How I Found a Keyholder Ch. 02

2.a: A verbal contract

I had the best night's sleep I'd had in weeks, or maybe months. But it only took a few seconds after I woke up for the memories of the night before to come flooding back to me, and I nearly freaked out.

Getting fucked by a stranger in the bathroom of a gay bar was one thing. But having to make that walk of shame, nude except for the chastity cage on my cock, and present myself to my friends was something else.

Truth be told, they all thought it was hilarious, and they mostly treated me to some good-natured ribbing. But after the laughter stopped, the intensity in my friend James' eyes as he watched me get dressed was something else. "Welcome to our team," he said quietly, as if he was going to follow that up with something else. But otherwise, he was silent, for now.

They insisted on buying me a round, so I actually hung out with them for a little longer, but after that I had made my excuses and headed home. Maybe it was just the afterglow of being properly fucked, but I quickly fell into that deep and contented sleep.

As I remembered more details of the night before, I made a sudden move to grab my phone, and I opened the photo gallery. And there were the pictures that the guy who had fucked me had taken with my phone: I was nude, bent over a toilet in the gay bar's bathroom, and quite obviously freshly fucked, with slick lube smeared around the bottom of my buttocks. In one of the pictures I was twisting around and looking back the camera. The expression on my face was... oblivious somehow. And totally satisfied. It was the face of a guy who was craving more cock.

bzt bzt bzt

As that thought bounced around my skull, the buzzing of my phone brought me to alertness.

"BE HERE IN LESS THAN 30 MINUTES. BRING YOUR LOCKBOX."

A second message had an address. It was for a highrise downtown, a couple blocks from the gay village.

I looked at the clock, and realized I didn't have time for a shower. I did a quick wash-up and brushed my teeth and got dressed. I went to my closet and dug out the realtor's box that had the keys to my chastity device inside. I didn't know the combination: I had sent a picture of it to a website and I was expecting to get it back the week after next. I dropped the lockbox in my backpack and headed out.

One subway trip and a brisk walk later, I was knocking on the door of a twelfth-floor apartment. It was 26 minutes after I had received the text.

The guy who had fucked me the night before opened the door and let me in. He was dressed more casually now, in a plain white t-shirt and a pair of jeans.

"First rule," he said, walking past me. "When you're here, you will always be naked. Get those off and meet me in the living room."

I wasn't sure where this was going to go, but like the previous night, there was just something in his voice. Something I'd never really experienced before... I wanted him to command me, to give me orders. I wanted to follow his orders.

With a bit of a stir in my belly, I quickly got undressed. There was a stool and a shelf-stand in the entryway beside a coat rack, and I made a mostly neat pile of my clothing on the top shelf. My cock, contained in its plastic cage, seemed to be onside with this, and I could feel it pushing out a bit, trying to get hard.

"Bring your lockbox in here with you," the voice said from beyond the entryway. I pulled it out from my backpack and walked into the main part of the apartment.

It was a typical living room. Furniture looking somewhat pricy but lived-in. A giant TV on one wall, flanking large bookshelves. A desk with a computer in the area that was originally meant as the dining room. A couch and armchair set, my keyholder seated in the latter.

"On your knees, bitch. That's the way you should be unless I tell you otherwise."

I awkwardly dropped to my knees.

He held out a hand. "The lockbox."

I shuffled over to him on my knees and handed it over. He shook it once to listen to the keys rattle within, then set it on a table beside him.

"You can send me the combination when you get it from your website. Then I'll decide when you get to unlock. Come here, stand beside me."

I followed his gesture and stood up. He gestured at my arms and I quickly held my hands behind my back. He reached out and lifted my cage, inspecting it and evaluating the tightness of the ring around my balls.

"Well, at least you seem to have a proper sized ring. Cage could be a little shorter. Your balls are okay? No rubbing or chafing?"

I shook my head and said no.

"Well, then, you'll be fine wearing this for a while yet. Back on your knees. Another rule: never ask me when you're going to be unlocked."

I was settling back on my knees beside him. He waited a minute before speaking again. he held up my wallet.

