Chapter Five - Sadie and Dorothy

After taking a few days to recuperate with some well-deserved rest, nourishment and hydration, Jaden Yuki felt like a new man. Of course, maybe some of those meals and snacks he had were courtesy of Fonda Fontaine’s miracle milk that seemed to energize him like nothing before. Still, it didn’t matter. He felt better. He felt good.

It also probably helped that he had been getting the absolute best sandwiches at the shop the last few days. He hadn’t had luck like this since his first year. He got the golden eggwich four times in a row this week. Today, he was hoping to make it his fifth. Hopefully Damon wouldn’t mind.

Syrus more or less dove into the large bin and fished for his sandwich before popping out. “Alright! Here goes...” the bluenet whispered before tearing off the wrapping to reveal... a standard jam bun. “Aw...”

Jaden patted his friend on the back. “Hey, better luck next time, Sy!”

“Yeah, I guess,” he said with a sigh. “Knowing yours though, you’ll be pulling it right—”

The brunet shoved his hand inside the bin and pulled out the bread. He tore off the wrapper and revealed the prized sandwich; the illustrious golden eggwich!

“Now...”

Jaden rubbed the back of his head as he took a large bite. “Hey, it might end tomorrow. Who knows.”

Suddenly, he felt two pairs of hands on his shoulders which then spun him around on his heel. He blinked as he swallowed the sandwich. To his surprise, it was the two employees of the card shop; Ms. Dorothy, a plump mature woman who seemed to have never ending problems with her truck and Jaden always helped, and her assistant, Sadie, a tall and slender woman who apparently ran a pretty wicked burn deck. He hadn’t thought about them much before but... they both had a lot of appeal. Older women were experienced and packed with curves in all the right places. It was fun to think about making Ms. Dorothy feel young again—and he really, really, really needed to make it up to her for his and his friends’ comments about her DMG cosplay their first year... and Sadie was just plain hot!

Ms. Dorothy grinned as her eyes met his and Sadie giggled when his eyes met hers.

“Jaden Yuki... for drawing the golden eggwich five times in a row... we offer you a special prize! Come by after closing to come get it,” Sadie said with a jazz hand.

He and a few of the other students blinked. “Was this always a thing?” one of them asked, only to go unanswered.

Ms. Dorothy leaned in towards Jaden’s ear and whispered. “Make sure you come alone.”

Jaden could only blink and nod.

xXxXxXx

The end of the school day could not come any faster. Most students wanted to get back to their dorms as soon as possible, whether to waste time or to spend precious time working on their decks for the upcoming Genex Tournament... which Jaden still wasn’t sure if he was going to participate in. Right now, all he could think about was the supposed prize he won. Why didn’t he get this prize that first year when he pulled it every day of the week? Was it something just for seniors? If so, why did he have to be alone to get it?

All his questions were answered when he slipped into the card shop right when Sadie was about to close the shutters. “Right on time,” she said with a smile.

“Hey, I’m only late for classes.”

She laughed at that. “You should probably fix that. Come on. We still need a couple of minutes to clean up then we’ll get your prize ready.” She led him behind the counter and into a room. A simple old couch, fold up table and kitchenette were in the room. She gestured towards the couch. “Sit down. We’ll be ready to go faster than you can say ‘Get your game on’.”

“...Get your game on.” He smirked.

“Oh, shut up!” she said with a roll of her eyes.

Chuckling to himself, Jaden made his way to the couch and sank into it. It was comfortable despite its age. Ten minutes passed before he started to get bored. He had gotten more patient his last year at school but it was still a big ask to have him sit quietly. Sensing his irritation, Yubel phased into the world. Her ghostly hand dragged across his face before angling it towards her. The two lovers shared a smile before she leaned in to kiss him. Small, chaste pecks on the lips eventually changed to longer, charged and sloppy kisses. He rested his arm around her shoulders as one of her hands slipped between his legs and groped him through his pants.

“Right here?” he asked huskily against her lips. His eyes flashed the unnatural colours as she took a physical form right there in the room.

“You’re bored, aren’t you?”

