Personal Trainer of MILFs Ch.2 (Kim Possible)

Read Chapter 1 here 

A/N: Poll Winner. Glad to be back posting! Felt weird to take such a large break. Also changed the name of the story and removed 'Two MILFs' from the title.

Summary: The threesome in the Parr house was a little too loud. That attracted the curiosity of another fat-assed MILF that couldn’t help but join in on the fun.

Pairings: Ron Stoppable/Maddie Fenton/Ann Possible/Helen Parr

Sweat dripped down Ron’s body as he gasped for air between big gulps of water. He was in Helen’s house again to be her ‘personal trainer,’ though, with Ann’s presence, personal might not be the right word. In fact, Ron hadn’t been much of a trainer either, unless shaping Helen’s pussy into a perfect fuckhole for his cock could be counted.

Ever since Ron had fucked the two MILFs a week ago, not a single day went by where he missed pounding their tight holes. Whenever there was a bit of free time, Ron pulled one of the MILFs into lust-fueled rutting until he left them with a bloated stomach from the cum dumped in their wombs. Though that might seem like Ron was being too rough on them with the number of times he pulled them into pussy-stretching fuck sessions, they weren’t much better.

The MILFs still weren’t satisfied when Ron left them with cum streaking across their curvy bodies and teamed up often to drain his balls even more. This was one of those times.

Ron had just left the stacked MILFs drunk on his cum in the living room before he escaped to get a little breather. Even he needed some time to recover after fucking the women constantly for the past hour. Plus, Ron figured that Ann and Helen would appreciate it if he let their voices recover from the screams he wrangled out of them. Just remembering the usually put-together Ann screaming at him to ruin her pussy made Ron’s cock twitch in arousal. Fucking Ann was a dream come true, but adding Helen to the debauchery made Ron question if this was an unreal dream.

After finishing the glass of water, Ron wiped the sweat on his forehead with the back of his hand before walking back to the living room. A smirk couldn’t help but form on his lips at the sight presented to him. The fat-assed Helen was still bent over the side of the couch with her cunt dripping out globs of cum that Ron had dumped inside her. She was weakly moaning into the cushion while her legs occasionally twitched from the aftershock of the orgasms that wracked through her body. Ann wasn’t in a much better shape, with her beautiful face covered in jizz with drops occasionally swallowed by the redhead whenever she licked her lips. Her perky breasts had bite marks from the attention Ron had given them while her pussy was in a similar state to Helen’s.

Ron absentmindedly stroked his cock back to life while walking over to Ann. Helen might be a great partner, but even she needed a break from getting her fat ass drilled from behind for over an hour. Besides, Ron couldn’t get enough of the fact that he could now fuck Ann Possible.

Ann felt something warm drop on her taut stomach and opened her eyes blearily to see Ron’s massive cock leaking precum. She felt her pussy try to squeeze down on a nonexistent cock in reaction to seeing the bitch breaker above her. Ann winced at the soreness her lower body was experiencing but was still game to give that monster another ride.

That would have been the plan if not for the doorbell ringing right at that moment. Ann’s eyes didn’t leave Ron’s cock as she asked, “Are you going to answer that?”

Ron was obviously going to ignore whoever was ringing the bell, but another ring made him pause for a second. When he set his mind to ignore that too, a woman’s voice interrupted him.

“Don’t ignore me, Helen! I know you’re in there! If you don’t want all our neighbors to hear what you’ve been doing, you better let me in!”

Ron blinked and looked at the woman that was being spoken to. Helen was far too fucked out of her mind to know what was happening around her. She moaned after shuddering when another large glob of cum escaped her pussy.

Ann, who wasn't in a much better situation, said, “Maybe you should let her in? Kim is still in the house and I rather not take any chances.”

Ron looked down at his exposed cock and then at the freshly fucked bodies of the two MILFs incredulously.

The redhead giggled and said, “I know who that is. Maddie just moved here, and we’re becoming fast friends. As for letting her see us like this… Let me just say that it won’t be a problem.”

Even though Ann practically encouraged Ron to answer the door in the nude, Ron still grabbed a towel to cover himself. It didn’t do much to hide his massive cock, but it at least let Ron know he wouldn’t be flashing the entire neighborhood. He had a simple plan. Tell the persistent women ringing the bell that Helen was occupied and return to Ann.

Plans never go as intended.

