This story is fiction and deals with the spanking of m/m spanking and sex.  If such subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now.

Thanks to Mike Ward who helped me with British's idioms and details.  The narrator is speaking of events prior to 1965 when CP was much more common and we did not worry about STDs.  So, consequently, my characters are not concerned about them and don't use condoms as you should now.

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.

The Headboy and the New Master – Part 1


I was not the first Giles Mills-ffleming to be Headboy at Dorwick, an ancient public school, hidden away in a remote, very conservative bit of England, north of Hadrian's Wall with the paneled walls oozing traditions.  My cousin, who was twelve years older than I, had preceded me in the position.  The long time faculty remembered him and for the six years that I was a student at Dorwick, I had extra high benchmarks set for of me because of him.  Fortunately, my cousin was not perfect and had left some room for surpassing his achievements.

As the new term got underway, I observed that there had been few changes in the population of masters, staff and students with the obvious exception of the new boys in the first and that the previous sixth had not returned.  There was one new master; Julian Howlett, BA, for the Arts.  My cousin was showing more interest in me now that I was a sentient creature, instead of a mere infant and, especially, as I was holding the honoured position he himself had held so that we corresponded frequently  He also told me about one of the boys in his year of that same name.  That boy was a full fledged faggot; a crybaby.  Back in the first when he was spanked by hand, by one of the prefects, he cried.  In the fourth, when he was slippered on his gym kit he cried.  Even in his last year – at seventeen years old – he bawled and yelled bloody murder by the third cut even when he was swished by my cousin.

As you can imagine, there is a lot of wanking that goes on in boys' public schools and Dorwick was no exception.  Not all of the wanking is solo, however, for there are those about who want more than a hand.  Since hot, horny youths like hot holes many will take advantage of the willing lad when lasses are not available; well convinced that it is OK since they are taking the male role in the act.  It happened that Howlett was not only a nancy boy but happy to please by submitting to the more aggressive guys.  My cousin quickly learnt how to take advantage and reduced his need for wanking by an order of magnitude.  Howlett visited him regularly to provide excellent oral service.  After a caning or even a slipperring, my cousin would grease up his rod and shag Howlett who was not allowed to get up until commanded.

Something about this intrigued me and I did some investigation.  The new Master looked a lot like the nancy boy in the school photographs.  That made it worthwhile to check his curriculum vitae which provided the definitive answer.  They were one and the same person.  I looked backed on the old punishment books (conveniently on my own bookshelves) and noted that Howlett was listed far more often than a coward should be – strongly hinting that he wanted to be.

You may wonder why any of this was of interest at all.  It was because I quickly developed a strong dislike of the man.  He still presented an image of being a nancy boy and I found his subject distasteful.  Worse of all, he was constantly sending lads to the Head for inconsequential reasons at a far greater rate than any other two masters combined.

* * * * * * * * * * * * *

Permit me to talk about myself and my new position.  In a word I found it BRILLIANT!  The benefits far outweighed the costs of the extra work.  I had quickly found that I loved being a leader and having authority over my peers.  Best of all, I even had the power to use corporal punishment when the miscreant chose me rather than the Head.

Most of the firsts that I dealt with were shaking in their boots even before they timidly knocked on my door.  They all knew about spanking for they had been spanked for years by their parents, governess and other caregivers.  As much as they were unhappy with getting spanked by me they were far more scared to go to the Head, whose fierce reputation was always exaggerated for their ears.  Not only did my feeling of importance and power grow from these encounters but so did my sense of adulthood.  Even though they were only five years younger than myself, opening their belts and lined shorts so that I could pull them down along, naturally, with their pants emphasized that I was wearing longs and unequivocally in authority.  They never resisted my pulling them over my lap and holding them in place while I smacked their little bums even though they would have much preferred to do that themselves and bend over.  There was a penalty for that – as I would then use the slipper and I had a well cultivated reputation about doing that most painfully even to the uppers.  The lads did their best not to cry and never yelled out either with an ouch or plea to stop.  They were brave little men-to-be as I turned their bottoms bright red.  Then, when they were dressed, they bravely thanked me and even shook my hand.

The second through fourth form boys usually got the slipper.  This was a far more dignified procedure.  They would bend over a chair usually after lowering their shorts and pants to present their arses for chastisement.  The slipper I used was just an old plimsoll sole.  It made the most delightful sound when I smacked it onto the target leaving a lovely red mark.  After a session, especially when several lads required such attention, I enjoyed one of the major perks of my position – a private chamber where I could wank in private.

I most enjoyed dealing with the fifths and sixths, my own form, boys.  At least eighty percent of the time the most I could do was use the slipper like with the fourths although the older the lad, the less he liked bending over for a peer.  But bend they did and I enjoyed it even though they did not.  The harshest punishment I was allowed to administer was four cuts of the junior cane.  I practised a lot totally destroying an innocent pillow in the process.  I think that the time was well worth the effort as I really got proficient at it.  The trick, as everyone knows, lies in the wrist.  You all know how delightful it is to admire a mate's stripes but it is even better to admire them when you yourself have inflicted them.

