Progression Ch. 05: Overnight

Nathan got showered, making sure to use his syringe only two times. He dried himself off and got changed into his leather locking pants. He put on some tracksuit pants and a t-shirt, before heading out the door almost running to Ryan and Jacks.

Finally, he was standing outside their house knocking on the door.

"Well aren't you eager?" said Ryan. Maybe it was the frustration or the long time away but just looking at Ryan and hearing his voice made him lustful and hornier than ever. Ryan was wearing a tight white shirt with a blue tie and a black pair of trousers. He looked smart, professional and handsome.

Nathan followed Ryan inside and through to the garden where Jack was lying on a lounger wearing only a pair of blue shorts, and sunglasses.

Jack stood up and faced Nathan. "What a week, right?" he said.

"It's been impossible. Please can you let me out of the cage?" begged Nathan.

Jack ignored him and reached over to Ryan to kiss him. "Come with us," he said.

Nathan followed the guys into the basement. As soon as he reached the bottom of the stairs, his cock began to swell in his cage as he remembered what happened the last time he was there.

In the middle of the room was the webcam setup and looking directly towards the chair he was tied too for the first time.

"Go on, have a seat," said Ryan.

Nathan walked towards the chair, but Ryan held out his hand to stop him. "Not you, Jack's going to have a go in the chair," he said as Jack sat down, placing his feet and hands into the metal brackets securing him to the chair.

"Since you've been good this whole week, we have a treat for you," said Ryan as he knelt down and locked the brackets to the chair. He then stood up and kissed Jack.

Nathan could see Jack getting hard through his shorts.

"Nathan, let's get these shorts off him" directed Ryan.

Nathan walked over to Jack and pulled down his shorts down to the chains that bound his legs.

Ryan came over with a pair of scissors and cut the shorts off his legs. He then picked up a tube of lube and poured some onto the head of Jack's penis. The lube slowly ran down his shaft and onto his balls, but Ryan did not stroke or touch it.

Jack's penis was half erect, and Nathan's filled his cage as much as it could.

"Now I want you to use only one finger Nathan, and massage the lube into the head of Jack's cock," said Ryan. "But be careful. If you make him orgasm or lose his erection, you will not get out of your chastity belt for another week. We're going to tease him and keep him on edge."

Nathan knelt down in front of Jack and put one finger on his cock, then started to stroke. Jack let out a gentle moan.

"Keep going, faster, or he'll become flaccid, and you lose your chance at release," instructed Ryan.

Nathan struggled to get the balance right between keeping Jack erect but not letting him cum. He kept rubbing his fingers over the head of his cock and massaged the lube down over his shaft.

"Don't forget to play with his balls," said Ryan.

Nathan used his other hand and gently rubbed Jack's balls, already covered in lube that had dripped down from his cock.

Jack let out another moan and began to thrust.

"Wow careful" teased Ryan who was enjoying watching Jack squirm from the handjob and Nathan struggle to get erect.

Nathan stopped rubbing so hard and slowed down.

Ryan knelt behind Nathan and reached around his waist to hold his hands. "You can rub your hands over his thighs to calm him down," he said while moving Nathan's hands into position.

Jack's cock began to twitch as he let out more moans of frustration. Ryan moved Nathans hands back onto Jacks cock and started to rub. "I'm gonna cum, I'm gonna cum" screamed Jack.

They both quickly removed their hands leaving his cock twitching in the air. Jack managed to prevent himself from cumming, much to Nathan's relief.

Nathan played with a bit of precum leaking from Jack's cock.

"Would you like to taste it?" asked Ryan. "Go on, but just use your tongue. Don't put his cock fully in your mouth."

Nathan obediently stuck his tongue onto the tip of Jack's penis. He licked several times, enjoying the taste of precum.

Once all the precum was gone, Nathan stood up and shook himself. "I'm gonna explode Ryan, please can you remove the belt?" he begged.

"If anyone's going to explode it would be me," said Jack catching his breath.

"Looks like Jack's starting to get soft, better keep him up," said Ryan.

"But if I touch him he's going to cum," said Nathan. "I need out of this belt!"

He noticed Jack's cock was now getting smaller by the second. He jumped back on his knees and started to stroke his cock up and down, feeling Jack becoming harder in his hands.

Ryan reached over and poured a few more drops of lube onto his cock, which Nathan rubbed it in making Jack moan with pleasure. Each time Jack began to thrust, Nathan would stop all touching and let him calm down before stroke him again.

