I awoke a few hours later, to a strange sensation surrounding my cock. As my eyes flitted open, I realised why. Paulo had attached some sort of milking machine to my cock that was now pulsing up and down building me up to yet another orgasm. I know we’d discussed this, and I’d consented, in our pre-meet discussions, but I hadn’t been prepared for how it would feel.

Paulo had asked, and paid a lot extra, for complete control of how and when I would orgasm this week. That included while I was asleep if he so desired. His goal was to send me home completely drained of cum, and clearly, he wasn’t messing around. The machine buzzed and pulsed and despite the massive double orgasm I’d had before I fell asleep, I could feel I was getting close again.

Seeing I was awake, Paulo reached out and started squeezing and tweaking my nipples. Combined with the effects of the machine, that’s all it took and I was filling the machine with a relatively small load. Paulo left the machine going a little past what was comfortable, clearly enjoying seeing the slight discomfort on my face again of being overstimulated. 

He brushed the stray hairs from my face and whispered, “Good boy, you can rest again now.” There was something about his soft and gentle voice that my body just reacted to, almost as if it was responding to his commands without my consent. I drifted back to sleep only waking to the sound of the shower running the next morning.

I stretched lazily in the bed, I have no idea how long it had been since I was last woken up to be milked. I reached down to scratch my balls and that’s when I felt something was different. I threw the covers off myself and looked down and that’s when I saw what was different. A shiny metal cage was now wrapped around my dick, enclosing it. Complete with a small metal padlock at the top to hold it in place.

I didn’t notice the sound of the shower shutting off, or the bathroom door opening, so I was startled when Paulo was standing next to me wrapped in just a towel, greeting me with, “Good morning my beautiful boy.” It was the first time I’d seen him out of his clothes, and god did he look good. “Do you like it?” He asked and it took me a few moments to realise he was talking about the cage, I was so distracted I’d forgotten it was there. 

Rather than answering his question, I asked one of my own, “I thought you wanted me to cum?”

“I do, my boy, I do. But only when I’m here. I have to go to work and this will keep your cum safe for me while I’m gone,” he replied matter of factly.

I nodded slowly, still not really taking it all in. “Is it ok?” He asked, checking in with me. I took a moment to really think about it and I liked trying out new things as part of my work, so I agreed. It was to control my orgasms after all, and that’s what he was paying extra for.

He smiled and allowed the towel around his waist to drop to the floor. My jaw dropped with what I saw, I thought I had a big cock, but this guy’s was huge ! I started to imagine him fucking me with it and having to muffle my moans from the intensity as he breached me for the first time.

My cock started to try and get hard, and suddenly I understood the effect of the cage. Paulo giggled, “Maybe if you’re a good boy, I’ll let you play with this when I get back,” he teased, lightly stroking his cock which seemed to be getting even bigger as he did.

I closed my eyes and tried to will my cock  not to try and inflate inside its new confines, causing Paulo to giggle again. Once he was dressed, he kissed my forehead and headed to work. Leaving me alone, naked and locked.

The rest of the week continued just like this, I spent my days naked and locked. Then as soon as he got back, I’d be unlocked and the milking would begin all over again. I lost count of the amount of times he made me cum over the course of the week. Occasionally, he’d give my cock a rest and have me suck his instead. I think it was the first cock I hadn’t managed to completely swallow, but he seemed to enjoy it just as much.

On our last night together, when he was holding me after another orgasm, he asked me, “You’ve been such a good boy this week, doing everything I’ve asked. Is there anything I can do for you?” Twirling the ends of my hair between his fingers.

I barely thought about it for a second before blurting out, “Will you fuck me?”

He chuckled, “Are you sure about that, most men struggle to take me and once I’m in, I don’t like to stop.” I shivered in anticipation, my cock again making the decision for me, “Yes!” I breathed out. 

“Ok boy, let’s get you prepared,” he agreed. So I jumped off the bed and went to my overnight bag to retrieve the lube and a condom. He laughed at how excited I was, but I’d been dreaming of this moment since the first morning when he was teasing me after his shower. Returning to the bed, I got on all fours so that he could start getting me ready to take him.

