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The Misadventures of Derpy's Boobs 2.666

By Shroooomy
Created: 2022-11-26 23:57:31
Expiry: Never

  1. Derpy:
  2. >The entire time we walked it seemed like neither of us could help but stare into each other's eyes.
  3. >I found so many new ways to love Fluttershy that I had never considered before. >She’s beautiful, sexy, and cares about me like no other pony. >I think I’m in love for the first time in my life.
  4.  
  5. >The only pony that makes me feel this way is Twilight, but she’s twice the mare I’ll ever be. >But still, Fluttershy is very different from Twilight. She’s my best friend and more. I don’t know if these feelings are right, but now more than ever I find myself in need of a friend.
  6. >I don’t want to mess this up but the long lashes curling over her gorgeous eyes have me in a trance. >Her body is perfect in every way, from her wiry pink mane to the tips of her wings.
  7.  
  8. >“Are you ready for our sleepover?”
  9. >“More excited than I have been in my entire life!! Let's cut through Sweet Apple Acres, I know a shortcut!” >We trotted across the Apple’s farm and walked through the fields and hills.
  10.  
  11. “One day my house is going to look just like the Apple farm! I’m going to grow every kind of vegetable and be a real farm pony!”
  12. > “That sounds nice…If you ever need any help you know who to ask.”
  13. “Yeah! I’m going to ask Twilight!”
  14. >“That's not what I meant. What’s so amazing about Twilight anyway?”
  15. >I was dumbfounded, how could she not see how beautiful Twilight is?
  16.  
  17. “She’s an angel! No pony is more perfect than Twilight Sparkle. It’s a fact.”
  18. >“Well I wouldn’t go that far. But I’m glad that she’s inspired so much positive change in your life. You never went to the library until Twilight moved in, what do you two do there anyways? You only ever leave your house to visit Twilight and She tells me that sometimes you’re there from the time it opens until closing.”
  19. “Oh my gosh! We have so much fun! I watch her do magic, read books and write letters! Sometimes she even lets me do stuff for her like turn the pages or dip her pen in ink!”
  20. >“Oh…Ummm…That sounds like lots of fun I guess?”
  21.  
  22. “It really is! We talk for hours about all sorts of fun stuff! Just between you and me. Sometimes when her back is turned I lean in really close and smell her mane. Have you ever smelled her mane? Not just in passing, but really sniffed it?”
  23. >“No…I can’t say I have.”
  24.  
  25. “Well...Have you ever noticed how beautiful her eyes are?”
  26. >“I mean…She has nice eyes but I wouldn’t say they’re…”
  27. “Have you ever gone through her underwear drawer?”
  28. >“Why in Equestria would I do that!?”
  29. “To take her underwear of course! But don’t worry, I always return them after a couple of wears. When she’s not looking I sneak back up stairs and return them, but not before running my tongue over every single pair of her delicious…”
  30. > “That's enough! I don’t need to hear anymore!” Fluttershy shouted
  31.  
  32. "It’s okay if you don't understand. Twilight and I have a very special bond, you wouldn’t get it.”
  33. > “And what kind of bond is that?”
  34. “We’re soulmates. Twilight and I are inseparable, I can’t live without her and she can’t live without me.”
  35. > “Don’t you think that sounds a little… ridiculous?”
  36. “No.”
  37.  
  38. > “B-But why Twilight of all ponies!? What makes her so special!?”
  39. “She’s perfect, and I am hers forever as she is mine. I love her more than I even love myself and would happily lay down my life for her. I hope you don’t judge me for telling you this.”
  40. >....
  41.  
  42. > “Don’t worry, I’ve always thought you were crazy.” She giggled
  43. “Well…At least I don’t work at a milk bar!” I shot back playfully
  44. > The two of us laughed
  45. > “Don’t worry Muffins I’ll never judge you for feeling the way you do. I’m sure somepony feels the same about you.”
  46.  
