Progression Ch. 07: Decision

The next few days went pretty slow as Nathan counted the minutes until he could see Jack and Ryan again. It didn't help his frustration than Kevin, who was now sleeping in his bed, had quite a high sex drive. He was always demanding handjobs and blowjobs, which kept Nathan in a constant state of arousal.

"I'm off to see the guy I told you about," said Nathan sitting on the end of his bed talking to Kevin.

"Oh is he gonna remove the belt for you?" asked Kevin.

"I don't know. Probably not," said Nathan.

"Have fun. Are you coming back home tonight?" asked Kevin.

"Yeah probably as I have work tomorrow. I'll see you later on," said Nathan putting on a change of clothes then leaving Kevin for the night.

Once at Jack and Ryan's he rang the doorbell and was greeted by Ryan, who was wearing a tight black t-shirt and blue jeans.

"Did you forget about the sensors the other night?" teased Ryan. "I see Jack has made you more curious about playing with your ass then?"

"Oh yeah, sorry Ryan. I got drunk with my friend then came back home. I completely forgot," explained Nathan.

"Oh you were with a guy?" laughed Ryan. "What did he think of your situation?"

"Yeah he doesn't understand," said Nathan much to Ryan's amusement.

Nathan followed Ryan inside but was stopped and told "Oh, there's no need for you to be clothed when you're in our house. You can remove all those for now."

Nathan removed his clothes and threw them onto the floor, before walking up to Ryan and stroking his arm.

"Oh, you've gotten more confident," said Ryan pushing his hand off. "Don't just throw your clothes on the floor. Pick them up and fold them. You can leave them on top of that cupboard." he said while walking into the kitchen.

"Sorry, yes of course," said Nathan picking up his clothes.

He could hear Jack and Ryan talk as he lifted his clothes from the floor, folded them and gently placed them on top of the cupboard.

"Looks like Nathan's found himself a friend the other night," said Ryan to Jack.

"Oh really, how did that work?" asked Jack.

"Who knows, but that's what the alert was about the other night," explained Ryan.

Nathan entered the room, naked wearing nothing but his chastity belt.

"You should have brought him over," said Jack to Nathan.

"Oh, he's not really into any of this," explained Nathan.

"That's a shame," said Jack. "You must be so horny not being able to have sex. Do you think you'll see him again?"

"Yeah, he lives with me. He's my flatmates best friend," said Nathan.

"Oh, this is interesting. So your friend knows about the chastity belt but isn't interested in it?" asked Jack.

"I don't know, he was weird about it at first, but as you know we ended up having sex, even if it was only for a few seconds," said Nathan in disappointment.

"Oh yes. We were very disappointed in you," said Jack. "But you can make it up to us tonight."

Nathan felt his cock bulge against his cage. He was so horny and just wanted to suck the guy's cocks, lick their bodies and play with them.

"Okay let's go," said Jack as he directed Nathan down into the basement with Ryan.

When they got to the bottom of the basement, Jack told Nathan "Get on the bed, on your hands and knees and face the headboard."

Nathan instantly did as he was told and got onto the bed, revealing his ass to the two guys.

Jack followed him and brought out a stool to place under Nathan's stomach for support. It had four restraints attached, one for each foot and hand. He locked them in place leaving Nathan unable to move, with his ass still in the air.

"Since you seem to be in need of some ass play, we thought we'd treat you," said Ryan with an evil grin on his face. Jack set up his camera and aimed it directly towards Nathan's ass.

"Here is your challenge Nathan." started Ryan. "We are going to insert different sizes of dildos into your ass. Each one will be bigger than the last. We are going to remove the belt and give you the chance to cum tonight. I'll rub your cock with my hand at any speed you want. Whatever size of dildo you can keep in will decide how many seconds you will get from my hand. Clear?"

Nathan wasn't entirely sure of the rules but nodded anyway just glad he was getting some form of sexual relief.

