Measuring Up

By Scotty the Body - scotty.the.body@hotmail.com
published June 11, 2021
3562 words
Summary

Chris needs a new suit for the upcoming reunion. Thankfully, Ricky is on very friendly terms with a local tailor, Art, who can meet their needs - sartorial or otherwise - on short notice.

“Make sure to keep hydrated, dear.” Ricky passed Chris a bottle of his sport drink solution, his third of the day. “We don’t want your measurements at the tailor to be off, do we?”

Chris eagerly reached for his drink, nodding in agreement. He chugged it down without stopping to take a breath. He sighed with contentment and looked blankly out the window, watching the sights of his hometown pass him by. As Ricky turned onto the main street, he pulled over and parked outside Art’s tailor shop.

“I can’t wait for you to see Art again. I don’t know how he does it, but the man looks better and better every year.” Ricky pulled Chris in for a kiss by the neck of his tank top. “I’m sure he’ll be thrilled by how you’ve turned out, too. It won’t be hard for him to make you look great. Ready to go in?”

Chris smiled vacantly, happy with the compliments he was getting from Ricky. “Yep, I’m ready!” Ricky smiled. He couldn’t wait to get on with his afternoon plans.


A bell dinged as Ricky pulled Chris through the threshold of the door. The silver-bearded man at the counter looked up from his embroidery, and removed his magnifying goggles. “Well, well. If it isn’t my favorite customer. And he brought a friend.” The man looked Chris up and down. You could practically see his mouth starting to water at the sight of Chris’s skimpy mesh shorts. “And you must be Chris. I barely recognized you, but I guess that’s natural after twenty years. Please, take a seat. I’ll be right with you.”

Ricky led Chris to his seat and sat down beside him. The man grabbed his ring of keys and locked the door to the shop, flipping the sign in the window to closed. He walked over to his seated guests and stood before them. He extended his hand to Chris, formalizing their introduction. “You can call me Art, but I guess you might remember me better as Coach Stephens.”

Chris sat there, processing for a moment. The name sounded familiar, but he couldn’t place it. The man standing in front of him was older, probably in his mid-50s, but had an amazing physique. He looked shorter than Ricky or Chris – 5’10” at best – but the size of his muscles made him imposing nonetheless. Clearly, this Art had been an athlete in his youth and spent a good part of his adult life maintaining his body-builder physique and selecting clothes that best accentuated his finest features. The rolled-up sleeves of his designer dress shirt strained against his biceps, while his voluminous grey chest hair spilled out of his unfastened collar. His leather pants, which had been obscured by the counter when Chris had arrived, were skin-tight and accentuated the man’s tree-trunk thighs and taut ass. The shine on his boots was military-grade. This was certainly not what Chris had been expecting from a small-town tailor shop.

“Sorry, Coach.” Ricky stood up and grasped the tailor’s shoulder, while Art’s hand lingered in front of Chris. “He’s a bit out of it. Had a dose of the good stuff on the way over. He’ll catch up with us in a couple minutes. How’s business?”

Art lowered his hand and chuckled. “Fuck business, look at the business you brought me. I can’t believe it, it really worked? After all this time?”

“I’m as surprised as you are, and ten times as grateful. I had no idea what I was doing back in high school when I planted that trigger. I got lucky.” Ricky smiled, happy to finally be talking about his project with someone else. “I really hit the jackpot, eh? Clearly he took care of himself all these years, not to mention the seven figures in the bank. I’m so glad he’s decided to stay a while.”

“And I’m so glad you’ve decided to share the wealth, Councilman. Always looking out for the community.” Art winked and turned back to Chris, who was blissed out and relaxed in his chair.”

Ricky laughed. “Well, you know what I always say: Service is the best choice a man can make!” With the uttering of the familiar trigger, Chris’s head dropped. Art looked on in amazement. “Chris, babe. You wanna stand up, so we can try on your suit?”

Chris stood up, his hard cock already leaking onto his shorts. Art did a double-take. He’d assumed Ricky had been exaggerating when he mentioned his encounter with Chris in the woods.

“Good man,” Ricky said, grabbing Chris by the hand. “Let’s follow Art to the fitting room.” Art led Ricky, and Ricky led Chris in turn, to a large room at the back of the shop. Red curtains adorned the walls. In the middle of the room was a platform, flanked by full-length mirrors to facilitate Art’s work.

