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The Misadventures of Derpys Boobs 2.1

By Shroooomy
Created: 2022-10-03 03:47:18
Expiry: Never

  1. > Fluttershy sat across from me rubbing her hooves together.
  2. > Our anxious energies circled around the table like an uncomfortable wind
  3. > I felt like I should say something but I was at a loss.
  4. >I was never good at romance.
  5.  
  6. > I looked around the room at all the ponies talking and dancing.
  7. > Most were my age and looked far happier than I’ve been in a long while
  8. > And no pony was bumping into things or tripping over their words.
  9. > How did they do it?
  10.  
  11.  
  12. > "You're awfully quiet, Are you feeling okay?"
  13.  
  14. "Yes…I'm fine."
  15. > "You're perspiring and you haven't sat still since we got here."
  16. “I’m just really excited…to be here with you…”
  17. > I gripped my cup and chugged a large drink of alcohol
  18.  
  19.  
  20. > I wish I could honestly tell her that I had feelings for her and that my needs were incredibly physical
  21. > My eye landed on her figure.
  22. > Her plump thighs sat atop the chair and coasted upwards into a perfect hourglass frame.
  23. > She had a coat that radiated like sunflowers and eyes that reflected my nervous image bleached in sparkling blue
  24.  
  25.  
  26. >I imagined running my hooves across her soft and buttery form like a sculptor.
  27. > Examining her every crevice with my awkward virgin hooves.
  28. > I wanted to see what mares did between sheets when the night is old and their bodies ached.
  29.  
  30.  
  31. > My teats began to tingle and I felt myself violently discharge into the tubes around my nipples.
  32. > Just picturing it sent my most tender areas into conniptions
  33. > I closed my eyes trying to think of something else but my orgasams were too powerful and I found myself in a loop of unending ecstasy.
  34. > I needed her hooves around me as much as I needed mine around hers
  35.  
  36.  
  37. > I felt a cloth run across my forehead and I shot my eyes back open
  38. > "Muffins?"
  39. > I shook my head and snapped back into reality
  40. > "Are you okay?"
  41.  
  42. "Yep….Just thinking."
  43. > She dabbed my forehead with a napkin
  44. > "Don't think too hard, You'll start spiralling."
  45. "Yeah…Wouldn't want that!"
  46. > She winked at me a giggled
  47. > “You’ll ruin your gorgeous dress.”
  48.  
  49. > Oh my gosh!
  50. > She winked at me
  51. > This was my chance
  52. > I had to say something
  53. “A..Are you…enjoying the party?”
  54. > “I’m having a wonderful time. I’m happy you found us a table near the door just in case I started to feel a little overwhelmed. I hope you don’t mind too much.”
  55. “Of course not. I wouldn’t want you to feel anxious.”
  56. > “You are so accommodating."
  57. >...
  58. “So…Is this like a proper date?”
  59. > “I guess it is…If you want it to be…”
  60.  
  61. “I…I don’t know.”
  62. > “Oh…Okay…”
  63. >...
  64.  
  65. > Why is dating so hard
  66. > I just want to touch my best friend's tits. Now we are sitting across from each other like strangers on a blind date
  67. > I've known her all my life. Why is this so awkward?
  68.  
  69. > I lifted my drink and took another big swig
  70. > “Don’t drink too much, you might get a tummy ache.”
  71. “I think I’ll be fine.”
  72. > “Are you sure?”
  73. > Fluttershy started to laugh out of nowhere
  74.  
  75. “What's so funny?
  76. > “Remember when Rainbow graduated from junior flight school and she stole a bunch of cider from the Apple farm”
  77. "Kind of?"
  78. > “You drank a lot that night.”
  79.  
  80. “I remember Pinkie fell out of the clubhouse and had to go to the doctor the next morning.”
  81. > “I remember that too…But do you remember anything else?”
  82.  
  83. “No…I remember throwing up…And you took me home.”
  84. > “And?”
  85. “I had a really bad stomach ache the next morning. Did something else happen?"
  86. > “Oh, no. You passed out as soon as you got into the door.” She laughed
  87. > Fluttershy took a sip of her drink and looked away.
  88.  
  89. “I miss those times.”
  90. > “We thought drinking made us so grown up.” Fluttershy said dreamily
  91. “I feel less grown up than ever.”
