Date: Fri, 22 May 2009 05:34:43 -0400 From: Jonathan Matthews <jonafunu@hotmail.com> Subject: The Untellable Truth about Jake (Chapters 27-30) Note/Disclaimer: Well everyone I'm back with yet another addition to the Untellable Truth about Jake series! For those who care about my behind the scenes process, I actually finally wrote the epilogue of the story tonight, so with the ending set in stone and the ball rolling towards the finale, I hope that you all stay tuned. I really can't say how much longer we have to go. My initial thoughts are probably ten or so more chapters, although that could balloon into considerably more. As always your thoughts and opinions are greatly appreciated and needed! If you are under eighteen, do not like the man-boy genre or this story is illegal where you are, then don't read it! This contribution includes sex between a twenty two year old man and a nine year old boy. Please read at your own discretion. ********************************************** Chapter Twenty Seven After signing a legion of paper work, being taken to the bank to withdraw the entire contents of my life savings and taking a seat in my new (at least to me) SUV, I found it very difficult to navigate the streets in the same manor I was accustomed to. To say that this automobile was huge, would be an understatement. I felt as though everything around me was suddenly miniature, and that I was at the helm of a great tank or assault vehicle. With all that being said, it was already three-fifteen and I couldn't be late to meet Colby at the bus stop. Then there was Marco, my sweet co-worker who I had never once given a second glance. What exactly had he meant by the kiss? Did he like me? Did it mean anything at all? I knew Italians, or at least I thought Italians, were fairly touchy feely people, but was this just that or something more? I couldn't help but find my fingers meeting my lips every few moments, and the very fact it bothered me so much made me more concerned than anything else. I had Colby, why would I even care what this kiss meant? I flew into Stephanie's driveway at 3:25 and found myself rushing down the sidewalk with as much speed as I could muster. Although a good portion of the snow had melted, there was still enough left to make any misstep a memorable one. "Jake!" Colby yelled, walking off the bus as soon as my tired body came into view, I had just made it. "Colby!" I called back, stopping to catch my breath and extending my arms for him to come and hug me. Colby came, tried and true, rushing towards me and planting his small frame directly within my arms. I hugged him tightly, planting a kiss on his forehead. "Did you have a good day at school?" "Yeah it was great! We really don't have a lot to do since this is the last week before break and all so we watched some movies and did some projects and stuff." I nodded, placing my hand within his own and walking with him towards home. I listened intently to each word as though it were the most important thing I had ever heard. "Did you know they are having a light display in Hillsboro on Wednesday? Can we go?" I laughed, trying to answer each question as the words flew out of his mouth at a record pace. "No I didn't know but sure, I don't see why not." "Yay!" He shouted, throwing his hands into the air and suddenly coming down from his high a little. "Oh sorry, did you get a new car?" I nodded, looking over at him. "Yep, Marco's Dad hooked me up with a new one." "Cool! What kind is it?" "A tank actually." I laughed. Colby's eyes grew large. "Really?" "Of course not." I nudged him in the side playfully. Before he could ask for a real answer we had risen over a hill, and the large black behemoth had come into view. "Whoa, it's huge!" Colby exclaimed. "Told ya." I said. Colby looked at it with mild trepidation, I don't think he had ever seen anything that big up close before. When we finally approached it, he looked up at it and knocked on it a little. "You know our teacher said that huge SUVs are bad for the environment." "Truly? She said that? Well this thing was pretty cheap so I had to take it or leave it." "I guess it's okay then." Colby smiled at me. "Glad to have your approval." I winked, leaving him blushing. Stephanie managed to walk outside at that exact moment, looking at the SUV more than she was either of us. "What in the world did you get? A tank?" I laughed along with Colby. "Nah nothing that extreme, but Marco's Dad got me a good deal on it." "I'd hope, it will cost you twice what it's worth to fill it up." I grumbled a little. "Can we go for a ride in it and get something to eat?" Colby asked, hopping up and down a little. "Taking advantage of me for food huh? You sneaky little devil." Colby giggled. Stephanie smiled, "I'm actually pretty hungry myself, have you eaten?" I shook my head. "Well let's go then! I'll buy." Stephanie smiled, walking over to the front passenger door as Colby followed her. I stood back watching them, smiling a little and glad to be back from bizarro world. The whole experience with Marco had shaken me, but I wasn't about to let it ruin the rest of my day off with Colby. "Where to folks?" I asked as I climbed into the front seat and looked at Colby through the rear view mirror. He looked decidedly smaller than he usually did. "Where ever you can fit this thing, it's HUGE!" He exclaimed, a mischievous look etched across his face. "Nice one wise guy." I stuck my tongue out at him causing him to giggle. "Anywhere you want Jake." Stephanie smiled, patting my leg. I nodded and put her into reverse, backing out into the road and driving off to find something. I