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Tape 3 Hard Lessons TEACHING MY GRANDSON

Jack was pretty gutted when he didn’t get the job he’d hoped for. He’d worked so hard to prepare and present himself as best as possible, but in... the end, it didn’t work out. Jack had always challenged himself and was no stranger to defeat, but something about this one stung a little bit more. Jack’s grandfather had done so much to help him and he really valued that time together. In a way, he felt like he wasn’t alone in the interview or anything else because the two of them were a team. He felt like he was standing on the shoulders of the giant that was Mr. Charger and that would help him go farther than he imagined. Of course, the hard lesson he had to learn was that he was his own man at the end of the day. With all the love and support of those behind him, he was going to be judged on his own merits. As his grandfather read the letter of rejection, he felt embarrassed that such a powerful and successful man as Mr. Charger had to be part of his failure. He didn’t want to disappoint himself, but Jack didn’t want to disappoint his grandfather even more. When Mr. Charger could see the boy beginning to sink deep into the office chair, he immediately knew they had to course correct. No longer was the task about jobs or interviews or preparedness, but it was about making sure Jack knew he was still his special little guy. Mr. Charger pulled Jack over to him, letting him sit on his lap as he’d done when he was younger. He put an arm around him and told him how special he was. He knew he had to make Jack feel better any way possible. And lately, he’s discovered something that always puts a smile on the young man’s face… Standing up, Mr. Charger gave Jack a kiss on the lips before bending him over the desk. It was sudden and fast, but it was enough to let Jack know what was coming. He didn’t have to think about the job or the letter, or anything else but what his grandfather was doing. Mr. Charger pulled down Jack’s pants, getting a close view of his soft, smooth ass. He kissed it softly at first before diving his face deep between his cheeks. “Isn’t this better?” the grandfather asked, smiling and looking up at his boy. Jack couldn’t help but crack a smile, appreciating that the older man was pulling out all the stops to make him feel good. Mr. Charger’s tongue moved over Jack’s hole with expert precision, both tickling, teasing, and gently moving inside. Jack couldn’t help but moan, feeling his loins swell with excitement. He wanted to feel his grandpa inside him and to forget all about the letter. And Grandpa Charger knew that. Pulling out his cock from his pants, the older man could sense the boy’s desire to submit. He needed to let go and think about nothing else but an intense pounding. He slid the tip of his member against Jack’s hole, feeling him come back on him ever so slightly, as if he was beginning to be penetrated with his ass. Mr. Charger took off the remainder of his clothes, put a hand down on Jack’s smooth, youthful back, and plunged himself deep into his grandson’s guts. Jack tried to contain his moans, not wanting to alert anyone nearby to the fucking occuring in his grandfather’s office. Mr. Charger, on the other hand, seemed to have no care in the world but his boy’s needs. He worked him slowly, fucking him with gentle thrusts at first, giving him a chance to get used to the older man’s thick, throbbing member. But once Jack fully relaxed, the older man held nothing back from his boy. The first aggressive thrust was a shock. Jack did not expect to be so roughly fucked by the older man, but he was instantly grateful. He felt completely taken and dominated, feeling his bare cock move inside his hole and slam against his prostate. Jack stroked himself between the desk and his body, loving every hard push the older man gave him. The furious pounding was almost more than Jack could handle, but he didn’t dare ask it to stop. He looked back at his grandpa, seeing the powerful, handsome, unstoppable man he’d always known and loved. And enduring the full force of his fucking, he knew he was special. He knew he was protected and cared for. That even now as he struggled to take the onslaught of deep penetrations, it was he that Mr. Charger was performing for. Jack wanted to feel his grandfather breed him more than anything else he’d ever wanted. More than any job or trophy or approval. Knowing he could have his grandfather right there inside him, with him, injected him on such a profound, natural level… it was the ultimate prize in life... [Read more]