  92. > “Don’t worry, You haven't changed a bit.” she chuckled
  93. “Is that a good thing?”
  94. > “Oh Muffins, I always thought you were perfect.”
  95. “You..You too.”
  96.  
  97. > I felt something slide up my leg from under the table
  98. “Is that you?”
  99. > The sensation suddenly stopped
  100. > “No.”
  101.  
  102. > Her face was turning red and she was staring up at the ceiling.
  103. > I felt it again
  104. “There it is again!”
  105. > I looked under the table and saw Fluttershy’s legs crossed while she swung her hoof back and forth
  106.  
  107. > She was just as anxious as I was, only better at hiding it.
  108. “It was you!”
  109. > “No it wasn’t.” She laughed
  110. > Her eyes drifted across the room and her face was flushed
  111.  
  112.  
  113. > I think she was flirting with me
  114. > I swung my hoof towards her but instead of her leg my hoof met something large and squishy
  115. > “Ow! That was my boob.”
  116. “Sorry!”
  117. > Fluttershy reached under the table and started to rub her breast
  118. > I’m such a clutz
  119. “I’m so sorry! Are you okay?”
  120. > “It’s fine.”
  121. “Are you sure?”
  122. > Despite the pained look strewn across her face she nodded
  123. “It’s just my boob, I’ll be fine.”
  124.  
  125. > “Yeah…But They’re really nice boobs and I wouldn’t want to hurt them.”
  126. > Fluttershy’s ears perked up and she brought her hoof over a growing smile
  127. > “Thanks. I like yours too…Both pairs.”
  128. “I don’t. They get too heavy and hurt my neck and chest.”
  129. > “Well…Maybe we can go back to the Cottage and I can relieve some of that weight.”
  130.  
  131. > My nipples discharged like a firehose and the sound of the milk traveling through the tubes into the jars was audible.
  132. “T…That would be..nice.”
  133. > Fluttershy leaned in and started to circle the lip of my glass with her hoof.
  134.  
  135. > “You know…There are other ways we can relieve stress together…Maybe take off these tight dresses and lay under some blankets…”
  136. > “A..A..n..A..And..then what?”
  137. > “Well…What could we do under the blankets together?”
  138.  
  139. > I was becoming uncontrollably aroused
  140. > Flirting with your best friend is both exciting and really awkward
  141. > I don’t think friends are supposed to have sex and I was sure the tubes would explode from all this pressure.
  142.  
  143. > “Maybe…We could……Read a book together?”
  144. >...
  145. > “Sure…We could read a book. Thats exactly what I was thinking.”
  146. > She leaned back in her seat with her hooves at her side staring at the floor
  147. > My heart started to race
  148. > I’m such a ditz
  149.  
  150.  
  151. > "Or….Maybe we could…"
  152. > "Yes!?" She jumped
  153. > Have sex, buck, rub our privates together.
  154. "Never mind….Maybe we should…Give out some business cards.”
  155. > She sighed and replied in a soft, dejected voice
  156. > “Yeah…That's what we’re here for after all”
  157.  
  158. “Exactly!”
  159. >I grabbed her hoof and pulled her across the room
  160. > Thank Celestia I was out of THAT situation
  161. > Even when I’m being hit on I can’t get the nerve to reciprocate in a meaningful way
  162. > I’m never going to feel the pleasure of another ponies company
  163.  
  164.  
  165. > We walked through the party aimlessly
  166. > I didn’t have a plan on where we were going
  167. > I just wanted to distance myself from the intense frustration I was feeling circling the table
  168. > “There are a lot of ponies here I’ve never seen before.”
  169. > I stopped and examined the room mindfully
  170. > She was right, lots of unfamiliar ponies were here wearing expensive looking dresses and suits.
  171.  
  172. > These were the ponies I needed to sell Derpy Deliveries to.
  173. “Where should we start?”
  174. >Fluttershy pointed to a group of young affluent stallions leaning against a stack of tables.
  175. > “They look like investor types.”
  176.  
  177. > They stood next to a fence of tables and chairs that split the room in two
  178. > Beyond the tables and chairs were very well dressed ponies sitting around tables drinking wine and smoking.
