Nipplefuck High School: Ch. 01

Nipplefuck High School

Chapter 1: Revenge of the Nerd

*Note: Due to a complicated history of weird local politics and buildings acquisitions, Pezones Peaks Senior High School is attended by upperclassmen only, and all characters are eighteen years of age or older.*

Behind her locked bedroom door, a young woman bucked and writhed, supine on her bed. Her hands were between her legs, masturbating her pink pussy, while a thin black cord emerged from each of the large, puckered nipples of her quivering tits. The cords terminated at a pair of small egg shaped vibrators that had been inserted through her nipples, and were lodged entirely inside of her breasts. The soft lumps of youthful flesh jiggled wildly, agitated by the oscillating devices within. She watched a scene, a hentai anime, playing out on her tablet on the dresser, the audio going to her bluetooth earbuds.

On the screen, the beautiful and pure princess Momo had been taken captive, and was having her magnificent breasts ravished by two villains, Zargoth and Jawowo, who had jammed their monstrous, veiny cocks into her nipples, and were roughly pumping away into the pale, basketball-sized meat balloons. "You evildoers!" read the subtitles, as she screamed in Japanese. "You will never get away with this! My Roboknights will save me!"

"On the contrary, princess!" snorted Jawowo. "No one can help you now! You are doomed to be nipplefucked!"

Zargoth chuckled maliciously in agreement. "That's right, the Roboknights have been defeated, and now we are going to inseminate your royal breasts with our stinky evil cum! Ha ha ha!" Fountains of white milk sprayed from the business end of her tits as their members plowed away into their depths.

"Nooooo!" wailed the princess. "This cannot be! How dare you defile the purity of my precious boobs! My magical milk will be ruined and the kingdom will be lost! You must not cum in my nipples, no matter how good they feel!"

"I wish Zargoth and Jawowo would cum in my nipples," thought Charmaine, the girl on the bed, as she worked her clit, pussy juice pouring from her vagina and sweat beading on her pale skin. "I'd let them. I can hardly wait to get a real cock in there." The sensations inside her breasts were mounting, she was almost there.

"Ho ho, too late!" shouted Zargoth. "Prepare your defenseless mammary glands for our seed!" They both rammed brutally into her wobbling mountains of soft flesh, and a wet sloshing sound interrupted the princess's screams. "AAAAAA! You're so cruel! You came in my tits! she cried, as impossible geysers of milk and semen spewed from her stuffed nipples. "Ahhhhhhh!! I'm coming too! My boobs are coming!! Forgive me, I am a nipplewhore!"

Charmaine came too, stifling her moans and cries so her family would not hear. Her slightly chubby body shivered and convulsed in climax, over and over, gradually becoming still but for her chest heaving from her breath, and the meaty little sacks on her chest flopping in tow. Catching her breath, she switched off the vibrators and pulled on the cords. Her big nipples began to dilate and spread as the egg shaped vibrators began to pass through. They emerged from her titholes, and her nipples spit out the toys with a wet plorp, remaining dilated enough for the pretty pink lining of her teat canal to show briefly, until the nipples closed up once more.

Charmaine sat up, already wearing the big, thick rimmed, coke-bottle glasses that she needed to see, and looked at herself in the mirror, her mousey brown hair disheveled. She smiled at herself, showing the braces she still wore. A few more zits today, she noticed, her smile turning into a frown. She examined her breasts, hefting them in her hands. She enjoyed what she did with them, but she was self conscious and she thought they were weird. They were not like the huge, tumescent orbs of the anime princess. They weren't even like most other girls' tits. They were about the size of large grapefruit, but more extended -- maybe more like acorn squash. A physician might describe them as "tuberous" -- elongated rather than round, like a pair of bombs, hanging slightly despite her youth. Her areolas were large and dusky pink, covering the entire end of each breast like a succulent slice of bologna. Her nipples were also big -- broad, meaty knobs with a cratered orifice at the center leading inside, now a bit more open than usual, after accommodating the vibrators.

She had known they were abnormal for some time. When she first began to masturbate, she experimented with poking small objects - hairpins and such - inside. When this was successful, she worked up to pens, and eventually her own fingers, delving ever deeper into her chest in pursuit of sexual gratification. Then, after seeing nipple penetration in hentai anime, she knew that was what her tits were made for, and she began experimenting with more daring insertions -- small dildos and vibrators purchased from online. It was painful getting them inside at first, but the pleasure from penetrating her own breasts was exquisite. Sometimes she would pour warm milk inside and watch as she squeezed it out. Of course, her virginal breasts had never produced more than a few scant drops of their own milk, her insides moistened only by thin clear secretions, so anything she put inside needed plenty of lubrication.