"I know your name, but I don't really care. My name is William Conlan, but you will only refer to me as Sir. Is that understood?"

"Yes Sir," I said.

"The power in this relationship flows in one direction. It's about you obeying and showing respect to me. Is that clear?"

"Yes Sir."

"The pleasure in this relationship also flows in one direction: you will service and pleasure me. Because you're a pussy bottom faggot that will probably turn you on quite a lot, but that's incidental. Decisions about pleasure are for me to make and for you to follow. Are you really willing to set aside the easy pleasure you used to get from playing with your cock?"

I thought about the way it felt when he was fucking me. That was a lot better than playing with my cock. "Yes Sir."

"It takes a little bit of self-discipline to lock yourself up and stay locked, but it's going to take a lot more self-discipline to stay locked for as long as I will keep you that way. Your frustration and horniness counts for nothing."

"Yes Sir."

"I may choose to share you with other men, and it'll be your job to service them like you would me. Will you do that?

My cock stirred in its cage. "Yes sir."

"When you get fucked, it's your job to make sure the man is wearing a condom."

"Yes Sir."

"You will have no privacy any more. I might take pictures of you. Or videos. It's none of your business what I do with them. Are you okay with that?"

I swallowed. I thought this over for maybe ten or twenty seconds. My cock kept twitching. "Yes Sir."

"I also get off on pushing you. Pushing you to do things you wouldn't have considered on your own. I will always be aware of your need for safety, but I will push you. And your job is to obey. No backtalk or hesitation. Think about that for a second."

For what must have been nearly a minute, he stared down into my eyes and held my gaze. I could feel him measuring me, analyzing how far he could push me. How far do I want to be pushed? What does he want to make me do?

He held the lockbox out toward me. "This is your opt-out right now. Your only opt-out. If you're in, you're in all the way."

He was still staring into my eyes, holding my gaze. I could feel my cock straining against my cage. I realized I was as aroused as I could be. Maybe it wasn't a good idea, but I wanted to be in all the way. I wanted to see what this man could do to me.

"So... are you in? Do you want me to be your keyholder?"

"Yes Sir."

He stood up. "Open your fag mouth."

I complied. He unzipped his jeans, and pulled out his cock. I felt a glowing sensation, thinking he was going to seal the deal by letting me suck on his beautiful cock.

Instead, he held it just short of my tongue. The fingers of his other hand touched my forehead, tilting my head back a bit.

And then he pissed in my mouth. I swallowed, trying to keep up without letting any spill on the floor. Instinctively, I knew I didn't want to find out what would happen if I did. I gasped and swallowed and tried to breathe. As the strong taste of it registered, I felt elated. He can use me however he wants.

2.b: the stairwell test

When he was done pissing in my mouth, he tucked his cock back in his jeans and zipped up his fly.

"Now you're going to show me you can push yourself," he said. "Bend over the arm of the chair."

I did so as he walked over to a desk and opened a drawer somewhere behind me. I did not crane my head around to see what he was doing. There was a slight pop of a plastic lid and then his finger, slick with what I assumed was lube, rubbed around my asshole, and then a finger pushed inside me.

Is he going to fuck me? For a second my knees almost buckled in anticipation. But once more, he had other ideas that had nothing to do with what I was eager for. Suddenly, something was pushing against my asshole, and it wasn't his cock.

There was a momentary discomfort as something large opened my hole. Then just as quickly, the sphincter pulled tight and I could feel a new kind of pressure. He had put a buttplug in me.

"Go get your phone."

Dropping to me knees, I shuffle-walked back to the entryway and pulled my phone from my pants pocket, then made my way back to where he was. The pressure of the buttplug against my prostate gave some interesting sensations as my ass moved.

"There are stairwells at each end of the building. East stairwell and west stairwell. Each landing has a sign with the floor number on it: W10, E11 and so on. Take your phone and text me a picture of every sign from every floor. And get back here in twenty minutes. Go!"