  179. > I waved my hoof to get the attention of the stallions leaning against the table
  180.  
  181. > “Hell…Hello?…Hello!”
  182. > The stallions all turned looking annoyed that I interrupted them.
  183. "Ummm….Excuse me….Do you think you would be interested in….in…investing in a local business?”
  184. > They stared for a moment before exploding in laughter
  185.  
  186. > “Get a load of the tits on this one!”
  187. > “Ain’t those just the weirdest things you've ever seen!?”
  188.  
  189. > I closed my eyes and hung my head
  190. > I felt Fluttershy put her hoof on my shoulder
  191. > “You ponies are very mean. She was just trying be friendly.”
  192. > “Yeah, Well Whatever you’re selling we ain’t interested.”
  193.  
  194.  
  195.  
  196. > “What in Tartarus is going on over here?” a deep Canterlot accent rang
  197. > I looked up and saw Filthy Rich on the other side of the table with a frightening scowl
  198. > I was surprised to seem him because left town such a long time ago I had almost forgot what he looked like
  199. > The stallions coward like filly’s and sunk into their suits
  200. > “If you’re going to behave like frat ponies, I implore you to congregate with the locals.”
  201. > “Okay Mr. Rich.”
  202. > “Yeah…Sorry sir.”
  203.  
  204. > He looked over to us and his eyes widened.
  205. > His mouth hung agape as he shook his head
  206. > He closed his eyes for a quick moment before staring with his feverish blue eyes
  207. “Hi Mr. Rich! How are you?”
  208.  
  209. > “I must have had too much to drink.” He muttered
  210. > “Pretty weird isn’t she?”
  211. > Filthy Rich slapped the pony across the face
  212. > “Oh, Shut up you juvenile, trust fund foals.”
  213.  
  214. > He extended his hoof across the table
  215. > “Filthy Rich, at your service.”
  216. “Ummm....Derpy Hooves.”
  217. > He gripped me tightly in a firm hoofshake
  218. > “It’s a pleasure to meet you, please be my guest.”
  219.  
  220. > He shoved the table away creating a small crack that the we squeezed through.
  221. > It was so much different on this side of the room
  222. > Everpypony wore immaculate outfits and carried themselves in high esteem.
  223.  
  224. > Filthy Rich brought us to a round table at the far end of the room and poured us a some wine
  225. > Across from me sat a tangled maned mare with a salmon coat
  226. > She wore a mean grimace under a blanket of makeups that poorly covered the bags around her yawning eyes
  227. > She looked fed up
  228. > “This is my wife Spoiled Rich.”
  229.  
  230.  
  231. > I put my hoof out to shake hers but she didn’t move.
  232. “Hello…My name is Derpy Hooves.”
  233. > She took a calculated sip of her wine before placing it back on the table
  234. > “Your breath smells like a dead fish.” She grumbled
  235. “I’m sorry…I didn’t brush my teeth very well this morning…It's a funny story really! I was brushing my teeth and got distracted and dropped it..Then I…”
  236. > “Yet you still open your mouth. Are you really that oblivious?”
  237. > “I’m sorry…”
  238.  
  239. > I noticed her eyes locked onto my chest which that I promptly covered
  240. > “I wonder what my husband sees in you.”
  241. > Her tone screamed sarcasm
  242.  
  243. > Filthy Rich grabbed my wing and directed me to his side of the table.
  244. > “Don’t mind her.”
  245. > He pulled my hoof onto the table and coupled it
  246. > "Tell me more yourself, darling.”
  247. “I'm a Mailmare…Derpy Deliveries is our business. Have you heard of it?”
  248. > "I Can’t say I have. But please go on.”
  249.  
  250. >His hoof brushed up my leg in a slow tender rhythm
  251. > I couldn’t help but giggle, I’ve never been treated like a such a fancy mare before
  252. > And he was kind of handsome despite looking so much older
  253.  
  254. “Well…It’s a really good business. We work really hard to get your mail delivered on time.”
  255. > "That sounds marvellous.”
  256. > His voice fell into a whisper as he caressed my leg
  257. > “And I assume your husband helps?”
  258.  
  259. > "Oh I don't have a husband!” I laughed
  260. “It's just Fluttershy and I…she's my business partner and friend."