The clerks at the pharmacy never batted an eye at her buying lube. Eventually, doing some research on the internet, she discovered that, though rare, more and more women were spontaneously developing breasts along a more typically bovine pattern -- a single larger teat canal in each nipple leading to a cistern fed by the ducts, rather than the many individual ducts terminating in the nipple. Scientists were not in agreement why, but many thought that it may be due to hormones in food, or agricultural chemicals in the water supply. She was obviously one of these women. She had never had a boyfriend, and never had a real penis in any of her holes. She was a complete virgin. She was saving her cunt for someone special, but sex in the nipples didn't count, right? Charmaine wanted so badly to get her tits railed by real flesh and blood men.

The next morning at Pezones Peaks High School, Charmaine was rinsing the sweat from her unathletic frame in the shower after gym class. She had acquitted herself poorly in the volleyball game, as she did at most sporting endeavors.

Two of the cheerleaders, Makayla and Kaylee, were looking derisively at Charmaine and snickering. They were both stereotypically gorgeous in different ways, looking like ideal statues of fit young beauty as the water poured over them. Makayla was blonde, curvy, and busty, her firm, round breasts tipped with perky pink nipples. Kaylee was black haired, lithe, and slim, her A-cup breasts bearing a pair of puffy brown teats. Neither of them had the conspicuous inverted pores of Charmaine's nipples.

"Oh my god, Makayla," sneered Kaylee. "It's the nerd. Look at the nerd's weird tits."

"Like, barf me out," replied Makayla. "Theyre not even that big but they're, like, already saggy. And her areolas cover, like, the whole end. Gross."

Charmaine dropped her gaze to the tile floor and covered her breasts with her hands. "And what is wrong with her nipples? They're like weird boobie buttholes. Eeew."

"That's, like, so gross. If I had tits like that, I'd soooo kill myself." Charmaine, her face red from more than just the hot water, left the shower, toweled off, and got out of the locker room as quickly as she could.

Humiliated for the last time, Charmaine formulated a plan. It's rare for a boys' football team to have a female coach, but the coach at Pezones Peaks High School was the formidable Marsha Hills, who could be described as a tall, muscular Superbimbo with a gigantic chest, like a pair of swollen watermelons.

Coach Hills was the subject of many rumors among the students. One of these stated that she was a war veteran, a commando who had suffered extreme boob damage in a firefight behind enemy lines in Bananastan. She opted to have her tits not only reconstructed, but rebuilt into huge globular gazongas. The addendum to that rumor was that, when Coach Hills had her breasts augmented, she had her nipples surgically altered into sex organs, like breast vaginas with the healed remnants of her own mammary system plumbed into them for her milk to serve as lubrication.

The other addendum to the rumor was that she motivated the team to perform at their best by allowing the two best players each season to each have their way with one of her tits. Of course, this would be super illegal, but this one of the most consistently winning teams in the state, and the team brought in enough money to the school for people to maybe look the other way. Boys will be boys, of course. Two of those boys just happened to be Troy and Chad, the star QB and runningback on the football team. They also happened to be Makayla and Kaylee's boyfriends. If what people said was true, they'd been thinking about it, and would probably be eager to get some nipplefucking practice in before the big game. Yes, Charmaine was going to have her revenge on those bitches and finally get her nipple cherries popped at the same time.

Charmaine slipped notes into Troy and Chad's lockers, purporting to be from their girlfriends, instructing them to meet in the boiler room with the broken door lock after school for some hot sex. The lock was broken because Charmaine was going to break it. The handwriting probably did not match that of the girls', but Charmaine was betting that the jocks would be too dumb and horny to notice.

After school, surrounded by the ambient hum of machinery, Charmaine waited in the dim room, seated in a folding chair she found. She wore her Kmart brand jeans and a gray hoodie sweatshirt with nothing underneath. A bottle of lube sat on the floor next to her, and light from the single old incandescent bulb reflected off her glasses. Would they show up? She hoped so. She had been waiting so long to finally really get fucked in the tits like the cartoon sluts from the internet. Troy and Chad might be dumb jerks, but they were hot studs, and she shivered in eager anticipation of them shoving their dicks up her virgin tit spigots and scrambling the insides of her breasts to orgasm, and of their sperm flooding her ducts. She had set up a digital video camera to capture the whole thing, because she was going to make a movie just for Makayla and Kaylee. While she waited anxiously and enthusiastically, she did her best to summon her inner slut. This was all new to her.