"This is the smallest one. If you can hold it in your ass for five seconds you'll have five seconds to make yourself cum," said Ryan as he picked up a small dildo the size of a pen and rubbed some lube over the tip.

Slowly he inserted it into Nathan's ass. When it was rooted in his ass, Ryan said: "Your time starts now."

Nathan squeezed as hard as he could, making sure to hold the item in his ass. Much to his surprise, he was able to keep it there with no problems.

"Well done," said Ryan. "Now for the next one. If you can hold this one, you'll get an extra five seconds."

Ryan picked up a slightly larger dildo and inserted it again into Nathan's ass. This time as Ryan took it, Nathan could feel a small drop of precum leave his cock.

Ryan, noticing the precum drip from the cage, reached over and wiped it off.

"I think he likes it," said Ryan to Jack.

Jack winked at Ryan and adjusted the camera some more.

"Okay hold this for five seconds, Nathan," said Ryan.

Nathan didn't squeeze as tightly this time, and before the five seconds were up the dildo started to slide out of his ass.

"Oh sorry, your time remains at five seconds," said Ryan taking out an even bigger dildo and inserting it into Nathan's ass. Again another drop of precum left his cage.

"Okay hold it for five," said Ryan as he let go.

Nathan squeezed as hard as he could, determined not to let it slip out.

"Excellent, you get another five seconds. That's ten in total," said Ryan.

"Please Ryan, can you push it in and out of my ass. I really want to feel it thrust inside me," begged Nathan.

"Well due to your mistake a few days ago I'm sorry we can't allow it. If we did you'd never learn how serious we are with your chastity. You only touch your ass and cock when we say so," said Ryan.

"Please," said Nathan. "It's so frustrating."

Ryan picked up the next sized dildo and inserted it into Nathan's ass. This one took a bit longer to position as his ass was not used to the size.

Nathan squeezed as hard as he could, holding the dildo in place.

"Well done, that's another five seconds. You have fifteen seconds now. Let's move onto the next." said Ryan.

Nathan was leaking a lot of precum from his cock. Jack zoomed into his cock with his camera making sure to capture everything.

Ryan inserted the next sized dildo slowly into Nathan's ass. He gave out a small groan. It was half of pleasure and half in pain. Slowly Ryan pushed it deeper and deeper into his ass.

"You're doing well. Now hold it for another five seconds," said Ryan.

Nathan panted and breathed heavily as he held onto the dildo with all his strength releasing, even more, precum from his cock. All he wanted was for Ryan to thrust that dildo deep and hard into his ass.

"Perfect, that's five more seconds. Twenty in total," said Ryan as he reached for the next one. Slowly Ryan inserted the dildo making Nathan shout out "Ouch, ouch, ouch I can't. Aww"

"Are you sure?" asked Ryan. "Is it too much for you? We can stop."

"Yes, yes I can't take that one," begged Nathan.

"Okay," said Ryan as he put the dildo down. "So you have a total of twenty seconds to make yourself cum."

Nathan was thrilled. He was so horny he thought it would only take him one second to explode the cum out of his cock.

Jack reached over to his laptop and clicked a button to release the chastity belt.

Ryan, however, did not remove the full belt. He just slid the tube off, revealing Nathan's cock that instantly because fully erect.

Nathan was still on all fours with his feet and hands attached firmly to the stool under his belly. The view from Jack's camera was of Nathan's ass hole, then directly below his cock aiming towards the ground, being held by the back of the stool.

Ryan placed a timer with the numbers "00:60" in front of Nathan's head so he could see it. The numbers started to count backwards.

Ryan squirted some lube onto his hands and rubbed it in. He then squirted some more onto Nathan's cock head, still not touching his penis.

The timer finally reached "00:25" and Ryan said "do you want me to start fast, slow, firm, soft. This is your twenty seconds, you tell me how you want it."

