DISCLAIMER: This is a work of fan fiction borrowing characters from the Pokémon universe, which is trademarked by The Pokémon Company. I do not claim ownership over any of the characters or settings and make no money from publishing this story.
WARNING: This work of fiction is Rated MA and only suitable for mature audiences. It may contain explicit language, adult themes and graphic descriptions of a violent and/or sexual nature.
May’s Valentine’s Surprise
Chapter 2 – DinaB
Ash broke through the surface of the water and slicked back his damp hair. The pool ignited boisterous screams and splashes behind him. He wiped his eyes clear to find a pair of feet flanking him on the tanning ledge. Following the long, slender legs attached to them, he met the familiar face of a brunette wearing her hair in long pig-tails. Her bikini-clad frame blocked the sun as she waved down at him with a friendly smile.
“Hey, there. Rosa, right?” He used his right hand as a visor to try and get a better look. “One of May’s friends?”
“Yip! And you’re Ash Ketchum. From Pallet Town!”
He laughed uneasily. Did he really sound that juvenile whenever he’d introduced himself? “Um, yeah, that’s me.”
“Of course it is! Who doesn’t know Ash Ketchum from Pallet Town?!”
Oh, brother. Here we go again. Girls like Rosa made him crave the days he was just another faceless Trainer on the road chasing their dreams. Not that he didn’t appreciate all his accolades and the stardom that came with defeating Alola’s Champion; he just wanted to take a break from being himself sometimes, from being what everyone pictured him to be when they saw him on TV. He’d developed a new respect for Gary Oak after watching him shepherd a myriad of fangirls everywhere he went from day one.
Ash did well to mask the discomfort from being recognised but something on his face must’ve given Rosa the impression she’d annoyed him.
“Er, I don’t mean to bother you or anything!” She fretted and waved her hands in a panic. “It’s just, well, I kind of thought, well, I wanted to talk to you about something important. That’s all.”
“Yeah.” She bent down and whispered, “It’s about May.”
“May?” Now that piqued his interest. “Is she in some kind of trouble?” He glanced around but couldn’t spot May’s face amongst the kids splashing in the pool or chilling on the sidelines. Come to think of it, he couldn’t see the other girl Rosa had been with either. “Where’d your friends go anyway?”
“Oh, who knows? They’re probably fannying about in this resort somewhere.”
“Ah…” Her blasé attitude calmed his fears of the worse. But if May wasn’t in trouble, what was so important? “Everything okay then?”
“Errrm… not exactly.”
Ash climbed out of the pool and sat on the tanning ledge. “What’s going on?” He patted the space next to him. “Sit down. Tell me all about it.”
“Oh, okay. Don’t mind if I do!” She plopped down and scissored her legs in the water playfully. It seemed as though she was so happy to be sitting next to Ash Ketchum, she’d forgotten there was something she wanted to tell him.
“So… you were saying?” Ash nudged at her memory. “There’s ‘something important’ going on?”
“Oh, right! It’s about May.”
“What about May?”
“Well, hmmm.” She contorted her features in deep consideration. “On second thought, maybe I should keep my trap shut! I’m not sure I should even be telling you this… like, it’s probably not my place. But then if I don’t, who will? May definitely won’t! That’s for sure. And then nothing will change. The day will go to waste! And that would suck because… you should definitely know. You need to know!” Rosa sighed and pulled at her pigtails. “Euurgh! What do I do?!”
“First of all, you should calm down.” Ash let slip an uneasy laugh. Melodrama never helped any situation. Ash was of two minds; he wanted to know more than ever what got her so worked up, but he also felt it would be wrong to play a part in someone talking behind their friend’s back. Besides, if May wanted him to know something, there was nothing stopping her from telling him herself. “You’re obviously way invested in this but it wouldn’t feel right if you just came out and told me –”
“May has a huge crush on you!”
Rosa slapped both hands over her mouth far too late to stop the runaway admission.
Ash blinked. “What?” It couldn’t be. And yet, the pink escaping from under the girl’s smothered cheeks was the perfect shade of legitimate shame and instant regret. But that would mean… May actually liked him?
Ash thought back to when Pikachu accidentally fried her bike, how she’d so whimsically dismissed it, then joined him on a trip spanning across the whole of Hoenn, even though she knew very little about pokémon, even though they’d frightened her shitless. Should he have taken that as a sign? How could he have known? They’d faced rivals and Team Rocket and Team Magma together, blundered over old, rickety bridges that collapsed the moment their feet touched the other side, survived caves infested with ghost pokémon that wanted to eat their eyeballs, and through all the rain and sandstorms and crippling pain and death they’d narrowly escaped time and time again, she’d never once found the courage to tell him she liked him?
And, stranger still, he’d never noticed?
Ash felt like that was something he would’ve picked up on for sure. Granted, numerous acquaintances he’d met on numerous adventures told him numerous times he was ‘so clueless when it came to women’. May, herself, might’ve uttered those exact words. In retrospect, his detractors might’ve had a point…
For the longest time, Ash had operated in tunnel vision, with ‘Pokémon Mastery’ the only light growing ahead of him. Romance was just another distraction that sank into the peripheral darkness. Looking back now, he wouldn’t have noticed even if he’d wanted to.