Tape 2 Pumpkin Carving MY BEAUTIFUL BOY

I don’t see my uncle all that often. It seems like there’s a rush of holidays and birthdays, all finishing with Christmas, and it’s not until th...e next fall that we all start seeing each other again. It’s not really intentional. Life just gets busy. And family time is not always high in my priorities. I never think about it too much, but I can tell my uncle Matthew notices. He’s always telling me and my cousins how much we’ve grown and how handsome we are. I don’t know when the change happened from being “cute” to “handsome,” but uncle Matthew never misses the chance to tell us. Uncle Matthew is very handsome, himself. He’s got a perpetual tan, muscular body, and the face of a movie star! Even our cousin, Jack, is quite the looker, too. I’ve always felt a little dopey around him, not really sure what to say or how to respond. And as I’ve gotten older, he’s only shown more and more interest. I can’t say I don’t like it. I’ve often fantasized about catching him coming out of the shower or returning from the gym. It seemed wrong, but I couldn’t help it. When the leaves started to turn and fall was reapproaching, I knew that I was going to see him again. I got excited, but I also had no idea what our interactions would be like. It was right after Halloween that I showed up with my friend, Tom. We were just going to say hi, hang out for a bit, and go into town when we saw some pumpkins sitting on the stoop. They weren’t carved or anything, clearly put out for Halloween but never decorated. It felt like a shame to put them out completely blank. I asked my uncle if we could carve them up and a peculiar sort of smile crossed his face. His smile was always disarming, glowing white and bright. But something about the look in his eye surprised me. He said yes and Tom and I brought in the pumpkins to begin working away. Tom and I were being dumb and talking about what we were going to carve and such, still wishing it was Halloween. We went to look for a knife and some towels and when we got back to the pumpkins, my uncle was standing there, waiting for us, still with that peculiar smile on his face. “Boys, come here,” he began. We walked over, waiting for him to simply just remind us not to make a mess or clean up after ourselves. Instead, he mentioned something about a “fall male-bonding harvest ritual.” It sounded like a joke he was setting up, one of my uncle’s attempts at silly humor. But when he explained that it’s done completely naked, I felt my face flush red. Completely naked? Was he being serious? I watched in disbelief as my uncle began to unbutton his shirt. I could tell Tom was on board immediately. His face lit up and his horny, “say yes” attitude came right out. For me? I was nervous. I’d never seen my uncle naked before. And he’d never seen me naked! I kept waiting for the moment when it was revealed to be a prank, but when uncle Matthew stripped down to his underwear, I knew he wasn’t kidding. He urged us to do the same. By the time I was just starting to take off my sweater, he was completely naked! There I was, just a foot or two away from my uncle Matthew! Naked! He was insanely good looking. Better than I had imagined. I had seen him in the pool and on the beach a handful of times growing up, but I didn’t see more than just his muscular chest and arms. Now, I could see every inch of him. I couldn’t breathe or speak. I looked to Tom for a sign of what to do, but he was already all