The cost of failure is pleasure – part 1

edging, forced arouasal

A young man discovers that he doesn’t have as much sexual self-control as he thought he did.

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The cost of failure is pleasure – Part 1

William passed the ID to his cameraman Phil, and Phil double-checked it. It showed that Trey had turned 18 just a month ago.

William gave Trey a reassuring smile, but his thoughts were less noble.

“Fresh meat. Perfect. They’re so easy to mess with.”

“Okay then Trey,” William said out loud, “so you understand what you’ll be doing here today. Phil will be slowly jacking you off; gently touching your dick, and teasing you. Have you heard of the word ‘edging?’”

Trey shook his head. Like all first timers, he was nervous, but he’d lived next to William for six years, and the overweight old guy seemed pretty harmless.

“Edging is when someone plays with your dick and takes you right to the edge of cumming, but doesn’t take you over the edge. It’s VERY important that you don’t cum without my permission do you understand.”


“You are not to cum for 30 minutes no matter what. There’s a clock on the wall that we can both see, but I’LL tell you when it’s okay to shoot your wad got it?”

“Yeah. I mean, I’m not even gay, so I don’t think that’ll be any problem whatsoever, but what if I can’t even get hard?”

William smiled.

“Oh, you leave that to us. I don’t think it’ll be a problem.”

“But what if I can’t cum?” Trey persisted.

“If we get to that point, you can jack off till you cum okay?”

“And I’ll still get paid?”

Trey looked at the man’s expression. It was a mixture between humour and gentle confidence. Trey felt a little flutter of nervousness in his stomach. He’d known that William was gay since he was 15, and when Trey was 16, William confided that he made gay porn for a living. When Trey was 17, William suggested that he was willing to pay $500 per session to be jacked off. And now, barely legal, but old enough to sign the documents without his parent’s consent, Trey stood ready for his first session.


“So, just to be clear,” William said, “if you DO cum in less than 30 minutes, we get to play with you for another 3 hours while I film it agreed?”

“W… what do you mean “play with me?” Trey asked.

Phil was already recording on his digital camcorder. He always started early so that the models’ consent ID and was on video. He zoomed in on the boy’s face. Trey looked uncertain.

“Oh, nothing freaky; we just get to make you cum as many times as we can that’s all.”

“You won’t be fucking me or making me give you a BJ or anything like that. I’m not gay.”

William smiled.

“You already told me that a couple of times. I know you’re not gay. That’s what makes it so hot. So no, nothing like that. Just lots more jacking. Emptying your balls.”

“And nothing painful.” He lowered the volume of his voice conspiratorially. “I’m not into that stuff.”

“No, no, definitely nothing painful. Just horny fun I promise.”

Trey gave him a lopsided grin.

“Horny fun doesn’t sound too bad.”

“Course it’s not. And anyway, you told me you’re straight. Phil probably won’t even be able to make you cum at all right?”

He gave Trey a wink to let the kid know he was messing with his head. Trey had already browsed through a ton of videos on William’s site. Every single one of the guys came.

“R… right. I guess not.”

“Great, so I’m going to be on the camera today, and as I already told you, Phil is going to be doing the edging. Let’s start by getting you undressed. If you’d just like to take your clothes off please.”

Trey stripped down to his boxers then paused. William looked him up and down. He’d seen the boy shirtless in shorts many times while Trey mowed his family’s lawn. William had even hired his services himself on a few occasions. But this was the first time he’d seen the boy in his underwear. Trey was wearing white sport boxers; short, tightish – closer to what they used to call “boy shorts” in the 70s. They were Calvin Klein – poor man’s designer label – most of his models wore them, bought specifically for the session no doubt.

Trey had a nice bulge. Not large, no sign of a hidden beast slumbering within; just a compact lump, big enough to distinguish from his crotch, and enough to show that he was male. But no females would ever catch sight of his bulge and gasp in trepidation knowing that they would soon be ploughed by what lay within. The word that popped into William’s head was “cute.”

“And the boxers,” he said. “We don’t do undressing. Nobody wants to watch that. It’s straight to business.”

Trey looked queasy. He hesitated. Some models brashly tore their underwear down without asking, standing there arrogantly with hands on hips as though William should be honoured to see them nude. Trey was timider, but without asking a second time, he slowly lowered his briefs allowing his genitals to bounce into view.

William loved cocks: big cocks, small cocks, average cocks, cut, uncut, brown, black, white, and pink, he loved them all. But nevertheless, he was pleased by what he saw.  Trey was uncut, and his dick was the same healthy colour as his belly, and no more than 3 inches long.