At long last, the door swung open and a tall young man, Chad, came in, his long curly hair swinging as he looked cautiously around. "Where's Kaylee?" he inquired.

"Kaylee's not here," said Charmaine, "but I am. Do you know who I am?"

"You're, uh, Sherise?"

"Charmaine."

"Oh. Yeah. What's going on, Charmaine? Where's Kaylee?"

Just then, Troy, a shorter, broader, clean cut guy, walked in the door.

"Just in time," Charmaine said.

Troy looked around and saw his friend. "Who's this? Where's Makayla? What are you doing here dude?!"

"I don't know," said Chad in confusion. "She says she's Charmaine."

"Boys," interjected Charmaine, "I brought both of you here, the notes were from me. I have something to show you." She unzipped her hoodie in front, shrugged it from her arms, and sat there naked from the waist up. It was showtime. She thrust out her chest towards the boys and shook her plump, droopy, tubular tits at them, hefting them to show the boys her giant areolas and penetrable teats. Trickles of clear, thick fluid dripped from Charmaine's puckered holes and ran down her soft naked belly -- she had prepared by squirting as much lube into her breasts as she could. Her gland cisterns were packed full of ky jelly, to ease the intrusion of her first real cocks.

"Some people told me these boobs are weird and gross, but I want to know what you think. I bet you think they're hot. There aren't a lot of fuckable milkholes in the world, but there's two of them right here if you want them. You're Pezones Peaks football players, so I know you have been dreaming of nipple fucking. You won't be able to get balls deep in me like I assume you could in coach, but you could wait around all season and find out if you're good enough for her, or you could fuck my nipples right now. I might be a nerd, but I have two hungry cock sockets in my chest, and I'm offering them to you!" She shoved her index fingers inside to prove a point, making a lewd face and running her tongue over her braces-festooned teeth, then withdrew them and spread the openings as wide as she could, showing off the inviting pink titty tunnels, oozing lube. "You want these slutty nipples or not? They're all yours."

Troy and Chad, dumbfounded, looked at her, then at one another, then back to her. "Come and fuck em, boys!" The football players, as if under a spell, unzipped and unbuttoned the flies of their trousers and pulled their genitals out through the flies of their boxer shorts, the cocks already beginning to fill out with arousal. They strode over to the seated, topless girl. Charmaine grinned and slathered the young mens' rising penises with lube, then jerked them both to full erection.

When they were hard enough, she guided the meat seeking missiles to their intended targets, and rubbed the swollen tips on her lube leaking nipples. "You first," she ordered Troy. He pressed forward into her hand-held breast, and she grimaced in a mixture of pain and pleasure as Troy's thick cock head, leaking precum, parted the taut sphincter of her nipple and gradually slipped inside her lewd lubed boob tube. She instructed Troy to hold still while she got Chad inside of her. Chad's bulbous glans pressed into her right teat, and the orifice slowly stretched to swallow it. He popped inside, a look of dumb amazement on his face, and excited hunger on hers.

With both studs inserted into her aroused dairy nozzles, she held her breasts in her hands to keep them steady and gave the command: "Start fucking. Please go slow at first." They tentatively began to move their cocks inside her jiggly boobie bulbs, violating the tender orifices that nature never intended to be penetrated. They slowly moved in and out, exploring the flesh sockets and reveling in the novelty. Charmaine's tits radiated a mixture of discomfort and strange, intense carnal pleasure throughout her body, echoing in her loosening, juicening virgin cunt.

"I can't believe we're really fucking your nipples!" Chad exclaimed. "This is fucking crazy!" They gradually picked up the pace, her hands gripping her vulnerable glands to stabilize them so the meatrods could slide in and out of the limited cavities within. As their arousal intensified, their lust for the nerd's warm, fat titflesh took over and they abandoned moderation, and soon, two hard athletic cocks plunged unsparingly back and forth in her tight young teat canals. They could only penetrate a few inches into her inexperienced boobs before filling her shallow breast cisterns completely, but it was enough for intercourse.

