The following is a combination of wishful thinking and a few experiences I've had.
I was just out of college and had spent quite a few years dating women off and on and basically fooling myself into thinking that women and marriage were the life I wanted. Long story short, I had broken up with my then fiancee and a couple of months later I was pretty depressed and very sexually frustrated.
Ever since I was a child I had always had an infatuation for older men and I decided that while I was unencumbered I was going to satisfy my curiosity and see where it led. I had begun chatting on the internet with Charlie, a 70 year old man who lived about an hour from me. He knew full well that my experience with men got about as far as watching my friend jacking off and was very eager to "break me in" in his words. I told him how apprehensive I was and he assured me that I was in full control to refuse anything and that we would start off slowly. This did put my mind at ease and after a couple fairly insistent requests on his part, I finally agreed to meet him at his house in the afternoon.
He had a small condo near the outskirts of the city that was back from the main road and surrounded by tall trees that shaded everything. I pulled into the parking lot and my nervousness was growing by leaps and bounds. By the time I had walked to the front door, I could feel my heart pounding in my ears and my hands were shaking. I was about to push the doorbell but the front door swung open before I got the chance. And there was Charlie, beaming at me with his intense blue eyes.
"You're right on time, come on in!" he exclaimed. I mustered a wan smile of my own and walked through the door. "Let's go to the living room and chat a bit. Would you like anything to drink?" he asked.
"A glass of water would be wonderful." I said.
"OK, just wait here and I'll go get it."
I had only seen Charlie's face pictures before today and I knew he was a handsome man. He had a big, thick, full head of white hair atop a well proportioned head punctuated by those unforgettable blue eyes. His rimless glasses were barely noticeable perched on his slightly bulbous nose. He had a wide, beautiful smile with two slight jowls that seemed to make the smile all the more welcoming. As he was walking to the kitchen to get my drink, I got the opportunity to take a good look at the rest of him which was just as gorgeous as his face. He was a tall, heavy-set man with a certain thickness that made him look unmovable, but he also had a slight bounce in his step that denoted a natural grace as well. I heard him lightly humming over the tinkling of ice against glass and in a minute he reemerged from the kitchen bearing two drinks.
I supposed he saw me staring at his body and said, "You like the rest of me?"
"Y-Yes", I replied.
"Well that's good!" he smiled. "Let's go sit in the living room."
We walked into the living room, which was furnished with a big couch, loveseat, recliner, and of course a giant television with the sounds of a golf tournament playing softly. He sat on one end of the couch and put the drinks on the coffee table. If my nervousness wasn't noticeable before it must have been obvious when I sat on the recliner instead of the couch. I realized right when I sat down that I might be insulting him, but he was unfazed. He had an air of confidence around him that was almost hypnotic; he seemed like he knew exactly what was going to happen and when. I, of course, didn't possess such powers and so we began chatting about my life, his life, what I wanted to do, all those things. I could feel myself relaxing a little bit and he noticed. I asked him a follow up question about his business travels and his demeanor changed subtly and he stood up and grabbed my hand and pulled me close to his face, his touch was electric.
He said softly, "I suppose I could talk to you about that, but I think we both know why you're here." I didn't know what to say so I simply nodded. He pulled my arm and he led me to his bedroom.
"I want you to sit on the edge of the bed and lean back." I mutely complied, but the nervousness was creeping back and he quickly said, "Look, we don't have to do anything you don't want, but I'm going to tell you what I want. I'm going to pull your pants down and you're going to let me suck your dick until you cum in my mouth."
I was nonplussed at the frankness of his words but weakly replied, "I'm sorry but I can't cum from being sucked." This was actually true; despite the heroic (sometimes unenthusiastic) efforts of my girlfriends, I had never even gotten close to orgasm. He looked completely unsurprised and laughed.