“Yeah.” Rosa spoke through her hands and gave him a slow nod. “So…”
“Aren’t you going to say anything?”
“Um… are you sure?” Ash said, for no other reason than not knowing what to say. Of course Rosa was sure! She wouldn’t be risking her friendship based off of ill-informed gossip?
“Full disclosure…” Rosa lowered her hands far enough for her soft-spoken words to be heard unobstructed. “Hilda and I are pretty sure you’re the only reason we’re here. May’s been hoping to run into you. Looks like the poor girl’s lost her nerve though. She just doesn’t know what to say or how to even start saying it.” Rosa’s eyes dimmed with hopelessness.
Ash was still stuck on ‘May’s got a huge crush on you!’ She didn’t just like him – it was a huge crush? Dang, even when they’d embraced earlier, he was none the wiser. And here he thought he’d expanded his tunnel vision over the years.
Why was Rosa telling him all this though? And now? What did she expect him to do about it?
“Sorry,” she said abruptly. “I shouldn’t have said anything, huh? I’m a horrible friend, aren’t I?”
“Why did you?” Ash asked. “Tell me all this?”
“I dunno… I thought, maybe, today being Valentine’s and all…” Prodding the tips of her index fingers together distracted Rosa from her coyness. “I mean, you and May seem to get along great so I thought… maybe… there’s a chance you two might… I dunno…”
Ash saw where this was going. What made her so sure he wasn’t seeing someone already? Sure, coming to a Valentines-themed resort with only a couple of male friends might’ve been a clue, but she couldn’t know for certain. Yet here she was trying to get him to ask her friend out. The idea didn’t repulse him, but… “Me and May?”
“Yeah! Well, assuming you also might… like her, or something?”
“Uh, yeah. I like May.” Then he quickly added, “As a friend, I mean!” He’d never entertained a thought beyond their friendship. Not because she wasn’t really attractive or really amazing or someone worth dating, but because… hrm, why hadn’t he ever thought about asking her out?
“Okay, I get it.” Rosa scratched the back of her head, embarrassed for even trying. “This was a mistake.” She gave a sheepish laugh then stood up. “Erm, please could we forget this ever happened? And if you run into May, promise me you won’t tell her anything I’ve said?”
Oh, gee. He hadn’t meant to make her feel bad for trying to help a friend out. She probably shouldn’t have spilt May’s ‘secret’ but Ash was not without sympathy for her predicament. Valentine’s Day brought out the hopeless romantic in a lot of people his age, it seemed. He could forgive her for overstepping and nodded his acceptance to keep their little discussion between them. With that, she wrapped a towel around herself and headed back into the resort.
Ash sat there alone swimming in his thoughts. Thoughts which drowned out the noise and commotion splashing in the packed pool. Rosa had given him more to mull over than she’d realised. While his vacant expression dawdled on a group of boys wrestling each other into the water from atop their friends’ shoulders, a sudden voice started his right ear.
“Hey, you’re Ash Ketchum, right?”
The aforementioned Trainer looked up to see three tall, modelesque beauties standing over his shoulder, clad in red swimsuits that reminded him of the sexy lifeguards he’d seen on TV shows growing up. Despite their devastatingly good looks, he couldn’t muster more than a forced, “yeah?”
If his name weren’t Ash Ketchum, they wouldn’t have given him a second glance, let alone stopped to bombard him with plastic smiles and flattering proclamations. A reluctant Ash posed for their photos but declined an invite to their private suite after-party later this evening. Rooting for him in televised competitions didn’t make them friends, or even people he could trust. They walked away wearing sour expressions.
Two heads surfaced from the pool on either side of him. “Dude,” Nate said, “did you seriously turn away those hot broads?”
Hilbert stared down the poolside stealing every glimpse of the departed trio he possibly could. “What a missed opportunity! Sure you’re feeling okay, Ash?”
“It’s called ‘leading with your head’,” Ash said. “You should try it sometime.”
“What are you talking about? I do that all the time.”
“Er, I think he’s talking about the head on your shoulders,” Nate said.
Ash facepalmed. These two had influenced at least two-thirds of the bad decisions he’d made in the last couple of months. Would they ever tire leaping from one after-party to the next? From one vapid fangirl to another? For Ash, the celebratory tour had run its course. He was ready for his next challenge. To his surprise, the prospect of another region hadn’t jumped to the forefront of his mind.
This Valentine’s bug going around must’ve bitten him, too.
Maybe it was a little more than that. What someone like May offered out of the box was built-in trust. He didn’t need to question the authenticity of her interest, the genuineness in her compliments. Oddly enough, the ladder to success seemed to get lonelier the higher up he climbed, something he’d never anticipated. It would’ve been nice to have someone around that had his back again, someone that wasn’t in it for selfie moments, or free access to loose fangirls.
Ash stood and stretched his arms out under the sun. “I need to take a leak.”
“So did I,” Nate said, “two minutes ago.”
The unashamed urinator shrugged. “Bet you everyone here’s done it.” He pushed away from pool’s wall and eased into a blasé backstroke.
“And that’s supposed to make me feel better?” Ash scratched his head.