“You shave?” William asked.

Trey swept his palm down from his belly to the top of his cock, suddenly self-conscious.

“I gave it a try a couple of weeks ago. I wasn’t sure how it looked?” he responded, clearly looking for approval.

William looked at the boy’s body. He had legs that were coated in hair; thicker than vellus, but not long and curly. The same hair covered the treasure trail up his flat belly to his navel, and though his pubic hair had started to grow back, it matched the other two areas in length perfectly.

“Looks good,” William said. “Bet it would look even better completely smooth.”

“I was gonna but…” Trey hesitated while he chose his words carefully. “But I didn’t wanna look too young. You know with my small dick and all.”

William smiled. Boys with small dick tended to be humble. It was one of their more endearing traits.

“It’s really not that small. What is it, three and a half inches?” he exaggerated.

“Two and a half.”

“Hmmm,” William nodded. “Looks great and a lot of guys like modest dicks. Stops them feeling insecure.”

Trey grinned lopsidedly.

“I never thought of it like that.”

“Yeah, anyway, you have a great dick. Now, what I’m gonna do is tie your arms to that frame over there. You saw it in the other videos didn’t you? It adds to the fantasy. Our viewers like to believe that you don’t have the choice to simply stop me.”

“Oh, yeah, I guess so. I ummm, yeah, I suppose.”

He walked over to the frame. It looked like a bed frame on its end, made of thick wooden slats attached to two vertical steel bars, but it was much sturdier. Trey turned so that his back was to it as he’d seen the other models doing, and William quickly wrapped ropes around the boy’s wrists, wrapping each one multiple times before lashing them tightly the frame 6 inches away from each of his hips. He’d discovered that the boys felt safer tied like that, rather than in his preferred crucifix position. It was as though they were just inches away from pushing a masturbating hand off their dick if they needed to. The truth was, whether their hands were 3 inches or 3 feet from their dicks, they would be equally unable to deny whatever William or Phil chose to do to it…


“Okay, I’m going to get you started, and once you’re hard, Phil will take over okay?”

William saw Trey take a deep breath.

“’Kay,” he said.


William approached and reached below Trey’s penis to the boy’s scrotum. He cupped the teenager’s balls. They were not particularly heavy. He rolled them lightly in his palm, feeling them slide inside the slippery-lined sack, then he allowed them to slide through his fingers as they passed up towards the underside of his penis. He allowed his fingertips to run lightly against the foreskin-covered glans, giving it the softest of touch as they bumped over the barely defined outline of his corona, revealing the shape of its head.

Trey tensed his stomach and sucked up his balls as he felt William softly stroke the underside of his  helmet. He didn’t want to actively resist, but it would demonstrate his heterosexuality if the man struggled to get him hard.

“Do any guys ever not get hard?” he asked.

“Not yet,” William replied. “But I’m sure there’s always a first.”

He strummed the tips of his middle three fingers beneath the boy’s glans as though he was playing a harp, each finger sliding along the silky skin and bumping over the ridge. He was in no rush. He wondered if Trey would be one of those models who surrendered instantly to the pleasure, regardless of who provided it, or if he was one of the more fiercely heterosexual ones who resisted. They were the most fun, and William hoped that Trey would be like that. He seemed to be all-boy, out there pushing the Flymo around the lawn, skateboarding, or working on his motorcycle, but you could never tell.

He glanced up at Trey, and Trey looked straight ahead, trying to disassociate himself; feigning disinterest, as though watching the man teasing his cock would somehow indicate his enthusiastic approval. William grinned. Straight boys were so charming.

William was in no rush to produce an erection. On one hand, boys who sprung wood at the slightest touch were very erotic, but then they also had the shortest fuses, and many had trouble lasting 15 minutes before involuntarily blowing their corks. It was gratifying to make a model that horny, but it didn’t make for a good video, nor an effective use of the five-hundred-dollar fee.

William had a clause that the models had to forego masturbation and sex for at least a week before the shoot so that they would already be unbearably horny, producing a great cum shot. But he also had a clause that if they came inside ten minutes, they’d only get paid a hundred dollars. Quite a few had failed, although William ultimately paid them two hundred. Phil was more than capable of defending against a pissed off model, but short-changing them, didn’t make for a good future relationship.


William continued softly diddling the underside of Trey’s cock, and slowly, like a small, timid animal, the head started to raise.


Trey looked ahead with even more determination. Much as he did not want to get a boner at the touch of a man, William’s patient tickling of his helmet was starting to have an effect. He felt his dick starting to fill with blood, then it lifted.

