Date: Wed, 9 Mar 2011 15:27:23 +0000 From: timo diego Subject: A Willing Masochist's Initiantion Chapter One My name is Timo and although I am now middle aged, this is my story of how sexual awakening started for me. When I had just turned thirteen I was sent to a private boarding school for boys. Boys would stay there until aged eighteen and all exams had been taken. At that school, in those days juniors were expected to run errands for the senior boys, and the older boys were even authorised to punish juniors if we misbehaved. As you can imagine, this led to seniors often taking advantage of us youngsters. I had fairish hair, clear blue eyes, a soft and pretty boyish face and a slim body just beginning to form muscle so that my tummy was flat and firm, smooth skin with the softest of down forming down my back with a promise of things to come, and all over bar a white stripe where my speedo came I was a beautiful honey tanned colour due to many hours spent outdoors, usually swimming with my mates at the quayside. Importantly to this story I should explain to you here that from an early age (I suspect like many other boys) I fantasised about being captured, punished, and made a slave, and more especially because we were brought up expected to look up to and do the bidding of senior boys. I fantasised about made to strip naked or just stand before them with a tiny loincloth and then being strung up by them with my hands above my head, finally being whipped while the watching men and older boys watched me struggling. While I had these fantasies I would wank off and as time went on I would go further, stripping naked and tieing my legs, then I would tie my hands behind me leaving just enough slack for me to reach to wank myself. So as you can now imagine, I was absolutely ripe to meet an older person who could take advantage of all this. I had only been at the school for a couple of weeks before I was aware that one of the senior boys was taking a great interest in me. He would often be supervising at bath time or sports events, and almost always when we were having swimming periods. For swimming we all wore a school pattern of briefs, they tied on each hip with lacing eyelets so that they would fit any size of boy or this was the reason given but we all reckoned that it was because they made us look sexy and they had been designed by a randy old master! They were indeed small triangles of blue cotton material, and many especially those for us younger boys, were unlined so when wet clung to pretty well everything underneath. Many of them had broken strings on the hips and had been re-threaded so when tight they pulled the sides together really brief. I liked this, and I was aware that it showed the maximum bare midriff possible so that the lines each side of my flat smooth tummy almost met where the top of them passed just above my genitals. After diving in I would check that they were as low as possible and pretend that I had not noticed. This soon paid off and the senior boy I had noticed told me he had a small job for me in his room where, he said, the window needed cleaning! When I attended he was there alone and chatted in a friendly way to me. He told me his name was Juan Gomez and when we were alone I could call him Juan. This was unusual because normally we used only our family names to address each other. I was therefore normally Diego but he now often called me Timo. "I have noticed that you swim very well Timo, you look like a real water baby and obviously enjoy it. I wondered if you would like to come out with me for the long weekend that is coming up in a couple of weeks, when I am going to my parents log cabin to do some fishing and I could take you to do my chores, you could do cooking and cleaning, or that is what I would claim. What do you say?" I was very flattered because I hero worshipped this mature boy and thought he was marvellous. In other words I had a real crush on him and the thought of just him and me was really exciting. "You will be totally beholden to me Timo, you realise that I hope, and you will be in effect my slave boy. You will get plenty of swimming as well, and because we will be completely along you will not need to bring any of those pesky briefs because we will swim naked. Does that worry you boy? "No Juan, you see me in the bath often enough and with both of us naked it will be pretty cool." "Good boy Timo, during the days you will wear just a loin cloth like a Tarzan boy that I will provide, and as I said, for swimming and of course for sleeping you will be naked. We have a couple of weeks to go and it would be best if you don't mention it to your friends who might be jealous, or think other reasons." The two weeks flew by, and whenever I could I posed in front of Juan. In the swimming pool I got an erection just watching him watching me and had to dive in so he did not see the tent in my briefs. On the last day he gave me instructions as to what to pack and needless to say it was not very much but I put in spare clothes and pyjamas to make it seem normal to the other boys. On the Friday night of the long weekend he told me to go down to the bus depot and get on the bus to a little village about ten miles away on the edge of the forest. He would be on the same bus and would tell me when to get off. We would have a mile to walk on a wooded trail to get to the cabin. When we alighted we both had to carry a pack of stores as well as our kit but it all went well, and we were soon alone and trecking up through the woods to find the delightful cabin alongside the lake. It was completely deserted and once Juan had unlocked the door we went in and lit up a wood burning stove because although it was nice and warm anyway it made it, as he put it, more cosy. "Now I told you Timo, you would wear appropriate clothing for being my slave and he pulled out from his bag a small chamois leather loin cloth. There was a front flap, a narrow piece to hold my cock and go between my legs, and another small flap at the back. It tied low around my hips, being secured on one side with a small knot. Before I had it in place and was standing naked with Juan watching I became almost erect and of course tried to hide it from him. "Timo, stop, put your hands on your head and face me. Now boy, now." I did as he said and turned towards him with it untied on the side and then, as my erection became totally rigid the cloth fell away and I was fully exposed to him. "Timo, I like you more and more. Now you are naked so come on, let us swim for a bit and you can put that loin cloth on for supper. After supper I have some videos to show you that I hope you will find exciting. If you do then we are going to have quite a good three days!" So we swam, and fooled around in the water