The Telemachus Story Archive

A Toss of the Coin
By Hooder

A Toss of the Coin

How I got Pip into my playroom is not the important thing; the important thing is why. He’s an arrogant little prick - he’s pretty and he knows it – and he has pretensions to being a top. He’s only recently started doing it and he knows fuck-all about it, but unfortunately his looks – along with the cash to buy leather gear which fits him like a second skin - attract a lot of subs who should know better.

Last week Dale’s boy Jamie had a session with him; it was all about edging, and that should have been fine, but it wasn’t. Master Pip got Jamie tied up and proceeded to try to edge him. It wasn’t working (Jamie told me later that Pip had ‘no fucking idea how to handle a cock’) and so he tried everything he could think of to get Jamie hard – with no thought to whether his victim wanted it or not. Breath control (Jamie almost lost consciousness at one point); electrics (only stopped after the screaming got too loud); inexpert nipple work (more screaming); and prostate massage (the finger searching in completely the wrong direction).

Eventually Jamie had forced himself to get hard, and had even managed to make himself cum (just so that the fucking session would end) – but Pip hadn’t noticed that Jamie’s orgasm had started and had taken his hand away at just the wrong moment. Jamie had yelled into the gag to get Pip to keep working on his cock but the guy’s attention was elsewhere by then. It had all been a dismal failure. Pip had thrown Jamie out, saying that he was the worst sub he’d ever had, and that he should come back when he’d learned how to do it.

I’ve had many sessions with Jamie in the past - he’s actually a satisfying and responsive sub – and so I thought I’d teach young Master Pip what edging is all about, and a lesson which, I hoped, he wouldn’t forget.

So there he was, strapped into my gynaecological chair. I was proud of that chair – I’d got it for a snip a few months ago from Ebay. It’s great for doing all sorts of things to boys as their legs are held raised and apart so that access is excellent from all angles, and there are many places that straps can be attached. I’d had to gag him through the mouth hole of the hood as well because he’d been cursing fit to bust ever since my mates had brought him in. Pip and I didn’t know each other at all – I’d seen him once at the far end of the club but he’s not my type and we’d never spoken. On my instructions, the guys had made very sure he couldn’t see while he was being abducted, so he had no idea where he was.

I stood by his hooded head. “Now, Master Pip. We’re going to have a little tutorial. It’s about edging. And the first thing we have to do is get you hard.”

This brought renewed swearing, struggling and shaking of the head.

“When you’re going to edge someone you don’t necessarily know what your victim’s cock responds to, but before you can start, you have to find out. It’s usually best to begin with very slow, gentle work on the shaft, and to tickle the balls. Like this…” I took his soft cock between my rubber-gloved fingers and began to stroke it, and to tease a soft feather over his balls. The struggling increased even more, and the swearing was now interspersed with sharp, short shrieks.

“Ah, I see you’re ticklish too. This tutorial isn’t about tickling, but I’ve made a note of that for possible later use. You never know when something like that might be useful.” My fingers continued to slide up and down the shaft of his cock, and soon I felt the first stirrings of erection. I smiled. “There’s a good boy,” I said slowly, “you’re beginning to get hard.”

Pip’s head was shaking violently from side to side now, and I knew he was doing everything he could to keep his cock soft. But he couldn’t. One thing in my favour was that most eighteen-year olds have precious little control over their cocks; that sort of thing tends to come with age and experience.

He was now almost fully erect. “You see? It’s easy to get a cock hard. No breath control, no electrics – just gentle stroking, nothing else, and there’s fuck-all you can do to stop it. So, let’s look at that cock head, shall we?” I picked up a second feather and stroked it as lightly as I possibly could over the shiny glans. With edging, less is almost always more: the less you actually touch a cock, and the more lightly when you do, the more desperate for serious attention it becomes.

He gasped as the feather stroked, and began to moan quietly. I smiled: this boy was almost too easy to control. Using both feathers now I tickled his balls and his cock head very lightly. Feather teasing doesn’t work on everybody, but I’ve found that it’s always a good way to begin as the ones it doesn’t work on are few and far between.

Pip’s cock was straining now, trying to fuck the feather, so I knew that already he wanted to cum, and I’d only been working on him for a few minutes. I was enjoying this. Pip wasn’t at all the kid of guy I preferred, but making the bastard suffer was intoxicating. “I think you’re getting horny, Master Pip.”