“He is an expert,” Trey reasoned with himself.

William switched to a pumping motion, just like the regular jacking motion Trey used in his bedroom, but with his fist facing the opposite way. His hand was very loosely closed, placing almost no pressure on Trey’s penis, and the cock continued to harden.

William moved his fist slowly. His goal was to make the boy hard; unbearably horny, but not to push him over the edge. He continued jacking, and Trey continued to get harder. His cock was fully self-supporting now, capable of maintaining an angle of a little over 90 degrees from his body. William smiled down at it.

“Looks like I was able to get you hard after Trey.”

Trey blushed.


“Don’t feel bad son. Your dick doesn’t have a brain; it doesn’t care who’s touching it.”

Trey gave an awkward grin.

“Anyway,” William continued, “I’m going to hand you over to Phil now. Remember no cumming without permission, and no shooting until at least…”

He looked at the clock. It read just before 11.35am.


Trey frowned.

“But you’ve already been going for 10 minutes.”

“Ohhh, that didn’t count Trey,” William said in a kindly tone, “That was just giving you a nice strong hard on.”

He looked down at Trey’s 5-inch erection. It twitched as he mentioned it, as though even the thought of his own dick was enough to make Trey more excited.

“Anyway, I’m sure a straight guy like you will have no problem going another 30 minutes…”


The younger man walked in and William took his place on the cameras. There was a tripod-mounted pro camcorder running continuously, and William picked up a hand cam.

Phil took over, lightly stroking Trey’s cock. He stood to the side, and gripped it lightly with near-straight fingers. The pink helmet peeped out of the loose foreskin each time he more moved his hand towards the base.

“Helmet looks like candy. Looks tasty. Have you ever had your dick sucked Trey.”

“Ummm, no.”

Trey felt surprisingly embarrassed at the question. It felt too personal.

“It’s great. Lips on the edge, a warm wet tongue sliding over the top. There’s nothing quite like it. Guarantee I could make you blow your load in three minutes if I put my mind to it.”

Phil dropped to a knee.

“N… no. Don’t. Please don’t,” Trey pleaded.

“Not so sure you can last 30 minutes?” Phil asked.

“I… I don’t want to… I’m not sure,” Trey stuttered.

Phil grinned up at him. He leaned his head towards the boy’s cock, drew the foreskin back and blew softly on the exposed helmet. Trey let out a noisy trembling exhalation and his knees fluttered inwards. Phil stood up and looked Trey in the face. He grinned at the boy.

“Two minutes in your case.”

Trey blushed, embarrassed and appalled at his dick’s eagerness to be touched.

Phil squirted lube on his right hand, and rubbed it over his fingers, before continuing his slow masturbation of Trey’s cock. On each downstroke, the helmet was exposed. He allowed his thumb to slide across the raw helmet skin on the return stroke, massaging it against the side of his index finger. Each time his rough skin touched the delicate, pink flesh of Trey’s glans, the boy involuntarily trembled.

“Not gonna last long at this rate son. Pace yourself.”

“I’m not the one in control,” Trey responded.

“Warn me when you’re getting close.”

“I’m getting close,” Trey said immediately.


Phil stopped jacking him and Trey’s cock continued twitching, its head flickering with every heartbeat, eager for attention.

Phil turned to William, and they exchanged a smirk.

“Straight boys have got no self-control,” William said.

“No-one knows how to make a guy horny like another guy,” Phil replied.


He reached under Trey’s cock and gripped his testicles.

“Your balls are tight.”

“Are they?” Trey asked. “Is that bad?”

“Not at all. Just means you’re eager that’s all.”

He gripped Trey’s nuts and pulled them gently downwards until they could go no further. He held them there, pulling firmly between the boy’s legs, forcing his dick to bow its head. Phil held the boy’s nuts, stretched, just on the edge of discomfort for 30 seconds; a minute; 90 seconds until Trey’s dick stopped trying to twitch.

When it finally quieted, he released Trey’s balls, and gave them a gentle upwards pat with his cupped hand.

He gripped Trey’s penis again. The shaft was brutally hard now, although the head was surprisingly soft. The foreskin had fully retracted, tucking in behind the head. Phil gripped the cock again, and started massaging it solely with his finger and thumb, no longer moving his hand in a jacking motion, but instead kneading the flesh between his digits like a man rolling tobacco leaves, giving the glans his full, oily fingered attention.