  47. > The two of us hugged, from the corner of my eye I saw a storm rolling in over Old Ponyville, we wouldn’t make it to either of our houses before the rain started pouring
  48. “Fluttershy, it looks like a really bad storm is coming.”
  49. > “Oh no! We better hurry.”
  50. “Well…I know somewhere we can stay for the night.”
  51. > “Where?”
  52.  
  53. >.....
  54.  
  55. > I cracked open the door to the shed and stumbled around looking for the lantern
  56. > “Are you sure Applejack won’t mind us sleeping in her shed?”
  57. “Of course not! Applejack lets me come in here whenever I like.”
  58. > I dragged my hooves over the chest high shelf until it nudged the lantern. Beside it was a small box of matches.
  59. > I lit the match and stared into the flame for a moment.
  60. > “Don’t hurt yourself with that fire.” Fluttershy nagged
  61. > I rolled my eyes, she is such a motherly mare.
  62.  
  63. > “Whats this thing?”
  64. > I turned and saw Fluttershy running her hoof over the milking machine
  65. > “Is this a milker?” She asked in awe
  66. “Yeah.” I laughed “Applejack bought it for me”
  67. > “These are really expensive and rare....You know that she’s probably selling your milk to somepony right?”
  68. “I know…I always assumed that she was dumping it somewhere….I never knew about the mare milk industry until I met Milky…And then Filthy Rich was talking about it at the party…I don’t know how I feel about all of it…It’s been a really confusing day.”
  69.  
  70. > The two of us sat over the pile of hay, I removed what little reminded of my dress and rested it over my lap.
  71. > As we sat we stared into each others eyes. I was feeling so happy and excited.
  72. > I don’t know why either of us were so concerned about going to the Pinkies party, neither of us even liked parties.
  73. > Just being together was perfect.
  74. > I was starting to wonder what kind of pony I had become
  75.  
  76. > Fluttershy wrapped her leg around my neck.
  77. >“Did you have a good time at the party?”
  78. >I nodded distractedly
  79. > “Fluttershy, something has be on my mind for a while now….And I have to ask...Why did you come to the party with me?”
  80. > She stared at the floor with an uneasy expression “Oh…I…I just…Thought it would be fun.”
  81. “Fluttershy, you hate parties.”
  82. “Well, I had never gone to a party with you before…And I had a really great time.”
  83.  
  84. > “Do you like me?” I asked
  85. > “Muffins……”
  86. > “Because I like you…I like you a lot…But we’re friends and…I’m not sure if liking you like that is right.”
  87. > Fluttershy poked my nipple and began rubbing it in slow circles
  88. > “Do you like that silly pony?” Fluttershy she teased
  89. > “Y-yeah…It’s nice.”
  90. “Your nipples are so soft.” Fluttershy giggled
  91. “You can thank Applejack For that.”
  92.  
  93. "Oh, Muffins." She moaned "I always thought you were so pretty."
  94. >I pushed her hoof away and sighed
  95. "Is it just me, or were things easier when we were younger?
  96.  
  97. >“What do you mean?”
  98. “Well…At the party you reminded me about the first time we tried wine.”
  99. >“What about it?”
  100. “You still didn’t tell me what happened after you brought me home.”
  101. >“Well…I brought you upstairs and you laid in bed…You said you were cold and you wanted me to lay with you…So I did."
  102. “Then what happened?”
  103.  
  104. > “You said that I was your best friend…And that you really liked me…And…And then I kissed you….I don’t know what came over me but in that moment I just felt it…I really like you Muffins.”
  105. > I was shocked, I always wondered what happened after that night but was to embarrassed to ask. All this time I thought that I never kissed another pony…It was so illuminating.
  106. “So…You’ve always had a crush on me?”
  107. >“Yes…Ever since that night…Maybe even before…I don’t know when it started…But I’ve always admired you.”
  108.  
  109. >Fluttershy hid her face behind her hooves and I stared down at my chest. I felt decompressed, today was taking it’s toll like no other.