Hilbert thrusted a palm of water at the delinquent. “Forget him! If you see those girls on your way to the bathroom, don’t forget to tell them where they can find us. It’s cool if you’re not feeling up to it today. Me and Nate will share the third one.” He wiggled his eyebrows suggestively.
“Right…” Ash watched Pikachu entertaining a group of happy-go-lucky children playing a makeshift game of water polo at one end of the pool. Kids really loved Pikachu and Ash didn’t have the heart to take their smiles from them. Besides, this was an adventure he’d be fine completing on his own. “Be right back. Keep an eye on Pikachu, will ya?”
“You got it, buddy.” Hilbert saluted him.
Ash approached the reception desk racking his brain for the right words. The lady at the counter hadn’t the etiquette to get rid of her chewing gum before mumbling a grumpy hello. Clearly, she was over this whole Valentine’s gig. Her lack of professionalism threw him off guard. His face went blank trying to remember what he’d practiced. He gave up and opted for the direct approach. “Hello, I’m looking for someone. Could you help me find their room number, please?” He provided May’s full name.
“Sorry, no can do,” she said, out the side of her mouth not rolling gum. “Even if I wanted to, it’s against our policy. I could get in a lot of doo-doo and I don’t need this day getting any worse than it’s already been.”
“Yeah, of course, I get it.” Ash rubbed the back of his head sheepishly. Damnit, why couldn’t he be better at lying? Just as he turned back to leave, she piped up again.
“Say, you wouldn’t happen to be that Ash Ketchum kid, would ya?”
“Uh, yeah, that’s me.”
“Thought so! Did kind of look familiar. Hey, tell you what…” She lowered her voice and beckoned him to lean in. “My daughter’s a huge fan, wants to grow up to become a Pokémon Trainer just like you. The whole pokémon battling thing is not my speed but I know she’d appreciate a little token of your generosity. Scribble a lil’ something down with it and maybe I can scribble a lil’ something down for you, too. Get my drift?”
Ah. The proverbial favour for a favour. This might be the first time his celebrity got him anything worthwhile. “Just tell me where to sign.”
Ash wandered through the resort’s corridors comparing the room numbers to the digits scribbled on the back of a throwaway business card. Trepidation swelled in his chest as he came across the matching door. Supposedly, May was stood on the other side, just as nervous as him to initiate the long-overdue conversation. He paced outside her room putting together the perfect words to broach the topic.
This is crazy! It’s only May.
He’d only spoken to her a billion times before. All he had to do was go in there and have his mouth start moving. Sure, they’d be met with awkwardness at first but, if anything Rosa said was accurate, May would be more than willing to hear him out. She knew him to be genuine and he longed for authenticity more than anything else right now. His appearance at her doorstep might come as a surprise but, perhaps, the biggest surprise was they hadn’t gotten together sooner.
Ash knocked on the door.
The response was immediate: the sound of hasty shuffling on the other side. Then utter silence, as though the occupant was listening to confirm the knock had risen from her door. Ash obliged with another rap of his knuckles. “Hello? You in there, May?”
“Who is it?”
She gasped in panic. Not the reaction he’d expected. And even more curious, Ash heard a second hushed voice through the door, “Oh my God, it’s him!” And a third, “What should we do?!”
He pressed his ear on the door and eavesdropped on the trio debating in low mutters whether or not to open for him. One of the voices sounded like the girl he’d spoken to at poolside and the other, he imagined, belonged to their mutual friend – Hilda, was it? If Ash had known May was entertaining company, he would’ve waited for her back at the pool. “Er, sorry,” he said in a loud, shaky voice. “If it’s a bad time, I can come back lat-”
“No!” someone blared. “You stay right where you are, Ketchum!”
“Hilda?!” May whispered hotly, uncertainly. “What are you doing?”
“Sorry, May,” she whispered back, “but someone has to drag you out of the closet!”
Huh? Ash quirked an eyebrow. What was that supposed to mean? And nobody had to drag anybody anywhere. Still, curiosity overrode his better judgement and he continued to listen without interference.
“What better time than now?” Rosa chipped in with a soft murmur. “What better day than today? I mean, it is Valentine’s after all! Plus, I might’ve already spoken to him about you at the pool…”
“You did what?!” May exclaimed in an uncharacteristically deep and threatening voice. “I know you guys are only trying to help –”
“Then let us,” Hilda cut her off.
Wow. And Ash thought he’d had pushy friends. One of the girls shouted “just a minute!” before he heard the hustle and bustle of footsteps trotting about the room. Were they tidying up or something? They’d quietened their whispers to indistinguishable murmurs, leaving the eavesdropper guessing as to their frantic activities. Ash heard everything from zippers to drawers opening and shutting to furniture being shifted around to cardboard being cut? All this kerfuffle because of him? He shouldered some regret for whatever May’s friends were putting her through.
Just as he contemplated walking away to spare her their doggedness, the door flew open and a hand dragged him in by the wrist. “Whoa!”
. . .
Ash found himself standing topless in May’s room as Hilda shut the door behind him. It only occurred to him then, he might’ve wanted to put on a shirt before prowling in the resort for May. Not that he looked bad in swimming trunks; his dotted abdomen was flat as faint lines drew an arrow to his blue waistband. Somehow though, he felt grossly underdressed being the sole male in a room occupied by three females.