in. He stripped off his clothes and stood naked beside me, ready for whatever my uncle had in store for us. Apparently while we were running around looking for supplies, uncle Matthew had already carved a hole in one of the pumpkins. I had seen things online of people fucking pumpkins, but it seemed like a meme or a joke, not something people actually did. But as my uncle explained his “fall ritual,” it became clear that that’s what he wanted us to do. It felt strange to be talking so frankly with my uncle. He wasn’t a saint, but we’d just never had that kind of conversation. Sex was just not something we ever discussed, though looking like him, it was always on my mind. So to have him positioning me and my friend into position, it was surreal. Uncle Matthew had me lean over the pumpkin, placing my dick just above the hole. My bare ass was outward facing him, and before I knew it, he had his face right into it. Uncle Matthew! He kissed my ass cheeks, even tonguing my hole. It felt so weird, but I really liked it. He seemed to really love what he was doing, and it felt really good. I looked at Tom, seeing him stroke his cock watching me get eaten out by my uncle. I felt myself get hard, too. I reached a hand out to touch Tom’s cock, and as I did, my uncle put his hand on mine. He stroked it, teasing me and getting me excited before placing it in the hole he’d carved. The pumpkin was cool and gooey. I didn’t know if I should like it, but it felt good. Uncle Matthew pushed me into it, guiding me back and forth as I simulated fucking. As I kept going, it got warmer… and felt really nice. Tom watched and I played with his cock as my uncle continued to kiss and lick my ass. I felt like I was dreaming! This was not at all what I thought this fall would bring! Just when I thought it couldn’t get more intense, I felt my uncle’s finger going inside my ass. It was slow and smooth, but unexpected. I felt my insides clench around him, seemingly hugging him with my hole. He slid it back and forth gently. It felt so nice, but I couldn’t stop thinking about the fact that this was my uncle! I didn’t want to admit it to myself, but I wanted more. I looked at Tom and he saw my mouth open and drooling. He stood up and put his cock in my mouth. It tasted great. I’ve never sucked his cock before, and honestly never thought I would. But with everything else going on, somehow sucking my best friend’s cock was the most normal thing happening! My uncle pulled his finger out of me, leaving my hole with this hungry feeling. I wanted him to put it back. But then I felt his hands resting on my hips and the warm, smooth feeling of loins up against my ass. I couldn’t breathe. I’m pretty sure my heart stopped, too. I felt myself locked in place in the warm, well-fucked pumpkin as my uncle slowly slid his cock inside me. I couldn’t believe what was happening. But within moments, I felt his thick, hot shaft moving its way deeper into my body, steadily going until I felt his body flat against mine. I finally let out an exhale. Fuck, it felt so good. Every doubt I had seemed to go away and all I could think about was how hot he was and how much I wanted him to fuck me. As he began to thrust into me, I felt the pumpkin begin to rock back and forth from his movements. My cock continued to work the gourd, all while Tom’s cock rested in my mouth. And in a moment of clarity, all I could think was how much more I was going to need to see my uncle going forward... [Read more]

