I was in my mid-50s, divorced and a very active bisexual guy. I had been hooking up with men in a gay chat room for several years, even before my divorce. However, the one I frequented disappeared from the web and I went looking for an alternative. I had heard of craigslist but had never used it, so I thought I would give it a try.
I looked under both 'men for men' and 'casual encounters'. There were a number of men looking for sex with men. I browsed the listings and found one from a single guy in his mid 40s who was a top. He posted a picture of his cock, which appeared enormous. I replied to his post and we exchanged a few e-mails which included more pictures. I told him I was a total bottom and would love to worship his cock and that I couldn't wait until I felt it deep in my ass.
We agreed to meet for a drink at a bar next to his apartment house. Mike was waiting for me. He was quite a bit taller than me - around 6'3" and in pretty good shape. He was clean shaven with light brown hair and green eyes. I ordered a drink and we chatted a bit. Like me, he was divorced but had been for over ten years, while my divorce was fairly recent. I sensed that he was a little nervous and he mentioned that he had not been with a guy for some years. Lately, he had been fantasizing about it more and more. I had been indulging my bi side for about 5 years so this was almost routine for me. I told him everything would be fine.
We walked across the street to his building, Mike had a fourth floor condo which was decorated in a very masculine way - lots of leather furniture and sports memorabilia. We adjourned to his bedroom and quickly undressed. It was obvious that Mike spent a lot of time at the gym as he was lean and muscular. His cock sprang free from his boxers and was very erect. It was about 8" and thick with a nice mushroom head. As soon as we were both naked and I sank to my knees and wrapped my lips around that mushroom head. I soon had him moaning with pleasure. The last thing I wanted was for him to shoot his load too quickly so I started licking his balls and fondling his dick. After a few more minutes of this, we got into the bed. I lubed up my ass while Mike put on a condom.
I got on all fours and Mike started to push his man meat into my waiting hole. I just love the feeling of my ass being invaded by a nice, thick cock. Mike inserted it bit by bit, giving me an incredibly full feeling. Once he had his rod in balls deep, he let it rest there for a few seconds before he started to very slowly fuck me. I was in heaven being fucked by a big cock. Mike soon picked up his pace and began really pounding my ass. I absolutely loved it. I kept telling him how good his cock felt inside me. "I love your cock!" I yelled. That seemed to get Mike even more excited and he fucked me even harder. That only drove me wilder and I kept saying how much I loved having him fuck me.
"I'm going to cum!" he shouted.
"Cum in my mouth!" I cried. Mike pulled out and tore off the condom. I wrapped my lips around his cock and started sucking. Seconds later Mike shot string after string of hot cum into my eager mouth. I swallowed each drop and kept sucking to make sure he had nothing left.
"That was intense,' Mike said. We decided to take a break and have a drink. He told me that he had fooled around a lot with men in college and for a few years after. But, he decided he wanted a family so he got married. It wasn't a good idea, they really were not compatible and never got along. He was glad they didn't have any kids. He dated many women after his divorce but never had a serious relationship. He missed gay sex and had been thinking about doing it again for a few years. Mike was not the sort to frequent gay bars, neither was I for that matter. He had been looking at gay porn on-line and finally decided to try craigslist.
After we finished our drinks, we went back to bed. I ran my hands all over Mike's body, loving the way his muscles felt. I began to fondle his balls and stroke his cock. He was hard again and I began to lick it like an ice cream cone. "Suck it, suck it," Mike said and I was happy to comply. I slowly took his shaft into my mouth and went all the way down to the balls. I worked my way back up to the head just as slowly. Then I wrapped my lips around his cock head and massaged it with my tongue as I fondled his balls. Since he had already shot one load, he lasted a long time and I enjoyed every minute of feasting on his bone. "I'm gonna cum!" he said finally and I started to suck harder so I could get every last drop. I didn't have to wait long for his cock to erupt again. I was really turned on by this and had been stroking my own cock while sucking Mike's. I shot my own load about 30 seconds after Mike.
"Wow, that was incredible. Why did I wait so long?" Mike asked. I told him that I had gone over 25 years without man sex before starting again. I had asked myself the same question many times. We lay side by side on the bed, two middle aged guys who were a bit tired after some fantastic sex. We agreed to meet again soon. I asked Mike if he would be interested in a threesome or more. "Hell yeah!" was his enthusiastic answer. I began planning that event immediately.