Date: Wed, 9 Apr 2025 02:35:50 +0000 From: Skyler Fielding Subject: Helping a Rent Boy 03 Please, if possible, make a donation to Nifty. Without our support, Nifty won't be able to provide us with such wonderful entertainment. Note: If it is not legal to access gay adult materials where you live, please do not continue. The following story depicts a sexual relationship between a man and an underage teen. If this is not something you agree with or are not interested in, again, please do not continue. Adult male (21) / Teen boy (13) - m/t ====================================== It had been five days since Ryan joined me. We'd spent our days working out and teaching him some martial arts. I found him very dedicated to learning as much as he could. Ryan had never been to Chicago so we spent some time exploring the city. At night, we continued getting him ready for losing his virginity. Each night we moved to bigger and bigger dildos. Last night the dildo was just a bit smaller than my seven inches. I also made sure to get him to cum as many times as I thought he could handle. Last night, he came four times before rolling on his side and curling into a ball to fall asleep. This morning I couldn't bring myself to wake him at 5am like I normally did. By the time he made an appearance I had finished my workout and started on breakfast. "I smell bacon," said Ryan as he came up behind me and gave me a hug from behind. "Hungry? Again?" I asked. "Always," as the boy started putting plates on the bar. "Why didn't you wake me?" "After last night, I thought you could use the rest." "That last time I came I thought I was going to blow my balls out through my dick." "But did you enjoy yourself?" I asked. "You have no idea!" admitted with a huge grin. As we sat down to eat, my phone rang. "Just messenger them over as soon as you can." I told my lawyer when he explained that Ryan's ID and passport had arrived. He was also going to send over the offical copy of Ryan's Guardianship papers. "Everything okay?" ask Ryan. "Everything is great," I answered. "In fact, when you're done here, I need you to pack all those clothes we got you into the suitcase you'll find in your bedroom closet." "You're sending me away?" asked Ryan with a panicked expression on his face. "Why would I send a hot and sexy thing like you away? I'm a lot of things but stupid is not one of them." I announced as I put my hand on his back and rubbed him gently. "You and I are going on a trip." "Where to?" asked Ryan his expression brighting. "That's a surprise." "Oh come on, that's not fair," whined Ryan. "And who promised you life would be fair?" I asked sarcastically. "Now go start packing!" Ryan grumbled but went off to pack. While he was busy, I started making travel arrangements. During all of this, the messenger arrived with Ryan's documents. I put his passport in my travel bag that I always kept ready. When Ryan returned with his packed suitcase I handed him the ID. "Put this in your wallet and give me your old ID." He took the new ID and looked at it. "It's really true then? You really are going to take care of me now." "For as long as you want." Next thing I know, Ryan has his arms around me in a rib crushing hug. I hugged him back, rubbing it reassuringly. When the house phone rang, Ryan released me but still kept one arm around my waist. "That will be our car," I suggested. When we exited the lobby door, the driver was standing with the door open waiting for us. I noticed Ryan didn't quite know what to do with his suitcase. Leaning down, I whispered in his ear. "Just leave it there. The driver will take car if it." After closing our door and placing the lone suitcase in the trunk, the driver got behind the wheel and off we went. Forty-five minutes later, we pulled into the business terminal and pulled around in front of one of the many hangers where a Gulfstream G800 sat waiting for us. The pilot and co-pilot stood waiting on one side of the boarding stairs and the fight attendant on the other. I had flown with this crew before. They were one of the best. "We're flying in that?" asked Ryan like it was something that was going to fly us to the moon. "What? Not good enough for you?" I asked sarcastically. "You're not getting spoiled are you?" "This is so cool!" said Ryan after trying to punch my shoulder which I gracefully avoided. The pilot, Harold, came forward along with the fight attendant, Dean. Dean walked past us and took Ryan's bag from the driver which disappeared somewhere in the hold of the plane. "Nice to have you flying with us again Mr. Bartlett," greeted Harold as he extend his hand for me to shake. "I see you have a new ward with you this trip." "This is Ryan and I would like our destination to remain a surprise for him." I prompted. "I understand. I'll pass that along to the rest of crew. Please come aboard. We are ready to depart as soon as you are settled," announced Harold as he prompted us toward the stairs. I moved toward the stairs as Ryan ran up to walk by my side. "What's a ward?" he asked barely above a whisper. "Robin was Batman's ward," I whispered back. "I thought Robin was Batman's sidekick." "Okay, Dick Grayson was Bruce Wayne's ward." "You're not Batman are you?" asked Ryan as he ran ahead and up into the plane laughing all the way. I found him sitting in one of the first seats on the plane. Before he looked around and noticed the two sets of bench seats facing a table between them. The boy jumped up and took the seat