Hilda rounded back to Rosa’s side and the two best friends stood in front of him like bodyguards protecting May, only glimpses of her red bandana visible behind the blockade of their shoulders.
Ash didn’t get it. Why were they acting like she needed protection from him? “What’s going on here?”
“Our friend,” Hilda said, “May, has something she’d really like to tell you.”
“Well, show you,” Rosa corrected. “A gift.”
“A gift?” Ash mused. She’d gotten him something for Valentine’s?
“It’s not gonna be a diamond ring.” Rosa wagged her finger.
“Nope,” Hilda concurred. “That sort of gift don’t mean anything.”
“A guy like you needs something real.”
“Something from the heart. Something special.”
May stood in silence behind her friends as they serenaded him with this idea of her amazing gift. Ash didn’t have the patience to try to guess. “Well? What is it?”
Hilda and Rosa nodded at each other then slid to either side, revealing May stood in her familiar attire, holding a crimson wrapped gift box garnished with a gold ribbon. Aw, she shouldn’t have. Without lifting the box she held at her waist, May raised her bashful head and instructed Ash in a timid voice. “Take off the top. And take a look inside.”
Shucks. Maybe he should’ve gotten her something, too. He would definitely have to after this.
With bated breath, Ash followed her instructions and lifted the lid off the gift box. He took a look inside and his mouth fell open, his eyes nearly bulging out of their sockets. “Is that… that… is that a –”
“Dick in a box!” Hilda and Rosa shouted in chorus with the same spirit you would’ve shouted ‘surprise!’ at a surprise birthday party.
But instead of confetti showering him from the ceiling, his own thoughts were disjointed and thrown up in the air, and the only guest that had sprung out unexpectedly was the smooth-looking, semi-erect phallus slumped through a hole cut out the side of her gift box. Ash did a doubletake and only just noticed May’s infamous bike shorts were missing from her ensemble, further suggesting the dick in the box did indeed belong to her.
May cast her eyes down, unable to endure his gobsmacked expression. “I’m… sorry, Ash. I should’ve told you sooner.”
“No, no, no!” Hilda stepped in like a director waving at her actors to cut the scene. “We’ve already been through this, May. You don’t need to apologise for anything.”
“I know but –”
“It’s who you are.” Rosa stood by her side. “And if Ash can’t accept you for who you are, for all of who you are, then he doesn’t deserve you.” She squeezed May’s shoulder before turning to the man of the hour. “So, do you, Ash? Accept May for who she is?”
Ash was still picking his jaw off the floor when the question struck him. Of course he accepted May for who she was; what kind of friend would he be if he didn’t? However, he couldn’t pretend not to notice the surprise she’d sprung on him like a phallic jack-in-a-box. So many questions. The one that had him scratching his head the most was probably how he’d failed to notice till now?
Granted, he hadn’t spent an inordinate amount of time looking in that area and, even if he had, May often kept it veiled under one article of clothing or another. The way she coyly slipped the lid back on the box hinted at her continued discomfort with people knowing her secret or, at the very least, people seeing it. In that fleeting gesture alone, Ash came to sympathise with how complicated her life must’ve been.
He didn’t know whether to thank her friends for attempting to help May overcome her insecurities, or lambast them for the crude and flippant manner in which they’d attempted to do it. ‘A dick in a box!’ Really?
For all his criticisms, Ash himself hadn’t found the right words to address Rosa’s concerns. Yes, he liked May. But he also liked pussy. Dick? Not so much. Could he still picture a romantic future with May? Just when he’d thought he answered that question, this meaty surprise complicated matters quite a lot. “I… I…”
“You what?” Hilda snapped. She sounded unimpressed by how long they’d been waiting for his answer. “It’s not a difficult question.”
“It’s a lot to take in…”
May slumped her shoulders. It looked as though all the air had been stolen from her lungs. “Yeah. I get it…”
Hilda made a sudden move towards Ash. He didn’t get to see what she’d intended as Rosa seized her by the arm before she got too far. “It’s okay,” said the calmer girl. “We should give him a chance to think about it at least.”
“Tch.” Hilda shrugged her arm away, though she didn’t disagree.
“One thing May knows for sure is we’ll always have her back.” Rosa rubbed said back reassuringly.
Hilda curled her lips into a sly smirk. “And her front.” She tugged the box away from May and the girl’s penis lolled out of the makeshift hole. Ash watched, awestruck, as the unexpected member dangled from the bottom of her little, white skirt. May appeared to make a move to cover up but Hilda got there first. “Now, where were we?” She began jerking May’s cock right in front of him.
Ash lost the ability to speak, barely trusted his own eyes. The girls hadn’t gifted him half a minute to digest the fact May had a cock before they took turns stroking it to full stiffness. Just what had he stepped into?
And holy shit – May has a cock!
Right out of the box and into Hilda’s ravenous mouth. The girl in little jean shorts was all too happy to get on her knees and take May into her throat. While her dick enjoyed a wet and sloppy tongue massage, her hardened nipples squealed from the twists and turns Rosa applied over her shirt. Objectified, right before her crush’s eyes, her face turned the same shade as her bandana. In spite of it all, May said and did nothing to dissuade her friends from enjoying her unique body, nor to dissuade him from watching.
