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AJ walked back to his room quickly, trying to conceal his cum splattered shirt. He couldn't believe what had just happened. He had jerked off in front of his roommate. How had he let his dick make him that stupid? All he had to do was wait 25 more days and he'd be free from this dumb bet. He resolved to keep his head down and stay busy.
He lasted a little over a week.
The weekend was rough. All that free time that had to be filled, and no work help. He found that he could only exercise so many hours. Reading and tv weren't engaging enough to distract him. He offered to go into the office for some overtime, but his boss didn't want to pay him. Just when he thought he would crack, Monday rolled around. AJ gladly rolled up his sleeves and went to work. But even work could only hold his attention for so long.
He avoided the temptation to talk to Boyd on Monday. Just one more day. He almost crumbled on Tuesday, but Boyd was out. He regained his composure and fought through Wednesday. But Thursday broke him.
On Thursday, a rep from out of town was in the office for some meetings. She was a shameless flirt, and they had even hooked up once. She knew exactly how to tease AJ. Casually bending over and innocently offering him a great view. Finding a pretense to adjust his tie and feel his chest. Normally that would drive him wild in the best way. But with this cage on his cock, it just drove him crazy. There was nothing he could do. He was terrified she would find a way to grope his crotch and feel the cage. He went to see Boyd immediately after work.
"I need this off. Now. Stop being a dick. Let me jerk off or I will go insane."
"No way, you had your freebie already. 19 days left, just tough it out dude."
Boyd went to close his door, but AJ put his hand on the frame. "Please. I mean it, I really can't handle it. Isn't there anything I can do to convince you?"
AJ looked pitiful. Boyd tried not to smile. "Ok, fine. How about another bet? Double or nothing?"
AJ was terrified at the double, but did it really matter? He couldn't imagine lasting another 10 minutes, so the long term consequences seemed abstract. "Sure! There's another game this weekend, maybe -"
"No, no more sports. I want to know if you're really as horny as you say you are. I handcuff you and unlock you, just like last time. But this time, you only 60 seconds to cum. If you do, you're free. If you don't, and I lock you back up, this time for 60 days. If you cum after the 60 seconds, that's cheating and you get an extra 30 days for that."
AJ was stunned. He really did not want to jerk off in front of Boyd again. And now, under pressure? "That's not really my thing. Maybe we could do a coin flip or something?"
"No. That's the only bet on offer. Take it or leave it."
"Don't be such a perv dude!"
"Whatever. It's on the table if you change you mind." Body pushed AJs hand away and closed his door.
AJ was panicked. He knew instantly that he would take the bet, and that scared him. Something so embarrassing and repulsive was acceptable to him, as long as he got out of this cage. He was learning a lot about himself and didn't like it at all. But he had to be smart. The bet is available whenever he needs it - so why not wait a little longer, get extra horny and be absolutely sure that he can win?
AJ had a plan, and it got him through Friday at work. He had been dreading the weekend, but now he embraced it. He didn't try to avoid sexy thoughts any more, he reveled in them. The dull ache in his balls intensified. By Sunday morning, he couldn't take it any more and marched over to Boyd's door with purpose.
"I'll take the bet."
Boyd stretched and rubbed his eyes. He was wearing nothing but pajama pants. "What?"
"The bet? You know," he lowered his voice, "can I cum in under a minute?"
"Oh yeah. Sure. Come on in."
AJ didn't need coaxing. He took off his pants and went over to the bed. He swatted the bed a few times to create a crumb free zone, and sat down. The handcuffs were still on the tablet where they had been left the week before. AJ grabbed them and locked his hand to the frame.
Boyd smiled. He could see that AJ would lose the bet, just from the hue of his balls. AJ had obviously never been this horny before. Going from 0-60 in 60 seconds wasn't going to happen. But a bet's a bet, AJ deserved a chance. He got the key and carefully unlocked AJ and removed the device completely.
It rose to semi-hard quickly, but didn't quite get to full mast. AJ reached towards himself, but Boyd slapped his hand away. "No! Not until the timer starts."
Boyd opened a timer app on his phone, set it to 60 seconds and put it at the foot of the bed where they could both see it. "Go!"
AJ started stroking himself. It didn't take much attention to bring his cock to it's full length. He switched to a more vigorous speed, but his balls were too full and sensitive. The jostling hurt like hell and he had to back off. But time was creeping up on him. He tried to close his eyes and visualize Heather, but he kept looking at the countdown. Instead of seeing Heathers breasts, he only saw his time slipping away.
10
9
AJ found his pace and felt the jizz start to rise.
7
6
Boyd was impressed, and casually touched his own cock through his cotton pants. AJ was close but probably not close enough. It would be a photo finish. He decided that this was the last time AJ would ever cum by his own hand again.
4
3
AJ shut his eyes and started groaning, willing himself to finish.
1
0
"Times up! Hands off!"
AJ raised his hand over his and head and moaned in frustration. It was over. But his cock didn't know. He could feel himself get even closer to cumming. His moan changed from anger to fear as his cock started twitching. A small one at first, then two more in quick succession. Then sperm started erupting from his dick in small, regular squirts. Each accompanied by a low grunt.
"No! No!" It took a moment for AJ to realize what had just happened. He'd never had a ruined orgasm before.
"Bad luck dude. You went from 16 days left to 90." Boyd grabbed the chastity device and walked towards AJ.
AJ tried to cover himself, "Please man, no, let me try again! I can't do three months!"
"A bet's a bet. Don't take a bet you're not prepared to lose. Take it with dignity man." AJ stopped resisting and let his roommate lock his cock away again. But dignity was not something Boyd would let AJ keep for long. He already had a plan.
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