Tape 1 Family Photos MY BEAUTIFUL BOY

Richie is amazing. I could have never imagined when I became his step-dad that I would take to him so closely. We’re very different, and that’s ok...ay. I appreciate him so much for who he is and who he is becoming. I’ve always been a bit outgoing and fearless, but Richie is very shy and still a bit unsure of himself. I want him to see himself the way I see him. I came across a photographer who does incredible photography of fathers and sons. And even though he’s not my own, he’s still my boy and I want him to feel that. I scheduled the photographer and told Richie it would be a nice thing for us to have and look back on. But I didn’t tell him the whole truth… The photographer doesn’t just photograph dads and sons for holiday cards. He also does incredibly compelling, beautiful, even erotic photography. Nude men with their handsome sons, embracing and connecting in, well, unorthodox ways. But still beautiful and artistic. I know I’m a bit of an exhibitionist, but I wanted to find a way for Richie to feel more comfortable in his own skin. I’ve seen him naked a few times and, if I’m being honest, I know he’s got a little bit of a crush on me. He always has since we first met. And now that he’s all grown, I want him to see me not just as his dad, but as a man he can be close to. Even… really close… During the photoshoot, the photographer did a great job posing us and making us look great. It was a little silly at first, as all photoshoots are, but once we got into the groove, I could see Richie beginning to glow. He was confident and happy! And he seemed like he was having a good time. Seeing my boy happy just filled me with so much feeling. And before I knew it, I was popping wood in my pants! I couldn’t tell if it was obvious, but I decided to just let it lay. If I look aroused in the photos, fine! That’s just me reacting to my beautiful boy. Eventually, though, I wanted to get more of the photos I’d seen before. The naked ones. So I prompted the photographer and he instructed us to strip off our clothes. I could see Richie was a little uncomfortable at first. I wasn’t sure if it was more about being naked with his old man or if it was being naked in front of the camera. Either way, I assured him that not only would he love it and love the photos, but that he was absolutely stunning and had no reason to be embarrassed of his body. It took a little bit, but Richie became more and more comfortable. I think he was still relying on me to comfort him and assure him, but that’s what dads are for! And I couldn’t be prouder. ...Or more turned on. And what’s more, I could see his cock starting to stand up for me! Once the photo shoot ended, I could hardly contain my excitement. Something about seeing him step out of his comfort zone, trust me, and stand proudly side by side with me just made my heart swell. A passion rushed over me. As we made it back into the house, I found myself absolutely and totally enamored with Richie. We had to get dressed to come back inside, but I just wanted to see him naked again. I brought him into his room and couldn’t control myself. I brought him in close and gave him a kiss. I don’t think he expected it, but he didn’t back away. He was still flushed and worked up from our session, but I could see that I’d gotten him pretty excited. What separation we maintained from each other now seemed gone. Posing naked, being free, being open, I felt like I could finally show him how I felt about him. I kissed down his neck, holding him gently and slowly. I didn’t want to rush it. My hands moved over his body, under his clothes and across his smooth, milky skin. He was so flawless, it was unreal. And when I put my hands beneath his underwear and caressed his butt, I thought I’d died and gone to heaven. I couldn’t stop. Richie was so beautiful. My boy. My sweet boy. I had to have him. It was just inevitable. I kissed him again and bent him over the edge of the bed. He was a little timid, but he presented his hole to me so perfectly. I got down and paused. I took a breath, thinking that I was about to finally taste my boy. I got rock hard beneath my clothes, but didn’t want to lose the moment by undressing myself. Instead, I slowly extended my tongue, feeling the soft, pillow flesh of his cheeks against my face right before I made deep contact with his boyhole. I couldn’t believe it. How lucky was I? Many dads never get to experience the delight of tasting their boy’s hole, and here I was, connecting with Richie more than I had even hoped possible! I knew I was going to have to fuck him. He was going to have to take my bare cock and feel my seed inside him. But I wanted to take it slow. Make him know that he was loved. And being the good boy he is, I know he wanted it, too... [Read more]

