Coaching A Pretty Boy

By DMears
published June 26, 2019

Coach Myers has just been suspended for harrassing the cheerleaders and isn’t too keen on changing his ways. Well, Chase is about to help him see the light.

Author’s Note: Thanks for all the feedback on my stories so far. If you want to see more of my content please join my Patreon where I’ll be posting more stuff like this on a more regular basis pretty soon.

Until then, enjoy this little tease of what’s to come! ;-)

Coach Henry Myers is in a bit of a pickle. He’s been coaching football at Ohio State for well over 30 years but that legacy is jeopardy after finding himself in some trouble. He was recently suspended due to some allegations made against him by some cheerleaders that he constantly harassed them, and with this being a post-metoo world, the school had to save face. He was promised it was only for a short time and he’d be back soon (his record winning games is nothing to be trifled with) so of course the school still wants him. Just need to wait out the storm. Until then, he’s definitely been finding himself feeling pretty bored. “Maybe I should go to a bar” he’d think to himself. Of course as soon as that thought would come he’d immediately drive it out, can’t risk being caught picking up more college girls this soon after his suspension. So he’d usually just peruse the Tinder app, hoping to find someone who could fulfill his needs. Most of the time it’s a bust but tonight was a little different. After a lengthy search he came across this one picture of a gorgeous woman, mid-thirties, who looked like one of the many college girls he’d usually harass at school. He immediately got hard staring at her breasts, her long hair flung just the right way across her shoulder, in fact, she looked like a model. Taking his chance, hoping they’d match, he swiped right and to his excitement, she matched with him! He immediately messaged her.

“Hey baby, how’s it going tonight?” He typed.

Within seconds. “Ugh, can’t complain I guess. Just reaaaaaaalllllly bored. LOL”

“Same here, was actually hoping to get a little action tonight. You down?” He anxiously awaited her response. After a tense moment thinking she might’ve turned away from it, she texts back.

“Haha, sure there daddy. Only if you wear that cute uniform in your profile pic. Here’s my address. Be here in ten or I start without you. ;-)” She cheekily responded.

Myers couldn’t help but get hard immediately at the sight of her message. Once he got her address he immediately put on his coach’s uniform, along with his whistle, already imagining all the fun they’ll have with that. Made some excuse to his wife about meeting some of the boys at the bar and was on his way. In the car he couldn’t help but think about everything he’ll do to her. Myers has always been into some bondage type stuff: hog-tying, ball-gags, leather harnesses, you name it he tried it. Never on himself of course, he was the one performing these fun tricks on all his conquests.

At 60 years old, he wasn’t too bad looking. One look at him and the gray in his hair, you could determine he was once a silver fox who got a tad too wrinkled. Even more handsome in his college days most likely, he was quite the football player. Built like a tank and even went to play for the NFL at one point. Those were the days.

After being lost for a minute in his glory days, he startles at the sound of the GPS announcing he has arrived. Looking out his window at his destination, he was sorta surprised the house was this nice. It was big enough to the point it must have it’s own staff to run it, especially considering how nice it all looks.

“I’m here.” He responds.

“Awesome! Come on in, the front door is open. I’m getting something nice on, I’m sure you’ll enjoy it. ;-)”

This should’ve been a red flag, for most people it would be, but Myers was so horny he didn’t care. Instead he makes it inside and can’t help but gawk at the beautiful living room he’s found himself in. So big and full of gorgeous furniture. “Wonder what this woman does to earn all of this? Maybe she has a husband away or something, no way a woman would make this much money.” His misogynistic mind can’t help but think.

He sits down on a couch just waiting for her to arrive. “It must be all the men she has in here. That’s it. She’s a whore looking for her sugar daddy. Who knows, maybe if I like her I’ll throw her a bone. Maybe a real bone too.” He laughs to himself the funny thought.

“What’s so funny?” a deep voice says behind him.

