“Sit down, Mike - I’ll get ‘em in.”
Mike had already stood up when he’d seen Nathan approaching, but he stopped, and frowned. “It’s my turn, isn’t it?”
“Sit.” Nathan was smiling broadly. A couple of minutes later he was back with two glasses. He put them on the table, threw a leg over the chair and sat down.
Despite its name, the Compromised Ferret was a fairly old and traditional pub. Mike and Nathan liked it because of that and it also didn’t hurt that there was a gym next door, from which a gratifying number of hot guys came in for a swift one after their workout.
“Cheers.” They took an appreciative sip.
Mike wiped his mouth with the back of his hand. There was a quizzical smile on his face. “What are you so happy about? You look like a cat with two tails.”
Nathan’s grin got even wider. “There ought to be a word for what you’re doing at the moment.”
“Frowning and smiling at the same time. ‘Smowning’? ‘Friling’?”
Mike looked at the boy as if he was mad. “What the fuck you on about?”
Nathan glanced around conspiratorially and leaned closer, his eyes twinkling. “I’ve won the lottery.”
Nathan nodded. “I, my friend, have won the lottery.”
Nathan nodded again, faster.
Mike stared. “Nah, you’re bullshitting.”
“Nope five thousand.”
“Straight up?” Nathan’s mouth was hanging open. “Well fuck me sideways with a bargepole. You sure?”
“Oh yes. Five thousand quid. Tax free.”
“Bloody hell.” He was silent for a moment. “What you gonna do with it?”
“The first thing I’m gonna do is treat myself. You know Jamie?”
“Jamie…” Mike thought for a moment. “Black spiky hair, muscles? I see him around, never played with him.”
“Yep. You have no idea how fucking much I fancy that boy. He’s never shown the slightest interest though. But I’m gonna have a night with him. I’ve made him an offer he couldn’t refuse.”
“Didn’t know he was rent.”
“All boys our age are rent if you pay us enough.”
Mike nodded at that, thinking back to his own past. “True. So, when?”
“Friday.” Nathan picked up his pint again. “I can’t fucking wait.”
He was lying on his bed, his legs strapped tightly together at the knees, the leather cuffs on his ankles clipped together, and the ones around his wrists roped to the top corners of the bed frame. The only thing he was wearing was a pair of skintight stretch denim jeans. They were his tightest and most stretchy, the denim faded and thin both from wear and from the washes that were necessary to get rid of the frequent spunk stains. They were already bulging at the crotch.
Very carefully, Jamie unzipped them and extracted the hard cock. He sat on the bed and took it between his thumb and two fingers. With a knowing smile, he began to stroke it slowly.
The feel of this gorgeous guy’s hand on his cock was wonderful, but still Nathan felt disappointment for a moment it was gear that he was into, and he’d told Jamie that.
As if reading his mind, Jamie smiled. “I know,” he said, “you want gear using on you. Don’t worry it will be. Tonight is going to be all about that. We haven’t started yet; but this bit is important it has a very special purpose. You’ll see what it is very soon.”
Nathan nodded, curious as to what this ‘special purpose’ could be. He lay on the bed, enjoying being helpless at last in the hands of the boy he’d fancied like fuck for so long. But being worked on by this drop-dead gorgeous hunk was rapidly becoming too much for him. He gazed at Jamie’s muscles under his tight tee shirt, his flat stomach, the shape of his hips and his bulge in those jeans, and he felt himself getting ready for orgasm.
Jamie smiled, and removed his fingers. He tutted. “You’re paying me three hundred quid for this so you don’t want to be cumming just yet, now, do you?”
Last week when he’d arranged this with Jamie, Nathan had told him exactly and precisely what he wanted. He’d also written everything down in a list. A comprehensive list. The main and most important item on it had been the fact that what he wanted most of all was to feel like he was being raped but with his cock being the target of that rape and not his arse. He wanted to be forcibly made to cum while he was fighting against it. And it was important that this was being done to him by someone who was strongly motivated to do so.
Jamie had looked at the list, thought about it for a while, and had eventually nodded. “For three hundred quid I can certainly do that to you, mate. But you said I should be motivated to make you cum. How about an extra fifty quid for each time I make you lose it?”
That was a lot of money a lot more than he’d intended to spend, Nathan had thought. But his cock had jerked at the thought; for fifty quid a time Jamie really would try to make him lose it, and he himself would have even more reason to resist. He had been rock-hard in his jeans as they had agreed on it.
Jamie gently gripped the hard cock again and resumed the very slow stroking.
Nathan closed his eyes and moaned in pleasure. “You’re making me need to cum, you sexy bastard.”
“I know.” As his fingers continued to explore the cock, Jamie was paying very close attention; he was looking for spots or techniques that were especially effective on this lad. He found one when his fingertips were sliding the foreskin backwards and forwards over the head. It seemed that the closer he got to the very end, the more Nathan groaned and thrust. Now that was interesting, he thought.
The boy was right on the edge again, so he stopped.
“Fuck! Don’t stop! I need to fucking cum.”
This time Jamie didn’t say anything, just continued smiling. He waited for a few seconds and then resumed his slow work on Nathan’s cock.
Moments later Nathan was back on the very edge of cumming. “For fuck’s sake! I need to cum! Please!”
Jamie stood up and walked over to the computer. He saw that it was already switched on, so he came back and stood at the end of the bed. He tapped a fingertip thoughtfully on the top of the iron footer. “You gave me a list of what you’re into when we arranged this,” he said slowly, “but I’ve been doing a bit of research of my own since then.” He bent down and gave the boy’s cock another few gentle strokes, making him arch his back and thump his fists into the mattress in frustration. “For instance, I hear that you recently came into a bit of money…”
Nathan blinked, then considered the implications of this for a few seconds. Well, if Jamie knew, there was nothing he could do about it now. He reluctantly nodded.
“You want me to force you to cum while you’re struggling to stop me, don’t you?”
Nathan’s cock jerked as that beautiful boy said those words. Oh shit, the thought that Jamie was going to be doing that to him was wonderful. “Oh fuck yeah.”
Jamie chuckled. “Well I’ve been thinking. Seems to me that it would be better still if we both had a bit more motivation. Fifty quid for each time I make you cum is not a lot. So, I’ve decided on a thousand quid each time.”
Nathan stared. “A thousand? Fuck off!”
He took Nathan’s cock between his fingers again and resumed teasing it but this time concentrating on just the end of the head. That seemed to be what got to the boy most of all. And it appeared to be so: there was an urgent intake of breath, and Nathan was immediately back on the edge, his head moving frantically from side to side in renewed desperation.
“Think about it. If you stand to lose a thousand quid every time, you’re gonna try a fuck sight harder to stop me from making you cum, and believe me, for a K a pop I’m gonna make fucking sure you can’t stop me.”
Jamie’s fingers on his cock were making it very difficult to think logically but fuck, he was right: the increased stakes would make the whole thing unbelievably horny. But on the other hand losing a thousand pounds every time was unthinkable. No way could he afford to do that.
