Personal Trainer of MILFs (Kim Possible/The Incredibles)

Summary: Ron turned into a workout nut that was lured into training two women that had the hots for him. When they made a move on him, Ron only put up a token resistance before giving them what they wanted.

Pairings: Ron Stoppable/Ann Possible/Helen Parr

A/N: Poll Winner

Ann sipped on her morning coffee as she snuck glances at the man sitting at her breakfast table. She would have never thought of him as a man before, mainly because this was Kimmie’s best friend, but Ron cut an impressive figure these days.

It was like he just woke up one day and decided to become a workout nut. Ann was honestly impressed that Ron had this kind of dedication in him. Without fail, he went to the gym like clockwork almost every day to do his routines. Just by being around him, Ann felt like she had absorbed the best way to work her body with all the information he spewed out.

All of that was good, of course. Ann always liked people that strived to improve themselves, but a comment from her new neighbor, Helen, made her have a different view of this. You see, Ron wasn’t just a man that worked hard to better himself anymore. He was now a man that Ann was obsessively attracted to.

Damn Helen and her spontaneous comments. Helen had been staring at Ron leaving her house while Ann talked to her. With an absentminded tone, Helen had said, “That boy will become a great lover. He works hard to make himself better, but imagine if that applied in the bedroom. He will probably fuck girls into a coma when he learns what to do.”

Ann couldn’t get that sentence out of her mind, and by the way Helen drooled after Ron, neither could she.

“Bye, Mrs. Dr. P, KP! Gotta go maintain these guns!” Ron walked out while flexing his biceps.

Ann giggled girlishly as she waved him off, making Kim look at her weirdly. She ignored her daughter’s suspicious looks and went next door to talk with her new friend. If Kim didn’t see what was attractive about Ron, it was her problem. Ann was only looking anyway. She had no intention of taking it any further.

Ann was barely able to knock on the door when Helen opened it to invite her in.

“Ann! Come in! I’m just getting ready for my training session.”

Ann couldn’t help but run her eyes over Helen Parr’s body. It was unfair that anyone could have an ass so fat yet keep the rest of their body looking so good. Ann was almost jealous before realizing that she had nothing to be ashamed of. Sure, she didn’t have a fat ass that clapped every time she took a step, but Ann was a Grade-A MILF that looked years younger than her actual age.

“Oh, good! If even you couldn’t help but look at my ass, then my trainer would definitely do the same.”

Ann didn’t flinch at getting caught peeking and asked, “So that’s why you’re walking around in something so obscene? Those yoga pants look like they might get shredded if you bend over a little.”

“That’d be a dream,” Helen giggled, “Ron might fuck me right there if that happens.”

Ann hummed and nodded along in agreement before freezing. “Ron? As in Ron Stoppable?”

“The one and the same,” Helen said with a sly grin, “I convinced him to be my private trainer. The poor boy won’t know what hit him when he sees me.”

Ann gaped at the unfairly gifted MILF and declared, “Then I’m joining in too! There’s no way I’d let you snatch him when I never got a taste.”

If Ann expected a fight, then she would be sorely disappointed. Helen immediately said, “Done! I was hoping you would say that. With the two of us, Ron could never resist the temptation.”

[Break]

Ron was feeling great. He always did after a productive workout, but today had something extra to it. This would be the first time he would be hired as a personal trainer. Ron didn’t really think he would even do this as a side job, but after all the information he gathered on the best way to keep himself healthy, he figured he might as well get paid for it.

Plus, the woman that hired him was somewhat of a secret crush for Ron. Helen Parr had moved into the neighborhood recently, and she had immediately drawn his eye. Ron wished he could say that it was because she was sweet or something about her personality, but the truth was that Helen had one of the best bodies that he had ever seen.

The only one that might match Helen belonged to Ann Possible, and that was something Ron would rather not think about. Besides, those crushes were something Ron could admit he had but would throw away to the back of his mind. Those two women were firmly placed in the ‘impossible’ category and reserved for the guilty wank material.

Ron took a deep breath and knocked on the door, hoping that this would go well so he would get hired again. What he never expected was Ann Possible answering the door.

The first thing Ron did was check and make sure he was at the right house, and the next thing was to try and do the impossible task of looking into Ann’s blue eyes. He unintentionally got a quick look before catching himself, but Ann Possible was wearing something that should have been illegal, at least in Ron’s mind.

Gone was the conservative full-armed shirt and comfortable jeans. In place of those, Ann was wearing skin-tight leggings accompanied by a black sports bra that showed plenty of cleavage. Ron always had trouble keeping his eyes off Ann even when she wasn’t exposing so much of herself, but now it was almost impossible.

