Date: Mon, 12 Nov 2018 19:03:12 -0500 From: Daniel1989a Subject: Watching Jeremy Watching Jeremy My life at 45 revolved around a few things, maintaining my house and my investments, both of which made it possible for me to not need to work and checking out boys online and in my neighborhood. I had lived in this same house since I was born and after my parents died, it as well as the modest fortune they had amassed became mine. I had never married, never even been interested in girls, other than just enough to keep my boy loving a secret. Now with my parents gone I no longer had anyone to fear. I had a few experiences with teenaged boys, but nothing like what was to come. The house directly opposite mine had changed hands many times, but for the last 10 years, it had been occupied by a single mother and her son. I knew the Mother, Jane, enough to exchange a few words and had watched her son, Jeremy, grow from a small cute kid into what now interested me, a very hot 14 year old. Jeremy had always been a shy kid and that did not change as he became a teenager. In 10 years I had only exchanged a few words with him, but in the last year or two, I had observed him changing. He was still shy as far as I could tell and I was lucky if he even raised his hand when he noticed me. He had grown from a small kid into now, a dark-haired boy of about 5'6". He always wore oversized t-shirts and baggy shorts which made it difficult to gauge his weight and wore his hair, in my opinion, much too long. I knew his mother thought the same, as I had overheard a few arguments on this topic, as well as a few about his graphic t-shirts. A little over a year ago I had watched as Jane had converted their garage into an exercise room, complete with a full weight set, and although I had never seen her use it, Jeremy seemed to spend every spare moment there. It was a bit frustrating for me, as he always closed the garage door, completely cutting off my view, a view I had would have loved to watch. During the last year, I had observed the comings and goings at Jeremy's house with a passion, hoping for any chance to see him wearing less clothing, but his routine was almost always the same. During the school year, he was off early in the morning and returned around 3 pm, went into his house and moments later came back out dressed in shorts and a t-shirt, then headed into the garage and closed the door. Most days he was in the garage for around 90 minutes, then emerged and went into the house and shortly after that his Mother arrived home. From time to time Jeremy would still be working out when his Mother got home and this had caused a few arguments as well, causing Jane to 3 times threaten to take the gym equipment and sell it. That threat had worked, because since then I had never seen Jeremy still in the garage when she got home. It went on like that for quite some time, but gradually I noticed that there were the occasional days that Jane arrived much later and a few where she did not get back until the next day. It was those days where she was gone all night that I noticed Jeremy changing his routine. He would arrive home from school at the same time and enter his house, but when he emerged and headed to the garage, instead of shorts and an expensive t-shirt he was always wearing old tattered t-shirts and track pants, and instead of 90 minutes, he was spending much more time in the garage, over 2 hours. I figured he was using those days to put in an extra hard workout and even from across the street, I had on occasion heard him groaning from the effort. I began being able to anticipate the days that Jane would be gone for the entire night and once I was much more certain I decided to do a little legwork. Once Jeremey was in the garage I started doing work near the end of my driveway, nothing necessary, just something that got me closer to his garage and I definitely heard the sounds of him working hard. The next day, although I knew it was not a day that Jane would be gone all night, I carefully crossed the street with a newspaper in my hand, one I knew got delivered to their house that I could pull out in case of any questions. I looked around and walked up their driveway, my heart racing as the closer I got the louder Jeremy's sounds became. I was about to walk to the side of the garage, where I knew there was a window, but I heard a car coming and instead retreated back to my property. The next day, I grabbed the exact same newspaper and this time headed to the side of the garage and carefully peered through the window to see Jeremy on his back on the weight bench doing bench presses. He was wearing one of his oversized expensive t-shirts but from this close, I could see his muscles working underneath it. The sight thrilled me and I watched for a few minutes before again retreating to my property. The next day I knew was one of the days that Jane was away and like clockwork after school, Jeremy entered his house and came out wearing an old tattered t-shirt, making me wonder how many he owned, and track pants. After he entered the garage and closed the door, I waited a good 20 minutes then walked down my driveway and across the street. I was halfway up his driveway when I heard his voice and as I got closer I made out a few words that sounded like, "No, stop, please." I took a few more steps until I was just outside the garage door and this time heard clearly, "Stop, please, stop....you can't." My body froze, unsure of why he would be talking like that and I wondered if he was on his phone, but a few seconds later I