > “Have…Have you been…” Derpy looked down at the book, reading the first line of text that caught her eye
  76.  
  77. > “Sexually intimate with another pony?”
  78.  
  79. “Mom.” Dinky leaned forward “When do you think I would find the time? When I’m not at school I’m here with you! And have I ever invited anypony over to the house?”
  80.  
  81. > “No…Not that I know of.”
  82.  
  83. “And do I go to parties? Or hang out with friends?”
  84.  
  85. > “No…You…You tell me all the time about how you don't have any…”
  86.  
  87. > Derpy thought, looking like she was trying to word the next part of her statement very carefully
  88.  
  89. “Mom, it's fine.” Dinky said gently placing her hoof over her mom's wrist “I appreciate what you're doing but it's not necessary. I’m not, and probably will never be sexually active.’
  90.  
  91. > “Why not?”
  92.  
  93. “Because I'm not…popular…”
  94.  
  95. > Derpy stared blankly at Dinky
  96.  
  97. “Or…conventionally attractive…” Dinky groaned, adding flair to her confession with a frustrated roll of the eyes
  98.  
  99. “Oh that's not true!” Derpy laughed “you have a really nice butt! It's so big and round! I bet lots of ponies would love to have “sexual intercourse” with you!”
  100.  
  101. > “Mom, I’m fat.” Dinky sighed
  102.  
  103. > “Oh, you're not fat.” Derpy chuckled, “You’re what ponies used to call me when I was your age!”
  104.  
  105. “And what was that?”
  106.  
  107. > “Breedable!”
  108.  
  109. > Dinky cringed at both the fact her mother was called breedable in high school and that her mother that she herself was “breedable”
  110.  
  111. > Though, the title did fit
  112. > Her mother had become pregnant with her at the age of sixteen in what Derpy described as a “celebration” in the boys locker room after a big win against an out of county junior hoofball team
  113.  
  114. “Mom! Stop being Gross! I don't wanna hear about what teenage ponies called you twenty years ago.”
  115.  
  116. > Derpy began to grab her ass, squeezing it and letting go.
  117.  
  118. > Her mother's ass jiggled with each release of her hoof
  119.  
  120. > “Your mom was on the high school cheerleading squad you know.” Derpy said, biting her bottom lip “I was the most popular mare in school for quite a while.” Deroy bragged, still staring at her jiggling butt
  121.  
  122. “And then you got pregnant.” Dinky huffed
  123.  
  124. > “Yeah….” Derpy sighed, her smile slowly fading
  125.  
  126. > Derpy sat for a moment in uncharacteristic silence, until jumping back to life, appearing to recognize the unintentionally hurtfulness of her time
  127.  
  128. “I mean! No! You…You were planned!” Derpy panicked
  129.  
  130. > Dinky again rolled her eyes
  131.  
  132. > Though, all evidence pointed to her birth being an accident, she liked to maintain skepticism of the terms regarding her conception.
  133.  
  134. > She wouldn’t put it past her mother to want to be a mother at sixteen.
  135.  
  136. > Dinky’s opinion of her mother's judgment was pretty low.
  137.  
  138. > Not lower than her opinion of her mom's intelligence or social awareness.
  139.  
  140. > But low enough to where she could see her mom thinking that becoming teenage pregnant would be some kind of “adventure”
  141.  
  142. > Though, it’s far more likely that her mother had never used condoms during her cheerleading days
  143.  
  144. > And that was probably a big part of the reason she was treating this “sex ed” stuff as seriously as she was.
  145.  
  146. > To prevent Dinky making the obvious mistakes she had when she was in high school.
  147.  
  148. > Dinky physically shivered whenever she remembered how sexually open her mother was at her age
  149.  
  150. > “Okay, remove the towel from your lap.” Derpy instructed
  151.  
  152. “Why?’
  153.  
  154. > “Because I want to show you how everything works!” Derpy beamed
  155.  
  156. > Derpy and Dinky both removed the towels which they were both naked under (one mare doing so with more enthusiasm than the other.)
  157.  