Startled by the noise, Myers turns around to see, not the beautiful woman he was promised but a handsome, muscled, slightly hairy man in his mid-thirties instead. He’s wearing an unzipped jacket with a gold chain and some tight jeans that don’t leave a lot to the imagination.

Myers can only gawk at this sight. Definitely not what he was expecting, meanwhile, the man is just standing there, leaning against the wall waiting for a response. “Hello, what’s so funny?” the man said again.

“Umm, where’s Chelsea?” Myers finally got out.

“Chelsea?” the man said.

“Yes, Chelsea, the woman I’m meeting here. Who are you by the way, her security guard or something.?” Myers warily responded.

“Oh no, sorry about that. Just figured you wouldn’t come if you knew who I was. Name’s Chase. What’s yours baby?” The man, apparently named Chase, asked.

Myers is stunned for a second, processing what this means. Then…

“FUCK YOU! Do I look like a faggot?! Huh?!” Myers gets up to make his way out. “This is ridic-”

Chase puts a hand on Myers chest. Myers is an impressive 6’5, the same height as this man, but the man is clearly much stronger than he is. Still, Myers isn’t scared.

“Get your hand off-”

“I asked you a question. What’s… your… name?” Chase said very slowly.

Something about the way Chase said that made Myers freeze in that moment. He felt strangely compelled to answer the behemoth in front of him.

“He-Henry.” Myers meekly sputtered. Strange, he’s never felt this self-conscious before. Chase smiled.

“Good, let’s go back to the couch Henry.”

Chase slowly led Henry back to the couch and sat him down. Henry had no choice but to comply. It was strange, all of his willpower was sapped from him, fully in the hands of this man no matter how much his inner voice told him to run away. Chase, a tad rough, pushes Henry back onto to the couch. The man sat on the table in front of him and just stared at his new prey, licking his lips at the idea of what’s to come.

“So Henry, tell me about yourself. What do you do?” Chase said, leaning back on the table, flaunting his gorgeous abs. Henry just sputters again.

“I… I ugh, coach. How did you do-”

“That doesn’t seem right. How could you coach?”

“I do though.”

“So what you did to the cheerleaders, that was coaching?” Chase asks with a head tilt.

“They wanted it. I know it. And even if they didn’t, I wanted it. It’s only right.” Henry has no idea why he’s saying this.

“I see. Can you say the same for Gabrielle Houston?”

“Who is that?” Henry asks.

“Wow, can’t even remember the names of the girls you’ve traumatized. She is my sister. My little sister who lost her place on the cheerleading team because she dared to speak up against you. Did she want it?” Chase asks with as much venom as possible.

“I… uhh.” Henry stutters.

Chase just gets up and stands right in front of Henry. For a second he caresses the man’s cheek and puts a hand under his chin. Sweat is pouring down from Henry’s face now, the fear of what’s to come filling his every bone. “Do you want this, Henry?”

“N-nno. I don’t. Please let me go.” Henry asks, begging for the first time in his life.

“Oh, well something tells me you do want it. And if you don’t now, you will later.” Chase reaches down, getting his face closer and closer to Henry until they’re almost touching. Henry closes his eyes, expecting the worst, but, Chase suddenly starts moving away. Instead he’s just taking off the whistle around Henry’s neck. Chase takes a few steps back. Henry sighs some relief but the fun is just getting started.

With a smile, “Henry, do you mind standing up?” Henry does. They are exactly the same height. Then…

Chase blows the whistle! A draft of air blows through the living room. It’s incredibly chilly, Henry’s legs feel almost frozen from it. When he looks down, he finds his pants are gone! Replaced with black running shorts (a slight movement reveals to Henry his underwear is completely gone as well), his dress shoes replaced with tennis shoes. He looks back at Chase. “What the fu-”

Another blow of the whistle, another draft. This time, Henry’s long-sleeve polo and undershirt are completely gone, exposing his older body to the world. His watch and wedding ring completely disappear too, leaving him with just the shorts and shoes on. “Dang old man, didn’t keep that body in too much shape did ya?” Chase said while twisting one of Henry’s nipples. This elicits a slight gasp out of him, bot because of pleasure but because of pain. “Don’t worry, you’ll like it soon enough.”