“Okay, Chris. Can we get you on the platform and down to your underwear.” Art said, his voice gentle yet full of experience and authority. Chris did not respond, and was still just taking in his surroundings.

“Shit, sorry. He’s still a work in progress. Just a sec.” Ricky turned to Chris, looking him straight in the eyes. “Chris, babe. The Coach is here to help us out. When he asks you to do something, it is like I’m asking. Do you understand?”

Chris processed this for a moment. Then he smiled. “Yeah, I get it, Sir. Coach is here to help.” Chris stepped up onto the platform and stripped down to his jock strap. While his outfit had been revealing, taking off a layer left nothing to the imagination.

Art looked him up and down. “Wow. I couldn’t believe those measurements you sent me, but damn. To be honest, I don’t remember much of him from my days at Carson High. As you know, I’ve always been more interested in the men my students become. Thank god you were out there, scouting talent.” At this, he chuckled to himself.

Art’s teaching days were long behind him. He’d had a happy and satisfying career until one day, the PTA decided that they didn’t want a faggot teaching their sons P.E. anymore. Of course he’d never crossed a line or done anything wrong – teenagers weren’t his type. It was clear, though, that one too many dad had seen Art’s car during their own weekly trysts at the rest stop and started a smear campaign to ensure their own secrets stayed safe. It wasn’t long before Art was out of a job and had to start from scratch.

He figured that he’d be best off leaning into the faggot lifestyle, so he picked up a needle, learned to sew and started his tailor shop. His side-hustle also gave him a lot of satisfaction, supplying leather goods to the down-low men of Carsonville. Even the self-hating monsters that had got him fired couldn’t resist his custom line of ass-less chaps and the ‘quality service’ that came with them. This was how Art had re-connected with Ricky a few years back, after he’d gone to college, then law school, then New York, and then back home. It was also how Art got to know his husband, Luther, who moved to town to be the pastor at Carsonville’s first LGBT-affirming church. Art himself wasn’t religious – far from it – but even he had to admit that, despite the bumps along the way, he had built himself a pretty blessed life.

Ricky himself was getting hard, watching Art leer at Chris. “The least I could do, Coach. But while we’re on the topic, I was hoping I could ask you for one more favor.” Art had daggers in his eyes. He’d given up a week’s worth of business to help Ricky get Chris’s suit in tiptop shape. “Relax, man. It won’t even feel like a favor, trust me.”

Art was intrigued, and had a feeling he knew where this was going. “Okay, I’m listening…”

“Well, you see, Chris isn’t always as docile as he is right now. It’s taking a while for his treatment to settle in, and I’m still having to pull him back under several times a day. Don’t get me wrong, he’s doing great, but I don’t think he’s internalized his new role yet.” Ricky walked up to Chris, and grabbed his left ass cheek, gripping it with dominant force. “I think he’s a bit confused. Sure, he’s a natural cock-sucker. But I think my whole ‘power bottom’ thing has left him a bit confused on a subconscious level about who is in charge. I’m sure he’ll learn over time, but I think speeding things up will help his mind settle into its new equilibrium. So, what do you say? Do you think you’ve got time this afternoon to set him straight, for lack of a better phrase?”

Art looked sternly at the two men, and then walked over to them. Pushing Ricky out of the way, he got up on the platform behind Chris and put the stud in a practiced choke-hold. His thick cock was getting hard, his tight pants growing tighter. “To be clear, you want me to fuck him into submission, right?”

Ricky laughed, catching a glimpse of the pair at many different angles in the mirrors. “Something like that. You can even call Luther if you like.” Ricky knew that Art and Luther both tended towards topping, and had a roster of men to call on for their needs. In fact, Ricky was at the top of their list.

Art thought for a moment. “Better wait on that one, I think. I love my husband, but Mr. Goody-Two-Shoes can be a bit uptight about fucking someone who’s not totally there. Not to mention kidnapping across state lines.”

Ricky was taken aback. “Hey! He drove himself here. Nobody’s kidnapping anyone.”

Art chuckled. “I guess you’re technically right. Not that it matters though. Luther might have to set a good example for the community, but me?” Art tightened his grip on Chris before releasing a little bit. “I’m a sick bastard. I’d be happy to help break your boy in. Lots of time to share later.”

