Many Firsts / My First Caning

The following story is fiction about caning. The story contains scenes of spanking, caning and gay sex. If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now. This is Part 2 of the series and you should start with Part 1: "My First Paddling".

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Many Firsts
My First Caning
By
YLeeCoyote@juno.com

To say that I was confused as I made my way home and for days afterwards would be a major understatement. The only thing that was clear was that my ass had been on fire although the flames were down to mere embers by the next morning. So much more had happened then just the paddling — the sex, of course, but even more so was this was with Mr. Zack Adcox — my long time nemesis. I couldn't help to wonder if I had said to stop if Zack would still have fucked me. It really wasn't like a teacher fucking a student since we were peers (well, we had been when we were in school) and certainly still the same age. I don't feel like it was rape since I never said 'no' nor 'stop' but just obeyed his orders to stay in position. Later after the role play was over, I just had sex with him. Would it be more honest to say I serviced him? I did enjoy it and even came in my pants without touching my dick which did not seem to be of any interest to him whatsoever. One thing was for sure — he was charismatic and I was under his spell.

I got one answer as I slept. I had a very vivid dream about what had happened. The theme that past through all the scenes was clear — Zack was in total charge and I was obeying his every command. Whatever he wanted, I did. It was that simple. It must have been hot because when I woke I found that I had made SEVERAL sticky messes in my bed. This was the most exciting wet dream I ever had. I tried to call him and to connect again through the web site, but neither worked. I even went to his house but chickened out as I was afraid to go in assuming that the doorman would chase me away. I found some solace in my dream which, delightfully, I experienced several times.

Then it happened — I got an e-mail from him. I immediately got hard as a rock. I had to open my pants before I could open the message. It was brief. It was written like a British school behavior report. I was named, of course, there were some infractions specified and a time to report to the Head Boy for guidance and discipline. I practically came as I read it but it took a couple of strokes for that to happen. I was positively thrilled.

Again there were instructions about how to dress. It was curt: "PE kit without pants is to be worn for punishments." Fortunately, there was a link to images which showed what the British Public School boy would wear and a note that any sort of trainers would be acceptable. Thanks to the web, I learnt that 'pants' meant underpants and 'trainers' were sneakers in British. I only had to buy a couple of items to have the proper uniform but they were cheap enough for my limited budget.

Two evenings later I was pacing in of front of his house, once again nervously awaiting the proper time to report, and wearing a raincoat over the PE kit to keep warm. The doorman passed me in and soon I was sitting on the bench outside of Head Boy Adcox's study with my raincoat hidden out of sight underneath. I realized that I was here because Mr. Zack Adcox directed that I should report for a caning and, presumably some sex, again of his choosing. I was not sure about being caned but I definitely wanted to have sex again.

I knocked at the specified time and received a grunt to enter. He was sharply dressed as a Head Boy in the appropriate uniform with long trousers and a blazer as I had seen on the web site. I stood in front of his desk while he lectured me. My eyes were riveted on the cane that surely would soon be thrashing my ass. Then came the order. "Drop your shorts and get into position for six-of-the-best on your bare bum for your disgusting conduct." I was even more excited than the first time as I was certain that after I was caned that there would be great sex.

I had no idea that the cane was so painful. I heard a gentle swoosh like the wind and then — suddenly — a red-hot rod landed right in the middle of my cheeks. I jumped up, grabbing my ass and yelled like a banshee from the pain. But Head Boy Adcox wouldn't have any of that sort of nonsense. "Back in position, boy. You get up again and the cut won't count." I got back into position and gripped the far edge of his desk like my life depended on it. In a sense it did, for if I let go I would get painful extras.

The second cut was as horrendous as the first but I did not dare to leap up so I only yelled. All I could think of was only four more and that thought was shattered when the cane landed on my tender rump for the third time. I could not even yell properly because of all the pain. The next two I couldn't even count as I was in such pain. The sixth and most vicious he laid across the first five making (as I later learnt) a five-bar gate.

I had shifted my position but he pushed me back down flat the desk and held me still as he rubbed my thrashed bottom. Naturally he quickly gave his full attention to my butthole and soon had several fingers in it, stretching it so it would more readily accommodate his powerful fuck rod. Although my ass was still screaming from the fires he had ignited in it, I welcomed his invasion. The pleasure from his pounding my prostate was fantastic and overpowered the pain (at least for the nonce). Again, he was totally controlling me with both pain and pleasure. I was not surprised that I again made a mess on his desk. He prolonged his fucking with pauses until he was satisfied. After he withdrew he ordered me to clean up and then join him in the living room for a drink after putting my clothes neatly on the bench or to leave.

I certainly did not care what conditions he set as long as I could stay with him and presumably feast again on his juicy rod. I joined him as fast as I could. He had me bend over so he could get a picture of my marked bottom. "The tram tracks are showing very well and the gate is perfect." he said giving me a soda while he had his fancy scotch. "Boys don't have alcoholic drinks — especially naughty boys who have just been caned." he declared, making sure that I knew my place.

He sat in a big chair and directed me to kneel on the carpet directly in front of him. I stared at the tent in his trousers made by his puissant cock. "You want it, boy." he said and it was not a question. "Beg for it very humbly, boy."

It took me several tries before I used all the words he wanted to hear. "Please, Great Master, may this worthless one pleasure you by sucking your magnificent man cock?" Only then did he allowed me to open his pants and service him. It was wonderful to be permitted to obtain his wonderful essence. When he had finished feeding me, I thanked him for the honor as I tucked his wonderful cock back into his pants at his direction.

"You should have started doing this back when we were in the eight grade, boi, but you were too much of a sissy wuss then and all through high school as well." Zack, as always, was right. "You would have made a fine fag back then. If we had been in a British school you would have been my fag." He then had me refill his drink. Just as I handed it to him, I got a shock. Without any warning, he wacked my hard cock with a short stick. I yelled and went soft immediately. "You have no need to be hard, boi. Your little pee-pee is just your little water spout." I didn't know what to say or do so I stood there like an idiot. Zack knew what to do. "But you haven't found your true calling — you should be a houseboi — my houseboi." he continued and dismissed me.

I quickly dressed by the bench. Putting my raincoat on in the hall and made my way home. As I rode, standing of course, on the subway train I thought about what had happened. It was terribly humiliating but strangely I was happy I had gone and received his attention and more.

I did not understand what I was feeling but I wanted to go back. The idea of being a houseboi — especially to Zack — was very strange yet terribly intriguing.

Continue with "My First Disappearance"

Your comments are appreciated. YLeeCoyote@juno.com

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