[Fiction] A willing boy's first whipping.

[m55uk4younger]

A willing boy's first whipping. Chapter one.


I was fifty when I was fortunate enough to be taken on as a teaching assistant at a boys private school which was for young boys aged eleven to eighteen.
Our school had 160 boys of all ages and most of them were boarders.

I loved my work because I had always loved young teen boys. I would watch them develop from eleven year old innocents until at around their fifteen birthday they would suddenly become infinitely desirable. Not only that, but their hormones had started working years before and made many of them incredibly and intensely sexually aware.

At the end of the summer term it came about that three of the boys had no parents coming home from abroad, and the head master asked me if I would stay on and look after these lads for a couple of weeks until the parents arrived.
I would be paid extra of course and would only be expected to look after them by day, while the housekeeper would stay on as housemother to see to their domestic needs. For me this meant a sort of camping holiday with the boys, doing all the boys sports together, and being the summer spending a lot of time lazing around the school swimming pool.

So this story is about those boys, and I will deal with one particular boy first. He was a boy that I had lusted after as I watched him in his P.E. gear.
Thin white cotton shorts with nothing underneath as this was the school rule
for gym lessons. Then, if it was warm I would have them strip to the waist and be barefoot for good measure.
Best of all though was during swimming, when clad only in the tiny school briefs the school had adopted. These we told the parents were made so that they fitted any boy in that they were two little triangles tied across the hips with a bit of cord through some lacing eyes. As our oldest boys were eighteen and did not even have the fronts lined and as they were thin shiny material they did not leave a lot to the imagination when wet!
The boys seemed to delight in wearing them brief with the sides bunched on each hip leaving all those folds in the front pouch area for the imagination to run riot.

He was physically perfect. Just forming his smooth young muscles and with velvety smooth skin. His tummy a perfect flat smooth surface around his neat little navel and when he climbed out of the pool his briefs would be so low on his tummy that his groin lines almost met above the top hem, literally only just above his penis. Piercing blue eyes, a tousled mop of fair hair, and the most gorgeous tan from a lot of time around the pool.
I got an erection just looking at him!

But all of this is immaterial to the story! Because I had observed this boy, whose name I remember was John, would often leave on his own and slip into the nearby woods which adjoined the sports field. This left me, and the two other boys, playing alone on the field. After I had seen him do this on several occasions.
I decided that I must follow him quietly and see what he was up to.
One day he was away a full hour and I decided that the next time would be my chance.

So greatly intrigued, and I have to say with mounting excitement because I suspected he was on some sort of sexual mission, I followed him around ten minutes after he had left the field. It was a hot summers day and I followed the tracks he had made through the knee high bracken. The track led directly, as I suspected it might, to an old wooden hut that in days gone by had been used for summer camping but was now abandoned. For all that it was in good condition and its single window had no broken glass and the door was solid and still well hung on its hinges.

I approached slowly and quietly and went to the window to carefully look in only to find that the window had been deliberately blocked by what looked like an old blanket from inside. I crept along the side wall and finally found a small knot hole through which I could see most of the interior despite the holes small size.

I felt a surge of elation and my cock became rigid immediately. There in front of me in the centre of the shed, was John. He had stripped naked but for a tiny loin cloth which he appeared to have made himself from white cotton hankerchief material, with a cord between the legs and around the waist g-string style. The loin cloth was just forming a small loose pouch around his genitals and I could see his erection pushing the folds of cloth rigidly forward. But more that that, what really excited me was that he had strung himself up by his wrists to an overhead beam. Around each slender wrist was a lasso of soft rope. He had clearly stood on a box to get his wrists into prepared slip loops and then kicked the box away, which now lay some distance from his feet. His toes were only just touching the ground. He was struggling to take some weight on his legs, and his body was squirming, writhing and contorting as he hung so nearly naked and utterly delectably before me. A sheen of sweat was beginning to cover his face although he can only have been there for a few minutes. His chest and tummy were shiny with his efforts as he struggled to ease some of the pain from his wrists, and get an arm free to loosen his bonds.

Quietly I rose, went to the door, and pushed on it. He had blocked something against it but with a good push I was in and stood before him with my hands on my hips. Well well John, what do you think you are doing I asked. Oh sir, please sir, get me down. There were two men that set on me and tied me up like this. Please sir, let me down.