Ricky smiled, and made his way to the platform. He stood face-to-face with Chris, their noses only an inch apart. “Thanks Coach, I knew I could count on you.” He locked eyes with Chris, who wasn’t struggling against Art’s grip but seemed a bit uncomfortable. “Hey babe, remember when we said that Coach was here to help, and you should listen to him?” Chris nodded. “Good, that’s important. But I need you to do even more than that. Coach is really doing us a favor, and we need to show him how much we appreciate it. I need you to be very enthusiastic for him. Do you understand?”

“Yes, Sir.” Chris managed to speak despite the choke-hold. “Coach is here to help. I need to let him know I appreciate his help.”

“Good boy, you’re doing great. I’m going to go take a seat and make sure I get this on camera.” Ricky flashed his iPhone in front of Chris’s face. “Go ahead, Coach. He’s all yours.”

Art released his grip and Chris slumped over. “Straight, boy!”, Art barked. Chris immediately complied, standing tall and at attention. “Stand here and wait a minute.” Art stepped down from the platform and walked over to a wardrobe. From inside, he pulled out an expensive-looking leather harness fitted to Chris’s proportions. “I hope you don’t mind, Ricky, but I look the liberty of fashioning something up for him.”

Ricky nodded excitedly, making sure to capture the harness on film. “Oh, I don’t mind at all. I’m sure it’ll fit him like a glove.”

Art walked back over to the platform and fastened the harness around Chris’s chest. “There you go,” Art said in his soothing but stern baritone. “Now you won’t have to think about where I want you. I’ll just take you there.”

Chris was still slow to process, but eventually stammered out: “Thank you, Coach.”

Art grabbed Chris by the harness and led him off the platform. “On all fours, boy.”

“Yes, Coach.” Chris got on his hands and knees, trembling. He felt unsettled, but in a good way. Like the disorder in his life was giving way to clarity of purpose.

Art snapped the elastic waistband of Chris’s bright blue jock strap. Chris flinched. “Look at this nice jock that your Ricky got for you, boy. It makes you look so good. And yet, he’s still having trouble breaking you in. You should know better, don’t you agree?” Chris nodded, and Art spanked Chris’s ass hard enough to leave a red hand-print behind. “Good, glad we see eye-to-eye on that. Because I don’t put up with that shit.” Art moved his hand toward Chris’s hole, and teased it with his thick index finger. “Look at that. It’s been a long while since I’ve had a genuine virgin hole come through these doors. But all good things have to come to an end, right boy?”

Chris shuddered audibly when Art addressed him this way while taunting him. “Yes, Coach, you’re right.” As these words escaped his lips, Chris heard the Coach spit and felt the new sensation of a wet finger being rubbed against his hole. He moaned, looking to the side at Ricky and his camera. Ricky was grinning ear-to-ear as he documented his prize learning the ways of his new world.

“Get back up on the platform, kid. My knees aren’t what they used to be.” Chris crawled up onto the platform, his round ass swaying as he crossed the floor. Once he got back into position, Art began to explore more of Chris’s asshole with his finger. Chris was breathing heavily, still adjusting to the new sensation. “What do you think, Ricky? Time to break him in for you?”

“I think he can take it. Go for it, Coach.” Ricky rubbed himself through his pants with his left hand while filming with the right. “Chris, dear, don’t forget to watch yourself in the mirrors. You only get one first time. Make some memories.” Chris adjusted his position, getting a better view of his own ass in the air, the leather-clad daddy looming over it, and his own mouth hanging open, anticipating what was next.

It did not take long after Ricky gave his assent for Art to rip open the button-fly that had been holding back his 9’ cut cock. He grabbed a bottle of lube kept under the platform and doused Chris’s hole. Art slapped his rock-hard cock against Chris’s virgin ass, taking a pause to savor the moment. Chris moaned at the sensation. He was ready now. Art teased Chris like this for a couple of minutes before relenting. “Okay, boy. Time to remind you what you’re for”.

Art slowly pushed the length of his cock into Chris, whose eyes had rolled to the back of his head in ecstasy. He whimpered as inch after inch penetrated him, feeling the dual sensations of the Coach’s force and his melting mind. He was the most focused he’d been in days, and he had one priority: to serve these men, and leave them satisfied. He started backing onto Art’s cock on his own will, eager to swallow its length inside him.