Ron swung open the door and was left speechless. The woman standing outside was the same caliber as Ann and Helen in terms of hotness. And this new MILF was wearing a teal jumpsuit that left nothing to the imagination. The skintight outfit exposed every bit of her curves, and Ron loved what he was seeing.

The woman was shorter than the statuesque Ann and even a bit shorter than Helen. Still, her breasts were larger than the two MILFs he was fucking on the regular. The short height made them look even bigger than they actually were. On top of that, the woman had an unrealistically tiny waist that quickly ballooned into wide hips to complete her look. Ron had a stupid look on his face as he stared at the new MILF that appeared in front of him. He idly wondered when there were so many attractive older women around him.

Ron knew that these three were outliers, but it was almost unbelievable that women with looks of their caliber conveniently moved into the same neighborhood.

“Holy shit…”

Maddie Fenton had just moved recently to her new place and found herself making fast friends with Helen and Ann. They usually spent time gossiping their free time away, but lately, Maddie’s two new friends became very busy. They were so busy that they rarely called to chat anymore. Maddie initially thought that they might be avoiding her for some reason, but after a little bit of investigation, she quickly found that wasn’t true. Those two sluts were fucking the days away with a much younger man. And from what she heard from eavesdropping, that much younger man was a fucking machine.

Maddie could use some of that.

With Jack no longer a part of her life, Maddie hadn’t had some relief in a while, and joining her new friends would be a convenient way to break the dry streak. She had been switching back and forth with her decision right outside Helen’s house. Every time she was about to chicken out, Maddie heard the screams of pleasure ringing out of the house and quickly changed her mind. When the sounds of fucking finally stopped, she decided it was time to be part of the action.

The man that answered the door wasn’t what Maddie expected. She had heard of a blonde hunk that lived close by, but Maddie thought it was one of those overly built bodybuilders. Ron had the perfect amount of muscles that made it look like he could manhandle Maddie without being too much. She raked her eyes over his cut figure and drank in the eye candy before a large tube-shaped pole slowly rising under the towel barely covering Ron caught her attention. Maddie smirked and realized it would be easier than she thought to get some of this cock.

“Well, hello there, handsome. Is Helen in?”

Ron bit his lip when Maddie cocked her hips, drawing attention to the shelf of an ass that the woman had. The towel wrapped around his lower body was utterly pointless now since his cock was almost touching Maddie’s thicc thighs. In response to the new MILF’s question, Ron sidestepped wordlessly to let her see Helen’s completely wrecked body bent over the couch.

Maddie’s eyes widened before her breathing became a little deeper at the sight of Helen looking like she had taken on an entire football team. She didn’t miss that Ann wasn’t in much better shape right next to Helen. Maddie gave Ron an impressed glance since he was still standing as if he could go for a couple more rounds after what he had done to them.

“Impressive,” Maddie said with a smile, “Did you do that all by yourself?”

“Do you see anyone else here?” Ron was surprised at his own pride at that. And was also offended at the thought of someone else with his women.

“That’s some… talent you have there. Since you’re still rearing to go, do you want to see if you can handle another woman?”

Previously, if someone like Maddie came onto Ron, he would have been a stuttering mess with a fire-red blush. But Ann and Helen literally fucked that out of him in the past few days so that Ron was gone for good.

“I’d prefer to know the name of the woman that’ll soon be addicted to my cock.”

Maddie stepped into the house before shutting the door behind her and yanked off the towel blocking the monstrous cock underneath. She let out a small gasp before lightly running her fingers over the protruding veins running along his shaft.

Ron looked down at the stacked woman with dark eyes as she teased his cock. He lifted her chin to look into her stunning purple eyes and said, “You still haven’t given me a name.”

“Maddie.”

“Maddie,” Ron repeated while drawing his face closer to hers, “I’m sorry to say this, but from now on, you’ll never be able to get off without my cock.”

Maddie had to hold back a laugh at the beyond ridiculous claim. At least she now knew that the man was hilariously awful at trying to sound sexy behind this perfect body. Still, Maddie had no intention of letting this stop her from sampling what Ron had to offer. Her light strokes changed when her fingers wrapped around his wide shaft. Maddie hadn’t even moved further into the house, but she was already starting to jack off Ron’s cock like a raging slut.

Ron didn’t think a woman giving him a handjob would affect him anymore because of how much sex he had recently had. Maybe it was because it was someone new, but Ron almost came when Maddie stroked his rock-hard cock nonchalantly. His eyes didn’t leave the delicious bounce of her big tits as her arms moved while working his dick.

“You know he’s being serious? Ron might be a goof, but he was built to ruin us for other men.”

