Spoiled For Choice

by DrySpell

Rating: mature
Tags: My Little Pony: Friendship is Magic, Porn, Sex, Spoiled Rich, Pipsqueak, Human
Length: 4615

After a devastating heartbreak, Pip attempts to drown his sorrows. Drunk and in his feelings, he hooks up with Spoiled Rich for the night. This turns out to be more of a mistake then you would think...

Pip thought his relationship was going amazingly. He thought he'd met the woman of his dreams. Unfortunately, reality is often disappointing. After a breakup harsh enough to rip his heart clean in half, he drowns his sorrows in cheap liquor at a bar he frequents. Being sad and drunk at the same time can lead anyone to do something silly. Even hooking up with a woman you've never met at a bar.

Though she does look eerily familiar...

Contains Cheating(?), Milfs, Prostitution
Everyone in this story is over 21. Gotta watch out for those underage milfs smdh.

Published 2022-05-02 18:30:01 UTC
Last updated 2022-05-02 18:30:01 UTC

Don't Drink and Decide

“Top me off, BT.”

“I really don’t think you should have any more. It’s not responsible to drink this much.”

“Bartop, if I can still understand your English, I haven’t had enough. Now, drink, please.”

Pip hoisted his near-empty glass up and toward Bartop, the bartender, a friend of many years. A friend very much concerned for his fellow friend’s well-being. With a heavy sigh, he grabbed the glass from his hand and filled it up as he’d done countless times that night. Before it even hit the table, Pip grasped at the handle and knocked back half of it. He wiped his face with his sleeve, then chuckled.

“Sorry, mate. That was a bit harsh, yeah?” He said, pressing his forehead into his arm. “You do nothing but try to help and I lash out.”

“It’s okay, Pip. I get that you’re hurting.” He went back to aligning the bottles that had been taken out over the course of the night. By now, the people had started to file out, with only a couple of people still toiling about. “But you and I both know that drowning your sorrows won’t work. You need some rest.”

“If I go to sleep, I’ll… remember her.” His hand gripped the handle of his drink. “I know it's stupid, but it takes my mind off things.”

“I get that, but—” Bartop’s sentence was cut short as the seat next to Pip was quickly filled. Neither of the two had noticed the woman’s approach. “Hey, welcome to Horseshoes and Handgrenades. What can I get you?”

“Champagne, if you have it.” Her voice was stern, which matched her looks. She was clearly on the older side, maybe even double Pip’s age. Despite this, she was still plenty beautiful. Long, purple hair, bright blue eyes that shone like jewels, and full lips. Her dress hugged her body like a touchy relative at a reunion, and only barely went low enough to cover her thighs. Everything about her seemed to demand attention, and Pip couldn’t help but give it to her. “Careful, boy. If you stare any harder, I’ll have to charge.”

“Erm… sorry,” he mumbled, returning to his drink. He drank down the rest of his glass, then sat awkwardly. Thankfully, Bartop returned just as quick as he sped off.

“Here you go, ma’am. Enjoy.” He left the drink on the table, then turned to Pip. “I’m putting my foot down now, man. I can’t endorse this anymore.”

“I know, but—”

“No buts!” exclaimed Bartop. “Look, just give her a call. Maybe this was all a misunderstanding?” After a bit of silence, Pip sighed.

“Fine. I will. I get it.” Bartop gave his friend a smirk, then pulled away.

“Good. I’ll give you a bit of privacy, then.” He grabbed a small bell, then left it on the table. “Ring if you need me.”

“Mhm.” With that small hum of confirmation, Bartop quickly left his sight. He paused, then fished into his pocket, retrieved his cell phone, and gripped it in his hand. Even with nothing in his way, he still couldn’t bring himself to turn his phone on.

“Women troubles, hm?” The woman next to him spoke up. He turned to see her sipping from her glass. “And you turned to alcohol to deal with them. Pathetic, but not uncommon.” Pip was taken aback, then frowned.

“W-What would you know?” he snapped. The woman chuckled, only upsetting him more.

