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Transcest
Mr. Lear and Luke Hudson
February 23, 2023 | Full Length Video : 23min 17sec
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Luke’s not had it easy. All his life my nephew’s had to deal with challenges that were never his fault. I’ve always been in his corner. As the youngest of my siblings, I had a better appreciation for what he was going through than some of the other members of the family. And when my sister, his mom, divorced, I made a point to stick up for the little guy.

As the years passed on, things got a lot better. Luke grew into a chill, handsome young man, even someone I found a friendship with. I can tell he likes spending time with me—he’d share his interests, his laughter, his concerns without any worry. Sometimes… I wondered if he had a little bit of a crush on me.

I didn’t mind. ...[Read more]

I didn’t mind. I kind of liked the attention; it made me feel like “the cool uncle.”

Lately he’d been spending a lot of time bouncing between houses. His birth dad, Joel, had been busy traveling and his mom had been spending more and more time working night shifts. Luke can absolutely take care of himself, but his parents would prefer if he stayed with someone who can look out for him when things got busy.

When Luke arrived, we had a relaxing night of playing video games, laughing, and eating pizza until we nearly passed out. He was only going to be here a couple days, so I might have gone a little overboard with the fun—and calories. I guess I was still trying to be the cool uncle.

I made up the guest room for him and we settled into the night. Back in my own bedroom, as I was scrolling through my phone before sleep, Luke knocked on the door.

“Hey,” Luke said, wearing just a white t-shirt and some underwear. “I can’t sleep. Can I sleep with you?”

When Luke was little he would, on occasion, sleep with me. He was like a little puppy who would nuzzle into my chest and purr through the night. It felt great to be able to give him that kind of support and affection.

He was much older now, so I wasn’t quite so sure. But then I remembered all the times my buddies complained about the mattress of the guest bed. It’d be dishonest if I didn’t mention how even they had to share my bed a few times.

So, I let him in. I thought nothing more of it as I turned off the lights and hugged my pillow.

I don’t know how much time passed, but when I was half awake, I felt Luke’s soft hands move over my body. It was a warm night, growing warmer as he traced fingertips through the hair on my stomach and chest. I could hardly think straight as he spooned me closer.

It felt better than I would have imagined, had I ever imagined it. It had been some time since I had this kind of closeness, and in my twilight state, I forgot all about the fact that Luke was actually family! So much so that I found myself guiding his hand lower and lower.

Before I knew it, I was rock-hard. Wakefulness grabbed me from my light sleep as my nephew groped my throbbing member. I didn’t want to stop, but I had to be the adult.

I turned around and whispered, “We can’t do this…”

It was almost more of a plea than a reprimand. Luke looked me in the eyes and I found myself struck. He was so handsome, but also very much like a puppy again. When he said he wouldn’t say anything to anyone, I found myself completely overwhelmed.

I turned the light on, half expecting it to douse my feelings. But all it did was make me more hungry to feel my nephew’s lips on mine.

I brought him in for a kiss. His hands worked up toward my cock. He snuck his fingers inside my boxers until he found the rigidity of my shaft. I couldn’t help but run my hand down low, feeling an entrancing heat in his pussy.

It didn’t take long for Luke to pull off my underwear and his, leaving him completely bare: skin to skin, uncle to nephew. He wasted no time in throwing his mouth on my cock, a sensation that almost had me blast right then and there. It felt so good, and frankly, he knew exactly what he was doing. I wanted to ask about how he became such a good cocksucker, but I know how I was at his age. I just wish I’d had a sexy, cool uncle to fool around with.

As Luke swallowed my dick, I spread his legs apart to feel his soft, wet pussy. I’d never been with a trans man before, and I hadn’t given much thought to Luke’s privates before now. His warm, welcoming hole and his hard t-dick between his masculine thighs drove a certain craziness into me. I’ve been with dudes before and I’ve been with women. But Luke… he was like a hot, skilled unicorn, one that made my balls ache to release.