really didn't have anything in particular in mind. "McDonalds?" Colby asked. "Not really in the mood..." Stephanie murmured. "Burger King?" Colby asked again. "Isn't that almost the same thing?" Stephanie asked. "Uh, Wendy's?" He asked again. "Oh lord..." Stephanie laughed a little, shaking her head as she planted it in her hands. "Okay you two, isn't this supposed to be up to me?" I asked. "Yep!" Colby exclaimed, a look of interest on his face as he waited patiently for me to announce our ultimate destination. "How about Mexican?" "Sure!" Colby exclaimed. "Sounds good." Stephanie smiled. I nodded, with a sense of newly found purpose in exactly where I was taking this tank. I knew I would get used to her in time, but at least for the moment she scared the living shit out of me. By the time I had managed to make a few turns without killing anyone, I made it to a Mexican restaurant and parked as far away from everyone else as was humanly possible. Chapter Twenty Eight The early dinner was good, Colby ate too much as usual and Stephanie spent the remainder of the evening scolding him for it. By the time we got home, Colby's homework done and a few chores around the house accomplished, it was time for him to go to bed and Stephanie was in the mood for another of her walks. By the time I had managed to get Colby into bed with a promise of my imminent return, I was shrugging my coat on and meeting Stephanie at the bottom of the stairs. As soon as we got down the road a comfortable distance, Stephanie broke the silence. "So what's on your mind?" "Is it that obvious that I have something on my mind?" "Yes" She laughed. Lighting a cigarette and handing it to me. I nodded in gratitude, taking a draw and sighing a little. "Well this afternoon when Marco and I were at the dealership, he kissed me." "He kissed you!?" "He kissed me." Stephanie and I walked in silence for a few moments before she spoke again. "Now when you say kiss, do you mean a peck on the cheek or what?" "I mean he kissed me on the lips, it's not like there was tongue or anything but it seemed pretty sensual, I guess." "Did you ask what he meant by it?" "Of course not!" I protested. "I mean, no, I didn't really want to read anything that wasn't there." "Well that's definitely something to think about." Stephanie said, taking a drag of her own cigarette and flicking the ashes into the wind. "What do you mean? I have Colby, what's there to think about?" Stephanie laughed a little. "Well while all that is very sweet and I'm perfectly okay with it, it doesn't exactly have long term relationship written all over it now does it?" I wasn't exactly sure how to respond. Hadn't she forewarned me not to hurt her son a few days before? This seemed a complete reversal from the original conversation. "No matter how you look at this relationship, Colby is nine. I know he loves you and if you quit showing him the same affection you show him now, he'll be hurt, but he'll get over it. He's going to outgrow you Jake and you need to accept that now before you get too far along to let go." I bit my lip. Certainly I had thought the same things before, almost freaked out about them, but I didn't really want to believe them. Colby would outgrow me and then what would I be? Too old for college and ill prepared to start a relationship with an adult. "Now of course none of this means that's what that kiss meant, but you do need to be thinking about that. What do you think about Marco anyway?" "I've no idea, I've never THOUGHT about Marco before. I figured he was straight." Stephanie laughed. "You have to be the only gay guy in the world without gaydar." I blushed, maybe I was. "Would you ever, you know?" She nudged me in the side playfully. "I don't know!" I laughed. I really didn't. I had never thought of Marco in those terms before and it wasn't exactly the sort of thing that I wanted to think about. Or did I? "What's so wrong with just sticking around here and hoping Colby doesn't outgrow me?" "The same thing that's wrong with you never going to a real college." She said, speaking as lightly and calmly as she could. "So I'm selling myself short?" She nodded. "I really don't think of Colby that way, he makes me happy. He can't stay a kid forever." "Well would you have any interest in him if he wasn't a kid?" I scowled at her a little. "I may like kids but I do like adult men as well, thank you very much." "Good, I was actually beginning to wonder." I smirked at her. "It's just really defeatist to let your life always stay the same. I have a kid, I can't go anywhere and I'm, well, getting old. You still have many years ahead of you and you have nothing to stop you from chasing the dream." I sighed. "Trying to get rid of me already huh?" She punched me in the arm playfully. "Now you know you have a place with me as long as you need it. Even if you chose to stay indefinitely, you'd be welcome, although I would be very disappointed." I smiled a little, at least I knew the door was open to that option if I chose it. If even there was another option on the table. "Thanks I appreciate that." She nodded, "Anytime." We both flicked our finished cigarettes on the wet cement at the same time. "So Colby wants to go to this light show in Hillsboro on Wednesday, is that okay with you?" I asked her. "Sure, are you going to take Susan?" I nodded, sticking my hands in my pocket. "Yes, figured it would provide a wonderful sense of occasion." "Look at you, using such big words!" She laughed heartily, clapping her hands together in delight. "Glad you like em Mom!" I wrapped my arm around her shoulder and playfully patted her side