closest to the window facing forward. "Can we sit here?" asked Ryan as he almost bounced in the seat. "You just want to be able to cuddle," I teased. "Well, duh." responded Ryan lookng around. "Is there a bed? I could join the mile high club." "Damn, you're a horny boy." "It's all your fault," teased Ryan as I sat down next to him. "Can I get you two something once we have taken off." asked Dean as he came and stood next to the pair. "Can I have a coke?" asked Ryan. "And some peanuts?" he added. "Please." "I'll have my usual, Dean." "As soon as I can, sir," said Dean as he moved toward the back of the plane. The plane moved onto the runway and was soon in the air. "You're still not going to tell me where we're going are you?" asked Ryan after Dean had served our refreshments. "I will only tell you it will take us about eleven hours to get there." "So there is a bed!" "What have I created!" Time passed slowly as it always does when flying, even if you are flying on a private jet. Ryan and I did make use of the bed but not to join the mile high club. About an hour before we landed, the two of us cleaned up and got back in our seats. As we flew into the island of Fiji, Ryan was glued to the window. "Is this Hawaii?" asked Ryan. "No, we are way south of Hawaii." "Can't you tell me where we are now?" "This is Fiji." "Where the hell is Fiji?" "Think east of Australia and north of New Zealand." "Why are we here?" "One of the schools I run is here. It's a really beautiful place." I answered. "I thought you might want to loose your virginity in paradise." "Tonight?" asked Ryan with a huge smile. "Do think you're ready?" Ryan looked back out the window as we approached the airport. "You're nervous about it aren't you?" I asked. "I guess." he answered still looking out the window. "We don't have to do it tonight or at all if you don't want to." "No, I want to," answered Ryan. "You're not going to leave me here are you?" I put my hand on the back of his neck as the plane touched down. I gently turned his head toward me. "Given what I've told you about myself, I can't blame you for worrying about that." I admitted then after a long pause. "I'm not sure why or how but I've gotten used to having you around. The last thing I want is to drop you off here or any where else." "Is that your way of saying you love me?" asked Ryan with his trademark grin. "I'm not sure it's love yet but I very much care about you. There is definitely no way I'm going to leave you anywhere unless it was what you wanted." "So we're really going to do it tonight?" asked Ryan as the plane came to a stop in front of a hanger much like the one we left from. "Only if you want to and you think you're ready." I got up when I noticed Dean opening the door. "Time for us to go." I lead Ryan off the plane. Customs and Immigration were waiting for us at the bottom of the stairs. The man checked our passports and then left. A man approached and introduced himself saying he was there to assist in our transfer. He then pointed to a car waiting near the plane. "That's my suitcase!" exclaimed Ryan when he noticed Dean putting the bag in the trunk. "That's the car that is going to take us to the heliport." "Heliport?" asked Ryan. "We need a helicopter to get where we're going." I answered. "At least, to get there quickly." When we got to the helipad, my Bell 206 was sitting there warming up. The driver transferred Ryan's suitcase to the back of the helicopter while I escorted Ryan to the front of the craft. "I get to sit up front?" asked Ryan with an excited look on his face. "I need you to be my co-pilot." Ryan's head snapped around to look at me so fast I though his head might snap off. "Co-pilot?" questioned the boy. "You're going to fly this?" "I am." I helped Ryan into one of the two front seats. I got him fastened in using the four point harness. Once set, I had him put on a pair of headphones so we could talk during the flight. I then walked around and got into the other front seat. Ryan watched with interest as I started flipping switches, pushing buttons, and turning knobs. "Can you hear me?" I asked turning to Ryan. Once Ryan nodded, I continued. "Some rules before we get going. First, don't touch anything unless I ask you to. Understand?" "Don't touch unless told to." Ryan answered as he looked around examining everything. As I started applying power to the rotors and the craft began to lift off. "Second rule, don't jump out when we're in the air." I made my communications with the tower and off we went. Once clear of the restricted airspace, I had some fun. Flying low to the ground, going up and over hills, slowing down and stopping at special landmarks, even flying sideways at times. It was all worth it to see the huge smile on the boy's face. Once we got to the right spot on the coast, I turned and headed out to sea. It was a short ride to the island that housed the school. "This is where we'll be staying," I stated as we cut close to the school. "It used to be a dive resort until it went out of business and I bought it." "So you own the whole island?" asked Ryan in disbelief. "It's really not that big. Here, I'll show you." So around the island we flew. As we did, I pointed out the different points of interest. The soccer field, the tennis courts, the school, the dorms, and many other features. "Before we land, I need to make sure you understand a few things," I started. "There are currently eighteen boys here and I have had sex with a few of them. When