"Please just stroke my cock, fast and hard, then slow. Just stroke it, please. I'm so horny," begged Nathan as he watched the clock finally reach to "00.20."

As soon as his twenty seconds started, as promised, Ryan held Nathan's cock firmly in his hands and tugged to his command.

Nathan let out a moan. "Oh yeah, yeah, fuck me," he screamed.

Ryan kept on pulling harder and harder. The timer reached "00:10". Nathan started to panic. "No no I don't have enough. Oh yeah, this is it... Oh... Faster! faster! please."

Ryan kept on tugging faster until the clock reached "00:00" then he quickly removed his hand said, "Times up!"

Nathan screamed "No. Please, I'm so close."

"Sorry Nathan you knew the rules," he said.

Nathan rubbed himself on the back of the stool, trying to finish himself off. But Ryan reached for his cock and pulled it away, giving him no relief.

"I really thought twenty seconds would be enough," said Ryan to Jack.

Jack agreed then said "But that made one hell of a video. The fans are gonna love this."

"Please Ryan. Please, Jack. Just finish me off. It's been so long," begged Nathan. But Ryan just held his cock down making sure Nathan's attempted thrusts achieved nothing.

Jack then brought a bucket of ice over and started rubbing a cube around Nathan's asshole. "Ouch, ouch that's cold. Please," he begged while he cock slowly became smaller.

Jack move the ice cube down over Nathan's balls, that quickly shrivelled tightly against the metal ring that encased them. Next, he pushed the ice cube over Nathan's cock that was already mostly flaccid.

"Perfect," said Ryan, reaching for the tube and attaching it to Nathans penis.

He struggled in his restraints still thrusting, trying to get some relief.

"Next time maybe you'll try the larger dildo," said Ryan.

"I'll try it now, please just thrust it into my ass and I'll take it," said Nathan. But Ryan was firm and began to untie Nathan from the restraints.

Once free Nathan lay back on the bed, exhausted and hornier than he'd ever been. Ryan tidied up his gear and Jack finished some editing on the camera.

"That was hot," said Ryan to Nathan. "We really love playing with you."

"Yeah I love it too, but I didn't think it would be this hard," said Nathan.

"So what about this new friend of yours then. Must be hard for him not getting to play with your cock," said Ryan.

"Yeah he was reading up about chastity belts, but I don't think he really understands it," said Nathan.

"Well maybe you should bring him over here and let us show him," said Ryan.

"Oh no, he's really not into this sort of thing. He's just a regular guy," said Nathan.

"We're all regular Nathan. We have just opened up to our sexuality. There will be some interests in there he hasn't shared with you yet," said Ryan.

"Yeah maybe, but if I go too fast he'll just get freaked out," said Nathan.

Ryan said "take your time and go as slow as you want. But if it makes things interesting, you can bring him here, and as a reward, we will let him fuck you for one night. You'll still have to wear the chastity belt, but we will ignore the sensors for one night. You don't have to do it here, you can do it in private one night. But only after you have introduced him to us."

"I'll think about it," said Nathan as he sat on the end of the bed.

"Why not show him the video from tonight. It's a pretty good one, and apparently, he liked your ass," said Jack with a wink. "I've just uploaded it now, so it's on our profile."

"Yeah maybe," said Nathan.

"Okay time for Jack and me to play," said Ryan putting his arms around Jack.

Jack removed his pants and underwear, revealing his smooth and toned behind. He got onto all fours on the bed, with his ass in the air.

"Nathan, get him ready," said Ryan.

Nathan reached over and started to play with Jacks cock.

"What are you doing?" asked Jack. "He means my ass, get my ass nice and wet for him."

Nathan was confused and asked, "with the lube?"

"No silly, use your tongue. Build up some spit and lick Jacks ass," demanded Ryan.

Nathan had never licked anyone's ass before, but the idea did turn him on. He bent down and placed his head near Jack's ass cheeks. He stuck out his tongue but couldn't reach.

