Harrys Punishment Pt 05

Part 5

Joann wheeled her chair to stand between his wide outward open hips. Seeing her there again was the promise of some upcoming torment for his fully exposed privates. Harry's cock was still soft but they all knew it would not stay that way for long now.

Joann grabbed a small paintbrush and began putting her unrestrained access to his upper tights to good use. Harry had never been tickled here and it was not too bad, but she quickly moved to his ass crack. It immediately made him reflexively clench his buttocks, squeezing the brush between them. The oiled buttocks didn't have a lot of hold and she easily slided it out. She then grabbed the paintbrush by its end and swinged it to his balls. Even if the brush was small Harry screamed.

Joann : "That was a mild warning. Relax and allow me full access to your ass crack and hole. I don't want to have to fight again, everytime my brush is denied access, It will land on your balls. I can go much stronger, and unless you've come to love having your balls hit I would advise you to refrain from contracting those ass cheeks."

Harry : "Please, stop, I can't control it!"

Joann : "Poor boy, losing control over your body to a mere paintbrush! But I'm afraid that for your testicular comfort, you will have to try harder!"

Harry could not believe he was forced to fight his own protective reflexes to allow her to torture him. But he knew she would not hesitate to hit his balls with the paintbrush and despite it being small it could be really painful.

He relaxed his muscles and the brush came back on his ass crack. He had to fight his reflexes.

She made some circles with her oiled brush around his hole. Harry was hoping the brush would not go further, but she kept brushing around his anus and his inner buttocks. Having never been touched by somebody else there, his skin was really sensitive and the oil didn't help. Harry's mind was confused by the signals it was receiving. It was at the same time pleasurable but also tickling. He didn't consider his ass crack and hole as ticklish parts, again he was wrong. Again he was yanking on his restraints, laughing and unable to handle the intensity. She was now focusing her efforts on the part between his hole and balls,which was the most sensitive. Her ministrations had the double effect of making him laugh and arouse him. Boys are boys, and his once soft cock was now slowly getting hard, his foreskin was not covering his glans anymore.

Joann : "You seem to love my ministrations, look at this beautiful cock growing!"

She then moved to his scrotum with her brush, the really light contact of the brush with his scrotal skin made him jump. Of course his scrotum had already been touched or even played with during sex, but he had always been able to move to escape any overstimulation, here he wasn't.

Frank decided to re-strap the restraints around his hips and upper thighs to keep him still. He did it quickly, smiling at Harry. Harry could not move his hips anymore, they were held against the cushion and his legs were held by the stirrups.

Frank was enjoying the show, looking at Harry's hardening cock. He seemed to have an idea and left. Harry was too busy to have a look at his destination. He came back bringing back some devices with him. Harry tried to have a look but could not understand the use of the devices, not that it would have changed anything though. He couldn't really focus his mind, as Joann had found that the bottom of his balls was the most sensitive part of his scrotum and was taking full advantage of her discovery.

Frank put a rubber ring in front of Harry's eyes.

"This is called a cock ring, a triple cock ring to be precise. It will make your already respectable cock harder than ever and stay this way for us."

Frank enlarged two of the elastic rubber rings with his fingers and grabbed Harry's cock. Expertly keeping the ring open with 3 fingers he slowly slid Harry's cock through the rings until they reached his scrotum. Joann stopped her ministrations and Frank grabbed Harry's scrotum. He then slid his balls one by one, squeezing them a bit due to the thighness of the ring through the third ring. Harry moaned to express his discomfort.

Harry now had two rings constricting his cock, one at the base, one after his balls, while his balls had their own separating ring keeping them a bit further from his body than usual and exposing his oily scrotum.

Frank admired his work.

Frank : "The rings will keep your cock hard, even harder than usual. I'm quite eager to see it and Joann should take care of that soon. The ring should also prevent your balls from moving up in your scrotum. You see when a man is about to cum, his balls retract before the climax. By preventing them from retracting you can make orgasm more difficult to reach, but more intense."

Joann's brush had resumed its actions against his now captive scrotum. The slick motions were now more teasing than tickling, and it felt good. Too good. Soon Harry was fully hard. As Frank promised, he felt that his engorged cock head was bigger and his cock firmer than usual due to the blood restriction applied by the rings. Harry was ashamed of being controlled so easily. Joann's previous teasing had made him really horny but Frank's testicular massage had taken care of that. But once again his traitorous cock was ready for action, leaving his engorged glans fully exposed.