I put him on his back and lapped at his pussy. Every time I looked up, Luke shot a satisfied, half-lidded glance at me. He moaned and spread himself open, desperate for me to stay inside him and work his body’s pleasure center. My beard brushed up against his soft fur, sparking hot friction between us. He tasted incredible, but what really sent me off was when he spread his legs apart, as if inviting me to enter him with my cock.

I paused. It was the first time since I’d turned on the light that I found myself reconsidering the situation. I knew it wasn’t exactly right to devour my nephew’s pussy, but something about the idea of fucking him seemed like a real departure from just fooling around. I knew nothing would ever be the same between us. He’d see me differently. I’d see him differently. He trusted me so much, I didn’t want to violate that in any way.

I asked him, breathlessly, “Are you sure?”

I looked him in the eyes, trying to determine his state of mind. We all get horny and do dumb things. I didn’t want to be one of them for him. But the way he nodded and said yes made it seem so effortless. It was like he’d thought about it before—this moment wasn’t planned, but I could tell he wanted it and had wanted it a long time. I guess I had been right; he did have a bit of a crush on me all these years.

As I moved myself up in bed, positioning myself between his legs and pointing my leaking, throbbing cock toward his pussy, I knew I was reaching the point of no return. I questioned if I was brave enough to go through with it, but then my love for Luke just completely took over. With a gentle push, I was inside him, enveloped in his tight warmth. He gripped me from inside as if he was holding me in place. Yet I still managed to thrust back and forth and feel an intense pleasure that I couldn’t contain.

Luke rubbed his t-dick, getting it harder and bigger as I worked myself closer to climax. I held off as long as I could, enamored with how he looked at the end of my cock and how his moans filled my bedroom. He made an unexpected motion; he reached for my underwear and gave it a sniff. I nearly lost it. He wanted me. He worshipped me. And he had me deep inside his body.

All it took was a few more pumps and I recklessly spilled my load into his pussy. My eyes rolled back into my head and I almost caught myself feeling regret. But Luke just cried out, “I want it! I want it!” That’s all I needed to hear…