firmly. "What am I ever going to do with you?" She shook her head. "So, do you think I should call him? Marco I mean?" I asked, feeling still a bit shaky about the whole thing. "Sure I don't see why not. Colby will probably be fast asleep." "I wouldn't count on it." I murmured. I wasn't entirely sure whether he'd be expecting more 'fun' or not, I was certainly amendable either way. "Well let's head home then, I wouldn't want you to leave your fans waiting." She winked, putting her hand inside my own. I smiled, squeezing hers as we made our way back around the block towards the house. The conversation and the general good will had blocked out the majority of the cold. The fact she had reacted to the whole Marco thing the way she had, was extremely surprising to me. I still wasn't sure whether I wanted to actually pursue a relationship with him or not, but I was open to considering it. If Colby was indeed poised to outgrow me, then I had to do something. Being a hermit for the rest of my life didn't exactly appeal to me. There was a part of me that found my thought pattern completely unbelievable. I had waited so long to have Colby in this manner, and it was something that I never thought I'd actually achieve. Those long nights spent in fear of each touch, each kiss, each temptation, each of them sent fear into me that marked me forever. Within the past week or so, I had experienced a transformation. I felt safe, I felt loved and I finally felt at peace. There was no doubt in my mind that what I felt for Colby was genuine love. Every time I looked at him it was as if he were a completely new child. He always had something new and interesting to say, and the way in which he always looked at me with such adoration amazed me. It never lessened, if anything it simply grew with each passing day! Why then, with all of that in mind, would I even begin to think about Marco in that manner? Maybe it was that those fears weren't entirely dormant, maybe I did feel a bit of repressed guilt about the whole thing, regardless of what it was, I couldn't be sure, and I wasn't exactly sure that I could ever come up with a satisfactory answer. I knew that I loved Colby enough to not ruin his life. I knew that I didn't want Colby to regret me, and that I wanted him to be happy. Would he hate me if I left? Would he hate me if I stayed? Did every single experience with him leave a lasting impression that I'd have no way to remove no matter what choice I made? I couldn't be sure of the answer to these questions, but I knew that I would at least entertain the idea of growing up. I would call Marco, I would ask him exactly what the kiss meant and I would start looking at colleges. If the kiss meant nothing, then so be it. If the kiss meant something, then I'd see where it went. Whether I decided to stay with Colby and see what would happen, or go with Marco or someone else entirely, I would need a college education to bring to the relationship what that person deserved. As foreign as these thoughts were to me, they were an epiphany that was long over due. I watched as the porch came into view and as soon as we climbed inside, Stephanie disappeared into the kitchen and I located the phone. The actual act of doing what you feel needs to be done is often much harder than the thinking ever was. My thumb teetered above the numbers, trying their best to press down but I found it a difficult feat. Maybe it was too late? Maybe I should let him call? This was all too much for me to absorb at once. One thing was for sure, if I kept sitting here staring at this phone, Stephanie was going to begin to think that I am crazy. I pressed the first number, 5, oh glorious 5! Five reasons not to call: It's late, I have no idea how he really feels, I'm tired, I have work tomorrow, that picture in the corner is hung crooked and I really should attend to it. I managed to press the next, 0, yes 0. The exact number of actual reasons I had to not call. He had told me to be in touch, he had kissed me, he had made a way for me to get a car so soon. At the very least, I owed him a thanks. My thumb managed to relocate it's mobility and I dialed the rest of the numbers without nearly as much trepidation. "Hello?" Marco's voice echoed after only two rings. I swallowed deeply. "Hi." I managed to squeak out. "Dude! How's the car? Do you like it?" I nodded, "Yeah she's pretty great. A lot bigger than I thought but good. I really appreciate what you did for me it means a lot." "Anytime, anything for you Jake." I smiled, blushing a little. "So, are you working tomorrow?" I thought for a moment before I replied. "Yeah actually, late night, how about you?" "Same here." He replied. I groaned, looking down at my feet and suddenly at a loss for words. "Mom made some great pasta tonight, want me to bring some? It can be a date." My eyes grew large. "Yeah! Sure! Why not!" I replied, probably a little too loudly in hindsight. "Cool. See you at work tomorrow." "See you." I hung up the phone, lowering it for a moment and just staring at the keys. Stephanie poked her head in the living room, "So?" "No resolution, he's working tomorrow night though." "So you're working together?" "Yep." She giggled, clapping her hands together in girlish satisfaction. I suddenly felt very dirty. "Well I'm going to bed, I'm completely beat." "Aww, no more talking huh?" Stephanie teased. I stuck my tongue out at her in a playful manner. "Plenty of time for that later. Do you need anything before I tuck in?" She shook her head, "Everything's good on the western front." I smiled, hugging her as she returned it, and began my ascent towards Colby's