"Get your head in there," said Ryan gently pulling Nathans head towards Jacks ass.

Nathans' nose pushed between Jack's cheeks, revealing a sweaty and manly smell.

"Now lick and get it nice and wet for me," said Ryan.

Nathan built up the spit in his mouth and licked around Jack's asshole. He moaned in pleasure, as did Nathan in frustration.

Jack's cock swelled up, and Nathan reached under to play with it. But Ryan quickly pushed his hand away denying Jack's cock any pleasure.

"Now my cock," said Ryan, who was now standing naked with his erected cock aiming towards Nathan's mouth.

Nathan switched Jack's ass for Ryan's cock, and he sucked and licked much to Ryan's pleasure.

"My mouth's dry," said Nathan gasping for air.

"Here," said Ryan passing him a bottle of water. He took a big gulp of water then swallowed and sucked on Ryan's cock again.

"Now back to Jack's ass," said Ryan.

Nathan moved back and licked Jack's ass again. After a few more seconds Ryan gently pushed him out of the way and inserted his cock into Jack's ass. It slid in easily with Nathan's spit acting as the lubricant.

Ryan penetrated, faster and faster, moaning in pleasure. Each thrust made Jack gasp in a mixture of pleasure and pain. Finally, after fifteen minutes Ryan groaned and ejaculated his cum deep into Jack's ass.

After a minute to cool down, Ryan pulled out. "Nathan, clean up Jack's ass for him. Get all that cum out," he commanded.

Nathan instantly moved his head back into position and stuck his tongue into Jack's ass. He enjoyed the taste of Ryan's cum and the smell of Jack's sweat.

Ryan made Nathan continue to lick, checking every minute to check semen was still coming out. After a few more minutes no more cum was leaking out and Nathan was allowed to stop.

The three of them lay on the bed for fifteen minutes, talking to Nathan about his new friend and hearing how frustrated he was. Then it was time for Nathan to leave. The guys reminded him of their offer to let Kevin have sex with him if he introduced them.

Nathan got dressed at the door, then left to go home. His mind was mixed with thoughts about wanting to cum, getting the handjob by Ryan, licking Jack's ass, having sex with Kevin. Nathan was hornier than ever and didn't know how he could continue without cumming. Next time he would have to take every dildo to make sure he could cum.

Finally, when he got home, he went straight up to his room. It didn't take long before Kevin knocked on the door and joined him.

"So have fun?" asked Kevin.

Nathan was actually relieved to have someone to talk about his experiences too. But he had to be careful not to drown him in too many details too fast.

"Yeah it was fun, still didn't get to cum," said Nathan.

"That's a shame," said Kevin who started to undress. "The thought of you sucking some other guy turned me on. I was downstairs with Jeff not listening to anything he said, just thinking about you. Since you haven't cum, you're still horny, right?"

"So horny," said Nathan.

Kevin removed his underwear and sat on the bed. Nathan got onto his knees and sucked on Kevin's cock. He felt like his cock would explode from the constant sexual teasing happening in his life. With all the thoughts running around in his head he blurted out. "I told them about you tonight. They want to meet you. They said that they would let us have sex and" but he was interrupted.

"Oh, I don't know," said Kevin. "Look it's kinda hot and all, but that's maybe too much. And who's they, I thought this was just a guy you were playing with."

Kevin pulled his cock away and put his underwear back on.

"It's two guys I met at the sex shop. They're really friendly. They just want to give you the chance to ask questions. I'm sorry if I'm coming on too strong. I'm just so horny," explained Nathan.

"Look maybe in the future. I don't know where I am with all this," said Kevin.

The two lay in bed with each other as Kevin contemplated about what he was being introduced to while Nathan was filled with horny thoughts.

Kevin had an important decision to make. If he wanted to play with Nathan, he would have to meet his new friends. But if he didn't, all he could get was blowjobs. Would that be enough for him?