“Yes but... Aw, what the hell,” he muttered before diving in to kiss her feverishly. Their teeth clacked against each other as their noses bumped into one another. It was messy. It was clumsy. It was wonderful because it was their kiss. Their first kiss in a while since this harem thing took off. Guilt panged inside his chest at that realization. He had really been neglecting Yubel lately. He had to make it up to her soon. Now, he hoped that Sadie and Ms. Dorothy would take all the time in the world.

His tongue slipped into her hungry mouth as her clawed hands worked on undoing his pants. Chuckling, he pulled away just enough for their drooling lips to be a breath apart. “Eager?”

“Like you wouldn’t believe,” she replied simply.

“I better step up my game then,” he murmured before crashing his lips against hers again.

His own hand slid between her trim thighs. She was technically nude all the time but her parts only seemed to come out when she was aroused. To his surprise, her cunt was already there but her cock wasn’t. Whatever, he wasn’t about to complain. His fingers slid between her purple folds and was delighted to feel how she was practically dripping already. Her juices dribbled onto his deft fingers. They glided across her slit. Up and down and all around her clit, he massaged it as she moaned into his mouth. She trembled against him as her hand wrapped around his cock and gave it a few pumps. Soon, he was completely hard in her grasp.

“Please, Jaden, enter me...” she whispered.

Right when he was about to plunge his fingers inside, the doorknob turned. In a panic, Yubel disappeared and floated off to the corner of the room, her cheeks and temper blazing at how embarrassed she was. Jaden, however, was unable to tuck himself away in time for the door to open to reveal...

Ms. Dorothy and Sadie in scantily clad outfits and different colored wigs. Sadie, the taller of the two, was in a reddish-orange wig with a strapless, silky purple mini dress with a deep, plunging neckline that showed off her perky breasts. They were hardly as big as some of the other women he had been with but it flattered her perfectly. The dress itself came up to just below her round ass and her matching purple boots came to just below her knees. She also wore a pair of silken opera gloves. Ms. Dorothy was in a blonde wig with a blue mini dress with a fur trim across the collar and seemed to highlight her deep, ample cleavage. She wore matching fur lined gloves that came up to her shoulders and fur lined boots that came up to her knees. It took Jaden a minute to realize who they were dressed up as; Gemini Elf, a normal monster with pretty high attack points.

Regardless of if he recognized the two’s cosplays, he definitely knew something... He liked the sight of it.

They blinked at the sight of his massive cock out there in the open. Ms. Dorothy clicked her tongue as she turned towards her younger assistant. Her hands placed themselves on her wide, curvy hips, as she let out a sigh. “Now, did you tell him what the prize was?”

“No! He must’ve heard us talking about it...”

Jaden coughed. “No, I, um... I got kinda bored.”

The two women giggled. “Well, you won’t be bored for long. The Gemini Elves are here to make sure you’re properly rewarded...”

Jaden shrugged off his uniform jacket and kicked off his pants. “If I knew this was the prize for drawing the eggwich this whole time, I would’ve tried harder earlier.”

Ms. Dorothy laughed again. “If we knew you were as... energetic and endowed as you were, we definitely would have done something for you in your first year,” she said as she sat beside him and Sadie sat on the other side. Her gloved hand wrapped around the base of his prick and gave it a few pumps. Her fingers were kind of stubby so they had no chance of wrapping completely around his girth but it still felt pretty good. A moan escaped the young man as he gazed towards Yubel who was still huffing in frustration. He mouthed an apology as his head tipped back against the couch. “Sorry you didn’t get the prize back then.”

Sadie took the top half of his cock and dipped her other hand down to his balls. The silky texture of the glove felt absolutely heavenly. Precum dripped from his tip and rolled down his shaft in pearly, translucent pearls. “Oh my, you were really working yourself up, weren’t you, Jaden?” she asked.

“Like you wouldn’t believe,” he breathed. “Fuck, that feels really good.”

“Whenever you feel pent up...” the fake redhead whispered.