bedroom. Chapter Twenty Nine I crept as quietly and cautiously towards his door as was possible. I honestly felt dirty for having considered Marco at all at that point, and was more than a little guilt ridden because of it. I wanted to keep Colby fast asleep, if indeed he was asleep. I wasn't entirely sure whether I'd be in the mood for sex or not. Of course if he wanted it, that would change, but at least for the moment I could feel dirty and like a cheater. As I slid the door open and peaked inside, I saw Colby bundled beneath the blanket, his back turned towards me. I sighed in relief, at least at first appearance he appeared to be asleep. I crept in, closing the door quietly behind me, and tip toed to the corner to change. As soon as I removed by shirt and threw it into the darkness, I heard the crash of a lamp and shut my eyes tightly. "Jake?" Colby asked, stirring from his slumber. "Sorry, must of hit something with my shirt." "S'ok, I wanted you to wake me up." I heard him shuffle within the sheets as he sat up, turning his side table lamp on and casting a glow on my half dressed form. I was thankful to still have my pants on. "Are you okay?" He asked, smiling at me through groggy eyes. "I'm great! How about you? Still tired?" I asked, trying to will him into a coma. "Nope I'm awake now." He giggled, flashing her pearly whites at me. I smiled in return, pulling a night shirt over my chest and trying to determine whether it was a good idea to remove my pants or not. "Can I watch you change?" Colby asked, staring at me with curiosity. I felt a stream of inspiration flow within the confines of my pants, but my mind was so heavy with guilt that I wanted to avoid the topic of sex as much as was possible. How exactly would I explain that to him? That I wasn't in the mood? Kids had abundant energy, and telling him I wasn't in the mood was equivalent to telling him I was old. "I'm not so sure if that's a good idea." I tried to protest, feeling my will sinking to previously unforeseen depths. "Oh... You've seen me naked before." Colby commented, his face contorting to one of confusion. I groaned. His logic was infallible of course, I had seen him naked. On any other occasion, this would have been a harmless request with which I would have gratefully complied. Tonight was different, but I had to at least keep up appearances for his sake. "Okay then." I smiled a little, watching his face turn to one of excitement. My hands fell to my pants, unfastening the button and freeing their tight place around my waist. I slid down the zipper, letting my fingers go within the band and push them down to my ankles. I stepped out, standing there in nothing but my t-shirt and my boxers. The noticeable tent seemed to be what Colby's eyes were immediately drawn to, but taking off my boxers wasn't exactly a part of my normal ritual. As a testament to the unorthodox nature of this relationship, I had seen Colby naked several times and he had never seen me. I wasn't entirely sure whether he had ever seen a grown man naked before or not. "Have you ever seen someone naked before?" I asked, out of curiosity. "Nope, just Mom. I want to see you naked though." He grinned, resting his chin atop his fists. I groaned a little to myself, completely unsure of where this was going. Despite my mental state, my cock was throbbing, and was begging to be released. It's been said that men think with their penises, and this is probably true, but at least I knew little boys did as well. I slid my hand into the elastic waist band and slid them down, letting my member pop into view as Colby's mouth dropped in shock. "It's HUGE!" Colby exclaimed, as quietly as was possible. I couldn't help but blush, my right hand finding it's way to the back of my head to rub it, as I was accustomed to. I never found him very remarkable, a mere six inches, but by comparison he was quite a bit larger than Colby's was. At least with a kid around, my libido would be boosted sufficiently. "Thanks I guess." I responded. I watched as Colby stood up on the bed, removing his night shirt and underwear and depositing them in the corner. His gloriously perfect body shone in the light as thought it were a newly created star. His perfect little penis stood it's proud three inches, taking every ounce of my attention away from the previous matters of the day. "We can sleep naked okay?" Colby half said, half asked. "Sure." I responded, suddenly feeling a new eroticism rise within me. Never once had I gotten off while in the company of Colby, and I doubted this night would be any different, but it certainly made me more conscious of that fact than I ever had been. As I reached the bed, laying down next to him, he decided to climb on top and stare me in the face. His soft body felt heavenly against my chest. "You're really hairy Jake" He giggled a little, his hands rubbing my chest playfully. Although I only had a sparse collective of hair spread mainly across a thin strip between my man breasts (not really sure what else to call them) and a happy trail beneath, it remained considerably more than what Colby had. "You're really soft." I winked, kissing his cheek softly. "I love you Jake." "I love you too." I reached over to turn off the lamp but he stopped me. "Don't. I want to see you." I smiled and blushed a little. "Sure." Colby slid off and sat Indian style by my side, staring intently at my towering member. He reached out timidly, stopping just before he touched it as his eyes locked with mine. "Can I touch it?" I nodded, I wanted very badly to tell him that he could do anything he wanted, but I felt it better not to. I watched