  158. > Dinky’s teats were perky and her nipples were pointed.
  159.  
  160. > Derpy’s teats in the other hoof were, while far larger (so big in fact that they forced the mare's thighs apart.)
  161.  
  162. > Her nipples were slack and her areolas were larger and always had this swollen look to them.
  163.  
  164. > Dinky had seen her mother’s teats more times than she liked to admit.
  165.  
  166. > Her mother was rather laissez faire about nudity, which in turn made Dinky more open to nudity than her peers, who all found Dinky’s casual, flagrant nudity in the school's change rooms to be more than off-putting.
  167.  
  168. > Dinky’s conditioned casualness towards having what should be her privates exposed was only partially why the mare staggered behind the other ponies her age in terms of popularity.
  169.  
  170. > Dinky’s cheeks turned red
  171.  
  172. > Not in a “flushed in sexual excitement” sort of way.”
  173.  
  174. > More in a “Embarrassed to be alive” sort of way
  175.  
  176. > Dinky still wasn't sure what to do when she felt embarrassed
  177.  
  178. > The feeling of embarrassment/shame never approached Dinky.
  179.  
  180. > This is mostly due to the aforementioned conditioning-to-nudity she had been raised under.
  181.  
  182. > Though she did feel a ton of second hoof embarrassment when it came to her mother.
  183.  
  184. > Who appeared to live a life blissfully incapable of feeling either shame or self awareness.
  185.  
  186. > Dinky crossed her hooves over her chest before looking up away.
  187.  
  188. > The corners of rooms seemed to become much more interesting on the rare occasions she experienced embarrassment.
  189.  
  190. “This is so stupid.” Dinky grumbled
  191.  
  192. > Derpy adjusted her teats and dropped them on the table in front of them. Causing the sex toys strewn across it to jump.
  193.  
  194. > “These are teats.” Derpy began to explain with her snout to the sky and eyes closed “They are only supposed to produce milk during pregnancy, however due to my families long history of incest my teats have been producing milk for the past twenty years.”
  195.  
  196. > Dinky scowled
  197.  
  198. “Wait….You’re only supposed to produce milk when you're pregnant?”
  199.  
  200. > Derpy nodded happily
  201.  
  202. > “Do you produce milk?” Derpy asked excitedly
  203.  
  204. “I mean…Sometimes…” Dinky replied looking worryingly at her teats
  205.  
  206. > Dinky exchanged glances between her mom and teats for a long moment, wearing a face of both concern and disbelief.
  207.  
  208. “That CAN'T be true!” Dinky chuckled, “My teats leak milk all the time! And I’m not….”
  209.  
  210. > Dinky stared at her mom for about five seconds who was nodding her head in disagreement with the most confident smile.
  211.  
  212. > Dinky could somehow see her mom's eyes smiling behind her shut eyelids
  213.  
  214. “Gimme that book!” Dinky barked, reaching under the table and grabbing it from the fluffy carpet floor
  215.  
  216. > Dinky flipped through the book, finding the page on lactation which read:
  217.  
  218. > “After impregnation, mares will begin to produce milk.
  219.  
  220. > Dinky gulped
  221.  
  222. “No….This can't be true…I’ve never even done it before!
  223.  
  224. > Derpy reached across the table and ruffled Dinky’s mane
  225.  
  226. > “Don’t worry Dinky! All the mares in my family have leaky teats!”
  227.  
  228. > Dinky placed her hooves along her temples, her pupils drifting in opposite directions giving her a slightly cockeyed expression.
  229.  
  230. “You mean this entire time I’ve been leaking milk all over the place thinking it was normal!?”
  231.  
  232. > Derpy started to scratch the back of her neck
  233.  
  234. > “I mean…This isn't a problem is it? I thought you'd be excited to hear how unique you were.”
  235.  
  236. “There is nothing exciting or unique about being a walking, talking milk faucet!”
  237.  
  238. > Dinky grabbed underside of each of her teats and stared down the barrels of her milk gushers
  239.  