Ash got the message loud and clear: May was quite the catch and, should he turn her down, she’d have more than her fair share of suitors lining up to appreciate her hidden treasures.
And appreciate they did; Hilda, in particular, slurping and moaning on the taste of May’s Penis Surprise. Rosa soon kneeled, too, lured south by the sounds of Hilda’s enjoyment, and flicked her tongue at the bottom of May’s hairless sack. The moaning coordinator placed both hands on either of her friends’ heads, balancing herself against mounting pleasure as two eager mouths explored her genitalia, one swallowing her dick while the other tugged and sucked on her balls. Hilda and Rosa cast their lust-drunk eyes on Ash, who hadn’t moved an inch since May was unboxed, and gave him a look that said ‘you’re missing out’.
If they were trying to make him jealous, then…
It was working?
Ash looked down and his beach shorts fashioned a bulge that hadn’t been there a minute ago. It had to be the most confusing boner in his long history of boners. While his mind struggled to square up May’s ultra-feminine, pretty features with her unexpected, male appendage, his body rose above any such confusion, quite literally. Hearing the shy, little moans trickle out of her lips and seeing the unmistakable pleasure flushed across her cheeks triggered some instinct inside him. Something inexplicable. Some pleasure he derived from seeing May experience pleasure, cock or no cock.
“Phake iphh ouu,” Hilda burbled. She popped May’s dick out of her mouth and addressed him again. “Take it out.”
“Wh-what? Me?” Ash pointed at himself in confusion.
“Mhm.” Rosa wiped her wet lips dry. “You clearly want to.”
The proof stood right there, right at the front of his swimming trunks. For all three of them to see. Ash didn’t know how to react. He’d been in sexual predicaments before, though never this crowded, never this unprepared. Usually, he could bang his way out of a paper bag, but now he just wanted to hide under one.
Hilda shrugged at his trembling uncertainty. “Or not. I’m sure your friends are still waiting for you at the pool.”
Ah, yes! My friends!
They’d just given him the perfect excuse. “Oh yeah, you’re right. They must be getting worried.” Ash turned his back on the three girls and breathed a quiet sigh of relief. This ‘situation’ was too complex for him to tackle. He couldn’t get involved until he knew what he wanted and he couldn’t just stand there watching like an awkward scarecrow either. “Uh, thanks for sharing, I guess? And don’t worry – your secret is safe with me.” He waved the back of his hand at them.
As Ash ambled towards the exit, doubts and questions tugged on the back of his mind. What am I doing? Is this the right thing? Yeah, it is. I had no business being here anyway. I kind of walked in on them uninvited. Well… they did open the door and invite me in… dang, I hope they don’t think I’m ditching them because it’s totally awkward even though that’s exactly what I’m doing. I hope May doesn’t think I don’t… I don’t…
Of course she would think the worst of him. After she’d divulged the biggest secret of her life, he was practically rejecting her? So much for wanting someone who would accept him for who he truly was. How could he expect that from anyone when he couldn’t do the same? He’d fallen for the idea of May, not the person. Was he really any better than all those vapid fangirls?
When Ash finally reached the door, he stopped short of walking through it. He turned the lock instead.
Hope shimmered in May’s watery eyes as he marched back with renewed resolve.
Ash dropped his beach shorts. His large, proud phallus greeted the young ladies with a sturdy salute. Their eyes grew impressed, May’s the largest of all. He imagined she was comparing his with her own. Even several feet apart, the difference was clear: his shotgun made her tool look like a pee-shooter. There was a ruggedness about his cut member, machismo in the angry vein branching round his girth, a pompousness in how the meaty shaft throbbed hands-free.
May’s nutsack slipped out of Rosa’s shocked lips. “Whoa…”
Hilda’s grip on May’s cock turned slack as her eyes brightened at the shiny new toy.
Ash could see what she was thinking. He confirmed it by stepping out of his shorts, strutting towards the trio and swivelling Hilda’s head from May’s dick to his own. Hilda latched her mouth around his larger cock-head with little encouragement. For all her boyish attitude, she proved a sucker for good dick. He brushed the cap off her head to better meet her lust-studded eyes.
Rooted in awe beside the hung Trainer, May watched Hilda throw her face at the biggest cock she’d ever seen, the same lips that had been working her comfortably a minute ago now enwrapped the meaty girth of her crush. Every bob of her head curved his dick down her gullet with a lewd squelch. What the hell, Hilda? Ash was supposed to be hers!
A part of her yearned to bark at her cock-obsessed friend. Another part considered shoving her aside and claiming Ash for herself. Honestly, the way Rosa froze and stared, too, they were all but three seconds away from devolving into a pack of hyenas clambering over the same piece of meat. May quickly discovered having a dick of her own didn’t stultify her fascination in others.
Ash took note of the two girls who’d stopped what they were doing to watch their bestie administer an enthusiastic, gag-inducing blowjob. It was like they’d never seen a dick before, or perhaps, someone sucking one off. He nudged his head toward May’s crotch area as if to say ‘go on, don’t let us stop you’. Rosa heeded the gesture and took May into her mouth once more, the girl gasping at the sudden tongue on her cock.