He shook his head again. “A thousand a time? Forget it. A hundred. No more.”
Jamie smiled. He circled the tip of Nathan’s cock gently with a single fingertip for a few moments, and then resumed sliding the foreskin over it slowly. “A thousand pounds every time, Nathan,” he whispered. “For that, you’ll fight like fuck to stop me. But I’ll make sure you fucking can’t, boy. I’ll make you shoot your spunk helplessly into those skintight jeans…”
The words had exactly the effect on Nathan that Jamie had intended: he moaned and writhed on the bed.
“Tell me when you’re ready to agree and I’ll get started on making you cum in those jeans.”
Nathan was still shaking his head, though less violently now. And his voice was much less certain. “Fuck off. I’m not giving you a th-” He arched his back and gasped as Jamie’s finger stroked once directly over the piss slit. “Oh fuuuuuck…”
Jamie was amazed at the effect this was having on Nathan; he’d edged enough guys in the past to know that if he worked on the boy for long enough the need for orgasm would eventually become so compelling that it would force him to agree to the arrangement or anything else for that matter - just to be able to cum, but this was turning out to be so much easier than he’d expected. He continued to work leisurely on the desperate cock right at the tip, now - being very sure to stop every time Nathan was on the point of cumming.
When someone has his finger right on your pleasure centre there is only so much that you can take. Nathan was beyond that point now, but the edging still didn’t stop. He was beside himself with the need to cum and it was getting worse by the second.
After a further five minutes of this, Jamie thought that the boy was ready; much more and he’d go insane. He teased the very tip of the precum-dripping cock head with a single fingertip, hardly touching. “Now, just tell me your PIN number and once I’ve checked it’s the right one, we can start.”
Nathan was so close that orgasm was the only thing he was capable of thinking about; if he didn’t cum now he knew he would go out of his mind. He had never in his life been this ragingly horny before; he would do anything to be able to cum. This had to stop now. It was almost impossible for him to concentrate on what Jamie was saying, but the fact that it was a way to end this unbearable edging got through to his brain somehow. He managed, finally, to nod his head.
“Good…” Jamie’s fingertip explored slowly and gently over the edge of the boy’s foreskin. “What’s your bank PIN?”
It took a few moment for Nathan to be able to get anything coherent out, but after a couple of tries he managed. “Three… six……. onefive!”
“Excellent. And where’s your card?”
“Wallet at the s… side of the com-com-com… puter.”
Jamie gave the cock shaft a little squeeze and stood up. “There’s a good boy.” He found Nathan’s banking app on his computer, and picked up the card reader that was lying on the shelf. Half a minute later he was in, and looking at the boy’s balance. He smiled, and logged out, then wrote the PIN down on a pad on the desk.
“Now we wait for you to go off the boil a bit gotta give you a fighting chance after all and then battle will commence.” There was a shelf of books above the computer desk, and he spent a few minutes looking through them and reading the reviews on the backs.
When he returned to the bed Nathan was still hard, but no longer anywhere close to cumming. Jamie carefully put the boy’s cock back inside his stretchy jeans, pushed it hard over to one side, and zipped them up. The bulge was eye-watering.
He knelt on the bed and unfastened the wrist cuffs. There was no chance that Nathan would be able to escape Jamie was a strong lad, and anyway Nathan’s knees and ankles were still restrained. He rolled him over onto his front, then tied the leather cuffs that were around his ankles to the ones on his wrists, and pulled them into a tight hog-tie. Having made sure that the knots on the rope were well out of the reach of Nathan’s fingers, he turned him back onto his side, facing away from him.
“God, those jeans are tight,” Jamie murmured. “And stretchy. And thin. I bet you can feel the lightest fucking touch through them…” His fingers began to trace patterns over Nathan’s legs. Sighs and moans came from the boy. Now and then Jamie’s hand explored briefly between his closed thighs, retracting every time Nathan - with an urgent gasp - squeezed them together harder to try to keep the invading fingers out. He teased the backs of the knees, ran a finger down the seam separating the round arse cheeks, worked on the fronts and backs of the legs.
After a while his hand again explored the dark, warm, denim-smooth valley between the boy’s thighs. It stayed there for a few seconds, teasing and tickling, and Jamie made a mental note of the extreme reaction it caused. Over the next few minutes he worked on the boy non-stop, and from different directions, occasionally rolling him over so he could get to bits he hadn’t been able to reach, but for now he kept off the hard bulging cock.
His hand was between Nathan’s thighs again. This time, though, it would not be stopped. Bit by bit it worked further in squeezing frustratingly slowly between the now frantically-struggling boy’s tightly-clenched muscles; muscles that were incapable of keeping it out until Jamie’s fingers came into contact with the warm mound of Nathan’s balls. The hand stopped, and the fingers began to tickle.
Nathan was cursing and kicking fit to bust and doing everything he could to get the hand out from between his legs, but the hog-tie made that impossible. He started to yell. “Get off, you fucking bastard! Fucking stop!”
A quiet chuckle. “Well stop me then. If you can.”
Nathan was fuming. There was nowhere he could move to get those fingers out from off his balls. And he was getting dangerously horny again very quickly.
The boy was making a lot of noise, so Jamie pulled his hand out and stood up. He opened the large backpack he’d brought with him, and rummaged around for a moment. When he came back he was holding a leather gag. Kneeling astride the boy he got the gag strapped in place in spite of Nathan’s efforts to throw him off. Then he knelt behind him again. This time he forced his flat hand straight between the tight denim thighs and immediately back onto his balls. Nathan yelled into the gag, and the fingers resumed their tickling.
Because Nathan’s knees were strapped together, his movements were limited even more than by the hog-tie alone: he was unable to push himself over to escape what Jamie was doing to him. All he could do was try to kick and turn as much as he could, but that was by no means enough. The fingers worked on him through what was one of his most powerful fetishes skintight jeans. His cock was rock-hard and pushing the stretchy denim out into an all-too vulnerable, grippable bulge. He took a sharp breath as he felt Jamie’s other hand begin to work its way between his stomach and the top of his thigh. His struggling increased and he curled up even tighter as he tried desperately to keep it out, because he knew exactly where it was heading.
The fingers reached his bulging cock. For a while they ran over the shaft, tickling lightly through the thin jeans, then they took the cock head between them not moving at all, just holding it still, very gently.
Nathan’s face was screwed up in concentration. He was not going to let this bastard take a thousand fucking quid from him. No fucking way. But the feel of being got from the front and from the back at the same time was overwhelming. He couldn’t get away from it wherever he moved one hand was forced between his thighs, tickling his balls, the other was just holding his cock head, telling him in no uncertain terms how easily Jamie could make him lose control whenever he wanted to. To Nathan, that was so fucking horny…
“A thousand quid coming up - unless you can stop me making you cum…” Jamie’s voice was quietly gloating. Very carefully he positioned his thumb and first finger either side of the bulge of Nathan’s cock head, towards the top; then he closed them together, which pushed the cock back under the denim and caused the foreskin to slide forwards over the end of the head. When he opened them, the springy cock pushed up again and the foreskin slid backwards once more.