with curiosity and lust as his small hand reached out, grabbing around my shaft and pumping up and down in one solid motion. I couldn't begin to describe how the softness of his hands felt against it, it was something that nothing in the world could ever compare to. Sure many men had touched him and I had done so on more than one occasion, but Colby's soft hands felt so much more intense and wonderful than any others had. I groaned a little, in response he released it and looked at me in concern. "Are you okay?" He asked innocently. "Yes, it just felt very good." Colby smiled, apparently proud of himself. "Cool, I want to make you feel good." I smiled in return as his hand wrapped around the shaft again, his other hand gently caressing the tip and remarking at the sticky substance that found it's way to the top. "What's this?" He asked, the tip of his finger finding itself pursued by a solitary string. "It's called pre-cum. It helps make it easier to have sex. It only comes out when you're really excited about having sex with someone." "Oh." Colby blinked, thinking about the words I had just spoke. I felt a pang of regret for my particular choice of words. "Do you want to sex me?" He asked. I almost spurt all over myself, the concept was extremely hot but I knew that he was too young for it. "Colby there are many things I would do to make you happy, but I think you're just a little too young for that." "No I'm not!" He said defiantly, sticking his fists on his hips. I groaned, trying my best to think of a way to stave off this question. "Do you know how gay men have sex?" I asked, hoping he didn't but knowing that he was doubtlessly armed with the knowledge. He had expressed previously that his classmates talked about such things on the bus. "Well I know when you sex a girl you put your penis in her vagina, and I KNOW gay men have sex. I just don't know where at." I smiled, slightly relieved that he didn't know that much. I almost teetered on the idea of lying, saying that oral sex was the only sex men had, but the idea of actually telling him the truth appealed to me because it could possibly gross him out or turn him against the idea. "Well you put your penis in the boy's butt hole." Somehow putting it that way didn't make it sound nearly as erotic as it truly was. "Oh" He commented, looking down at the rock solid penis in his hand. The look on his face wasn't one of repulsion, but one of very deep thought. It concerned me to no end. "Does it feel good?" "For who?" I asked. "For both I guess." He shrugged, still looking at my cock. I was assuming he was sizing it up against the small size of his body. At least I silently hoped that's what he was doing. "Well it feels really good when you put your penis in someone, actually it's one of the best feelings in the world. It can feel good having someone inside you, but that takes some years of practice. The first few times it hurts, for any normal adult, but for a kid..." I trailed off. "Because my butt is smaller?" He asked curiously. "Yeah I imagine it would hurt you quite a bit. It might feel good, eventually, but I can't guarantee that." Colby sat there, using the tip of his left hand to tease the tip of my cock, and his right still wrapped solidly around the shaft. "So it feels better when you put your penis in someone that it does when someone sucks on it?" He asked after a moment on long silence. I nodded. "It does." He shook his head and laughed a little. "I don't think anything could feel better than that." I laughed a little too, I was incredibly turned on and incredibly nervous at the same time. "You can put it in me, if you want." Colby said, turning and looking at me with a blank expression. I'd never seen such a lack of expression on his face before. I felt myself momentarily hesitate. The idea was appealing, and to think of how good he would feel nearly drove me to cum right there and then, but the thought of hurting him didn't appeal to me at all. "Colby it would feel really good to me but I just can't hurt you like that." "You said it would feel good one day didn't you?" "I don't know that, I don't know how far you can be stretched at your age." "But I want you to!" Colby jumped onto his knees, looking at me with a look of determination. I groaned, feeling the blood flowing through my member at an increased rate. I wasn't particularly thick, but I just couldn't figure out how I could do this without causing some sort of permanent damage. "Why do you want that so badly?" I asked. "Because I've never made you feel good before and I want to! Plus I love you!" He said, his arms stretched out, moving animatedly with each word. I paused again, examining the look of exasperation on his face. There was not much will in me, from a carnal standpoint, to refuse such a request. The reality was that I had been entrusted with him to enjoy moments like this, and taking advantage of his ignorance and desire to please me seemed incredibly dirty and under handed. I'm not entirely sure if someone has ever found themselves in this predicament, or if any man would have the strength to refuse, but it was one of the most difficult things I had ever been faced with. "Please?" He asked again, looking deeply into my eyes. "Colby I..." I trailed off, taking my eyes off his for the first time and staring at the closet in the corner. "If it hurts too badly you have to tell me to stop immediately. If I ever hurt you too much, I don't think I could forgive myself." Colby grinned and nodded. "Kay!" Colby immediately sat up completely, staring at me with a mischievous grin etched across his angelic face. "So what do