When I was at school we had a bearded gatekeeper who I really fancied. He was about forty years old wirily built and had the right to cane any boy he caught outside the gates after eight-o-clock. The few boys who had experienced a caning at his hands were able to show off the most incredible stripes which wrapped right round both cheeks of their arses displaying an amazing range of colours from dark purple to pink, yellow, brown and red. It was reckoned that Henry, (that was his name), used his caning opportunities to revenge his class on us rich kids. He usually wore a dark porters uniform but when he caned anyone he took off his jacket so as to be able to swing his cane without any impediment. Sometimes during a hot summer afternoon he could be seen working in his lodge garden clad only in an old pair of rugger shorts and it was after seeing him there and admiring his splendidly hairy chest and legs that I decided I would have to get myself caned by him.
I decided to wait for a really hot evening when he would be sure to be working in his garden in his old shorts to get myself caught outside the school gates after eight. Such an evening soon presented itself and I saw Henry working away in his garden. I slipped unseen through the still open school gates and waited until a quarter past eight.... then I crawled along the outside of Henrys garden wall as if I was trying to reach the gates without being seen, and when I reached the dustbins by his back gate I deliberately knocked the lid off one of them making a loud clatter, I then ran (but not too fast!) towards the school gate. As I had intended Henry saw me and with surprising agility jumped over the low wall of his garden and grabbed me with his earthy right hand.
Got yer... young fellow!! Now you know that Its my duty to cane you dont you?
Yes ... Henry, I suppose it is... I answered with my most captivating smile.
Well come into the lodge where I keep my canes and well get it over and done with!
And he began to pull me towards the lodge ... I was by now very excited and the close proximity of this simple but very masculine man gave rise to considerable movement in my groin! I allowed myself to be led without resistance into the large kitchen on the ground floor of the lodge enjoying the exciting aroma of fresh man sweat that emanated from Henry. I knew that it was in this large kitchen that Henry caned boys whom he had stretch across the old fashioned kitchen table. In the corner nearest the window stood a tall basket which probably should have been an umbrella stand ... but instead of umbrellas it contained about half a dozen viscious-looking canes!!
Henry had never married and lived in the lodge on his own ... a good sign Id always thought, but I didnt really know how to take advantage of the apparently favourable situation!
As Im sure you know, Ill be giving you six of the best, so the sooner you bend over my kitchen table the better! growled Henry.
Just a moment, Henry I managed to blurt out. I know that Ive got to be caned ... but first I want to ask you something
O. K. lad, Ill let you express the condemned mans last request. He said with a very _s_e_x_y and totally unexpected smile!
Well....? I continued, I have something to confess before you thrash me.... I didnt actually go anywhere this evening... I wanted you to catch me.... because I want to be caned by you! So to make the punishment effective I think we need to make a few changes to your normal routine..... What do you think?
Well, said Henry..... if you put it like that I suppose its my duty to give you an extra severe lesson.... we could begin by having you remove your trousers and pants!
Ill certainly oblige you in that... but I want to strike another bargain.... I know that you are really only allowed to give us boys six..... but if you we both strip naked.... you could give me twelve.... and we could seal our agreement with action of another kind.... if you like.
Henrys eyes sparkled and he smiled again, showing his white teeth contrasted against his dark beard.
I certainly would like.... but I must warn you that Ill give all twelve strokes as hard as I can.... and anything that happens afterwards must be a secret... and to make sure we are agreed on all points I want you to give me six strokes before we start as a kind of proof of our agreement.
I could hardly believe my ears, this butch guy was asking me to cane him!!!! But I suppose he thought that a nice set of bruises would make it impossible for me to press any claims of abuse. In any case, never in my wildest wankings had I imagined Id ever have the chance of using the cane on such an attractive macho guy!
Done! I said with increasing enthusiasm.
Well lets get rid of our clothes. Said Henry, pushing down his shorts and revealing a large semi-stiff _c_o_c_k_ to my greedy gaze. I rapidly fumbled with my summer uniform but was soon as naked as the guy before me. Henry selected a cane from the basket in the corner and flexed it across his hairy chest.... before handing it to me saying.
I want you to thrash me as hard as you can..... my striped arse seals our agreement!
Very well, Henry, I said assuming an authoritative tone Bend over the kitchen table!
Henry complied presenting me with a taught white arse covered with dark brown hairs. I raised the cane and brought it down with all my force on the target area. Henry threw back his head and gasped.... clearly even though this was the first time Id wielded a cane it was coming to me naturally. I waited several seconds to let Henry savour the pain Id so successfully inflicted. I watched a classic tram line rapidly rise into a scarlet welt that covered both cheeks very neatly.
My second stroke was as powerful and Henry gave a little grunt of appreciation. I was really enjoying myself but I was also impatient to be on the receiving end. By the sixth stroke Henrys arse was quite a sight. I felt Id done a pretty good job. He eased himself up from the table and gently felt the raised welts on his bum.
Youll make a good prefect, lad.... but now give me the cane and get yourself bent over the table ready for your dose!
As I got into position I noticed that Henrys _c_o_c_k_ was now standing proudly to attention.... I wondered if it was from the excitement of being caned or from the anticipation of caning me. I stretched myself across the table and braced myself for the coming ordeal. I had been caned pretty frequently both by prefects and masters.... but nothing could have prepared me for the agony of that first stroke. Henry took a little run up and with a kind of skip lashed the cane into my backside.... I thought I was in another world.... I heard the crack of cane on flesh but the pain!!!!! or should I say the pleasure?.... perhaps the best word is the sensation! I floated in a universe of fire and pre-orgasmic tension which was almost humanly unbearable..... not for the pain but for the intensity of the sensation. I believe I yelled... but I cant be sure... all I know is that I longed for the next stroke as if it could resolve all the problems of existence. Henry timed each stroke to obtain the maximum effect and as I bucked and screamed I was ever nearer to having a devastating orgasm ... but somehow I managed to hang on ( its said that a thrashing after an orgasm is even more painful.... but perhaps its just a different perception of pain). I managed to glance over my shoulder after the third stroke and saw that Henry was very excited and a thread of pre-cum was already oozing from his splendid member. By the sixth stroke I felt sure I must be bleeding but perhaps the liquid I felt running down my thighs was only sweat produced by the pain fear and excitement.
As I watched the coordinated movement of the muscular hairy man who was caning me as hard as he could I felt that I would never have such an intense experience again. By the eighth stroke I was pushing my devastated arse out to meet each stroke (and to provoke other feelings in my tormentor!!)
After the twelfth stroke Henry threw down the cane and before I knew what was happening I felt his hairy body over me as something very large and hot forced its way up my arse.... the delicious sensation didnt last long because I started to come, with violent squirts all over the kitchen floor and my sphincter muscles milked Henrys appendage as he too came, thrusting into me and howling louder than I had done during my caning!!
When he had withdrawn his wilting member from my ravaged arse we turned face to face and without saying a word intertwined our tongues in a long suffocating kiss as we fondled each others welted buttocks.
Before getting dressed I promised Henry that I would be tripping over his dustbins after hours again, as soon as my bum had recovered enough to receive some more loving attention from one of his canes.... That night my arse was very painful but I also had a permanent erection and wanked five or six times before I finally fell asleep (on my stomach!) dreaming of my hairy tormentor.