Then he felt Joann's brush on his shaft, she had decided to move to his cock which was rather good news for Harry. Being aroused like he was, and even considering his predicament, he was feeling a growing need to cum.

Joann : "Look at this beautiful cock, begging for attention!"

He heard the familiar sound of the oil bottle uncapping and felt drops falling on his shaft and glans. Joann then began to spread it on his shaft, sending waves of pleasure to Harry's brain. After several minutes of this teasing torment she moved to his glans and corona, intensifying again his teasing. The contact of the brush on his enlarged glans was like electricity, it was pleasurable, too pleasurable. But as intense as it was, her skilled ministrations were leaving him no hope of cuming, all he could do was to endure the worst teasing he could imagine.

She was playing with his pleasure, delicately brushing his glistening cock head and shaft, and there was nothing he could do to satisfy his growing need to cum. After 20 minutes of this pleasurable but torturous game, his cock was harder than ever and all he could think about was the urge to ejaculate.

Joann then opened the lower drawer of the cart to grab something Harry could not see. She put everything on the cart. There were two square shaped packets, one much bigger than the other and a sort of case.

The fact she was getting objects and her smile scared the helpless Harry.

"Your cock seemed to like being teased. Seeing such a beautiful shiny organ, It would be a shame to only stimulate the outside. I'm sure you've never had your urethra stimulated!"

Harry quickly realized what she meant.

"What, stop it, let me G..." Harry didn't have time to finish his sentence, Frank grabbed his head to put his ball gag back in his mouth."

All they could hear now was muffled words.

Frank took the paintbrush Joann had left to grab her new tools, he grabbed Harry's cock to make it point to the ceiling and began brushing it slowly. Harry tried to trash even if he knew it was useless.

Under Harry's horrified eyes, Joann opened the case and he discovered its content. It contained twelve metal rods, of different diameters and shapes. Some of them were straight rods with bulbous ends, some others had more complicated shapes with multiple bulbous zones. Joann grabbed the big packet and tore it open.

Joann : "This one is for sanitizing."

She applied it to Harry's cock head, still held by Frank and pointing to the sky. She carefully rubbed his cock head, removing the oil and sanitizing at the same time. He felt a light burning due to the chemicals. She pinched Harry's cock head, inspecting his urethra under his terrified eyes. She then selected a straight rod with a bulbous head and opened the small packet.

Joann : "This one is sterile lubricant, don't worry I'll use plenty of it."

She applied a good amount of lube on the rod, and on the tip of his cock while Franck. She then moved to insert the sound in his cock. Harry mentally braced for impact, every single of his muscles tensed. Joann pinched his glans to open his piss slit and he saw and felt the rod making contact and entering his urethra.

The feeling was like nothing he had experienced. The rod invading his most intimate orifice was both sending him strange and pleasurable feelings. Joann was slowly inserting the rod deeper and deeper, taking care not to reach his bladder, but the ring at the base of his cock, constricting his urethra, was a good safety. She was now moving the rod up and down, literally fucking Harry's urethra. Harry was at the same time ashamed, humiliated and lost in a strange kind of exquisite pleasure. No word in the dictionary would have described it. Frank was enjoying the show, Harry's glistening body spasming under overstimulation.

Frank left to gather some things and came back. Harry could not watch anything, his brain being already overloaded. But Joann eventually stopped her game and after a two minutes respite, Frank took the opportunity to show Harry the devices he had grabbed. He really enjoyed taking the time to explain to Harry what he would soon be submitted to. He showed him a metal device.

"Joann is not finished with you and my role now will be to deny the pleasure of cuming under her ministrations. Gladly this melts well with my pleasure to have complete control and painfully play with your cock and balls.

This device is called a ball stretcher, it is made of solid metal and consists of two chromed rings. The rings close around your scrotum, between your cock and your balls. They are connected by those two long shanks. By turning the nuts I can adjust the distance between the rings and by consequence the distance between your cock and balls, allowing me to stretch them as far apart from your body as they can go. I'm sure you've never tried something like that. I won't lie, not being into BDSM I don't think it will be pleasurable for you, but for me, it will provide a nice shiny set of trapped balls to admire."

Harry was horrified by the device, after having his urethra invaded, he was now about to have his balls stretched. He tried to beg, but Frank went on :

"But there's more to enjoy. This model comes with a third attachment, going through the same frame, to be attached on the other side of your balls. Using the wingnuts it is used to slowly crush the wearer's testicles. It's a particularly nasty device I must admit."