“Uh, M-Mrs. Dr. P… What’re you doing here?”

Ann cocked her hip, smiling when Ron’s eyes tracked down before snapping back to look into her eyes, “Helen told me that you’re going to be her trainer. I decided to join in. I hope you don’t mind, Ron.”

“No,” Ron gulped, “Not at all. I hope I don’t disappoint either of you.”

Ann giggled, “Oh, I don’t think you will.”

“Ann!” Helen yelled from inside, “Let Ron in. Don’t hog him to yourself!”

“Well, you heard her,” Ann said before motioning Ron to follow her. She put an extra sway in her walk and stifled a laugh when Ron audibly groaned behind her.

Ann’s heart-shaped ass had the slightest jiggle that could be seen through her leggings. Ron didn’t have a reason to avoid looking since Ann couldn’t see him, so he was practically salivating over the round ass that he was tempted to sink his hands into. Ron wasn’t sure how he would act normal the next time he was at Kim’s house. There was no way he would forget what Ann looked like right now. All he would be doing from now was imagining her perfectly-sized breasts and round ass under that doctor’s coat she wore. That was without mentioning the exposed midriff that didn’t have any blemish Ron could see.

“Let’s get started, Ron! Should we start with some stretches?”

Ron tore his eyes away from Ann’s body with effort and was shocked at the sight of Helen. If Ann was the image of the perfect MILF with model-like looks, then Helen was the fantasy that every horny man dreamed about. She had a massive ass without crossing the line into disgusting, tits that would spill out of his fingers if Ron cupped them, and a face that somehow looked innocent.

“Ron? Are you alright?”

Ron shook himself out of his silence and cleared his throat. “Sorry. Got distracted for a bit. Let’s get started.”

Ann and Helen shared a smile before preparing to torture Ron with temptation.

[Break]

Ron had escaped to get a drink and get himself under control. He had gotten so nervous that his voice actually cracked like he was going through puberty again.

It was honestly one of the hardest things Ron had to do. Guiding Ann and Helen through their warm-ups was a treat to his eyes. But it was also a test of how well he would control his cock. Ron had seen plenty of women in the gym go through the warm-up routine before workouts, and none of them ever came close to making him tent his pants.

The worst part of the warm-ups was when they started doing the squats, pushing out their asses and straining the poor leggings to their limit. Ron was secretly hoping that they would miraculously rip right off their bodies. At that point, Ron knew he had to leave and get himself back together. Not only was it wrong to ogle two women that were just trying to work out, but his cock was also making its presence known. Ron had to leave unless he wanted them to see his cock standing to attention.

That space Ron desperately escaped to get didn’t last long.

“Ron?” Ann called out in concern as she walked into the kitchen, “Are you okay? You ran out of there pretty quickly.”

Ron couldn’t help but glance at Ann’s cleavage before saying, “Just need a minute. I was just thirsty, I guess.”

Ann hummed as she moved closer, “So, I guess I read it wrong.”

“What do you mean?”

Ann was in Ron’s personal space at this point. All he had to do was take a step, and he’d have her curves pressed right against his body.

“Oh, you know. I assumed you ran out because your cock was as hard as steel.”

Ron froze and looked at Ann in shock, unsure if he had imagined what was just said.

Ann didn’t let Ron’s silence bother her. She pushed herself against his body and crushed her breasts on his chest, making the blonde hitch his breath. Ann absentmindedly realized that Ron was taller than her as her hand reached down to cup his cock through his joggers.

“I know what I saw, Ron. There’s no reason to hide it. It’s clearly something you should be proud about.”

Ron was still in shock at the MILF of Middleton massaging his cock through his clothes. By the time he realized what was going on, Ann already had his pants on the floor.

She whispered in shock, “This is amazing!”

Ron’s cock was already large enough that Ann was satisfied with the size, but she now realized that he was a grow-er in addition to being a show-er. Ann was so focused on his cock that she squeaked when a large hand clamped down on her right asscheek. She looked up to see Ron staring at her with hunger in his eyes.

“This isn’t a joke, right?”

Ann raised an eyebrow at Ron before looking pointedly at her hands jacking off his cock and pushed her ass into his grip. “Does it look like it is?”

Ron struggled for a few seconds before saying, “Screw it.”

Ann found herself lifted onto the counter while a tongue was thrust deep into her mouth, exploring it and fighting against her own tongue. At the same time, Ron practically ripped off his pants. Ann’s hands went right back to stroking his cock before Ron pulled away from the kiss with a loud slurp. She was vaguely aware of Helen walking towards them, but Ron quickly brought the focus back on him when he ripped off her sports bra and bit down lightly on her nipple.

“Oh! Careful, Ron! My breasts are sensitive!”

