As far as understatements go, it was a corker. “I cum very easily,” Timmy had told me when we first met. And it has to be said that it caught me out completely. That first session had lasted exactly eight minutes – and that had included the seven minutes and forty-five seconds it had taken to get him stripped and strapped down to the table. I hadn't even got the hood on him – he'd just looked at me approaching him with it and blown his load. I'd thought for a while, gazing at the spunk stain still spreading on his jeans, and then released him.
“Timmy, I'd like another session with you. Now I know about this, I have an idea which you may find interesting...”
He was all for it, which was good – I knew that the next session would be a very different matter indeed...
The first thing I did was to give him a ball of cotton wool. “Strip, wrap this thickly around your cock. Keep it in place with this.” I handed him a rubber band.
He did as I asked, leaving his teeshirt, white running shorts, jeans and trainers on the floor. When he was ready. I sat him down, with his wrists cuffed comfortably behind the chair. A laptop was open in front of him. I put a pair of headphones onto him, and told him to watch the computer. I started it running, sat down slightly behind him, out of his field of vision, and waited for the program to do its work.
I've used hypnosis in sessions for many years, and I've found it very useful sometimes – I can usually make a boy much more susceptible to the things I like to do. I've found that the most effective way is by using videos I make myself in my studio. The visuals of the movie I'd prepared this time were nothing more than a standard vortex – mainly just to give him something to look at – but the audio had been tailor-made for Timmy. There was a music track I'd made up in the studio, basically just a quiet, restful, monotonous rhythm with soft, ambient synth, and over that was my recorded voice, processed to make it sound very close and intimate. It began with a standard relaxation sequence, focussing his attention on each part of his body in turn and getting him to relax it completely; That takes about fifteen minutes, and by the time I'd got to the tongue – which is the very last item on the list - he was fully relaxed and in a reasonable trance already, but I wanted him deeper. The sound track took him through several descents: the cloud, the elevator, and the stairs, by which time he was nicely deep, and I could begin conditioning him.
The first order of business was to sort out this premature ejaculation. I suggested to him that cumming was not the goal he thought it was; that the pleasure he really wanted more than anything was that of wanting and needing to cum; that it was in fact much more long-lasting and horny than the orgasm itself, and that he longed for that pre-orgasm pleasure much, much more deeply than he wanted actually to cum. This was a first for me – I much more often condition victims to want, to need to cum more than anything else, and to do anything they can to achieve that goal – it makes edging much more frustrating, and therefore much more fun. But if I did that with Timmy I knew that he wouldn't even get out of the chair this time before he came. My recorded voice whispered in his ears, telling him in many different ways how much he longed for, how much he needed that feeling of supreme horniness which he could only get before orgasm., and that cumming would end it immediately. I told him how much I wanted to make him feel good, and that I knew exactly how to work on a boy to make him feel more deliciously horny than he'd ever felt before; that cumming would spoil it, would end it, and that is not what he wanted. Then I introduced the idea that he would, in fact, find it progressively more and more difficult to cum. I worked on that notion in different ways, and from different angles, for a long time. Finally I told him that he would find that he could not cum – no matter how much he needed to, and no matter what I did to him. He could not cum. But I also implanted, very strongly indeed, the idea that the more I worked on him and the closer to cumming he got, the more desperately he would want to cum, and the more urgently he would need me to make him cum.
After the conditioning was done. the recording gradually resurfaced him, with the usual suggestions that he would feel wonderful, relaxed, happy, and horny – and that the would want to remember nothing at all of what I'd said to him through the headphones.
The movie faded to black, and I counted him down to full consciousness again. He blinked. I squeezed his shoulder and said, quietly, “Timmy? How do you feel?”
He turned to look at me and smiled. “I feel good!”
“Excellent! Ok – come over to the restraint table and I'll get you strapped down.”
I carefully unwrapped the cotton wool. His cock was as hard as a rod, but so far he hadn't cum. I set about fastening the leather straps over his arms, wrists, body and legs. Then I picked up the leather hood. “You Ok?” I asked.
“Oh yeah!”
