CHAPTER 1
Like a lot of guys, I can't pinpoint exactly when it happened, but at some point in my life I started fantasizing about having sex with another man. Maybe it was always there.
As the years went by I enjoyed a varied sex life. My first live in girlfriend really liked to experiment. This was my first experience with anal sex. She seemed to enjoy it once we got going and the tightness was incredible, still I never thought about doing it with a guy. One time when I asked to fuck her ass she told me that it was two way street, and if it wanted to get into her ass, she would have to be allowed to get into mine. I didn't know what she meant by that until she pulled out a strap on dildo she had bought at a local adult store. I wasn't sure that the price was worth it, so I turned her down and settled for fucking her pussy.
The next day, the image of that dildo stayed in my head, and found it nestled in the bottom of her dresser drawer. I stripped down and pulled out a recent copy of Hustler and started imagining what it would be like to be the woman in the picture getting the cock rather than delivering it. I placed the head of the dildo on my virgin asshole and slowly pushed until the head broke through the outer muscle into my ass. I was surprised that it didn't really hurt that much, and after a little bit of slow movement I found it not only pleasing but one of the biggest turnons I have ever had. I shot a load of cum like never before and greedily licked it off my hands while slowing pulling the dildo from my ass.
Even with this, I never thought about replacing the dildo with a guy, and I never did let my girlfriend fuck me with it, either, although I wish now that I had.
My next girlfriend was also an open minded girl concerning sex. One New Year's Eve I had a friend of mine from High School come to town for a visit. That night the three off us drank a little too much and Gloria started flirting with both of us. Bill looked at me and I just shrugged and said, "Let's go for it." She would suck one of us while the other fucked her. At one point she got brave enough to take us both into each hole, which was a thrill in itself and caused me to shoot a powerful load into her ass. (It was the first time I had actually fucked her in the ass and I got the honor because she didn't think she could possible fit Bill's 9-inch cock up there.)
During these two hours of sucking, fucking, resting and fucking some more, I never once came close to touching Bill's massive cock, and really didn't think much about doing so. Wish I knew then what I know now, that's for sure.
As time went by, I got married to a woman who was far from adventurous in the sex department. A few times I was able to sneak my finger into her ass while we were fucking, but that was all. She would suck my cock once in a while, but never to completion. Don't get me wrong, the sex was pretty good, and even great once in a while, just not adventurous.
Because of this, my masturbation time became the adventure time. I didn't buy a dildo, but I did get a large candle and carved it into the shape of a huge cock. I loved plowing that thing into my ass while beating off to my various porn pictures. My wife may have suspected something, but she never let on. Personally, I think she was just relieved that I wasn't coming after her for sex as much as I used to.
It was during this time that the internet started catching on as did on-line porn. I was never one to pay for the stuff, but I found a treasure trove of free material in the use groups. It was here that I found my first creampie pictures, and my first gay porn. I tried telling myself that I wasn't interested, but I still found myself downloading pictures of guys having sex. Still, I never really thought about doing this myself, and seldom came while looking at the gay pictures. I did, however, cum a lot when I looked at the creampie shots and often fantasized about licking the cum out of her pussy and wondering what it would taste like.
If all good things must come to an end, so do some bad things, including my marriage. Ten years was just about all I could take of her and her controlling ways, so I found myself on my own again for the first time in a decade.
Older, wiser but not so eager to tie myself down again, I took the opportunity to look for sexual adventures that I could not have while I was married. I found myself in the Internet Personals looking for available women in my area. The search didn't take long and soon I was enjoying some good sex with two different women in two different towns with no strings attached. It was during this time that I noticed that men also advertised themselves on the site seeking other men. "What the hell is that about," I wondered, and that is when the door finally opened and my years of wondering and fantasizing came together with the reality that I would love to find out what it would be like to have a real cock in my ass, to suck a cock for real and taste another man's cream. The awakening was about to begin.
CHAPTER 2
One thing I always strived for in many of my masturbation sessions was to re-create reality. For instance, I looked for things I could use that would more closely simulate a pussy, and found while the fake pussies at the adult book stores were close, they were sadly lacking. I purchased several different dildos hoping to get the real feel of a cock in my ass. The most bizarre thing I would do, though, was to re-create having a cock come in my mouth. To do this I would jack off and collect the cum in a small cup. I would then suck the cum into a small plastic syringe we had for giving medicine to the kids when they were babies. I bored out the center of a short, cock sized candle and fit the syringe into the candle. An hour or so later, I would start getting horny enough again to start jacking off, at which time I would start sucking my cum filled dildo, and at the right time I let it shoot off into my mouth. How realistic was this, I wouldn't know until much later, but it satisfied my cravings at the time.
With all of this activity, it wasn't long before I started looking at the men searching for men section of the personals. Soon, I got brave enough to post an ad myself, just to see what would happen. Soon some responses starting coming in, and then it hit me. Am I really going to go through with this? I mean, I had fantasized about it, but to actually do this was something else all together. I answered back to some of the replies, but nothing really happened. It was probably as much my fault because I wasn't sure I wanted it to happen. I mean, I did, but I was scared to death as well and just could imagine myself doing something like this.
I haven't really described myself through all this because there isn't that much to describe. I'm not ugly by any means, but I'm not the kind of guy that will end up on the cover of a magazine either. Through the years I have picked up too much extra weight and have less and less time available to work it off. Cock wise, I'm incredibly average. About six inches long and average girth. I have a nice head, I think, but again nothing to write home about. When I come, it doesn't shoot across the room, but rather dribbles out across my hand, and I don't cum in buckets, but barely enough to fill that syringe I told you about earlier. I considered myself a man's man interested in manly things like sports and cars and never acted anything close to gay. So you can see why I might have fantasized about it, but could never imagine myself doing anything about the fantasies.
But then came Steve. Steve answered my ad with just about every right word there could be. First of all, he was married and was an out of town consultant for a local company. That was good because I am fairly well know in this little town I'm in and didn't want to take the chance of having a fling with a local guy only to have it broadcast around town that I was a closet gay.
Steve happened to be in town that week and wrote to me that if I was interested I could come to his room at one of the local hotels that night. I looked at the room number for several minutes wondering if I would actually take him up on his offer or get cold feet. I tried imagining what it was going to be like, knocking on the hotel door, having him answer and then what? That's what was always the hard part for me to imagine, what would that first face to face meeting be like?
That evening, I decided, I was going to find out. I had fantasized about this long enough. It was time to answer the challenge and find out if all of my dreams were true.