Ron hollowed his cheeks, pulled away to let her nipple pop out of his mouth, and said, “I hope you know I can never look at you the same.”

“I know,” Ann giggled, “But didn’t you always want to do this? Don’t pretend like you didn’t want me before.”

“I did,” Ron admitted, not having a reason to hide it anymore, “But now I know I can have you.”

Ann let go of his cock and said, “And there’s another woman you can have.”

Ron followed Ann’s eyes and saw Helen standing behind them without a stitch of clothing on her body. His eyes stayed on her hips and thick tight before going up to take a long look at her breasts.

“I would usually say my eyes are up here, but you can look as long as you want. And Ann, why didn’t you tell me Ron has a horsecock? I would have made a move to fuck him even earlier.”

Helen didn’t flinch when Ron’s cock spurted a little precum onto her stomach. She idly swiped it with her finger before popping it into her mouth.

“Mmmm, I think I’m going to enjoy this. I’ll give him a go first, Ann. Taking a cock this big might hurt you.”

Ron watched with drool coming out of his mouth as Helen walked to the kitchen table and stuck her fat ass out as an invitation.

“Don’t worry about going slow, big boy. The harder you can fuck me, the better I like it.”

Ron wanted to go right over, but Ann stopped him with a grip on his cock. She was still seated on the counter behind him, and while Ron would love to turn around and fuck the MILF of his dreams, he didn’t want Helen’s invitation to be taken away.

Luckily for Ron, Ann had no plans of stopping him. With her lips right next to his ear, she said, “You better fuck Helen until that fat ass is beaten red. Then I’ll show you just how good I’ll make your cock feel.”

With a new mission instilled in his soul, Ron moved with purpose and stood right behind Helen. She looked over her shoulder and reached back to palm his cock. “I heard all of that, Ann. And you know what? I dare Ron to do it. It’s been a while since a man could fuck me like I deserve.”

Ron heard all of Helen’s boasts, but a large part of him was concerned that he would hurt her. Apparently, Helen could read that on his face.

“Aww, how sweet,” Helen beat his dick on her bouncy asscheeks, “I’m being serious when I say fuck me as hard as you can. Trust me, I’m special that way.” As if to prove that she was serious, Helen bent over the table to present her pussy to Ron.

Ron wasn’t the most experienced with women. Still, he knew that his cock was far too big for anyone without careful preparation. But he supposed that Helen knew her body better. Ron pushed Helen down on the table with a hand on her hack before beating his cock on her fat ass, leaving splatters of precum all over her jiggling cheeks.

True to Helen’s request, the next thing Ron did would make most women scream in pain, but the fat-assed MILF let out a very different reaction.

Ron’s massive cock split Helen’s pussy and forced her womb to open up. His hips met her fat asscheeks with a thunderous crash as his balls slammed into her clit, making Helen choke on her cry as she collapsed onto the table. Ron didn’t stop there, though. He felt how wet her pussy was when he fucked her open, so Ron made a choice to start fucking the MILF as fast as he could.

Helen squealed when she got her pussy hammered into submission, her asscheeks wobbling and bouncing with every slam Ron made into her. Her pussy sprayed out the first of many orgasms Helen would experience as she subtly used her powers to tighten up on Ron’s cock. It was a minor use compared to letting Ron use that monster cock to bust her womb open.

“Yes! Fuck my pussy, Ron! Own it! Break it!”

Ron’s muscles tensed as he gripped Helen’s hips while slamming her onto his cock. The table was shaking under the speed of the fucking Helen was getting as she frantically tried to find some sort of grip to keep herself in place. There was none to find since Ron purposefully used her whole body like a fleshlight, pounding into her tight pussy while pulling her into his punishing thrusts.

“I’m about to cum! You’re too tight!”

Helen gasped when Ron grabbed onto her shoulder-length hair and roughly pulled her off the table to hold her against his chest while he kept pounding her pussy. Ron swallowed her screams and moans by covering her mouth with his before blasting his cum deep inside her womb. Helen moaned into Ron’s lips while she felt her pussy getting filled up. She didn’t try to get away and simply stayed in Ron’s arms until he was finished unloading inside her. It felt like it took minutes until the flow of cum had finally stopped.

Helen moaned in disappointment when Ron pulled out and barely supported herself standing by leaning on the kitchen table. She absentmindedly rubbed her hands over her slightly bulging stomach. Helen could feel every drop of cum bloating her womb. She shuddered with desire at the feeling and turned to eagerly watch how Ann would take that cock.

