Trevor's First Gay Experience

My necktie had been choking me since I put it on after lunch. I left my top button undone and tied a simple overhand knot before meeting my only client for the afternoon. She was a middle-aged widow whom I assisted with the probate of her dead husband's estate. She was fairly attractive and I enjoyed the scent of her perfume. She showed me pictures of her recent trip to New York City and I leaned a little closer to take in her aroma. Unfortunately, the blouse she had on fitted her quite conservatively so she exposed no cleavage.

Of course, I kept everything professional as we signed the necessary documents to close the estate. She promised to return to my office to have me prepare the deed of sale to her real estate. She was leaving the state for the warmer weather of Florida as soon as she could. As she left my office, I pondered how well she could give a blowjob.

For whatever reason by the time I returned to my desk, my thoughts centered on whether I could give a better blowjob than her. I have been fantasizing about some man to man intimacy for awhile now. Usually I wonder what another man's cum tastes like and how well I could deepthroat a stiff hard cock. Sometimes I imagine my ass being penetrated. I never really think about topping another dude. I am always the bottom sub in the fantasy.

I decided a few weeks ago to buy a disposable prepaid phone with a 30-day unlimited plan. I registered the phone and received a random phone number I needed to write down to remember. I went so far as to set up a dummy email account and dating profile. In no time at all, I was receiving emails containing naked pictures of different men along with their propositions. I received mail from all types. I enjoyed flirting with these random strangers but it has never gone anywhere.

Today might be different. I responded to an older gentlemen who expressed a desire to 'train' an obedient student. I was not sure whether this was like a 50 Shade of Gray situation with the leather and chokers, etc... I am not interested in a relationship like that in any way. Nevertheless, I asked what he had in mind and told him of my mental challenge of how well I could suck dry a wet throbbing dick.

He laughed and assured me he was not into any rough stuff unless I wanted it that way. He suggested I visit his place sometime soon and gave me an address not far from my office. He proposed that he would wait for me in the nude, and would have a bottle of Jack Daniel's and some blowjob porn on the TV when I arrive. He said he expected to me to strip naked as soon as I entered and kneel before him. Since the porn would already be on, he would be hard and ready to go as soon as I arrived.

Since I have never sucked a dick before, he thought this would be a great initiation for me. The worst case scenario he says is that I chicken out at the end. In that case, he would tell me to just to open my mouth and he would stand up and jerk himself off onto me. Oh man I thought, this guy has thought of everything. He really had the experience and persuasion necessary to overcome any of my reluctance.

I was not sure how to respond so I told him I was flattered and appreciative of the time he spent communicating with me. I did not want to disappoint him though with my inability to follow through. He continued to assure me he would not be disappointed, and neither would I be disappointed in a new experience. "Come on over," he pushes, and he tells me when I arrive to just sit quietly on the floor with the bottle to loosen my nerves, and when the time was right, he would let me know he was going to cum and would ask what I wanted to do about that.

Ok, fine I thought. And I finally relented. It has been a very long week/month/year, you name it. An adventure is what I craved. And either sucking this guy's dick, or letting him dump a load on my face, was certainly worth considering to get me out of my doldrums. I am on my way over to his place now. Stay tuned.