“Yup. We have another date tomorrow.”

The twenty-one-year-old sipped his beer, enjoying the company and the cooling air as the July sun sank over the trees.

“How many is that since school got out?” Mr. Fitzsimmons took a swig from his own bottle, and enjoyed the way the young man’s reddish beard and dark-blond hair glinted as a last ray of the sun hit his face. The two of them were relaxing on the powerfully-built security guard’s screened porch; Chris had paid him a couple of home visits this summer, just to hang out. And to seek counsel.

“This’ll be number three.”

Sean ran a long, thick finger around the bottle rim.

“That’s a lot.”

“Yeah.”

“So you like him more than you used to?”

Chris’ tight, perky butt squirmed on the woven seat. He took another sip.

“Well, I liked him a whole bunch when we first met. I had a huge crush on him.”

“Because he’s an adult.” Mr. Fitzsimmons knew Chris’ history: the ad man who was eight years Chris’ senior had represented maturity in the boy’s life. While it was true that Chris had developed an insatiable need to serve men once his submissive side had been awakened, Mark had also been someone Chris could genuinely look up to, and mostly trust.

“Because he kissed the shit out of me,” Chris corrected.

They both laughed.

“Mark was my first kiss. And yeah, he treated me like a . . .” Chris was still a little embarrassed to say it so frankly and casually in front of someone “. . . a sub. But also like a person. And now he does treat me like an adult too, yeah.”

Sean rested his bottle on his firm belly, and contemplated his rock garden. “And what are you guys gonna do?”

“I’m not sure,” Chris blushed. “Probably fuck, but the lead-up is always a little different. He likes to teach me things and push my limits.”

Mr. Fitzsimmons looked at Chris drily.

“I meant, are you going out for dinner? Making pottery? Playing miniature golf? You know, on your ‘date’.”

Chris took a large swig to cover.

“He’s taking me to a free concert out in the park. The symphony is playing.”

“Classy.”

“I’ll feel real classy with his hand down the back of my shorts when it gets dark,” Chris said smiling.

“A boy should always feel a little vulnerable,” Sean said sagely. Chris started to get hard.

“Yes, Sir.”

“I’m not your Sir,” Mr. Fitzsimmons laughed. “You have a couple of others who fit that category better than me.”

“You are when you spank me, Sir.”

“Well, of course. But that’s only situational, and only when you really deserve it. Which hasn’t been for a while. Unless you have something to tell me, young man.”

A smile crossed Chris’ handsome, slim face, but he didn’t respond. His slate was clean. A bird chirped. They sat, sweating companionably, on the porch. For similar reasons, neither wanted to be in the air conditioning; they both enjoyed the manly scent that rose off a guy at the end of a long, hot summer day. Chris set his empty bottle on the table, and Sean admired the arm that was noticeably more muscled than when they had first met a year ago, and the tight t-shirt which hugged the boy’s firm, hairy pecs. Chris’ movements were still self-conscious, as if he didn’t quite recognize his own body – or as if he felt he hadn’t truly earned it yet.

“Want another?”

“Sure.”

“You’ll have to wait a little before I’ll let you drive.”

“Yes, Sir,” Chris smiled. Although he and Mr. Fitzsimmons were not sexually involved, he deeply appreciated the fatherly – and disciplinary – role the older security guard had come to play in his life.

“So it’s going well?” Sean handed the boy a second bottle from the cooler on the porch.

“What is?”

“You and Mark.”

“Yeah.”

That wasn’t entirely convincing, Sean thought. So he asked the million-dollar question.

“Have you heard from Justin?”

Chris took a deep swig. Mr. Fitzsimmons knew all this sordid history, too – how Chris’ former roommate had forced him to suck him off the first night they had roomed together and then turned him into his personal slut, and how Chris, despite the abuse, degradation, and even violence, had fallen in love with the shaved-headed jock. The past year had been rocky. Justin had moved out of the dorm and into his frat house. Chris had moved off campus. They had hooked up several times, but Justin had lost his cool when he discovered that he had not, in fact, busted Chris’ cherry that emotional night after Chris had been cut from the pledge class at Justin’s frat. Yeah, that night had been the first time Justin had fucked his boy. But Chris had already given up his hole to Mark six months before. When Justin found out, he had punched Chris in the face. They had made up a few months later, sort of. And Chris would be lying if he said he didn’t still have feelings for his old roommate. But it sure was fuckin’ complicated now.

“Yeah, I have.”

That was a long pause, Sean thought.

“And?”

“I don’t know what to think.”

“What do you mean?”

“Well . . . last summer – the summer I met you – he was away on an internship too, and he hardly texted at all. And he always seemed pissed off. This summer, he texts every couple days. So there’s a lot more contact. But I don’t feel like it’s about . . . us, you know what I mean? Mostly it’s asking me if I’m going to live with them in the fall.”