“Let us know. We have tons of costumes from my time as Miss Duel Academy,” Dorothy finished. “I can scrounge up something for your favourite Burstinatrix...”

He huffed at the thought of one of the girls in his life dressed up as the flagship femme fatale of his deck. A tight, fire red number that clung to their bodies... He swallowed. “I-I’ll... think about i—Oh, fuck!”

Sadie had dipped down to swallow down half of his cock. Jaden screwed his eyes shut as she felt her expert tongue slither and slather all around his head as her throat clicked and massaged his shaft. Dorothy continued to pump whatever didn’t fit into her mouth. Noisily, the ‘redhead’ choked on his cock. Tight, velvety wet walls squeezed his cock and coated it with thick spit that rolled down to his balls. Her thumb continued to massage his balls as she worked the tip.

Dorothy leaned in towards Jaden and pressed a kiss along his pulse. Her velvety gloved hand was still hard at work at jerking off the rest of him. “You know, I thought about repaying you like this for years. You were always such a sweet, helpful young man, Jaden. Never mind all the times that you and your friends have saved the rest of us...”

He chuckled at that. “Well, I guess you can make it up to me over time... I’ll swing by the island from time to time after graduation to collect.” He reached for her chin and angled her face to steal a kiss from the older, chubby GILF. “How’s that?”

“We’d like that very much... Gosh, no one has lasted this long with Sadie’s mouth...”

“You two do this often?”

Sadie gasped as she pulled her mouth away. Coughing and sputtering, strings of saliva wobbled and snapped between her lips and his shaft. “Not often... We just have to... entertain some important guests from time to time...”

“Though... we might put a stop to that after tonight... I don’t see myself or Sadie being able to pretend that these old men feel half as good as you do.”

The two women hummed in discontent at the thought. Shaking the thought from their minds, they suddenly stood up from the couch. Giggling, Sadie peeked over her shoulder as she hooked her fingers in the hem of her mini dress and yanked it over her round bubble butt. Her bountiful cheeks swallowed up the tiny scrap of silky fabric she called underwear that formed a ‘T’ atop her crack. She swayed her hips from side to side. “I know a few of your friends took peeks at my ass before. So, go on, take it in. No one but you and a few execs get a view like this.”

To emphasize her point, the clerk smacked her ass. Her butt was firm so there wasn’t much wobble but it was still a wondrous sight that made Jaden’s cock twitch.

Dorothy held his cock in place as Sadie moved back to sit on his lap. The skin of her bubbly cheeks was so soft and smooth that Jaden couldn’t help but groan. The sensation of Sadie’s ass pushing against his dick felt heavenly. Not as good as a titfuck or a pussy but still plenty arousing. She ground her hips against him and her boss’ hand before lifting up again and spreading her cheeks. Jaden blinked as he took in the sight of her winking asshole while Dorothy spat onto his cock and gave it a few pumps. Spit smeared across his cock. It took a moment but then he realized what was going to happen.

“I don’t think I’ve fucked a girl in the ass before,” he murmured as she slowly sat onto his lap again. His throbbing cock poked and prodded her twitching hole as he tilted his head back.

“I don’t let guys fuck my pussy without a condom, sorry,” Sadie said with a laugh before finally sinking herself onto that ass destroyer. The two shared a long, deep moan as her greedy asshole swallowed his pole. “Oooh... I might... reconsider that rule. You’re filling me up so good, Jaden.”

Dorothy tugged down the hem of her dress and pushed her admittedly saggy but still incredible boobs into his face. The warm softness contrasted against the firmness of Sadie’s ass in a way that made him shoot precum into her rectum. Jaden groaned. His lips wrapped around Dorothy’s dark nipple and gave it a few hard sucks with an occasional nibble here and there. Part of him expected milk to rush into his suddenly hungry mouth and was disappointed that there wasn’t any. No matter. He’d just have to visit Fonda again later. His tongue lashed across the stiff bud in between his nibbles that made the GILF shiver with delight.