heard, "Please, you can't." His voice was a bit louder and there was more emotion this time. I looked back at my house and almost left but then I heard, "PLEASE, I'll do anything." My pace quickened, now concerned that Jeremy was in trouble, but what I saw through the window made my heart pound. It took some time to take the image in, but after shaking my head and looking carefully I felt my cock harden instantly. Jeremy was laying on his back on the weight bench wearing the tattered t-shirt and track pants but he had attached two leather ankle cuffs to the legs of the bench and had strapped his ankles into them. I could see clearly that these were good solid cuffs and must have cost a decent amount of money, they had both buckles and a ring for a small padlock, which was attached to both right now. It must have been awkward to accomplish as his legs were spread as wide as the legs supporting the bench. I marveled at his ingenuity and as I followed his body with my eyes, I saw that he had attached an equally expensive cuff to the legs supporting the head of the bench and had securely strapped his right wrist into it and like the ones on his ankles, had attached a small padlock. The cuffs themselves were attached to the weight bench legs with thick secure chains, these were not toys, this was serious gear. As I looked more closely I saw that his legs were spread wide and secure, his right wrist was pulled up behind his head and just as secure and that he had attached a thick leather strap around the leg on the left side of the bench and right now he had his left hand looped through it. I saw that he could easily free his left wrist, but what excited me was that he was pretending he couldn't and he was even wearing a blindfold. I watched as he struggled against his bonds fiercely, trying to free his ankles or even get his legs closer together, but he had done a great job and until he set himself free, his legs were spread wide as could be. I almost jumped back, startled as I heard, "Please, let me go. Stop! Who are you? What do you want?" As he said those words he struggled even harder and I could see his muscles working under his tattered t-shirt as he again pulled at his bonds. I almost stepped away again as I saw Jeremy unlooping his left wrist, thinking he might get up, but seeing how tightly the cuffs were attached, it would easily take him a few minutes to get free. When his left wrist was free he pushed the blindfold up just enough so that he could see as he looked towards the bench support near his left side. I saw a glitter and realized he was looking at the key for the cuffs, safely attached to the weight bench leg near his left wrist. He began to lift the left part of his torso off the bench again, his left wrist loosely looped his wrist through the leather strap as I heard, "What are you doing? Stop!. You can't. Please!" I heard the faint sound of fabric tearing and wondered what was happening, but as I watched, his pleas got louder and more serious, "Quit it, leave me alone, let me go! Who are you? Why are you doing this?" I soon discovered why he brought an old tattered t-shirt. He had somehow attached the back of it to the bench cushion and as he raised the left side of his torso up, it began to tear away as he struggled even harder to free his ankles, then he lay back down, "You can't do this. Leave my shirt alone. Please! Stop." This time he pushed the left side of his torso up a bit further and the t-shirt ripped, even more, enough that I could see a large part of his beautiful, smooth and very toned torso. My cock throbbed as I watched this boy pretending to be held captive, fighting to maintain his modesty as his imaginary captor tore off more and more of his clothing. Jeremy lay back down again and I watched as he struggled hard enough to free his ankles that the entire bench shook, but now as he pulled on his bound right wrist I saw his young muscles flexed and stretched. Enough of his t-shirt had torn that I could easily see that his right underarm was smooth and hair free and that his chest had good tone for a 14-year-old. His torso began to raise up again and I heard, "Help! Let me Go!" Jeremy suddenly raised his left side up quickly and I watched as the t-shirt tore through and flopped down, leaving him naked from the waist up. He immediately lay back down and tightened the loop around his left wrist until both wrists were high above his head again. The sight was amazing. With his arms in that position, it pushed his chest out and made him draw his abdomen in even further as he again struggled against his bonds. I got my first unobstructed view of Jeremy's naked torso and I was thrilled. His muscle tone was even better than I had hoped and as he struggled it made his muscles flex and tighten again, "You can't touch me!STOP!" Jeremy continued to struggle and call out for help for a full 10 minutes until I saw him loosen his left wrist again. He reached for a piece of very thin rope I had not noticed and once he had a good grip on it he again lay back and tightened the loop around his left wrist. He lay there struggling and as his calls for help got louder I noticed two things. The first was that the back door to the garage was open and the second was that the rope was somehow attached to his track pants. I ignored the open door for a moment as Jeremy called out, "NO. You can't! Help! Please, Sir, stop!" That one would, Sir, thrilled me because I now knew he was imagining a man doing this to him, but what thrilled me, even more, was that with those words the waistband