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The Wheeler Family

The Wheeler Family: Chapters
1. Uncle Mason’s Bed 24mn
Luke’s not had it easy. All his life my nephew’s had to deal with challenges that were never his fault. I’ve always been in his corner. As the youngest of my siblings, I had a better appreciation for what he was going through than some of the other members of the family. And when my sister, his mom, divorced, I made a point to stick up for the little guy. As the years passed on, things got a lot better. Luke grew into a chill, handsome young man, even someone I found a friendship with. I can tell he likes spending time with me—he’d share his interests, his laughter, his concerns without any worry. Sometimes… I wondered if he had a little bit of a crush on me. I didn’t mind. I kind of liked the attention; it made me feel like “the cool uncle.” Lately he’d been spending a lot of time bouncing between houses. His birth dad, Joel, had been busy traveling and his mom had been spending more and more time working night shifts. Luke can absolutely take care of himself, but his parents would prefer if he stayed with someone who can look out for him when things got busy. When Luke arrived, we had a relaxing night of playing video games, laughing, and eating pizza until we nearly passed out. He was only going to be here a couple days, so I might have gone a little overboard with the fun—and calories. I guess I was still trying to be the cool uncle. I made up the guest room for him and we settled into the night. Back in my own bedroom, as I was scrolling through my phone before sleep, Luke knocked on the door. “Hey,” Luke said, wearing just a white t-shirt and some underwear. “I can’t sleep. Can I sleep with you?” When Luke was little he would, on occasion, sleep with me. He was like a little puppy who would nuzzle into my chest and purr through the night. It felt great to be able to give him that kind of support and affection. He was much older now, so I wasn’t quite so sure. But then I remembered all the times my buddies complained about the mattress of the guest bed. It’d be dishonest if I didn’t mention how even they had to share my bed a few times. So, I let him in. I thought nothing more of it as I turned off the lights and hugged my pillow. I don’t know how much time passed, but when I was half awake, I felt Luke’s soft hands move over my body. It was a warm night, growing warmer as he traced fingertips through the hair on my stomach and chest. I could hardly think straight as he spooned me closer. It felt better than I would have imagined, had I ever imagined it. It had been some time since I had this kind of closeness, and in my twilight state, I forgot all about the fact that Luke was actually family! So much so that I found myself guiding his hand lower and lower. Before I knew it, I was rock-hard. Wakefulness grabbed me from my light sleep as my nephew groped my throbbing member. I didn’t want to stop, but I had to be the adult. I turned around and whispered, “We can’t do this…” It was almost more of a plea than a reprimand. Luke looked me in the eyes and I found myself struck. He was so handsome, but also very much like a puppy again. When he said he wouldn’t say anything to anyone, I found myself completely overwhelmed. I turned the light on, half expecting it to douse my feelings. But all it did was make me more hungry to feel my nephew’s lips on mine. I brought him in for a kiss. His hands worked up toward my cock. He snuck his fingers inside my boxers until he found the rigidity of my shaft. I couldn’t help but run my hand down low, feeling an entrancing heat in his pussy. It didn’t take long for Luke to pull off my underwear and his, leaving him completely bare: skin to skin, uncle to nephew. He wasted no time in throwing his mouth on my cock, a sensation that almost had me blast right then and there. It felt so good, and frankly, he knew exactly what he was doing. I wanted to ask about how he became such a good cocksucker, but I know how I was at his age. I just wish I’d had a sexy, cool uncle to fool around with. As Luke swallowed my dick, I spread his legs apart to feel his soft, wet pussy. I’d never been with a trans man before, and I hadn’t given much thought to Luke’s privates before now. His warm, welcoming hole and his hard t-dick between his masculine thighs drove a certain craziness into me. I’ve been with dudes before and I’ve been with women. But Luke… he was like a hot, skilled unicorn, one that made my balls ache to release. I put him on his back and lapped at his pussy. Every time I looked up, Luke shot a satisfied, half-lidded glance at me. He moaned and spread himself open, desperate for me to stay inside him and work his body’s pleasure center. My beard brushed up against his soft fur, sparking hot friction between us. He tasted incredible, but what really sent me off was when he spread his legs apart, as if inviting me to enter him with my cock. I paused. It was the first time since I’d turned on the light that I found myself reconsidering the situation. I knew it wasn’t exactly right to devour my nephew’s pussy, but something about the idea of fucking him seemed like a real departure from just fooling around. I knew nothing would ever be the same