  110. “Who would have thought we'd end up here?”
  111. >“Thats the magic of friendship. You never know where you'll end up. And when you step back and think about it you feel…”
  112. “Empty”
  113. >“Oh…I was going to say peaceful”
  114.  
  115. “Fluttershy do you ever get scared?”
  116. > She rolled her eyes and gave me a sarcastic glare “You'll have to be more specific.”
  117. “Well…I've been afraid of growing up for a long time now. I don't feel the same as I used to and...I…I want to be happy…But I made a promise to my dad and ..."
  118.  
  119. > “Do you like me?"
  120. “Wha?...I mean, of course I like you Fluttershy.”
  121. > “More than a friend?” She pressed
  122. “I…I don’t know…You're my best friend in all of Equestria…And I wish more ponies were like you."
  123. >“Thats very sweet." Fluttershy laughed “I think of you a lot"
  124.  
  125. “Y-You do?”
  126. > “Of course…I..I really, really like you.”
  127. >Oh my gosh, this was it
  128. >“Well..I really, really like you too.”
  129. >Fluttershy rubbed her hooves together anxiously and looked away with a big grin across her glowing red face.
  130. >I stared the floor
  131. > What the heck do I say next?
  132. > Stupid brain just say something!
  133.  
  134. “Well…About that night…I remember feeling grown up…Pinkie was becoming a bakers apprentice, Rainbow was in the junior Wonderbolts academy, You wanted to open an animal sanctuary…There was such an electric feeling in the air that night. Like anything was possible.”
  135. > “Yeah…I remember when I wanted to open a sanctuary” She laughed awkwardly
  136. “But still want to don’t you?”
  137. > “It sounds like a lot of fun…But I don’t have the bits. That was just talk, we were fillies.”
  138. > I sighed
  139. “Fluttershy what happened?”
  140. >“I guess we all grew up. What are you getting at Muffins?”
  141. >I felt my heart race. I got a really uneasy feeling in my stomach
  142. > I didn’t want to go through with this anymore
  143. “Fluttershy…Maybe we shouldn’t.”
  144. > “Muffins…
  145. >“I’m scared.!I thought I wanted this but maybe I don't! What if this ruins our friendship?…I don’t want to stop being friends with you!”
  146. > “Muffins, It won’t, I promise.”
  147. “But what happens after! What if it’s really bad? What if we stop being friends…Not immediately but we just…drift apart like everypony else?”
  148. > “Where is this coming from?”
  149. “I don’t want to grow up…It's scary and hard and I don't think I can do it! I want things to stay just the way they are.”
  150. >...
  151. “Are you happy with the way things are?”
  152. > My eyes started to water and my mind went to the strangest places
  153. > Flight school
  154. > Applejack
  155. > My dad
  156. > The mother I never met
  157. > I lost everything growing up
  158. > I didn’t want to lose Fluttershy too.
  159. > All I have in this world is my home and Fluttershy.
  160.  
  161. > “If it means anything…I’m nervous too.” She peeped
  162. “Why did everything happen…The way it did?” I asked trying not to cry
  163. > “What do you mean?”
  164. “Why does everypony leave me?”
  165.  
  166. >...
  167. >...
  168. >...
  169. >...
  170. >...
  171. > “I don’t know…Sometimes ponies just move on…Even if they don’t want to.”
  172. “It feels like all my good memories are ruined because…Because I can’t remember how things used to be without being remind about how bad things are now and it makes me feel empty. Do you think that we’ll ever be happy like again?”
  173.  
  174. > …
  175. >...
  176. >...
  177. > “I don’t know…I can’t give you happiness but I’ll always be there for you.”
  178. > She placed her hoof on my inner thigh
  179. > I still wasn’t sure, I put my hoof over hers and stopped her
  180. > We looked into each other's eyes
  181. “Promise? Even when things get hard?"