After another fifteen minutes of teasing, Ryan came over and congratulated Nathan. "Well done, you've managed to keep him on edge for half an hour. This is good for your first time. Next week we will try a full hour."

"So you'll let me out of the cage?" asked Nathan again.

"Yeah, soon" replied Ryan. "But first look at poor Jack. I'm sure he'd love to cum first."

"Yeah I'm ready, I'm ready," said Jack.

Ryan removed his trousers and took off his white briefs revealing his semi-erect cock. He left Jack secured to the chair but sat on top of him, slowly inserting Jacks penis into his ass and thrusting. He was still wearing his shirt and tie, and a pair of black socks.

Nathan walked closer to enjoy the show, focusing on Ryan's cock entering Jacks ass. It only took Jack two minutes before he was letting out a huge gasp and screaming "Yes, Yes, Yes" as he came inside Ryan. While cumming he struggled to move his legs and arms, but his restrained prevented him. All he could do was enjoy himself as Ryan took control of his cock.

Ryan stood up and winked at Nathan who was frustrated and agitated. He picked up his trousers and got dressed again, then released Jack from the chair.

"Don't worry we're not done," said Jack as he stood up and walked up the basement stairs.

"Should I follow him?" asked Nathan.

"No, let me put my belt back on then we'll grab some lunch. Have you eaten yet?" asked Ryan.

"No, I'm not hungry. I'm really horny. I thought.." started Nathan before being interrupted.

"Patience, what's the rush?" teased Ryan while signalling to follow him up the stairs.

Ryan invited Nathan to sit down at the kitchen table, while Jack went back outside to enjoy the sun.

"It only takes Jack a few hours before he'll be ready to play again," said Ryan.

Nathan couldn't bear waiting any longer.

"But how about we remove that belt off you while we wait?"

Nathan nearly collapsed at the thought of the belt finally being removed.

"First we need to take some safety measures, I'm sure you understand."

Nathan was confused but agreed just to speed up the removal of the belt.

"First let's get you fully undressed," said Ryan while lifting the shirt off Nathan. He then removed his pants, underwear and socks, leaving him naked apart from wearing the belt.

"Perfect, wait there."

Ryan went back to the basement, returning moments later with a small box. He set it on top of the kitchen table and opened it. Inside Nathan could see there was a few handcuffs, some rope, tape and some other bits and pieces.

"Put your hands behind your back."

The handcuffs were heavy and rigid. Nathans' arms were locked firmly in place behind his back. Ryan then took some rope and began to thread it between Nathan's arms, working his way from the wrists to his shoulders.

"How does that feel?" asked Ryan.

"I can't move my arms" replied Nathan struggling to see how much room he had to move.

"Perfect, now just to make sure," said Ryan reaching for a roll of tape. "Make your hands into a fist for me."

He peeled off a line of tape and wrapped it carefully around his hands until there was no skin left visible. He continued to peel bits of tape off and wrapping them around his arm. Finally, after a few minutes Nathan's hands, handcuffs and arms were completely covered in tape.

"Even better, there's no way you can move now," said Ryan pleased with his work.

Nathan pulled on his arms and hands to see if there was any way he could move his arms, but they were fixed firmly in position.

Next Ryan guided Nathan into the living room, where he helped get Nathan onto his knees in front of the sofa onto the soft carpet. Ryan took out another pair of handcuffs, but this time attached them to his ankles. He then took out a pair of scissors and cut a small hole through the tape restraining his arms, to reveal the chain from his handcuffs. He took a small chain from the box and attached them to his handcuffs and ankle cuffs.

"Can you stand up for me?" asked Ryan.

Nathan tried to get to his feet, but the chain was very short. He fell over onto his side, to which Ryan helped him up and onto his knees again.

With no way Nathan could stand up or use his arms, Ryan felt it was safe to remove Nathan's chastity belt. He left the room, leaving Nathan on his knees for ten minutes. Nathan struggled and moved around to get in a comfortable position. He wasn't uncomfortable, and enjoyed the feeling of being restricted, but wanted to test the restraints to see how secure they were. There was definitely no way he could get out of this.

While he was struggling, Nathan felt and heard a small click come from his belt though it remained firmly in place around his waist.

A few moments later Ryan walked through the door and sat down on the sofa in front of Nathan. He reached down and pulled the tube off Nathan's cock. He then removed the ring around his balls and finally the belt, being careful not to touch his cock or give him any stimulation. Now Nathan was fully naked and able to become erect.