of his track pants pulled down slightly. It took me a minute to see that he had attached the other end to his track pants and looped the rope around the bench so that when he pulled on the rope with his left hand, it dragged his track pants down. The time it must have taken to come up with and arrange this impressed me. "Not my pants too! What are you doing to me? You have to stop!" As the words escaped his mouth the waistband of his track pants lowered another inch and after calling out again, they lowered even further. Jeremy kept struggling to free his ankles and with his legs spread so wide I wondered how the rope would pull the pants free, but a minute later I caught on. He called out again, pleading louder now and as his left hand yanked the rope again I saw that they were not regular track pants, they were tearaways as basketball payers wore. Jeremy yelled out again and as his left hand pulled I saw the pants began to part from his legs at the ankles. It took a moment for me to see they were held together by velcro and each time he yanked on the rope another piece let go. Jeremy began calling out louder, "NO! Leave my pants alone! HELP!" Jeremy pulled hard enough this time that a few pieces of velcro let go at once and as the track pants parted and fell away to just below his waist I got a great look at his legs. Like the rest of him, they were toned and almost as smooth as the rest of him. Jeremy called out even louder as he tugged the rope and his track pants parted and fell away completely. My eyes opened wide as I saw he was now only wearing a pair of very tight, white bikini briefs. His cock was pushed off to the side and I could easily see a damp spot where the head was as it was pointing right at me, only covered by the thin fabric. I took in a deep breath as I watched Jeremy again struggle against his bonds, now able to see almost his entire body, muscles stretching and flexing, his cock throbbing against his white briefs as he called out, "WAIT! Don't! PLEASE STOP SIR!" Jeremy struggled for several minutes as his cock throbbed harder, I hoped it would pop free of the fabric, but the waistband held tight. Finally, he freed his left hand and after pulling the track pants away and dropping them on the garage floor he lay back down and called out for help as his left hand stroked his torso, nipples down to the waistband of his briefs. Jeremy pushed the waistband down slightly, then lay back down and lopped the strap around his left wrist tightly again. Once he was secure again as he struggled I saw the waistband was pulling down a tiny bit more and as he struggled harder it moved down a tiny bit more, enough that I could see he was either naturally smooth or he shaved because he had no pubic hair at all that I could see. Jeremy struggled more, "No more, please. Not my underwear too, you can't! Please! You can't strip me naked!" Jeremy freed his left hand again, just long enough to push the back of his briefs down a bit, then as he lay back down two things happened. First, in his hurry to lay back down his hand, had knocked the keys from the bench leg and sent them well out of his reach, the second was that as he lay down flat on his back his erection popped free of the tight waistband and was now pointing straight up at his face. My heart pounded as his erection, now free and trapped just above his balls by the tight waistband throbbed and pulsed. In his excitement, Jeremy had not even noticed he had knocked the keys away, instead he called out, "NO! Let me go! Right now, let me go! Give me my clothes back. You can't keep me naked." As Jeremey struggled I stood in awe, the more he struggled the waistband caused his erection to throb harder and it was slowly forcing his foreskin back. Now Jeremy called out even louder, "No you can't do this, let me go. Please, Sir, I'm.....a virgin, please stop!" As the word virgin escaped his beautiful lips, my cock pulsed in my pants, I wasn't sure if he actually was a virgin, but he was playing this game alone, which made it very possible and even likely that he was. For a few minutes, Jeremy struggled and called out and each time he did his foreskin stretched back, then relaxed and then stretched back again. I could see he was leaking pre-cum and all his struggling had his muscles and veins sticking out, the sight was awesome. Jeremy called out one more time and as he struggled again the foreskin stretched tighter and then pulled all the way back and trapped behind the wet, purple head. Jeremy gasped loudly as his erection throbbed and pulsed, still trapped and held tight by the waistband of his briefs. The waistband had dropped enough now that it was wedged tightly against his balls and it was tight enough that each movement Jeremy made caused it to stretch tighter as more precum leaked out the head. I saw pleased that his nipples were now very hard and as he called out for help he was shifting his butt slightly to cause more friction between the waistband of his briefs and his cock. "NO! Let me go! I'm a virgin, you can't do this Sir." At that moment I knew I had to get closer, I crept away from the window and through the gate, then silently stepped through the open back door of the garage and now stood a few feet away from Jeremy's head. The view was impressive as I gazed upon his tight young body, all bound up securely ecxept for his left wrist, a mere couple of feet in front of me. I took another two steps closer, close enough now that I could smell his body wash and the unmistakable aroma of his pre-cum. I stood silently, knowing Jeremy