“Look, whatever you’re doing just-”

Another blow of the whistle and the biggest change yet happens. Henry can feel his body quickly moving through time, getting younger and younger by the second. First his hair turns from it’s gray color to a bright black. His sagging muscles get bigger and bigger until they are the size of a football, his stomach becomes a glorious eight-pack again. His pecs become round and sharp. All the wrinkles in his face disappear as some black stubble appears on his face. After a moment, things calm down, giving Henry a chance to check out what happened. He feels his new, younger body and looks in a mirror on the other side of the living room, he looks no older than 22 years old. After feeling his face, he can’t help but get a little turned on by the image of his hot, young body. Strange, he’s never been turned on by handsome men before.

“What the fuck just happened to me man?” Henry asks in his younger voice. He stares at Chase for a second, still the same height, but he’s sure he could take him on now. He’s definitely stronger than Chase at this point.

“Wow, you were a real stunner back in the day Henry. Tell me, get a lot of girls looking like this.” Chase says fondling the man’s crotch, causing him to gasp, this time from pleasure.

“Uhh, yeah dude. Got a lot of girls. Won’t believe how many. Oh fuck, dude, what are you doing to me? I’ve never felt like this before?” Henry asks, closing his eyes for a moment.

“Liking this Xavier?” Chase asks.

“Umm, my name’s not Xavier.” Henry says, trying really hard to stay all together.

“Really? You look like such a Xavier though. Don’t you like that name more?” Chase says squeezing his bulge, eliciting a gasp from him. Fuck! Henry, or Xavier thinks. He’s not really sure who he is now. It’s okay. I’m bigger than he is. If I can just break away for a second, I can pummel this dude to the ground and- his thought is interrupted by the sound of the whistle yet again.

Xavier feels the effects take hold of him. His body getting a little bit younger, him losing a couple inches but not much as he regresses back to 18. Aside from losing the inches, not much has changed except for his face and body being completely hairless now. For a wild second, he thought he could still get away but then more changes happen. He looks in the mirror in time to watch his body lose nearly all of it’s muscle. Sure he still looks toned, but it’s more for show than anything else. He shrinks in height until he’s no more than 5’6, almost a foot shorter than the man in front of him. He watches his face lose some of it’s masculine features, becoming rounder, cuter, innocent; lips get plumper, perfect for kissing and so much more. His hair grows longer, getting wavier and wavier. Finally, he lets out a moan of pain and pleasure as he feels a piercing appear on both his ears. The final thing to change were his shorts into jeans, with his underwear peaking through. Xavier can’t help but stare at his reflection, his boner fully visible and throbbing now. As he catches his breath, he looks up at Chase, who’s smiling down at him.

Putting a hand on the boy’s cheek, Chase says: “Look at you, so precious. Don’t you feel better now Xavier?”

Xavier has to try with all his might not to say so. But the truth it, he feels amazing, he feels ready for so much right now.

“I asked you a question Xavier. Do I have to ask again? Remember the punishment?” Chase teases.

Punishment? What punishment? Xavier holds his tongue as best he can. Chase sighs. “Okay then, let’s go.” He grabs Xavier by the arm and drags him to his room and tosses the boy on the bed. Xavier lands with a high-pitched grunt. He watches as Chase goes through a drawer, looking for something. This is it, his chance to escape, sure he’s shorter now but he’s positive he’s still fast. If he makes a break for it he should be good. But there’s an issue, a part of him is hesitating. Shouldn’t make Chase mad again. A part of him wonder. He quickly shakes his head of that and decides he has no choice. No way he’s gonna be some fairy boy for this man. With a grunt, Xavier bolts off the bed for the door but before he has a chance to make it, Chase is already on him, grabbing him and carrying him back to the bed with ease.

