How I Found a Keyholder Ch. 02

He moved into the living room and I followed behind him. He looked at his phone. "You took twenty-five minutes. That means you have a five minute penalty."

"Yes sir."

He motioned to the side of an armchair again. "Bend over that." I shuffled over and complied.

There was a moment of discomfort as he reached down and wrenched the buttplug out, making no effort to go slowly.

"Your penalty will be ten spanks on your ass for every minute you were over. You will count them aloud. If you miss counting one, I will have to start over."

He started spanking me. I winced but called out, "One!"

I wasn't used to getting spanked, so I didn't have a scale to really know how rough he was being with me. It hurt, but more of a sting than momentary pain. Though once he was past thirty the blows became harder, and it was a struggle to call each one out before the next came.

But then it was done. He motioned for me to move away and sat down in his chair.

"So, Wednesday is your day off?"

"Yes, Sir."

"You will come here every Wednesday for inspection, and to service me if I desire it. If you haven't heard from me, always text me to make sure that the timing is convenient for me. Got it?"

"Yes Sir."

"You may, of course, be required to service me at other times. You will send me your work schedule. Any other time that you are not available will have to be approved by me. Understood?"

"Yes Sir."

"Fine. I'm done with you. Unless I get in touch with you, I'll see you next week."

I started to shuffle away from him, then he looked like he remembered something and added, "Wash the buttplug before you go. You can leave it on the back of the toilet."

I was full of strange sensations, nervous and excited all at once. And also a sort of sense of accomplishment, like I had just done well at a job interview. I wondered to myself how far he was going to push me, how far I was going to go.

2.c: The 30-minute blowjob

I liked my job, but the hours sucked.

It was an office job, but it wasn't nine-to-five. Most people started yawning when I told them my work involved testing databases, but there was a variety of tasks and it involved a lot of problem-solving. The lousy part was that someone had to run tests on the system outside regular business hours, which is how I ended up working weekends all the time, hours shifting around depending on tech needs since I was at the bottom of the ladder. In theory it was only supposed to be for a short while until I could move up into a better spot on the org chart, but everyone above me had been clinging to their jobs, so I'd been stuck in this limbo for eighteen months now. It was getting frustrating, especially these days on Sundays, when I had to be in the office at seven a.m. to analyze tests that had been running overnight.

At least I generally was done by the early afternoon. As I was wrapping up for the day, my phone buzzed. It was a text message from Sir.

"GET OVER HERE WHEN YOU ARE DONE WORK."

That was both a little frustrating - I was dead tired! - and very exciting. This wasn't inspection day, so I assumed that meant he required me to service him. My cock twitched in its plastic cage at the thought.

Following his instructions, when I got to his apartment, I went right in without knocking. On top of the stool in the entryway there was a note that said "BRING YOUR PHONE" as well as the same glass buttplug that Sir had inserted in me the last time I was here. Its presence implied I should be wearing it, but there was no lube to make that easier. I wondered if I could go to the restroom and get some, but the fact it was here implied I should be putting it in here.

Lesson learned: from now on, I guess I had to keep some lube with me at all times, along with those condoms Sir told me I would require men to wear when they fucked me. I thought about that as I undressed, then I squatted and licked the buttplug, trying to spread as much spit as possible over its surface. I did the same with a finger and ran it over the surface of my asshole. The buttplug went in like that without too much resistance, but I supposed I shouldn't assume anything bigger would go in that easy.

With that completed, I pulled my phone from my pants pocket and shuffled on my knees to the living room. Sir was sitting at his desk in front of his computer, and gestured me over when he saw me enter.

He had a serious tech set-up, with two large monitors side-by-side. The "desk" was, in fact, more of a table with open sides, which meant that I could see he was naked from the waist down as he sat in a fancy ergonomic chair.

"You're going to need to get better at sucking cock," he said, dispensing with greetings or any small talk. "The number one thing you have to learn is to keep your mouth tight and to keep suction on the cock."

"Yes Sir. I'm looking forward to practicing, and getting better."