“With him and his other two frat buds?”

“Yeah.”

“That is about you,” Mr. Fitzsimmons observed.

“Yeah, but not really.”

“How so? He wants to live with you again. That’s kind of a thing.”

“That’s about externals. And logistics.”

“And you want him to talk to you about feelings,” Sean said, smiling.

Chris returned the smile sheepishly. “Yeah, I know. So gay, right?”

“Don’t say that, young man. Self-deprecation won’t fly here.”

“Yes, Sir,” Chris answered nervously.

Sean rolled his eyes. “Don’t look so scared. I’m not going to spank you. But I’m serious. You’re a very special young man, and you need to treat yourself with dignity.”

Chris opened his mouth, embarrassed, but Mr. Fitzsimmons continued. “You think because you’re a sexual submissive that you need to bow down to everything your Dom wants or says. Especially Justin, because you’re in love with him.”

Chris turned bright red.

“Even if you are dating Mark.”

It was true, but not something Chris allowed himself to articulate. Justin would self-destruct at the “L” word, and besides, there were so many caveats with the jock. Like, is he gonna deck me again.

“You’ve been through a lot with Justin.”

Chris’ blue eyes stared fixedly at his beer.

“And you do love him.”

Chris began to peel the label off the bottle with nervous, lithe fingers.

“But I think you’re wise to be cautious.”

“Mark thinks I should forget about him and move on.”

“Of course he does,” Mr. Fitzsimmons said drily. “He’s trying to date you. Mark has his own agenda. Which, by the way, is really sweet. And you know, maybe he’s right. On a purely objective level, Justin is really bad news. And he’s hurt you in every conceivable way.”

Chris found a particularly fascinating mole on his arm, hidden in the light blond fuzz; he studied it.

“But, you still see something compelling in him. And you two have a whole lot of history. And he’s done some nice things for you, too, from what you’ve told me.”

Chris sighed. “Yeah, that’s all true. I just wish . . .”

“What?” The security guard’s gray-blue eyes radiated sympathy.

“I wish Justin were easier to talk to. It’s like the most important stuff . . . we can’t ever go there. And when everything is threatening to fall apart, he turns into a hero, and he rushes in and saves everything. Well, me. He saves me. But the rest of the time, he’s aloof, and resistant, and only focused on how I can . . . you know . . .”

“Serve him?”

“Yeah,” Chris admitted, blushing.

“Sounds like a real Alpha. And you know . . . words aren’t their strong suit,” Sean chuckled. “But if he rushes in to save you when he knows it’s crucial . . . well, maybe that’s something you can build on.”

“Yeah, that’s what I think, too. But Mark -”

“Mark is older than both of you, and wiser. He’s a catch. And you seem to think so, too. Except when you don’t.”

Chris finished his beer in an anguished gulp, then burped loudly.

“Oops.”

They both laughed loudly.

“What the fuck am I supposed to do?”

“Do you have to make up your mind right now?”

“No. Yes. I don’t know. Yeah, I kinda do, don’t I? I don’t want to lead Mark on if I’m not serious.”

“But you don’t know if you’re serious.”

“I think I am. There’s a lot about him I really like.”

Sean Fitzsimmons rubbed his buzz cut thoughtfully, revealing a huge wet spot under his arm. He traced his receding hairline with his thumb.

“Can I give you some advice?”

“Please!”

“If you really do think you’re serious about Mark, you can’t have Justin in your head all night tomorrow.”

“I know.”

“Do you? Do you really not think about one the whole time you’re with the other?”

“No, not really. I mean, I usually don’t think of Mark when I’m with Justin, and I don’t think of Justin all that much when I’m with Mark.”

Sean suppressed a smile.

“Just promise me.”

“What?”

“Don’t think of Justin at all when you’re with Mark tomorrow. Go all in for him when you’re with him. Don’t check out. You can think about the rest of it later.”

“Of course.”

“Don’t ‘of course’ me, young man. We both know you imagine yourself with each of them. Just don’t do it while you’re on a date with Mark. Promise me?”

“I promise, Sir.”

“Good boy.”

The twilight deepened. They conversed some more, but languidly, mirroring the sultry evening. Eventually Chris said goodbye, and drove his jeep back home. Perhaps in a nod to Mr. Fitzsimmons’ instructions, he did not check his email, texts, KiK, or anything else before arriving at his third-floor room. He changed for bed, idly admiring his thickening, hairy legs as he stripped. He had decided on an early night, so as to get in a workout the next morning before his shift at his café job. Couldn’t see Mark without looking his best.

Only once he had put on boxers and a t-shirt and slipped under the sheet did he look at his phone. There were several texts, including some from both Mark and Justin. He read Mark’s first.