“Oh there boy! Where you think you’re going?”

“STOP IT! JUST LEAVE ME ALONE!” Xavier yells in his much higher voice, definitely much higher than when he was 18 last time in his life.

Chase just throws Xavier on the bed and pins him down. He holds Xaviers arms out and feels the his struggles underneath his body. With every struggle, he can feel Xavier grind their dicks together more and more. Before Xavier knows it, his struggling is looking a lot more grinding.

“Shhhh, that’s right Xavier. Just let it out.” He calmly says.

“Shut up! My name is Xavier not…” He goes quiet and stops moving for a second. What was his name? Xavier? That doesn’t feel right but it’s the only name he knows. The more he thinks of it, the more he realizes Xavier does sound right. Yeah, his name is Xavier.

“How old are you?” Chase quietly asks.

“I’m… I’m…” He thinks for a second. 60 is a number that pops into his head but that can’t be right. He looks in the mirror and sees his body. So handsome. So ready to be fucked. So young. There’s no way he’s that old. After a moment he realizes…

“18, I’m 18.” Yeah that feels right.

Chase smiles and grinds a little bit against the teen’s groin, causing him to groan with pleasure. “Do you like this Xavier?”

Of course he does, he’s loved every second of this. He’s so happy Mr. Chase took him in. He’s so happy he decided to be his daddy. Xavier just licks his lips and says…

“Yes sir. I like this a lot.”

“Well if that’s so, you shouldn’t have tried to run away from me.”

“I’m sorry sir, I don’t know what came over me.”

“I mean if you don’t want this then you’re free to go.”

“No! Please sir don’t make me go. I want this. I really really do. I wanna stay here with you.” Xavier innocently responds.

“Okay boy, well, you know I still have to punish you for what you did. Understand?”

Xavier nods. “Yes sir. I’m sorry. I’m ready for my punishment.”

With that, Chase immediately went in for a kiss, taking the teen’s mouth for his own. The smacking of lips the only thing heard as Chase violently grinds into him, with every thrust, Xavier grunts a sound of pure joy. Eventually, Chase lifts Xavier’s legs up and dry humps the teen’s butt, both of them getting harder and harder by the second. After a minute of doing this, Chase powerfully rips off Xavier’s jeans and underwear in one go, leaving him completely naked. Xavier reaches to jerk himself off but Chase grabs his hand and pulls it away.

“Nu uh, no jerking for you today. You’ve been very bad. Time for your punishment.” Xavier just moans as he says that.

Chase goes to the drawer and grabs what he was looking for. Walking back to the bed, he sees Xavier has already started jerking himself off. He immediately whips Xavier on the hand with a flogger, causing a yelp from him.

“Such a bad pup, gone for one second and already playing with yourself.” Chase tsks.

“I’m sorry sir. I can’t help it.” Xavier moans back.

“Well it’s time to teach you. Ready to learn?”

“Yes, please teach me. I’m ready. I’m ready.” Xavier moans like the slut he’s turning into.

Chase grabs the boy and violently turns him over, holding his hands behind his back. His butt, so plump and round, exposed to the world, he starts whipping it as hard as he can. A whip! Xavier gasps. A whip! He gasps again. Another whip! He gasps again. The red marks on his butt, plain as day. Chase leans down, pushing his arms up his back, eliciting pained sounds from him, and whispers right in his ear. “Had enough punishment?”

A part of Xavier wants to say yes, but another part…

“No sir. I need more. I’ve been very bad. Please, punish me.”

“That’s what I thought. Oh and one more thing…”

Chase puts a ball-gag around Xavier’s mouth, causing him to moan into it. God he loves the ball-gag. “I don’t wanna hear another sound out of you while I’m giving you your punishment.”