Maddie focused a bit of attention on Ann, who had her fingers between her legs and leisurely moved them in circles on the nub above her abused pussy. “I don’t think you need to inflate his ego, Ann. Ron seems more than happy to give you a good fucking without it.”

Ron narrowed his eyes at the newest MILF he would demolish. He didn’t like that she seemed to treat what he said like a joke. And Ron really didn’t like that she tried to talk him down to one of his women.

Ann giggled, “You’re going to regret that.”

Maddie only got out a startled sound in confusion when she was lifted effortlessly into the air before finding herself wrapped around Ron’s naked body. The thin material of her jumpsuit did nothing to block the feeling of his massive cock pressing into her pussy and extending well past her belly button. Maddie was well aware of how large it was since it was just in her hands, but having a clearer representation of how deep it would go in her body made her pussy drip in arousal.

Ron supported Maddie with his hands on her ass, his fingers sinking into the soft cheeks of her flesh. He groaned at feeling the fat ass in his hands and unconsciously grinded his cock into Maddie in reaction. As Ron dry-humped into her taut midriff, his leaking tip left clear streaks of precum on her teal jumpsuit. It was a privilege to turn another fat-assed MILF into his cock-addicted slut.

“Oh!” Maddie pushed her large breasts into Ron’s chest as she tightened her legs around his waist. While moving her hips in unison with Ron’s, Maddie grabbed his head and brought it toward her’s to meet him in a kiss. She moaned as Ron quickly overpowered her tongue and started exploring the depths of her mouth. Ron quickly dominated the kiss as Maddie focused on wrapping her lips around his tongue and sucking on it.

A sharp sound of a palm landing on flesh filled the room as Maddie squealed into Ron’s lips simultaneously. The MILF felt her pussy gush when Ron repeated that action and spanked her fat ass again repeatedly. Her logic-defying ass bounced under Ron’s punishment until the blonde finally stopped when he dropped Maddie next to his two other lovers.

Maddie’s face was flushed red, with her lips swollen from the rough kiss. Ann pulled her new friend, and most likely newest partner in bed, into her body until their curves were mashed against each other. Ron licked his lips at the amount of tit-flesh available to him.

“I told Helen to keep you away for as long as she could, but I guess you would have eventually joined us anyway. Probably for the best. Ron’s stamina is unreal….”

Maddie wondered what she had gotten into and if it was too late to back out. It was like Ron’s cock had turned Ann and Helen, who Maddie knew to be strong and productive women, into a pair of needy sex-obsessed sluts. Before she could think too much of it, Ann captured Maddie’s lips and took over where Ron had left off.

While the two women fell deeper into the impromptu makeup session, Ron stared at them with an increasingly lecherous look. He kept his cock hard with the steady movement of his hand as he stalked over to his future conquest.

Ron’s plan was simple.

Get Maddie filled, and overfilled, with his cum and keep pounding her into orgasm after orgasm until all she thought of was when she would get fucked the next time. Basically, what Ron had done with Ann and Helen. If it worked with them, there was no reason to change his strategy. After all, it looked like Maddie was as much a size-queen as the other two MILFs were. A look at his massive cock was all that was needed to get her down on her knees.

While Ron was getting ready to make Maddie his, the woman in question still had her lips sealed by Ann’s. Not only was she experiencing kissing another woman for the first time, but Maddie also got an early taste of what Ron’s cum was like. Ann’s gorgeous features were practically covered in the stuff, so simply kissing her meant some of Ron’s cum was swallowed by Maddie. Surprisingly, the redhead’s mouth seemed even more coated since Maddie could taste the salty spunk as her tongue battled Ann’s.

Soon, Maddie’s face was pulled away from Ann’s by Ron. In another show of strength, he lifted Maddie off the couch and claimed the cushion under her before planting the MILF on his lap. Maddie moaned when his cock swiped her covered pussy before settling between their bodies.

“I think that’s enough of a warmup. I can feel your pussy dripping through that jumpsuit.”

Ron suddenly tore a hole in Maddie’s clothing before continuing to rip apart the jumpsuit until her lower body was exposed. Maddie’s jutting ass was covered in red handprints from Ron’s spanking. He was also pleased to see that she was going commando underneath. Ann reached under Maddie and ran her fingers over her pussy before plunging a couple fingers inside.

Ann ignored Maddie’s sigh of pleasure and said, “She’s more than ready for you, Ron. Do you want some help getting your dick wet?”