  240. > Tiny bubbles of pale milk started to spittle from her udders
  241.  
  242. “You don't know how big of a problem this is mom! This could destroy my already awful reputation!”
  243.  
  244. “Is it really that bad?” Derpy asked
  245.  
  246. “Yes mom. I leak puddles in the school hallway daily. And I go through an entire roll of paper towels in a week.”
  247.  
  248. > “So that's where all the paper towels are going!” Derpy giggled “This whole time I thought you were just a really messy masturbator!”
  249.  
  250. “Mom. This is serious. I would appreciate a little respect for my passing dignity.”
  251.  
  252. > Derpy’s face scrunched in a face of legitimate concern
  253.  
  254. > “Okay, I’m sorry.” Derpy sighed
  255.  
  256. “Thank you.” Dinky replied, turning back to her teats
  257.  
  258. > “Well…” Derpy thought “Maybe try squeezing them together…”
  259.  
  260. “Why would I squeeze them together?”
  261.  
  262. > “To get the milk out?” Derpy suggested
  263.  
  264. “Do you think that would work!?” Dinky asked abandoning her usual skepticism of her mothers logic
  265.  
  266. > “Well…Let's just see how pent up you are, then I can see what I can do.”
  267.  
  268. > Dinky placed her hooves Along her teats and gently pressed them together.
  269. > Drops of milk began to drip down her each of her teats
  270.  
  271. > Derpy started to clap
  272.  
  273. > “That's amazing Ditzy! You're just like me!”
  274.  
  275. “What do you mean?” Dinky laughed nervously, hooves trembling
  276.  
  277. > “I guess it was obvious considering your size!” Derpy giggled, booping her daughter's right nipple “I just mean that in a couple years, your teats will be as big as mine!”
  278.  
  279. “Oh, Celestia…” Dinky gulped
  280.  
  281. > “Isn't this educational, Dinky!” Derpy clapped
  282.  
  283. “So not only are they going to keep leaking, but they're going to get bigger!” Dinky shouted, throwing her right hoof over her heart
  284.  
  285. > “Yep!” Derpy nodded “And I can already tell you’re going to look great with teats as big as mine!”
  286.  
  287. > Dinky began to hyperventilate
  288.  
  289. > “It's probably why your butt’s been growing so big! To carry the MASSIVE tits you’ll be lifting EVERYWHERE you go!”
  290.  
  291. “Is there any way to stop them from growing!?” Dinky snapped
  292.  
  293. > “Stop them from growing?” Derpy asked, scratching her head, “Why would you want to do that?”
  294.  
  295. “Because I don't want to look like a cow, mom!”
  296.  
  297. > Derpy looked down at her own tears “Y…You think I look like a cow?”
  298.  
  299. “No mom! I think you look wonderful!” Dinky cried “But…I…I’m not like you…And I don't wanna be stared at for having giant bucking tits swinging between my legs! I…I…I just want to be at least somewhat normal!”
  300.  
  301. > Derpy slung her hooves along her chest and frowned, clearly offended by her daughters honesty.
  302.  
  303. “Mom! You gotta help me! Please!”
  304.  
  305. > Derpy tapped her hoof against the floor looking up, trying to convey her irritation using all but words.
  306.  
  307. “Mom?”
  308.  
  309. > Derpy bit her tongue and scrunched her face
  310.  
  311. > “Cow….” Derpy grumbled under her breath “Think’s her mom’s not pretty…I was the cutest cheerleader in the junior Wonderbolts cheerleading academy…”
  312.  
  313. “Mom!” Dinky yelped
  314.  
  315. > Derpy's eyes widened, seeming to escape her trance by the sound of her daughter whining
  316.  
  317. “I want you to help me.” Dinky ordered
  318.  
  319. > “Well….” Derpy thought “I could always help you drain them.” Derpy suggested
  320.  
  321. “Drain them?”
  322.  
  323. > Derpy nodded agreeably
  324.  
  325. > “Nurse Redheart drains my teats weekly at the hospital! Though.. She uses a pretty expensive machine…I think it was initially designed for cows or something…” Derpy said, rubbing her chin “And it costs a lot of money to operate…And I think having both of us get drained weekly would be incredibly costly.” Derpy nodded
  326.  
  327. > A smile crept across her mothers face.
