Progression Ch. 03: The Show

"Hi boys" said Ryan finally finished with his customer. "You came to see me?"

"Yeah we wanted to get Nathan some different underwear. He's been wearing those leather pants for days" explained Jack. "Oh also we needed to get a nice dildo for him, we discovered he wants to explore his anal side."

Nathan turned bright red and whispered "I didn't... no... well... Oh, I don't know, maybe, but people can hear. Shush."

"No one cares in here" reassured Ryan "You've got to get over your fears."

They went up to the counter and Nathan purchased the items. Ryan brought down a cock shaped dildo from the shelf above the counter. "This should do fine" as said as he swiped it through the till.

Nathan paid for everything, and Ryan's staff discount made things a good price. After he bagged everything Ryan let the last customers out of the store before locking up and leaving for the afternoon. Finally he could go home and play.

They went back to the house, with Jack eagerly explaining everything they did earlier on. Ryan liked what he heard and Nathan just stayed in a constant state of frustration thinking about every possible scenario that could happen to him.

"Okay we have half an hour until the show" said Jack. "I'll go setup and you two can make sure Nathan's new underwear fits."

"Wait, what show?" asked Nathan. But Jack had already left for the basement.

"It's nothing really, we just do an online show every Saturday. We've done it for years. You don't have to join in, you can just watch if you'd like" explained Ryan.

Nathan shrugged and looks a little confused.

"So which one to try on first" asked Ryan. They tried on the y-fronts, thong and leather shorts. Ryan found the lock amusing on the shorts, as it gave double protection.

"Next let's try the jockstrap?" instructed Ryan.

Nathan reached for the jockstrap and opened it from the packet. It was a pure white strap with a pouch for the penis, or cage, to rest. Inside was a plastic protection cup.

Nathan removed his shorts and underwear.

"Good, Jack put you back in the cage" said Ryan pleased Nathan was not free. "Did it feel good to get out for a bit?"

"Yeah, I just need to cum so badly though. It feels like I haven't cum for weeks, even though it's just been a few days" said Nathan.

Ryan picked up the cup and held it against Nathan's chastity cage. Nathan slipped his feet through the holes in the jockstrap and pulled them up and over his waist, holding the cup in place. He sighed in relief.

"The cup actually holds the cage in place so it doesn't hurt as much" said Nathan happy to get some relief from the tugging against his balls.

"Perfect, should we go see what Jacks up to" asked Ryan as he gently pulled Nathan's arm towards the basement.

Nathan could feel his cock attempt to fill with blood. He had been waiting for this all day and could only hope he would finally get to cum.

Then walked down into the basement and saw Jack had setup the camera pointing to the bed.

"Tell you what Nathan, you can take that laptop and read out any comments to us" said Jack, knowing Nathan was too shy to join them.

"Sure, okay" agreed Nathan as he watched Jack remove his shirt. Jack was a slim and lanky guy, and very attractive. He was a bit of a geek but looked after and groomed himself well. Jack continued to remove his shoes and pants leaving on only his y-fronts and socks. Nathan's cock was pushing up against his cage. It was the first time he had seen Jack almost naked, and the outline of his cock in the y-fronts turned him on greatly.

He jumped onto the bed and Nathan could see the camera on the computer update in real time. Next Ryan removed his t-shirt and pants, then his socks and underwear leaving himself completely naked. He covered his privates, preventing Nathan from seeing anything. He then jumped onto the bed with Jack and pulled a small towel over his privates.

They rubbed each others chest and Ryan licked on Jack's nipples teasing him and the small fanbase who had signed in early as always.

Over the next hour the online room filled up with a few hundred viewers. Nathan helped by reading out the comments and answering questions from the audience.

Finally some tips started coming in asking for requests. The first one asked for the guys to show their ass on the camera. Nathans heart beat faster at the thought.

Ryan went first. He held onto his privates with his hand, while bending over in front of the camera. His cock still couldn't be seen, but his smooth ass was on show for the world to see. Next Jack went beside him. He left his underwear on but slowly pulled down the back, revealing his firm, toned and shaved ass.