we land, we will draw a crowd. There will be more than a few hugs and even one or two kisses. None of these boys have made me feel toward them as you have. None of them will sleep with me tonight or any night we are here. I am going to make it clear that you are with me, that you are very special to me. You will be leaving with me when I go. You going to be okay with that?" "Depends how cute they are." answered Ryan with a sneaky grin as the choper touched down. Boys were already running toward us as the rotors slowed to a stop. Before I helped Ryan down from his seat, I took him in my arms and kissed him deeply. "That should send a pretty clear message," I whispered into Ryan's ear. Ryan met my gaze, he smiled, and kissed me back even deeper. This was accompanied by a chorus of wolf whistles and "ohs." I set Ryan on the ground but kept an arm around his shoulders. As the boys approached, they kept a little distance. Even the ones I'd had a relationship with did the same. I couldn't help but detect a little disappointment on their faces. "This is Ryan and he is very special to me." I announced. "I want you all to make him feel welcome. We'll be here for a few days then we'll be moving on." Boys started coming forward and either shaking Ryan's hand or giving him a hug. More than a few also gave me a hug. An adult pushed through the crowd, "Welcome back, Chase. Is there anything you need?" "Hello Devon. There is a suitcase inside. If you could make sure it gets up to the house, please." "Right away, sir." "Is there anything I need to know?" I asked. "Everything is going as you would expect. Do you plan on joining us for dinner?" asked Devon. "Actually, could you have the chief prepare something special and have it served for the two of us up at the house?" "Not a problem, sir." "Around seven?" "As you wish," answered Devon as he turned toward the helicopter to collect Ryan's bag. "Okay boys," I spoke loud enough to get everyone's attention. "Ryan and I have had a long trip and I want to get us settled. I promise to spend some time with you tomorrow." I put my arm back around Ryan and lead him away from the crowd that was already breaking up. I led the boy along a twisting path through dense tropical foliage up toward the house I maintained here. Once inside, I showed Ryan around. We found Ryan's bag in the master bedroom. Obviously, Devon understood what type of relationship the two of us had. The two of us worked together to get his clothes put away. Once done, we went downstairs to find Devon had left a plate of sliced pineapple on the kitchen bar along with a glass of the Chief's jet lag cure. As we sat eating pineapple and drinking the chief's cure, Ryan turned to me and asked, "Are we like boyfriend? Like exclusive and stuff?" "Is that what you want?" I asked. I had noticed a few of the boys whispering in his ear as they gave him a welcoming hug. Right after he would blush, look over toward me, then move on to the next boy. If I know my boys, and I do, they were most likely suggesting some very naughty things they wanted to do with Ryan or with Ryan and I together. Given how quiet he'd been since then, I was wondering if he had been thinking about such things. Either that or he was jealous of some of the boys. "I don't know," he said over barely a whisper. "You've been thinking of what the other boys have been suggesting?" "I don't know." "Before you left home, all you really fantasized about was boys around your age. Maybe a high school senior that was super cute. Am I right?" Ryan only shrugged in answer. "Remember Ryan, this is about you not me. If you would rather have a boy your age be your first..." "No, I want you to... you know..." "Be your first?" Ryan nodded if only slighly. "But after that you would like to branch out?" "You won't be mad?" asked Ryan. "I would love to keep you all to myself but I don't own you Ryan. If you want to try being with a boy your age, I'm not going to stop you. I would like to ask a favor if you would okay with it." "I bet you want to watch, you perv!" suggested Ryan with a sarcastic laugh. "Actually this perv hadn't thought of that. It would be hot watching two cute boys fuck each others brains out," I admitted. "Actually, I was wondering if I might join in the fun once and a while." "See a perv!" accused Ryan as he got up and came around the bar to climb up onto my lap. "Can you really fuck two boys at once?" "Not with just one cock, but I'd sure love to take turns," I admitted. "Sounds hot!" giggled Ryan right before he started french kissing me. As he wiggled around to get comfortable he reached down and started rubbing my quickly hardening cock. When he pulled away, "And you call me a perv." I said as I started tickling his sides. He squirmed as his laughter filled the house. When I stopped, he rested his head on my shoulder and went back to rubbing my cock through my shorts. Once he got me close to completely hard, "Can I suck it?" Ryan asked without looking up. "I don't think I've ever said no to a blow job from a sexy boy. Certainly not one as sexy as you!" Ryan dropped down off my lap and I started to unfasten my shorts. "No, not here," said Ryan as he took my hand and started to pull. I followed as he led me back up the stairs to the master bedroom. Once there, he pulled his shirt up over his head before looking back over his shoulder. "Strip!" he commanded as he drop his t-shirt and kick off his sandals which were quickly followed by his shorts. I quickly