I was processing all of that when he barked the last syllable in a way that instinctively started me moving. Still in that awkward knee-shuffle, I made my way back to the entryway. I grabbed my shirt to put it on.

I felt a swat at my ear and I almost fell over with the unexpected pain.

"I didn't say you could get dressed for this," he said.

Oh, shit. He's pushing me now.

It took me a second to regain my equilibrium. Then I reached up and turned the doorknob, pulling the door toward me.

The door closed behind me as I shuffled out of the apartment. Half in a panic, I looked up and down the hallway. There was only an empty corridor stretching out in both directions. And the door of the apartment across the hallway from Sir's right in front of me. If he had a nosy neighbor looking through their peephole they were getting an eyeful right now. I shuffled over to get out of that line of sight. Then I realized there was no reason to be on my knees anymore, so I stood up.

Walking quickly, I headed down the hallway to the closer of the two stairwells. I felt a sense of relief when the heavy door closed behind me. At least this was a bit less exposed.

Still, I was nude in the stairwell of someone else's apartment building. I wasn't expecting that to be part of my week.

Shaking my head to clear it of all distractions, I looked beside the door, and I saw the sign: W12. I had almost forgotten I had my phone in my hand, but I quickly swiped it open and tapped on the camera icon. clik. I took a picture of the sign. I tapped my messages and texted the picture to Sir. At least I have reception in here!

Then I turned and went up the two half-flights to the next floor. The buttplug was both slightly uncomfortable and strangely pleasurable. W14. clik.

This is easy! I just have to...

My thought was cut off by the muffled echoing bang of a door opening. I froze, unsure if it was above or below me. I held still, listening to distant footsteps echoing through the stairwell. It was tougher to decipher what direction it came from than I would have guessed, but after a few seconds that seemed suspended, I felt sure it was someone below me.

Fine, keep moving.

W15. clik. W16. clik. Texting each picture right after I took it.

Up another floor, and I realized I was huffing away as I reached the doorway to the 18th floor. I was a little slower as I made it up the last two floors. I took the picture of W20, then paused, taking a second to think strategically.

This is probably the least likely place anyone would bother using the stairway. Therefore, I should rest here for a minute and get my breath back, even if I'm running against the clock.

That well-reasoned line of thought lead to its own mini-panic attack, however, when I realized I had no idea how long it'd been since I started. It seemed like an adreneline-blasted flash, but it must have been a few minutes.

Still, I forced myself to stay still until my heartbeat slowed a bit. I considered my next move: Now comes the dangerous part... I have to run the length of the hallway to get to the other stairwell so I can work my way down. Just have to hope no one is coming or going. Apartment hallways are almost always empty, I thought to myself. I hardly run into people in the hallway of my building. But still, maybe like... ten percent of the time?

No point in waiting any longer. I turned the knob and pulled the door open enough to look out while shielding myself. The coast was clear, so I dashed out down the hallway, my locked cage bouncing as I jogged along. The faster pace bumped the buttplug against my prostate and there was a moment of an unusual, intense pleasure.

Halfway there... and of course the elevator ding nearly gave me a heart attack just as I was running past it. There was no way I could get to the end of the corridor without someone getting out of the elevator seeing me. Oh shit...

I have to thank my subconscious for dealing with that situation, as the rest of my brain was panicking and turning to mush. Braking quickly enough to almost give my foot carpet burn, my hand shot out and opened the door just past the elevator. Just like in my building, this was the little closet with the trash chute. I pulled it shut as I heard the rattle of the elevator door open.

I stood there frozen, waiting. Okay, now what? How long would it take to get to get to an apartment door? What if it's one of the far ones at the end of the hallway?

I waited for what would seem like enough time to walk down the hallway and unlock a door. I was about to push the door in front of me open when I thought: what if it's a pizza guy?

I looked out in the hallway, one direction, then the other. It was empty. It's too early for pizza, dumbkopf!

Without breathing, I dashed down the rest of the hallway and through the door at the end. My heart was pounding again as I took a picture of E20. Texted that.

At least it's downhill from here.