Shoulder to shoulder, Ash and May grunted as her best friends’ heads bobbed noisily below their waists. He’d have never anticipated a Valentine’s surprise this incredible, side by side his crush, relishing in synchronised fellatio. Ash turned to see if she was enjoying this as much as he was, and she returned his gaze with her mouth hung open. Their eyes connected in a way they never had before, mutual trust and admiration reciprocated, all in the midst of swaying heads below. Timed to perfection, smiles warmed their panting expressions.
And it was perfection. Ash knew in that moment May’s Penis Surprise wouldn’t be the thing to topple them. He could find ways to work around it; like they were doing right now. Keeping one hand on the back of Hilda’s head, he extended the other to May. She clasped his invitation, fingers intertwined as he accompanied her through the novelty of fellatio. Needless to say, Hilda and Rosa gave the budding couple their blessing, and a whole lot of tongue to boot.
Bundles of clothes and undergarments and swimwear decorated the suite’s floor after they’d all decided to celebrate their nakedness. Ash could tell it was a huge breakthrough for May, probably the first time she’d shown her nude body to foreign eyes. He and the other girls made a concerted effort not to ogle her any more or less than they ogled each other. Not that Hilda or Rosa could get a decent view whilst bent over at Ash and May’s hips, rocked by the pistons of double-teaming dicks.
May glanced over at Ash like an unprepared student hoping to pinch a clue from her neighbour’s desk. She slid her hands round Rosa’s waist to mirror the strong clutch Ash had on Hilda. His pelvis thrashed her bare, white bottom with relentless vigour and lewd clapping noises. If not for the clench round her waist, Hilda might’ve been thrown to the floor by the strength of Ash’s thrusts. May looked on, mesmerized, both by the zest in Ash’s swinging hips and the girly squeals they elicited from Hilda; this, the same tough-talking Hilda who’d prided herself on a hardened, no-nonsense exterior. Just went to show even she wasn’t impervious to a good dicking.
May looked down at her slow and steady tool, sliding in and out of view under Rosa’s butt cheeks. The soft grunts emanating from her close friend were nothing like the dramatic cries of Hilda next door, whose breasts were swaying wildly in their peripheral vision. May didn’t have the practice nor the lower body strength to match the experienced Trainer. Hell, this was the first time she’d stuck her penis inside another person. Despite having something of a pussy of her own, the heat and wetness of Rosa’s felt completely foreign; the grip of wet snatch pulling her dick in and out of its warmth was strangely addictive, and surprisingly explanatory. No wonder people with penises chased after it so much. If she’d known it felt this good, and her friends would enjoy it this much, she might’ve come clean about her genitalia a lot sooner.
May hummed along in muted pleasure as she and Rosa enjoyed each other. They lived in their own little world for a minute before the clapping beside them sped up and got louder. May turned to look just as Ash let loose a carnal grunt, shoved his entirety inside a climaxing Hilda then held himself in there. Hilda’s wobbly legs trembled. She dropped to the floor a hot and used mess. Ash’s semi-rigid cock slipped free and hung several inches between his legs, sleek with Hilda’s nectar and the product of her orgasm.
Ash wiped the sweat on his brow with the back of his arm. “Phew. That was a good warm-up.” A good warm-up? May wasn’t sure she’d even found second gear yet! A fact Ash noticed, too, before spurring her on with a smack to the bum. “Go on, May! Throw your back into it. Trust me. She’ll love it.” He winked.
May switched her gaze right and left between the naked girl bent over in front of her and the naked girl passed out at Ash’s feet. If nothing else, he had the results to back up his method of mad pumping, and Hilda was his pudding.
May silenced the doubts in her head and put more energy into her thrusts. She pulled back until only the head of her penis remained enfolded in Rosa, then threw her pelvis forward as fast and hard as she could, only stopping at the ricocheting smack of supple ass cheeks. Rosa grunted her appreciation at the raise in tempo. And so May strived to fuck her as hard as she longed to be. Fatigue broke out on her forehead and her sweaty hands struggled to maintain purchase on Rosa’s waist, but May didn’t give up, didn’t stop, didn’t slow down.
In the corner of one eye, May caught Ash watching her large breasts jiggle with the brisk momentum of her thrusts. Is this… turning you on, Ash? Watching me fuck my friends like this? The rise of his semi-erection into its full-blooded, sky-pointing self answered the question for her. She blushed and looked away, tried to concentrate on fucking Rosa, but soon she felt his hands caress her arms from behind.
His hot, husky breath titillated her eardrum. “You’re so fucking sexy, May. I love your body.” He groped her big, jiggling tits whilst she rocked her hips back and forth. Between pumping Rosa and enduring the pleasures of twisted nipples, May couldn’t focus on one stimulus over the other. Harder still, was the slick cock grinding up against her spine, spreading vaginal fluids, impatiently waiting to claim its second hole. Evidently, Ash had overcome his phobia about her penis, staring down over her shoulder as they watched it slide in and out of Rosa with lascivious intrigue. Feeling his desire so close and heavy upon her, May found that extra gear and pounded the pig-tailed girl to a squeal-inducing orgasm.