between us. He’d see me differently. I’d see him differently. He trusted me so much, I didn’t want to violate that in any way. I asked him, breathlessly, “Are you sure?” I looked him in the eyes, trying to determine his state of mind. We all get horny and do dumb things. I didn’t want to be one of them for him. But the way he nodded and said yes made it seem so effortless. It was like he’d thought about it before—this moment wasn’t planned, but I could tell he wanted it and had wanted it a long time. I guess I had been right; he did have a bit of a crush on me all these years. As I moved myself up in bed, positioning myself between his legs and pointing my leaking, throbbing cock toward his pussy, I knew I was reaching the point of no return. I questioned if I was brave enough to go through with it, but then my love for Luke just completely took over. With a gentle push, I was inside him, enveloped in his tight warmth. He gripped me from inside as if he was holding me in place. Yet I still managed to thrust back and forth and feel an intense pleasure that I couldn’t contain. Luke rubbed his t-dick, getting it harder and bigger as I worked myself closer to climax. I held off as long as I could, enamored with how he looked at the end of my cock and how his moans filled my bedroom. He made an unexpected motion; he reached for my underwear and gave it a sniff. I nearly lost it. He wanted me. He worshipped me. And he had me deep inside his body. All it took was a few more pumps and I recklessly spilled my load into his pussy. My eyes rolled back into my head and I almost caught myself feeling regret. But Luke just cried out, “I want it! I want it!” That’s all I needed to hear…
2. Bringing In Dad 20mn
It’s hard to feel bad about what I did with Luke. I know I should, but seeing his face after we fucked was a thing of beauty. He was beaming. Unashamed. Almost pleading for more. If I had it in me, I would have given it to him. Still, I made it clear to him that he couldn’t tell anyone about what happened. Not because I felt guilty, but because they wouldn’t understand. I know that from personal experience. Luke’s stepdad, my brother Jonah, and I have a very close relationship. We always have. He’s barely two years older than I am, so I hardly remember a time when he wasn’t there with me. Granted, when I was very little, the differences between us were stark. But by the time we hit puberty, it felt like we went through everything together. We shared a room up until high school, so it was inevitable that we were going to see each other naked… even see each other jerk off. The first few times we pretended like we didn’t know what the other was doing. But in short order, we were fooling around in the privacy of our room. Eventually we had our own beds, but that didn’t stop us from sneaking into each other’s rooms whenever one of us was too horny to just jack it and crash. Obviously, a lot’s changed since then. Jonah’s gotten married, Luke came into his life, and I’ve been carrying on with a few relationships here and there. Still, whenever we are alone and have the urge, it’s like we’re kids again. When Jonah came by to collect Luke, we had a rare moment when it was just the two of us. Luke was still asleep upstairs, likely hours from coming down. After Jonah and I ran out of small talk, we found each other looking deep into the other’s eyes. It was magnetic. Without speaking, we both found ourselves drawn to each other, wanting desperately to be closer. It started first when Jonah put his hand on my leg. This was how it always started; an innocent enough gesture that no one would think twice about if they came in the room. It was his first move and a subtle indication of what he wanted. As I would normally do, I moved a little closer to him on the couch. Not so much that it would cause a stir, but just enough to show my interest in return. Neither one of us ever actually said “Let’s fuck,” but this brotherly ritual was one we knew well. I leaned in a little more and gave him a kiss. His mustache against my beard was a new development since the last time we had played, but neither of us seemed to mind. I took off my shirt and let him feel up my hairy chest. He closed his eyes as he ran his hand in my shorts, feeling the warmth of my crotch before he touched my cock. I wondered, for a man like him, married with children, how long had it been since he’d been with a man. Not just me, but any man. His breathy, focused demeanor seemed desperate for a taste. It was only the night before when Luke was desperate for the same thing. As Jonah took off his shorts and fell to his knees, I did my best to keep my ears attuned to any sounds in the house. Luke was upstairs, but it was only a matter of time before he woke up. I knew I could throw on my clothes if I had to… but I wondered… do I have to? Jonah worshiped my cock, sucking it down to the balls and inhaling my scent… unaware that some of Luke might have still been on the hairs of my pubes. The thought made me even harder, thinking about my hot nephew and his stepdad. I wondered what they would say if they knew about the other? Jonah could be tricky, given that he’s now a dad. But between my legs, fellating me, he was just simply my brother, the brother I had always