“Looking forward to tomorrow night, boy. Dinner is at 8, sent you the reservation. Wear shorts, a plain white t (tucked in), flips, no underwear. Put on the cock ring I gave you last time. Don’t be late.”

“Yes, Sir,” Chris texted back automatically, his small dick hardening at the electronic orders. He loved having ordinary activities sexualized, and hot men he trusted telling him what to do. He reached down into his boxers . . . and withdrew his hand. While there had been no proscription regarding masturbation before the date, he knew he’d be in a more intense subspace if he waited, fretting hornily all day. And he could tell Mark about his unforced behavior, and perhaps earn some credits against whatever infractions he would undoubtedly commit over the course of the evening.

He thumbed over to Justin’s message. There was more than one. That was unusual.

“How’s my boy?” That had come around 7, when he had been chatting with Mr. Fitzsimmons. Then,

“Plans for the weekend, Chrissy?

“Gotta head out to Long Island tomorrow. Firm having a big party. So big even I’m invited lol.

“Wish you were here suckin my huge cock roomie.”

And then there was a pic of Justin’s uncut monster, mouth-watering, surrounded by thick, dark hair which the frat jock clearly hadn’t trimmed in a while. Chris got fully hard at the sight. That fat cock had been in his mouth almost every day his sophomore year, and up his ass quite a few times last year, too. Something about being called “roomie” by an athletic, popular hunk always made Chris feel warm and gooey inside. The lean, bearded boy may not have won entry to Justin’s fraternity, but he had an intimacy with the man that his frat brothers never would.

If only . . .

If only he were here?

Yeah – but really, it was . . . if only we were dating, and not just continually fucking around.

But that’ll never happen, Chris thought. Unless, a small voice reminded him, you go live with him next year. That has to be your best shot at getting as close to Justin as you always wanted. Maybe your only shot. Just think about it – roommates again. Well, housemates.

Yeah, Chris pointed out to the randy voice of hope, there will be two of his frat brothers in that house. And I would be in the basement, conveniently nearby to fuck, but otherwise ignored. The sex slave in the dungeon . . .

Chris’ dick twitched again. That was actually a hot scenario. But the emotional reality of it was so daunting – after all he’d been through with his ex-roommate, he didn’t know if he would be able to handle a situation where his place was so clearly defined, his objectification so brutally complete.

If you were a real sub, you’d jump at the chance, another, crueler voice lectured him. Why can’t you just be what you were meant to be? What God made you when he gave you a tiny penis?

Chris rolled onto his side, trying to shut out the endless argument in his head, the one he’d been replaying every night since Justin had taken him out for his birthday, almost three months ago. He glanced at the picture on his phone one more time, then realized there was another message after the dick pic.

“When are u gonna decide, roomie? We need to know if ur moving in or not.”

I don’t know, Chris thought, and firmly put the whole subject out of his mind, concentrating instead on the thought of Mark’s handsome face coming in for a kiss.

************

Standing with a cane clenched between your butt cheeks becomes hard after the first minute, Chris decided. Especially when your Sir inserts it almost vertically, so that only the tops of your ass muscles are able to hold it in a relatively shallow channel. Not to mention, those cheeks are striped and sore from rigorous application of the instrument in question, which makes clenching even more tiring. Takes your mind off aching shoulders from having your hands on your head, though, he thought. Small mercies.

Mark surveyed his boy, pleased at the angry red welts on Chris’ pale, chiseled buttocks. He had only used the rattan cane so far – no warm up, no over the knee. Just 24 solid, well-paced whacks, spread out over the minutes and the boy’s glutes, which had made the young man gasp in growing pain and fear . . . and made Mark’s nine-inch uncut cock hard as steel. He adjusted it in his cargo shorts. In keeping with the power imbalance, he was still half clothed while his slave was naked. The meaty nipples on his bare chest were erect, too.

Mark was pleased he had kept the boy off balance. Their picnic in the park had been fun and sweet, and he was sure Chris had not been anticipating a rough session with the worst possible disciplinary implement immediately upon their return to Mark’s condo.

But – the boy needed to learn to be a true sub. No questioning, no argument, just submission to Mark’s will. And Chris had done an outstanding job. No complaints, no backtalk. Just the widening eyes and panicked breathing that turned Mark on like nothing else. The trembling legs on the boy were hot, too, as holding his position became tougher. The 29-year-old executive glanced at his TAG Heuer, and allowed one more minute to pass before strolling over to the slim but muscled young man. Mark grabbed the cane with his hairy arm, and gently lifted it away from Chris’ ass, massaging the boy’s shoulders as he lowered his arms to his sides. He stood close, his ample, dark chest hair teasing Chris’ upper back, and his engorged meat poking through cotton at the boy’s very punished, angrily striped bottom. Mark dropped the cane on the floor, and wrapped his arms around Chris.

