I Made the Mistae of Meeting Him

--This is more of a very broad prelude of the main story. I tried to add in whatever was needed while at the same time keeping it somewhat short. If you're in the mood for something that's vivid right now then this probably isn't the story for you. My next submission will be though. I promise I'll try my best to get the next chapter in rather quickly so please watch for it.--

These things didn't necessarily start at any one particular place or time. Well, I could probably narrow it down to the place. The computer. My never ending supplier of porn. I got around to the internet when I was about 15. Went looking for as much free porn as I could find. To this day that's what I do. Only somewhere along the way I grew a... a tolerance? The more typical and bland side of porn didn't do much for me. I started looking for things a little less common. Anything extreme really. Bondage, beastiality, bukkake, bathroom, femdom, gay, (In about that order) plus anything unusual I could find along the way.

Somewhere in all the mix of things I stumbled upon Adult Chat in Yahoo. Now don't get me wrong, I wasn't oblivious to it, but it'd just never sparked my interest when I was in it the other times. Then again, those other times I never bothered to go into 'Gay Male'. So I found my new 'thing'. Turn on my web cam, take off my clothes, and take care of business taking requests from other people in the chatroom along the way. I wasn't in the Yahoo rooms for very long, I quickly moved to the User rooms. It took me a while of browsing around to figure out which rooms fit me best. I ended up hanging around in "Older for Younger", "Slaves 4 Masters 2 Use", and I'd go into a couple other rooms on occasion. Normally I'd turn on my Web Cam until some random guy messaged me. First I'd check his profile hoping to figure out how old he was(I didn't like the idea of doing things with a guy near my age, I tried to keep it 35 and up) then I'd go through the typical talk that they liked to have until he'd finally start saying what he wanted me to do, and I'd do my best to please him. Take on the submissive role in other words.

This kept up for several months, but because of how often I'd get online and go into any of these chat rooms(Maybe once or twice a week), I hadn't made a single acquaintance. I had several people on my Friend List, but I didn't say a single word to them. I'd always get online and go into the rooms with a clean slate. This is how I first got into anal play. For some reason or another I didn't really take it very far. Fingers, small objects, and on two or three occasions, I'd wait till no one was in the house and go find my mom's dildo. Rather thin piece of rubber that was no more than six inches long. considering I'd only get around to doing these things maybe once a month, each time I started in I was tight as hell. Especially when I would use the dildo. Always had to endure a bit of pain for that.

It wasn't until my parents were out of town and I didn't have much to do that I met a guy in the "Slaves 4 Masters 2 Use" room that I talked to more than one time. I didn't have much to do so I spent a good 3 or 4 days in front of the computer. Several hours of which were with him, Red. He was 51, lived in the same city I lived in, he fit the profile of a rather perfect Online Master. He was a semi-big guy(his body), hairy, kind of an ugly looking guy. Exactly what I was looking for. One of my biggest turn-offs when I was browsing through my Master's profile was when I'd come across a picture of him that made him look 'nice'. I wanted a somewhat nasty and burly looking older man that wanted a submissive boy. Of course I won't leave out his 'size'. I know this doesn't seem big compared to most of the stories I've read here in Literotica, but to me, he had a massive 7 and a half inch cock. I don't know what the circumference was, but I'd describe it as wide as hell. That was the most intimidating part about it.

So he talked about meeting up for real and I did my unusual thing. Shitty as it is, I'd simply go along with it, sound excited about meeting him, talk about it with him all he cared to do and just make sure not to go into details. Always delay the details. Details meaning.. My phone number, my address, my 'real' name (I always used my fake name - Matt), things like that. So I got through a few minutes of talking with him the first time he Instant Messaged me, while at the same time stroking, and then I turned on the cam for him where he saw me already nude. Me.. I'll be honest, I don't have a body of steel. I'm 6'1, about 165, (Very very skinny). Now I know a lot of guys like that though, but I had another things working against me. I was very hairy. Hair on arms, chest, legs, crotch, butt, everywhere almost. I'd never really had a problem with shaving or anything, just never had any real motivation to do so. I'm pretty satisfied with my dick. Six inches even with an ok width. So it was standing at full attention with my hand wrapped around it showing it off to my new temporary Master.

I'd explained to him my short history in front of the cam so he'd already come up with what he wanted me to do for him. It mostly consisted of my ass being played with using my finger, then onto my mother's toy for nearly two hours. It seemed to have gone on forever. Never in my life had I paid so much attention to that part of my body for so long. It ended in me begging to cum. He'd tossed around the idea of me eating my own cum, which I'd never done before, but in the end he didn't make me do it. He did make it clear that I was going to for him at one point or another. Didn't think much of it at the time. I just got offline and went off to go do something else.

Later that night I got back on and repeated the process for him. My first time to ever get on cam for anyone more than once. This actually kept up for the next few days. I'd grown quite a liking to this Master. Even more so, I'd actually grown to like the idea of pleasing him first, and me when he said it was ok. After my parents got back I only got on cam for him two times in two weeks time, but the second time he provoked a bit of interest in meeting him out of me. It sounded good and all, but the thought of it made me nervous. More nervous than I'd ever been. Especially when he talked me into it. At the time I figured I'd just not talk to him anymore. The next day when I got online I decided to go ahead and meet him. I didn't know if I could actually convince myself to meet up with him when the time came, but I planned on it.