The next stretch was fairly easy, and it turned out that going down the stairway did something even more intense with the buttplug. I paused for a second in confusion at one landing when I felt something wet on my thigh until I realized it was a smear of precome. And it wasn't until I was down to the sixth floor that I heard the thump of a door opening again. This one was definitely below me, so now I had to wait to see how far they were coming up the stairs. The distant footsteps went to the second or third floor, then the thump of another door as they exited the stairwell.

By the time I was down to the third floor I was getting nervous... this was the most dangerous zone. But I got the pictures for E3 and E2 fine. But then, I had to deal with the ground floor. The stairwell here was different - instead of two half flights, there was one long flight down to the ground floor... and peeking around to look down it, I could see daylight at the bottom, as there was a side door there to the outside.

As I was thinking about that, the door opened, and an older woman with a small dog on a leash came through. I pulled my head back, but I could hear that they were walking away from the door, and not taking the stairs.

There was the rattle of a metal leash tightening. "Chipsie, come on! What do you think you smell now?" The woman asked, her words echoing past me. What indeed? I thought frantically to myself, crouching naked in the stairwell a floor above the dog.

I waited for long enough for them to walk to the elevator. Then I peeked around again. I took a couple steps down and twisted to try and see through the window on the door to outside. In the direction I could see, there was no one approaching. Down to the bottom of the stairwell, now naked in front of the door. Over by the door to the hallway was a sight that brought me relief: a sign reading E1. I snapped the picture, then looked down the main floor hallway. I think I can hedge my bets here.

No use running down there and past the elevators with people from the whole building getting off. Er, unloading. Maybe they're not getting off because they don't see enough naked people. I was getting a little light-headed by this point. But I was bright enough to go back towards the door to the outside and then back up the stairway I just came down. A car rolled by as I was passing in front of the door.

They probably wouldn't have seen me. Nothing I could do about it anyway. So I climbed back up to E2. I peeked through the door. This hallway was likely to be less busy than the one on the first floor. I opened the door and jogged the length of the hallway. Now I was back in the west stairwell.

I still had to repeat the anxious process of going to the main floor and past the door to the outside, but the coast was clear this time, though I saw someone entering from the main front lobby and walking to the elevators as I took my picture. Then up to W2. Whoops! I was so nervous I forgot to text those, so I sent off the last few.

Then up towards W3. As I turned to climb up the half-flight of stairs facing the third floor landing, the door started to open. Shit!

I turned and almost fell down the other half-flight going down to the second floor. If that person was aware of their surroundings (and not, say, checking their phone) they almost certainly would have got a flash of my bare ass retreating.

Without time to look, I heaved open the second floor door and was back in the hallway, now running back in the opposite direction from where I just came. The hallway was empty, and soon I was back in the east stairwell. I had to pause for a minute to catch my breath and calm down, moving only when someone came in from the outside door below me.

I went back up a flight, and was about to cross the third floor hallway, but thought to myself, what if that person thought something weird was going on and went back to their apartment? I don't want to run into them!

So I went up one more floor, and after a peek out, crossed back to the west stairwell in the fourth floor hallway. How many of these hallways have I streaked through now? I think I've lost count.

Safely back in the west stairwell, I had to backtrack to get my picture of W3. Then I nearly panicked and wondered if I'd missed any in all this running back and forth. No time to worry about it, just go.

Working my way back up to the 12th floor was relatively uneventful, but I felt exhausted by the time I made it there, looking at the W12 sign that was the first one I took a picture of. I made it!

Well, almost. One more dash down the hallway and I was back at Sir's door. I wasn't sure if I should go right in or not, so I knocked at the door. Then I remembered to drop down to my knees. Sir took his sweet time answering the door... I counted 57 steamboats in my head and was terrified he might have gone out. Or what if he was just fucking with me and decided to not answer the door? What would I do then? My mind was starting to spin out of control when he opened the door. I almost fell into his apartment as relief flooded into me.

"It was properly respectful of you to knock. But from now on, seeing as you will be coming here when you are ordered to, you'll find the door unlocked when you get here. Just come in, get naked and present yourself to me."