Applying a generous amount of lube, he slowly opened me first with one finger just swirling about to give him enough room to insert a second. With more lube, he slipped a second finger and started to scissor me open. When he felt he couldn’t do any more with the two fingers, even more lube was added and I felt a third digit press inside me. It felt good but it wasn’t what I needed, I needed his cock and I needed it now.

“Paulo, please,” I begged.

“Just a little longer, I don’t want to hurt you.”

Sure enough, when he didn’t think he could do any more to prepare me, he slipped his fingers out causing me to whimper at the loss. He made easy work of slipping on the condom and covering himself in lube before adding more of the cold goo to my entrance. Then finally, finally , he was pressing against me trying to push his way past the resistance my body made.

I tried to relax my muscles and with a satisfying pop, his head was inside me. He gave me a couple of minutes to get used to this new intrusion before he started to ease himself in inch-by-inch. He wasn’t just long, he was girthy too, almost like a tin can forcing its way inside me. But Paulo clearly, knew what he was doing, with some clients I needed to tell them to slow it down, but with Paulo, he was almost achingly slow.

Each new push was forcing me to groan at how full I felt. When he finally bottomed out, he released a sigh of relief and said, “Damn, look at you, you’ve taken all of me, I’m impressed.” I could hear the smile in his voice, and mixed with his praise I mewed, “Fuck me, please, please fuck me.”

Tentatively, he withdrew just a couple of inches before pushing them back in again. He repeated this slow and steady rhythm, building up in the number of inches he pulled back before pushing all the way in again. Once he was able to pull out so that just his head was left inside and could comfortably move all the way back in, he knew I was ready.

Holding onto my waist, he picked up the pace and was now thrusting in and out of me harder and harder. If it wasn’t for the strong grip he had on me, I think the force of it alone would have sent me flying down into the bed. It was rough, but I felt so alive. Each movement was now pounding into my prostate, taking me apart from the inside.

I felt my orgasm building inside me and I hadn’t even touched my cock, neither of us had. I didn’t even know if I had any cum left in me after the week we’d spent together. With a few more slams into my ass, I was cumming hands-free, shooting yet another load underneath me. Ok, it was a small load, but I somehow managed it.

Feeling me clench around him as I let go of my release had Paulo tipping over the edge too. He filled the condom inside me and the pulsing sensation felt incredible after the intensity of his pounding. Even after he was done, he continued to fuck me, teasing us both until he really couldn’t take the sensation any more. He carefully pulled out of me and guided me back to the bathroom, just as he did on our first night together. He disposed of the condom and set the water running in the bath.

When it was ready, he climbed in and told me to join him. It wasn’t a perfect fit, but it felt good. I was in his arms and he just held me in the warm water, telling me to relax into the feeling. Everything was sore, my ass, my muscles, even my throat was sore from all the moaning and screaming I had done.

Just as on the first night, he picked up the soap and started washing my body. It felt more like an exploration than an actual effort to get us clean like he was trying to commit my body to his memory before we parted tomorrow. It had been an intense week, and one I knew I would never forget.

The next morning, I woke up to an empty hotel room. Paulo had told me he had to leave early for his flight, so it wasn’t a surprise, but I was a little disappointed I didn’t get to say goodbye. I grabbed my clothes for the first time since I’d arrived and got dressed, I could shower back at home. I reached inside the pockets of my trackies and found a small envelope, which surprised me as the agency handled all of the money as a sort of escrow service.

I opened it up, and inside was cash, a lot of cash, and a note.

My dear boy,

Thank you for such a memorable week, I hope you aren’t too sore today.

Take care,

Paulo x

I slipped the note and cash away in my pocket and gathered up my toiletries. I took one last look around the room and smiled as I headed home.

The trip back to my apartment was uneventful until I got to the front steps of my building. There was someone sitting blocking the door, they heard me approach and looked up. Beautiful chocolate eyes stared at me as he exclaimed, “You’re alive!”

“Olly? What are you doing here?”