He was making an odd mixture of noises: there were groans of infuriation, but also moans of lust and a strange vocal creaking that I recognised as a reluctant expression of need. I carried on working on his cock, but now I directed the soft point of the feather more often onto his frenulum. As I’d expected, this caused all of those noises to become louder and more urgent.

“Do you want to cum yet?”

He nodded quickly.

I took a 10p piece out of my pocket and dropped it onto his bare chest. “That’s a coin. I’ll toss it. If it’s heads I’ll let you cum. If it’s tails, we’ll continue. Ok?”

He was shaking his head now. I picked up the coin and tossed it, making sure he could hear it slap onto the back of my other rubber-gloved hand. It was heads. “Aww, it’s tails,” I lied. I picked up the feathers and went back to work on him.

By the time half an hour had passed his moaning had become very loud and very urgent, and every couple of minutes I had to wipe the precum off his cock with the corner of a piece of tissue (this also caused much struggling).

I tossed the coin again – and this time it actually did show tails. “Tails again I’m afraid. But I don’t want you to get bored, so let’s do something different. Let’s see if we can find your prostate, shall we?” I gave him a moment to struggle and do more head-shaking. “Before we go inside, let’s have a look here…” I put a couple of fingers on his perineum and felt around. His moaning told me I’d found it. I massaged it gently for while.

“Good. Ok, now let’s explore it a bit more deeply.” I lubed the middle finger of my right hand well, then worked it past a sphincter that he was doing his damnedest to keep closed, and slowly pushed it in. “Now, the thing to remember is that the prostate is a couple of inches inside, and in the direction of the navel. It’s not difficult to find if you know where to look.” My fingertip touched the hard little gland. “There. I can feel it. Can you feel it?”

The surprised gurgle that came from him made it quite clear that he could indeed feel it. I began to massage it carefully. The gurgle turned into short gasps of pleasure and, moments later, of need.

“I could easily make you cum like this, but I won’t.” I continued to rub it very gently for a while.

“The effect is even better if your cock’s being teased at the same time…” The feather resumed its wickedly tickling work on the head.

I’d made sure that the strap over his pelvis was especially tight so that he couldn’t hump much at all, but that strap creaked alarmingly as his hips tried to thrust. This was really beginning to get to the boy.

I’ve found that prostates usually respond best if you work on them repeatedly, but not for very long at any one time, so I removed my finger and returned to tickling his balls with that hand. Later, I went back inside again.

“Nope, tails again. I wonder if this coin is properly balanced. Let’s try another one. I wouldn’t want you to think I was cheating.” I swapped it for a 50p piece and tossed it again. I didn’t even glance at it to see which face came up. “Doesn’t look like it’s your day, Master Pip. Tails again. Oh well…”

After a further half hour Pip was beside himself. He needed to cum so badly it was the only thing he could think about. I inserted a rigid stimulator so that I had both hands to use. Every little movement now would make it slide over his prostate and work on him without assistance from me. I lubed my rubber-gloved hand very well and enclosed his cock with it. Holding it still, I stroked my thumb over the glans gently. My other hand was free now so I very slowly teased a fingertip in his right armpit, just to see what his reaction would be. On some guys, when they’re horny, spots that are usually very ticklish become extremely erogenous. This seemed to be the case with Pip – both armpits did indeed seem to be responsive, and his moaning increased even more. Another fifteen or twenty minutes was spent doing this.

His cock was producing so much precum that the lube I’d put on my hand was really superfluous; when I began to slide it very slowly up and down the full length of his cock, the movement was smooth and silky in the mixture of lube and precum. I paid particular attention to the ridge and the head, making sure that the gently twisting motion of my hand stroked them as well.

He got to the point of cumming almost immediately, and I stopped. Like many teenagers he was very easy to edge – he was concentrating so much on his approaching orgasm that he was oblivious to the facts that his muscles had tensed and that he was holding his breath. These two things together provided me with good signals as to how close he was.

He wailed when I let go of his cock, and shook his head in desperation. The gag muffled his words completely, but I knew he was begging me to let him cum. I waited for a while to let him back off from the edge, then started on him again.

After several repeats of this – during which he got even more increasingly desperate - I stopped, and retrieved the coin from where I’d put it on the side of the chair. “Ok. Let’s go for tails this time, shall we? These coins seem to like tails today. Tails you cum, heads you don’t.” I flipped the 50p piece. “Well would you look at that – heads at last.” I hadn’t even looked at the coin. I went back to work on him.

