Jake's Personal Trainer

Author's Note:

This is my first story so I'd appreciate some feedback if it's not too much trouble. It's a pretty slow buildup, so if you just want the stroke material it's about halfway through. Enjoy!

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Jake's personal trainer was willing to go to any extreme to get him in shape.

Well, "personal trainer" doesn't really give the full picture. Jen was a childhood friend of his. See, they grew up in a rinky-dink town out in Minnesota where if you couldn't throw a ball, you were just wasting space.

Jake was that waste of space.

They didn't know each other well back then, but practically everyone knew who she was. He had never really talked to her, but had always gone to every one of her games. Back then she was the tomboyish postergirl of every team that she could get on, and she could get on 'em all. Basketball, softball, volleyball, she was even the first girl on the wrestling team (making for some incredibly awkward matches). She was always first pick in P.E., voted MVP every year. But where she excelled the most was soccer. She was the best striker their school had ever seen. Games started to draw in larger and larger crowds, just to see her play.

Of course, he wasn't interested in sports in the least.

Even back then, her long, muscled legs were more powerful than anyone else on the field. She had thighs that could crush a watermelon, thicker around than both legs of most of the petite girls she intimidated. Literally. On a dare at one of the few parties he actually got to go to my senior year, she put a watermelon in between her legs and crushed it without breaking a sweat.

He couldn't tell you how many sticky sheets he woke up to after that.

But that was all so long ago. Five years later, a lot had changed. They all graduated, he moved halfway across the country, got three odd inches taller, and left everything behind. He finally got to a place where he could really thrive and got his degree in business. He finally found himself in the oh-so-glamorous field of Data Management at an insurance firm his first year out of university. He had moved past where he came from, hadn't thought of high school in years. It seemed only one thing stayed the same after all these years: he was a skinny little shit.

Turns out hours of intensive studying for 4 years followed by earning a desk job didn't foster the best body. But with his new salary, he could finally afford to go to the gym. Better yet, he could afford to get a trainer (lord knows he needed it). he had already called the gym to schedule ahead and book a trainer for the next year. He figured if he committed this much money at the start of the new year, there's no way he'd bitch out. The plan was easy: he got two hours for lunch so he'd work out the first hour, and eat the second. Simple.

That fateful day, he did his normal routine—with the addition of bringing a change of clothes. He needed something he could really move in, and he detested staying in sweaty clothes. Every gym class in high school he changed----down to underwear and socks----and this was no different. He threw a t-shirt, sneakers that hadn't seen the light of day in almost a decade, some old basketball shorts, and spare sock and underwear into his knapsack. He put a suit on over his pale lithe frame and headed off. When he got to work, he did the same monotonous shit he always does, but instead of going to the cheapest restaurant available with some work 'friends' at the start of our lunch, he walked on down to the building he never thought he'd enter: Fitness Palace.

The unsurprisingly fit receptionist looked up from her desktop and gave him a million dollar smile as he walked through the door. She was a few years older than Jake, about 30 maybe. Big green eyes, dark brown hair met with pale skin on her petite frame. Had a real manic-pixie-dream girl vibe going on. That is to say, adorable, but so, so far out of his league.

"How can I help you today sir?"

"I'm here for an appointment" he said in the absolute least authoritative voice these walls have ever heard.

"Perfect!" She responded in an all-too-cheery tone. "And who will you be seeing today sweetie?"

He looked down with a blush. "I don't know actually. I just booked a time and a room, someone said on the phone that schedules are pretty hectic right now cause of the new year so I wouldn't be able to get someone specific for a while"

"Oh I getcha" She replied with a wink. "Don't want all these New Years Resolution type people to see your journey. I completely understand! You'll be just up the stairs in private room 204. Enjoy your time!"

He gave a curt nod, the type you give when you're just too damn awkward to give a real answer. He bounded up the stairs, wondering what kind of roided-out jock would be torturing him for money for the next 6 months. He walked in front of the door, put his hand on the handle and took a deep breath in.

Of course you know who he really found.