Art gave Chris’s ass one more slap, using full force, as Chris moaned, begging for more. Art turned to his friend and looked down the barrel of the camera and smiled. “Ricky, I think your bitch is in heat.” With that, he turned his gaze back to Chris and started thrusting, slowly at first, but soon enough he was up to full throttle. Art started to sweat heavily, his shirt marked with stains under his pits from the exertion. Drops of sweat dripped from his beard onto Chris’s glistening ass. The boy was marked, now.

Ricky started to circle the pair, capturing their passionate fuck from many angles. As he approached Chris’s face, he whistled to get the boy’s attention. Chris looked up at his lover’s face, torn between Ricky’s comforting gaze and the pleasure impact of the Coach’s rapid thrusts. “Keep your eyes on mine, babe…”, Ricky said with tenderness. Chris focused in, but couldn’t help but whimper each time his prostate was stabbed. “Sounds like you’re enjoying yourself, huh?”

“Uh-huh…” Chris stammered out between moans. Ricky narrowed his eyes disapprovingly. Chris caught on fast. “Yes, Sir. I mean. Sorry, Sir.”

Ricky smiled at the correction. “That’s my boy. I hope you’ve learned a valuable lesson today, hun. Don’t let any pre-conceived notions of ‘tops’ and ‘bottoms’ infect that pretty little head of yours. You’re at my service now, even if you’re the one fucking my ass. And don’t forget it. But if you ever need a refresher, I’m sure the Coach would be happy to oblige.”

Ricky shifted the camera’s focus to Art, who - after fifteen minutes of continuous fucking - was clearly on the edge of orgasm. Seeing that he was on camera, Art pulled out of Chris and started stroking his lubricated cock. It didn’t take long before he was spraying ropes of cum, covering the globes of Chris’s muscular ass and soiling the waistband of his jockstrap. Exhausted, Art zipped himself back up and wiped his brow with his left arm. “There, Ricky. I think he’ll be broken in for you now.”

“What do you say, Chris? Have you learned your place?”

Chris smiled, still feeling the rush from being coated in the Coach’s seed. With more enthusiasm than Ricky had ever seen from him before, Chris said: “Yes, Sir! It is an honor to serve you. It’s the best choice I’ve ever made.”

Ricky was delighted. It seemed like Chris had a significant breakthrough during his session with Art, and was starting to enjoy his new lifestyle. Ricky stopped filming and stroked Chris’s chin affectionately, and gave him a loving kiss. “Glad to hear it, babe. Now stand up so the Coach can finish his work.” Chris stood up on the platform and looked at himself in the mirrors, watching the Coach’s cum slowly drip down his cheeks. His untouched cock was as hard as ever, leaking generously into his jockstrap.

Art approached with a tape measure, and after taking a moment to admire his work, he took down Chris’s measurements with diligence and satisfaction. “Pretty close to what you told me, Ricky. I’ll do some minor modifications this afternoon and have it sent over to your place in the morning. Thanks for bringing him in. I needed that.”

Ricky laughed, putting his arm around Art. “Anything for you, Coach. I mean it.” Ricky looked at his watch, then turned to Chris. “Babe, we should get going. Get dressed. You’ve got a few things to do around the house while I catch up on work, and then you’ll need to get dinner on the table. I was thinking steaks, how’s that sound?”

Chris grabbed his skimpy shorts and tank top from the floor and put them on over his cum-soaked body. The outlines of both his throbbing cock and his snug harness were on clear display for the world. “I’d love that, Ricky. Sounds great.” Chris was finally speaking more organically and fluidly, allowing Ricky to feel both excited and relieved. Before this afternoon, he was a bit worried that his plan wasn’t coming together, but now he was sure that Chris was definitely the partner that he dreamed he would be. He grabbed Chris’s hand and the couple turned to exit the shop.

“Thanks again, Art. I still owe you big. Oh, and I’ll be seeing you at the after party on Friday?”

Art laughed. “Definitely. I wouldn’t miss it for the world. Enjoy your evening, boys.”

With that, Ricky and Chris headed toward the car and made their way home. With the suit out of the way, they were almost ready for Friday’s reunion. After a couple more days of rest and relaxation at home, Ricky was sure that Chris would be ready for showing off in front of the whole town. But only at the after party would Ricky’s plans come to full fruition. To him, that was the real countdown.


To be continued…

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