The sound of their shared pleasure filled the room and bounced off the walls. The tightness around his cock combined with the soft, roominess past the constrictive entrance was strange but hardly unwelcome. He could get used to this for sure. Plus, there was just the strange forbiddenness that came with anal sex that made this all the more addicting. It was different from the tightness of a sweet, wet pussy that completely enveloped his stallion shamer of a cock. If someone were to ask, he would probably pick pussy in the end but ass was good. Incredibly good.

Especially if said ass belonged to a girl like Sadie who rode cock like an absolute champ!

PLAP! PLAP! PLAP!

Sadie’s ass clapped against his lap as the orange strands of her wig bounced up and down. Her moans grew louder and louder as her movements grew sloppier. “Fuck... you’re so deep! You’re ruining me! You’re ruining my fucking ass!” the cashier cried out. “Wreck me! Fucking destroy my tight little asshole, Jaden!”

Jaden smirked around Dorothy’s nipple.

“Cum in me! Paint my insides fucking white!”

He huffed.

She bounced harder and faster. Jaden felt his cum churn inside his overworked and tightening balls. She clenched around him, making things even tighter around his fat cock, and forced a groan from him. His hand raised itself and cracked it across her phat perky ass. It wobbled from the impact and the sight of such a luscious booty jiggling on his lap finally made him bust. Hot, thick cum spurted from his cock and splattered across her bowel’s walls. With a cry, he felt something splash against his balls. It took him a moment to realize that the girl came with just her ass.

Shivering, Sadie pulled herself off of his cock. It fell against his toned abs with a meaty thwap. Cum dribbled from his cock and onto his shirt as he breathed heavily. He didn’t even move, it was all Sadie, and he felt like he had run a marathon. He’d definitely make a trip to Fonda later. His eyes drifted towards Sadie’s leaking hole. Slowly, it twitched as it tried to close back up but Jaden’s stallion shamer of a cock left her a gaping mess.

“God... You fucked me up, Jaden. Dorothy, you need to try him!”

Dorothy chuckled as she pulled away from the young stud and slipped between his legs. “I intend to. Just need to get him all nice and ready again since you wrung him dry.”

“Lemme just shower—Holy shit,” Jaden groaned as Dorothy slipped his limp cock into her mouth. He wasn’t sure whether to be grossed out or aroused by the shameless sluttiness that came with going ass-to-mouth. Right now? It seemed like the latter was working. Supposedly only he and a few fancy execs knew how much of a freak the plump GILF was. The young man was sure that he would be beating the other guys off of her with a stick if they knew what Ms Dorothy and Sadie got up to.

Plus, it helped that Ms Dorothy’s slutty mouth was expertly wrapped around his cock. Her tongue knew just how to lick and swirl around him as the near vacuum suction around him made him nearly go crosseyed. Her hand slipped further between his legs and squeezed his balls. Sheer sensation washed over him. His cock throbbed heavily between those heavenly pillows Ms Dorothy called lips. Precum splashed against her tastebuds as he reached full mast.

“Mmmmm,” hummed the older woman as she pulled her mouth away with a lewd POP! “Looks like you’re nice and ready for me now, Jaden.”

“Are you practically anal only as well?”

Dorothy chuckled. “No. When you get to my age, you stop worrying so much about having babies.”

Jaden smirked. “Do you want one?”

The two women blinked. “Are you offering to knock up my boss, Jaden?”

“If that’s what she so desires,” he murmured before leaning down to kiss the much older woman. “I’ll fuck you until you’re even fatter with my kids.”

Sadie bit her lip as Ms Dorothy stared at him with a flushed expression. “I... You’re welcome to try. I’ll be impressed if you manage to do it before my ol’ eggs run out. Alright. Knock me up, Slifer Boy.~”

The three grinned as Jaden stood up and pushed Dorothy onto her back and then pushed Sadie on top of her. Their two incredibly different but incredibly lewd bodies squished against each other as the man lined himself up between the both of their legs. His cock twitched at the sight of their bare dripping pussies. Sadie was plenty wet and dripping onto her boss from her earlier orgasm while Dorothy was almost as slick as she was despite being untouched.

