Let me start by saying I have just discovered this site. Sometimes I don't know if these are true or just made up. This is true and actually happened. I am a mid-level manager in a large retail organization. I travel to New York several times a year. To help with expenses my company offers a nice bonus if you agree to room with someone. My boss and I have been working together for a few years and have much the same lifestyle so we definately take advantage of this extra money. We are both married with kids, when this began I was 37 and he was 41.
After rooming together for a couple of years I would have assumed at some point we would have seen each other in the buff but it never happened. We were both very concious to give the other some privacy when getting dressed or undressed. Sometimes our work schedule in the city did not overlap and I happen to have some free time in the room alone. I never missed an opportunity to lay back and have myself a nice long jerk off session. I always thought John was a great looking guy, but we are both just normal men. Your average middle age guys.
One night we got in from dinner and turned on a college Thursday night football game and started having a drink. We had both changed into our usual sleeping attire, old college t-shirt and cotton shorts (I knew I was hanging loose but not sure about John). This was the first time I can remember that we had some free time this early in the evening without dinner with some people from work or a client. At some point our talk turned to sex. I asked him if he had ever been to our local adult newstore back home and was surprised that he said he had. Gradually our talk turned more personal and the subject of jerking off came up. He wanted to know how often I still jerked off. I told him probably 3-4 times a week and enjoyed every minute of it. He was the same. He even had a habit of doing it early on his back porch when he went out to get the morning paper. I could not believe this. Here is my boss at 6am out stroking his cock before coming to work. I had a good idea of what it looked like.
I asked him if he had done it on this trip (This was our second night in NY and last). He told me yes, as a matter of fact he had taken care of business this morning when he got out of the shower cumming in the bathroom sink. I could not believe I had been sound asleep right outside the bathroom when he had gotten off. I had to admit that as soon as he left that morning for a meeting I had thrown back the covers and had a nice jerk off session myself. With all of this discussion I could not bring myself to get off the couch due to my hardened state. I wondered if John was as hard as myself. We continue to discuss jacking off, sex and pornograhy for several hours. Around 2am we both managed to make it to our beds still very aroused. After serveral minutes of trying to sleep but with my cock still standing at attention I knew it was not going to happen. I finally rolled over and in the dark asked John if he was still awake and he was. I asked him if he was hard and of course he was. I said I am not going to be able to go to sleep until I take care of this. We both decided to jerk off in the dark. We both pushed back the covers on our beds and at the same time and worked our shorts down to our ankles. Freedom at last.
It felt so good to be hard and able to rub my cock. Now I am only around 5 inches but I could not believe how hard I was knowing John was in the next bed stroking away on his cock. After several minutes the breathing in the room was growing very heavy. I wanted this to continue forever. I finally worked up enough nerve to ask John to come over and let me give him a hand. I really wanted to find out what he was packing. I expected a no thanks but in no time he was up and moving over in the dark toward my bed. That was it, in minutes we were both all over each others cocks rubbing them for all they were worth. He was about 6 inches and hard as a rock. My hand felt so good wrapped around that hard dick. He had a geat time feeling up my balls and giving me a good rubdown in that area just behind my nutsac. I did not know how long I was going to be able to hold out. I told him to lay back and let me take care of him first which he had no problem with doing.
I went to the bathroom and came back with some of the lotion that they leave for you. I want him to last for a while so I took my time rubbing his shaft very careful only to rub up to his head every fourth or fifth stroke, stopping every now and then to rub his great balls. I could fill the tension building with each stroke until I knew he could not last much longer. That's when I started fisting him quickly covering his entire shaft and head with quick strokes of one hand and massaging his balls with the other. I felt the familar pumping behind his balls as his cum began to make its trip to freedom. He cried out I'm coming, I'm coming and he did all over his stomach and my hand. Wow, it was great feeling another man come in my hands. As he began to relax I got in position for my turn but turns out once he came he was not interested in returning the favor. Needless to say I had a huge case of blue balls until I got home the next day and was able to take care of myself at home. This is not where the story ends. I will post my further adventures with by boss (and how I finally got some help) in later posts.