Nathan’s head shook from side to side and he yelled into the gag as Jamie’s fingers opened and closed repeatedly and quickly. He’d lose a thousand quid if he let this bastard make him cum, but the feeling of his cock sliding under the tight, stretchy denim jeans, and the foreskin moving with each stroke, was fucking irresistible. He increased his struggling, trying everything he could to get those fingers off him, that arm out from between his thighs - he kicked his feet, he tried to turn over, he punched fresh air behind his back with his cuffed hands but everything he did only made it feel more horny, made him more conscious of being helpless. He squeezed his thighs together as hard as he could, but the more he fought the more he felt like he was being raped, which of course was exactly what he’d been after to begin with. Nathan struggled like fuck, but he couldn’t get away from it, and he couldn’t prevent it.
Jamie’s fingers stopped. The hand that had been tickling between the boy’s thighs now burrowed deep into his groin and gripped the base of his balls firmly. At the same time Jamie held Nathan’s cock head stationary with his thumb, and used his first finger to rub slowly round and round directly over the very tip of the head.
Nathan almost went cross-eyed. The fingertip was only moving slowly, and hardly pressing at all, but the tight denim over it was so thin, so sensitive and so soaked with his precum that wherever it touched, it transmitted pure pleasure so acute that it bordered on pain.
Jamie’s voice whispered into his ear: “A thousand quid. Don’t let me make you cum. Fight it. Fight against it…” Then a chuckle. “But you can’t, can you…?”
Nathan lost it completely. He struggled like crazy and tried to stop the onset of orgasm but this was exactly what he’d fantasised about so often. He screamed into the gag, his muscles tensed, his hips thrust, and a spike of intense pleasure shot through him as he gave himself up to an ejaculation that was, for him, pure fetish. His cock was being raped in his skintight jeans. He came uncontrollably, his spunk jetting out and soaking into the stretchy denim.
Even before he’d completely finished cumming Nathan was beating his head into the pillow in fury. He’d been totally and humiliatingly controlled, and absolutely unable to stop himself from losing it. He’d done everything he could, but it had made no difference he’d been fucking helpless with that boy’s hand forced between his thighs, gripping hard just behind his balls, the other milking his cock - that had just been fucking impossible to fight against. And the way the bastard had done it - so slowly, moving that single finger so infuriatingly leisurely, knowing that Nathan stood no fucking chance whatsoever - that he was incapable of resisting a movement even as tiny as that. It had been a demonstration of just how much he could be controlled.
That feeling of humiliation reached a new peak as Jamie kept his hands there long after the boy’s orgasm had finished: one buried deep between the warm thighs, and the other still gently stroking his cock head through the slippery dark-blue patch of denim. “Fucking helpless to stop me, boy,” he gloated.
That was the first time in his life Nathan had ever really been forced to cum against his will, and he had fucking loved it. Oh fuck, had he ever.
Jamie removed the boy’s gag. He smiled as he got off the bed and made a sound like a cash register. “Ker-ching. One thousand pounds. Thank you. I hope you’ve got plenty more spunk left in you I’m gonna get a lot more than that tonight.” He wrote ‘£1,000’ in large letters on the pad by the computer and held it up so that Nathan could see it.
“Fucking bastard,” was all that the boy could manage.
Jamie grinned; a thousand fucking quid. This was so easy and there was more to come; he intended to make very sure of it.
As the waves of pleasure ebbed and Nathan’s breathing returned to normal, the full import of what he’d agreed to hit him. The five thousand he’d won was not really that much, and it wouldn’t take many orgasms to make a large hole in it. He was already down to four thousand. With his cock slowly softening, he began to fume at the unfair bastard doing this to him. Yes, being made to cum against his will was a long-time fantasy of his (he wanked thinking about it in different scenarios just about every night) but he could not afford this. He’d never had that sort of money before and there were a lot of other things he really wanted to do with it. He was damned if he was going to give it away to this bastard. He looked up at Jamie the boy was laughing quietly at him - but the hunk was so fucking hot. But that was it. He’d cum once, and it had been good, a lot more than good. But that was going to be it.
While the boy was recovering on the bed Jamie looked through Nathan’s wardrobe, and found a shelf with a few sex aids on it: there was a very thin butt-plug; a tube of lube; a kind of hood or long blindfold that by the look of it had been home-made out of the remains of a pair of leather jeans, and some new-looking shiny black nylon Adidas boxing shorts with red stripes down the sides. He smiled hmm, those were sexy. He sat down at the computer desk again, took out the list Nathan had given him, and read it again, carefully. So far it was proving to be remarkably accurate. The boy had major fetishes for leather, shorts and skintight jeans; for being helpless; for struggling. Having his legs together made him a lot more horny than if they were apart; he loved being got from behind that was certainly true judging by the way he’d reacted during the hog-tie and he wanted to feel invaded. What could that mean? Nathan wondered. He looked again at the boxing shorts; the fact that those were on that shelf must mean that the boy found them a special turn-on. And boxing shorts were loose: that would be perfect for invading, he thought. Hmm. Ok. Ideas were forming.
Returning to his backpack on the floor he took out a pair of thick, fingerless leather mitts, and some thin but strong ropes of various lengths. Next he looked around the room. He needed restraint points. He’d expected there would be some somewhere, and sure enough, he saw strong screw-in eyelets at each corner of the door frame, another in the middle at the top, and one halfway down each side. That would do nicely.
It was only minutes since he’d made Nathan cum in his jeans, but Jamie was impatient to get more cash. He unfastened the boy’s restraints. “Strip,” he said.
When Nathan had finished struggling out of his skintight jeans, Jamie picked up the boxing shorts. “Put those on.”
Nathan took them with some reluctance he was well aware of how pervy the unlined shorts felt, and the thought of Jamie intending to use them to make him cum was both mind-blowing, and also very worrying.
The shiny black nylon boxing shorts came down to within a couple of inches of his knees. The waist fitted perfectly and the legs were very loose. Jamie pulled the leather mitts over Nathan’s hands, re-buckled the cuffs around his wrists and ankles, then positioned him in the door frame and secured him to the corner eyelets as tightly as possible. He passed a rope around each thigh just above the knee, and tied it to the ring in the side of the door frame to stop the boy from being able to close his legs.
Jamie slowly peeled off his tee shirt and stood with his hands on his hips, looking at him. With the round leather mitts on his hands, and in those shorts, he looked like he’d just stepped out of the boxing ring.
The sight of the sexy, muscular hunk he’d fancied so much for so long standing there wearing nothing but tight faded jeans was heaven. No! For fuck’s sake stop thinking like that! You’re already down a thousand fucking pounds and there’s only four left. Don’t look at him. Don’t get horny. And for God’s sake don’t fucking cum again.
It was as if Jamie could see into his mind. The expression on the hunk’s face said it all: I’m gonna make you cum again and again and there’s fuck all you can do about it. And I get a grand a time for doing you.