“You see, all it takes is just slow, gentle work on a hard, horny cock, and a bit of concentration to monitor your victim, so you know how close he is to cumming. See, I can get you to the edge so easily - like this…” I held the shaft of his cock still with my hand, and moved just my thumb slowly over the glans. His body tensed and he held his breath.

“And then I stop, so that you can’t cum.” Carefully I took my hand off his cock.

He was almost sobbing. Master Pip really needed orgasm. This time, to make it worse still, I encircled the root of his balls with a finger and thumb, and pulled them gently away from his body, keeping a tension on them while I began once again to work on his cock head infuriatingly slowly.

“Now, I want you to imagine that my hand is rubbing up and down your cock and over the head very firmly.” My voice was soft, the words slow. “I love using smooth black rubber gloves; slippery rubber makes cocks want to cum. Imagine that rubber sliding over it. The stimulator in your arse is stroking against your prostate. You can feel your spunk moving up inside your cock… and then shooting out into my slippery, shiny rubber-gloved, milking hand. Visualise that. Imagine what it would feel like being milked like that. Imagine the intensity of it. You’re so horny now that it would feel fucking amazing . It would be the best orgasm you’ve ever had in your life.” I let go of his cock again. I could almost see steam coming from it.

He beat his fists onto the arms of the chair making the restraints rattle, and his whole body jerked in impotent fury.

“But you can’t cum, can you… You can’t stop me from making you need to cum more and more, but however much you need to, you just can’t cum unless I let you. You’re strapped down and hooded. You don’t even know who I am or where you are… There is fuck-all you can do. You’re helpless. Now that is how edging is done.”

I looked down at him. I could make him cum now, and give him intense pleasure – or…

“Now, there’s one more thing. I know you want to cum more than anything - but as well as being a tutorial, this is also a lesson, Master Pip. If you’re going to be a top, you have to know what something feels like yourself before you inflict it on someone else. And you have to know how bad you can make a sub feel if you’re not careful. It’s all part of being a responsible top. So I’m going to toss the coin again. Heads I’ll milk your cock properly, tails I’ll give you a ruined orgasm. You ever heard of those?”

Pitiful moans were coming from under the leather hood.

“We’ll let the fates decide.” I tossed the coin. “Tails, I’m afraid,” I sighed. It actually had been, this time.

“Well, think of it as punishment. There is at least one sub who you made very unhappy indeed last week.”

Pip reached the edge again almost immediately when I resumed working on his cock. I gazed at it – it was rock-hard, the smooth glans purple and angry, shiny with precum, and I knew that nothing more than a single firm stroke would make him shoot uncontrollably. Normally I would grip it with my rubber-gloved fingers and rub the whole cock – including the head – firmly and more quickly; this would make any horny teenage boy cum instantly and volcanically. But I didn’t do that.

Instead I used a single fingertip just on the very tip of the head, stroking it directly across the piss-slit, and only barely making contact at all. I knew this would take longer to make him cum, and so it would give me more control. He would feel the pressure building up relentlessly until that point was reached where the dam gates burst open and full, wonderful orgasm began. And he’d also realise that doing it like that was going to make it even more shatteringly intense.

Even with just a single fingertip working on him very slowly indeed, it was only a few seconds before his body suddenly stiffened, and he yelled into the hood. Yes! He was going to cum!

Gently, I lifted my finger off. He screamed – I could almost hear the words through the gag: ‘NO! DON’T STOP! WANK ME! FOR GOD’S SAKE RUB MY COCK!’

But I just stood, smiling, and watched as it jerked once powerfully, and then again much less so, and a single, small, milky-white drop of spunk appeared at the tip. This was slowly pushed aside by one more, even smaller. They joined together and ran sluggishly down over the head. The jerking had stopped altogether now. After five seconds or so it was all over. He wailed and swore into the gag. Not only had he felt zero pleasure from that, but also the fact that he knew it would have been such an intense orgasm made it so very much worse.

“You see, Master Pip? That is a ruined orgasm.”

He was still swearing at me.

I knew that the boy was still as horny as fuck – ruined orgasms usually do little to reduce the need for very long – and that very soon indeed he’d be desperate to cum again. So I picked up the 50p piece. “Now, let’s toss this coin again. Heads I milk your cock hard and fast, tails we explore ruined orgasms a bit more. Ok with you?”

His body was trembling, his head was shaking in panic. He was broken. “Mmmmph…”

I smiled, and tossed the coin.