known. I must have lost track of the time or simply couldn’t hear the creaky floor boards over Jonah’s hungry savoring of my meat. I looked up from the dark head of hair between my legs and saw Luke, standing there, watching. We made eye contact. My eyebrows shot up, feeling caught. I didn’t know what to do. It was like my perverted imagination made this happen. I wanted to shoot up in shock, but I was weak from Jonah’s expert cock sucking. I stayed silent, studying Luke’s face, looking for a sign from him. To my pleasant surprise, Luke just watched. He seemed fascinated by seeing his stepdad on his knees, sucking down my dick. He probably never thought about what his stepdad’s sex life was like, let alone that it might involve guys… including myself. Luke’s beautiful face didn’t turn away. He seemed fixated. I couldn’t help but stay rock-hard, enjoying the soft, wet motions of my brother’s lips on my shaft. I didn’t want to upset Jonah, but I had to tell him. “Looks like we’re not alone.” Jonah shot up off my cock and turned his head around. His mouth dropped open, drooling still from being full of my meat. He didn’t know what would happen, but luckily, Luke tried to put him at ease. “It’s okay, Dad…” Luke bravely stepped forward and moved himself between my legs. Jonah, still in some shock, moved to the side and watched in awe as Luke began to kiss up my thighs and pick up where Jonah had left off. Jonah couldn’t believe it, but he was still hungry for me. I could see it in his eyes. I gave him a nod and he made his way back in. Both Jonah and Luke seemed to take turns slobbering over my tool, occasionally pressing their lips together as they each tried to keep me hard and pleased. I was in heaven. I couldn’t believe what was happening. Before I knew it, we were all stripped naked, taking turns sucking cock: first mine, then Jonah’s. Jonah let out a deep, guttural moan as Luke expertly swallowed him. A look of pride shot over his face. He seemed surprised that Luke was capable of taking dick down like that. Jonah leaned back on the couch and I put my arm around him. It was like we were kids again, having fun on the couch with our parents gone. But this time, we had a sexy boy bobbing up and down on our cocks, his first, then mine, making our eyes roll back into our heads and edging closer to climax. I knew I had to have Luke again. Really have him. I couldn’t cum in his mouth; I needed to breed his boy pussy. I wondered how Jonah would feel about that? Before I could say anything, Jonah began encouraging Luke to suck my dick deeper! I guess he knows what I like. Luke stood up and got on the couch. He splayed his legs apart, inviting me to taste him. I lapped at his sex, ready to get inside. I kept going, waiting for Jonah to stop me. But instead, he just put his arm around Luke and watched as my cock slid inside his wet, warm hole. Luke moaned and Jonah’s eyes came alive. Seeing me fuck his boy was clearly activating some deep desire within himself. I hoped he would take a turn and try his boy out, but for now, he seemed perfectly content with watching me go to town. Maybe it was still a little new and strange for him, given that Luke was like his son. But he relished seeing me move in and out of him with ease. Then the moment came. Jonah couldn’t resist the urge. Seeing me enjoy his boy was too much to stay passive. We’d always enjoyed sharing our toys and fun in the past, and this moment seemed to be similar. I pulled out of Luke, my cock covered in his slick, and Jonah moved up behind and took my place. I leaned in and gave Luke a kiss, still feeling my cock pulse from the pleasure he gave. And as we were in our embrace, Jonah broke through into Luke’s hole, fully experiencing the handsome young man he was helping to raise. Jonah’s hips moved like ocean waves; Steady, smooth motions that were hypnotic to watch. He trembled as he tried to restrain his desire to fuck harder, as if trying not to hurt Luke. But I knew what he could take. And I knew what he wanted. Luke liked it deep. He liked it hard. And he wanted a warm, hot daddy load inside him. I knew if Jonah didn’t fill him up, I would happily step up…
3. No Substitute 26mn
My step dad and I didn’t say much on the ride home. Once we left Uncle Mason’s place, I was surprised how quickly we fell back into our usual routine. Jonah had always been very friendly and familiar, treating me like his son from day one. So it was not unusual for our conversation to lead to things like school, work, and upcoming obligations. We’d just never talked that like with his brother’s cum still inside me. I knew we weren’t going to have much chance to talk about it once we got home, but I never really managed to bring it up. I didn’t want to make things weird or make him feel uncomfortable. And I didn’t want him to feel like we couldn’t still be father and son. I just… I couldn’t help but remember how his cock tasted and how he felt just before he came on my stomach. And I wanted more. Much more… It took about a week before we were in the house alone. Mom had gone to visit some friends for the day leaving my step dad and I alone. I was doing some laundry when I saw his bedroom door was partially closed. I peaked in to see he was home and I saw him lying in