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.