By the time a third of the year had past, I realized that I was fantasising about dealing with guys, bent over, with bare backsides worrying about the cane in my hand primed to thrash them.  To some extent my dreams were realized by my fellow students but then the scope of my desires had quickly broadened to older men.  I doubted that there would be such opportunities here at Dowick for I had little contact with the staff and certainly never even considered the masters.  All I could do was wait until I got to the uni, for the local little village I got to occasionally was truly minute and had nothing to offer.  I'm happy to report that I was wrong.

I needed to do some work on my art project so I went to the arts room.  Since it was a recent addition (only two decades) it had been put into some previously used space and was big enough to contain both studio and class spaces.  I was not particularly surprised to see Mr. Howlett sitting in the couch used by the models and reading.  (The under matrons and sculleries sat, fully dressed, for some drawing classes.)  He was most engrossed and was massaging his crotch as I approached unnoticed.  Most indiscrete of him to be caught doing this.  I could only imagine the roar that the Head would have bellowed had he observed it.  Then I saw what he was reading – a skin magazine – for the cover illustration was of nudes and the name of the same class.

I stepped up to him and snatched the evidence from his hands.  "Howlett!  Doing this again!  This is disgraceful.  What if one of the lowers had come in?  I will give this to the Head in the morning."  (One of the reports in the punishment book indicated that my cousin had caught him doing this as a student.  It was regular procedure that every morning I reported to the Head so there was not any need to rush.)  Howlett was so flustered that he just dashed out of the room.  I put the damning evidence back into the plain brown envelope that it apparently had been posted in and placed it into my portfolio with my sketches and went to work on my painting with a light heart.

It was right after lights out when there was a knock on my door.  I was surprised that it was Howlett.  He looked very sheepish.  He looked as scared as a first former.  "Yes, Howlett.  You wish to say something?" I said as if he were a lower former.

He stammered.  "Yes, Mills-ffleming…I don't think that it necessary to speak to the Head about this afternoon….er…."  Perhaps he saw me just as he saw my cousin twelve years ago.  After all, the name on the door was the same and I looked just like he did at my age.

I had prepared the old punishment book to show to the Head.  In the privacy of my chambers, I showed the miscreant the entry I marked.  There, in my cousin's neat hand, was the report of him found with scabrous material for which he had received six-of-the-best and promised never to bring such filth into the school's precincts ever again.  Of course, it was signed by him.  He had two choices.  The first was to be a man and a master and immediately demand that I return his magazine.  He did not do this and instead he turned pale like he had when he was a student and my cousin was the Headboy.  "Please…." he begged evidently still the coward.

"There is another way." I said softy after a most pregnant pause pointing to my cane in its place in the corner.  He shuddered frozen in place.  I watched him for more than a minute.  Fear and fascination was on his face.  Then I spoke with as much authority that I could muster.  "Strip and get into position.  You know the drill, boy."  He remained frozen as I stepped over and picked up my cane.  He flinched when I cut the air with it.  "Strip", I repeated, "Howlett.  NOW!"

I watched, fascinated, as he removed his jacket and placed it neatly on the chair.  My cock was also responding.  He opened his belt and trousers and started to take then off and found his shoes were an obstacle so he removed them first and then his trousers.  He moved to the desk and I barked: "Everything, boy!"  Slowly he removed his tie, shirt and vest as I watched.  He continued to the desk and leaned over.  Smiling, I lowered his pants to his ankles and he stepped out of them when I tapped his foot.  His nakedness was emphasized by his black knee high socks so that he appeared to float.

"Position.  Remember, don't get up until I tell you to – unless you want extras."  My boy, Howlett, dutifully bent over and grabbed the far side of my desk.  I took my position and let him feel the cane as I made sure I was in proper position.  I raised my cane and brought it back down on target with all the skill I had.  Just like he had when he was my age and younger he cried out.  The echos faded before the track marks formed.  I had to reach into my own trousers and pants to adjust myself.  I waited a full minute before giving him the second cut and another minute for the third.

"Halfway, boy." I said and dashed into my bedroom to fetch something before resuming.  Cut four was just as straight as the first three and the nancy boy was crying.  I made sure that the fifth would really hurt by putting it on the crease at the bum/thigh meeting.  The sixth cut I placed diagonally to make a proper gate.  I had removed my blazer before starting and now I quickly undid my belt and trousers and pulled out my hard shaft.  I quickly covered it with the petroleum jelly and, most considerately, smeared some on my boy's hole.  A finger, then several slipped into the hot cavity easily but I did not let them remain very long.  I positioned my cock on his hole and grabbed the crying boy by the hips and shoved in.  He docilely kept his hands on the far side of the desk as I shagged him thoroughly blasting my babymakers deep into his arse.  I was very hot so I continued shagging until I climaxed a second time.  Then I told him to get dressed and leave.  He did without even asking for his magazine but thanking me like he did my cousin when he was a student.

This was not the best fuck I ever had but it was most satisfying.  I could hardly sleep that night because I was still flying having totally dominated an adult (even though he was a faggot).  I was already looking forward to the next time.

The next afternoon, another truth was revealed to me as I listened Howlett's soporific droning.  It was not that his lecture contained a great truth but that I could see (in my mind's eye) through his gown, trousers and pants the perfect gate that I made on his bottom.  It was then that I realized that swishing older men was most satisfying.

End of Part 1.  Go to Part 2

© Copyright A.I.L., April 7, 2007

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