Tape 2 Interview Prep TEACHING MY GRANDSON

Jack is lucky to have a grandpa as attentive and caring as Lance. The older man is not only handsome and charming, but he knows quite a lot. Jack want...s to soak up as much knowledge from him as possible. Even before he lost his virginity to him, Jack looked up to grandpa more than most other men in his life! And now that they have a new, special bond, he knows he can go to him with anything. When Jack started applying for jobs, he was nervous about how to present himself. He was a little shy and unsure of himself around older, more successful people. So to get some advice, he went to his grandpa’s office on how to best prepare for an interview. Given Lance’s success, he was sure that the older man would know just what to say. Whenever Jack visited his grandpa’s office, he was always impressed with the way people regarded him. His employees treated Jack like he was a prince because he was the grandson of the boss. And they had nothing but wonderful things to say about his grandfather. Jack was overcome with a sense that Lance was important and powerful and that his time was incredibly valuable… which made visiting him all the more special. Jack stepped into Lance’s office, seeing the handsome man behind his desk, dressed in a perfectly tailored suit and looking like a total boss. Jack couldn’t help but find him incredibly sexy, albeit intimidating in his place of business. But his face lit up brightly when he saw his grandson, similarly dressed in a dress shirt and tie. He was instantly proud of him and happy to see him, telling his secretary to block off his schedule for a while. Jack blushed, trying not to embarrass himself, but all Lance could do was look at him and gush. He walked him through some simple interview etiquette things such as proper eye contact, a confident handshake, and being intimately familiar with his resume should any questions arise. The businessman in Lance was strong and sure, but Jack felt like he was wearing a costume and pretending to be someone else. Lance could see Jack was a little unsure of himself. His insecurity was manifested both in his demeanor and the crooked way he tied his tie. Lance stood up and came in close to correct his accessory, standing mere inches away from the young man who bred him not long before. Jack’s pulse quickened as he felt his grandpa gently pull him in by his tie. It wasn’t intended to be sexual, but the proximity of the older man was enough to send a burst of energy to the boy’s loins. He remembered how good the older man felt against his body, even wrapped around his cock. It was impossible not to think of it being that close again. Lance could feel Jack getting aroused. Not only was his breathing changing, but a noticeable rise in his pants resulted from the correction of his tie. “What’s that about?” Lance asked playfully, looking into the boy’s eyes and seeing his hunger for more. Lance liked knowing Jack wanted him, but more than going in on his own, he wanted to tease it out of the young man. Jack said he was just nervous. Lance smiled. “Well, if this happens when you’re nervous, we’ll have to take care of it before your interview…” Lance dropped to his knees, pulling out the boy’s cock, feeling it surge with youthful desire in his grip. It was still fresh and exciting for him to handle his grandson’s member, knowing how easily it could have never happened. He didn’t take it for granted, but he couldn’t hide his ravenous hunger for it. Jack looked down as the handsome, powerful, successful older man devoured his cock. It felt so good, but it also gave him a boost of confidence. This man could have anything he wanted, and what he wanted more than anything else at that moment was him. It made him feel good. More than good. It made him feel secure. Lance stood up to give his boy a kiss. Jack’s lips pressed against his grandpa’s feeling the soft feeling of his well groomed silver beard. He smelled expensive and rich while also still possessing his familiar warmth. Jack began to unbutton Lance's shirt, taking off his jacket and pulling off his belt. As he stripped away the fine clothing, he revealed the beautiful, muscular frame of the older man, covered in silver hair, tanned skin, and bold tattoos that made him look superhuman. Jack was in awe of him. He was like a god. And he worshipped him. Falling to his knees as if in reverence, Jack took out the older man’s cock, taking it into his mouth with the same hunger that his grandpa showed him. He loved being able to taste and smell the tool of the patriarch. He knew this was special. Lance felt an immense sense of pride in his grandson. He loved him no matter what, but feeling his soft lips wrapped around his tool was a pleasure unlike anything else. He would do anything for him. But as Jack got him harder and harder, he knew the inevitable was coming. Right then and there, in his office, He was going to have to breed him... [Read more]