Ryan rubbed Nathan's balls with his shoe gently while saying "does it feel good to finally be free?".

Nathan nodded and shook himself from side to side feeling the air against his free cock.

Ryan turned on the television and started to watch the news. After a few minutes, Nathan had to ask. "Please Ryan, will you play with my cock".

Ryan laughed and replied "no, no, no we have to wait for Jack and he's not ready yet. Just stay there and wait for him."

Nathans cock was as hard as a rock. Thrusting into the air out of frustration, he shuffled closer to Ryan and tried to put his cock between Ryan's feet. He managed to touch the head of his cock onto the tip of his shoe when Ryan pulled away and instructed him to wait.

After five minutes had passed, Nathan's cock was still fully erect. Ryan looked down and could see a small pool of precum oozing over his cock head.

"You really are gonna explode" teased Ryan. "Let me distract you then, remove my shoes for me."

Nathan struggled then said, "but I can't move my arms."

"You don't need them. You have teeth don't you."

"Oh, yeah okay" he replied bending down towards Ryan's left shoe.

He used his teeth to pull the shoelace. This wasn't easy and took him a couple of minutes. But it didn't look like Ryan was in any rush as he was focused purely on the TV.

Once the lace was untied, he was able to use his teeth to grip the back of his shoe, pulling it off revealing Ryan's white socks. He moved onto the other doing the exact same until finally, he had completed Ryan's command.

"Perfect," said Ryan, "did that take your mind off your cock for a few minutes."

"Yes," said Nathan as he noticed his cock was now semi-erect.

"Well then, keep going, remove the socks now."

Nathan continued to bend down and peel the sock off Ryan's foot, then moved onto the next one. It was easier to remove the socks than shoes, and once finished he took a minute to admire Ryans long and soft feet. This, of course, made his cock fully erect again. Ryan still refused to touch his cock or give him any relief.

Nathan tried again to rub his cock in between Ryan's feet, but he could barely get to his toes before Ryan pulled away. He gently kicked Nathan's balls with the top of his foot while saying "we must wait for Jack."

Nathan was going crazy just kneeling there waiting for something to happen.

"You fidget too much," said Ryan. "We're gonna have to train you up better. Though I do love seeing you this frustrated."

Ryan instructed Nathan to massage his feet.

"With my tongue," asked Nathan.

"Of course, do your best," he said.

Nathan knelt down again and stuck his tongue out onto Ryan's toes. His feet were cold and soft. Sliding his tongue down he continued to lick in circles around the sole of his foot before moving to his heel. Next, he pushed onto the other foot, licking from top to bottom. Nathan was enjoying submitting to Ryan, and the feeling of playing with his feet made him move a bit too fast for Ryan's liking.

"Calm down Nathan, this should be relaxing." shouted Ryan. He was getting himself excited and rushing too much, but he had never licked anyones feet before so didn't know what to do.

He slowed down and started to go gently until Ryan started to moan.

After twenty minutes of massaging Ryans feet, Jack walked into the room.

"I see you're training Nathan well. Nice to see his cock can still get hard after all that time being locked away." said Jack.

Ryan wiped the saliva off his feet and onto Nathan's chest then made room for Jack to join him on the sofa.

Jack sat down and reached over to cup Nathan's balls. "Your balls feel pretty full, when was the last time you jerked off?"

"I can't even remember it was so long ago," said Nathan.

Jack removed his hands rubbed Nathan's face before sitting back to watch the television.

Nathan knelt down looking at the two guys only dreaming of them rubbing and playing with his cock. They pretended to ignore him while he struggled even though they loved seeing Nathan so frustrated.

Another show finished, and they started to focus on Nathan again, who still managed to maintain his erection with a small glaze of precum almost an hour later.

Ryan moved his foot up to Nathan's balls and rubbed slightly, making Nathan groan.

"I think he liked it," said Jack. "Maybe he'd like to fuck them."

"I think he would. Go on then, you can rub your cock on them," said Ryan as he moved his feet together to grip Nathan's penis.

Nathan quickly slid his cock between Ryans feet and thrusted. He moaned in pleasure as his cock finally got the attention it so badly craved. But after only a few seconds Ryan pulled away leaving Nathan thrusting the air. He let Nathan recover then started to stroke his cock again. This went on for five minutes, only allowing Nathan a few seconds of pleasure at a time.