On the camera the audience could see the two guys shaking their ass for everyone to see. Nathan couldn't believe he was getting to see the show live. Normally when he watched porn online he would hold onto his dick and make himself cum within a few minutes. But with his cock trapped in its prison, all he could do was watch and enjoy the frustration.

The next requests came in, some with Ryan slapping Jack's ass then some light bondage play with clothespins on their nipples. Jack then had to dry hump Ryan while still in his underwear.

It had been almost two hours and Nathan had still not seen either of the guys cocks. It was the only thing on his mind at this stage, and how badly he wanted to make his own cock cum.

"Can I make a request" asked Nathan. "Can you suck on Ryan's cock?"

A few messages came through on the chat room.

"Who's there with you?" said one comment.

"Do you have a friend. Bring him in" said another.

Nathan read out the comments then Jack said "He's too shy for you guys. He won't come on the camera. But if he changes his mind and comes online with us, we will show you our dicks."

Nathan, so horny his inhibitions left him, jumped onto the bed to join the guys. There he was exposed for the three hundred visitors online to see him wearing nothing but his jock strap.

More messages came through about how things were getting hot, and the room attracted a few hundred more visitors.

"Well a promise is a promise" said Jack while removing his underwear.

Jack reveal his uncut cock which, although not erect, must have been six inches already. Ryan too removed his hands and reveal his uncut cock, slightly bigger than Jack but he was slightly erect.

They both played with their own cocks for a while, making themselves harder.

"What about the new guy. Let's see his." commented a visitor.

"Yeah, you said everyone would show theirs" commented another.

Nathan went bright red and declined.

"He will help us get ready instead" said Jack while pulling Nathan's hand over to his cock.

"Just stroke it up and down, slowly then faster" said Jack.

Nathan had never touched another man's cock before. He had only watched online, the exact same shows that he was now performing in.

Ryan then slowly brought Nathan's head down to his cock. "Now open your mouth and suck gently" he instructed.

Nathan's balls felt like they would burst cum all over the bed if only he could just get a bit of friction. He let go of Jack's dick to try and stroke his cock cage, but with the jockstrap cup in the way he couldn't even feel the cage.

Jack reached out and pulled Nathan's hand back onto his cock. Both Ryan and Jack started to moan while Nathan serviced both of them.

Finally Ryan got onto his knees and pushed Nathan's hands away. He took over and started to suck Jack's cock, while Nathan continued to suck Ryans.

The audience loved it, and more visitors came to view their page.

Jack lay back enjoying his cock being sucked and stroked by Ryan. After a few minutes Ryan got on top of Jack and slowly put his cock into his ass. Slowly he started to thrust up and down. Nathan was now sat on the side, watching as Ryan's cock pushed and pulled into Jack's ass.

They sped up, getting faster and faster. Jack pulling on his own cock while Ryan thrusted into him, the camera catching everything for the entertainment of the visitors.

Nathan went in to suck Jack's cock. Jack allowed him and moaned at the pleasure of getting sucked by Nathan and penetrated by Ryan. After another fifteen minutes Jack started to thrust into Nathan's mouth pretty hard. He was getting faster and faster. Nathan knew he was about to cum, which only reminded him of his own need to release his load.

A few more sharp thrusts and a final gasp from Jack, and a fast projectile of cum hit the back to Nathan's throat. He gagged and spat out the load onto Jack's chest.

Jack got up and left the bed to get some tissues, leaving Ryan still erect and ready to cum.

"Well, looks like you finished Jack off. Who's going to finish me?" joked Ryan as the audience all replied with different forms of "finish him, finish him."

Ryan picked up a packet of lube and lubed up his cock. "Now, nice a slow. Make me cum." he said.

Nathan started stroking Ryan's cock, while Jack came over and wiped up the cum Nathan spat out.