  182. > I pulled her hoof closer to my crotch and she giggled
  183. > “I Promise, Muffins.”
  184. "M...Maybe growing up isn't that bad..." I giggled
  185. > "See?" She laughed "When we're done you won't have to worry your silly little head about such things ever again."
  186.  
  187.  
  188. >Fluttershy slowly began to lower her head into my chest and started to lick my boob upwards towards my nipple.
  189. >“Your milk tastes so good.” Fluttershy moaned
  190. > She slid her tongue up to my tit and started to twist it around my nipple in a circular motion
  191. > She leaned back and fell to her rump across from me and pushed her breast aside and spread her legs apart.
  192. > “You like it? My little kitten?” She hummed
  193.  
  194.  
  195. >I’ve only seen other mares privates in pictures, hers looked so pretty and compact. Nothing like mine which was flabby and open.
  196. > “Be a good little pony and show me yours.”
  197.  
  198. >Nervously I slid the dress off my lamp and spread my legs as far as I could, pushing my breasts to the side.
  199. >“Oh…Muffins…You need to clean yourself.”
  200. “Huh? What do you mean I do…”
  201. >She rested her hoof over my lips and leaned between my legs.
  202. >“Shhh….Poor little Muffins….Don’t worry…I’ll clean you and you’ll be good as new.”
  203.  
  204. >When her tongue met my crotch, it felt so warm and wet. I closed my eyes and felt myself slipping away
  205. "I've never done this before.” I trembled
  206. > “Don’t worry...It feels really good.”
  207. >The two of us locked eyes, she shot me a small smile before she sunk back between my legs and shoved tongue into my pussy.
  208. > Fluttershy dragged her hooves over my breasts as her warm breath made me squirm and the tip of her tongue prodded my pussy.
  209.  
  210. > I began to smile, It feels really nice
  211. >She dragged her tongue over my pussy lips slowly before she forcing it deep inside me
  212. >My legs shivered as she punched my privates with her tongue
  213. >I closed my eyes and lost myself in dizzying ecstasy
  214. >My breaths shorten and my heart beat feverishly. I felt like I was falling backwards into a pool of absolute pleasure
  215. >I felt loved
  216.  
  217. > Her head popped up from between my legs. Her lips dabbed with thin strands of cum that dripped onto the floor.
  218. > Fluttershy started to rub my crotch and tugged the lips of my snatch like an elastic band.
  219. > "You're so stretchy down here." She said pulling on my vulva
  220. > "Isn't it supposed to be?" I
  221. > “Are you sure you’re a virgin?” She asked in a playful tone, raising an eyebrow and adorning a coy little smile.
  222. “Yes!...I…I mean…I like…big toys and…And I’m home a lot so I….You know…touch myself a lot.” I was starting to feel embarrassed.
  223.  
  224. > “You’re so naughty. I was hoping to pop your cherry, but it looks like you blew it out long ago.”
  225. “Ummm….S-Sorry?”
  226. > “Muffins, why are you so lewd…Say sorry.” She said in a soft, sultry tone
  227. “Ummm….Sorry?”
  228. > I was really confused, what the heck had gotten into her? And whats with this voice?
  229. > “You totally ruined yourself! I'm gonna have to start calling you Rarity." She chuckled
  230. "P-Please don't." I stammered
  231. > "Don’t worry my perverted little friend. I forgive you…I will always love you, no matter how naughty you are.”
  232.  
  233. > At a loss for words
  234. > She dragged her hoof across my crotch and collected my juices then started licking feverishly.
  235. "How does it taste?"
  236. > "Sweet like honey." She moaned
  237. > Her eyes were wide and mouth agape
  238.  
  239. >"Do you want to try?"
  240. I nodded nervously
  241. >She rolled herself onto the pile of hay beside me.
  242. >I positioned myself between her legs as she spread them wide
  243.  