followed his example as he climbed on the bed on his hands and knees and wiggled his butt at me. "Such a sexy boy." I said out loud if only to myself. Ryan giggled as he stood up on the bed with his back to me and started to slowly pull his briefs down while doing a little dance. Once my briefs dropped to the floor I layed down on my back and watched Ryan's sexy strip tease. Once his briefs dropped to his ankles, he kicked the briefs across the room before turning around toward me and continuing his dance. As he did I couldn't take my eyes off his hard five inch cock swinging back and forth. He smiled and knelt down between my outstretched legs. He reached out and took hold of my seven inch cock and held it straight up. He leaned over and licked up the shaft. He stroked it a couple of times before looking up at me. "Are you sure it will fit?" "All of it? In your mouth? Probably not. At least not without lot of practice." "Not my mouth silly, my butt!" exclaimed Ryan slapping my thigh. "Oh that," I teased as he leaned over and took the head of my dick in his mouth. I'd sucked his dick often enough and he'd jerked mine but he'd never sucked me. He must have been paying attention because he was doing a great job as he went up and down on the first three or four inches of my cock. He took my dick out of his mouth and looked up at me. "Well? Will it?" he asked as he went back to sucking me. "I'll start with my fingers, like with the dildos. It might stretch you just like when we went to a new dildo but it should fit fine." I couldn't help but groan as I felt my cock hit the back of Ryan's throat. Ryan came off my dick and coughed a few times. "Don't try and take too much." "But I want to make you feel good." he admitted before going back to his blowjob. "You're doing great! Plus watching your cute month wrapped around my dick is really hot." Ryan looked up at me and did his best to smile around my dick. He must have worked on my dick for a good five minutes before he stopped, crawled up next to me, and rolled over on his back. "That made my jaw ache." "You did great!" I complimented the boy as I wrapped my arm around him. "You just need more practice. I would be happy to volunteer." Ryan rolled over and laid his head on my shoulder, wrapping an arm and leg around me. He briefly rubbed his hard dick against my thigh. "Could we do it now?" he asked after greatly kissing my chest. "You want me to make love to you right now?" "I've waited like a week." I rolled over toward him so I was almost facing him. I ran a hand down his side to his hip then over his smooth butt to the back of his upper thigh. My fingers slipped into his crack. I let the tip of my middle finger tickle his tight young hole. Ryan moaned and hugged me tighter. "Please," he begged in barely more then a whisper. It was at that moment we both heard a knock on the front door. "Chase, it's seven and I have your dinner." came Devon's voice from below. "You've got to be kidding me!" grumbled Ryan. "Sorry Ryan seems like we're going to have to wait just a bit longer." I said as I gave his tight hole a gentle poke. "Go ahead set things up Devon. We'll be right down." I called down. Ryan groaned again and squeezed me even tighter. "This is so unfair!" whined Ryan. "I know! You got me all excited with that great blow job and now I have to wait to see if all my hard work on that fine ass of yours was worth it." I teased. "After dinner, Ryan, I promise to make it worth the wait. I'll do my best to give you an experience you will remember for the rest of your life." "Promise?" "I'll do my best. After dinner we'll watch the sunset while Devon clears away dinner. Then I'll carry you to our bed and make you a very happy young man." Ryan rolled away, got off the bed and went looking for his underwear. "Don't bother with underwear. You just need to wear your shorts." "Perv. You just want to be able to get to my ass faster!" accused Ryan. "I thought you were in a hurry?" Ryan answered me by wiggling his bare ass at me as he bent over to retrieve his shorts. "I so can't wait to hear you moan as my dick goes up that hot sexy hole." I admitted. "As long as I'm moaning and not screaming." "The only screaming I want to hear from you is 'harder,' 'faster,' and 'deeper!'" "Stop!" pleaded Ryan as he fastened his shorts over his rock hard dick. "That guy is down there and I don't want to have a boner." "Devon has seen more than a few boy boners. He's definitely sucked several, too. I wouldn't be surprised if he'd let a few of the boys fuck him." "He let's the guys here fuck him?" asked Ryan more than a little surprised. "Devon is a dedicated bottom. He loves getting fucked." "Have you fucked him?" "He's too old for me." "Perv!" giggled Ryan as we made our way downstairs. Devon was waiting at the open front door holding a large serving tray under his arm. "Just let me know when I can clear up." said Devon then he turn and left closing the door behind him. Ryan ate the fine dinner faster than I thought humanly possible. I tried to keep up but there was now way. I was about half finished when he turned to me and stated, "I'm done!" "No wonder you give such great blow jobs, you're a human vacuum cleaner." "If you ever want another one, I need you to fuck me. Now!" "Such an impatient boy. Besides, I'm not going to fuck you. Not tonight. Not ever. I'm going to make love to you." Ryan got up and came around the table. He leaned over and wrapped his arms around my shoulders. He