Tape 1 Top Training TEACHING MY GRANSON

From the outside, Jack’s household seems perfectly ordinary. Close-knit, loving family with a handsome, all-star athlete boy. And in many ways, this... is true. But what people might not assume is just how close-knit Jack is to the men in the family… particularly his grandpa, Lance. Grandpa Lance has always taken a special interest in Jack. The young man’s bright, sunny smile always puts the older man in the best mood. For Lance, so much of his joy came from how much he reminded him of his son, Jack’s father. Lance loved being there for his son when he was growing up. And back then, Lance was busy being a business owner and community leader. He didn’t have a lot of time for his son, something he deeply regretted. When Jack came into the picture, he swore to make sure Jack had all the attention he could ask for, giving him every bit of encouragement and advice possible. Of course, Jack was much more than just his son’s kid. As he got older and developed into a young man, Lance couldn’t help but notice how handsome he was. Even sexy. Something about his wide-eyed innocence matched with his familiar good looks made Jack hungry for him in a way he hadn’t imagined. Their first kiss came as a bit of a surprise. The two were embracing each other after a holiday when the two were uncharacteristically flirty and close. The rest of the family had started to go to bed, but Lance and Jack were up laughing and messing around, becoming unaware of the late-night hour. It was quick at first, then the second was somehow longer and deeper. Jack had never kissed a boy before--or a man, for that matter--so he was naturally confused by all the emotions he was feeling. It felt nice. Strange and unexpected. He didn’t know if it was because it was his grandpa or because it was his first. He couldn’t deny that he was attracted to the older man. How could he not? Grandpa Lance was the definition of silver fox, well built, successful, friendly, and warm as a wool blanket. He even smelled like firewood… something Jack had not noticed until that moment, but never forgot after. The two went to bed separately, not going any further. The rest of the family didn’t know what happened, but Jack waited for the chance to kiss him again. Months later, Jack found himself on the eve of a first date. He was excited and nervous, as young men are, sitting in his room and waiting for the day to carry on it’s slow march. He couldn’t get out of his head, thinking about all the ways he could mess up and embarrass himself. He was so distracted, he barely noticed Grandpa Lance enter his room. He was dressed impeccably, clearly coming from the office after work. It wasn’t uncommon for Grandpa Lance to show up to the house, but very rarely did Jack and he find themselves alone. Lance closed the door behind him, locking eyes with his grandson, and feeling his chest fill up pride. Lance said he heard about Jack’s date and wanted to give him a bit of pep talk. Jack’s face cracked the biggest smile, feeling his nervous subside with his grandpa there. Jack was expecting advice on how to open doors and be polite, but the handsome man caught him off guard by asking a direct question. “Have you ever had sex before?” Jack’s face flushed red. He didn’t know what to say that would sound right, so he just told the truth that he hadn’t. Lance smiled, feeling a mixture of relief as well as excitement. He liked being able to help his boy out with such a momentous occasion. And the idea that it was his first time only made it all the more special. Lance took off his jacket, revealing his bulging muscles tightly wrapped in his fine, collared shirt. Jack never got over how beefy the older man was, putting many younger men to shame. Seeing him begin to unbutton his sleeves and shirt, Jack found himself at a loss for words. “Do you want some pointers?” Grandpa Lance asked, already beginning to remove his clothes. Jack could hardly believe what he was hearing and seeing. It became pretty apparent that this was not going to be a usual birds and bees conversation, nor was it going to be purely theoretical. Grandpa Lance told Jack to start by taking off his clothes, which the boy eagerly jumped to the edge of the bed to help. His fingers quickly and excitedly finished the last of the buttons and the dress shirt fell off with ease. As Jack looked up, he saw the beautiful spread of soft white hair across Lance’s muscular chest, his well developed pecs pushing out freely and making him look even bigger than before. As Jack’s eyes went wide and his mouth fell open, he took in the scent of that firewood… and he was in heaven. With Lance’s permission, Jack took a handful of the older man’s member, still concealed in his underwear. It was big and warm, plenty thick and growing harder as he touched. Lance guided him to his nipples. Jack teased them before taking them into his mouth. His soft, full lips pressed onto them, feeling the silky fur of his chest caress his face. Lance repeated under his breath “good boy, that’s my boy” as Jack navigated his body, seeing Jack’s cock begin to tent up his shorts. Lance wanted to show Jack exactly what he needed to know. Taking off his underwear, Lance got up on the bed and spread his legs apart, giving Jack a look at his hairy, bare ass and tight hole. Jack gazed at the man’s backside, never having seen something so beautiful. Everything he’d seen in porn and in life was all smooth skin twinks. But here was a man like he’d never seen, in the flesh, and ready for him to explore. Lance taught him how to rim his ass, relaxing and tightening his sphincter on the tip of the young man’s tongue, giving plenty of encouragement and guidance on how to properly loosen him up. Jack couldn’t believe he was tasting his grandpa’s hole, but everything about how it looked, tasted, and felt was amazing. He could have stayed with his face planted between his fuzzy cheeks for hours, but his throbbing cock was becoming too much to bear, and Grandpa Lance was keen to feel it deep in his hole... [Read more]

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I've always loved jerking off to stories and videos of men having sex with their boys. I used to fantasize about getting fucked by my old man or sucking off one of my very handsome uncles. I thought those feelings would go away when I moved out on my own, but they only got stronger! I love to flirt with dilfs online and get them to send me videos of them fucking their boys. And since I’m beating off to this hot content anyway, why not share it? I get the best real gaycest videos, featuring boys whimpering as they get load after load pumped into their smooth little holes, and I post them here for you to enjoy!

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