Jen was doing her warm up stretches as he walked in. In her light blue sports bra and grey yoga pants, she was ready for the first private appointment of the new year. Hopefully she'd be able to resist doing what she had to the *other* clients. It seldom worked out alright and more often than not, chased customers away. She shook the thought from her head and continued warming up. Conveniently, as if this were a set up for porn, she was touching her toes, facing away from the door when Jake built up the courage to open it. For the first time in 5 years, Jake once again got a look at Jen's famously perfect ass--even if he didn't know it yet. Things had changed, true--but her yoga pants framed ass was still as impressive as it had been when they were eighteen. Jen began to speak from this position, slowly coming to a stand as she spoke.

"Welcome to Fitness Palace, I'll be your instructor, my name is--"

Jen was left speechless as she turned around to his familiarly geeky frame. She too thought she had left everything about her small town behind, and yet here was a living reminder, in the flesh. Jake's face was mirroring hers, taken aback by the sight of this beauty in front of him once again. He was just hoping the trainer would be a girl, let alone the girl he had fantasized about fuckking in high school. She didn't look all too different. She had grown her hair out a bit more, but she still kept it up in a ponytail. Her brown eyes still had that intensity about them, like she could see right through you but was kind enough to do it discreetly. Her lithe young arms were now rock solid, putting most men's biceps to shame. Somehow her tits seemed to have gotten even bigger. Jack noticed of course, but tried his damndest to keep eye contact with her deep stare.

"Don't I know you? John? Jack?" Jen said, wracking her mind.

"Jake actually" He said with a gulp. "We had English together senior year, P.E. too for a while. I was the one in the back getting constantly and mercilessly hit."

She let out a giggle. "Ah yeah, I remember now. Jake, of course. You were pretty funny then too. I remember you were always quick with the quips in Mr. Alban's class. He could've killed you, I swear." Was that a hint of flirtation he heard in her voice?

The pair laughed as Jen went on reminiscing. "And I remember you went to just about every one of my games, didn't you? I saw you in the stands. My little cheerleader."

Jake's cheeks tinted pink. "I didn't know you had even seen me. Besides, I just really liked going to games, school spirit and all that" He mumbled.

Jen looked her old classmate up and down, assessing him. If Jake didn't know any better, he'd say she was checking him out. "Yeah, I'm sure you were really interested in sports."

His eyes were glued to the floor and his cheeks burned an even deeper shade of red. Her tone was light, enough to tell him he wasn't mad, but it left him flustered nonetheless. He cleared his throat and met her eyes once more. "Could we get started?"

"Alright hun" Jen said with a grin. "I was thinking we could start equipment free, build up endurance before we get to really bulking you up"

Jack wordlessly nodded and followed behind her, staring at her massive ass as she led him deeper into the room. The sway of her hips was tantalizing, and the yoga pants made her ass look better than any insta-model he'd ever seen. Tight enough to leave little to the imagination, and the color let him appreciate each step. She turned back, catching him staring, but only seemed to smile wider.

"Could you close the door behind you for me too hun?"

Jake once again nodded, turning to obey what he's been told.

"I think we'll start out with some squats" Jen said. The two stood side by side, starting their very first work out. And Jake was already fucking it up.

"Tsk," Jen turned her head in disapproval. "You're doing it all wrong. Not getting low enough, your legs are too close together."

She stepped out in front of him. "Let me demonstrate them for you, form is everything if you really want to get in shape. Stay behind me and watch my stance and how low I get, alright?"

"Yes ma'am" Jake responded, already staring at her ass.

Jen felt the familiar tingle from hearing a man say those words to her once again. Shaking the thought from her head once more, she went deep into the squat, down and up, for 20 reps. Jake looked on, feeling his cock harden in his shorts. Back when he used to watch her games, he was always sitting, his erection easy to hide. Now it was all out in the open, and while he was by no means huge, there was no hiding it. Succumbing to his fate, he stared on. 'In for a penny, in for a pound' he thought to himself.

She finished off her reps and turned around to Jake, immediately seeing the tent he had pitched.

"Oh!"

"I'm so so-"

"No, no, don't be. All this exercise gets adrenaline going, it's a natural response. And I won't lie, you're not the first man to have that response to this". She teased as she turned her ass towards him and jiggled it a little. Jake's eyes widened and his cock throbbed, as he could clearly feel, and as she could clearly see.