“A lot, actually.” She placed her glass down. “The name’s Spoiled Rich. I’m something of a heartbreak specialist if you understand what I mean.” Her eyes met his, and the fierceness of them made him back down. “In fact, I’m sure I can sell you a cure.”

“What are you on about?” asked Pip. He tried to hide it, but Spoiled’s words had frazzled him. “What cure?”

“You’re looking at her.” Before he could ask for an explanation, she reached for the hem of her dress. With a single motion, her breast popped out with ease, nearly pulling Pip’s eyes from their sockets. Blood rushed to the wrong head, causing all of the words he wanted to say to die in his throat. “I’ve never seen a case that a one-night-stand with me hasn’t solved.”

Pip stared absentmindedly at her exposed chest, his dick going from a chub to a full-on rager in a matter of seconds. Still low on blood in the right head, his hand instinctively reached out. Before he could even think to get close, the back of his palm was swatted away.

“I like the enthusiasm, but I’m not free,” she quickly made herself decent again. “$300 for an hour. Don’t waste my time if you can’t pay.”

“No, I can pay, but…” He gulped, then looked at the phone still gripped in his hand. “M-Maybe Bartop was right. I think I should give her a call first.” Spoiled’s hand reached up to his chin, pulling him back toward her. Her other hand pressed down on the phone.

“She didn’t pay you any mind when she dumped you.” Her tone was stern, but there was a familiar feeling of emotion underneath her words. “Don’t you want to get a bit of revenge against her?”

Pip kept silent for a few moments but eventually responded with a small nod. Spoiled smirked, reached into her purse, and withdrew a few dollar bills. She slipped them underneath her glass, then got to her feet. Her hand moved from his face to his arm. She locked them together, and pulled him in.

“Good. Then follow my lead, boy.”

After exchanging the requested $300, the pair quickly made their way into the cool night air. Spoiled all but dragged him on a short walk to a few buildings down: a run-down motel named the Sunny Sands Inn. They entered the small lobby and confronted the very clearly sleep-deprived clerk. The two asked for a room, which Pip would pay for, then headed in the direction of it.

The rooms weren’t anything to write home about. A TV, bed, small bathroom, and desk were all present and looked clean. Only the bed seemed to matter to Spoiled, though. She nudged Pip forward, and he sat down.

“Get comfortable.” She slid her arms through the straps of her dress, allowing it to slope off her breasts. Just like before, they stole away all of Pip’s attention. Once she realized that, she smirked, then slowly got down to her knees. “Don’t worry. You’ll have plenty of time to admire these.”

Just as quickly as she exposed herself, she was through Pip’s jeans. Instead of pulling everything away, she let his dick poke out from the holes in the clothes. Immediately, she began running her tongue up and down the shaft. A shiver ran up Pip’s spine as her tongue flicked a bead of precum off of his tip. After a few more licks, her tongue wrapped around the shaft, and she dove down.

Though he should have expected it, her mouth work was amazing. Her tongue moved in ways more like a snake than a human body part. It flicked, prodded, swathed, and everything in-between as she throated his cock. Pip couldn’t help but grasp at the sheets as he watched.

“W-Wait, hold on,” Pip said, breathlessly. Spoiled had dove down far enough to press her nose against his skin. Still, she looked upwards and met his eyes when he spoke. “S-Shouldn’t I do something for you, too?” After a few moments of silence, Spoiled pulled back, popping his cock out of her mouth.

“Why should you?” she asked. “You paid me for this, remember?”

“Yes, but…” He fumbled with the words. “Isn’t this unenjoyable for you, then?” Spoiled’s stern gaze returned, but she didn’t say anything. Instead, she got to her feet.

“Well, if it’s a reasonable request from a customer, I have no reason to not play along.” She climbed onto the bed next to him, turned around, then lifted her leg over his body. Pip leaned backward just before Spoiled’s ass hovered over him. “Although this was your request, do try not to disappoint me.”

Pip’s eyes spread over the massive area now available to him. Her dress had hiked up, revealing what could technically be considered “underwear”. In reality, it was a string of fabric that was barely enough to cover her pussy from view. With a finger, he pulled them to the side, giving him full access.