  328.  
  329. > But Dinky was too in her own head, worrying to notice
  330.  
  331. “Well we gotta do something!” Dinky continued “I don’t want to live the rest of my life like some kind of…Farm animal!”
  332.  
  333. > Derpy leaned forward towards Dinky
  334.  
  335. > The floor ached as her mother shifted her weight from her seated position.
  336.  
  337. > Derpy encroached into Dinky’s space so tightly, that the young mare felt her mothers hot blueberry- muffin flavored breath kiss her burning cheeks.
  338.  
  339. “We can always do it orally.” Derpy whispered, adorning a wet sultry tone that Dinky found unnerving coming from her mother
  340.  
  341. “W…What do you mean orally?” Dinky whispered fearfully
  342.  
  343. > “You know…” Derpy hummed, flicking a thick strand of her blonde mane from her face with her hoof.
  344.  
  345. > “A quick mother-daughter relief session.” Derpy proceeded, her wet lips smacking with each syllable as she slipped deeper into this jarring persona which struck Dinky with terrible unease
  346.  
  347. > “I think it would help you lose all that milk weight. And it would cost us nothing but…Maybe some slight awkwardness. But what's that in exchange for a good appearance?”
  348.  
  349. > Dinky looked down at her teats
  350.  
  351. “You can't be serious.” Dinky challenged “Is this because of the cow comments? Because you know I wasn't being literal, nor was I trying to slight your appearance. I was merely trying to say how your very….Distinct appearance wouldn't do me any favors…”
  352.  
  353. > Derpy placed the pointed edge of her hoof over the nipple of her right teat
  354.  
  355. > “Then let mommy help you. I wouldn't want my precious daughter to feel uncomfortable in how she looks…Mommy knows all too well how that can feel.”
  356.  
  357. > The pupil in Derpy’s left eye (which was significantly smaller than her right pupil) drifted towards the floor sadly.
  358.  
  359. “I…I didn't mean to offend you.” Dinky snuggled
  360.  
  361. > Derpy gently pressed Dinky into her chairs cushion.
  362.  
  363. > Her daughter's body crooked at an awkward angle along the seat.
  364.  
  365. > Her upper back flat along the chairs backside as her rump teetered halfway off the seat.
  366.  
  367. > Derpy slid down between her daughters legs in what Dinky could only describe as composed “snake-like” movements
  368.  
  369. > Once Derpy was on her knees she split Dinky’s legs wide apart.
  370.  
  371. > Her mothers hot blueberry breath stirring between her legs. Kidding her teats and marehood
  372.  
  373. > Derpy licked her lips and tilted her head slightly to the right, slowly approaching her daughter's right teats with her glistening pursed lips
  374.  
  375. > Dinky squirmed, but only a tad
  376.  
  377. > She was wrestling between a building sexual excitement and her rationality.
  378.  
  379. > Her mother hadn't ever touched her like this before.
  380.  
  381. > And the fact that it was exciting her made the young mare feel filthy in a low-class-fucked-up kinda way.
  382.  
  383. > Derpy placed her mouth on Dinky’s teats
  384.  
  385. > The sensation was predictably, warm and wet
  386.  
  387. “Mom!” Dinky cried
  388.  
  389. > “Yes honey?” Derpy asked, teat still between her tight lips
  390.  
  391. > “T…Take my…N…Nipple out of your mouth!”
  392.  
  393. > Derpy rolled her eyes and unlatched her lips from her daughter's nubby nipple.
  394.  
  395. > The act elicited a loud “pop!” And caused Funky to throw her head back and wince
  396.  
  397. > “Relax honey! Mommy is going to help!”
  398.  
  399. “I…I’m not sure I want you to help!” Dinky cried trying to choose her words carefully
  400.  
  401. > Derpy sighed impatiently
  402.  
  403. > “Why not?”
  404.  
  405. “Because you're my mom! And…We…We shouldn't be doing this!…..I….I don't know if you realize it or not, but this is VERY inappropriate!”
  406.  
  407. > Derpy leaned her head along her hoof similar to how Dinky was at the start of the “lesson”
  408.  