"Well, your job today is to suck me, and you better learn quickly what works and what doesn't. I'm not in any hurry today, so I want you to suck my cock for at least half an hour. If you make me come too fast, you'll be punished. But if I lose my hard-on, that will be even worse for you. Got that?"

"Yes Sir."

"Get under the table and suck my dick, faggot. Oh, and, give me that," he said, gesturing at my phone. He took it from me and swiped at the screen. "What's your entry code?"

I hesitated for just half a second, long enough to get a look but no further chastisement. It felt like an invasion of my privacy to give him the code to my phone, but then I realized I had agreed to give up my privacy to him. Plus, at this point, I didn't want anything to stop me from being able to suck his cock. So, I blurted out my passcode, and crawled under the desk.

As I did, he shifted forward in his chair and spread his legs. In the enclosed space, a bit of a musky smell wafted toward me and I felt something like hunger. Cock-hunger, I guess.

His limp dick dangled between his legs and I wanted nothing more than to reach out and touch it, to explore and play with it. But I remembered his injunction from the first night to use my mouth only and I assumed that unless I hear otherwise, that's the way to proceed. But with the table above me, at least I'd be able to focus on what was in front of me instead of having to worry about maintaining eye contact. Above me, I heard what sounded like the audio to a porn video, so I guess my mouth wasn't going to be the only stimulation he was receiving.

In place between his legs, I leaned in to sniff his crotch. The fragrance was inviting me to do more, so I leaned in and began licking, hoping that this much exploring was at least okay. He said he wasn't in a rush, right? With my nose, I flipped his flesh tube back and forth so I could push my tongue toward the base of his thighs. Then I pulled back a bit and slowly licked his balls as thoroughly as possible.

It seemed like his cock had grown a bit, so I gave it long tongue-strokes from the base to the tip, twisting my head to do the sides of the shaft as well. Then, pinning it against his thigh, I let my tongue explore his foreskin.

All of this I would be happy to keep doing... I wanted to know everything about this cock, every detail. But I remembered that this was not about what I wanted. I was here to please this man. So I stretched my lips over my teeth and guided his cock into my mouth.

Mmmmmm. There was a different sort of slickness as my tongue touched his piss-slit, and I swallowed, trying to taste his pre-come. There was a bit of a salty undertone, and I wanted to taste so much more of him, so I went down deeper, deeper, seeing how much I could take in and putting to use all the practice blowjobs I had given to my dildos. I felt his cock touch the constrained spot at the back of my mouth, then slip through as my lips and nose touched his belly. I felt his body hunch forward a little more. I had deep-throated him, though he was still maybe only three-quarters hard. And hurriedly, I started to pull back before I started to gag on it.

Klonk!

Metaphorical stars and birdies danced around my noggin as I bashed the back of my skull against the underside of the desktop. I'd have to remain very aware of the limited space that I was working in... and I realized now that he had been waiting for me to commit to taking his cock in my mouth before he slid further forward in his chair, giving me a lot less room to back off. The message was clear: keep your mouth on that cock.

Well, then. I set to work. It was like driving with a standard transmission for the first time... there were six things to keep track of all at once, and half the things I was supposed to be doing (like keeping my mouth tight for constant suction) seemed to make the other half (like breathing) impossible. And of course, besides all that was the low-key pleasure coursing through my body: the feelings of my cock occasionally straining against the cage plus occasional unexpected jolts from the buttplug. I wanted to focus on those wonderful feelings, but I had to keep trying to ignore them to focus on the task at hand.

The next unmeasureable stretch of time was trying to navigate all that, breathing and sucking... adding more intensity and then backing off just a little. His cock had gotten fully hard and I did my best to keep it that way, wondering how I would be able to tell if I was pushing things too far and if I would be able to keep him from eruption without backing off too much.

My mouth was getting a little sore from using muscles I didn't normally use this way, but there was no option for a rest stop. I just kept sucking, trying to add some variations with my tongue. But not too many variations. I thought about jerking off (a skill I had long mastered, although I guess now I would be getting out of practice) and how when you're having a good wank you don't worry about "mixing it up", you find the stroke that's in the right spot and you keep doing it. So I kept going, sucking his cock.

