I’m not sure that I would have had Brian’s will power. Then again, I guess that’s why he’s the Captain, and I was just a boy; he chose the long game, to be milked now and then released permanently from chastity. Selfishly I was thrilled. I figured Brian would be much more accommodating if he wasn’t locked up and that I would get some much needed relief very soon. Coach brought Brian to the other side of the gym and had him lie on his back. Coach used a pair of cuffs to secure his wrists together under his ass and a small chain to connect his ankles. It wasn’t immobilizing but there was certainly enough restraint that Coach would have no issues enforcing his will. Coach pulled out a key and expertly unlocked Brian’s cage, sliding it off carefully along with the cock ring section. Brian’s dick was instantly rock hard standing gloriously at 7” of perfection, a thick vein throbbing along the side, his head bulging with need for attention. I wanted nothing more than to sink to my knees and worship that cock, knowing that I could bring Brian in his current state to the edge in moments and swallow his delicious seed and feeling a thrill as he exploded inside me. Coach had other plans.

Brian squirmed a little on the floor, testing his mobility as Coach got up and fetched an odd looking contraption. I looked on confused while Coach slid a tube over Brian’s dick causing him to groan and arch his back.

“Alright Brian, have you ever been milked before.”

“No Coach, please do that again Coach.” Coach chuckled,

“I’ll do it more than a few times Brian but I don’t think you’ll be asking me that in an hours time.” And without waiting for a reply, Coach reached down and twisted a small valve and suddenly the tube on Brian’s dick, pumped up and down slowly.

Brian shuddered, closed his eyes and moaned. After a week of being locked the sudden stroking on his dick was clearly sending waves of pleasure coursing through Brian and building him to orgasm very quickly. While Brian was lost in his own pleasure, Coach came over to me and put his hand on my shoulder, looking me firmly in the eye. I was torn between looking at my feet, wanting to peek at Brian’s flexing muscles as he tensed and relaxed and being utterly captured by Coach’s eyes.

“Your Captain still has the keys to your cage young man but that doesn’t mean you can’t have some release tonight.” My balls ached for release and with Brian moaning and writhing right next to us I certainly didn’t need extra motivation to want it. Coach knelt and took my cage in one hand. My legs gave just a little and Coach chuckled again,

“Easy there boy.” Coach took something out of his pocket and fiddled with the cage. I winced a few times as a sharp pinching feeling jolted the sensitive head of my caged dick. After a minute, Coach took my cage in a firm hand and shook it, standing back up over me. I looked down and saw little strips of Velcro had been wrapped around the end bars of the cage.

Seeing Coach’s hand right on my trapped cock I couldn’t help but grow. Blood throbbed through my dick and I swelled inside my cage until – Owwwwieeeee! As my sensitive head grew, it pressed into the Velcro on my cage with a sharp pain. From that moment on I was trapped in a vicious cycle: the throbbing of my dick pressed it painfully into the Velcro, making me think about my situation and about Coach’s control and making me throb all over again.

“Now,” Coach said loudly enough to jolt even Brian from his rapture. Here’s how this works boys: “Brian, that machine is going to continue up and down, stroking your dick. It’ll feel pretty great at first I’ll bet - ” Brian didn’t need to say anything to confirm that – “but once you cum I think you might not feel so thrilled about it.” Brian’s face looked horrified.

“That’s it Brian, I told you I was going to drain every last drop of cum out of those balls and I meant every last drop. Don’t worry though Brian, I’m going to give you an out. Your boy Peter here is still caged, but I think he did such a great job with his push ups tonight I’m going to give him a chance to cum through his cage. I’ll turn that milking machine off either when your balls are dry or until Peter here manages to cum.”

With that, Coach brought over a chair and sat down near Brian’s head and they both looked at me standing like a kangaroo in headlights expectantly. I looked down at my caged dick again and suddenly swelled with the attention, bringing back that sharp pain. Oh crap! I wanted so badly to please Brian but I didn’t know what to do. How was I supposed to get myself off while caged. I bit my bottom lip and reached down, tried to slip a thumb through my cage and rub the head of my dick. I couldn’t get my thumb through but with my dick swelling, I could still rub my glans and it did feel good. It felt really good. Even with the pain, I found myself moaning very softly and thrusting my hips slightly. I continued for a few minutes and the confliction in me grew as the pain grew more and more intense over time and I inched impossibly closely toward climax. My rhythm was interrupted by a guttural groan from Brian. I looked down to see him arched, his every muscle tensed, eyes closed as he exploded and shook, his orgasm wracking through his body. His orgasm didn’t subside. As the milking machine continued to stroke on his now hyper sensitive dick his groan turned almost to a yell and his squirming turned to thrashing.

Coach quickly knelt and took Brian’s head in his hands, holding him still; looking Brian dead in the eye, focusing him. As Brian quietened slightly, Coach grabbed a black gag from his back pocket and quickly fitted it to the tortured boy.

Brian’s eyes pleaded with Coach who simply re-took his chair and Brian turned those desperate eyes to me. I realised I had stopped rubbing my own sharply pained glans and lost the ground I had made towards climax. I yelped and started again but I knew it wasn’t going to be enough. I knelt down, licked a finger from my other hand and reached around to finger my hole. I’d always liked ass play and loved the feeling of something playing with my hole. With the added stimulation I moaned and began thrusting my hips. Coach praised me,

“Good boy,” and put his feet up on Brian’s chest clearly enjoying the show.

I began to lose myself in the rhythm. After a while Brian’s almost continuous moaning took on a frenzied edge and I guessed that he’d cum again. I begged myself to go faster, thrusting, sweating, panting and through it all, trying not to cry from frustration and from the biting of the Velcro pinching into my increasingly sensitive glans. I was aware of Brian shouting though it was muffled by the gag, it was unmistakably please, please, please, begging me over and again to cum. Fuck I was trying! At long last I brought myself closer to the edge. If it hadn’t been over a week since I’d last cum and if I wasn’t desperately horny, there’d be no way I’d have been able to get even this far but as it was, I could feel myself frustratingly close. On a knife edge, I sobbed with frustration and again, as he seemed to be doing a lot lately, Coach came just as I needed help. Without words, he knelt behind me, wrapped one arm firmly around my chest and with the other, took one of my nipples and squeezed hard, bringing his mouth close to my neck so I could feel the hotness of his breath. And suddenly I was in the safest place in all the world and I came. My body wracked with waves of pleasure as shot after shot of hot, creamy cum shot from my caged dick, throbbing in it’s cage, swelled and tortured. I arched back as Brian had and were it not for Coach’s support would have fallen. He held me as my orgasm subsided slowly and left me panting, collapsed against him. Quietly, Coach  lowered me to the floor, stood and calmly released Brian.

“Well done boys. I’ll see you at training.”