The next week when I went for my appointment with the good doctor I was in a great mood and definitely in the mood to talk. I had gotten used to talking about myself with Dr. Roberts. It was refreshing to finally be able to talk with someone about the things I had on my mind.
As always, Dr. Roberts greeted me warmly. I took my place on the couch I like to sit on and he sat at his desk. "Well, what would you like to tell me about today? On your last visit you were telling me about your first time with a man. We can continue from that point or you can tell me anything you'd like to share." I didn't want to tell him about the next couple of guys that I was with because I wasn't proud of the stories. So I decided to tell him about the boss I had when I was 17 or 18 years old.
"Okay, what is it about your boss that interested you?" I had never thought about what "it" was about him. I just knew he had it. "Well, his name was Ron. He was my manager at Wilson's (which was a big department store). I worked in the sporting good department. When he hired me he was very nice. I really didn't deserve to be hired because I had been fired from my previous job. He told me that he was willing to take a chance on me. I would be Christmas help and if I worked out I could continue on a regular basis. I understood his terms and accepted them happily."
"I worked through the holiday and was twice the best salesman in the department. After the holidays I was kept as a regular employee. That was a different experience because there were not many customers afterward. In addition there was usually just one person working in sporting goods at once.
The guys I worked with during the holidays taught me a bad habit of kicking field goals in the stock room. We'd go back there together and bet who could make the most in a row. They'd also look at Playboy and Penthouse magazines that they left there. Anyway, once I was working alone I was bored to tears.
I went back a few times to kick the ball, but it wasn't fun by myself. One night around 7:00 Ron came around to check to see if everything was okay. He seemed bored too. He said "you wanna kick a few?" I didn't believe he said that. I thought we'd get in trouble if he knew, and now he's asking me to. "Sure" I said. We both walked to the stock room (which was huge and held all our stock, plus furniture department stuff). While we kicked he and I talked. He started praising me on what a good job I was doing. Soon he went to the file cabinet and opened it (that's where the guys kept their porno mags). "What's this? You guys are going to get me in trouble with this shit." I told him that they weren't mine and that we should just throw them away. "Naw, not just yet. Hey you'd better go check the floor." When I went out to the floor there were two old ladies wanting to pay for some housewares stuff. I rang them up and returned to the stockroom. When I got back Ron was standing there with his cock out and playing with it.
I stood back quietly for a moment and adored Ron. He was quite young for my taste (only about 45 years old) but so damn cute. He had an average size build, dark brown hair and a little bit of grey mixed in. He wore glasses and was clean shaven. On this day he was wearing grey slacks and his company issue blue blazer with a red tie. He look delicious! His cock wasn't huge, but it was nice. It was average length (about 6 inches) and on the thick side. He was standing stroking it slowly. He had no idea I was watching and that made it even hotter.
Shortly, I couldn't take it anymore. I said to him "looks like fun." At that he became startled and proceeded to return his cock to his pant. Before he got the zipper pulled up I reached him and groped him. I knew that he might resist, but I wasn't worried of getting fired because of what I'd seen.
He didn't resist, but he did seem scared stiff. I played with his half hard cock through his pants for a minute. I was getting harder doing this. Then I looked him in his eyes and kissed him right on his lips. He kissed me back. The kiss broke slightly when he said "please don't tell anyone about any of this." I promised not to and we continued kissing. I started working his cock back out of his pants. When it was out I dropped to my knees and sucked him. He moaned in delight. He mumbled that his wife wouldn't suck him. I pushed him back onto a sofa and unbuckled his belt and pants. While continuing to blow him I pulled his pants down to his ankles. Then I threw his legs up and began licking his asshole. Doing this made me so hot. I wanted to fuck him right there but I held off. I just darted my tongue in and out of his hot ass. I fingered him a little while eating his ass. I was amazed at how much he enjoyed this. He always seemed like such a straight laced old guy. His moaning grew so intense that I knew that I should stop.
When I stopped licking his sweet ass he ordered me to feed him my dick. I did what he said and pushed it inches from his face. He then sucked me like it was the only thing he wanted in life. When I was as hard as I could possibly get he asked me for one more thing. "FUCK ME" he said in a deep voice.
I had no problem with this. I wanted it so bad! I got off the couch and positioned myself behind his hot saliva dripping asshole. With his pants still hung up on his shoes I again threw his legs up to enter him. At first I had trouble, then after getting proper position I entered slowly. His face showed pain at first so I pulled back. In a second I tried again. This time he was primed and ready. I slipped in nicely. I stroked his ass with my cock slowly. Each time I pushed in I would give him more of my cock. Once he had it all I began banging him. While I fucked him his pockets emptied onto him. First was a bunch of change that clanged when it hit the floor. Then his wallet dropped onto his fuzzy belly. When it landed it opened to a picture of his family. I fucked Ron for at least 10 minutes while looking at his wife and daughters staring at me. I laughed at the irony of it to myself.
Ron moans turned to cries with my cock in him. He was writhing in passion. He didn't want this to end, but I couldn't take much more. I asked where he wanted me to cum. He said "shoot it in my ass. I want to feel you cum!" After a few more thrusts I relived myself in his asshole. The scene ended and we returned to work sweaty and sticky.