  261. > Fluttershy nodded then grabbed my free hoof and pulled it onto the table
  262. > “We’re really close friends.” Fluttershy said with a wide toothy smile
  263.  
  264. > Oh my gosh!
  265. > She’s touching my hoof!
  266. > And he’s touching my hoof!
  267. > This is amazing!
  268. > Filthy Rich grabbed the collar of my dress and rubbed the fabric
  269.  
  270. > "Judging by your glamor I can see you two are doing well."
  271. "We are….We're doing very well."
  272. > "And the model is so…Capitalist! I'm in total support of what you two are doing. Why should the state have a monopoly on the post office? I say let there be competition!" He laughed
  273. > What the heck was he talking about
  274. "Ummm….I guess?"
  275.  
  276. > He pulled his hoof away crumpling the folding the collar into a limp rag around my neck
  277. > "Unfortunately, I can’t be seen supporting such a radical concept. It’s bad for optics. But I think I could use a pony like you for my new business I’m starting here in town.”
  278. “What's the business?”
  279. > His eyes drifted across the room
  280. > “I would prefer to discuss details in a more private setting.”
  281. > Fluttershy’s grip tightened around my hoof
  282.  
  283. > “I’ll tell you this. I’m looking into acquiring a large patch of land near town. I have no doubt I’ll be able to claim it within the next couple days and we can begin business then. Are you interested?”
  284. “Sure! Sounds exciting sir!”
  285. > I don’t know if it was the excitement of male attention or Fluttershy’s sweaty hoof gripping my hoof.
  286. > But I was swimming in excitement.
  287. >My breasts were pumping at full cylinders and I was enamoured in powerful waves of warm, positive energy.
  288.  
  289.  
  290. > “Muffins…Maybe we should think about this…You don’t even know what you’re agreeing to.”
  291. > I took a couple deep breaths and tried to pretend I wasn’t spiralling
  292. “Sorry…I got a little excited.”
  293.  
  294. > Fluttershy adjusted my collar and poked the tip of my muzzle
  295. > “That's ok snuggle muffin.”
  296. > “Aren’t you two just the cutest couple.”
  297. > Fluttershy pulled her hoof away and started to blush
  298. > All that was running through my mind was four words:
  299. > penis, ponut, boobs, pussy
  300.  
  301. > I’ve never had two ponies flirting with me before
  302. > It was exciting
  303.  
  304. > “Oh….Ummm…Thanks…I don’t know if we would call ourselves a couple .”
  305. “Yeah!…We swing!” I divulged abruptly
  306.  
  307. > Fluttershy’s head snapped back towards me
  308. > “The fu…”
  309. > Mr. Rich put his hoofs over our lips leaned in close
  310. > “Listen. I'll let you two in on a little secret. "
  311. > We both nodded our head in unison
  312. > "This may disturb you considering the long standing cultural climate. But have you ever considered selling your breast milk? Because believe it or not there’s a large market for mare milk.”
  313.  
  314. > “Ummm….I never would have guessed.” Fluttershy replied
  315. > “I'm offering you a job Miss Hooves. I can guarantee you could easily make over 30,000 bits a year if you offer me a little bit of your time and all the milk your gorgeous breasts can produce.”
  316. > Fluttershy and I looked at each other nervously
  317.  
  318. > “It may sound crazy…Especially to small town ponies like yourselves but I guarantee this market is going to explode in the next couple of years.”
  319. > Mr. Rich grabbed my hoof from Fluttershy and kissed it
  320. > “And you, my four breasted beauty will be my princess.”
  321. > I looked over at his wife who was seething with a cigarette pressed between her lips
  322. “I don’t know sir…Isn’t that kind of…Illegal?”
  323. > “Very much so. But I don’t worry your pretty little head about such things. Just leave all that to me. Speaking truthfully Celestia pays little attention to this region. It's what we in business call economically insignificant.”
  324.  
  325. > 30,000 bits was more money I earned in three years working at the post
  326. > I would be able to get my house fixed and then some
  327.  
  328. > “Mr. Rich, you appreciate your offer but I don’t think my partner and I want to be involved in such things. We’re just two honest, hard working ponies who deliver mail.”
  329. “Fluttershy! That's a lot of bits!”
  330. > “We appreciate the offer but Derpy Deliveries is doing very well.”