I do?" I hit myself in the forehead a little. "Well first of all we need some kind of lube... umm... that is something to make it slide in easier." Colby mouthed an 'Oh' bouncing up and down a little. "I don't have anything normal, um, do you have any vaseline?" I asked. "Yup!" He shot off the bed before I could say another word, nearly falling as he ran into the hallway and towards the bathroom. I was glad that Stephanie was a heavy sleeper because I wasn't entirely sure what she'd think about her son going butt naked to the bathroom to get a jar of vaseline at 11:30 at night. As soon as he returned, he threw the jar at me and hopped back on the bed, staring at me like a student in a class that truly interested him. "Now the next problem is the size dilemma, I can't exactly mount you..." I thought for a moment, my eyes settling on a chair in the corner. "Well, we can always do that..." His eyes followed mine to the chair, his left eyebrow raised a little. "Why do we need a chair?" He asked. "You'll see." I replied, sliding to the edge of the bed and standing up. I walked over and sat down, watching Colby turn to stare at me, still sitting on the bed. "Come on over." I said, watching as he slid off to stand in front of me. "Are you ABSOLUTELY sure you want to do this?" "Yes already! Sheesh!" Colby laughed a little, putting his hands on his hips. I smiled, still as nervous as ever but glad to see that he was in high spirits. "Turn around." I said, removing the top of the jar and putting a little on the top of my right index finger. Colby replied, turning with his perfectly formed ass directly in my view. I slid my finger within his cheeks, gently finding the hole and lubing it as much as I could. I slid my finger in just a little, finding a fairly good amount of resistance and watching his body tense in reply. "Tell me if you want me to stop at ANY point, okay?" "Kay." Colby replied. I pulled my hand back, adding a bit more vaseline to it and pressed back inside of his cheeks. This time I pressed firmly into his virginal hole, allowing my finger to slip in to my first knuckle. His ass crashed down like a ton of bricks. "How does that feel?" "Weird." Colby commented, shivering a little. "You are going to have to loosen up or this isn't going to work." "Kay." I waited a moment as his muscles loosened considerably, allowing me to slide my finger up to the second knuckle. He tensed again, but I felt it subside as I decided to push it in the rest of the way as quickly as possible. As soon as it was in, he tensed completely, replanting his feet and sighing a little. "You still okay?" "Yeah it's just, really weird." He said, echoing the earlier opinion. I slid out slowly, to the first knuckle, stopping just briefly enough to hear him sigh again. "How was that?" He giggled a little, "Kind of feels like taking a crap!" I laughed, in spite of how guilty I felt. I pushed in again, making it all the way to the third knuckle before he tensed again. "I want you to bare in mind that my penis is quite a bit thicker than my finger." "It's okay. It doesn't hurt, it just feels weird." I nodded, sighing a little and deciding that the lubing had taken long enough. As I removed my finger completely, he turned to face me, his face flushed with the new feelings he was experiencing. I took some more vaseline from the jar and thoroughly coated the head of my dick. I was going to make sure that if he could handle it, he would at least do it as lubricated as possible. His eyes watched, growing a little larger at the size of the head as it pulsed with each touch. "Any second thoughts?" I asked, looking up at his blue eyes. "Nope." He replied. Chapter Thirty "I'm going to pick you up and you are going to put your feet on the arms of the chair with your back facing me. I want you to use your legs to help me determine how fast I need to let you go down and I'll try to control your weight as much as is possible. If at any point you think it's too much, just tell me and you can either push up with your legs or I can pull you off, okay?" "Kay." He said, licking his lips a little in an absent minded manner. He turned around as I wrapped my hands around his torso and lifted him into the air. He obediently bent his legs and placed each foot on their respective arm rest. His ass hovered a few inches in the air above my cock. I began to feel my breath quicken. I started to try and determine exactly how much control I really had. I hadn't already thrown him on the bed and raped him but I did relent to what was nearly an unreasonable request. Even in my darkest and most twisted fantasies, I never once imagined that having sex with Colby would be a possibility. It was something I had thought about, certainly the first time I ever saw his perfectly formed ass, so there had been quite a bit of time of anticipation in between. I tried my best to remember the time I lost my virginity. I had cum within mere moments of entering, but I couldn't exactly remember how likely I would have been to have stopped. Certainly I had, had sex with men since and had built plenty of control for any situation concerning them, but this was completely different. This was a boy, but not just any boy, the boy of my dreams. Of any other child on the Earth, this was certainly the one that I found most attractive. I couldn't think of a single part of him I would change, and every aspect of his body, his face, his character and his personality was absolutely perfect as far as I was concerned. I had never been with someone whom I thought so highly of. I've also never been with someone whom I loved so much before. My only