“Let’s get you ready for me, Ms Dorothy,” Jaden murmured as he pushed himself between the two women’s cunts. Sweet, slick velvet surrounded him as his cock hotdogged between their folds. Loud moans escaped the two women as their stiff clits were attacked by such a fat, hard prick. “Fuck that feels good. Regret not letting me in here earlier, Sadie?”

Sadie laughed. “Shut up and fuck Ms Dorothy already.”

“Fine,” he laughed back. He continued to thrust between the two pussies and coat his cock with their slick. “Actually... Give me a show,” he mused as he gripped the back of Sadie’s wig and pushed her face between Ms Dorothy’s gorgeous saggy tits.

Sadie yelped as she felt her face get surrounded by marshmallow soft flesh that wobbled around her. Dazed from her clit’s assault and the suddenness of the push, she looked up from her boss’ tits and watched her expression change from a cock drunk expression to an almost motherly but incredibly lustful look. Her heart and cunt throbbed as she leaned up and kissed the woman. Messily, their lips and tongues mashed against each other as her hands groped and squeezed Dorothy’s massive boobs.

“That’s it... get her nice and wet for me. You two sluts might turn into good girls for me at this rate. Alright, I’m going in.”

He gripped his cock and pulled back much to the girls’ chagrin. Then, he lined himself up with Dorothy’s twitching hole and slammed himself inside. Warm, wet walls sucked him in eagerly as he sank right to the hilt. His swollen balls slapped against her phat ass with a loud clap. His hands slipped from Sadie’s wig down to her curvy hips as he thrust in and out of the GMILF-to-be.

Muffled moans and cries escaped the woman as her pussy easily stretched to its absolute limits thanks to the gargantuan cock that plunged in and out of her. She hadn’t felt like this in years. Decades. It made her feel young again! Whining, she clung to her younger employee whose tongue was wrapped around hers.

Jaden grinned as he watched the two women go at it beneath him. Feeling a bit sorry for Sadie, one hand slipped from her hip to between her legs. Two fingers plunged into her experienced but perfect pussy. They clamped tightly around his thrusting digits. Sadie’s muffled moans soon rang in the air as Jaden fucked the both of them.

Every time Dorothy was thrust into, his fingers pulled out of Sadie. Every time he pushed into Sadie, he pulled just about out of Dorothy.

PLAP! SCHLICK! PLAP! SCHLICK!

The lewd orchestra of the attempted breeding session filled the room with the scent and sound of intense sex. It was an overwhelming display of debauchery, even for someone like Yubel who encouraged this. Her cock, small in comparison to her lover, twitched as the walls of her untouched cunt throbbed around nothing. Jealousy burned inside of her as she ached to get fucked just as hard, or hell, even half as hard, as Jaden fucked those women. She’d even settle for sucking the love juices off his prick while jerking off.

Swallowing, she wrapped her dragonic hand around her cock and thrust into her grip. Her howls of pleasure soon joined the two women’s as she jerked herself off to the sight of her lover fucking them. Pleasure and shame panged throughout her androgynous body as she watched as his hips grew wilder and wilder.

“Cum for me. Cum for me, bitch,” Jaden muttered.

Yubel’s grip tightened around her prick as she watched Sadie pull away from the kiss to scream out in pleasure. Her cunt spasmed around Jaden’s fingers and sprayed lewd juices across all three of their laps. Whines escaped the spirit as her own hips couldn’t stop moving at the lewd sight.

“If you love me—my cock, you’ll cum for me right now.”

Yubel blinked as she looked up and locked eyes with Jaden.

Dorothy cried out as she hit her peak and creamed around young dick.

“C’mon. C’mon... God, yessssss,” he groaned as he pulled out and jerked himself off onto their sticky cunts.

His and Yubel’s strokes synched up with each other as they continued to lock eyes and finally... it was too much. Semen sprayed from Jaden’s tip and splattered all across slut cunts as Yubel spurted out a shot that managed to land a couple feet in front of her.

Panting, Jaden scooped up whatever cum he could get and plunged it into Dorothy’s still quivering cunt. “Get knocked up.”