I have never been a wild woman, and last weekend was very out of character for me. I really can't tell any of my friends what happened, and I need to tell somebody, so I have decided to post this here on Literotica for your enjoyment. Everything that follows is true, except the names.
I had a business meeting in San Francisco last weekend, and was in town through Saturday night. I don't know where I first got the idea, but before I left home, I decided I wanted to get a massage while traveling. However, I did not want to go to a professional masseuse and was feeling a little frisky, so I decided to post an ad on Craigslist.
I posted my ad in the barter section, knowing full well that I had no items to barter that I could bring on the plane to San Francisco. My ad was simple, and sought a male masseuse for a woman. I added a few made up details saying that I was out of work, and that is why I needed a free/bartered massage, but other than that the ad was simple and truthful.
Within 30 minutes, I had already received seven emails. Realizing that if I left the ad up any longer I would be barraged by emails, I removed the ad and began replying to each man in turn. Some were very professional sounding, others made it clear they were looking for something sexual. Tim was one of the only guys who simply explained that he had some massage experience, had an empty apartment for the weekend, and offered to massage me in exchange for whatever I might have to barter.
I, of course, had nothing to offer in barter, and responded to Tim saying that I placed the ad on a whim due to my sore back, glutes and thighs (hint, hint), and that I had not thought through the whole barter aspect. I also told him I was open to ideas. Still not sure if I was offering something sexy, Tim said that he was sure we could think of something and asked when I'd like to come by. I told him that Saturday morning would work, and I sent him a photo showing my long blond hair, pale skin, and tight body. I was dressed in the photo, but the sweater and skirt did accentuate my ample bust and my smooth legs. I did not request a photo back, and part of my game was that I would not base my decision on looks, and would allow whoever I chose based on emails (in this case, Tim).
Now extremely nervous, I had three days until my trip and had scheduled a massage with a random stranger in his apartment. We traded a few generic emails through the week, but I did mention that I had been running a lot lately and that my glutes and thighs were tight. I also asked him what I should wear since I had never had a "real" massage before, and I was excited when he responded that I should be nude, but could wear whatever was comfortable. I assured him I was comfortable in the nude, and made a joke that since my glutes and thighs were so sore, I had assumed I would have to be nude for him to work on me. He responded and said that a great barter would be for me to massage him after my massage, and I immediately agreed, despite my lack of training. I said goodbye with a final joke and asked him if I was supposed to get dressed before giving him his massage.
Saturday morning arrived before I was ready for it. I went out on Friday, my first night in town, so I was a bit groggy when I woke up. Once I realized that Tim would have his hands all over me within a few hours, I started moving very quickly! I still hadn't seen him, and was becoming worried, but decided to go through with it, no matter what. My body was already starting to warm, and my pussy was already a bit moist as I thought of being rubbed all over by a stranger.
I called Tim and got directions to his place; it was only 10 minutes from my hotel. When I arrived I rang the door bell and could feel my hands shaking as I waited for him to let me in. I felt like all his neighbors knew exactly what I was doing, but my little lips were still wet and getting wetter. Time opened the door and I took a good look. He was around fifty, in okay shape, gray hair and a little potbellied. He had at least 15 or 20 years on me, and even in my age range I am usually considered "hot", so he was unlike any guy I had been with.
"Sure you don't want to back out? I know I'm not much to look at." He said. "You look fine, and besides, it's just a massage." I replied, still keeping a bit of mystery as to what would be allowed.
Tim escorted me to his bedroom, where he had a massage table set up, with a sheet on top. He stepped out and told me to undress and get under the sheet. It was obvious he was excited, but that he did not know if he had read too much into my emails. I decided that it was now or never, and stripped down to nothing, leaving my little pink g-string on top of my pile of clothes. I then laid down on top of the sheet.
Tim returned and I could hear an intake of breath. He apologized and said he thought I was ready. I then said I was and he responded that he thought I'd be under the sheet, but that he was fine with me on top of it, as long as I was.