At some point, a movement in my peripheral vision caught my attention, and I twisted my head a bit to see. Out of the corner of my eye I could see it was my phone, held below the tabletop, lens pointing at me. Well, I guess I'll have some footage now of me sucking a cock.

That gave me cause to think about what that meant now that he had possibly been going through my phone for however long now. For the past week or more, since I had gotten really bottled up and horny while in chastity, I had been obsessively taking pictures of my locked cock and body, so he had probably found all of those. But there were also all my contacts, all my messages...

That line of thought was cut off as I felt his cock twitch underneath me. I almost panicked as I definitely didn't want to make him come yet. I opened my mouth as wide as possible and twisted my head as much as I could to switch to working my tongue on the less-sensitive side of his shaft. I kept that up for awhile, and his edge seemed to pass, and fortunately his cock seemed to be as hard as it had been before. I switched back to straight-on sucking, but took more care to ease off like that a few more times.

And I kept these variations up for as long as I could. I had no sense of time while doing this at all... I wasn't sure if ten minutes had passed or forty. But the twitching in his cock was getting stronger now, and it seemed like I wouldn't be able to put off the inevitable for much longer now. And I realized that despite the ache in my jaw, I was aching even more for his come. Plus, I wanted to give him the best orgasm I could... I wanted him to feel like it was worth his time to let me worship his cock like this.

I took as deep a breath as I could through my nose and once more tried to deepthroat him. I again felt that bump and that tightness before his cockhead entered my throat. I managed to hold there for a few seconds, my tongue poking out against the base of his ballsack, before I needed to pull back. Once again, I had gotten away with it without retching, but I guess I would have to learn to suppress my gag reflex much better than that.

And then one more stretch of bobbing my head up and down on his cock before I felt his thighs tighten and his cock twitch. He started ejaculating in my mouth. Once more I had too many things to do, and the one that I wanted to be doing the most - savoring the taste of his come - was the one that had to be shifted to the bottom of the list. I had to breathe, and keep sucking to let his orgasm finish, and swallow before I started choking in his jism. Again, it was impossible to measure, but it felt like he spurted many times and deposited a lot of semen in my mouth.

Not wanting to over-stimulate him as his orgasm faded, I eased back to a gentle suckling as I could feel his erection wilting in my mouth. Quickly, it had shrunk enough that I could finally remove his cock from my mouth and I carefully licked it clean, before stopping and moving back from his cock.

After thirty seconds or so, he shifted back in his chair, and a short while after that he said, "All right faggot, you made me come. You can come out from under there." His hand appeared between his legs, tossing a piece of paper towel toward me. "You better wipe up anything that dribbled out of your useless cock. Don't ever leave my floor in a mess."

There was indeed a small pool of my precome on the floor. I carefully wiped it up and then, my knees aching, I shuffled out from under his desk until I was on my knees beside him, wadded up paper towel in one fist. He was focused on his computer monitor and it was a minute or so before he turned his attention to me.

"Well, that was almost acceptable. You managed to suck me for twenty-eight minutes. But your mouth was only really tight for about half of that. You need to keep that suction. I assume you have a dildo you use on yourself?"

"Yes Sir."

"Well, until you can get it right and last a decent length of time, you will give it a half-hour blowjob like that every day. Understood?"

"Yes Sir."

"And there will be a penalty for missing the target by two minutes. That's ten spanks per minute, so I owe you twenty spanks. I'm busy today, so you better remind me to spank you when you come for your next inspection.

"Yes Sir."

"You may go. Clean that buttplug and leave it in the bathroom again."

"Yes Sir. Thank you very much, Sir."

2.d: The Inspection

On Wednesday, I returned to Sir's apartment for my weekly inspection, letting myself in the unlocked front door of his apartment. I got undressed, leaving my clothes in a pile on the stand by the door, laying out my socks, then my pants, and finally my shirt on top. Once again the glass buttplug was sitting on the stool. I was ready for it this time, and I opened the small carry bag I had with me and pulled out a tube of lube, applying some to the plug and my hole, making the plug slide in fairly easily.

