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The following story is fiction about paddling.  The story contains scenes of spanking, paddling and gay sex.  If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now.  This is the first part of three.

This work is copyright by the author and commercial use is prohibited without permission.  Personal/private copies are permitted only if complete including the copyright notice.

The author would appreciate your comments – pro and con, including constructive criticism, and suggestions.  Please take a moment to email.

Many Firsts
My First Paddling


I was nervous like I could not believe as I got on the subway to go to see Him for the first time.  I had responded to his discrete ad more than a month ago and we had exchanged several emails and I was extremely anxious.  Now that he had returned from a business trip I was going to meet Him and learn whether or not my fantasies were good reality for me like in a lot of the stories I had read on the web.

I could not help realizing that I had felt this way before.  It was a long, long time ago when my mother stopped in front of PS114 elementary school and told me to be a Brave Big Boy and join the other kids in the school yard for my first day in first grade.  I was very, very glad that she had made me go pee-pee before we left the house so that I wouldn't wet my pants.  It seemed such a very long time before a teacher blew a whistle and called for all the first graders to enter the building.  I was so terribly scared – either to go in or to run away.

It wasn't much different eight years later on the first day of high school.  I felt so small seeing the huge seniors milling about although I soon spotted and joined the other nervous freshies in one corner of the yard.  I searched frantically for anyone I knew from grade school.  They had to be here also and eventually I found Zack.  We didn't like each other and he picked on me a lot but he was less terrifying than all those strangers.  I found it hard to believe but big Zack looked very nervous.  Then he saw me and seemed to change.  For the first time he greeted me without a nasty comment but like a friend.  We went in together for the first and only time.  The next day he was as nasty as ever to me.

I imagined that I felt like the guys I read about in the old stories from the middle of the twentieth century when they were sent to see the vice principal (in America) or the head master (in Britain) by some angry teacher.  They would have to wait on a well-worn wooden bench until the disciplinarian deigned to call them in to beat them with a paddle or cane.  Of course, it wasn't so simple as that, for there were always the formalities of record keeping and checking parental permission and then a long drawn out lecture that almost made one wanted to be whacked just not to have to listen anymore.  But eventually, it was time and they had to empty their pockets and pull up their pants or drop their trousers and bend over in some way – over the desk or a chair or just grab one's ankles – to present a tender rump offering to the high priest.

The paddle or the cane would be raised and brought swiftly down on the sacrificial flesh like an Aztec priest yanking out the beating heart of a honored victim and holding it up to the sky to offer it to the sun god Huitzilopochtli blazing high above.  The difference was it was not terminal and would be repeated over and over until the all-powerful disciplinarian was appeased.  The physical marks were later shown to peers along with boasts and the emotional scars hidden.© YLeeCoyote

It was more than two decades since that rite of passage into first grade and now I was going to see Him.  Of course, he had a name but I just thought of him as "Him".  I was pretending to be just a thirteen-year-old boy who had been sent to see the vice-principal to get beaten for some infraction of a stupid rule.  Since I was ten-years-old, I was fascinated by those stories of boys being beaten in school.  It must have been thousands, probably even tens of thousands of times that I lay in my bed and yanked my rigid cock and spewing out my cum thinking about it happening; happening to ME!  Now, as a young adult with a college degree and a shitty job, I was going to report to the vice principal like all those naughty school boys did in those stories.  Well, like the boys in schools when decades before CP was still the allowed norm.

His instructions were detailed and precise – time, dress and even words.  I had allowed a lot of time for delays for I had been told that tardiness would not be tolerated.  Beside I was too nervous to wait at home.  I paced up and down the block across the street from his apartment house hoping that his doorman would not notice me.  My alarm went off.  I silenced it and even turned off my phone completely for it certainly would not do to have it go off when I was with Him.  The doorman announced me and I rode up alone in the elevator.  His door was unlocked and I entered as instructed locking the door behind me.  There was a well-worn bench in the hall and I sat on it.  The door next to bench had a sign: «Vice Principal Smith».  I winced for that was the name of the vice principal with a fearsome reputation when I was at school and then I waited.

I had to pee.  I had to pee even though I had just done so before leaving home but nervousness is a powerful diuretic.  There was another door – maybe (I hoped) a powder room rather than a closet in His fancy condo.  I was lucky.  I peed but hardly anything came out.  I had trouble with the tight fly of the snug new tighty-whites I had been ordered to wear and had to push them down instead.  I returned to wait on the bench.  I was sweating.  Mr. Smith had a reputation of being mean and paddling hard.  Apparently I was the only one this day.  It was my first time and I was alone.  I waited and waited.  Little did I know that I there was a spycam in the hall and that Mr. Smith was watching me so as to maximize the experience.

