Two months after I turned eighteen, my father died in a plane crash. He was flying his private jet to his west coast headquarters when the plane went down. He had divorced my mother years before when she became a total slut, and he got full custody of me. She disappeared from our lives, and I was raised by a series of nannies, maids and others who always took good care of me. My father spoiled me in every way, maybe to make up for the fact that he was never there. My room was like a palace. I had all the best gaming equipment, stereo, and a computer system that I had custom built. The old man also had good taste in women, and had married a former model who was only ten years older than me. One thing about my dad though, was that he was pretty possessive and very macho and he kept Jennifer to himself. She and I kept out of each other's way around the house, and after he died I didn't see her until the day we had to go sit in the lawyer's office and hear the will being read. She was definitely torn up by his death and spent days crying in her room at the other end of the house. I didn't see her for days at a time and when I did she was a wreck.
Dad had left an estate of more than $20 million, with so many stipulations the lawyer had made himself a chart. What caught my attention was the way the old man provided for Jennifer while controlling her at the same time. I guess after mom screwed around on him he wasn't going to have it happen again, even if he was dead. Of course they had a prenup agreement, but he had made sure she wasn't going to run off with his money or screw me out of mine. My money, except for five grand a month and future college expenses, was tied up until my twenty-fifth birthday. Jennifer's money on the other hand, had strings and conditions. For one thing, she had to stay in the house and look after me until I turned 21. She could keep or let the house staff go but she was responsible for seeing that I got off to college, etc. etc. For another, if she wanted her share, she was not allowed to re-marry until I left, had to be in the house every night, no overnight guests, and on and on. It looked like she was going to have to either live a nun's life for six years, or get her jollies during the day while I was at school. The final insult was that I could make monthly reports to the lawyer on her behavior, which could influence her share and cut her monthly allowance.
On the way out the door, she said to me," I'll make you a deal, you stick to your business, and let me do mine, and we'll get along just fine."
"If you think I'm not going to report back on you, you guessed wrong, baby. The old man expected you to stick around and earn your money, and if you start screwing around, I'll nail you."
She turned to me, "I took good care of your father. In every way. I loved him more than you'll ever know and you have no idea how much I'm going to miss him."
As she walked to the limo I couldn't help but notice her figure. Her upper body was too covered to see, but she had a great ass, and just watching her walk to the car gave me a hard-on. I guess I missed him too, but he was hardly ever there anyway, and I was a typical self-centered rich-kid teenager.
When I got home, I did what I did most days after school. Went to my room, locked the door, turned on my computer, stripped naked and relaxed into my big desk chair as the screen warmed up. I loved porn. I was a total addict, and if it weren't for my tutors, I probably would have flunked out of school a long time before. I had a fast CD burner, a collection of porno DVD's I could watch on my TV or computer, and every day I collected what I could from the Internet forums and porn sites. I especially loved facial shots-guys coming in girls faces or even better, in their mouths. I had a collection of more than five gigs of nothing but facials and mouth shots. I would jerk my cock for hours watching my favorite shots. Since I wasn't circumcised, I never had the problem of getting lube all over the mouse or keyboard, but when I really wanted to grease up my cock and have at it, I would queue up on of the facials CD's I had burned, pop on my headphones and pour massage oil all over my cock. I let it dribble in and around my foreskin and would pour it on my chest and nipples and try to time my cumshot with one from the movie. The best ones were the ones where the guy would come in her mouth and then she would look in the camera and drool the cum out of her mouth onto her tits, or into another girls mouth. I would stroke my cock with one hand and play with my nipples with the other. After hours of making myself hold off, I would shoot cum up over the top of my head and all over my chest and stomach. On the weekend, sometimes I would spend the whole day locked in my room, watching porn, putting facial after facial together, and torturing myself-not cumming until I couldn't stand it any more. Those days I usually fell asleep in my big chair, and would often wake up and jerk off again, using the cum that was drying on my chest to stroke my cock to another mind-numbing orgasm.