Ann couldn’t take her eyes off what Ron was doing to Helen. She knew that big dicks were a turn-on to her, but there was no way Ann could have taken Ron’s cock so easily. Helen really did live up to her boasts about how roughly she could take his cock. Ron couldn’t see it since he was busy beating Helen’s ass with his hips, but Ann could see his cock make a bulge in Helen’s stomach every time Ron went balls deep. Even his creampie could be seen visibly from the outside in the form of the slight bump in Helen’s typically flat midriff.

So when Ron walked toward her after giving Helen a dose of his cum, Ann wasn’t sure if she should be excited or scared. In the end, it was a little bit of both as Ron easily lifted her off the counter and held her above his cock. Ann could feel her pussy dripping in arousal as if it was trying to lube up even more before Ron ruined her pussy.

“Go easy on me, Ron,” Ann said as she gripped his strong shoulders. She shuddered at feeling his cockhead trace her pussy lips through her leggings, knowing that it would feel like someone shoved a baseball bat in her tight hole.

Ron held Ann up by her ass, her legs loosely surrounding his body while Ron was perfectly positioned to bury his face in her tits. Before he did that, Ron ripped a hole in Ann’s leggings right where her pussy happened to be and swiped his cock on her opening.

Ann stiffened and opened her mouth in a silent scream when his cockhead burst through the tight seal of her pussy. Even with Ron giving her time to adjust, Ann still felt like there was a fist shoved into her. After a minute or two, Ron gently pulled Ann down his cock while lightly thrusting his hips to get deeper in her tight cunt.

“AHHHHHH! FUCK! SO BIG!”

It looked like Ann got back her voice as she screamed at every inch that Ron fed her pussy. It got to a point where he started to pull out when the screams kept getting louder, but the crazed look Ann gave him discouraged that move.

“DON’T YOU FUCKING TAKE IT OUT!”

With that order, Ron focused on making sure Ann took his cock until his balls were kissing her pussy. The house was filled with Ann’s pleasure-filled screams while Ron grunted every time his cock went ever so deeper inside the redheaded MILF. He alternated between burying his face in her bouncing tits and shutting Ann up by filling her mouth with his tongue. Both options were something Ron was glad to do to prolong the time he was fucking Ann, but Helen had different ideas.

“You’re being too gentle, Ron. You should just shove your cock all the way in this slut. Look at how much she loves what you’re doing already.”

Ron was already lifting Ann off his cock until only his head was inside before slamming her down his shaft. He was even making sharp thrusts into her descending pussy, giving Ann’s pussy a fucking that’ll never leave it the same. Even with all this, Helen was saying Ron was being too soft.

“Let me help you a little.”

Ron absentmindedly wondered what she would do when he froze at feeling a warm mouth on his balls. He looked behind him to see Helen on her knees with her face buried between his legs. Ron couldn’t see anything else, but he could feel her tongue rolling his balls in her mouth.

“Rooon,” Ann whined, “Why’d you stop? You haven’t broken into my womb yet.”

Ron felt like a switch was flipped. He spread his legs to give Helen more room to service his balls and looked into Ann’s blue eyes with determination. Ron turned it up a level with a tight grip on her asscheeks.

“OOOHH FUUCKKK!”

Ann felt like an arm was shoved up her pussy. Ron’s cock reached parts of her that had never been touched before. Every thrust he made was getting deeper and deeper before a loud slap echoed in the kitchen.

Ron stared into Ann’s face as she opened her mouth in a silent scream before his crotch was doused in her orgasm. Helen hummed around his balls when most of Ann’s juices covered her face.

With a new depth discovered in her pussy, Ron didn’t wait for Ann to come back down from her orgasm and went right to fucking her brains out. He lifted Ann all the way up his shaft before slamming her back down to his crotch, making Ann scream loudly as her pussy squirted another orgasm.

Ron wasn’t sure how long he was fucking Ann like this, but by the time he was ready to fill her womb with his cum, Ann’s orgasms were utterly silent. Her face was stuck in a fucked-stupid look, with her tongue hanging out and her eyes rolled up. Ron made one last titanic slam, making Ann squeak, before his balls pulsed in Helen’s mouth and unloaded all of his cum in Ann’s pussy.

Only when every drop was deposited deep inside Ann did Ron pull out. She moaned hoarsely as her pussy was finally given a break from the savage pounding it had been getting. Ron gently put Ann down on a chair after Helen finally stopped sucking on his balls.

When he saw Helen’s face for the first time since she started giving his sack a tongue bath, Ron gaped at the mess he saw. It was like Helen had stood in the rain for an hour if not for the cum that must have dripped out of Ann’s pussy and landed on her face.

Helen idly swiped up all the juices on her face and sucked them off her fingers. “Ann’s really a squirter, huh? How about we go another round? I could use some of what Ann just got.”

Ron gulped as his cock started to come back to life.