Now then John, that will not do I told him. I know you tied yourself up like that, and I am going to take a few photos of you incase you ever deny it. I don't think you would like anyone to see the pictures, would you? So saying I stood back and slipped my camera phone out of my pocket, taking photos from all angles of the writhing sweating teen boy. I particularly liked the back view, completely naked but for the thin string running from between his legs to the string around his waist. His wonderful tan contrasting with his
small white buttocks where his bikini swimmers had covered him. His back was a lovely concave curve above the string of his loin cloth as he struggled to gain some support from his toes and his shoulder blades were working too and fro under his velvety smooth tanned skin. I finished taking my photos and went back to face him.

Now look John, just tell me what you are thinking and why you have tied yourself up like this. I reached forward and in a friendly gesture tousled the boys fair hair, then let my hands hold him just under his armpits while I looked into his anguished eyes. Look boy, I promise you this is not all that unusual behaviour for a boy of your age so don't be embarrased.
Lets talk about it and see what we can do for you.
Yes sir, alright, I know I did it.
It is only a game but I imagine that I am captured and tied up by cruel men who punish me, whipping me and torturing me.
Yes John, I know that many boys have these fantasies but how far has your fantasy ever gone. Have you ever actually been whipped when you are tied like this.
Well only very slightly sir, by James. He and I played tieing up and made a whip to try out, but only very gently. So I always imagine being whipped in front of the men who are holding me captive. I have always imagined myself strung up and taking the pain bravely. I have wondered what it would be like and it makes me excited even though it must hurt a lot.
At this point I let my hands gently slide down each side of his body to his hips, and then one hand to his rigid erection so beautifully outlined in his skimpy little loin cloth.
He shuddered and pushed his straining body forward against my hand and then whispered the words I never thought I would hearfrom a young boy.
Please sir, do you think as I have been very naughty I should be whipped now.
Sir, I think I deserve to be whipped.
Oh yes John, I agree with you, but first, no one must ever know what has happened here and what you have done to yourself.
I will give you a whipping right now so you know what it is like and if at any time you feel like more I will arrange for you to visit my house where I have a special room set up for men who have the same fantasies as you. You see, you will not be the first to be whipped in my dungeon!.
Wow sir, can I really do that please?,
came his reply. I told him then that I thought maybe after I had dealt with him now, that he may not want to visit me, and with that, prepared to carry out the punishment that he so clearly wanted.

I am going to whip you with my doubled belt, six lashes across that little white backside of yours I told him.

I stood in front of him with mounting excitement as I slowly undid my shirt and pulled it off over my head. That will give me more freedom to swing my arms I told him. Also, I think, so you are held a little tighter that your legs need spreading a bit to a true spreadeagle, and I picked up a short length of discarded old timber from one end of the shed. I need some more cord I told the boy who was watching my every move. Sir, in that rucksack with my clothes there is some more cord said this delightful boy. I went to his rucksack and unzipped the top to find inside a collection of cords from which I chose a couple of lengths. Going onto my knees before John, I tied one ankle firmly to one end of the wood. Right boy, spread those legs I told him. He was already on his toes so this had the effect of virtually hanging him from his wrists. As he struggled so his wrist rope loops stretched a bit more and he finished up with just his tip toes giving a tiny bit of support.
His little young body was now stretched tight, tummy pulled in tight and that delicious sheen of sweat across his chest.

Are you going to strip off my g-string he asked me. No John, I like the look of you as you are. I can see your excitement easily enough, and I gently felt his erection where it stuck rigidly out into the folds of the thin cotton material of his home made loin cloth. He pushed his body against my hand again as best he could in his suspended state so I felt his little shaft for a few moments, stroking it up and down until he was obviously getting ready to orgasm.
I realised that now he was ready for his ordeal to come.

He watched me then as I removed my belt, double it in my hand and swished it through the air. My trousers were now loose around my waist, so I told John that I had better take them off. My sandals followed and I now stood wearing only my boxer briefs that I always wore for hiding my often excited erections from the boys. I went to one side of the boy, and enjoyed watching his expression as his head swung to watch me.