Only she and Ash remained standing over her worn and weary best friends.
“Good job.” He squeezed her shoulder. “Lasted longer than I did my first time.”
“Way longer.” He sounded ashamed to admit it. “That was your first time, right?”
She regarded her erect member with some pride; it was still standing straight despite taking down its first pussy. “Yeah, it was…”
“So, that means you’ve still never seen it… cum?” He seemed to be asking a second question between the lines, wondering if she could cum? Could her penis ejaculate? Well, May had testes – not as large as his – but testes all the same. While she’d never seen her own semen, she imagined her baby batter factory would be hard at production, too. Right?
“I dunno. I mean, I guess?”
“Guess? Not good enough,” Ash said. “I want to see it.”
Geez, now he sounds like Hilda! What’s with all of them wanting to see me –
“Hnnn!” May looked down where, suddenly, Ash closed a fist around her shaft, and began pumping.
“Whoa, so smooth,” he said in awe, like someone who’d never touched a penis before. Did hers really feel that different to his? Only one way to find out…
She reached round her lower back and –
“Oh!” Ash started. He gave a coy chuckle. “A little handsy, aren’t you?”
“Mmm… fair is fair.” She turned the masturbation mutual. His cock felt so much meatier and heavier than hers. The bulging of his veins created a gruff contrast on her palm like nothing she’d experienced handling her own. It amazed her how far up she could stroke his girth before reaching the bulbous crown. As far as penises went, she got the sense Ash had absolutely nothing to be shy about; she could practically feel the confidence throbbing in her fist. If only she’d had half the surety he exhibited.
The Valentine’s couple jerked each other’s cocks as if it were a race to make their lover bust first. Hot and heavy moans clambered over one another. May experienced an unfamiliar tightness in her ball-sack and a surge of adrenaline coursed through her veins.
Is this it? Is it finally happening?!
Ash wasn’t to know how close she was to cumming and, in his boyish impatience, released her cock and spun her round by the shoulder. He pressed his lips hard against hers, instigating a tussle of smouldering, open-mouthed kisses. Their dicks came together like crossed swords; his tall, blunt weapon ruffling her fledgling dagger. The intensity of their snogging couldn’t be contained in one spot; May soon found herself moving backwards while Ash cupped her face in both hands, deepening their kisses as he subconsciously (or consciously) steered her towards the bed. Their hard, swinging dicks clashed every step of the way till the back of her knees hit the mattress.
May fell onto her back with the faintest of pushes. Ash knelt at the foot of the bed and spread her legs apart. He sniffed around her genitals like a Growlithe pursuing a scent, and found his mark nestled somewhere beneath her scrotum. Purring in excitement, he used his snout to scoop up her sack then tucked into the warm and sodden pussy aching for attention.
With all this hullabaloo about her penis, it had been easy to forget her nether lips were just as engorged and responsive to tongue. Ash hadn’t forgotten though. By the looks of it, he’d been eager to dig in from the moment he stepped foot in the room; unperturbed by the pink testicles slanted over the bridge of his nose while he slurped the honey lining her pussy lips.
May was red in the face watching him all but bathe himself in the flavours of her genitalia. Nothing said he could love her despite her cock and balls more than shoving his face flush in the heart of her insecurities, and licking her every crux, crevice and crinkle. She let her head fall back and her eyes fall shut, moaning to the ceiling with the biggest smile spread across her face.
When Ash got done eating up, he emerged wiping his ravenous mouth clean, a little surprised at what he’d just done. Granted, he hadn’t quite sucked dick – but, literally coming an inch away from doing it, was too close for comfort. Or at least, it used to be?
What that said about his sexuality still confused him. Lying spread-eagled before him, May embodied many of the physical traits he appreciated in women: a pretty face, a great rack, sinuous curves, sexy legs… but a cock? A ball-sack slapdash on top of the part he garnered the most pleasure from in females? Yet, the sight of May’s equipment didn’t soften his boner one iota. It almost scared him how much it didn’t. He couldn’t explain how or why but this configuration of body parts May presented really worked for him. Well, no one said you had to have everything figured out the moment you asked someone out; perhaps that was a sub-adventure he and May could explore if they rode off into the sunset. Right now, all Ash knew, was he wanted to bang the living daylights out the busty Coordinator, cock and balls and all.
Knowing from first-hand experience how delicate testicles could be, Ash gently tucked hers aside then inserted himself inside her hidden pussy lips. She was tight as could be. He groaned as the third inch slid in. Her mouth grew wider with each increment of meaty shaft. So nice and wet. Her snatch welcomed him with a snug embrace.
Two minutes later, May decided having a dick was not nearly as fun as getting ploughed by one.
Ash held her thighs apart while he broke a sweat pounding her tight pussy. Her grunts of pleasure came thick and fast, but also high and low. One thrust she sounded like any other girl he’d fucked, then the next like the deep pants escaping her mouth could belong to a guy. Ash chalked it up to some sort of testosterone imbalance, and found it oddly endearing, reminding him of the time his voice had started to break. He wondered if she wasn’t having her own voice and virginity broken all in one go right there and then.