Jamie got the gag off the bedside table and strapped it back onto the boy, then pulled on a pair of tight leather cop gloves. He smiled - a slow, knowing, teasing smile and took a few steps closer. Nathan pushed as far as he could forward, desperate in spite of his better judgement - to feel that boy against him, but there remained just an inch of space between them. Jamie’s lips approached Nathan’s gag, and brushed it lightly. Nathan was fuming: he was desperate to kiss the hunk and he couldn’t. Then Jamie raised his gloved hands and began to stroke them over the boy’s shoulders, arms and chest. Nathan’s eyes half-closed as he breathed in and moaned in pleasure. Despite the fact that he’d cum not long ago, his cock was hard again and tenting the front of the loose shorts out.
Having reached the boy’s stomach, Jamie crouched down and began to stroke Nathan’s legs. He ignored the area covered by the shorts completely didn’t touch the boy anywhere there even once. This went on for some time.
He guessed that by now those shorts would be feeling like protection: the area under them had not been touched at all, whereas the rest of Nathan’s body had been stroked and caressed all over repeatedly by his leather-gloved fingers. He hoped that because of that, what he was going to do now would be even more effective.
As he had done several times before, he began at the inside of Nathan’s calf, his fingertips teasing and tickling lightly. Slowly he moved his hand upwards, past the knee, until he got to the edge of the black nylon. Here, as before, he paused for a few seconds but instead of continuing on the boy’s stomach as he had done previously, this time he suddenly thrust his hand up inside the leg of the shorts, tickling the thigh quickly on the way up to the boy’s balls. Nathan yelled into the gag and the side ropes snapped tight as his knees came together as far as the restraints would allow in an involuntary panic reflex to keep the tickling, invading hand out. But the ropes kept his knees a few inches apart and try as he might he couldn’t close them together to protect himself. The unimpeded fingers teased his defenceless balls up the shorts and stroked briefly along his cock, making it jerk urgently, then the hand came out. Nathan was panting oh shit, oh shit, that had felt so fucking humiliating, so fucking horny.
Three more times Jamie did the same thing, first on one leg and then on the other. Now that Nathan knew what was coming, his leg muscles were trembling each time as he waited for that invading hand to go up the shorts. It felt both unbearable and indescribably erotic to him.
“Hmm.” Jamie removed the side ropes.
Now that his legs were no longer restrained except at the ankles, Nathan’s knees slammed together as the leather-gloved hand went up inside the shiny shorts yet again. Shit that was even worse than when he hadn’t been able to close them together.
Nathan was actually very embarrassed about this fetish of his for being invaded whether being got through jeans from behind, between his legs, or up inside shorts, or anything else and he’d never before told anybody about it. He would have died if any of his mates knew about it it was just too personal, too pervy, it even seemed ridiculous . Even in the list of things he’d given to Jamie, he’d not been able to bring himself to be specific about any of it but Jamie seemed to have worked it out for himself and was intentionally using it as a weapon against him. That blew his mind, but it also embarrassed the hell out of him. And that , he found, was making it even more effective than he could have dreamed.
Again and again the hand invaded the boy’s shorts and every time was as humiliating and as unbearably horny to him as the last.
For some reason Jamie had liked it a lot, earlier, when the boy had been hogtied and he’d been working on him from behind him. One of the things in Nathan’s list was ‘being got from behind’, although he hadn’t known exactly what the boy had meant by that when he’d first read it. Initially he’d thought he’d meant being fucked, but the list said that fucking was not required at all. The hog-tie session had made things much clearer. He pushed himself through between Nathan’s spread legs, and knelt behind him. Then he started to tease and tickle the boy’s thigh again below the bottom of the shorts. Again his hand moved slowly upwards. Nathan was ready for the thrust up the leg, but it didn’t come; instead the fingers continued to tease across his skin so lightly hardly touching - and gradually moving deeper up under the leg of the shorts.
This was pure sexual torture for Nathan. Whatever position he could get himself into made no difference: the hand still continued upwards, the fingers stroking the ticklish front and inside of his thigh higher and higher and because it was being done from behind him, the rate at which it was becoming more unbearably ticklish and erotic was exponential.
It was impossible for him to keep still; he was writhing uncontrollably in the restraints. He could also feel the unlined, shiny nylon sliding over his skin and his cock every time the hand moved - it was as if the sexy shorts were working with the bastard to make him need to cum.
Whenever Nathan closed his knees together it put more of his weight onto his wrists, and that hurt, so he couldn’t keep them closed for long. Because of this he tried to fight the urge to close them as much as he could; but every time, as the tickling, teasing fingers rose higher and higher, it got more and more difficult. There inevitably came a point where he lost control: he gasped and his knees came together involuntarily again. This only made things worse for him because now Jamie’s hand was squeezed between his thighs, and that alone felt so fucking invasive and horny that it made him need to cum even more. Because his ankles were held apart by the cuffs he could only just make his knees touch, and he still couldn’t hold them there for long, so Jamie was able simply to wait until the boy’s muscles tired, and then push his teasing hand further up between his thighs - and there was nothing Nathan could do to stop it.
The boy’s cock was moving around, the tip sliding lightly against the shiny nylon shorts, leaving trails of precum on the inside surface, the fingers were tickling his balls unbearably. Oh shit that felt so pervy, so unbelievably fucking horny . Fuck, he needed to cum every bit as much as when the bastard had been edging him earlier.
This boy was seriously into loose shiny shorts, Jamie thought. He himself usually preferred shorts to be tight if guys were going to wear them, but this was different and interesting. Hmm. This boy also had a fetish for leather. I wonder… He slid between Nathan’s legs again and went back to the backpack. From it he took his leather jeans, then returned to his position behind the restrained boy.
Was it too soon to make him cum again? Jamie wondered. Nah. Fuck it. Get another thousand quid.
He pulled a leg of the jeans over his hand and lower arm. His voice was a sadistic animal grunt: “Gonna make you cum, boy. There is no fucking way you’re gonna be able to fight against this…” In one smooth motion he pushed his leather-covered hand up the leg of the shorts. A loud, urgent gasp of pure lust came from behind the gag and, as expected, the boy’s knees slammed together but before they met, Jamie had got his hand between the tops of Nathan’s thighs. Pushing and twisting his hand back and forth, he forced it further through between the straining thigh muscles that were fighting to keep it out, until he had enclosed the boy’s balls in cold black leather, and was gripping them through it. Reaching around Nathan’s waist he found the desperate cock and gripped just the head gently through the shiny shorts. Then he began to milk it.