bed, jerking off of. He was in nothing but his white briefs, stroking his cock and running his fingers through his thick, dark bush. Instinctively, I stepped away, wanting to give him privacy. All the while, I kept thinking about what we did. I know why we haven’t done anything or even said anything since, what with mom being around. But now… with him all alone and stroking himself… I wondered… does he want me? Can we do this? And if so, would he ask for it? The more I thought about it, the more I realized the answer. Jonah’s biggest fault is also his most redeeming quality… he’s a nice guy. He doesn’t want to ever push or coerce. He never even really came down on me for blowing off curfew or missing homework. He just wanted to get along and be a good dad. From my room, I called out, “Dad, are you here?” I waited to see how he’d respond. I expected him to sound flustered, quickly zip up his pants, and tell me to give him a minute. Instead, he responded, “I’m in here.” There was playfulness to his tone that made my heart start beating. I knew what he was doing; he was inviting me in. Mission accomplished. I slowly pushed open the door and saw his giant, thick cock standing upright while he sat back in bed. He gave me a look that was very different than I was used to. A look I hadn’t seen in a week. Not since the two of us were naked with Uncle Mason. He kept stroking himself, slowly, never taking his gaze off of me. He asked what was on my mind, and I told him the truth. I told him that I couldn’t stop thinking about what we did. He smiled, still stroking his dick, and replied, “Me, too.” I took off my shirt and got into bed with him. It was the first time I’d ever been like this with him. Even when I was at Uncle Mason’s, it was not exactly planned. And then, we were somewhere else… not our home. But this was our home. His bed. My step dad and I. And we were all alone. He leaned in and gave me a careful kiss. I could tell he wanted to go slow, following my lead. The nice guy in him. He didn’t want to push. But I wasn’t a little boy. And I knew what I wanted. I put my hand on his cock, feeling it pulse and throb in my grip. Little strings of precum landed on my knuckles and smoothed my strokes even more. Jonah seemed to like it. He responded by putting his hand in my crotch, beneath my underwear and feeling my t-dick. I was as hard as him, but he clearly had the inches. We laid in bed, playing with each other, being sweet and gentle, until he let me lean over and swallow his cock. God, I loved that taste. I didn’t get much of it before, but now, it was all mine to focus on. I took him down my throat and let his balls touch my lips. I watched them bounce with delight at the sensation. I knew from watching that he enjoyed a good cock throating, and I wanted to make him proud. As I sheathed him with my mouth, he played with my hole, feeling me become more and more ready for him to slide in. Jonah put me on all fours so I could keep sucking him while he mouthed my genitals. His tongue, lips, and mustache played a wild game, teasing and tickling me as he spread me open and moved further and further inside. I could have cum just from that, but I focused all my energy on his manhood. A part of me wanted him to cum in my mouth, to taste his load and feel him filling my face. But before I knew it, he was up and behind me, cock pointed right at my entrance. I gripped the edge of the bed, feeling the familiar bedding and looking out at the familiar space. It was always my parents’ room, a private space that was not for me. Now, as Jonah slowly pushed his cock into me, this was our space. Forever, I’d look at this room and think about Jonah fucking me. And that made it all the hotter. To my surprise, mild-mannered Jonah pinned me down and began to pound me hard. Harder and deeper than I imagined. All while also holding me close. I could tell that he loved how I felt, and loved knowing that I was all for him. I saw a side of him that I hadn’t even seen when he fucked me with Mason. This was his true, uncensored sexual self. And it was powerful and primal. Who knew he had it in him? I began to play with myself as he pounded on. He put me on my back so he could watch. As the head of his cock moved in and out of my hole, I played with my t-dick, gripping him tightly. I wanted to milk him. I wanted to make him cum. And as his breathing intensified, I knew it was coming. “You’re my boy,” he said as his hips quaked and I felt the flood of fluid fill my sex. It was a warm, intense feeling that seemed to never stop. My only regret was that I couldn’t see how much he’d cum, otherwise it was the hottest sex I’d ever had! He collapsed over me, trying to catch his breath, and I couldn’t help but think about the next time. Now I know, if I want him to fuck me, I just need to ask…
4. Beautiful Boy 24mn
