The summer I turned 17 we had a renter staying in our guest room. He was in his early 30's and his girlfriend had kicked him out of their apartment. Robert was rarely ever around at first. He would get off work, come home, take a shower and then leave until 10 or 11 at night and usually would spend the weekend with his girlfriend. After a while he starting talking to me every so often. I always thought he was interesting and pretty cool, we got high together a bunch of times and then we would sit and talk, mostly about sex. He would ask me details about the young ladies I was sleeping with. I would ask him about his girlfriend who had great tits and always wore tops that made them look like they were about to burst out. Then I would go back to my room and jerk off thinking about doing her.
One day when I was home alone I noticed he had left his room open. So knowing he had a stash of porn magazines I went into his room and went through his porno's. He had dozens and dozens, then buried at the bottem was some gay porn, including some videos. I had at this point in my life slept with several girls and 1 older man. The experience with the older man was about a year earlier and was not the best. I was nervous (and a little uncomfortable) but thought about it, and jerked off to the memory of it regularly. I remembered once overhearing his girlfriend make a joke about him getting a blowjob from a guy friend of his. I thought at the time it was just humor. But I started to think maybe not, so I began finding excuses to talk to him, even tried flirting with subtle sexual comments, I tried to be around whenever he came home. But nothing worked. So I started going around in my boxers, or loose shorts with everything hanging out. But he never made a move. So one day I decided to be bold, I took a Polaroid of my erect cock with one of his gay porno's underneath. Then I slid the picture in the stack of magazines.
The following week my Dad was leaving town for ten days on business, it would be just Robert and I at home. I figured now or never. Everyday around 5pm he came home and took a shower, so for the first couple of days I made sure I was getting out of shower right around when he got home. Still nothing. I was about to give up, when I decided to make one more try. He came home from work, I'm wearing a towel, "Oh I'm sorry Robert I didn't realize it was time for you to get home". He said it was okay he would wait, I suggested he go ahead and jump in as I was not in a hurry. He said okay, then I asked him if I could play his full size arcade video game he had while I waited. He said sure and set the game up for me. About ten minutes later he walks into his room dripping wet and completely naked, he starts drying himself off, I let him catch me looking, but he still says nothing.
Then he gets his clothes out and that is when I ask "Robert, could you come over here and watch me play and give me some pointers??" He says, yeah gimme a minute, I told him no, I'm at a spot I always get killed, so please come and tell me what to do right now. So he comes up behind me, still butt naked, and starts pointing and telling me my next move, I keep doing better at the game, and he never leaves, then he starts moving closer and closer to me, I start to feel his really big cock press up against my ass through the towel. I don't say anything, but manage to rub my ass up against him harder and harder, his hands begin to go down my back and sides, resting against my hips. Then he pulls a little and my towel falls off. Again, I say nothing. He then moves closer to me and I can feel him getting harder and harder. I make a quiet comment, about him getting some wood. He say's to me that I'm the one who keeps shaking that "tight little ass" right in front of him. So I said, "Well I am new at this game, I want you to help me... so I know what to do. I really want to learn this game, so I need you to tell me what to do..."
Robert begins to kiss my neck, and asked me if I'm really willing to do what I told, I moaned a strong YES. Then he began to press down on my shoulders, sending me slowly to my knees. He turned me around, holding his cock in his hand, he told me to suck it. So I put a cock into my mouth for the first time, He kept telling me when to go faster, when to go deeper, telling me to swallow it all when he cums, and after several minutes I did my best. He blew this huge load down my throat and I did my best to swallow every drop. As I stopped to catch my breath, he told me to keep going until it was hard again and after a few minutes it was.
He then told me to climb up onto his bed and get down on all fours, I was a little scared, his cock must of been 10 inches long (it was 10 1/2 inches), I was thinking there was no way I could take it. He told me that he would be careful and if it hurt to much he would stop. So he put some lube on his hands and began fingering my asshole, then a few minutes later I felt the head of his cock pressing against me as he began sliding it in. He worked it in deeper and deeper sometimes slowly, sometimes more forcefully, but eventually I felt his balls slap up against me and him put all of his cock inside me. He then began to work my ass, slow at first, then faster, and harder. He pounded my ass for nearly an hour, me screaming for more and him giving it to me, then I felt him tighten up and as he grabbed my hips he blew another big load right up my ass. This went on all night, me doing whatever he wanted, however he wanted. We were alone in that house for another four days and he fucked me in every way possible in my mouth and in my ass the whole time. We continued this arrangement for another two years until I moved out.
Oh yeah, he never even saw the Polaroid, the porn magazines belonged to his ex girlfriends, she found the Polaroid when she took the box of stuff back, but that is another confession altogether.