I followed Brian into the gym. Coach had told Brian to come just after closing time and of course he’d told – not asked – me to join him. Knowing that he now held the keys quite literally to my orgasms and hoping that if he passed Coach’s challenges and got off tonight that he might be in a good mood and more inclined to release me, I hadn’t hesitated. Coach was standing just inside,

“Ah, right on time boys. As promised Brian, I’ve got a little challenge set up for you tonight and if you want some release, I expect you to perform. I see you’ve brought your boy along to help; I thought you might so don’t worry, I’ve got something for him too. First things first, get out of those clothes boys, you won’t be needing them.”

If Brian was embarrassed stripping down in front of coach with his cock still locked, he didn’t show it but I couldn’t help but blush. I also couldn’t help but look at Brian’s muscled back, and his perfect bubble but and imagine dropping to my knees and… my dick started to strain in it’s cage and I groaned quietly. Brian looked back at me and saw immediately my predicament, he smiled somewhere between reassuringly and a smirk which only served to make me harder.

“Your challenge is one of endurance and since you and Peter’s upper body strength scores aren’t where they need to be, we’ll start there.” Of course, it was my upper body strength scores that were bringing us down and I desperately wanted to defend myself but really, what was there to say. “Come here and lie on your back.”

Brian moved over to where Coach indicated and lay down, staring at the piece of thin rope hanging from the ceiling. Coach knelt and firmly lifted Brian’s legs so they were bent, feet flat on the floor and spread so that Coach could kneel between them, with unobstructed access to his caged dick. Coach took the rope and neatly tied it securely around Brian’s balls. As Coach stood, he tugged on the rope, pulling Brian’s balls up and eliciting a disgruntled grunt from the jock. Next Coach, used a pair of handcuffs to secure Brian’s wrists together and then took the other end of the rope which I could now see hung from a pulley and brought it down toward Brian’s hands.

“Lift your arms up please.” Brian did so but he glared continuously at Coach as he pulled the rope and tied it to the cuffs so that it pulled on his balls slightly upwards with his arms held vertically straight. It was ingenious really; eventually Brian’s arms would get tired and he’d want to lower them but to do so would pull on his balls so he could either feel the burn build in his arms, lower his arms and pull up on his balls or try to raise his hips and quickly tire his abs. Coach stood back and admired his work and nodded to himself.

“So here’s the deal Brian: you said you wanted release and to earn that right, you’re going to have to last as long as it takes Peter here to complete 100 push ups.” My heart sank and my jaw dropped a little, oh gosh please no. I so badly wanted to impress Brian not just because I wanted him to let me out of my own cage but because he was, well, perfect! I started to stammer but Coach hadn’t quite finished.

“Oh, I almost forgot these.” Coach went over and brought over two dumbbells and gave them to Brian. They weren’t heavy but I knew it wouldn’t take long for fatigue to quickly set in. Both Brian and Coach stared at me expectantly and my bottom lip quivered but I got down on my knees, took position and started pumping out push ups as quickly as I could. I easily got to 20 but my pace slowed. At 32, my arms shook as I reached my lowest point and I didn’t have the strength to get back up. I collapsed onto the ground panting, sweat shining across my forehead. My arms ached as I scrambled to my knees. Looking over at Brian I could tell he wasn’t happy with my performance so far and his arms had a slight quiver in them as well.

“Come on boy, you can do better than that. I’ve seen you do it in our morning training sessions, so get after in.” I nodded once and resumed my position, managing to squeeze out another 21 before collapsing again. I started to stammer an apology to Brian, but as I glanced up noticed he was not taking any notice, instead he had his eyes closed, his arms slightly lowered relaxing his elbows and his hips arched in the air, his toned tummy shaking with strain as his abs and thighs struggled to hold himself up. Even as I watched, his posture slipped slowly and his balls began to stretch painfully higher.

I was mesmerized until his loud groan snapped me out of my reprieve and he pushed his arms straight back up, collapsing his hips to the floor with an almighty effort.

I started my push ups again, my arms on fire, my abs starting to ache and sweat dripping into my eyes but try as I might, I simply wasn’t strong enough and after only 13 more push ups, collapsed again. I got to my knees and looked at Coach almost with tears in my eyes, helpless to continue but afraid to stop. As he had before in my times of awkwardness, Coach came to my rescue, stepping over and dropping to one knee, putting a firm hand on the back of my neck and squeezing tightly. I drew into his touch, head instinctively dropping as he spoke softly just above my head,

“It’s okay boy, you’re doing a really great job. You’re well over half way and I wouldn’t have set the task if I didn’t think you could do it okay?” I nodded against his hand. “Good boy. Now, you can do the remaining push ups on your knees if you need.” I nodded again and tried not to think about the fire in my arms as I started again. At 85 push ups, only 15 to go, I stopped, exhausted on all fours, and looked over at Brian. His balls were now stretched at what must have been a painful height and a look of fierce determination on his face was being eroded by exhaustion.

I knew I had to hurry. Getting back down I drew on every reserve of strength I had and pushed out to 90… 95…. 97…. 99….. 100…. And fell to the floor, unable to move even to kneel. I heard more than saw coach unhook Brian from his predicament and we both lay panting, exhausted next to each other. As we gradually recovered our breaths, I rolled onto my back and sat up. Brian rose and stood in front of me and I wanted to apologize for how long I’d taken but he simply extended a hand and helped me up. Placing a hand on my shoulder he smiled,

“Good work boy. I think we’ll focus on push ups next training eh?” I didn’t know if he was joking but frankly I didn’t care. The words “good boy” were stuck floating in my brain and I flushed with excitement.

“Well Brian,” Coach started, “you passed your challenge and earned your release, though I’m going to give you a choice. You’re in that cage to show solidarity with the rest of the team and I’m happy to let you out for tonight so that you can jerk off and then lock back up before you go to bed; or, since you seem to be doing so well training Peter, I’m inclined to let you out of the cage permanently. I figure if I do, you might find some, shall we say interesting, ways to improve his motivation. Of course, if you choose to be released permanently, I don’t want you to immediately start terrorising poor Peter here, starting to abuse your power so before you go I’d make sure you’ve cum and are not at all horny so that you’re thinking with your Captain’s brain, not your horny balls. Tell me Brian, have you ever been milked before…”