squeezed me tight and whispered, "But after tonight what if I just want to get fucked?" "I'm sure we can arrange that for such a naughty boy." I answered. "Now, follow me." I got up from the table and headed upstairs but instead of turning toward the bedroom, I turned the opposite direction. As I approached the sliding glass door, I unfastened my shorts and let them drop to the floor. I stepped out of them and opened the door. Once outside I turned on the hot tub and got in. A naked Ryan, immediately sat down next to me. I reached over and pulled him across his lap. I pulled him tight to my chest. When he looked up at me, I leaned down and started kissing him. After exploring his young mouth, I stopped and hugged his young smooth body against mine. "So this is really going to happen?" "Do you still want to?" Ryan pressed the side of his face against my smooth chest and nodded. "Watch the sunset," I directed as I ran my hand up his smooth muscled leg to his young tight ass. His firm butt cheek almost fit in my outstretched hand. The sky turned from blue to yellow as our tongues danced in and out of each other's mouths. As the sky went from yellow to orange, Ryan rested the back of his head on my shoulder as we both watch the sun slowly sink down into the ocean painting the sky from deeper orange to red then purple until the sky turned black. While we watched I spread my knees apart letting his ass drop down between my thighs. As I held my hand in the middle of the boy's back, I ran my other hand from his ass over his thigh to his crotch. I gently rolled his smooth sack in my fingers before going up to hold his now stiff rod and gently stroke it up and down a few times. As the sunset painted us in red light, I slid my hand down between his thighs and up his crack where I pressed my middle finger into his tight smooth hole. Ryan moaned as he usually did when my finger first worked it's way into his tight heat. I slowly worked my finger deeper. I fucked him gently, in and out until my knuckles pressed into his cheeks. When I curled my finger pressing it into his prostate, Ryan arched his back and I saw cum float to the surface. "Someone must have been horny." I observed. "You have no idea how horny I've been since we got here." "It's okay, I've been super horny, too. The thought of taking your cherry tonight isn't helping." "Nasty perv," teased Ryan as I withdrew my finger. I moved my arm under the back of his knees and lifted him from the tub as I stood. Once I'd climbed out of the tub, I set Ryan down on the deck. I tossed him a towel from the nearby pile and we started drying each other. Once we were both reasonable dry, okay not really, I just didn't want to wait any longer. I took Ryan's towel and tossed both in to a nearby hamper. I then picked the boy up again and carried him to our bed. As I made my way, Ryan leaned up and licked my nipple. When I got to the bed, I laid the boy on his back and then crawled on my hands and knees until I was kneeling over him. Ryan spread his legs to make room for my knees. He reached up to put his arms around my neck but I took his hands in one of mine and held his arms stretched out above his head. I leaned down and kissed him deeply and passionately. I went lower and used my tongue on first his right nipple and then his left until they were both hard like pencil lead. I then nibbled on the hard tips ever so gently. Ryan groaned and his breathing got heavier. I was determined to make him cum once more before I got my cock in him. I kissed him on the mouth again pushing my tongue into his mouth as deep as I could. Ryan responded sucking on it like he had my dick. After letting him suck my tongue for a moment, he tried to push up and rub his boner against me. Using my free hand, I gently pushed his ass back down on the bed. I started softly kissing and licking his face. The boy started to giggle and turn his face away from me. I moved to his neck and continued kissing his smooth soft skin. The boy kept pushing against the hand on his hip so he could meet that primative need to fuck something with his pulsing cock. I moved down from his neck, back to his nipples which I went back to kissing, licking, and nibbling. I then licked first one hairless arm pit and then the other. The pressure against my hand increased and I decided it was time to give him some relief. I rubbed the head of my seven inch erection along his rigid five inches covering it with my precum. I removed my hand and he immediately started rubbing his boner along mine. I leaned down pressing my chest to his, using my weight to hold him down on the bed. When he could no longer rub himself against me, he groaned. "Come on, this is so not fair!" complained Ryan as he tried again to rub his throbbing dick against me. "What's the matter? You seem all hot and bothered." "You think?" "Is it something I've done?" I asked with a big smile then kissed him before he could answer. I rubbed our dicks together a couple of times. "Do you want to cum?" I asked. "Please!" begged Ryan. "Do you want to cum for me?" humping his cock a bit more. "I'm so close." whined Ryan. "Do you want to cum between us or in my mouth?" "God yes, suck me! Suck my dick you perv!" I reached over to the bedside table and removed the bottle of lube from the drawer. I slid my body down his, making sure to drag his dick over my abs and then between my pecs. Taking his balls in my mouth I sucked them gently. "My dick! Suck it! Please!" I put my hands