"Look, you have got precum over my toes," said Ryan. "Clean it off for me." Ryan moved his foot up to Nathan's mouth, while Nathan stuck out his tongue to lick his precum off.

Jack left the room while Ryan continued to tease Nathan, returning with a plastic box. He opened the box beside Nathan and produced a prostate massager. It looks like a small dildo with curves that would reach close to the prostate when inserted anally. Nathan knew what these were from looking online, but had never used one before. The only time he had tried injecting something into his ass was in the shower a few weeks ago, and he wasn't able to get it in.

"We think it's only fair you empty those large balls, but we don't think you're ready for an orgasm. Wouldn't you agree?" said Jack.

"No, I think I really need to cum. Please let me cum," begged Nathan.

"You can cum, don't worry. We'll get all that cum out for you." teased Jack as he poured some lube onto the prostate massager and knelt down behind Nathan. He reached around and held Nathan's chest as he guided him down towards Ryan's feet.

Jack poured some more lube onto his finger and slowly massaged around Nathan's asshole.

Nathan let out a moan, although inside he was scared he wouldn't be able to take anything up his ass like last time.

Jack spent another minute slowly rubbing lube around Nathan's ass until he felt ready to try the massager. Slowly he inserted the tip of the massager in only an inch then back out again.

Nathan let out a groan and kissed Ryans feet to distract him from the feeling. Although it did not hurt as much as he expected, it still felt somewhat uncomfortable.

Again Jack continued to insert only an inch of the massager in, gradually building up to the full length. After a few minutes, the device was fully inserted and touching against Nathan's prostate.

Jack moved the device slowly using the handle at the base. He tugged up and down, which made the tip massage slowly around Nathan's prostate. Each massage made Nathan moan in pleasure.

Ryan moved his foot back up to Nathan's mouth and inserted his toe. Nathan licked and sucked on whatever part of his foot Ryan put in front of him, all while Jack was playing with the device in his ass.

A larger pool of precum left Nathan's cock and dripped onto the carpet. "Looks like we have a leaker," said Ryan who reached for coaster from the side table. He placed it directly under Nathan's cock to collect any cum that leaked out.

Jack continued to play with Nathan's ass. He loved hearing him moan and watching the precum leak out slowly from his cock. This went on for at least fifteen minutes, while Nathan intermittently would attempt to thrust the air. If his hands had not be tied behind his back, he would reach around and tug his cock until it exploded with cum.

Ryan was also erect at the sight of Nathan's submission. He wanted some action too, so slowly removed his pants and underwear revealing his hot uncut cock.

"Let's put your tongue to some better use," said Ryan as he knelt down in front of Nathan and inserted his cock into his mouth.

"Oh yeah, that feels good," said Ryan as he thrusted into Nathan's mouth. Nathan only wished Ryan would suck him off as he pushed into the air trying to feel anything on his cock.

Ryan continued to thrust into Nathan's mouth getting faster and faster, while Jack slowly took his time massaging his ass.

After another long and frustrating fifteen minutes, Ryan was unmistakably ready to cum. Nathan had leaked out of quite a bit of precum, and there was another drop dangling from his cock ready to fall off.

Ryan removed his cock and started stroking it himself. He stroked faster and faster until a massive shot of warm cum hit Nathan's cock.

Nathan would have done anything to cum at this point, but all he could do was enjoy the feeling of Jack rubbing his prostate.

"Aw yeah, that was good. I love cumming." teased Ryan squeezing out the last drops of cum from his cock. "Don't you wish you could just cum like this?" Ryan started to massage the cum into Nathan's balls, making him moan out in pleasure.

Ryan sat down on the floor in front of Nathan and continued to cup Nathan's balls, massaging a mixture of his cum and Nathan's precum in. Nathan could feel a build up of cum move from his testicles to the head of his cock, but nothing came out.

The more Ryan rubbed, and Jack massaged, the more cum he could feel fill his cock. He started to moan out louder than before.

"Oh, shit, I think I'm gonna pee. I'm gonna piss myself," said Nathan.

The two guys just laughed and said: "I'm sure you won't".

Nathan's felt like he would burst, but no pee came out. Just a small stream of cum slowly oozed out of his dick and dripped onto the coaster.

"Oh-oh-oh," said Nathan confused at the new feeling he was experiencing.

Jack pressed a few more times into Nathan's ass until no more cum dribbled out from his cock.