The cocks pummeled her "back walls" with every thrust, churning her sensitive mammary tissue as they reached a dead end where her young ducts could not admit them any further. It was painful for her virgin holes, put the pain was equalled, and indeed exceeded, by the pleasure and excitement -- she was a real life nipple slut now, and she loved it!

Her dream was coming true -- a pair of pumping penises were using her ripe little chest receptacles like onaholes, filling them thoroughly, churning the sensitive tissue, and she was making them go crazy for the nerd body they had overlooked before. Breathing heavily, she egged the boys on: "Don't hold back! Fuck these titties! Jam it in there and stretch out my ducts! My nipples are hot pussies for you! You better not disappoint them! Fuck my udders and tell me I'm a hot little cow!" Charmaine, who had never been with a man before, didn't know where she was finding these dirty words. It was like the dicks had found and flipped some switch inside her tits that turned her from a shy nerd to a raging nymphomaniac.

"Uhh... you're a hot cow!" said Troy. The declaration unexpectedly hit Charmaine right in her slut switch again, the words inflaming her tits with passion. Charmaine was not like Princess Momo: she was loving every minute of this and she couldn't wait for her penetrators to ejaculate into her breasts. She wondered what it was going to feel like. She felt like such a twisted little whore, taking it in the tits.

"Boobfuck me! Harder! Rail these slutty little stretched out nipples like tight cunts! Yes! Make me cum in my titties and then fill my milk glands with jizz!" Charmaine squealed and bucked, her hands squeezing her quivering, cock-stuffed fucksacks as the pumping pistons in her milkpipes pushed her over the edge to orgasm. She felt a new sensation as Troy's cock twitched and a pulsing torrent of his testicular juices surged deep into her mammary tract. "Ohhh!" She moaned as they climaxed together. His sperm filled her breast cistern and pumped onwards into the depths of her boob, far into the many branching, narrow ducts where his cock could not penetrate, seeping into the crevices and glandular tissue deep inside her, and spilling out in a dirty flood around the place where his cock and her teat met.

The passionate spasms of Charmaine's slippery, orgasming duct were enough to make Chad finish as well, and she yelped as he slammed deep into her breast, smashing the delicate tissue against her chest wall, and injected the recesses of her mammary gland with his own load of hot penis cream. The three stood still together for a moment, breathing hard, and then the boys withdrew, leaving her well-used nipples gaped, two dilated pink portals into her chest, dripping with sperm and lube. She looked down at her sore, pillaged teat openings, the echoes of her orgasm still thrilling her, and marveled at what she had done.

"I guess the real MVP wide receivers... are my tits." said Charmaine. She had thought that one up earlier and was proud of it.

"No, that's Brad and Tony." said Chad.

She faced the camera, making sure to give the cheerleaders a good view of their boyfriends' loads oozing out of her dilated nipples and dripping down her chest and slightly chubby belly. She made the most whorish face she could muster up and, taking her swollen, torpedo-shaped breasts in her hands, squeezed them, wringing them out into two floods of pearlescent cum that ran down her torso, white-hot lava flows from erupting twin meat volcanoes. "Let me know if you want me to breastfeed you!" she said to the camera.

"No way!" said Troy. "That's gay! Gross!"

"Yeah!" agreed Chad.

"I'm not talking to you," said Charmaine.

"Then who are you talking to?" asked Chad.

"You'll find out." And she sent the jocks on their way, pleased with themselves... after slipping them her phone number.

Charmaine felt great. She was mildly disturbed at herself, but she could not deny how much she had enjoyed getting nipplefucked for real. Her tits were sore but satisfied, still running with lube and cum. And her jeans, soaked at the crotch, were still on -- she was still technically a virgin! She walked home, the semen still oozing from her teats under her hoodie, although they were beginning to regain their tone and close back up. She walked into her house, greeting her unsuspecting family as tersely as possible, and went immediately upstairs to shower off, hosing out her red, dilated, pleasantly aching boobholes as best she could, as she reflected on the day's success in a cloud of steam.

Later that evening, she uploaded the video to her tablet, did a rough edit, and attached it to an email addressed to Makayla and Kaylee, so they could watch their boyfriends enjoying the breasts they had mocked so thoughtlessly. With a smug smirk, she hit "send" and went to bed, falling into dreams of having her mammary glands plowed by hentai tentacles that insinuated their way deep inside her thorax. They were not nightmares.