May wept with pleasure as he stuffed her to the hilt again and again. Her fatty breasts swayed and flopped in tandem with the rocking bed, and her dick flailed from side to side and all around like it was caught in a tornado. Rather erotic how she’d retained her stiffness through penetration, almost as if the repeated ramming of her cunt made her cock hard. If she’d had a clitoris instead, he imagined it would be aroused much the same.
Hilda and Rosa popped up from either side of the bed!
Ash was caught by surprise. The rhythm of his thrusts was disrupted for a few good pumps. May looked as though she would ask her friends what they were up to if she had the wherewithal to speak.
Rested and recovered, the two girls decided their involvement in May’s deflowering had yet to reach its fulfilment. Ash supposed it was only fair to let them help finish what they’d started. Not that he could stop either of them descending upon May if he wanted to. Rosa lay next to the brunette getting fucked and French kissed her while rubbing a hand all over her wobbling tits. Hilda grabbed hold of May’s floundering dick and shoved it in her mouth. She did her best to minister a blowjob while the vigorous, bed-rocking motions had the girl’s cock occasionally stab the inside of her cheek. Once Ash recognised the girls had come to see everything out, he worked himself back into an effective rhythm.
Together, Ash, Hilda and Rosa convinced May that, beyond the unconditional acceptance of her body, they truly cherished her inside and out. More inside than out for Ash right now. One powerful, defining thrust hurled her dick out of Hilda’s mouth in what turned out to be a timely jostle. Just then, May’s body tensed – Ash felt it clamp around his cock – then a stream of white, hot gunk jetted out the tip of her penis.
It had finally happened.
She broke free of Rosa’s kiss and a shrill, drawn-out grunt accompanied several ropes of semen shooting all over the place from her whirling cock. Her essence splatted Hilda’s cheek before her flailing penis aimed a spurt as far high as Rosa’s face, and even May herself wasn’t exempt from a splash or two of her own produce.
Ash watched her sack shrivel as its pent-up contents were splattered in every direction but his. The volumes alone spoke of how much May had needed that. And little did she realise, he was but five pumps behind her.
Her sudden pussy clench had almost milked him instantly, but Ash survived long enough to pull out and ejaculate over the three girls, shooting the heftiest of ropes towards May’s face and chest. Streaks of his and her cum lay strewn across their naked bodies, a scene as messy as it was wholesome. Although, not quite for the two people in the room who didn’t have a penis.
“Ew, guys!” Rosa used the bed sheet to wipe May’s cum off one half of her face and Ash’s cum off the other. “Was that really necessary?”
“What’s the matter?” Hilda said. “Scared of a little cum?” She flicked more white goo between Rosa’s eyes. “You missed a spot.”
“Hey!” Rosa huffed. “May, tell Hilda to stop throwing around your semen!”
“May’s the one who blasted it all over this room in the first place!”
“C’mon, it was her first time cumming. You can’t blame her for that.”
“I’m just saying – look up, she even hit the ceiling.”
May scratched the back of her head sheepishly as her best friends bickered. She hardly heard a word they uttered. Ash shrugged as if to say, ‘girls will be girls’. He and May smiled at each other. If their bodies felt any lighter, they would’ve started floating. Who said nothing magical could ever come out of Valentine’s Day?
. . .
Minutes later in the bathroom, Rosa and Hilda put their clothes back on after getting cleaned up. Neither of them could’ve predicted how Valentine’s Day would play out. And neither of them was disappointed. In fact, as they straightened their garbs in the mirror, murmuring their disbelief in the impromptu foursome, the salacious thought of marching back into that room and pouncing on the loved-up couple occurred to them both.
May had an amazing cock. And beneath his humble, nice guy persona, Ash was a monster. Rosa and Hilda could easily see themselves enjoying the pair some more. With the same sly grin on their faces, the girls snuck out of the bathroom giggling to themselves.
But it was Ash and May that surprised them. The pair were going at it again. Ash was railing May from behind, her born-again erection flapping up and down against her tummy.
Rosa and Hilda exchanged a knowing glance. Ignoring their own horniness, the newfound couple was due some alone time. They tiptoed out of the room without the romping pair catching sight of them. Rosa gently closed the door and flipped the ‘Do Not Disturb’ sign.
She and Hilda got to the end of the corridor when a bumbling duo of lads barrelled into them from round the corner. Hilda stalled the tongue-lashing burning on her lips when she recognised the boys. “You two again?”
“Oh, hey!” Hilbert chuckled awkwardly. “May’s friends, right?”
“Have you guys seen Ash anywhere?” Nate asked, looking down the hallway. “He totally ditched us at the pool.”
“Ash is…” Rosa chose her words carefully. “A little preoccupied right now. But maybe there’s something we can help you with?” She slipped a wink at Hilda. And Hilda grinned to confirm she was thinking the same thing Rosa was thinking.
They didn’t wait for the boys to answer before grabbing them by the wrists and dragging them off to a private room. Today was their lucky day. A Valentine’s Day they’d soon never forget.
Author’s Notes: Thanks for reading! Please rate and drop a review to let me know what you thought of this fic!
Special credit goes to ParkdaleArt and @_Gouka for the artwork that inspired this fan fic cover! As of the time of this writing, you can find more of the artists’ work here:
As always, thanks again for reading! Have a nice day and take care!
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