"And at least you're not among the smallest" She finished off. "Alright enough dicking around. Let's get you in shape!"

The rest of their workout was rather uniform. Jake still couldn't do his squats right, but he was at least improving. Jen had him do some push ups as well, and eventually got him onto one of the two treadmills in the corner as she ran alongside him. By the time their hour was over, both of them were covered in a fine sheen of sweat. Only difference is, Jen had a slight glow about her, her breasts looking even more phenomenal with the slight glisten. Jake on the other hand, had sweat through his shirt and was breathing like a dying walrus.

"For the first time, it's not bad!" Jen assured him as she packed up her things. "And we'll pick up more tomorrow"

"Oh!" Jake said in surprise. "I get to have you every day? I thought the schedule was too hectic."

"For an old friend?" Jen responded with a smile. "I'll make time."

Jake thanked her and considered inviting her to lunch. After all, she did even more work than he did and he still had an hour left for lunch.

"H-Hey J-Jen?" He started.

"Yeah hun?" She asked back, looking up at him with those intense eyes once again. He looked down at this much shorter woman, someone who would normally be so unintimidating. But he knew her strength. He liked her strength. Probably a little too much.

'Just ask her'

"S-See you tomorrow."

'Pussy.'

"I'll see you then cutie" She said with a wink as she walked out of the room, leaving him only with the sight of her glorious ass sauntering away, and the smell of her sweat and body wash.

Jake sighed as he went to shower the sweat and embarrassment off. Luckily, the showers upstairs were reserved for after private lessons, and his were the only ones scheduled at the time. He got them all to himself. He thought of Jen as he wrapped his hand around his cock, jerking up and down slowly as he thought of her bending over, going faster and faster as he thought of her calling him pet names. He was sent over the edge by the memory of her teasing him with her ass cheeks.

'God I want those on my face' he thought as he came all over the shower floor. He watched the water carry the evidence away, grabbed his clean work clothes, and set off to go eat his lunch.

Alone.

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Jake woke up sore. His groggy mind couldn't find the reason as to why.

'Oh yeah' he thought. 'The girl of my fucking dreams walked right into my life yesterday.'

He looked down to find his cock stretching the blanket up. 'I feel like I'm in high school again.'

He thought back to yesterday. He was positive she was teasing him, but doubly sure that he didn't have the confidence or control to do the same in return. 'At least I get to be around her again.'

For the second time in as many days, he thought of his old high school crush as he jerked off. His moans weren't as manly as he'd like to admit, and grew only higher when he thought of her powerful legs and absolute control. With a high whimper, he came all over himself. With a sigh, he got up, careful not to spill any cum onto his bed or the floor. He took his morning shower and watched globs of his cum wash down the drain, careful not to leave any on himself. He got ready for work, grabbed his gym clothes and was off once again.After an unremarkable morning, more time with Jen was welcome. He walked through the door.

"Oh hey Jake" She said without looking up from her phone.

This time, she leaned against the wall in a black sports bra and short, tight spandex. "I was thinking today we'd work on your core and do some cardio. Planking and sit ups for the first half, and we can take a few laps around the block for the second"

The effect of seeing her in such a revealing outfit was immediate, his cock growing down his leg and pushing his gym shorts out. This can't be happening. He was absolutely mortified. "Y-Yeah" He stuttered. "Okay"

He tried to turn his body away to hide his embarrassment, but Jen could clearly see what was tucked away in his shorts. "Seems you have that reaction a lot around me." She laughed. "I take it you like the spanex?"

"Y-yeah" He blushed.

"I'm glad cutie" She teased while running her hands down her muscled thighs. "But let's get to work, looks like you could use a distraction"

Jake nodded in agreement. "Planking right?"

"Right." Jen answered. "Now get on the ground, holding yourself up with your elbows"

Jake did just that.

"You follow instructions well!" She said. "I like that when I train someone"

Jake felt his face flush, something that had happened all too often these days.

"Alright now when I say go, you'll lift those hips and keep your position for one minute. Okay?"