I pulled the hood over his head and buckled it up. His cock jerked, but no orgasm. So far so good. Then I sat down by his side and took a very soft, pointed feather. With some trepidation I touched it to the shaft of his cock, which jerked at the touch. I ran it slowly up, stopping short of the sensitive head. He moaned in pleasure and writhed lasciviously in his restraints. This was much more like it, I thought.
I used nothing more than that single feather for the next twenty minutes or so, getting more confident with each stroke, but keeping a very close eye and ear on his reactions. He moaned and purred wonderfully. It seemed that the conditioning was working brilliantly.
Judging that I could get away with it, I put the feather down and used my fingers now. Very cautiously at first, I teased and tickled his inner thighs, his balls, and his cock – still avoiding the head. Then, over many minutes, I gradually increased the intensity of what I was doing until my fingers were all over his erogenous zones. He was struggling and sighing with pleasure – and now he started trying to get his hands to his cock. “Oh fuuuuckk.... I want to cum. Make me cum, please.”
Time to increase his frustration. I knew he had a major fetish for leather (which was why he'd cum so easily on seeing this masked, leather-clad biker approaching him with a leather hood that first time) and so I pulled my skintight, shiny leather cop-gloves on. I lightly gripped the shaft of his cock. “How do those shiny black leather gloves feel on your cock?” I whispered.
His reactions told me as much as his reply: he struggled in his restraints and fought to get his hand to his cock to finish himself off. “FUUUUCK! YYYEAAHHHH!! OH SHIIIT! I GOTTA CUMMMM!”
For a moment I thought he'd said “I'm gonna cum”, but then I smiled as I realised what he'd actually said. I continued to work on his cock with my leather fingertips for a while, then I reached down and picked up the pair of leather jeans that I'd placed there. I held them above him, the legs hanging down, and slowly lowered them onto him, so that the legs made contact all the way down his inner thighs, and his cock went between the tops of them. As the cool leather made contact with his skin he let out a series of gasps of pure lust. I laid the upper part of the jeans on his stomach and pelvis, so that his naked cock was poking out, completely surrounded by the leather jeans, then ran my hand up his thighs, pressing the cold black leather against his bare skin, and sliding them up to make contact with the sides of his balls.
Placing my hand on his lower abdomen, with the root of his cock between my thumb and my fingers, I move the hand towards his feet until his cock pointed as far down as it would comfortably go – the most supremely sensitive position on most boys – and gently curled my leather-gloved gingers around his balls. Then, with a single finger and thumb of my other hand, I lightly gripped his cock-head and began to stroke it very, very slowly.
He went ballistic: he fought the restraints, yelled into the hood, and thrust his hips so violently that if I had kept my fingers still on his cock rather than follow his movements, he would have fucked my hand to orgasm in seconds. But I moved with him, intentionally making it impossible for him to cum that way.
“You want this to carry on forever, don't you, Timmy...?”
His hooded head nodded hard and fast.
“Do you want to cum?”
He shook his head violently from side to side. “YES! YES! YES!!!”
I chuckled. I'd seen this kind of mixed reaction so many times. Well, I thought that was probably enough for this session. I'd make him cum now, and we could explore further – with conditioning – next time.
I turned the leather jeans over so that the cool surface was against his bare skin (which brought fresh gasps of lust from the boy), then quickly pushed one gloved hand up between his thighs to grip his balls at either side, and wrapped my other hand around his cock, getting a good film of precum between the leather and his cock-head. With firm, irresistible strokes, I milked his cock, rubbing my thumb over the head each time. This has never been known to fail to make a horny boy cum in seconds.
Except Timmy didn't cum. I worked on his cock for about a minute before I realised that he was not, in fact, going to cum. He was screaming with the need for orgasm, his head desperately moving from side to side and his muscles tense with need.
Luckily, I think fast in such situations. I was pretty sure that what had happened was that the conditioning had taken far more deeply than I'd thought it would, and that for now, at least, nothing at all would make it possible for him to cum. Oh, if I did nothing, he'd return to normal in a few hours, but I'd thought of a fascinating way to use this, which would indulge another of my major turn-ons. His white running shorts had given me the idea.