and then came back to the cabin, dripping and laughing and both buck naked. It was the first time I had seen Juan naked and I was mightily impressed with his bush of black pubic hair and the size of his uncut penis which even after the cold water was pretty impressive to me. My own tackle had shrunk with the cold a bit but as soon as we were back in the warm it went to its usual thirteen year boy size which I have been told was actually pretty impressive. "Now I want you in that loin cloth Timo, and then I want you to cook up some sausages from the fridge which we will have with fresh bread and butter." I stood naked before Juan and he picked up the little loin cloth. "Come on boy, hands on head" was his order. As I stood passively in front of him he tied the little chamois outfit in place and I had to admit it was really sexy. Then as I started over to prepare the meal Juan came up behind me and suddenly put his arms around my naked upper torso, before dropping his hands to feel my growing cock. I noticed that he had put on a pair of black swim trunks and looked wonderful in them. "Good boy, you are quite a stunner, and I can hardly wait for you to see the videos, so let's be having that supper." After supper was cleared we went into the main room to sit in front of a fairly large screen ready for the videos. "I think I am fairly good at judging people" Juan said, "and I am guessing you will like what you see in a minute, but if you do not I want you to say so and we will forget all about it, because you may find some of the scenes a bit violent. It is up to you boy." With the lights off the first video started and I gasped because the first scene was a boy of about my age. He was naked and his wrists were tied tightly and pulled up to an overhead beam. He was pulling at his bonds to try and get free but as he did so, a man wearing black trunks like Juan came in holding a multi tailed whip which he swished too and fro so the boy could hear the noise. The boy had been there a while because he had a sheen of perspiration covering his body then when the man came in he turned to watch him. Suddenly the boy stopped his struggling and stood still, his bound wrists held aloft and his legs slightly apart. As the man approached and the boy watched him the camera focused on his hairless penis which rose to full erection dramatically. The man took up position beside him and fondled his excitement. "Are you ready for your punishment boy." "Yes sir, please sir I deserve to be whipped. Please whip me and make me suffer." "Right boy, suffer you will. I want you to count each stroke aloud to me. If you miss one, you get it again and in fact if you fail to count properly we will go back to the beginning and start again." The boy stood still, his sturdy legs braced slightly apart, his body smooth and hairless apart from the few sparse hairs around the base of his cock which was now so firm it was almost touching his smooth flat tummy. "Brace yourself then boy, the sentence for you today is twenty lashes." And so it started, the boy silent except for shouting out the numbers, writhing in obvious pain but still wonderfully erect and therefore seeming to be sexually enjoying it. After ten strokes the man paused and ruffled the sweating boys hair before leaning over him and giving him a long lingering kiss while his hands smoothed down his torso. "What do you think of that Timo?" asked Juan as he slid an arm around me. "It is fantastic Juan, fantastic. Juan, can you do that to me, please Juan, please. Because I think I could take it even better than that boy." "Timo, you have made my day. We will watch the rest of this boy's punishment and then you had better prepare yourself for your own ordeal." "Yes master, yes Juan. I will not let you down." I said. As the boy in the video started to be whipped again Juan's hand was inside my soft chamois loin cloth and gently caressing my urgent raging erection. I snuggled up against him, my new master, in anticipation, my excitement mounting but with the dread at what had been promised to me very much in my mind. We watched together as the boy on the video hung from his bound wrists, eleven, twelve, thirteen, the clear young voice called out as he writhed and squirmed hanging from his bound wrists. Occasionally the man paused, watching as the boy struggled to take the pain, then, standing back, another stroke and the cry of fourteen, fifteen, until finally, at the twentieth stroke the man laid down his whip and went over to release the boy. Having untied his arms he hugged the still amazingly erect youngster to him, ruffled his hair and kissed him and then scooped him up and carried him out of the picture. "It is your time now Timo, come with me to where I am going to punish you." And Juan led me away with a firm hand behind my neck to where he had already prepared for the scene. Out in the open on the boardwalk of the cabin in the warm summer climate of our island he had prepared it well. On a table to one side he had placed a multi tailed whip, and some lengths of cord which he led me over to show me. He turned me round to face him, placing a hand on each of my shoulders and looking into my eyes. "If you are willing and strong enough to want me to punish you boy, you must hold out your hands for me to bind them." With mounting excitement I did as I was told, and felt a growing thrill of anticipation as the thin cord was wrapped around my wrists, like the many times I had done it to myself but this time I knew that there would be no escape. Juan trussed my wrists, cinched them tightly and then fastened a rope hanging from a hook above that he had placed ready and quickly pulled my hands tightly above my head. He stood back and savoured the sight of me, a beautiful and willing boy, helpless and awaiting his punishment. He leant forward and undid the hip tie on my loin cloth which fell away to leave me naked, but wonderfully and proudly erect as my hairless rampant penis twitched and throbbed in anticipation. For a moment he caressed my straining rod, but I implored him to leave it because I could feel myself so imminently cumming that I feared for the will power that I would soon be needing to withstand the pain of punishment. Juan stood back and looked at me. A bound and beautiful thirteen year old, fearfully but willingly awaiting his agreed punishment. What more could he wish for as he stood clad only in his black trunks, and reaching for his whip. I would like some feed back because there have not been many bondage scenes recently and yet they have their place. Timo in this story was so enjoying the scene and in the next chapters will continue to do so. Please let me have ideas for future chapters and especially your ideas on how I should continue. Timo Diego.