“You looked so hot standing there, boy,” he whispered in Chris’ ear. “I wanted to leave you there forever.”

Chris smiled, sore but secure. He knew Mark would challenge him, and even do unexpected things, like tonight – but he never feared for his safety, either physical or emotional.

Mark considered what he might do next. He wanted to train Chris, to condition him to obedience . . . and tease him. He turned around and sauntered cockily to his easy chair, lowering his shorts and boxers and kicking them to the side before he sat down.

“Turn around, boy.”

Chris turned.

Mark pointed at the floor. “Over here.”

Chris was feeling very submissive after the slow, harsh beating, and figured he might earn extra points by crawling, so he got onto his hands and knees and made his way across the red oriental carpet to Mark’s large feet.

The Dom’s dick twitched again. This boy was such a keeper. Young, pliant, masculine, really cute, and with a body that had tightened and improved tenfold over the last year.

“Good boy.”

Chris looked up, hopefully eyeing various parts of Mark he’d like to lick: the mildly sweaty size 12s, still scented with leather loafers . . . the enormous ball sac which hung plumply between the ad man’s spread legs . . . the massive torpedo jutting out proudly . . . or farther up, the erect nipples buried in curly masculine dark hair, the fragrant armpits . . . or maybe even the smiling, full, bearded lips, which might have been Chris’ favorite part of all. He loved to kiss – or rather, be kissed, strongly, commandingly. And Mark was an excellent kisser.

“Up on your knees, boy.” Chris obeyed. Mark opened a box on the side table, and pulled out a black drawstring bag. He opened it, revealing a piece of plastic shaped in part like a penis.

Chris paled. He had read and fantasized about this since the first time he had seen something like it online, but he also completely dreaded it.

It was a male chastity device.

“You know what this is, boy?”

“It’s a Holy Trainer, Sir.”

“That’s right, boy. And you know where it’s going?”

Chris swallowed. “On my dick, Sir?”

“More like a clit, wouldn’t you say, boy?”

Chris’ penis was four inches hard, and it jumped a little at being humiliated.

“Yes, Sir.”

“Say it, boy.”

“It’s going on my little clit, Sir.”

“And why is it going on your little clit, boy?”

Mark’s own large, thick, uncut meat was pulsing with his heartbeat.

“So that I can focus only on your pleasure, Sir.” Chris bowed his head, mortified but fulfilled.

Mark reached out with his right hand. Chris felt a finger under his chin, gently raising it.

“Say that again, boy,” Mark said quietly, his dark blue eyes intense but not unkind.

“I want to focus only on your pleasure, Sir,” Chris said slowly. It was hard to be that vulnerable, to say something so demeaning while looking into his Dom’s eyes. He felt safe, yes; but he was also deeply embarrassed.

Mark noticed the boy’s dick starting to wilt, and made a mental note of it. He also took advantage of Chris’ lack of tumescence to start putting the device around his cock and nuts. Chris’ balls slipped through the ring of the Holy Trainer easily, and then Mark pushed the boy’s shaft through.

The older man held two fingers in front of Chris’ face.

“Open.”

Chris opened his mouth obediently, and Mark stuck the fingers in.

“Get them wet.”

Chris swirled his tongue around and struggled to manufacture saliva in his dry mouth.

“Wetter.”

Chris put more effort into making moisture. Mark withdrew his sloppy fingers and quickly, roughly stroked them over the boy’s little cock and ran them around the inside of the chastity cage. Thus crudely lubed, the Dom began to push Chris’ thin member into the device. It took some prodding since Chris was now half hard, but in less than a minute, the boy’s dickhead had made it past the thin part of the tube’s shaft and into the plastic bulb at the end of it. Poor Chris’ small endowment was dwarfed by the chastity device; even half hard, he didn’t come close to filling it. Mark fit the two pieces together, and produced the key.

“Are you ready, boy?”

Chris blinked and shuddered. He nodded.

“Say it to me, Chris. Ask me to lock you up.”

This was hard. Chris looked reluctantly into his Dom’s eyes, and said the magic words: “Please lock up my little penis, Sir.”

“Are you sure that’s what you want, boy?”

Nooooo! Chris screamed inside his head . . . but he knew that was the wrong answer. If he didn’t agree, he’d get another caning. And there was no more unmarked real estate on his ass, so it would really be excruciating. Or worse, Mark would simply send him away. And Chris knew he didn’t want that. Thoughts of punishment and control made his dick started to swell in the device, finally meeting plastic on all sides. It was uncomfortable, but not painful. Chris thought . . . and decided.

“Yes, Sir.”

“Alright, boy, you asked for it.”

 

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