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Office Boy (True Story)

by inspired_tip

Chapter 1

It was only supposed to be a second job. Just a way to help pay the bills as I struggled through the all-too-usual early-20s days of condiment soup and mayonaise sandwiches. I was 22, overworked and underpaid at my day job, and my new part-time gig as an evening messenger in the downtown area of the nearby large-ish northeast city was going to be a nice boon to my sad financial situation. Little did I know that my new gig was going to pay off in ways I sure as hell never saw coming. 

After about a week on the new job, I pretty much had the routine down. There were a lot of suits working late downtown, more than I would have thought. The downtown areas of most cities are infamously dead after 5 o'clock. But, there are a surprising number of financial types, legal types, all kinds of high rollers burning the midnight oil. I'd pick up packages, pick up dossiers, pick up documents, then drop the same off, from this post office to that courthouse to that firm. The big, fancy law partnership high atop a downtown skyscraper was just another stop on my evening run that night. Big time firm, always representing famous clients and getting in the news. All I had to do was stop at the city courthouse, pick up and drop off a satchel of important-looking legal docs at the fancy-pants firm, and go. Simple. Just another routine run, the last on my schedule that night. Routine. Until I met Tim. 

I entered the lobby of the building about 8 o'clock pm, and as usual after hours, the elevators were closed and you had to "ring up" to get out of the lobby. I rang up, and told the deep male voice that answered that I was with the messenger service. "Hey, I'll be right down," came the friendly-sounding reply. A minute or two later, a bell announced the arrival of the elevator, and a handsome, bearded guy in his mid-40s exited and approached me, warmly extending a hand. "Hi, I'm Tim, " he said. "Hey, I have these documents for you, from the courthouse" I replied. Tim smiled at me and reached for the package. Now, I was a straight guy with a girlfriend, and had never had so much as a "gay thought" in my life,  but something abut Tim's easy-going mannner, his raffish good looks, his fit, muscular body, his after-hours loosened tie...well, I have to admit, looking back on it, that I was already, let's say, curious? "Working late?" I said, I guess looking for a way to extend what should have been a brief encounter in the lobby, although  at the time I would not and could not have understood my motivation.  "Yeah, big case coming up. I work a lot of late nights when we have a big one coming up. Comes with the territory, being a partner here." Big one...coming up...why was I thinking these hot, forbidden thoughts when I heard these words? And a partner. Something about that knd of power, to a young guy starting out, like me, was...electrifying?

I was suddenly noticing Tim's expensive cologne. And his wedding ring. And his...well, I couldn't look at *that*... but...did I notice a bulge in his...oh God, what was I thinking? I was a hetero guy, who had hetero sex with my hetero girlfriend, and here I was wanting to hang out with this guy, and not in a "buddy" manner, either. My hear literally raced whan Tim said "I know you messenger guys are always on the run...but I was about to celebrate finally ending my very long work day with a drink. We have a fully-stocked bar in our suite...but I don't suppose...you might be able to join me?" "Actually, this is my last run of the night. And a drink sounds great," I replied. Oh. man. WHAT was I doing. I knew, in my head,, heart and groin that this was something beyong a normal interaction, even though neither of us had said one word that was in any way inappropriate in contect. But I knew. And I knew that he knew. "Sure!" I said, and the next thing I knew we were on the elevator and on our way up to Tim's office. His firm had the whole floor, and his office had a large outer area and his own conference room. Very impressive. So was the private bar, and the private bathroom. 

We had a few drinks in Tim's office, chatted about this and that, and at one point Tim said something about taking a colleague"to the woodshed." "Do you know what that means?" Tim asked. It's an old-fashioned term referring to discipline. Corporal punishment." Tim laughed, but was looking me carefully in the eye. This led to discussion I couldn't believe I was having. Tim, in a very fatherly manner, explained to me that he enjoyed providing discipline to boys of all ages, and further shocking me, reached deep into a drawer and pulled out a paddle. "Ever been over a man's knee before?" Tim asked. "um...no," I stammered. But I could feel a heat growing in my groin. A heat that had been growing for a while now. A stirring of my cock that I could not deny.

Before I knew it, I was across Tim's knee, being spanked by hand and paddle. It was so humiliating, being prostrate over a man's lap and being spanked! But my erection gave me away. When Tim ordered me to stand up and march - MARCH! down the hall to the conference room, I felt my knees go weak. "Hands interlocked behind your head. Leave your clothes on the floor and march NAKED!"

This was new. This powerful, controlling, dominant voice. The blood rushed to my genitals and I felt my balls growing heavy as I marched down the hall and soon found myself hand and knees atop the enormous oak table. Tim produced a riding crop and smiled wickedly. "They always tell me this hurts a lot," he said. My already burning ass had to take a cropping that left me with burning cheeks on both ends and a now-raging boner. Down off the table! Tim ordered. I complied, weak, humiliated and exhausted but horny as fuck. "I want you back here next week, same day same time. You will bring gym shorts, gym socks sneakers and a tank top, and you will change into them before you enter the lobby. Do you understand me, boy?"

"Yes, sir," I answered, already excited at the thought of being told when and where to be and what to wear. My God, what was happening to me? "Now, before you go, there's the matterof this," Tom said, reaching down and fondling his bulge through his expensive suit pants. You're going to get on your knees and suck my cock. You are going to do this whether you've ever done it before or not. You are going to do this because you want to do it and because I want you to do it.Now, get on your knees!"

Not even believing what I was doing as I was doing it, I sank, still naked, to my knees. What followed was, quite frankly, a blur of carnal extasy. I found myself licking his balls and shaft, eagerly servicing his cock to the best of my then-untrained ability and then, oh God, his balls, so heavy, s close to my face, contracting so strongly...and then the release...a huge load of hot man-milk spurting down my throat! And, oh help me, I was loving it. I had never been so turned on in my life! I was jacking myself off during this, but when Tim had finished unloading down my throat, he told me to take my hands off. "I want you to drive home with my cum in your mouth and your cock hard. When you get home, you are to think about tonight while you get yourself off. And think about this - next time, we turn up the intensity. Prepare for some deep humiliation.

I was rigid the whole way home, practically dived into bed, and wanked off to the hardest, longest, most mind-blowing orgasm I had ever had. For now, anyway.


Part II - New After-Hours Office Boy


Can\'t wait - faggyanna

This was amazing, I can\'t wait to see what part 2 leads to.

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