This was too much for poor Harry who now imagined his balls being stretched and slowly crushed. He went ballistic in despair.

During the explanation Joann had grabbed another sound. This one was much kinkier than the previous one, with a really elaborate shape. Harry couldn't imagine having this inserted in his urethra, but it was about to happen.

How could it be worse? The answer came from Frank. He was holding a blindfold in front of Harry's eyes. Harry tried to protest but soon the blindfold straps were behind his head, and everything went black.

Frank : "Even if it's nice to see what's going on in your head though your eyes, I want to be sure we have your full attention down there."

There was no way Harry could have distracted from what was to come but the blindfold was another way to render him more helpless again.

Harry heard metallic noises and felt his cock harness being removed. If it had not been for being replaced by a more sadistic device, Harry would have been happy. He now felt Frank manipulating his scrotum and a first ring being secured between his cock and balls, then another one. Frank began turning the screws and Harry felt his scrotum being slowly elongated. At the same time he felt his cock being manipulated, he had no doubt Joann was taking action too.

Frank : "The stretcher should also be more efficient at preventing you from cuming because considering what Joann is about to do there is no doubt you would soon spill your load."

Frank resumed Harry's scrotum slow elongation, and he now felt it really stretched. He could not see them but his balls were being reduced to two shiny orbs, so vulnerable and at his captors' mercy. It was becoming really uncomfortable, and slowly it became light pain. To Frank, there was no doubt this would do a nice job at preventing him from cuming.

Frank : "Don't worry, we promised we wouldn't do any lasting damage, I will not rip your balls off."

Harry was just moaning.

And then he felt the well lubed sadistic sound entering his urethra.

Joann began moving the rod up and down Harry's urethra, under his moans. Harry was breathing heavily, once again the strange pleasurable feeling of having his cock fucked was overwhelming and he would have cum if not for the painful stretching of his balls. But even the stretching would soon not be enough and he was about to reach the orgasm he desperately needed. Frank had noticed it and flicked Harry's trapped balls which sent waves of pain to his abdomen before tuning the nuts to stretch his balls a little further. He screamed in his gag. Soon, Harry felt him manipulating his balls and knew Frank was now attaching the last part of his sadistic device. Frank slowly tightened the wingnuts until the crusher plate made contact with Harry's balls.

Slow ball crushing was one of Frank's favorite activities. Having another man's balls trapped and effortlessly crushed was really exciting particularly when the poor guy could do nothing to avoid it, leaving him full control. The helplessness of the tied up guy was really like no other. He had carefully placed the camera to get a good angle at those shiny balls ready to be flattened.

Joann was now slowly working Harry's shaft up and down, he was lost in this newly found pleasure. He was on the edge to cum when Frank grabbed the crusher nuts and tightened it a bit. Harry felt the light compression on his balls, he panicked, but tied as he was, nothing happened. At the beginning it was uncomfortable, then it became light pain. Frank was doing it slowly, taking his time and Joann adjusted her moves to keep him on the edge. Harry's muscles were tense, particularly his oiled thighs, he would have done anything to close his legs and protect his precious jewels.

For the next 15 minutes, Joann expertly fucked his urethra with the evil sound, frequently adding lube. Harry had never felt such an intense sensation, really pleasurable. But at the same time Frank was taking great pleasure in progressively crushing his balls. Each time he screwed the wingnuts a little bit Harry jumped in his restraints, his pain increasing, becoming agony. Their expert ministrations were at the same time sending to hell and paradise, but also preventing him from cuming. He would have done anything for the testicular pain to stop or be allowed to cum. When they eventually stopped, Joann completely withdrew the sound and Frank unscrewed the wingnuts but did not remove the crusher, he let it barely in contact with Harry's nuts. Harry was nauseous and it took some time for the ache in his balls to begin subsiding. He was completely drained of energy after having tensed and trashed so much against his restraints.

Harry felt relief when he watched Joann pack the rods in their box. His urethra was still very sore and sensitive after the sounding he had endured.

Harry's cock only softened a bit, after the multiple denied orgasms and the continuous edging of his cock he really needed to cum. Joann grabbed a pump bottle from the cart. Harry was able to read the "Swiss navy silicon lube" label on it.

"Time for real lubrication now, Silicon lube is long lasting and really slick, that's exactly what we need now. You wanted me to pleasure your cock, let's start!"

Harry didn't need things to be slick, considering his arousal all he needed was a few good strokes on his cock. It should not last long so the long lasting part was unnecessary but he had no choice.