"Alright"

"aaaaaand...Go."

Jake started out well, as most do, but soon grew wobbly. Jen could see that his resolve was thinning, and he was practically trembling by the end of those 60 short seconds.

"Alright sweetie, that's one minute"

Jake let himself fall to the floor, huffing. Normally he would have felt embarrassed that he did so poorly, but he was all too focused on the pain to really care. Jen looked on fondly, proud that he kept up his hard work. Too many of her clients wanted results, but didn't work for it. Jake was wonderfully...obedient. She let Jake rest for another minute, and decided it was time to get back to work.

"Alright, time for sit ups"

They got into place, Jake on his back with his legs tucked in, Jen at his feet holding his legs down. "You're going to do 50 reps for me, okay hun?"

"50!?"

"Yes, 50. Stop complaining hun, it'll all be worth it"

Jake begrudgingly began the work out. He started to struggle not 10 reps in, but then began to notice he could see down Jen's sports bra whenever he reached the crest of a rep. He could feel a twinge of guilt in the back of his mind for it, but that mysteriously disappeared the longer he looked. He looked up to see if she noticed, and her eyes were trained on his. He blushed--not that you could tell as his face was already red from exertion. Why didn't she say anything if she clearly saw him looking? After 20 reps--exactly 20 reps Jake thought--Jen leaned in deeper, giving him an even better look at her tits.

'Does she want me to look?' He stopped himself from doing so, but another 10 reps in, she leaned in even lower. Now, Jen was, to say the least, blessed. Anyone would be staring at her tits from this angle. 'Fuck it, I gotta look.' He sped through the next 20 reps, just to get more and more looks at her. Though he definitely wasn't going to meet her eyes again, he could feel her stare burrowing into him. Not disapproval, just that intensity she always carries. The power. He finished off the last rep, getting one last good look down her bra, and flopping to the floor.

"See!" Jen said with a gleam in her eye. "I knew you could do it. All you needed was a little extra...motivation"

She winked at him. So she DID mean it.

"Alright hun, you get 5 minutes to rest and hydrate, and then we're off for our run!"

Dear Lord.

The pair mulled around for a few minutes, letting Jake catch his breath and curb the ache in his abdomen. Together, they walked out of the confines of their private room, down the stairs, and out the door.

"Alright Jake, you're a beginner so we're taking it light. We're just gonna run a mile today, no where near top speed. Light and easy"

Jake was uneasy, but knew he had no choice. They started out at a jog side by side, but half a mile in, Jake's fatigue started setting in, and he started to fall behind. Jen slowed them to a stop, momentarily disappointed with their lack of progress. Jake caught his breath but saw Jen's face light up as an idea entered her head.

"Alright hun, new idea. I'll run out ahead in front of you, and you follow me. It'll give you some of that...inspiration that seems to work so well on you."

Jake's now customary blush creeped as he tried to defend himself, but Jen was already off. He started off after her, immediately noticing her legendary ass. The ass he dreamed about for 4 long years. Her spandex had ridden up. It was already clear enough to see her ass through them, but she had begun to peek out of the bottom too. She had worked hard to sculpt her ass, but was gifted naturally. Having never gotten plastic surgery, and putting in constant work, her ass was even more mesmerizing than it had been those years ago. He saw other men turn their heads as she jogged by--and who could resist? But Jake didn't have to worry about their passing glances when for the next half mile, he could stare all he wanted. Soon enough, he ran into a problem. You ever run with a boner?

It sucks.

He jogged all the way back to the gym, cock swinging about, until he finally, mercifully got to stop. Jen turned around to face him.

"I see you enjoyed our run!" She laughed. "Let's get you inside before someone else tries to see the roll of quarters you snuck in on our run"

She looked down at his shorts again, staring for a couple beats longer than needed. "More like a roll of dollar coins really" She finished as she led him back into the gym.

With flushed face, practically his new signature shade, he let her lead him back to their private room. Jake's cock had yet to even stop throbbing. They were both glistening with sweat, once again, doing nothing to help his problem. He thought she looked perfect just like was, but the moment was soon over.