  409. > “Dinky, do you believe I would do anything to hurt you?”
  410.  
  411. >....
  412.  
  413. > “Intentionally.” Derpy specified
  414.  
  415. “No?”
  416.  
  417. > “Dinky! I love you!” Derpy giggled “There is nothing I want more in this world than to make you happy.”
  418.  
  419. > Dinky blushed
  420.  
  421. > “Maybe I’m going too fast.” Derpy sighed “I want you to have a healthy sex life and I thought that maybe if I gave you some hooves on advice you would have a better understanding of what to do the day you met your special somepony.”
  422.  
  423. > Derpy hung her head
  424.  
  425. > “If you don't want to do this we don't have too…But I was only trying to do what I thought was right.”
  426.  
  427. “Mom…” Dinky said calmly
  428.  
  429. > “But I’m still upset that you compared me to a cow! And when. you said you didn't want to look like me it made me very sad and angry…And when I get frustrated I can usually bite my tongue…bottle myself up until I can get home to masturbate..”
  430.  
  431. > Dinky rolled her eyes
  432.  
  433. > Of course she would bring up something like that during her heartfelt monologue
  434.  
  435. > “But seeing you.” Derpy continued “With your teat’s out and dripping milk, with your marehood tucked between your chubby thighs and breedable ass…I…I lost control.”
  436.  
  437. “Mom….Are you sexually attracted to me?”
  438.  
  439. > Derpy didn't reply
  440.  
  441. > At least not immediately
  442.  
  443. > Instead she looked to the floor inhaled deeply and exhaled
  444.  
  445. > “Mommy’s been very lonely since your dad left.”
  446.  
  447. > Dinky deflated
  448.  
  449. > She actually started to feel guilty
  450.  
  451. > Though, she didn't know exactly why
  452.  
  453. > It probably had to do with the fact that her mom didn't have any real friends outside of ponies she knew at the post office, who she only spoke to at work.
  454.  
  455. > Her mom, outside of Dinky, didn't have a social life.
  456.  
  457. > The spent her time outside of work and chores reading either romance novels or stuffing her face with muffins.
  458.  
  459. > Her mom didn't even have a family to reach out to.
  460.  
  461. > She left home with her dad after getting pregnant.
  462. > And if there was one thing Derpy would not speak of, it was her parents.
  463.  
  464. > This had always been one of the more alarming peculiarities of her mother (of which Depy had in spades)
  465.  
  466. > But unlike other topics and shortcomings. Derpy wasn't shy to admitting her faults, or talking about the thousands of embarrassing things she had done throughout her life.
  467.  
  468. > Her mother had gone into the graphic details regarding her ensemble of sexual partners, masturbation habits, and the favorite types of sex of her ex-lovers.
  469.  
  470. > But her home life seemed to be a much more touchy subject.
  471.  
  472. > One which she refused to even acknowledge
  473.  
  474. > “Derpy Hooves” wasn't even her real name.
  475.  
  476. > “Derpy” was a pet name Dinky’s father gave her
  477.  
  478. > And “Hooves” was her father's last name
  479.  
  480. > Dinky didn't even know her mother's real first or last name!
  481.  
  482. > Dinky often wondered if Derpy’s parents were the reason her mom was the way she was
  483.  
  484. > The possibility that she and Derpy share a similar dynamic to what Derpy and her parents frightened her.
  485.  
  486. > Dinky placed her hoof on her mom's chin and guided her head to face her
  487.  
  488. “Mom…I…” Ditzy stuttered
  489.  
  490. “If it makes you feel better…You can suck on my teats all you want.”
  491.  
  492. > Derpy smiled as she placed her lips over Dinky's right nipple and slowly began to suckle
  493.  
  494. > Dinky began to wonder what Pandora's box she had just opened.

The misadventures of Derpy's Boobs 1.5

by Shroooomy

The Misadventure Of Derpy's Boobs 1.6

by Shroooomy

The misadventures of Derpy's Boobs 1.7

by Shroooomy

The Misadventures of Derpy's Boobs 1.8

by Shroooomy

The Misadventures of Derpy's Boobs 1.8

by Shroooomy