I was traveling on business as I do quite frequently. I was in San Diego, CA and had a free day. I had a real craving for a good spank session and went on the Internet to see if I could hook up with a good TOP man. I dont usually do a lot of searching on the Internet because I have been very particular about my experiences at being a truly submissive bottom boy. I went to gay. com and began chatting in the San Diego chat room. I have a cute ass pic that I have in my profile that hopefully attracts the right guy or at least gets a hot guy to do some chatting. After a bit I got a private message from a guy that seemed really interesting. He said he was a mature guy 58 yo and he was looking for a bit of afternoon fun. We chatted about each others wants and found that we had some real common interests. He was a top that enjoyed dominating a smooth bottom boy. He was "into" spanking and chatted like he had plenty of experience. I was getting hornier by the minute. We decided to exchange some pics and see if we had a desire to hook up. When I got his pic, I knew that this guy was someone I had to meet. He was tall, 62" and 225# with salt and pepper hair and mustache. We chatted more and I asked him if he would like a submissive for the day. Actually I think I begged him. He said he was very interested but I would have to play by his rules. My _c_o_c_k_ immediately got a very warm feeling. I agreed to meet him and he wanted the first meeting at my hotel room. My instructions were quite clear. I was to go out and buy a dark blue jock strap to wear and a fresh tube of KY. He would be at my hotel room in one hour, I was to leave the door ajar and I was to be standing in the room with only the jock strap on with my back to the door. My tight ass was to be lubed with the KY and basically ready for whatever. My anticipation was already at an explosive level.
I left the room after we finished chatting and headed for the nearest shopping to make my purchases. I was able to find both items fairly quickly and get back to my hotel room. I did as I was told and readied myself as instructed. The time clicked by so slowly and my nerves where just a mess. I opened my door and left it slightly ajar and stood in the room with my back to the door. The room had one king bed and a sitting area. I stood in the sitting area awaiting my Master. The time of his arrival came and went, 5 min, 10 min, I began to think I was stood up. I was afraid to move thinking he would walk in while I was not in "position". Then I heard the door open and be closed and locked. His voice was low and cool. Do not turn around! Stay still and put your hands behind your back. Nothing else was said. He approached and suddenly I felt his cool hand on my bare ass. Feeling, kneading, adjusting the straps on the jock strap. His hand slid around my butt to my now hard _c_o_c_k_. It was bulging out the front of the jock quite nicely. He began to examine my body, touching softly at times and very firmly at others. His finger examined my ass crack and he gently probed my tight hole. I think making sure that I had applied the KY as directed. I was glad that I had applied plenty of lube. He spoke again, very slowly and had me spread my legs and bend slightly over. He proceeded to fully examine my tight hole. Finally inserting a finger. He had larger hands and his finger at first surprised me. He held it there for a minute and then removed it. My _c_o_c_k_ was really throbbing now. This did not escape him. I was trembling with desire and he knew it. He said slut boys like me needed to be specially treated to make sure they always pleased their master. He came around and stood in front of me. His hands slide in the waistband of the jock and he slowly pulled it down exposing my now dripping _c_o_c_k_. He cupped one hand under my hot balls and with pure surprise and shock he took his other hand and slapped the tip of my _c_o_c_k_. I groaned in pain. He slapped it again. He said: This is mine and you are just to be here for my pleasure. This _c_o_c_k_ does nothing without my permission. He slapped it again for effect and I submitted to his wishes and told him that yes indeed it belonged to him. He released his grip and put the jock strap back in position covering my _c_o_c_k_ with the jockstrap. I was really feeling hot and anticipating his next move.
He took the straight back chair from the desk and sat it in the middle of the room. He sat in the chair and had me approach him. He told me to lie across his lap. I did so without any hesitation fearing what would happen if I didnt. I lay there for what seemed like forever before I felt his hand on my backside. He gently rubbed my ass, not saying anything. Then suddenly Whack! He knew how to spank, I could tell from this first whack. He hit me square on my right cheek, not up near the back but in the tender fleshy part just above my leg. Then again, Whack! My left cheek got its share. This continued slowly but surely until both cheeks got exactly 10 whacks. He was a real professional. My ass had no welts or bruises but was the most wonderful pinkish color you could imagine. My _c_o_c_k_ was hard and my ass was sore. I just wondered what was next. He slowly rubbed my red ass. Telling me what a good boy I was to take the spanking without whimpering. He caressed my sore ass and gently fingered my puckered hole.
He told me to get up and go over to the bed. To get on the bed face down with my ass in the air and right at the edge of the bed. He told me to keep my face down and not to turn around at all or I would get some real punishment. He approached the bed and touched my hot ass. It was such a caressing touch. He took the tube of KY from the dresser and I suddenly felt the cooling gel being applied to my tender asshole. He inserted a finger and began to slide it in and then remove it. He was making my tight ass wasvready for something else I knew for sure. This fingering continued with one then two fingers. He held the two fingers in place letting my ass get use to the insertion. He held them there for several minutes pushing ever so slightly. He removed his fingers and told me not to move. By now, my balls were aching and my _c_o_c_k_ was just about to explode. There was no sound, and then suddenly I heard his zipper being undone. Then I felt his hands on my butt. My anticipation was just overwhelming me. I felt his hot _c_o_c_k_ on my ass. He rubbed the tip up and down the crack and finally paused the tip at my waiting hole. He applied slight pressure and I immediately froze clinching my ass. His immediate response was a sharp slap on my ass then another. I force myself to relax and again he pressured the tip against my hole. He pushed forward until the tip forced its way in. He stopped and waited, letting it stay there until he felt I was ready for the onslaught. His _c_o_c_k_ was good size. 7" cut medium thick with a very nice tip. He slowly leaned forward forcing the length of his _c_o_c_k_ into my ass. My feelings where just all over the place, it hurt, it was pleasurable, I wanted more. Slowly he began to thrust in and out. He would come completely out and re-insert each time. He was getting maximum pleasure out of my tight ass around his _c_o_c_k_. I cant say how long it lasted but my ass loosened and readily accepted his _c_o_c_k_ and it really felt so good. His orgasm was powerful and he grabbed my ass and pulled himself in as deep as possible. I was beyond words. I was just a puddle and willing at that point to do anything to please him. Knowing that he shot his hot load in my ass made me truly feel like his submissive boy. He withdrew his _c_o_c_k_, told me not to move. He went to the bath and cleans himself and returned. He had a washcloth and washed my bottom. I begged him to let me masturbate and cum. He was firm. He slapped my ass and said I would cum when he was good and ready. He was leaving now. I was to get myself together and I was to meet him at his house in two hours. He wrote directions for me to follow including some additional personal instructions and he left. My head was spinning. I was so excited and wanting so much more.