It didn't take Ryan long to cum, and after a couple of minutes shot his load all over Nathan's hand. All Nathan was thinking about at this point was about his own cum and wishing he could rub his cock and ejaculate over Ryan's torso.

With the two guys orgasmed and finished for the night, the chat room started to clear and finally Jack turned off the camera.

"Really glad you joined in. See it wasn't that bad." said Jack.

"Jack, please can you and Ryan make me cum. That was the hottest thing ever." begged Nathan desperate to cum.

"Well it's getting late. We're ready for bed to be honest. Can you wait another night?" said Ryan.

"No please, it's too much. My balls are aching and I'm so horny." Nathan begged again.

"It's Sunday tomorrow and we have to see some other friends, but if you come back on Monday evening we can talk about it some more" said Ryan.

"I can't, I need out of the cage. I'm sorry guys, can I have the key" Nathan asked.

Jack and Ryan looked at each other in disappointment.

"Of course you can Nathan. But I thought this is what you wanted. We don't want someone to jerk off and make cum, we want someone to tease and edge. If you want out we will give you the key but then there is no coming back. If you leave now you'll have to find someone else when you're ready to be locked again." explained Ryan.

Nathan didn't care. He asked again for the key. Jack went into his pocket and handed it to him.

"Thank you, I'm sorry guys" said Nathan so excited to have his key back.

"No problem, it was fun. We wish it could have done on longer." said Jack.

Ryan handed Nathan the bag full of his new underwear and headed out the door saying their final goodbye. As Nathan walked away he remembered wanting for years for his cock to be locked up and teased. He had everything he wanted and was with two extremely hot guys.

"Screw it" he said turning back towards the house. "I'm sorry please take the key back." he asked.

"So first you begged us to give you the key, now you are begging us to take it back" laughed Ryan while taking back the key.

"Can I see you guys again" asked Nathan.

"See you Monday" replied Ryan closing the door.

Nathan walked home, hopelessly thinking about how close he was to cumming, and how he had enjoyed his own close up and personal webcam show.

By the time he got home he went up the stairs and straight into the bathroom to clean up. He turned the shower on and put it on cold, trying to relieve himself but it was no use. His horniest would not go away at all.

He looked over at his shopping bag with the underwear and noticed the dildo Ryan had put in there for him to try. Eager to try anything to relieve himself he reached over and opened the packet.

He pulled out the dildo. It was about eight inches long but quite slim.

"Okay this has to do it" he thought to himself. He bent over in the shower and played around the entrance to his ass. He had never inserted anything up there before.

He could feel the chastity cage hanging from his balls as he bent over to try and insert the dildo. He tried a couple of times, but ended up hurting himself every time. He couldn't fit it into his ass hole. No matter what he tried, it just wasn't going to fit.

Nathan couldn't stand it anymore. He started hitting at the cage, trying to break it open. But the cage stayed exactly where it was.

He poked his fingers in, tried to pull his balls through, but again nothing would remove the cage, until finally he noticed a bottle of mineral oil on the shelve.

"Maybe I could grease it up enough to slide out" he thought to himself.

He poured the bottle over his cock and balls and rubbed in as much as he could. He poured a bit into the opening where his cock head was, trying to grease up as much as possible.

Each tug and pull made him more horny. Finally he was able to stick his finger between the cage and his dick. With a few more drops of oil he finally managed to slip his cock out of the tube.

Finally with his cock free, it took only a bit more work to remove his balls from the ring too, leaving his cock erect and ready for action.

He poured on some more oil and started pulling his cock. Stroking up and down on his penis it took him thirty seconds before he shot his load all over the shower door. His cum kept on shooting for the longest time since he first discovered the orgasm. He sighed in a huge relief. Never had he needed to cum so bad in his whole life. He sat for a moment and looked at the cage as his cock slowly relaxed and became flaccid again.

After finishing his shower and cleaning his cum off the shower door, he dried himself and took his stuff back into his room.

Exhausted, he put the cage in his drawer and put on some normal underwear. Once in bed he was asleep within minutes, not to wake again until ten the next morning.