There was one new variation this time, however: a pair of lined leather cuffs. I had seen these in videos before and knew that they were for my wrists. I put them on one at a time, checking that they were tight enough that they couldn't slide off over my hand, but not tight enough to feel uncomfortable. Thus prepared, I shuffled into the living room to find sir at his desk once again.

"Ah, a piece of meat... here to be inspected."

"Yes, Sir."

He gave me a look of slightly-exaggerated seriousness. "Well, then, we better do this properly." He stood up and walked over to the doorway separating the living/dining area from the kitchen, beckoning for me to follow.

"Wrists out." There was a table just through the doorway, and as I extended my arms out in front of me, he reached over and grabbed something. It was a short, thin metal chain, almost like a dog's choke-chain. He reached down and clicked the metal ring at one end of the chain through the clasp on my left wrist.

"Stand up." I pulled myself up from my knees - and already it felt strange to be standing in the presence of my Master. But any thoughts I had that this might put us on a more equal footing soon vanished.

There was a metal step-stool just inside the doorway- the sort of thing you might keep in your kitchen to reach up to a high cupboard - and he stepped up onto it. Holding onto the loose end of the chain, he reached up, and I instinctively extended my arm to follow him. As I looked up, I saw him run the free end of the chain through a metal ring that was embedded in the top of the doorframe. He pulled it through, and understanding what he was doing, I raised my right arm so he could attach the other end of the chain to my right wrist. So now my hands were on each side of the top of the doorframe, secured to the metal ring.

He stepped down off the step and I had a moment to evaluate. The top of the doorframe was just high enough that I was raised up a bit onto the balls of my feet, though not on my tip-toes. And although the chain wasn't locked to the wrist-cuffs, it would be fairly difficult for me to reach under the top of the door frame to try and undo the clasps. I hoped I wouldn't have to find out how difficult.

So there I was - like a side of beef, hanging up and ready for inspection. For what seemed like the first time, my Master took what appeared to be an interest in my body, running his hands down my back and my buttocks, and then up the front of my thighs, my belly and my chest.

It felt nice to be touched, even in these circumstances. As his hand ran back down and touched my caged cock, I could feel some pre-come oozing out. His left thumb and forefinger reached down and encircled by balls.

"Oh, you like this, don't you?"

"Yes Sir!"

"Well, just remember, it's not my mandate to be all gentle with you." With that, his right forefinger flicked lightly at my exposed balls, sending a jolt of discomfort through me. He laughed as I winced, then flicked my balls a little harder. It hurt more, but being ready for it I managed not to jerk my body as much.

"So, you're here for me to play with." With his right hand still squeezing and tugging at my balls, the left hand darted behind me and slapped at my buttocks from underneath. "What if I want to play rough?"

I knew I had no choice in the matter at this point, and anyway, I wanted him to know that I was willing to do what was required to please him. "Whatever you prefer, Sir!"

He spanked my ass a couple more times, them his hand released my balls. He reached up and ran his finger over my nipples, suddenly pinching them hard. I had to contain a yelp.

"Well, that seemed to do something," he observed. "Let's see if your nipples are sensitive."

He reached again into the kitchen and grabbed something else, and a moment later I felt an intense sensation as he attached a butterfly clip to one nipple, and then the other. This was something I had never experienced before, and it took a few seconds for me to process what I was feeling. It was stinging, but not so much with pain as with an overpowering level of sensation. It felt like my brain was overloading... and then he tugged gently at the chain connecting the clips and another level of that stinging washed out my brain. I wanted them taken off right away... not so much because they hurt as that the white noise in my skull was somewhat overwhelming.

But it wasn't my choice to take them off. My master disappeared into the kitchen for a moment, and I had a few seconds to take a breath and catch my bearings. The sensation in my nipples was still extremely intense, but I could tamp it down a little now, and I turned my head to look as I saw him walking back toward me, with something in his hand.

It turned out to be a fairly long dildo with a suction cup on the end. He attached it to the doorframe behind me, the squeezed some lube on it. Then he reached down and pried the buttplug out of my ass.