I was in my early fifties and was finally able to pursue all of my sexual interests. I had experimented over the years and found that I was a submissive man who likes and needs to please others. I found my greatest sexual pleasure through having my ass and mouth used by both woman and men for their pleasure. I was initially only attracted to woman and enjoyed that immensely. I tried being with a man and eventually found that I also really enjoyed the feeling of having a cock in my mouth and ass.
My tight ass began to be stretched through using anal toys, especially butt plugs. Working a big plug into my ass was a thrill and I gradually was able to put in bigger plugs and dildos which felt even better. I kept fantasizing about taking a really large cock in my ass. I needed to feel that feeling of being completely full and taking it all. I placed ads on several websites to fulfill my fantasy. It was a long, difficult, and frustrating process. Many people are not what they say they are. I still don't understand how people don't show up when they promise or don't do what they say. After awhile I got better at screening the undesirables but I could not give up my search. Being with a professional in this way was not fulfilling. It was not real.
I finally found what I was looking for. Thomas answered my ad in a straight forward and clear manner. His picture backed up his statements. He was a large man in many ways. He was six foot four with a large head and large hands. His was nearly seventy and had a no nonsense way about him. He was clear that he loved fucking a tight ass and making it hurt. It was only about his pleasure. And, he had a massive cock. It must have been ten inches long and was thick. It took three of my fingers to measure his entire width.
We arranged to meet at the hotel I provided. I was instructed to be naked, had have an Elena, and bring along any lube I needed. I was so nervous but ready and excited when he knocked on the door at exactly the right time. He strode into the room and ordered me to kneel in front of him. He immediately unzipped his pants and pulled out his monster cock. My eyes went wide. To think about it and to see it where two different things. I stammered and said that I have never taken one so big. He shoved his cock into my mouth and put his huge hands on the back of my head. I immediately began to choke and he did not care. I quickly figured out that I had to open my throat wider and adjust the angle to take him all in without choking.
Thomas reminded me that we agreed on a safe word. Although he will honor it, he told me that he would find his pleasure elsewhere if I could not please him as he desired. He pulled my head off of his erect cock and told me that I was now going to get the fucking of my life. I told him that I wanted his cock deep in my ass and that I would do everything I could to take it all. He pointed to the edge of the bed and told me to lube his cock and my ass if I wanted lube. I immediately lubed my ass. I was glad that I had been practicing with increasingly larger dildos, but I had never taken something the size of his monster cock. I lubricated his massive cock as he stood over me and I felt his power and it felt so right.
He grabbed me and positioned me at the edge of the bed with my ass hanging over. His rough hands moved me like a doll. He lifted my ass to be at the perfect height when he stood behind me. He placed his large head at the entrance of my ass and roughly pushed it part way into me. I was glad I grabbed a pillow as it became my lifeline as I moaned and then almost screamed into it. It hurt like hell. I almost used my safe word but it took so long to find the right man and I needed to take his cock deep in me. I used the pain to help me feel the pleasure. Pain and pleasure are so close to one another. He held his cock partly in me for only a short while and then he grabbed my hips with his hands and roughly pushed his cock all the way in. This really really hurt but I once again let the pain take me and I soon felt this incredible feeling of being so filled and of being so used for his pleasure.