  331. > I tried to pull my hoof from her grip but she held my hoof into the table
  332. > Mr. Rich was holding my other hoof and they were both pulling me in each direction.
  333. > "Miss Derpy I implore you to consider.”
  334.  
  335. >All this shaking was making my breasts rumble
  336. > Fluttershy tugged me hard and my bra snapped off.
  337. > My breasts fell onto the table with a loud WHAP!
  338. > The silverware jumped and our wine glasses toppled over
  339. > The tube snapped off my teats and milk poured from my breasts in streams all over the table.
  340.  
  341. > The table went quiet and everypony was starring
  342. “I'm so sorry sir!”
  343. > His eyes widened as he reached his hoof towards me
  344. > This was just like the post office all over again
  345. > I pulled my hooves under my lips and tried to fight back my tears
  346.  
  347. > He ran his hoof under my nipple and collected a bit sized drip of milk on the end.
  348. > His touch sent orgasmic shivers down my spin and I squirted milk at an even higher pressure
  349. > "May I?"
  350. "Ummm…Sure." I sniffled
  351.  
  352. > He brought the milk to his tongue and smiled.
  353. "This tastes wonderful! Very sweet but incredibly delicious."
  354. > I covered my nipples with my hooves but the milk just leaked around them
  355. > "T-thanks sir.
  356. > "You are quite the specimen, Miss Derpy….Maybe I could use your delivery services sometime, do you have a card?"
  357.  
  358. > Feeling relieved he didn’t hate me I reached into my pocket and gave him my card
  359. > “And where is your base of operations?”
  360. “Mostly my house, the address is on the card.”
  361.  
  362. > He shot me a smile
  363. > “Good to know.”
  364. > “Well, you better be off.”
  365. > He kissed my hoof again slowly
  366. > “Until next time, lovely.”
  367.  
  368.  
  369. > I fixed my bra and rushed outside to empty my jars
  370. > I kicked open the backdoor and began pouring
  371. “Fluttershy! What the heck!”
  372.  
  373. >“I’m sorry, I really am! I just don’t trust a pony like him.”
  374. > “You ruin it!”
  375. > I threw my dress at her and began emptying the jars into the grass.
  376. > “I don’t want you to be a milk mare. There's a reason I didn’t want you working for Milky. The job isn’t only dishonest but it’s dangerous and I don’t want to see you get hurt.”
  377.  
  378. “I’m a grown mare Fluttershy…I can make my own decisions.”
  379. > “It’s not just that. You're my…my..best friend and I only want what's best for you.”
  380. > “You don’t understand! You treat me like filly and I hate it!”
  381.  
  382. > Fluttershy slammed her hoof on the ground
  383. > “Muffins, listen to me. I’m one of the only ponies in town who doesn’t treat you any differently because of your conditions. When you lost your job I was there for you. I was the only pony that believed you could start Derpy Deliveries And I’ve been taking time out of my day for months helping run the backend of the company. Heck, I even wanted to name it Muffin’s Mail Services but you chose Derpy Deliveries because no pony even knows your real name! Which is a shame because you have a very nice name.”
  384.  
  385. “Fluttershy I need bits…I can’t keep living in a house where the ceiling is always falling on my head.”
  386. > “Then move in with me!”
  387. > “I told you I can’t do that!”
  388. > “Why not?”
  389. > “Because I don't want to!"
  390. >...
  391.  
  392. > Fluttershy sighed
  393. > “I know you better than any pony...Sometimes I think I know you better than you know yourself and you somehow manage to confuse me...I only do what I do because I care about you but if you don’t recognize that…Maybe this date is over.”
  394. >Fluttershy dropped the dress on in the grass and stormed inside
  395. “Fine!”
  396.  
  397. > I felt like hitting something.
  398. > I was so angry at her
  399. > I tossed one of the jars into the side of Sugar cube corner smashing the glass everywhere and leaving a dripping white stain on the wall.
  400. > Fluttershy made me feel ways I didn’t understand
  401. > I was furious that she ruined the deal with Filthy Rich but at the same time she was right
  402. > I was hopeless and she was the only pony with the patience to deal with me.
  403. > I hate how everything is so complicated now.
  404. > I don't wanna grow up

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