I was startled my hearing my name blasting out.  There was a speaker on the wall and it repeated: "Hossmann!  Get in here. NOW!"  I jumped up and reached for the door knob.  Fortunately I froze and then remember to knock.  "Come in."  I entered the room.  It was like a school official's office.  VP Smith was behind the desk.  I stood in front of the desk.  I clasped my hand behind my back trying to hide my nervousness.  VP Smith was looking at a folder.  "Hossmann – you are a disgrace to this school."  Without looking up, he went on a long, long time chewing me out about my crimes.  I felt like a very naughty and very little boy.  A little boy not even in high school.  I stared at the floor not daring to look at him nor the wooden paddle, with three rows of holes drilled in the business end, that would soon be kissing my tail laying on the desk.

Then came the faithful words that I was waiting for and most feared.  "Ten pops."  I almost fainted.  "Drop your jeans and briefs and bend over my desk." he ordered.  When I hesitated, he added: "If you keep me waiting, it will be twelve, boy."  I opened my belt and jeans and pushed them down.  "Your briefs also, boy.  They didn't do anything to be paddled for like you did."  I pushed them down and bent over his desk.  I grasped the far side.

"Don't get up or there will be extras, boy."  I tightened my grip and waited.

I did not have to wait very long.  He walked behind me with the paddle that had been on the desk.  It looked huge and heavy and vicious.  I think if he had taken another second I would have jumped up and run out.  Instead I howled when the paddle seared my bare rump like a red-hot iron.  It was more painful than the dentist.  After the initial pain, there was the reverberation through my entire body and probably my soul as well.  I did not dare to move.

The second pop was even worse.  By the sixth I was crying like a baby from the pain.  I yelled for each searing pop, of course, and now I was adding pleads to stop and promises to be perfect.

"Stay in position, boy or we start over again." he said forcefully.

I did not dare to do anything else; not even to move a smidgen.  Again and again the paddle landed and I was on fire.  This was not quite what I had been imagining all these years.  My knuckles were white from the death grip I had on the desk.  "Stay in position, boy." he ordered and placed the paddle next to me.

I felt him rubbing my burning ass.  It felt good even when he slipped a finger into my hole.  Soon there were many fingers but I still did not dare to move for he had ordered me not to on pain of more pops.  I knew that I most certainly did not want any more pops.  I knew what had to be next and I still did not dare to move.  Then his potent, rock hard rod was pressing on my just stretched hole.  «NO! Don't!» I was screaming in my head but, of course, he could not hear that as he shoved his ramrod – essentially the irresistible force – deep into my swollen rump which he had just roasted.  And another voice yelled inside my head: «Shut up, boy.  He has the right to fuck you.  He's a powerful man and you're a mere weak wuss.»

He fucked hard just like he paddled hard.  The pain faded and I sensed that I was rock hard as he was pounding my love nut.  I heard him yell about cumming and I made a mess on his desk.  He withdrew and told me to stand which I did.  I saw him remove the condom and wipe his cock before putting it back into his dress pants and after straightening his tie put on his suit jacket.  He handed me a towel and told me to clean up and either leave or join him for a drink in the living room.

I carefully got my jeans back up and joined him in the living room.  He gave me a soda and we talked while he sipped his scotch.  I never expected his next line.  "I've been wanting to fuck your cute ass since the eight grade, boy.  And it is even cuter bright red."

I studied him carefully.  Then I realized that it was Zack Adcox who had tormented me all through twelve years of school.  He was in a good quality business suit with a power tie appropriate for a successful man and I was just a slob in a sweat shirt and jeans like I was still in high school.

"I think that you will be a good boy for me.  Good to paddle.  Good to fuck."  I was dumbfounded.  I stood there like an idiot while he walked over to me.  He put his hands on my shoulders and pressed down hard so that I dropped to my knees.  I was obeying him like I had all through school when I couldn't avoid him.  "Take it out of my pants, boy."  I did and soon I was sucking his hard cock.  I must have liked it because I made a mess in my own pants as I ingested his essence.

"It's too bad that you were too chicken to do anything in school, but we'll make up for it now, boy."

I looked up at him with his potent man-shaft still in my mouth.  "Yes, Master." I said.  He smiled triumphantly and pressed my head forward so my nose was buried in his pubes and his cock in my throat.

Go to: "My First Caning"

© Copyright A.I.L. November 16, 2013

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Last updated:  September 15, 2023