saving grace, I hoped, was that my love for him would out weight my more base desires. If he began to descend towards my waiting hole and the feeling was too much, no matter what happened I had to relent and let him off. I had to control my desire and I had to let him be completely in control. He was too small and weak to refuse my strength, and if I let my desires get the best of me, there was little he could do but feel the brunt of my sexual frustration. This was the last turning point, this was the absolute and final opportunity for me to refuse. It would disappoint him, but at least I could sleep. He may bring it up again though and the fact is he may find me at a moment where I couldn't control myself. This relationship had gone to a level of danger that I had never anticipated. As I wondered at my options, I made what I considered at the time to be a very poor decision, I began to lower him. As soon as the tip of my cock met with his hole, I felt the strength of his legs stop me immediately. I was in fact quite surprised at how strong they were. "Just go at your own pace, nobody is rushing you okay?" I saw the back of Colby's head as he nodded. I watched the tenseness in his calves recede a little as the head of my cock began to press more firmly against his hole. He suddenly stopped again, letting an audible gasp escape his lips. "Maybe you should just make me do it so I can't stop." I shook my head, "We have absolutely no idea if this is going to hurt a whole lot or not. This is all you." He nodded, "Thanks." I nodded. His legs began to shake a little as he went down further, although I couldn't get a good look at what was going on below, I began to feel the head of my cock penetrate a little, the head was nearly halfway inside before he stopped again, his legs shaking violently as my hands tightened around his torso. "I've got you, take a rest." Colby nodded again. "It doesn't hurt yet but it's kinda scary." I smiled, kissing his back gently. "Like I said, you can stop if you want." "Nope." Colby said, his voice as determined as ever. I felt him put weight on his legs again as I lessened my grip on his torso. He slid down slowly. As soon as I felt my head pop inside and my eyes rolled to the back of my head, he yelled out. I caught him just in time as his legs began to buckle beneath him. "Do you need to get up?" "NO!" He called out. I felt his body shiver as I held him tightly. The feeling of my head inside of him fought with the sense of responsibility I felt towards him. I was extremely grateful that my love was holding strong at that time. His ass was clamped down tightly around my head, and just as I felt it loosen a little he began to lower himself again. I nearly yelled out, the absolutely tightness and sensation going through me was almost too much to handle. He was nearly an inch below my head when he stopped again, this time his legs held firm. "What does it feel like?" I asked, breathlessly. "It's really big." He said, just as breathless as I was. "Just go whenever you want." I said, feeling my cock throb inside him as his muscles remained just as tense. He loosened, and began to descend again, stopping about half an inch at a time and collecting himself before he continued. I felt the least bit of his cheeks touch my stomach and I knew that he was close to having me completely inside of him. I fought very hard against my desire to just pull him down. My cock was strained, almost uncomfortable, but still throbbing away inside of his anal cavity. I knew that with a few tried and true pumps, I would be done in moments, but I didn't want to hurt him. His legs gave way suddenly, as my hands wrapped tightly around him again to support his weight. "It's okay, let go." He whispered, his voice was strained and I could tell that he was, at the very least, in extreme discomfort. I nodded and gently released my grip. As soon as he slid down to the very bottom he yelped. He placed his hands on my legs and breathed heavily. "Are you okay?" I asked, finally able to turn enough to where I could see his bright red face. "I think if I sit.... here a moment... it will be okay... it's just... REALLY big." he spat out between breaths. I wrapped my arms around his torso, drawing him close to my chest. I was completely inside of him and even though this feeling of sexual intensity was so strong inside, I felt the most love and affection towards him that I ever had. "I love you so much Colby and the fact you want me to feel good means so much to me. I just want you to be happy too. There are other ways to make me feel good." "This is the best way isn't it?" He grunted a little. "It well, yeah it definitely feels the best." I said, running my fingers casually across his chest. "It's almost starting to feel okay." He smiled at me a little, sweat standing on his brow and his red face staying the exact same color. I nodded, letting my hand fall down towards where my cock was inside of him. I fingered the moisture a little, drawing it back to my face and saw no red to my relief. I couldn't be entirely sure as to whether he wasn't bleeding or not until he rose up, but the initial evidence bode well for a positive experience. "The next thing we're going to do is lift you up until you're nearly off of me, and then we're going to lower you onto it again. If you ever get used to this, then we'll do this a lot quicker. The same motion I make when I make you feel the way you do when I suck you, is the same one I need to feel that way inside of you." Colby nodded, his legs were in an incredibly awkward angle. "I don't think I can push up on my own." I smiled "Just