While he was admiring, Spoiled had once again taken action. She dove down, even more ferociously than before. She’d matched and surpassed her previous speed. The sensation was enough to nearly send Pip reeling, but he managed to keep his head on his shoulders. He licked his index and middle fingers, then pushed inside slowly.

His fingers rubbed along the walls of her pussy. Pip paid close attention, feeling out her reactions as he went. Though Spoiled did well to hold it in, he could feel the subtle feedback she gave him. She would twitch here and there. And sometimes, she would clamp down hard. Soon, he found exactly what he was looking for.

He hooked his fingers and pressed down on the spot he found. It squished against his fingers nicely and pulled a low hum from Spoiled’s lips. Not quite a moan, but not something Pip could ignore either. In response, she slowed down, but by no means stopped. Pip pulled his fingers out then pulled her down. Now, her hips rested on his chest, and her breasts pressed against his stomach.

“Hmph,” hummed Spoiled. She pulled up until she was just barely over the tip. “You’re a cocky little brat, aren’t you?” Pip didn’t respond, instead focusing on eating her out as quickly as possible. Spoiled grasped at the base of his cock, then snaked a hand under his leg. Pip flinched as she grabbed his balls in her hands. “Let me show you the difference between us, boy.”

From then on, it became a war of attrition. Though he flicked his tongue madly around her cunt, the winner had been decided from the start. Pip had a strong showing, but he’d already gotten too close to his limit. Underneath Spoiled’s oppressive skill, he stood no chance. With a primal grunt from his chest, cum shot from his tip, splatting against the roof of Spoiled’s mouth. In response, she dove down deeper than before, threatening to swallow his cock whole as she gulped down his seed.

After a few shaky breaths, Spoiled pulled herself free of Pip’s now weak grasp. Her hips left his face, leaving a thin line of cum behind.

“Close, but you still have a long way to go.” She slid forward to mount him properly. Instead of penetrating, she pressed her plump lips against the shaft. She shook her hips side to side, slowly reviving Pip’s quickly softening chub back to its former glory. “Still, I think I should reward you for the attempt.”

Unlike her blowjob, she took her sweet time putting his dick inside. She shook her hips seductively as she slowly lowered herself onto the tip. As she pushed in, Pip could feel her warm, wet pussy begin to part for him. He gripped the sheets tighter and tighter with each inch of ground she gained. But before her hips got too far down, she paused. Now suspended about halfway down on his cock, she placed her hands on the bed on either side of him. With another playful shake of her hips, she slammed down with a loud slap onto Pip’s thighs.

“Ahh…” Pip cried out in pleasure, his tip poking the back of Spoiled’s pussy. She didn’t make it easy for him to regain his composure either, swaying her hips side to side and shaking her ass to rub his glands from the inside. The sensation was mind-numbing and unique, but it didn’t remove his wits completely. “W-Wait! Condom…”

“I’ve had my tubes tied for years,” she said proudly. “You don’t have to worry about any kids.”

“But I haven’t even done it raw with my girlfriend.” Spoiled paused, then lifted her ass up slightly. Before Pip could even get his hopes up that she was listening to him, she slammed back down coaxing another guttural moan out from him.

“There’s a first time for everything, boy.” She turned to face away from him. “Now be quiet, and let me work.”

Pip heeded her demand only at first. The first few times, Pip managed to endure it. But the weight of her ass pressing down on his dick, squeezing him surprisingly tight each time it did, was too much for him. At first, he was simply breathing heavily. Soon, he was full-on moaning. He grasped at the sheets, but he couldn’t hold it in.

Spoiled pulled herself up onto the bed, then slowly spun around to face Pip. She put her hands on his chest, then picked up the pace. Pip ears were filled with the sounds of sloppy sex. His thighs were slowly covered in the cum leaking from her bottom. All the while, bubbling up inside of him was another load ready to blow.

His hands shot out to her thighs, gripping them tightly. Just as quickly, he moved them to her ass, pulling her down and locking her in place. Pip stared up at the ceiling, then closed his eyes.