Saying nothing, I unbuckled the restraint over his right hand, so that he could now reach his cock. “Try to make yourself cum, boy.” I laughed quietly.
His hand flew to his cock and he started wanking himself off furiously. But after a couple of minutes it was clear that I'd thought correctly. He could not cum. He was moaning with frustration.
I grabbed his hand and re-fastened the restraint. “See? There is no way you can cum, Timmy,” I said, as if this was exactly what I'd intended to happen. “I've made very sure of that.”
I went over to the pile of clothes, took his white shorts and unfastened his leg restraints. I got his shorts onto him, pulled them up, then refastened his ankle restraints. I scanned folders on the laptop until I'd found the file I wanted, then placed the machine by his side on the table and put the headphones over his hooded head. “Do you want to cum?”
“Oh fuck YES!”
“Ok. Now just relax, Timmy. Relax, and listen to my voice...”
I double-checked that the right file was selected, and started the movie. I heard the sibilants of my own voice from the headphones. I smiled to myself. The induction went smoothly and quickly, and my voice began shaping his needs again.
When it was done, I asked him how he felt. “I feel fine, thank you,” he said. I could detect a slight frown in his voice that hadn't been there before. That was perfect.
Very carefully, I changed his restraint position to a hogtie, with him lying on his side. I touched the bulge of his cock through the thin, shiny nylon. It jerked urgently under my fingers.
“No.” His voice was uncertain, but quickly gained strength. “No, get off my cock.”
“But you can't stop me getting to your cock, can you...?. And I am going to make you cum in your shorts.”
Somehow, although his face was beneath a layer of black leather, I could tell he was blushing. “No. Fuck off.” He jerked himself over so that he was facing away from me. His fingers were trying to get to the buckles of the wrist restraints, but I knew they were out of his reach.
“Now listen very closely. I am going to make you cum helplessly in your shorts, and there is fuck all you can do to stop me.”
He buried his hooded face in the padded table. “You will NOT, you fucker!”
I pushed one hand between his thighs, and worked it quickly up inside the leg of his shorts to grip his balls, and simultaneously closed the finger and thumb of my other hand over his cock head through his shorts. “Fight it all you like, boy – you're gonna CUM”.
He fought. He struggled, tried to get the hood off, tried to kick with his legs, tried to dislodge my hands, but I knew that every movement he made was reminding him exactly how helpless he was, how I'd got him so he couldn't get away, couldn't see to fight, and how absolutely I controlled whether he would cum or not. My hand, clamped tightly between his vice-like thighs, was invading that most protected area – up the leg of his shorts - and massaging his balls; while the fingers of the other hand started to work on his most supremely sensitive spot – his cock head – through the thin while nylon. There was no way he could get away from my hands, nowhere he could move to escape the milking. In seconds his body tensed, he shook his head and screamed obscenities into the hood, and his hips thrust wildly. My fingers started to slip and slide as the spunk pumped out of his insanely horny cock. He came. And it went on and on. I continued to milk his madly jerking cock until he collapsed exhausted, his balls finally dry.
I removed the hood and looked at him. He lay there gasping, eyes tightly shut, face as red as a beetroot. When he opened his eyes, he immediately avoided my gaze. “You bastard,” he croaked.
I grinned, and gave his shoulder a squeeze. “Did you enjoy that?”
It was a moment before he responded, then he turned his head to look at me, and he smiled too. “That was the best orgasm I have ever had in my life. Thank you.”
I never, ever tire of hearing a boy say that to me. It is the best compliment I can possibly have.
I released him, and sent him home. Will he come back for more sessions? Oh yes, you can be sure of that. That second conditioning file had quite a lot on it – apart from making him see my forcing him to cum in his shorts as the ultimate humiliation, and to be avoided at all costs, but that he wouldn't be able to stop himself from cumming whatever he did to try to prevent it, apart from that, it also contained a very carefully-worded and heavily implanted suggestion that from now on, I was the only person in the world who could give him really satisfying orgasms. After a few days of very indifferent wanking, I knew without any doubt at all that he would be back for more.
That's the wonderful thing about hypnosis – it works.