  244. >Here crotch was already wet and her clitoris was winking excitedly
  245. >I wasn't sure where to start so I began lapping her crotch like an ice cream cone, moving my tongue over her lips and circling her clit when it peaked from behind her soft and puffy lips.
  246. >Her crotch tasted salty and the flavourful danced over my tongue like fire
  247. >I poked my tongue quickly inside her and felt her legs shiver
  248.  
  249. >Her pussy was tight and difficult to puncture, I felt her hoof rest over my mane as she gently pushed My face into her crotch
  250. >My snout was buried between her lips. I licked frantically making circles around the walls of her hole.
  251. >I felt a warm wet discharge shoot from her pussy as legs trembled in my peripheral vision.
  252. >"Oh, Muffins." She moaned “Good girl…Keep going…Don’t stop…You’re a good little filly…My little filly.”
  253. > When she released me I lifted my head and saw her face was flushed
  254.  
  255. >I crawled up towards her and I rested my mouth on her lips and the two of us embraced each other in a hug
  256. >Fluttershy dragged her hoof between the crease between my chest boobs.
  257. >I could feel the milk boil in my breasts as they pulsated and churned like a heartbeat.
  258.  
  259. > She slid downwards and rested her head a couple inches beneath my chest boob and teased my breast by lifting and dropping it repeatedly
  260. > The milk inside made a sloshing noise each time it hit my ribcage.
  261. > She then pressed her tongue over my nipple and began lapping it
  262. > A warm sensation washed over me.
  263.  
  264. > "Fluttershy….I'm gonna explode."
  265. > She laughed
  266. > “Do it on my face.” She said with a naughty grin
  267. > She stuck my nipple in my mouth and tugged on it with her lips roughly until milk started shooting from my nipples
  268. > She opened her mouth and stuck out her tongue as the milk covered her face, painting her wide smiling face white.
  269. > It felt like heaven and last for half minute, when I finally finished cumming Fluttershy was painted white in milk.
  270. > When the milk returned to a dribble she jumped forward and pressed her lips to mine, getting the warm and sticky milk all over my cheeks.
  271.  
  272. > "Oops." She cooed "Looks like I got my little Muffins all sticky."
  273. > She pressed her tongue to my cheek and licked a large gob of milk off my face
  274. > "Don't worry, I'll clean it all off my tiny lamb."
  275.  
  276.  
  277. >....
  278.  
  279. > The night continued in that fashion for hours until the two of us were exhausted.
  280. >When we finished the two of us wiped each other clean with our dresses and leaned back onto the hay while we listened to the wind blow.
  281. > Fluttershy soon fell asleep but I stayed up
  282. > I had sex for the first time and felt great
  283. > But it was more than just sex. It was love
  284. > A moment I shared with my best friend that we’ll both remember forever
  285. > I thought I was done having good memories.
  286. > Now that I’m older, I realize I’m in one of those moments
  287. > Maybe, I’ll never be this happy ever again
  288. > Maybe….it doesn’t matter.
  289. > Maybe growing up isn't that hard...
  290.  
  291. > I stood up and stretched my legs that were still electric from the awesome sex
  292. > “Where are you going?” Fluttershy asked with a gentle smile with her eyes peeking open
  293. “Just gonna stretch my legs and get some air.”
  294.  
  295. > “I’ll go too.” Fluttershy replied as she pulled herself up over shaking knees.
  296. > When we stepped outside the rain had stopped.
  297. > The air was warm and I spread my wings into the air and closed my eyes, embracing the pleasant summer air.
  298. > As I inhaled I got a whiff of a disturbing scent.
  299. > It smelled like burning…
  300.  
  301. > I opened my eyes and across the rolling hills of apple trees I saw a large ball of flame dancing in the distance
  302. “What's that?” I muttered to myself
  303. > I squinted and saw the flames were coming from Old Ponyville
  304. > My neighbourhood…
  305.  
  306. >ohoohnohono!