Ron knew from the look in Ann’s eyes that if he said yes, then the redhead would spend the next hour nursing load after load out of his balls. Ron would be more than happy with that situation, but he had another goal right now. Namely, the stacked MILF mewling on his lap.

Ann barely got her fingers out of Maddie’s pussy before Ron slammed his cock inside. True to his style of late, it was brutal and punishing at the start, but exactly whole the MILFs preferred to be fucked.

“F-FUUCCCK!”

The loud wail snapped Helen out of her fuck-addled mind. The first thing she saw was Ron pummeling his hips into the rippling ass cheeks of her new friend, Maddie. Helen was confused about how she had gotten involved, but since Ron was already reshaping her pussy into his personal fuckhole, Helen had no doubt that Maddie would be here to stay.

“SO DEEP! YOU’RE RIPPING ME APART!”

While Maddie screamed deliriously in pleasure, Helen got back on her feet with a wince. Ron did a number on her pussy, which was still somehow leaking his cum. Helen gingerly shuffled behind the fucking couple to see Ann staring at them like a lovesick fool. She ignored the redhead and locked eyes with the swinging balls banging off Maddie’s fat ass cheeks. Helen was going to finally get a taste of those again. Since she had been far too busy getting fucked in every position possible, the first day Ron had sex with her was when Helen had last gotten a taste of Ron’s balls. She was excited to see how they would taste with a different woman’s femcum covering it.

Ron gritted his teeth and clamped his hands down on Maddie’s tiny waist before grunting while trying to fuck her as fast as possible. He had recently learned some things about himself, mainly that he recovered ridiculously fast, and his balls seemed to have a never-ending storage of cum. Ron was going to fill Maddie’s pussy up right now before showing her that it meant nothing when he would keep fucking her through it.

“I-I was wrong. Y-You are definitely—FUCK!” Maddie’s face scrunched up as another orgasm ripped through her body with no mercy. She moaned right in Ron’s face, but that only motivated him to make Maddie’s orgasm longer. If not longer, he wanted to be sure to make another one rip through her right after this one ended.

“Oh my GOD!” Ron’s relentless fucking finally caused Maddie’s pussy to spray out clear femcum and coat his swinging balls in her juices. Maddie shuddered in Ron’s grip before falling towards him. He found himself in the middle of a pair of ample tits that Ron had mistakenly left covered.

“Yes, finally!”

Ron vaguely heard Helen’s voice before he paused fucking Maddie for a second in shock. Helen had decided to slather his balls in her saliva and suck on his cum-filled sack right when it had been doused in Maddie’s juices.

“Fuck!” Ron grunted before restarting the goal of emptying his balls deep inside the newest MILF’s cunt. Helen sucking on his balls and being surrounded by Maddie’s massive tits only helped.

When Ron’s thrusts became erratic, Maddie could feel his cock somehow getting harder inside her though her mind was close to being broken. Helen had both of Ron’s balls in her mouth and was suckling on them softly while her face had become a mess of Maddie’s and Ron’s juices. She could feel Ron’s balls pulsing in her mouth and knew Maddie should soon get a sticky gift delivered deep into her womb.

“Take it!” Ron yelled after pulling back from Maddie’s tits while trying to pound his cock deeper into her, “Take my first load!”

Maddie moaned weakly as she felt Ron’s warm cum fill her pussy before the excess escaped the tight seal on his cock plugging her up. She could vaguely feel someone slurping up the escaping cum but was far too gone to try and find out who. Maddie was surprised that Ron was still going strong, and his cum didn’t seem to stop. She had a distant thought that maybe he had some sort of special powers since this didn’t seem too human. After all, Maddie knew ghosts and the supernatural were real. But that thought was so distant that it quickly disappeared.

Ann had been watching all this with a proud smile as if she was somehow responsible for making Ron into this… stud. In a way, she was. But more importantly, there was a chance now to do one of her favorite new hobbies.

When Ron pumped his hips to send another blast of cum into Maddie’s flooded pussy, Ann took action. The next time Ron lifted the stacked MILF before dropping her back down on his cock, Ann quickly pulled Maddie off Ron’s spurting cock and let her fall on his stomach. Moving fast to avoid wasting too much of his baby batter, Ann plunged her mouth onto his massive cock and skillfully took it down her throat. She swallowed what Ron had to give her while looking into Helen’s surprised eyes. With one woman servicing his balls and another acting as a cumdump, Ron quickly lost track of time as another marathon fuck session was started.