“What’s wrong?” asked Spoiled triumphantly. “Too much for you to handle?” Pip paused, then chuckled.

With a simple, swift movement, he pushed his hips up against Spoiled, breaking her balance. Pip grabbed her side before she could fall over, then twisted his body just as quickly. In a matter of moments, Spoiled had been pinned onto her back. Pip now held control over her. If her expression was anything to go off of, she was confused and startled.

“What the fuck are you doing?” Her question fell on deaf ears. In the scramble, Pip’s cock popped out. He took a moment to let his pants drop to the ground, leaving his bottom half bare. He led his tip to Spoiled’s pussy, then slid it up and down near the entrance.

“You know, you remind me a lot of my girlfriend,” said Pip. He leaned down and latched onto her nipple with his mouth. Her grunt as he did so egged him on. Imitating Spoiled’s tongue as it worked his dick, he flicked, swathed and sucked at her nipple until he was satisfied. With a rough pull, her breast bounced back into position.

“What is that supposed to mean?” asked Spoiled. Her frown seemed to be getting more intense by the second. Thankfully, Pip didn’t plan on seeing it for much longer.

“Nothing important,” he replied. He pulled back enough to give his dick some breathing room. “After I make you cum, I’ll call her. I owe her an apology.” Spoiled scoffed again.

“Ha, what a joke,” she said with a wicked sneer. “Only a minute ago you were about to blow. I know a man at his limit when I see one.” Pip could only laugh at her taunts. His hands reached for her own, and he grabbed each wrist in a tight hold. Pulling her to him, he slammed forward into her, digging deep with the tip as it pushed through. Instead of her usual stone-cold glare or a shit eating grin, Spoiled let out a cry of pleasure. Judging by her expression, it was as much of a surprise to her as it was to Pip.

Pip took off like a mentally exhausted retail worker. Any trace of the man from before slipped away, replaced by an unstoppable machine of sexual prowess. Every thrust was supplemented with a hefty thwack as his hips cannoned into her ass. There were no half-hearted strikes, no breaks, no mercy. Pip pounded her pussy like it needed to be tenderized. And Spoiled didn’t enjoy a second of it.

Or, that’s what she wanted to tell him. Over her career, she’d seen more dicks than a trashy fraternity. Some were much larger than Pip's, though he wasn't the smallest of the bunch. She’d fucked men with much more stamina, but again, he was standing his ground. Something about the combination of Pip’s endowment and his vigor caused her body to react with overwhelming pleasure.

She grit her teeth and balled her fists. Every sloppy slap of his tip against the back of her pussy sent a shock up her spine. Her legs, which were previously spread, slowly wrapped around Pip’s legs. His hips had less room to slam into her with, and so, he was slowed down significantly. He let her hands go, putting one on her leg near his hip and the other on her exposed breast, fiddling with her erect nipple.

"What's wrong?" asked Pip with a mocking tone. "Too much for you to handle?" Spoiled's glare of rage was all the answer he needed. He chuckled, then continued. “I have to commend you, Spoiled. You’re more stubborn than my girlfriend.” Spoiled took a deep breath.

“Can you do anything other than compare others to your ex?” she snapped. Pip smirked, then slammed into her hard enough to rip a low moan from her lips.

“Jealous?”

“In your dreams, boy.” Pip pouted.

“You know, this boy has a name.” He leaned down, putting his hands on either side of Spoiled’s head. “It’s Pip.”

“You’re still a boy to me,” she said. Pip chuckled, then slowly picked back up his pace.

This close together, Pip could feel her uneven breathing against his face. Every few jabs, she would gasp just a bit underneath her breath. Pip leaned down, running his tongue along her neck. Once he found a nice spot, he placed a kiss on it. Now even closer, he could whisper his words right into her ear.

“Hey, you said you’d make any reasonable requests, right?” The only response he got was a small hum of agreement. He once again picked up the pace. “Well, I just want you to be honest with me.”

“What do you mean?” As he approached his former speed, he could tell that her breathing was getting heavier.