  307. > “What's happening down there?” Fluttershy asked rubbing her eye
  308. > Without hesitation I ran down the hill as fast as I could towards the flame
  309. > “Muffins?! Muffins come back!”
  310.  
  311. > My heart was pounding as I ran through the apple trees
  312. > Smoke and ember consumed the glowing orange night sky
  313. > I pushed myself harder as Fluttershy’s panicked voice bellowed from behind me
  314. > I don’t know what she was saying, but it didn’t matter.
  315. > I ducked into the forest, pushing branches away as I stumbled down the rocky path. I had never pushed myself this hard in my life.
  316. >But this was important, nothing was more important.
  317.  
  318. > When I reached the chain link fence I vaulted under the hole cut into it and ran down old main street
  319. > Smoke covered the sky, the abandoned buildings of Old Ponyville were stained by the flickering orange glow of the fire.
  320. > When I swung around the corner off old main street a wave of heat splashed over me.
  321. > Smoke pooled overhead and embers were flying across the sky
  322. > I could feel my eyes watering as my home burned before my eye
  323. “Don’crydon’tcrydon’tcrydon’tcrydon’tcrydon’crydon’tcrydon’tcrydon’tcrydon’tcry…” I whimpered
  324.  
  325. >It was gone
  326. >It was all gone…
  327.  
  328. > “Muffins!” I turned and saw Fluttershy standing in a sweat, while the reflection of flames curled in her eyes.“
  329. >Muffins!…Please!….Don’t go in there! Please…You’ll hurt yourself!”
  330. > Tears began to stream down my face
  331. > I looked back at house entombed in violent flames
  332. > There was nothing I could do.
  333.  
  334. > “Muffins!” She cried
  335. >I spun back around and saw Fluttershy’s walking towards me with her face covered.
  336. >Her mane whipping in the violent wind.
  337. > sparks flew wildly through the black smoke surrounding us.
  338. > When she got close enough she grabbed my hoof and tugged harshly
  339. > But I didn’t budge.
  340. > Instead I fell to my rump and watched the towering ball of fire erupt.
  341.  
  342. >The house was ablaze like a match head.
  343. > There was nothing I could do but watch the smoke plume from the flames with tears running down my face.
  344. > Fluttershy put her leg around my neck
  345. > "Muffins! We have leave!"
  346.  
  347. > I looked back at her and with trembling lips I cried
  348. "B..But this is my house..."
  349. > “I’m so sorry Muffins…I…I really don’t know what to say.”
  350. “H…How…How did this happen? W…Who would do such a horrible thing?”
  351. > “Muffins…”
  352.  
  353. > “S…Somepony did this! I…I know they did! I know…T…They did! I…I…I!”
  354. > I collapsed into Fluttershy and pressed my face into her shoulder and wept uncontrollably.
  355. “I can’t do anything right!”
  356. >“Muffins, this isn’t your fault.”
  357. > "I...I promised my dad that I would look after the house while he was gone!”
  358. > “But…Muffins…”
  359. “He never came back! He never should’ve left me home alone! I should've stayed with Applejack! I told him I wanted to stay with Applejack!”
  360. > My breaths were quick and sharp, I tried to compose myself but despite my efforts I simply couldn’t
  361. “But grown up ponies don’t cry! And…And grown up ponies don’t need babysitters!”
  362. > “Muffins…”
  363. “It’s been four years…I’m still not a grown up and I cry a lot…I…I don’t wanna be alone anymore….And I don’t want to be a grown up…I...I thought…Maybe if I was tough like him everything would be okay.…But I can’t do it! I just can’t…”
  364.  
  365. > Fluttershy rubbed my backside and leaned her head over my shoulder
  366. > “There, There….I’ve got you…” She cooed
  367. “Fluttershy…” I sniffled
  368. >“Yes, honey.”
  369. “Please don’t leave me…..Please don’t ever leave me….”
  370. > “It’s okay Muffins.” She purred
  371. > “I’m here for you….I’ll always be here for you.”

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