The following day I arrived at work at about 3:45 for my 4:00 shift. When I got to the sporting goods department I saw Dennis Bewk. He was the manager of the whole store. Dennis was not a very attractive man, but not quite ugly. He stood about 6'3" tall and a lanky build. He was about 60 years old, bald on top (with the side combed over), and salt and pepper hair on the sides. Anyway, Dennis was talking to Ron. They called me over to their meeting. Ron said we were going to go up to Dennis' office before we started work.
Ron and I followed Dennis to the elevator and then to his office. Once inside Dennis closed the door and locked it. "Well guys, last night the security guys called in sick so I had to monitor the security cameras. Do you have any idea what happened last night?" Ron and I said no. We weren't lying either because there were no cameras in the stock room. Dennis continued "Well, I'll just play last nights taped from camera 17." He popped in the tape and pushed play. When the tape started we realized that we were wrong. There was a camera in the stockroom. Dennis started the tape right where I entered Ron's ass and he was asking for more. Ron's face was filled with horror. I thought he was going to cry. I didn't really care because if they fired me I could get another crappy job anywhere.
"What should I do about this" Dennis asked. We both shrugged our shoulders not knowing what to say. "I could fire you both, or we could work something out." Ron's eyes grew brighter. "What! I'll do anything. This will ruin me if this gets out." Dennis smiled and motioned Ron to come over to him. When Ron got over to Dennis he pushed himself away from his desk. Ron looked down in disbelief. Dennis sat there with his cock out and standing straight up. The damn thing must have been 10 inches long and thick as a beer bottle.
"Well, Ron if you want me to forget about this you're going to suck my dick, then I'm going to fuck the hell out of you, then you are going to suck my cum out of my cock. Is it a deal?" Ron knew he was defeated and had no options.
Ron dropped slowly to his knees and began sucking his boss' huge cock. It was hot hearing Dennis order Ron to do things while I watched. "Take your pants off! Don't stop sucking though! Finger your asshole! Put on some of this lube!" It was almost humorous at how Ron was being abused. "Okay kid (referring to me) get him warmed up." When he spoke to me he seemed softer and gentler with his tone.
Ron opened his legs for me to enter him from behind while he blew Dennis. By this time he seemed to be enjoying his punishment. I poked in easy. He was still a tad loose from the night before, plus he had lube on his ass. I fucked him hard. I also put two fingers in slowly. I wanted to get him ready to get ripped apart by Dennis. "Okay kid that's enough. Now it's my turn! Ron lay on my desk and get those fucking legs up high. "
Ron followed his instructions to a tee. Dennis approached him with his cock in hand. When he was standing up he looked even bigger. I cringed when Ron cried out. He must have been in agony. Dennis didn't go slowly; he didn't let him adjust, he just went for it. The cries lasted for over two minutes. When they subsided, Ron grabbed his dick and began stroking it. He was now at least close to being comfortable (how I don't know). Shortly after Ron got into it Dennis began moaning. He stopped fucking and pulled out. He ordered Ron to get on his knees and jacked off all over his face and in his mouth. "Eat it!" Dennis directed. Talk about hot! Ron gathered the cum from his face and sucked it off his fingers. "Now get dressed and get out of here" Ron thanked Dennis and limped out of the room.
This left just me and Dennis in the office. "Now my boy I have something for you!" I started to mumble about not being able to take it. He started laughing "that's not what I want from you. I want you to screw me like you did on that video footage." I smiled and got hard instantly. For some reason, right at that moment I started to find this less than attractive man interesting. "Okay, I'd be happy to fuck you Dennis. But I first want to suck that monster of your's." He was standing up and I knelt in front of him. His cock was flacid and still over 5 inches long. The took every inch of his soft meat. I kept his cock deep in my mouth as it grew. I felt my throat being pushed on. When I felt it firm up I started bobbing my head on it. Dennis mumbled in a deep sexy voice while I gave him head. I could smell Ron's hot ass in his pubic hair. That got me close to cumming. I stopped instantly because I still had work to do.
Dennis laid back on his desk and lifted his legs. "I've wanted this since you started working here." I smiled as I lowered myself to eat his ass. It was so hot in his ass. When I lubed him with saliva I entered. We both sighed in relief. It felt so great in him. This experience was more than a fuck; it was like we were making love. It was such a terrific experience and I wanted it to last forever. I fucked him slowly for almost an hour. I couldn't believe that I did it that long until I looked at the clock. When I was close he asked me to sit in his chair. He then sat on the floor in front of me and rested his head on my thigh. He sucked my cock like a vacuum without moving his head at all. Our eyes were locked on each others eyes while he serviced me. When I finally came he grew more excited as he swallowed my cum. He also shot cum all over himself. When he finished eating my cum he gathered his own and savored it. The evening ended with us lying on the floor kissing for several minutes before I got dressed and returned to work.
To this day I still screw both of my bosses. And love every minute of it. Its a shame more people don't like the work they do.