under his legs and pulled them up then pushed them up toward his head. I put some lube on the tip of my middle finger. I licked his taint, up his balls, then up his cock to its head. As I sucked the precum off his head, I started working my finger into him. Once I got past the second knuckle, I pushed my finger in all the way and curled my finger into his prostate. At the same time, I took his cock into my mouth and took him deep until my nose was pressed into his pubs. "Fuck! Yes!" exclaimed Ryan as I gently started to fuck his tight virgin hole with my finger. I bobbed up and down a few times edging the young boy. I added more lube to two fingers and worked them back into his smooth hole. Ryan's hands reached out and grabbed a handful of sheets so tight his knuckles turned white. I ran my tongue around his head savoring his sweet precum. I twisted my fingers around as I worked them in and out of his tight smooth ass. "Please! I can't take any more!" pleaded Ryan. I took his throbbing cock from my mouth and looked up at him. "Oh, we're just getting started my young friend." I chuckled. "I am a perv after all." "God, I'm so fucked." exclaimed Ryan with a groan. "Not yet! But you will be soon." I said as I pressed my two fingers hard into his ass. "Please! Chase I'm begging you!" "So you need to cum?" "Yes, please!" "You want to cum one last time as a virgin?" I asked. "Please, my balls are going to explode." "We can't have that." I took my fingers from him, added more lube and gently worked three fingers into him. I then went back to sucking his slim dick. I worked him up and down using a slow steady pace. Using my fingers I worked his hole using the same rhythm. "Oh fuck! Yes! I'm... Fuck!" Ryan's body stiffened. His balls pulled up even tighter than normal. A blast of cum hit the roof of my mouth followed by a second equally forceful shot. Before I could swallow, a third smaller shot of sweet boy juice coated my tongue. I swallowed quickly as the boy's dick continued pumping smaller less powerful shots over my tongue. When the boy's cock stopped filling my mouth, I reached up and wrapped my hand around the back of his head. I reached up with my face as I pulled his toward mine. Pressing my mouth to this, I shared his load with him. As he realized what I was doing, he moaned and wrapped his arms and legs around me. "God," swore Ryan. "I've never cum so hard before. You're the best perv in the whole world!" As Ryan lay there panting, his chest heaving like he'd just sprinted a mile. I shifted up on my knees, looking down at the sexy young teen all flushed from our sex. His slightly softening dick, throbbed quickly in time with his heart beat. As I admired Ryan's smooth athletic body beneath me, I decided it was time. Time to take the boy's cherry. The thought alone caused a drop of precum to drip down onto the boy's hairless ball sack. Normally, I would let a boy sit on me when he lost his virginity. It let him take me as fast or slow as he felt comfortable. Considering I'd spent several days preping Ryan. Considering I'd gone night after night getting him off over and over without getting off myself. Considering that same boy was laying there with that sexy little grin on his face, like he knew what I had in mind. "You realize that was the last time you came as a virgin, right?" I asked the boy as I squeezed lube on my hand and started coating my hard cock with it. Ryan noticed what I was doing. "Finally," he giggled as he grabbed his legs behind his lower thighs and pulled his knees up toward his ears. "Get that big perv dick inside me." I pushed his legs back lifting his ass off the bed. I shifted until my gland touched his tender opening. "Ryan?" My voice turning serious. When he met my eye, I continued. "Are you sure about this? Once it's done it can't be undone." I applied a little pressure to his boy hole so he would understand what I meant. "I've been wanting this since I first saw you naked and all dripping wet. I so want your sexy body on top of me with that huge dick inside me. Don't you know I was always thinking it was you inside me when you used those dildos on me?" He reached up and pulled my head down and kissed me. As we kissed, I pressed forward stretching him just a bit. "Remember what you learned from the dildos. Let yourself relax. You're going to feel some stretch," I pushed again feeling his hole start to open and let me in. "Let me know if it hurts too much and I'll..." "Shut-up and fuck me already!" I didn't need anymore encouragement. I put some weight into it and sank about two inches of my stiff rod into the no longer virgin hole. "Fuck, yes!" Ryan screamed. I pulled out an inch the push two more inches in. Ryan's head pushed back into the bed. The boy looked up to me and gave me his trademark cheeky grin. "You liking that?" I asked. The boy only nodded as I withdrew and then push more of my cock into him. Ryan's body stiffened and I saw his boner pulse as a big drop of precum dripped onto his belly. "Do you want more?" I asked pulling out slightly. "Yes, please give me all of it." I pushed, sinking another half inch into his hot tight passage. I held it there as I leaned over him and kissed him deeply. I worked my dick in and out but didn't go any deeper. "Is it what you expected?" I asked the boy as I pushed in a bit more and held it there. "Is it all the way in?"asked Ryan with closed eyes. "I'm only about half-way." I felt his fingers dug into my shoulders as I started to fuck