Jamie tried to curl up; he threw himself about and struggled like fuck, desperate not to lose another thousand, but the bastard seemed to know exactly which buttons to push. These shiny shorts always got him horny anyway, but having them used by this hunk to make him lose control and cum while he was helpless to do anything about it was a fantasy so perfect he’d never even considered it. The feel of the leather up inside them was unbelievable, and the moment Jamie’s fingers began to milk him he knew he had seconds to get control of himself or it would be too late. He twisted and struggled, he fought to concentrate on not cumming, but the feel of the cold leather between his thighs, up his shorts and gripping his balls - and the shiny nylon sliding over his cock under the bastard’s fingers - was much, much too irresistible. If Jamie had been milking him fast he’d have cum instantaneously, but the stroking of his cock head was slow enough to prolonging it, forcing him to try to fight against it. And for about ten seconds he did fight: willing himself not to cum, bouncing around in the restraints, thrusting, writhing, twisting, kicking, struggling, and screaming into the gag while Jamie worked on him slowly and irresistibly, his hands following the boy’s manic movements easily. Then, seemingly without trying, the leisurely milking fingers got him; they demolished his willpower and he experienced an orgasm more intense than he thought possible. Spunk ran down the inside of the nylon and dripped onto the floor as he yelled and jerked and swore into the leather gag.
As he had done when he’d made him cum in his jeans, Jamie continued to work on the boy - but even more slowly and gently - long after he’d finished cumming, and it was when he did that, that Nathan experienced the most intense embarrassment and humiliation. It was as if the bastard was doing it intentionally, rubbing in the fact that he’d been helpless to fight against his fetishes or against Jamie.
Jamie laughed. “You are so fucking easy,” he said as he finally took his hand out of the shorts. “Well, that’s two thousand I’ve made already. I think you need a rest before the next one though.” He slid back to the front and went over to the computer desk.
‘£2,000’ replaced the ‘£1,000’ on the pad.
He took something else out of the backpack but kept it behind him as he stood close in front of the boy again. Unbuckling the gag with one hand, he dropped it on the floor. His tongue licked slowly over Nathan’s lips. “D’you fancy me then?”
Nathan was still breathing hard from his orgasm. He nodded. “ Oh fuck. You have no fucking idea.”
Nathan groaned as the muscular hunk put his arms around him and kissed him properly. He’d been praying that Jamie would do that since the start of this. Then he brought his hands up behind the boy’s back and quickly pulled the hood over his head. Nathan grunted in surprise as the cold black leather enveloped him.
Jamie positioned the hood then moved the boy’s head down so that he could close it, pulling the laces as tightly as he could, zipped it up, and secured the collar strap. Nathan had never worn a hood like this before it was very heavy, thick black leather, it pressed over his eyes, and it was intended to feel as confining as possible. Quiet moans of pleasure came from inside and, had he not cum so recently, he was sure that just the feel of it would have got him hard again.
Jamie unfastened the lower cuffs for long enough to get the boxing shorts off, then refastened the restraints. He wiped the boy’s cock with a tissue.
“You rest for a while. Make some more spunk for me ‘cos I’ll be extracting it from you when I come back.”
After removing the leather gloves, he went through into the living room, found the kitchen and made himself a cup of coffee. He took it to the settee and settled down, picking up one of the bike magazines that were on the table. This was strange, he thought he didn’t share any of Nathan’s special turn-ons or fetishes (well, he liked leather and he’d brought some with him to use on the boy later - but with him he’d hardly call it a fetish), and yet he was actually quite enjoying exploiting Nathan’s weaknesses. There was something satisfying about it. Odd. He opened the magazine and started to read.
Having cum for the second time only minutes ago, Nathan didn’t feel in the least bit horny any more. Inside the hood, he was frowning. Normally he didn’t cum that easily it usually took him a fair time but he’d shot his load helplessly twice so far. That annoyed him a lot, but losing two thousand pounds annoyed him even more. It had been a mistake to tell Jamie his fetishes, he decided it was so fucking unfair of him to use them against him like this. First the jeans and then the shorts. Yes, that had been exactly what he’d wanted but a thousand pounds a time? That was just taking the piss. And yet theoretically it had been within his power not to lose that money: if he had just fucking controlled himself and not cum he’d still have it. But he hadn’t been able to control himself. He’d cum helplessly when Jamie had pressed his buttons. Did he really have that little self-control? The frown deepened. That would not happen again. He’d regroup, get himself together. He was not going to lose another fucking penny to that bastard.
The hood whistled as he breathed out in fury, and the sound brought his mind back to the feel of the leather over his face. It felt wonderful pressing tight over his eyes, his mouth, and head; it smelled strongly of leather too. Made him feel helpless, and that was something he’d loved for as long as he could remember.
He wondered what the bastard was doing it must have been at least half an hour since he’d left him standing there, restrained in the doorway. Was that a noise? Had Jamie come back into the bedroom? He held his breath, listening intently, but the thick leather cut out a lot of sound. He heard nothing more. If only he could see . He tried to reach his head with a hand, but he couldn’t and anyway Jamie had put thick leather mitts on him so he couldn’t use his fingers. There was no way he could get the hood off and even the thought of that was horny. Stop thinking like that!
The sudden whisper close to his ear sent a shock through him and made him squeal in surprise.
“Do you know what I’m wearing, Nathan?”
The hooded head shook from side to side.
“Motorcycle boots, skintight black leather jeans, studded leather bike jacket and shiny, thick black leather gauntlets with studs on the cuffs. You wanna see?”
Now Nathan’s head moved up and down very urgently indeed. Oh fuck yes, he wanted to see very badly indeed. The thought of that gorgeous hunk in leather was blowing his mind.
There was a quiet chuckle. “But you can’t see through that hood, can you…?” A hand pressed the leather even tighter over his eyes.
Why did Jamie have a knack of saying things that turned him on, for fuck’s sake? Nathan made a noise like a wounded dog. “Mmmfleasefff!” He begged.
“Nope. But you can feel me.” He brushed a booted and leather-jeaned leg against Nathan’s bare skin for a moment. There was a gasp from the boy, and he tried to make contact again, but he only met fresh air.
Jamie waited for a few seconds and then, without warning, he embraced Nathan tightly, squeezing the naked boy against him, letting him feel the cool black leather all the way down his body, and the bite of zips and pointed chrome studs on his flesh.
The groan this time was louder and much more urgent. Jamie could feel Nathan’s now solidly-erect cock pushing against his own leather bulge and it felt good. “Now, I’ve already made two grand outta you, so I’m thinking I should give you more of a chance to fight me for the next one. So I’m going to tell you exactly what I’m going to do to you, so you can decide how you’re gonna fight against it.” He took a step back, out of contact.
Nathan wanted to bash his head against a wall: a minute ago he’d not been horny, and he’d been determined and confident that from now on it was going to be he who was in control of his body, not Jamie. But now his cock was completely hard again and he was, as before, putty in the bastard’s hands.
“I’m going to fasten your hands behind your back, pull them up to the ring on the top of the door so you’re forced to bend forwards with your feet still held apart by the bottom cuffs. Then I’m going to stand at your side, with my booted feet astride your leg so you can feel my tight leather jeans. I’m going to force one hand between your legs from behind, to grip your balls. You won’t be able to stop yourself from closing your thighs together tight, around the leather gauntlet, so you’ll feel it squeezed between your legs, the cold studs on the insides of your thighs. I’m gonna hold your balls while I take your cock in my other hand and make you fucking cum by working just on the head of it. Hooded, helpless, having your fucking cock raped in a way you can’t resist by a boy in black leather that you fancy like fuck but you can’t fucking see. You think you can fight against that? Stop yourself from losing another thousand quid?”
