My Mature Boss
submitted January 9, 2005
It was December 19th, and our company was having its annual Christmas party at 8 pm. We were getting out of work around 4:30, so we had a few hours before. However, the party was near our headquarters, which were about 30 miles north. Most everyone had made arrangements to get there. I hadn't, so I decided to take that train. As I was about to leave, my boss asked how I was getting there. When I told him I was travelling by train, he said he could give me a ride, as he was driving up there alone. The only thing was, he needed to stop by his house first. He would only be a few minutes. I agreed, and we left the office together.
Now, I had always been VERY attracted to him. He was 52 years old, balding blond hair and clean shaven--in other words, very executive looking. And there was nothing sexier than seeing him in a suit, but without his jacket. He had an ass that you would kill to look at! Despite that, I certainly wasn't about to do anything with anybody at work.
As we left the office, it was just starting to sleet, so traffic was quite slow. When we got to his house, he invited me in, as he figured it would be 30 minutes before be would come out. We went inside, and he told me to make myself comfortable, while he tended to some business.
About 20 minute later, he told me he was going to take a shower, and would be ready. As I heard the shower running, I couldn't help but fantasize about him in there. After a few minutes, I gathered the courage to go toward the bathroom, to see if I could "sneak a peak".
Just as I got near the door, I heard the water shutting down, so I quickly made my way back to the living room. I heard him come out and, and, after a few seconds, to my surprise, he called me. He was no longer in the bathroom, but rather, in his bedroom, it a towel, with his fresh clothes waiting on a chair. Seeing his hairy chest and NOTHING but a towel covering him made me feel like my throat was very dry, and I felt I could barely talk, I was so excited.
When I walked in, he asked if I would mind rubbing some moisturizer on his back, because his skin was dry, and he couldn't reach it. I THOUGHT I WAS GOING TO EXPLODE! Was he serious? I didn't respond at all, so he asked me, "You don't mind, do you?"
Well, I decided to see how much guts I could gather, and started rubbing the lotion between his shoulders. Slowly, I worked my way lower. All of a sudden, his towel dropped. I found myself with that beautiful ass that I had fantasized about so many times right in front of me, my fingers just a couple of inches from it. I asked him how low on his back he wanted me to go (I don't know if he noticed, but my voice was trembling!).
I slowly worked my hands to the top of his cheeks. As he said nothing, I started caressing down. I now had his ass in my hands. This gave me more confidence, and I worked past his ass, and to his thighs. I slowly massaged him all the way to his ankles, and then slowly worked my way back up.
His legs were now further apart than they were when I started. When I got to his upper thigh, I "accidentally" went up too high, and made slight contact with his balls. I didn’t get any negative reaction, so I did it a couple of more times.
I finally reached very carefully for his dick, and made slight contact. As soon as I did that, he turned around immediately. His fully erect cock was in my face, dripping pre cum. Now, I didn't hesitate for a minute. I just opened my mouth and took in all of him. He slowly lay on the bed, and I followed with my head buried in his crotch. This was intense!!!
All of a sudden, he told me to take off my clothes. I was naked in two seconds. He told me to lie on my belly on the bed. He then took some of the moisturizer, and started at my shoulders. When he got to my ass, he made sure to put some extra cream on his hands. All of a sudden, I felt his ginger probing my ass!
This was now my ultimate fantasy come true. Suddenly, he stood up. I didn’t know what was going on, until I saw him reach into his night table, and pull out a condom. Here I was, on my boss' bed, on my belly, with my ass greased up, and watching him put a condom on his dick. Somebody pinch me!
He walked back to the foot of the bed, and, after climbing on; I felt the head of his cock, slowly but firmly, pushing inside me. It was hurting, but at the same time, it was so enjoyable. When he was finally all in, he started the most rhythmic fuck I have ever had!! Who would have thought this older man could do it so well!
Just as I felt his cock swelling, getting ready to cum, he pulled out for a few seconds, only to come back in with one quick, sudden thrust. He repeated this four times, until he finally exploded inside me. His moans were proof of how much he had enjoyed it. As he got up, I turned on to my back, ready to jerk myself off.
I didn’t have a chance, as he immediately buried his face into my crotch and gave me the best blowjob I can remember, using the same technique of stopping just before I was about to cum, giving it a rest for a few seconds, and then going back down.
When I finally came, I felt like gallons were leaving my body. As we lay there, seemingly spent, we looked at the clock. It was only 6:25. He looked and me and asked "Anybody for seconds?"
Needless to say, we got to the party late.