“How many times have you cum so far?” he asked. “You’re good at hiding it, but I can still tell. You clench up, and your face goes red. Like it is now.” Pip expected a witty retort, but all he got was her shaky breathing. "It's got to be once or twice, at least." A moment passed, then several. After almost a minute of silence, Spoiled finally spoke.

“You're delusional...” She spoke so low that even this close, Pip could barely hear her. “You've got no talent for this. You should throw in the towel now.” Pip chuckled, then snaked his hands underneath her back. He pulled her closer to him, lifting her off the bed just a bit. She grabbed onto his arms for support. “Fucking… cum already.”

“Ask me properly,” he asked. “That's a reasonable request... right?”

“Ugh… this foolishness never ends,” mumbled Spoiled. Despite her protests, her heavy breaths had long since turned moans. Her fingers dug into Pip’s arms, and her legs gripped his hips in a tight vice. “Cum for me, Pip. Cum this instant.”

Even before those words had been whispered into his ear, he obliged. A long session of edging came to an explosive end with a hefty grunt from Pip. He thrust in again, a thick line of her cum splattering against his thighs. Soon, they’d be joined by heavy ropes of cum as they shot through her pussy. They splashed against the back wall and quickly pooled at his tip. Each twitch of Pip’s cock pulled a soft moan from Spoiled’s mouth.

After a few moments, his cock went dull. Her grip on his body loosened until she let go entirely. Pip, a bit slower on the draw, let her go and slowly pulled out. A thin stream of cum followed suit, dripping own to her ass and seeping into the bedsheets. Pip rolled over onto his back, laying down next to Spoiled.

Neither spoke to the other after he laid down. The only sounds in the room were the two catching their breath, and the whistling of the breeze as it came in through the open window. Though the silence was tranquil, it wouldn’t last for much longer.

The buzzing of a cell phone took Pip’s attention as soon as it went off. He sat up, then looked for the source. The light in his discarded jeans gave it away. He reached down and grabbed them, retrieving the phone, and checking the caller ID. His blood ran cold once he saw it. Still, half through muscle memory and half because of the alcohol, he answered the call with a quick swipe.

“Pip?” The voice on the other end of the line was rife with worry. It stabbed a dagger of guilt right through Pip’s chest. “Oh my god, you finally picked up. Do you know how long I’ve been trying to reach you!?”

“I… apologize,” said Pip. He pursed his lips. “I didn’t want you to worry.”

“Well, you did! I was worried sick!” She sounded furious over the phone, but it only calmed Pip down. "I thought you might have done something drastic after I dropped the news. I... don't know if I could've lived with myself if something happened to you because of me."

"I understand," said Pip. "I'm okay. I just had a couple of drinks at Bartop's, but nothing dangerous." The breath of relief on the other side of the phone warmed Pip's heart.

"I'm glad..." Her sentence trailed off, and she sighed. “I shouldn't get mad at you. It was me who did something stupid. I should’ve never listened to that crotchety old bitch.”

“What do you mean?” he whispered.

“It means… that I made a stupid mistake.” She sighed, then continued. “I shouldn’t have ever dumped you." Pip almost couldn't contain himself. He gripped the phone tighter.

"You're taking me back?" he mumbled.

"If you'll have me," she said. 'I… still love—”

“Mmmh, Pip.” If Pip’s blood ran cold before, it froze over at that moment. His eyes flickered back to Spoiled, who was now crawling towards him. She reached for him from behind, running her fingers up his stomach and chest. She brought her mouth right to the phone and continued. “I need you to fuck me again. I can go all night if you want…”

The following silence was maddening. Pip wanted to muster anger at Spoiled for throwing the situation into turmoil. He wanted to muster anger at himself for even putting himself in this situation in the first place. He even wanted to muster some sort of defense to stop the incoming storm. But instead of a storm, it was more of a single drop of water in a calm lake.

“Mom?” The words sent a shock through Pip so severe, he opened his mouth to respond without thinking.

“Spoiled Rich is your mom?”