the boy with only half my dick. "You're going to make me cum without touching my dick." "Do you want me to go deeper?" I asked. "Yes, but go slow." pleaded Ryan as he pulled me down for another kiss. I worked my cock in and out slowly going just a little deeper with each thrust. Each inward push drew a cute little 'oh' from the boy. His head rocked from side to side. He moved a hand to his rock hard cock and started to stroke himself in time with my thrusts. After fifteen or so minutes I'd gotten maybe five and a half inches into his smooth firey insides, his jerking sped up until it was almost a blur. "Fuck! Fuck! Fuck!" Ryan literally screamed as he painted his chest with a layer of fresh boy cum. "You were only allowed to scream 'harder' or 'deeper' remember?" I teased once Ryan had come back to Earth. "Don't blame me!" Ryan said slapping me gently in the shoulder. "It's all you fault." "So how was your first cum as a non-virgin?" "Fucking great!" I withdrew from his small smooth hole. The look of disappointment on Ryan's face was obvious. "Don't worry my sexy young man. I'm not done with you yet." I took Ryan by his narrow hips and flipped the boy over onto his stomach. Ryan let out what was something between a grunt and a laugh. I pulled the boy up onto his knees. Ryan pushed up on his hands until his back was parallel with the bed. I moved forward between his outstretched calves. As I got closer, I realized his hole was too low for me to enter. I took hold of his hips and lifted. His legs coming together as I moved my knees outside his smooth calves. I spread my knees wide until the height was right. I cupped the boy's narrow smooth ass, each cheek in one hand. "God I love a boy's ass." I thought to myself as I squeezed the firm muscle. I ran my hands over his back. Down the back of his wonderful thighs, over the front of his thighs and back to his exceptional ass. "Ryan, I would love to lay with you naked all day, every day. You are just amazing!" Ryan looked over his shoulder and smiled. "Are you just going keep touching or get back to fucking?" "I don't know. You have such a hot body it's hard to resist." "Oh, please!" as he dropped his head and shoulders to the bed. "Just get on with it." Ryan moaned as I used my thumbs to spread his smooth cheeks and he felt my dick touch his hole. Before I pushed in, I marveled at how his just fucked hole had snapped tight again. I entered slowly, not wanting to hurt him. I worked in and out slowly until I was back at my orignal depth. As I took hold of his hips to slowly work myself deeper, Ryan pushed back sinking a half inch into his ass. "That's it Ryan. Show me how much you enjoy that big cock inside you." The boy began rocking back and forth each time pushing more of my tool into himself. With each backward push this cute grunt escaped the boy. It didn't take him long before his ass cheeks where pressing hard into my crotch. "That's all of it my young lover. "Oh god, it's so big!" "Do you want me to take it out?" "Don't you dare!" "Then show me how much you're loving it." Ryan took a relaxing breath before rocking back and forth. Each time he pushed back into my crotch, he would push back hard and let out that cute grunt. I reached around and took hold of his cock. It had gotten semi-soft after his last climax. I was happy to feel it back to full hardness. As soon as I wrapped my hand around his stiff boy dick, he started pushing in and out of my fist. In doing so, he continued to fuck himself on my cock. His grunting grew louder as I sensed another of his climaxes approaching. I started meeting his backward push with a foreward push of my hips, pushing my cock into him even harder. I aimed my boner down, aiming at his prostate. "Oh god it feels so good!" Ryan exclaimed. "You like that?" "Yes! I'm going to cum again!" "That's my big boy. Blow your load in my hand." Ryan's pace increased again. His grunt turned into long moan. "Oh god, oh god, oh god." chanted the boy. He pushed into my hand and started to fill it with a nice load of boy cum. "Fuck!" moaned Ryan as he collapsed onto his stomach. I followed him down, keeping my dick snug in his tight boy hole. As I laid my weight on the boy's back, I continued to pump in and out of the boy's cute butt. "Are you trying to kill me?" moaned Ryan. "I promised you would never forget this." I wrapped my arms around the boy's chest and rolled us over so Ryan was laying on my chest. I shifted our legs around until my legs we're between his outspread long legs. I then continued my slow fucking of the tight hole. "Oh!" cried the boy each time my cock thrust across his prostate. I ran my hands over his smooth boy body. His developing pecs, his flat stomach, his soft pubs, his bare arm pits, neck and arms. His recently spent cock had been softening but quickly started to harden again when I stroked it a few times. The kid was a machine. I turned his head and sucked his tongue into my mouth. I wrapped my arms tight around his body, holding him tight to my chest. I then started to fuck the small boy. If I wasn't an experienced boy lover, I would have blown my load into that tight virgin hole long ago. But this wasn't the first cherry I'd popped. Honestly, I'd lost track of how many boys I've had. I'd learned long ago to pace myself. To do my best to make it more about the boy's pleasure than mine. But as I looked into the boy's eyes, glazed over with that dreamy fog of lust, he was different. It wasn't his sexy smooth