Business & Pleasure

Chapter 01: My First Time

I have read several stories about first time encounters and realized that my first time was both interesting and maybe intriguing reading for others.

I was 39, happily married with 2 children and in a very hectic business world. While I had thought of encounters with men, it was always just a fantasy. In the sports dressing rooms, I would glance at other men's parts but again never taken it any further.

What changed was while on a business trip, I was propositioned on my way to my hotel by an attractive younger hooker. When I said no thanks ... she said are you sure ... I may surprise you with some extra parts I have. I stopped and looked at her and realized she was a he.

I went to my hotel and could not think of anything else, wondering what it would be like to see her (him) undress turned me on to an explosion.

Some time later and back in my office, I was introduced to a new consulting company we were using. The boss and one of his colleagues (Bob) discussed how they would be assisting us. After a few minutes of discussion, I realized that Bob, who was in his mid 50's, was likely gay. For the next couple months, the 3 of us would do lunch every 2 or 3 weeks after meetings, until one session, when Bob's boss mentioned he had another meeting and that only Bob would take me for lunch.

By this time, I had a pretty good relationship with both of them, so the lunch conversations were generally friendly. Bob took me to this new restaurant and the discussion turned to the menu and that he liked to cook. He said he often invited small groups of friends over and he would make dinner and dessert. I quizzed him on some of his specialties and they sounded great. He told me that a lot of wine flowed at these dinners, and said that once 3 of the guys that had dinner were too drunk to drive home so they crashed at his place – one on the couch and 2 in the spare bedroom. He mentioned – maybe deliberately – that he was not sure what went on behind the spare bedroom door where 2 were sleeping, but he heard some interesting noises.

Out of the blue, he said that I should come over some time for ribs, one of the dinners I commented that was a favourite. I said that would be great, and he said he would get me some potential dates. Lunch concluded and back to the office grind I went.

The first of the following week he called and we set a date. My wife was used to late business dinners so did not expect me. I arrived at Bob's condo and was rung up to his suite. When I arrived I was greeted by Bob in an apron and a wonderful aroma of dinner. He said to get comfortable on the couch and a few minutes later gave me a tour of his condo. It was massive, but also warm and inviting. When he got to the spare bedroom, he mentioned again that this is where his inebriated guests end up staying.

We enjoyed a delicious dinner and small talk over a couple glasses of wine. I was now curious, so asked, did he have family. He said he had been married for 25 years, but work and his interests ended it. He mentioned quite openly at this point that his interested had shifted to men and that he had been gay for about 10 years. It now confirmed what I had thought and I asked him what happened that made him switch teams. He mentioned that many men have the desire and he had always had known this and that once he explored it he was very comfortable. I asked him a couple more similar questions which I am sure piqued his attention. He suggested that he get dessert ready and remove the dishes, and that I should relax again on the couch ... that he would put in a video for me to watch that I might like while I waited. He started the VCR, and went to the kitchen. To my surprise, it was a porn video, and well was a guy and a girl getting it on, but shortly thereafter in the video, the door bell rang and another guy joined the guy and girl, and before I knew it there was a threesome happening, and then just the two guys ... in my already tight pants, was a bulging hard-on. I wiggled to hide it, but the video was such a turn on ... I had never seen two guys intimate and well sucking each other. I know this sounds weird, but I was really naive to all this.

Bob called from the kitchen and asked if I was enjoying the video ... and I responded that it was sure interesting. He came and sat on the same couch and said it was his favourite that he jerked off to it all the time. I looked at him with surprise and interest as he said; he needed to enjoy the moment, and unzipped his pants and pulled out this thick cock. I tried not to stare, but it was almost impossible as he fondled himself till he was rock hard. He stopped and asked if I was turned on as well ... and before I could answer, he reached over and pressed my crotch and said I can see you are. He said what parts of the video do you like – the men or the women ... I nervously responded, that it was all good.

He suggested that I might want to relieve the pressure and pull out my cock ... when I hesitated, he again reached over and said, let me help. He undid my belt without any resistance from me then unzipped my pants, yanked on them and pulled then down to my needs, which were kind of wobbly at this point. He said go ahead, I pulled out my hard 7" cock with a bulging head and watched the video and played. Every so often I would grab a glimpse of his cock.

After a few minutes, he said, you know we would be more comfortable in the bedroom, that he would take the video to the one in there. He grabbed my arm and said, let's go. I did not resist, hanging on to my dangling pants as he led me a few feet to the bedroom. Once there he put in the video, turned on the TV and proceeded to undress. Still a bit stunned, he said here let me help you ... unbuttoned and removed my shirt, and then took my pants off my ankles. With my hard cock in my shorts, he slid his hand over my cock and commented on the size of it and the head. He then slipped his hand into my shorts and wrapped his hand around my cock and then pulled it out. He pulled me over to the bed. It was so unusual but pleasurable being next to this warm male body. My mind was lost as to what I was doing as the excitement overwhelmed me. He stroked me then stroked himself while we watched the video. He moaned as he shot his load on his chest. This was the ultimate turn on and my legs tingled as I felt myself about to come ... I shot 2 feet in the air, over his arm, the bed and myself, it was the most fantastic release I had ever had. I was now both embarrassed and drained.

We lay there silent for a few moments, when he said we could shower together. I agreed and we walked naked to the bathroom and the large glass shower. He warmed the water, and then beckoned me to join him. He washed himself then me, spending a long time soaping & caressing my balls and ass. When he got close his clock touched mine and I again started to become aroused. He leaned close and kissed the side of my neck, then moved his to my cheek then touched my lips. At first I did not respond, but with my eyes closed, I opened my mouth to his warm tongue and lips. The sensation of his rough cheeks and manly mouth was exhilarating. I had never thought of another mans lips on mine, but it was fantastic. He continued to caress my body and then dropped to his knees. He took my now revived hard cock in his mouth and slowly and steadily slid his lips up and down my shaft and over my bulging head. The warm and inviting mouth forced me to pulse with his every stroke. When I got close to coming again, I pulled back and shot on the shower wall and then reeled back with a loss of breath.

We continued to clean up again and then get dressed. We never did have dessert, but did on future adventures, when he taught me more and we shared the pleasures that he introduced me to.