He was one of my first bosses. He promoted me to assistant manager when I was a senior in high school, and while I'd like to think that he promoted me due to my skills, but in hindsight, I think he was more interested in skills he could teach me!
He hit on me relentlessly, and would often give me $50, or $100, for nothing. He kept trying to get me to agree to let him teach me about the other side of the tracks, but I never gave in. I guess I've always wondered, in those late, dark, horney times at night, what would have happened if I had given in. Let's just suppose.....
We were in the suburbs, while he lived, and played in the city. I knew he had other "boys" around, he would "accidentally" bring one around work at odd times, etc. I have no doubt that what would start as one on one encounters would lead to more "additions", and that can get me thinking.....
I guess it would have to start with me- I mean, he had made his intentions VERY clear! I think I would wait until an opportune time, then, "give in", and see where it went. It would have to be a time when we were supposed to be at work, together, and alone, with no chance of interruption....
We'd be doing inventory, I'd wait until there was no chance of Disturbances, and he'd ask me to go off and count something or other. I'd do as I was asked, only, I would return wearing only a pair of tighty whities. I'd be new at this, so after making this first move, he better pick up the slack! "You told me of lots of ways to earn some extra dough, and have fun doin' it, if I'd only be receptive...." He gets up from around his desk, and comes over to me. Before I know it, his hands are all over me, and I mean all over me! "Why don't we test out your potential, and go from there?" he asked, or stated. What was I going to do, stop there? I somehow figured that at that point, I didn't really have a choice, I mean, I'd put it out there, and he was going to use it!
"Wanna start your first lesson?" Again, it was more of a statement than a question. He "assisted" me to my knees in front of him. "Why don't you take Junior out to play, go ahead now, take him out, and treat him like a piece of sweet candy!" The image was helpful, and I quickly undid his pants, helping them to the ground. I then reached up for his underwear, only to find that he wasn't wearing any! I was greeted with the sight of my first cock, small to average, I would later learn. It was only semi hard, and he shoved it towards my face- " Get it going all the way boy!" I let him shove his cock into my mouth, and slowly, gradually he began to face fuck me. There really wasn't much sucking going on, it was more like, open up and take it! I really don't know how long this went on. It was the first time I was experiencing these feelings, so I guess I was caught up in the moment. Any way, soon thereafter, He pulled me up, and shoved me over his desk. He yanked off what was left of my underwear, and had complete access to me. He shoved my legs apart, and as he shoved his cock into me, I remember hearing him saying something like "I've been looking sooo forward to this", honestly, I really didn't care, I was loving the feelings he was creating in me, and going with the flow.
After a bit of that, he really didn't last all that long, he came in my ass, grunting and groaning and such. I guess it ended a bit quicker than I had anticipated. I'd soon learn that I'd entered a world were things were not going to be as I had expected.
He let me up, laughed, and said, "I always hoped you'd come around..." He got dressed, leaving me with nothing. He reached into his walet, and handed me 4 $50's, and said "If you are really up to making some extra dough, come by my place this weekend." He handed me a slip of paper with an address on it and told me to be there around 7 on Friday. I agreed, and headed off to my clothes.
After getting dressed, I returned to the office, and asked if he wanted help with the rest of the work. He told me to take off, rest up, and get ready for some real craziness on Friday!