Nathan was shaking his head and shouting repeatedly into the gagging hood. “Mph! Mnoooo!”
Jamie released Nathan’s wrist cuffs, clipped them together behind his back and pulled the rope up so the boy was in position. He lifted one booted foot and stood at Nathan’s side. “You ready for this? You gonna stop me from making you cum again? From getting another thousand quid from you? Yeah, try, boy…” He waited for ten heartbeats, then roughly and without warning he pushed his hand through from behind and grabbed the boy’s balls. As he’d expected, Nathan’s knees came together involuntarily, trapping his arm there, squeezing the cold, studded leather gauntlet between the insides of his thighs. Jamie gripped just the head of the boy’s cock with his other hand and milked it hard and fast.
Nathan was hooded, he could feel Jamie’s leather-clad body at his side, studded black leather between his thighs, leather fingers gripping his balls, and a hand milking his cock head. Despite the fact that he’d had three orgasms already, all of this - plus the knowledge that Jamie was determined to make him cum no matter what - overcame any self-control he might have hoped for even before he could think about resisting. He didn’t have time to begin trying to fight against it, and with a long, drawn-out howl, he came for the third time that evening.
Jamie coated Nathan’s cock with his spunk and continued to stroke it slowly for a good minute after he’d stopped cumming, as if to underline the boy’s failure. Nathan’s head was hung in humiliation.
Jamie released him from the door frame, re-connected his wrist cuffs behind his back, and lay him on the bed. “Well that was the easiest yet. Your spunk must be worth its weight in gold - I’ve got three thousand quid’s worth of it already. And I’m gonna get more of it, believe me.”
On his way into the kitchen he changed the number on the pad to read ‘£3,000’.
Another coffee, another magazine. Jamie didn’t fancy Nathan much, but he was surprised by how horny he was finding it all. The idea of making this boy lose it despite everything he could do to stop himself was a lot more interesting than he’d thought it would be, he decided. The boy was just so deliciously vulnerable ; he had no defence whatsoever against weaknesses that could be used against him so easily. The fact that he was getting a great deal of money out of this was great, but he realised that it wasn’t only that he was fucking getting off on it. He wanted to find other ways to destroy that boy’s self-control; he wanted to see him trying to fight against it as hard as he could and losing.
The feel of the leather against his naked skin felt good too. Idly he played with his cock bulge while he read. He’d had these jeans for ages he’d bought them a few years back, to go with the studded jacket he’d been given. They hadn’t seen much use as they were substantially tighter than the sort of thing he usually wore, but he realised that for use against a boy like Nathan whose cock seemed to be controlled by skintight jeans and leather they were, in fact, perfect. He was looking forward to seeing the boy’s face when he took his hood off and he saw him in leather for the first time. He should really wear it more often, he thought; it not only felt horny, but he’d been surprised to find that it made him feel fucking sadistic at least with Nathan - and he liked the feeling a lot.
And then there was the money. Three thousand pounds - so far. He daydreamed for a while about what he was going to spend it on.
“How you feeling? I’m gonna milk some more cash outta you.” It was an hour later.
Muffled noises came from the boy.
Jamie pulled Nathan up and sat him on the side of the bed, then removed the hood. He walked around to stand in front of him.
Nathan stared open-mouthed - it was the first time he’d seen Jamie in leather, and fuck it was the sexiest sight he’d ever seen. The thick leather jacket was heavily studded and zipped halfway up, beautiful pecs visible under it, and the collar was turned up; the boots were big and chunky with lots of straps; and those leather jeans were skin-fucking-tight. Nathan felt a physical compulsion to feel him and lick him all over - and kiss his lights out. His cock felt a bit sore, and a few minutes ago he hadn’t thought he’d ever be able to get horny again (that was a good thing he’d lost three thousand quid already and he just couldn’t lose any more, gorgeous Jamie or not). And yet the sight of the boy in front of him still made him feel like jelly.
Jamie unfastened the wrist cuffs and removed the mitts. “Lie down on the bed again.” He waited until Nathan had done so, and then lowered himself slowly on top of him.
“Oh fuuuuck….” Nathan wrapped his arms around him, pulled his head down and they kissed. His hands were all over the hunk, feeling his leather jacket, the zips, the studs, his belt.
After a while they rolled over so that Nathan was on top. Now he could lick and kiss Jamie’s leather jeans, his jacket, his boots, and his bulge. He could feel hard cock in there, and he set to work on it with his teeth and fingers through the leather. This got Nathan rock hard again within five minutes. “Oh shit, you are so beautiful,” he whispered.
Jamie moved the boy off him and lay at his side. He pushed one booted foot under Nathan’s legs, and put his other over the top, locking the naked ankles between them. Then he worked his left arm under Nathan’s waist, found the boy’s left wrist and gripped it. With his right arm useless under Jamie’s back, he was helpless again but Jamie’s right arm was still free.
Nathan could feel the bastard’s leathers all down his right side and across his legs. He could see the bulge in the leather jeans, feel the muscles holding him down. No, not again. No more. There is no way he can make me cum again. I’m empty. And I’ve only got two thousand fucking quid left!
Jamie’s leather-gloved hand came up, and pulled Nathan’s head towards him. He kissed the boy gently, holding him only firmly enough to remind him that he was being restrained. Nathan returned the kiss, his eyes closed. The hand left his head and travelled down his body, stroking, caressing, touching everywhere. He gripped a nipple and squeezed, but when he felt the boy stiffen, he stopped. Not into pain, then. Ok. The hand travelled down to Nathan’s left hip, the fingers feeling around until they came to rest just above the hip bone, and dug in, moving in small circles. Nathan let out a sharp scream of panic, and Jamie felt the boy convulse in his grip: it was fairly clear that being pressure-tickled wasn’t one of his turn-ons. However, he thought, it would underline just how much he was able to control the boy, so he did it again but much more slowly and not so hard this time. Nathan’s body still jerked, his muscles tense - it seemed that he was excruciatingly ticklish - but Jamie kept it at a level that, he thought, would work on the boy’s love of being controlled while helpless. It seemed to be doing that: soon Nathan started to moan in pleasure and to move his body sensuously in Jamie’s restraining grip, whenever the finger threatened.
“You are so fucking easy to control,” he said.
Nathan still had the wrist cuffs on, and Jamie clipped them together behind his back. Then he tightened his grip of the boy’s legs between his own, clamped a leather-gloved hand hard over his mouth, and pulled his head back against his leather jacket. He took Nathan’s cock in his hand and began to stroke it to full erection again. He didn’t hurry, but very soon the cock was solid beneath his fingers.
With the feel of the leather pressing against him, the muscular arms holding him, and the gloved hand gagging him, Nathan was in total heaven.
