From: First Time <cbs@hargray.com> Subject: First Time Anal Date: Wed, 25 Sep 1996 16:47:40 -0400 How did I get here? After having hot and satisfying sex with my girlfriends for years, here I was on my hands and knees while a friend I had known for years shoved his cock in and out of my ass. I met an uncle of a girl I dated for some time who was gay and got to be good friends with him. He acted completely straight so I didn't mind being around him and felt comfortable having drinks with my girlfriend and him on occasion. About a year after I met him, I went over to his house one afternoon where my girlfriend was meeting us after work to go to a ballgame. Will offered me a beer when I got there and shortly afterward my girl called to say she had to work late and would be a couple of hours getting there. Will said I was welcome to kick back and wait and while he was getting me another beer, his companion Mike came in. Mike had been with Will since I met him and although they were quite a pair, it was never made obvious in front of me. Mike had a video tape in his hand but he seemed to be trying to hide it. I found out it was a new gay tape he had picked up to watch with Will after they got home from the game. Will kidded me because I said I had never seen one and he talked Mike into putting it on. It started as most porno movies do, very little conversation and then everyone was naked. I saw for the first time a guy going down on a guy and shortly after that one being fucked by the other. Although I've always been open minded and willing to experiment, I was still surprised when I realized I was getting hard. I tried to conceal it but evidently not good enough. I caught Will looking at my swollen crotch and he said, "I see this is getting to you." I guess his niece had told him I liked for her to stick her finger in my ass because his next statement floored me, "You know, if you think a finger feels good you haven't really tried everything have you?" And with that he leaned over and put his hand on my hard-on. I didn't stop him so he asked if I wanted to continue and try a, "Walk on the wild side." I held my breath for minute, knowing I wanted to but not sure I could say it. When I murmured a yes he quickly unzipped my jeans and went down on me. Now I have had a lot of blowjobs in the past but I must admit, Will could give head with the best of them. I'm eight inches long and he could take me completely in his throat until his nose was buried in my pubic hair. He stopped for a minute and eased my jeans the rest of the way off and blew me until I was about to come. He stopped, told me to stay put, and disappeared in the bedroom for a minute. I then realized that Mike was still sitting on the chair watching with a grin on his face and his dick in his hand. I decided if I was going to try this, I wanted to try it all. While Will was gone I walked over to Mike, kneeled in front of him, and wrapped my hand around his pole. When Will came back down the hall he was naked with his dick waving and I noticed it was a little shorter than mine but about the same thickness. I turned back around to face Mike and gasped when I saw that his cock was nearly twice as big around as Will and mine. I tried to take Mike in my mouth but only the head would fit. While I was making my first attempt at cock sucking, I felt Will smearing something greasy on my asshole. I looked around and saw he was also lubricating his shaft and he said he was going to treat me to my first fucking. I was hesitant but I had really gotten off when several girls had fingered me so I decided to give it a try. I turned back to concentrate on Mike and felt Will put his cockhead against my hole. I made myself relax and turned my attention to the thick piece of meat in my face. While I was earnestly trying to get more than the head of Mike's whopper in my mouth, Will was working the tip of his thinner shaft around. Again I reminded myself to relax and I felt him start to enter me. There was a little pain at first and he stopped when he felt me flinch. I quickly told him not to stop and asked that he just keep going slow. As I adjusted to the new feeling of having a cock in my ass, he eased forward again. I could feel my hole stretching to take him but there was no more pain, just a fullness that started to feel good. He kept progressing, moving slowly forward then giving me time to get used to the invasion. After a minute or two he stopped moving and said, "You finally got it all, you ready for your first fuck?" I said yes and he slowly pulled his shaft out for what felt like a yard and then pushed it back in. The feeling was incredible. My ass had not only stretched to take his entire cock, it was eagerly accepting his thrusts. I moaned in acceptance and he picked up the pace a little. My own dick was aching it was so hard. I had never felt anything so intense. I turned my attention back to Mike and started blowing him with renewed energy. After Will had fucked me soundly for what seemed like quite a while, he suddenly pulled his cock out of my ass and leaned back. I looked over my shoulder and asked what was wrong and his answer left me speechless, "Mike wants some of this". I had quickly gotten used to Will's 6 inch dick after never having anything in me bigger than a finger, but Mike was a different situation. His cock was only an inch or so longer than Will's but it was almost twice as thick. I had started into this on a whim and thought I would get away easy on my first attempt at getting ass fucked. I had planned on jacking Mike off while Will was having his way with me and calling it quits. That would have satisfied my curiosity for gay sex and left me with time to think about what happened before trying to step up to something Mike's size. As if to help me make up my mind, Will slipped his shaft back into my ass and gave me several more slow strokes. It worked because I agreed to let Mike try. Because I was apprehensive, I asked Mike if he would lay down and let me try to lower myself on him. I needed the reassurance of having some control over his massive cock. He lay down and started lewdly rubbing some of the lube on himself. I put some more around my ass and positioned myself over him. I put my hand around Mike's thick shaft and brought his huge cockhead to my hole. I flinched again at the initial contact but willed myself to relax, knowing that if this would work, it would take all my concentration. I could feel the pressure of Mike's tip on my ass but nothing was happening. Will tried to distract me by going down on me but all I could think of was the Coke bottle sized dick I was determined to stuff inside of me. I eased down further and felt the pressure increase against my tender hole but still the tip refused to start inside. I was getting frustrated and sat up a little, then pushed myself back down. When I did, I felt my ass began to open and the head of that monster shaft start inside. I froze to give my overworked hole time to get used to this new invasion, then tried to take more. My asshole felt stretched to the limit and all of the head wasn't inside yet. I tried what worked the first time and moved up before settling back down. I felt a stab of pain again and was beginning to think this just wasn't going to work when I felt my ass give and Mike's knob slid passed my opening. I gasped at the indescribable feeling of being stretched so wide. I dared not move for a while fearing Mike was going to rip me apart. In just a few minutes I felt my ass adjusting to being stuffed so full of cock and started to enjoy what I felt. I reached under and closed my fist around Mike's cock and moved slowly up and down. I held my breath as I felt my ass actually swallowing more of this huge prick each time I eased down. Mike then put his hand on my back and urged me forward. Somehow he moved with me as I leaned over so that his dick never slipped out. I now found myself on my hands and knees ready to get fucked dog style. Mike put his hands on my hips and continued the slow movements I had started. As more of his thick cock slipped in my ass, I had to fight to keep from cumming from the sensation. After just a few more strokes I felt his balls brush mine and I knew I had made it. The shaft that I never thought would fit was stuffed snugly in my ass. Mike remained all the way in for a minute or two and then leisurely pulled back until just the head was still in me, then stretched me again by thrusting forward. I was shocked at how good it felt and that there was no discomfort. I remembered what Will said about a finger not feeling half as good as a cock and I knew exactly what he meant. I also liked the feeling of being dominated by Mike. He was using his hands on my hips to pull me back to meet his plunging dick. I heard his breathing getting ragged and sensed he was getting close to orgasm. I enjoyed giving him pleasure and started to force my ass back each time he impaled me. I couldn't hold myself back as he got more forceful and my own prick started squirting jets of come up on my stomach. A few strokes later, Mike groaned and locked my ass back onto his thick cock. I felt his dick start pulsing and swear I could feel his cum spewing deep in my hole. When his orgasm subsided, he withdrew from my punished ass and I remained motionless while I felt his cum running out of me and dripping down my legs. I enjoyed my first fuck and although I still get into sex with girls, I visit Will and Mike every other month or so to satisfy my need to be filled by more than a finger.