Trey looked down at himself now, determined to manage greater self-control by understanding what was being done to him. The feelings emanating from his glans were electric; almost too much; sending acute sensations deep into his balls and along his taint. He started to let out little high-pitched winces of pleasure-pain and withdrawing his groin when Phil’s thumb rubbed over his glans. Phil grinned. He knew precisely how sensitive a man’s glans could be, and the fact that Trey’s spent most of the time sheathed inside a protective foreskin made it all the more sensitive. He noticed that clear, glistening fluid was starting to appear in the boy’s slit – precum. It was probably the first time he’d produced it.

Phil took his thumb off Trey’s cock and formed a ring between the thumb and his middle finger, then he resumed jacking the boy very slowly, using the lightest possible touch. At first Trey involuntarily thrust forwards with his groin, desperate for more speed and friction, but Phil simply opened his fingers in response, and when it became clear that the man was not going to play Trey’s game, he slumped back, and let the man continue at his own pace.

Phil continued jacking him; just fast enough to keep the boy’s dick achingly hard, but not fast enough to let him cum. When he saw Trey’s balls, rising high again, he gripped them gently, waiting for the tell-tale pulsations that preceded an orgasm, and when he felt them, he stopped jacking, instead, running a single finger along the top of the youngster’s straight shaft, as though he was petting a small pet, stopping just short of the glans, and continuing until Trey’s balls lowered once more.


Twenty-five minutes after Phil took over, Trey’s face was flushed pink with the effort of sustained excitement, and he was covered in droplets of perspiration from his forehead, all the way down into his sparse pubes, as Phil expertly took him through cycle after cycle of flawless edging, each time stopping right on the edge of an orgasm.

Trey had stopped caring about the cameras, or the fact that he was being jacked off in the company of two men. All he cared about was how incredibly horny he felt. He was constantly air fucking, desperately trying to push himself past the point of no return.

“Gonna cum!” he warned, for the fourth time, and again Phil stopped touching him.

Trey thrust his hips rapidly, violently, ineffectually into the air.

“Awww man, nooo, not again,” he groaned.

William made an observation.

“You know, if you had a dildo in your ass, you could make yourself cum just by clenching your asshole and thrusting like that.”

Trey looked at him and their eyes locked. William’s were gently smiling; Trey’s were intense and wide, and William knew that for a moment the boy was considering it. Then the moment passed. His heterosexual conditioning was too deeply ingrained.

Phil cupped his hand beneath Trey’s groin, but this time it was the twitching erection that he lifted in his palm, while his fingertips repeated the strumming motion William had earlier performed on the back of the boy’s penis, this time of the teenager’s testicles.

“You’re not going cum early are you?” he cooed, with a playful smile. “Surely you have better control than that?”

“Stop,” Trey grunted, “just give me ten seconds to get it together again.”

“Ten seconds, to save yourself three more hours.”

Phil dragged his palm along the underside of Trey’s bone. The frisson was just low enough to avoid pushing the boy over the edge.

“That sounds reasonable huh?” murmured.

Trey’s juicy pink helmet was shiny with lube and precum. Phil wrapped the ring of his fingers around it and started moving over Trey’s pink berry, jacking slowly, but with greater pressure.

“Tell me Trey, how many times have you cum in one afternoon before huh?”

“Uhh uhhhh,” Trey moaned, “I dunno, two, three? Stop, please, I’m too close.”

“Three times huh, that sounds like a lot. How about 10 times? 20? 30? How do you think that would feel?”

Trey frowned at him.

“No, I could never, please don’t make me cum. I could never cum that many times.”

Phil moved his hand faster, faster, lighting fast, the ring of his fingers passing back and forwards across just the glans, never giving Trey a moment’s let up.

Trey grimaced, glancing briefly at the clock.

“No, that’s not fair. I’m so close. You said… ngggguuuhhhh!”

He let out a long, low groan of primal ecstasy, and he fired off a massive streamer of spunk at rocket speed. It shot through the air to Trey’s left, looping and curling as it flew, joined by a second, a third, and more blasts, each firing off before its predecessor had even touched the ground.

Trey screamed, thrashing his hips from side to side, and pumping violently as his expertly-edged dick finally got the release that he was so desperate for. William and Phil had spent the past 35 minutes flawlessly elevating him to an irresistibly high level of excitement. They were masters, and at any time, Phil could have made the boy blow his load, but he knew that the longer he edged him, the more explosive the ultimate orgasmic eruption would be.

William zoomed the camera in on Trey’s face and shoulders, revealing just how out of control the boy’s orgasm was. The boy grimaced as though he was in agony, but nothing could be further from the truth. Soon enough, he’d be able to think about the ramifications of having lost, but for the next 45 seconds, all that mattered was his pumping nuts and his spurting dick. He’d cum hard a few times in his life, but Trey had never cum so hard or so long that he couldn’t even think. It felt like all of his sexual life force was spurting from his balls, and out of his dick!