“The very tip of your cock’s your biggest weakness, isn’t it. You’ve got no defence against that, have you…” Jamie said quietly. “And that wasn’t on the list.” He tutted. “That’s naughty.” He stroked a fingertip over the end of the foreskin lightly. The cock jerked. “When I was making you cum in your jeans it was just on the end. There was fuck-all you could do to control yourself. I was doing it so slowly. Hardly moving. Right on the very tip… That got you, didn’t it…?”
Nathan was moaning.
“Why didn’t you tell me about it?”
Jamie relaxed his hand over the boy’s mouth to hear his reply.
Nathan clearly found this difficult to talk about. “Because… Because I’m embarrassed about it for one thing. It’s an embarrassing weakness. You’re right I just can’t resist it. I can’t resist it however hard I fucking try. If I’d told you about it I’d have stood no fucking chance at all.”
“Oooh yeah,”Jamie purred. “No fucking chance. So guess what I’m gonna do to you…”
“That’s so fucking unfair.”
“Yeah, I know it is.” He chuckled. “But for a thousand quid a pop I’ll use every one of your fucking weaknesses against you. And because you’re so helpless to resist that one, that’s the one I’m gonna use, boy.”
Nathan groaned again and moved his naked legs in Jamie’s grip, loving the feeling of the boy’s leather against his skin, the strong muscles holding him down.
Jamie got up, turned round so he was facing the bottom of the bed, then knelt astride Nathan’s head. Slowly he lowered himself until he was gagging the boy with the bulge in his leather jeans. Leaning forward he took the head of the hard cock between his lips and, just using the tip of his tongue, tickled the end of the foreskin and the piss slit.
The cock responded immediately, stiffening even more. Experimentally Jamie released it from his mouth and pushed it down, pointing it towards Nathan’s feet; in his experience, some boys liked that a lot. When Nathan groaned loudly and thrust his hips once, Jamie smiled - he’d just discovered another weakness.
He got off the bed, hooded the boy again and restrained him on his back, bent double, with his legs strapped together at the knees, his cuffed ankles pulled over his head and fastened to the top of the iron bed frame beyond it. His wrists were roped to the sides of the bed.
Jamie went to the backpack and returned with a pair of long black industrial rubber gloves and a bottle of lube. He reached between Nathan’s legs and pulled his cock and balls through until they were sticking straight out, pointing towards him, the pressure of the boy’s thighs keeping them in place. He carefully wrapped a leather thong around the base of everything several times and tied it off. Then he pulled the rubber gloves on and gently gripped the protruding balls.
Nathan gasped into the hood, then began to moan.
Jamie looked at the cock. It was uncut, and the wrinkled foreskin was covering all of the head except for a quarter-inch circle around the piss slit. The edge of it was darker red. He carefully squeezed it between a single finger and thumb, closing it over the head, then moved it back and forth over the piss slit, pressing lightly. He could feel the two little mounds slipping under it.
Nathan was moving and moaning like crazy now. “Fuuuuuuuuck…. Fuck fuck fuck fuck fuck! ” Even through the hood, that was intelligible.
Jamie chuckled. This was very promising. He lubed the middle finger of his left hand, then very carefully inserted the end of it into the boy’s arse. There had been a small butt plug in the wardrobe, and presumably he had no trouble taking that. More urgent groans came from Nathan, suggesting strongly that all was, in fact, very well indeed. Using his un-lubed right hand he took the foreskin between his finger and thumb again, and moved it around over the very end of Nathan’s cock very slowly and very lightly. At the same time he pushed his finger further in, gently. Every time he moved the foreskin over the tip of the cock, Jamie could feel the boy’s sphincter squeeze his finger sharply. He smiled, knowing that a finger up the arse was usually very good at encouraging boys to want to cum.
Every now and then Jamie would tickle Nathan’s balls the skin even more sensitive now, pulled tight by the leather thong - or work on the rest of his cock, teasing the shaft and the ridge lightly, or sliding the smooth shiny rubber over it. From time to time he pulled it further back against its natural tension, and the resulting gasp from Nathan confirmed that it made the straining cock more sensitive, everything he did to it even more horny. Then he returned to working meticulously on the boy’s biggest weakness: the very tip.
This was clearly driving Nathan nuts. He’d been tied up more often than he could remember, but this was the first time that anybody had known about his great weakness and was intentionally using it against him. That thought itself was turning him on like crazy, but worse was what Jamie was actually doing to his cock it was indescribably, acutely, erotic. Only very occasionally, during his very best wanks in his tightest, thinnest, stretchiest jeans and after a good spliff - had he felt anything approaching that degree of pleasure from his cock. And never during those wanks had he been restrained helpless and hooded, or had a drop-dead gorgeous leather boy working on him. He couldn’t stop himself from moving his head around to feel the hood even more, licking the inside, moaning urgently into the gagging leather, pulling at the restraints, and trying to thrust his hips.
Jamie was concentrating carefully on what he was doing to the end of Nathan’s cock. He grinned as the thought occurred to him that he should have one of those big pull-down magnifiers in front of him. He was looking at a cock that was more of a precision instrument for controlling its owner than any other he’d ever known.
He knew that he could make the boy cum again right now, but he realised that he wanted more - and he found himself trying to think of ways he could make it worse, more humiliating, more insanely frustrating for him. This extreme sensitivity at the tip of a cock was something Jamie had never come across before and it fascinated him because it had such a devastating effect on Nathan and even more because the boy couldn’t control it. He wanted to use it, to exploit it mercilessly.
What he really wanted, he realised, was to make Nathan’s approach to orgasm as slow and as torturous as possible: to do it very, very gradually so that he would feel himself getting closer and closer to cumming bit by bit, have all the time in the world to try to fight against it, to try to control himself, to try to stop himself from getting there but to realise that in spite of everything he could do, he was slowly and surely losing it, and that there was absolutely fuck-all he could do about it. Nothing. He wanted the boy to feel how totally helpless he was in the restraints and the hood, to try to get away from Jamie’s slowly milking fingers and to know that he couldn’t, however hard he tried. He wanted Nathan to realise that the reason he was intentionally working on the very tip of his cock was specifically because Jamie knew that was the one thing the boy was absolutely helpless to fight against.
Jamie had never had thoughts like this before, and it was surprising the hell out of him. But it felt so good, so right . His own cock was as hard as steel in his leather jeans and he badly needed to cum himself, but right now he was far too intent on what he was doing to this boy.
He pushed the cock down again, took the tip of it between his fingers and began working on it again as slowly and as lightly as he possibly could.
He remembered something else on the list: how Nathan loved to be told how helpless he was to control himself. Jamie smiled, then he started to speak very slowly: “Stop yourself from cumming, boy. I’m only using a finger and thumb. But I’m doing it right on the tip of your cock - just like when I made you shoot your spunk into those sexy, skintight jeans right on the very tip, boy, because we both know that’s the one thing you’re helpless to resist.”