was making enough noise that he would not hear me. As he continued to move his butt slightly, stretching the foreskin back tighter, releasing it and stretching it again, hia pre-cum now ooozed out. Jeremy did this for several minutes, his cock now throbbing up and down enough that it was moving the fabric of the waistband on his briefs. It dawned on me that he had done this before many times and I soon caught on that he would not be able to cause enough friction to make himself shoot his load, something that was confirmed as he said, "Please, Sir! Please! I'm begging you!" Jeremy then moaned as his foreskin stretched, then again and again as he said in a lower tone, "Please Sir...... I'll be a good boy." His tone had changed and gotten even lower, and I knew he was now giving in to his imaginary captor as he said, "Please Sir, I'll be a good boy. PLEASE! Let me cum Sir." I watched as his foreskin stretched again and for the first time noticed that there was another leather cuff attached to the left leg of the bench. Jeremy must have taken turns keeping one or the other wrist free. Seeing it gave me an idea and a minute later I acted on the idea. Jeremy called out, "I give up Sir. I'll do anyhthing you want, just please let me cum. I'll do ANYTHING!" Jeremy began to slowly loosen the strap from his left wrist and as he did I knelt down and grabbed the cuff laying at the leg of the bench. Before he could push the blindfold up I quickly snapped the cuff around his left wrist and buckled it and then snapped the lock in place. At the same time I apllied enough force to cause him back flat on the bench cushion as I secured the cuff tightly to the leg of the bench. His head moved from side to side, trying to force the blindfold off as his mouth opened, "What the fuck! Let me go!" I stared at every inch of his body as I said, "That sounded like an order Jeremy. You are in no position to give orders." Jeremy stopped struggling at the sound of his name and I knew he was trying to figure out who I was. "Who are you? Let me go." I gazed at his naked body, loving the view from this angle as I said, "This is an interesting set up you have here Jeremy, the cuffs and everything, looks like you have done this many times before." His face blushed a deep red as he again tried to get the blindfold off. Before he spoke I added, "Has anyone ever joined you in your game before?" His head shook and he began to say no, but then, "LET ME GO!" "Jeremy, that sounded like another order. Maybe I should just leave and your Mother can free you when she gets home tomorrow." He looked surprised and then scared that I knew his Mother's routine and at the idea of her finding him like this. "Who are you? How do you know when she'll be back?" I gnored his questions, "How would she react to finding you like this Jeremy?" His face blushed a deeper red as his cock continued to throb and pulse. "Please Sir, who are you? Let me go, please." "I imagine your mother might just take away your playroom here, confiscate your cuffs, maybe even more." I saw that the idea scared Jeremy as he struggled to come up with something to say, and thinking of nothing, he again pulled at the cuffs, "Please Sir, let me go." I again ignored his words, "Maybe I should just leave, I'm sure your Mother jane will be fine when she finds you like this." Hearing his Mother's name let Jeremy know that I knew more information about him. His mouth opened and then closed and then opened again, "No wait Sir, please. Don't leave me like this." "Well then Jeremy, maybe we should work out a deal?" Jeremy was scared and anxious, but his cock continued to throb. "What deal Sir?" "The deal is, we finish your game, but with me as your captor." His head began to shake back and forth but before he spoke I said, "Or I can leave you here and let your Mother find you." He tried again to free himself and as he did I ran the back of my hand softly over each of his nipples. Jeremy was bound tight on his back, all he could do was lift his head, which he did, "Wait! Sir, please! Who are you?" I knew it was time to take control as I made my voice loud and firm, "Jeremy, I'm your captor, and you are my prisoner. That is all that matters." I stepped back until I was at the side of the bench and slowly lowered my right hand and let it caress his chest and upper abdomen. Jeremy gasped and I thougut he would try to pull away but when he didn't I softly pinched his right nipple and heard him moan. I traced my finger down until it was almost at his cock and watched Jeremy take in a deep breath and let out a low moan. As my other hand caressed his chest Jeremy seemed to relax a tiny bit and I knew he was accepting his fate as my prisoner. I also knew that he was probably doing this out of necessity, just wanting me to free him. My job now was to make him enjoy it so much that I could come back anytime I wanted. I stepped back and picked up a pair of scissors from the table beside the bench. "A body as fine like yours should be totally naked. Let's get rid of these briefs." Jeremy struggled again, then, "No please Sir! Wait! You can't strip me naked." "You are my prisoner boy, I can do anything I want." I then gently grabbed the waistband of his briefs and very carefully snipped and pulled them free, dropping them on the floor. Jeremy's body tensed up and I loved how it made his muscles flex and I knew he now knew exactly how vulnerable he was as I heard, "I'll be a good boy. I'll do anything you want Sir." I hope you have enjoyed this chapter. Comments and suggestions are always appreciated.