“Diamond is your girlfriend?” asked Spoiled. Surprisingly, she didn’t seem to be all that phased. “Diamond, my dear, you have horrible taste in men.”

“You fucked my mom!?”

“No! I-I mean, it was an accident!” Pip fumbled with his words and knew it wasn’t going to be enough. Still, he had to try. “I had no clue she was your mom.”

“So just because you didn’t know, it’s okay?” asked Diamond, fury clearly rising in her voice. “You still had sex with another woman while we were dating!”

“But you dumped me…” said Pip, looking down. “I got so depressed that I started drinking too much… one thing led to another…” Diamond started to complain, but her words never came out. After a moment of silence, she sighed.

“I knew I shouldn’t have listened to mom about us. This is all that stupid bitch's fault,” she said. “I thought… that by breaking up with you, you’d want me more. Like a “playing hard to get” kinda thing.” The revelation lit another warm fire in Pip’s chest. He smiled, then chuckled.

“I already thought you were the perfect person for me,” said Pip. “I wouldn’t ever pick someone over you. I can promise you that.”

“Hmph.” Diamond sighed. “But you already did. My own mother at that.”

“I swear to you, that was an accident.”

“What a rude thing to say to that ‘accident’s’ face.” Spoiled hadn’t moved from her position. Her hands were still wrapped around his chest and her chin rested on his shoulder. “And if I’m not mistaken, you loved fucking this ‘accident’ raw.” Pip's heart climbed to his throat.

"N-No, that's not... I mean it wasn't like that." He wanted to get out any excuse or explanation, but fumbling his words only made him look worse. Moreover, even though her silence, he could hear Diamond's anger bubbling up to a boiling point.

“Pip.” Diamond hadn’t spooked Pip with just her voice in a very long time. It was almost nostalgic hearing it so full of hidden fury. “Where are you?”

“The hotel next to Bartop’s,” he answered almost immediately. When she was like this, getting straight to the point was necessary.

“I’ll be there soon,” she said. “Do. Not. Move. Either of you.”

“Are you sure, dear?” Spoiled asked, clearly enjoying herself. “Just me and your boy toy in a room alone for all that time?” She squeezed Pip’s chest, only accentuating her words. “A few more accidents might—” Pip’s hand flew up and covered Spoiled’s mouth.

“See you soon, honey!” He said, quickly trying to overwrite Spoiled’s words. Judging by the growl on the other side of the phone, it didn’t work too well. “Don’t worry, nothing will happen!” She was quiet for a few moments, but she eventually answered with a quiet hum of acknowledgment.

“I’ll trust you,” she said. “See you soon.” With that, she hung up the phone. Almost immediately, Spoiled pulled away from Pip. He turned to look at her, but she was already fiddling with her makeup.

“Why’d you do that?” asked Pip. “What’s the point in riling up your own daughter like that?” Spoiled grunted.

“That brat is less of a daughter and more of an annoyance I have to deal with,” she said, unfazed. “I’m surprised you put up with her.”

“She can be quite standoffish at times, but she’s a real sweetheart if you get to know her,” Pip retorted. His defensive tone pulled a taunting laugh from Spoiled.

“Sweetheart is a new one,” she said. “Her exes always stuck to bitch, cunt, and the like.” She closed the makeup case she’d been using for the last minute, then turned back to Pip. “So, up for another round?”

“What?” he asked “Are you serious? Why would I—”

“Well, we’ve got thirty minutes left. Plus, there's no telling how far out Diamond is.” She shrugged, then continued. “And besides, you already committed the crime. There’s no double jeopardy in my court.”

“Diamond would kill me.”

“She’ll get over it,” she said, crawling on the bed. “Besides, you didn’t really think I’d sit here and play nice, did you?” Pip’s jaw had long since hit the floor.

“Are you really that horny?” Spoiled paused, then laughed.

“I’m always horny,” she responded. “Now come beat this pussy up, boy.” Pip looked her in the eyes, then closed his own. He took a deep breath, then another.

“Fuck me,” he said, with a heavy sigh. “I'm going to be in so much trouble…”

Author's Note

After-Sex Smoke