The words were coming without his having to think about them, and they were fuelled by a sadism he’d never felt before. “D’you know why there’s a slippery rubber finger up your arse? To make it even more difficult for you to control yourself. More impossible for you to stop yourself from shooting your spunk into my slippery black rubber fingers. Gonna make you cum, boy. Another thousand pounds, Nathan. Another grand you’re gonna lose if you let yourself cum. Can you feel yourself getting closer? Can you feel my fingers working on the very tip of your cock, getting you closer and closer? Right on the tip, and on the very edge of the foreskin, on the piss-slit. You fancy me like fuck, don’t you. I’m your wet-dream leather boy, Nathan, and I’m using your biggest fucking weakness against you - so slowly so that you can feel yourself losing it and know you’re fucking helpless to do anything about it. Is it making you want to cum? Try to get away from my black rubber hands. Try to struggle. Try to fight it. Concentrate. Fight the hood. Fight the restraints. My cock’s as hard as a fucking rock in these skintight black leather jeans, because I’m gonna make you lose control, boy.” Jamie was really getting into this now.
Oh fuck fuck fuck , the things Jamie was saying were going straight to his cock. Inside the hood Nathan was indeed fighting. He was fighting against cumming like he’d never done before. He must NOT cum! He was squirming and trying to kick, trying to get the hood off, doing everything he could to control himself but it was all only making things worse. The finger up his arse was making it impossible to concentrate; the strap holding his knees together and the other restraints felt so horny, as did the leather hood enclosing his head, gagging him and blindfolding him; and his cock felt so fucking vulnerable stuck out between his thighs like that. But worst of all, every slightest movement of that gorgeous hunk’s fingers brought orgasm closer but the bastard was doing it so slowly. So infuriatingly, frustratingly, humiliatingly slowly. Oh fuck, how could anything how could anybody - possibly be this fucking horny?
“A thousand quid, boy. Another thousand quid. Think you can stop yourself from cumming, do you? We’ll see about that…”
Jamie had gripped the boy’s foreskin and was stroking it very slowly around the end of Nathan’s cock. He continued to do exactly that for another sixty seconds, loving the sight of the boy fighting to control himself.
It was time now to get some more cash. But Jamie was surprised to realise that getting the money was, right at that moment, far less important to him than seeing the boy struggling to stop himself from cumming, losing the fight, and shooting his spunk helplessly into Jamie’s slowly stroking fingers.
He chuckled cruelly. “Gonna make you cum, boy!” One slippery fingertip started to massage Nathan’s prostate, and another rubbed quickly back and forth directly over the boy’s piss-slit.
It was calculated to make Nathan lose control quickly, and it did exactly that. His muscles tensed even further, his cock stiffened suddenly and then it began to jerk rhythmically like a thing alive, and although only a small amount of spunk oozed out, Nathan screamed into the hood and thrust his pelvis in another intense, helpless ejaculation.
As Nathan’s orgasm subsided, Jamie moved his finger around the shiny glans on a film of spunk. He thought of something he had a feeling it might work. He made his voice mocking. “Oh look - made you lose it, boy. With one finger. You really are fucking helpless when somebody rubs the end of your cock, aren’t you…” He chuckled quietly. “That’s fucking laughable. You should learn to fucking control yourself, Nathan. It’s pathetic.”
A long, pitiful moan came from the boy. He was in the throes of terminal humiliation.
Jamie gave the cock a final squeeze and got up. When Nathan’s breathing had returned to normal he removed the hood and undid the straps. He wrote a large ‘£4,000’ on the pad, then went into the kitchen and made them both a coffee, leaving the boy lying on the bed. His eyes were closed, and his face was beetroot red.
When Jamie returned, Nathan looked like he was asleep. He put the boy’s coffee on the bedside table and stood looking down at the exhausted figure. He was actually quite cute after all, Jamie decided. And his face had returned to normal colour. He sipped his coffee slowly. This whole thing had opened up completely new areas to him had showed him a side of himself he hadn’t known existed. And fuck, he liked it.
He’d got four thousand of the boy’s five grand. Originally, when he’d found out about the lottery win, he’d intended to take the lot, but he didn’t think there was any chance he’d get the remaining thousand; Nathan was just too exhausted. The fact that the boy had managed to cum four times today already was amazing enough.
He finished his coffee, and put the cup down. He’d won four grand from the boy. But was that fair? After all, he’d got off on this as much as Nathan had. And there was a lot more he’d like to do to him work on him in tighter restraints, so he was unable to move an inch; or in very little so that he could fight and struggle much more; get him in tight leather jeans; make him cum in those shiny shorts over and over until even putting them on would make him desperate for orgasm; find out more of his weaknesses, even give him a few that he didn’t already have, all to be used against him. These were interesting possibilities.
He sat down at the computer, logged in to Nathan’s bank account and looked at the screen.
“Did you mean it?” Asked a tired voice from behind him.
Jamie turned round, looked at Nathan. “What, about you being pathetic?”
He got up and sat on the bed at the boy’s side. After a moment he smiled, then shook his head slowly. “No, I didn’t mean it. Not in the slightest. I said it because I hoped it would make you feel more humiliated, and I think you like that, secretly. I actually think the tip of your cock is… interesting.”
Nathan thought about this, then nodded. “You gonna take the four grand?”
Nathan nodded again. His hair was still matted from the hood. He smiled resignedly. “You won it. You deserve it. Thank you for an amazing night; that was the best experience I have ever had. You are beautiful.”
Could he take four thousand pounds from this boy?
Yes he could. He went back to the computer, transferred the money, logged out, and stood up. “It’s done.”
Nathan nodded again. He watched as the beautiful boy collected his things, putting them into the backpack, his pecs visible under the open leather jacket as he hoisted the bag over his shoulder and moved to the door. “See you,” Jamie said.
“Yeah.” Nathan whispered.
Jamie opened the door, paused for a moment, and then left, closing it quietly behind him without looking back.
Nathan lay on the bed. After a while he gave a long, shuddering sigh.
He looked up as the door opened again. Jamie was standing there, motionless, with his hand on the knob, looking at the floor. Then he seemed to come to a decision. He came back in and closed the door again. “I… I wanted to say. I liked what we did. I got off on doing that to you. A lot. More than I ever thought I would.”
“Yeah. And it taught me something about myself.” He paused, looking down. “I might have a business deal for you, if you’re interested.”
“A business deal?”
“Yeah. If you want…”
“If you want, I’ll pay you for sessions to explore this. I’d like to find more of your weaknesses, learn how to use them against you more effectively. Not like today, but more… leisurely. Take my time.” He looked into the boy’s eyes. “And I want to work on the tip of that cock again, boy.” He smiled. “I want to make you suffer, Nathan.”
Nathan smiled, and then grinned. “How much a session?”
“Oh I don’t know fifty quid a time?”
Nathan appeared to consider this. “Make it a thousand a time to be going on with. I might reduce the price later.”
Now it was Jamie who grinned. “You little bastard. Ok, you got a deal.”
He fell onto the bed and they kissed for ages.