I did not spare him and landed the first hard lash across his white buttocks and got a small gasp in response. I landed the second lash just below the first and enjoyed watching his body jerking in his bonds. Three, four, five and now the boy was crying gently. One more John, are you ready? Yes sir, please sir, and I swung the hardest blow low across his now red striped bottom. I dropped the belt, went to stand in front of him and gently ruffled his hair, pulling his head against my chest and pressing my body against his until I could feel his erection pushing against mine. We stood like that for about a minute as I ran my hands gently up and down his smooth young back before he surprised me again.

He pulled his head back from my chest, and looking at me with those lovely clear blue eyes, his face now stained with tears, this beautiful angelic boy asked for more!

Please sir, I think I deserve more than six for being so naughty. Sir, in the bottom of that bag is the home made whip I mentioned that James and I made to try on each other but he could not come today which is why I am alone. Reluctantly I let go of the boy and went to the bag and sure enough, in the bottom was a short length of broom handle with nine leather boot laces fastened to the base of it with pvc tape. The laces were just over a half metre long and made a wonderful whip. I ran them over my hand and then noticed that just three of the laces had been longer and were now knotted about every two centimetres. I returned to stand in front of John holding the whip.
He was still sweating and from his slight writhing it was obvious that his arms were giving him quite a bit of pain. John, these knots are going to really hurt you I told him, in fact, they could cut you. Sir, I deserve the punishment, please sir, please do it to me. I stood away again to one side and hefted the whip in my hand, and the bound and helpless but willing boy watched my every move. His lovely naked body with just the string and cotton loin cloth was waiting for his own home made whip. I lashed it hard accross his buttocks and he cried out in shock. I gave him three more and stopped then went to stand in front of him again. Now I undid the knot of the stringholding his only covering and his smooth hairless penis sprung out. I started to wank him then and he immediately climaxed, going rigid and giving a small high pitched cry as he hung before me. He slowly went soft in my hand and I assumed we had finished our little game.

Then as I held his perspiring anguished young head against my chest again he looked up at me and said, please give me the last six strokes please sir, I know I deserve it. John, that is too much I told him but as my hand stroked down that smooth tummy to find his soft little penis I was amazed at what I found!
It was no longer soft, but rapidly rising again obviously at the thought of yet another whipping to come. Such is the wonderful quick response of a teen boy! I ruffled his hair again, stroking his firm back and over his now red whealed buttocks. His little voice came again,
"Sir, three on my back and three over my chest and tummy he whispered. I stood back from him then, marvelling again at my new little masochistic boy.
So I prepared to do his bidding. The first stroke was across his shoulders and he bucked and cried out. The Second wrapped around his mid back and ribs and he gave an anguished cry, so the third was low around his waist to wrap viciously around his midriff. I watched as he writhed in pain, tugging at his wrist bonds and kicking up his bound splayed legs into the air so that he was for a moment fully suspended.
Then it was time for his frontal whipping!
The first, hard across his chest caused him to give a small scream of agony and a red stripe appeared as if by magic. I struck again, with no mercy around his midriff and watched the tails of the whip curl around his already sore back.

Sir, please sir, that's enough he called out as he writhed and struggled in pain.
Oh no John, you asked for six and you have one more to come.
No mercy from me when you have already asked for it.
I leaned forward, another hair tousling, a gentle feel of his erection now twitching and hard and he was as ready as he ever would be. For good measure though, I stood in front of him and gently kissed his brow, then his lips to which he responded with some passion, while whimpering softly.

Again I took my stance, swung the whip and landed it across his midriff just above that straining penis. He cried out in agony as the red stripe rose across that smooth tanned skin, but it was over. He gasped, crying, writhing and filling me with desire to hold him. I released his legs, then his arms, and as he came free he flung his arms around my neck and hugged his naked body to me, pressing his rigid penis against my near to bursting briefs. Then, dropping his hands to my briefs he pushed them down and started to fondle and work my cock which responded almost immediately with spurt after spurt of cum over the tortured naked body of this wonderful boy.

I knew now that I was going to have some wonderful sessions with this youngster when I got him over to my house. Particularly, as he seemed to like the feeling of having his hands strung above his head. I imagined him bound by his wrists to my large wooden christian cross that was mounted in my basement. I had perfected this apparatus so that I would lift the victim up to balance on a tiny little platform on the centre post. He would then first have his wrists fastened with soft leather bindings, while he stood on a tiny platform.



Next the dungeon!

Your thoughts on how the story should go?
Should his friends also visit, alone or together?

Sir.