Chase, holding his arms down with one hand (he’s that tiny now), reaches for some rope he brought over and bind his hands together behind his back. Once bound, Chase keeps him bent over, legs spread wide so there is a clear view of his asshole, and starts whipping him. With every whip, Xavier grunts from pain, but can’t help but love the feeling. He loves being taken advantage of. He loves every second of it. He remembers how all of the guys on the football team in high school would take their turns on him, pounding away all worries he had in the world, whipping him black and blue, just like he liked. After all, he was a bad boy, and knew he had to be punished.

Eventually, Chase stops whipping him, and, once his ass is sufficiently reddened, puts down the whip and leans close to the tied boy and takes off the ball-gag. With a gasp, Xavier takes in some deep breaths.

Next to his ear. “Do you want me inside you boy?”

“Yes sir.”

“You sure?”

“Please sir, do whatever you want.”

Chase smiles and grabs the whistle from earlier. He puts it in Xavier’s mouth, causing him to moan once again, he loves having stuff in his mouth.

“I’ll give you control this time. Every time you want a thrust. Just blow on this whistle. Understood?” he breathes in Xavier’s ear. Xavier nods. “Good boy.”

He kisses his ear, right where his piercing is. Xavier moans. He continues kissing down his back until he gets to his butt. Kissing all over each cheek, taking a few bite out of it too, causing Xavier to writhe a little and blow on the whistle some.

“Calm down boy. Let’s take our time. We have all the time in the world.”

Xavier doesn’t care, he’s impatient, he wants it now! So, Chase gives him his wish, with one fell swoop, he enters Xavier, all the way through. The boy moans and writhes in some pain but mostly pleasure. Xavier blows on the whistle. Chase gives him a thrust. It isn’t enough. Xavier blows on the whistle again. Chase thrusts again. Still not enough. Xavier blows on the whistle as long as he can, causing Chase to pound away at him, making this boy even rawer than he already was from the whipping he got. With every thrust, Xavier feels an old part of him chip away. Whoever he was before this night slowly disappears, making it’s way into his balls as his dick, with the combination of grinding against the bed and Chase’s pounding, ends up cumming everything out right there. Chase cums at the same time, both of them moaning and grunting from the release they both enjoyed.

After a moment of them coming down from their orgasmic high, Chase steps away while Xavier lays his head down, whistle still in his mouth. He stares at the naked form of Chase, his wonderful daddy, and already feels himself getting hard. Chase looks at him and smiles, he takes the whistle from the boy and leans close to him.

“How’d you like that boy? Feel like you were punished enough tonight?”

“I-I think so sir. I’m so sorry I’ve been bad. I won’t do it again. I promise.” Xavier breathes.

“Ahh, but where’s the fun in that?” Chase slaps a hand on Xavier’s butt, making him gasp, and rubs it. “You have such a nice butt. Remember to keep it in shape for me.”

“Yes sir.”

“After all, what’s your job again Xavier?” He asks caressing his face.

“I stay your wonderful pup. That’s really all I can do. Not good at much else.”

Chase tenderly kisses him. “It’s good enough for me.” Xavier smiles.

Chase unties Xavier from his binds, allowing him to sit up. While Xavier nurses the rope burn on his wrists, Chase gets on top of him and leans down for a kiss. The two kiss for what feels like an eternity. Xavier just wishes he could stay in this moment forever. Once it’s done, Chase gives him the most affectionate stare, like a proud parent of their child. Xavier just wants to make his daddy happy. After a moment they both crawl into bed, still naked. Xavier curls up to Chase, laying his head on his daddy’s chest, completely content with the life he has.

“Good night daddy.” Xavier smiles.

“Good night my little pup.”

Chase gives him an affectionate kiss as they drift off to sleep. Xavier smiles one last time, already growing a little hard at the thought of what happens next time he misbehaves. Thank goodness he has Chase to watch over him, no way he’d survive on his own.

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