tell me when." He let out a huge breath and nodded, "Kay." I wrapped my hands around him again, gently and slowly helping him up until he was very nearly about to have my head leave his body. He was then able to hold his legs steady. "It feels kinda good when I go up." He laughed a little, a bit of a grunt following. I smiled, "It's what really feels the best when you're used to it." Colby nodded and I felt his legs begin to lower him again. This time he managed to last until he was about half way down the shaft before he stopped. I took the opportunity to once more examine the moisture on my cock. Upon checking there was still no red. I was beginning to feel a little more than excited about the prospect of this. "Okay." Colby nodded, sliding down again as he made it all the way to the base of my shaft. Almost as soon as he hit it, he nodded to instruct me he was ready to come up. As soon as he was back up towards the top, he regained control and began to lower himself again. My breath caught in my throat, my head had grown larger than it had all night. With him in complete control and my hands nearly there to catch him if he fell, I knew that I wouldn't have to wait much longer for climax. He was much too tight to hold out. Plus it probably wasn't in his best interest to wait. As soon as he rose up again he lowered completely without a single stop. He grunted loudly, his legs shaking violently beneath him. I was nearly ready to help but he pushed himself up again before I could, and went back down. I began to feel the familiar rushing of cum rising to the tip. The tingling sensation was most certainly only moments away. "Okay Colby, I don't really want to cum inside of you because when I do..." Colby cut me off. "You make baby juice." I almost laughed, and probably would have if I wasn't so close. "Yeah I just don't think you need that inside of you. So probably within the next few moments I'm going to push you off very quickly. I don't want you to be scared okay?" Colby nodded, lowering himself on me as I felt the tingle near. He drew up and down, up and down, up and down, as soon as he began the fourth upwards motion, I began to feel an intense tingling and my hands wrapped around him, prepared to push him down and force the entire contents of my orgasm deep within his bowels. Where I found the strength to refuse this desire, where I found the ability to push him off, I could never say. As soon as the tingling hit it's intensity, I suddenly forced him upward with one quick and violent motion. Colby stumbled forward, hitting the bed and turned just in time to see stream after stream of hot cum hit my chest. His eyes grew large as he managed to stand on wobbly legs and watch the events transpire before him. I clawed at the arms, watching as the last bit deposited itself onto me, and I felt a sense of serenity, satisfaction and guilt wash all over me. "Colby, I'm so sorry!" I exclaimed, nearly crying. Colby laughed a little, looking at the gooey mess on my chest. "That was cool, did it feel good?" I looked at him with my eyebrow raised in curiosity, his red face was beginning to return to normal and he seemed genuinely... happy? "Are you really okay? I asked bewildered. "Yeah I mean it hurt a little when you were all the way in but I'm okay. I think I'm going to be sore awhile though." He giggled, rubbing his butt and winking at me. I smiled, I wanted very badly to take him into my arms and hug him, but I didn't want to saturate him with my cum. "Can you get me a towel sweetie?" I asked, laughing a little and feeling a great sense of relief. "Yup!" Colby bounded out of the room and back towards the bathroom. I tried to catch a glimpse of his ass but he was too fast. I felt completely wasted, and there were few things in the world that could explain how at peace I was. As soon as he returned with the towel I took it with a word of gratitude and began to clean myself up. "When will I start making that?" Colby asked, sitting on the edge of the bed. "It's different for everyone, I was kinda late, I didn't start till I was fourteen." "I can't wait till I can do that." Colby grinned. "Oh it's overrated..." I commented, laughing a little. "So do you want me to do anything to you?" I asked, feeling a tad guilty that I had provided him with no pleasure. "Nah I'm cool. It's after midnight so I probably should go to sleep." I smiled, opening my arms as Colby walked over and embraced me tightly. I gently caressed his back, feeling so much love that I could barely contain it. "Do you mind if I look at your butt?" I asked. Colby looked at me with a slightly disgruntled appearance. "I don't think I want to do that again this soon." I laughed, "No, I just need to make sure I didn't hurt you." Colby shrugged, standing up and turning around for me. I spread his cheeks apart, his hole was certainly a little larger than it was before, but I didn't see anything except the sheen of the vaseline and what little cum had managed it's way out when I threw him off. I touched my finger to his hole a little, causing him to flinch just a tad, and upon drawing it back saw nothing. "It doesn't feel torn or anything?" I asked, completely bewildered by all this. "Nope it's just kind of sore. I feel like I took a huge dump." He giggled. I smiled, patted his bottom playfully and watched as he jumped in surprise. "Well I guess it's time for bed then." He smiled as we both climbed beneath the sheets. I had deposited the towel and jar of vaseline beneath the chair to deal with the next morning. As I wrapped my arm around him and his body conformed to my own, I found sleep all too easy.