body or his tight hairless ass. There was just something about him that cut right through to my soul. Ryan wrapped his arms around mine. He rested his forehead against my cheek. "Promise... we'll do... this... alot... more!" pleaded Ryan between moans. "That's an easy promise to make." I answered honestly. "We can do this as often as you want." "So... I'm a... good... lay?" "One of the best I've ever had." Again, an easy honest answer. "Seriously?" asked Ryan followed by a long moan. "God! You're going to make me cum again." "I hope it's right as I'm filling you with my cum." "You're going to cum inside me?" ask Ryan. "If that's okay?" "So you're going to breed me?" "You watch too much porn." I stated. "But yes if it's okay with you." Ryan started kissing me again. This time sucking my tongue into his mouth. I started thrusting into the boy with a sudden desprite need. I can't help but admire his stiff young cock as it bounced up and down with each of my thrusts. I reached down and took his cock in my hand. "I'm going to breed you my boy." I growled as I increased my pace, thrusting harder and faster. "Deeper!" pleaded the boy. "Turn around and sit on me." I ordered. "You want me to ride you?" "Absolutely." The boy pushed himself up, with my help, keeping me firmly inside his hole. He put his small hands on my muscled thighs and started riding me. Letting his weight force me deep into his hot tightness. I ran my hands up and down his smooth perfect back. I cupped his small tight ass in my large hands, savoring the smooth firm flesh. "You really love my butt, huh?" asked Ryan looking over his shoulder. Again that trademark grin I'd come to love so much. "You have no idea." I agreed as I realized how close I was to coming. "Turn around. I want to see your face when I cum in that great ass if yours." Ryan got up on his knees, letting me slip out of his hole with a pop. He turned around repositioning himself over me. I reached down and grabbed my very hard cock and pointed it up toward his waiting hole. He reached under him and took the end of my cock in his small hand and placed it at his opening. It surprised me when he let the shaft slide all the way in with one smooth drop of his weight. "Fuck me!" he screamed, immediately put his hands on my pecs, and started fucking himself. "Lean back and put your hands on my thighs." I suggested. Ryan looked at me puzzled. "Trust me." The fucking paused while he ackwardly moved one hand to a thigh followed by the other. He leaned back, placing his weight on his hands. The position stretched out his supple frame, emphasing the boys smooth skinny body. I ran my hands over his chest and stomach. I will never get tired of a sexy young body like Ryan's. "Now ride me." Ryan shifted off his knees until his feet were flat on the bed. He then started to lift up and down on my now very hard cock. This position put more pressure on his prostate than any other position we'd tried so far. Ryan's boner dribbled a drop of precum each time my dick crossed over his prostate. "Oh god! You really are trying to kill me!" exclaimed Ryan though he didn't stop riding me. After what felt like forever, I reached out to take hold of his throbbing cock. "No, don't. I'm really close." said Ryan slapping my hand away. "I want to cum when you do." "I'm close, too." I admitted. "Just go a little faster." The boy started going up and down a little faster. Precum started dribbling down is cock as it throbbed above his thin line of pubs. "Oh god!" screamed Ryan as he shifted into high gear. His hips started bouncing up and down. "Fuck... fuck... fuck..." The boy chanted each time my dick passed over his prostate. I watched his cute five inch boner bouncing up and down, slapping against his flat stomach leaving a large splash of precum there. I grabbed the boy's hips and started lifting him up then slamming him down on my cock. "Yes! Breed me!" Ryan screamed so loud I'm sure the whole island heard. "Breed me, you perv!" The boy started shooting cum all over my chest and abs. It was quite the sight the boy slamming up and down as his untouched cock shot cum all over me. It was such a hot image that it pushed me over the edge. I pushed him down hard and started filling the boy. Ryan collapsed onto my chest panting heavily as I finished emptying my balls into the boy's skinny ass. I took his face in my hands and kissed him deeply. "You're my boy now." I whispered in his ear my lips brushing lightly against his small ear. I ran my hands over his sweaty back then down to his ass. I held the smooth butt in my hands as Ryan's breathing started to return to normal. He looked up at me, "Promise me I can stay with you forever." "For as long as you want." I responded giving his butt a gentle squeeze. The boy cuddled into my neck and promptly fell asleep. I held the boy close to my chest and gently rubbed his back, Even though I'd just had a huge climax, I remained hard and lodged deep inside his hole for quite sometime. I have to confess I did think about rolling the boy onto his back and starting to fuck him again. But I was a little bit worried I might actually fuck him to death. "Oh, well," I said to the ceiling. "Maybe tomorrow." ====================================== Please feel free to contact me with comments or suggestions at MyStories@writeme.com. I'd love to hear from you! Session ID: I'm not always online but I will responded if messaged. 057341a286d568bd13137c1b29e56924b80c334baef8898ed5e0fa67128d26834b