I was traveling regularly on business and stayed in the same hotel every week so I knew the layout of the rooms etc. This Monday morning, I was waiting in line to speak with a member of staff when I heard a woman bitterly complaining that she had made a reservation and she wanted her room only to be told by staff that they were very sorry but they had no record of her booking and they were completely full.
After a few minutes of this argument I was getting late so in a moment of impulse I stepped up and said that I had a twin room and that if she thought it acceptable she could share with me, at least for that night. Everyone, not the least me, was surprised at this offer, it is not the 'done thing' at all but seemed to be the only way to resolve the situation. The woman gawped for a minute and then said that because she had important meetings she had no choice, she agreed. The hotel staff issued her a key to my room, I did what I needed and went off to work.
That evening I came back to my hotel with trepidation, went to my room and I could see her bags on one of the beds and I could see that she had unpacked again I thought 'Oh My God', decided I would not tell my wife. I dropped off my briefcase and went down to dinner. Not even my colleagues were aware that I was sharing with a stranger and at the end of dinner we all went up to our rooms, when I got to mine there was still no-one there. I got into bed and went to sleep.
The next morning I awoke and forgetting that I was sharing, jumped out of bed in all my morning glory (I sleep naked) and headed for the bathroom. After relieving the need to pee I had a shave and shower and was just walking out of the bathroom drying myself when I heard 'Good Morning!' There she was in the other bed looking at me, her eyes were as round a saucers and it was not my face she was looking at. I mumbled something about her being late last night and she said yes, she had late meetings and I got dressed as quickly as I could and headed down to breakfast while she was in the bathroom.
That night I had dinner with my colleagues and was sitting in the bar reading my book when she walked in. I still did not know her name but she spotted me, sat down and introduced herself as Carolyn. I shook her hand and said hello and then began the awkward silence. I could see that she had had a few drinks by the way she had walked on over and the next thing I know she said to me 'That was a fantastic show this morning'. I apologized, told her that I had forgotten she was there and it would not happen again and she surprised me by saying that she hoped it would. She explained that her husband never showed himself to her naked, he always wore shorts to bed and when I asked her about sex she said it happened just a few times a year and always in the dark.
Carolyn then asked me if she could see me naked again, she said that she wanted to explore my body. I'm not that much to look at, middle aged, slightly overweight but with a healthy dick but I am married and my first thought was, Is This Infidelity? Being a man I quickly decided that this sort of opportunity would not come around that often and what the heck! I agreed.
We finished the drinks and went up to the room where I let us both in. We got some more drinks from the mini-bar and I asked Carolyn how she wanted to do this, she told me to strip, slowly and so I did. When I got to my shorts it was obvious that I had a raging erection, Carolyn said hold on and she came over and put her hands on my waist. It was like electricity coursing through my body as she slowly slid my shorts down over my hard on. Like that morning her eyes went wide and she could not take her gaze off me. I stepped out of my shorts and just sort of stood there for a while as she looked. After a few minutes I asked her Now what? And she replied by asking me if she could touch me, I said yes and with that she surprised me by starting with my back, she slowly pushed me to the bed and had me lay down as she ran her hands over my back. After 10 minutes of this she said 'Roll Over' which I did and again my erection was there for her to see. By now I think she could not wait and she slowly encircled my penis with her hand, squeezing gently. For the next few minutes she squeezed my dick and fondled my balls all the time not saying a word and then she slowly slid her hand down my cock and the head popped out from my foreskin and she said 'Oh My God' She did it again and I said to her that if she kept doing that there was likely to be a mess. She asked what I meant and I could not believe that she did not know anything about how blokes masturbate so I explained to her. I could see that she liked this as she again started to run her hand up and down my cock, ever so slowly and I could already feel that pre-cum tension starting in my balls. I asked her to go slightly faster which she did, she was watching avidly as I lay there quietly groaning and pushing up with my hips.
I could feel it, I was about to shoot my load and I said to her that I was about to cum and to watch out and at that moment the orgasm hit me and I shot a load which landed on my chest and on her hands. There were a couple of good spurts and then a dribble and she stopped wanking me and looked at her hands and the mess and my quickly shrinking dick. We looked at each other and laughed. I got up and we both went to the bathroom where we got cleaned up and then we went to bed. This time she put on a show for me as she slowly stripped but then she put a nightie on. I was resolved to get her to sleep naked by the end of the week but that is another story.