William turned the handheld to show how far Trey had shot. The kid may not have the biggest nuts, the longest dick, or the thickest cum, but the horny mutt had sprayed a veritable gusher of jizz over 8 feet away from him, landing at a 45-degree angle on the industrial linoleum. William zoomed in to show it to his subscribers. They liked nothing better than to see the results of an over-sexed teenager blowing his load like a hot-water geyser exploding under relentless sexual pressure.

William returned his attention back to Trey. The boy’s face was red and sweaty and his expression was a mixture of relieved shock, and embarrassment. With a playful grin and an exaggerated tone of concern, William said, “Oh deeear Trey, you know what that means…”


  • Trey had watched all the prior videos of straight 19-year-olds being milked. He knew, no he prayed to God Himself, that he would shoot before the 30 minutes.

    Every fiber of his being and every thought he’d had since his balls dropped wanted the torment of dozens of extra-gasms that will follow failing to last the full half hour. Trey knew from biology class in school that hormones were changing both his body and his thoughts. Tossing off had become his passion. He’d lied when he said the most he’d cum in one afternoon was three times. In fact, his all-time cum record was nine with each one producing less and less jizz until the last three didn’t even make anything come out at all – not even a grain of sand or a puff of smoke.

    Now, after having failed, as he knew would happen, Trey was both excited and scared out of his mind that he’d be made to cum so many times over the next three hours that he might never want to cum again.

    Let the show begin!

  • Random Thought Struck Me While Preusing Through Twitter Feed:

    Trey Buying His Calvin Klein Whitey Tighty Underwear.

    Assistant: May I help you find something?
    Trey: Um, I’m turned around. I normally shop online. I’m not used to department stores. But, you see, I need these tomorrow.
    Assistant: “These”? Must be something intimate based on your blushing face.
    Trey: (Thinking about the photoshoot the next day)No, not really. I mean it’s all normal.
    Assistant: “Normal?” You take a deep breath and tell me what you need. I promise no judgment.
    Trey: (About to either leave, faint, or cry) Okay, underwear. I need the kind that I’ve seen….(that was it no more words were coming out of Trey’s mouth).
    Assistant: In porn. You want designer underpants, right?
    Trey: (Not sure if he should run or hug the hunky sales dude) Yeah, but I can’t remember the name.
    Assistant: Just follow me and I’ll help you.
    Trey: (His mind suddenly a bit less cloudy): Calvin, I think that’s the one.
    Assistant: I can show you lots of designer underpants. But, we don’t carry Calvin Klein.
    Trey: Oh, geez. I dunno … I’m not sure … what else…
    Assistant: Are you doing your first porn shoot tomorrow and wanted a pair of Calvin Klein white tight underwear to impress the producers?
    Trey: Well, I … how did you know?
    Assistant: (Putting his hand reassuringly on Trey’s shoulder) I’ve worked here long enough to recognize when a very good-looking guy who turned 18 the day before yesterday needs Calvin Klein underpants for his first porn gig. I’ve done it myself.
    Trey: (Wondering if the Sales Assistant’s hand wasn’t lingering a bit too long on his shoulder) Damn! You have. I’ve seen … I mean…
    Assistant: It’s cool. I’m not embarrassed by it and I’ll do it again, I’m sure.
    Trey: What about the underwear? I can’t show up …
    Assistant: Freeballing?
    Trey: I never wear underpants. I just throw a clean pair in the laundry every day. My mom buys the worst boxers ever. Some polyester crap that I hate.
    Assistant: Come with me to the changing room.
    Trey: I thought you didn’t sell Calvins?
    Assistant: We don’t. But, I’m’ wearing a pair. We’re the same size and I’ll give you mine.
    Trey: I don’t have anything to give you back.
    Assistant: Just bring me my underpants back covered in your cum. Use them as you cum sock for a week and I’ll take that as payment. Just put them in a zippy bag and bring them here.
    Trey: Um, okay.
    — In The Fitting Room —
    Assistant: (Putting his 8″ cut cock back into his slacks) Here you go. One pair of Calvin Klein white briefs. Just remember to bring them back.
    Trey: Do I have to put them on now?
    Assistant: (Again with the hand on the shoulder). It’s up to you. But, you did say you like to freeball. Come with me and I’ll get you a bag to carry them out in.
    Trey: Thanks, I’ll see you in a week.

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