It had only been going on for a couple weeks, but my step-son Luke and I had become closer than ever. Closer than your average step-dad and son is typically allowed. I was still a bit incredulous at the fact that my brother, Mason, had opened Luke up before me.I love my brother, and I know that he knows that, since we’ve fooled around, too. Despite my ping of jealousy, I’ll be eternally grateful to him for being the doorway to finally letting Luke and I bond, emotionally and physically. One lazy day I happened to walk by Luke’s bedroom as he was checking himself out. He was wearing a plain white tee shirt and jeans, which is basically the unofficial “hot dude” uniform. While I already knew just how cute his lithe, masculine body was, watching him admire himself… seeing that confidence in his face, it was both a joy and an instant turn on. Even when I let my presence be known to him, Luke kept checking himself out in the mirror. He lifted up his shirt and exposed his chiseled body. I walked in and stood behind him, throwing my arms around him in an embrace. I removed his shirt, and as his sculpted abs and chest were on full display, he flexed for me. I let my hands roam over him briefly before I leaned my face into his and planted a kiss on his lips. He slipped me his tongue, and I returned mine in exchange. Our mouths wrestled for flavor. I removed his jeans, exposing his beautiful, thick legs. Left only in his patterned gray boxer briefs, he slipped out of them quickly and got on the bed. I removed my own shirt and joined him, giving him another kiss before heading down to his boy hole and planting a kiss there too. He let out a moan—the kind of pleasured moan that made me weak—the instant my mouth made contact with his t-dick. I let my tongue work all over, around, and inside him. His moans increased in both volume and quantity, in time with sheet-clutching contortions. He was assertive in letting me know what felt good—I was so proud at how well my boy knew his body. I slipped a finger inside him. He was all wet. Luke unbuttoned my jeans and freed my hard, aching cock from the confines of my underwear. I worked my digits in and out of his front hole. He grabbed my meat and tugged on it; there was no ambiguity in his wants. I went back down to taste his t-dick, and his bonus hole. His moans reached a loud, demanding crescendo. He wanted me, needed me back inside him. Even though teasing him was fun, I was just as eager to get back in there. He moved around me and took off my pants. He brought his beautiful face to my rigid meat and wrapped his sexy mouth around my cock, swallowing it whole. I brought my hand to his wet opening and worked inside him. Fingering him like this made his gagging, sucking motions all the more eager. He pulled his mouth off my cock with a loud slurp. He rose, kissed me one more time, then finally straddled me. My cock slid into his well opened wetness. Somehow, his bonus hole felt better and better with each time I was inside him; it was a gift I never tired of. As I looked up at his face, he even seemed to be getting more handsome. I knew nothing had actually changed, but figuratively, his confidence and excitement molded his sweaty face beautifully. I could have shot right there just from looking at him. After he rode me for a bit, I had Luke get on his back. I could feel my balls tighten up as I alternated my gaze from watching my cock slide in and out of him to the sheer ecstasy on his panting face. Before I knew it, I had reached the hilt. I tried to keep going but it was all too much: his beauty, his warmth, the taboo intimacy of being inside my trans step-son. We locked eyes. I felt my seed rush out of my cock, filling him up. It was as if my whole spirit released into him. I collapsed onto him, giving him one final kiss as the piston of my hips slowed. I don’t know what I had done to deserve such a good, fortunate son, but I was thankful. Sweaty, weak in between the grasp of his legs, but thankful.
5. Attentive Uncle 24mn
I woke up the other day from a long, restful nap and decided to see what my nephew Luke was up to. I headed to his room—he's been living with me for several weeks now—and as I got closer to his bedroom door, I noticed two things: the door was wide open, and from inside there was the unmistakable sound of moaning. When Luke unexpectedly arrived at my door a few weeks ago asking if he could stay with me for a few days, I suggested that he could stay for as long as he liked. So from that point on, we’ve spent nearly every day together, really getting to know one another better. I tip-toed down the hallway. When I got to Luke’s open door, I peeked in to check on him. I just wanted to see if he was fine; let me tell you, he was more than fine! Luke was lying on the bed with his eyes closed, tongue damn near hanging out, legs open and pumping a very large and thick flesh-colored dildo into his boyhole. This smoking-hot nephew of mine arched his back and moaned again, much louder than before. He was probably close to cumming. I hoped—prayed, actually—that he was thinking of me. Suddenly, Luke opened his eyes and right away he saw me standing there, watching. He smiled, but with a shy countenance, and bashfully tried to cover his private parts. He explained that he didn’t realize that anyone was home and so took the opportunity to blow off some steam. And…would I care to join him? Fuck yeah, I would. I immediately laid down next to him and slipped my fingers into my nephew’s tight, deliciously moist boy-pussy. He arched his back yet again and moaned, with much more volume than the dildo had gotten out of him. Knowing I could out-perform that thing made me feel pretty good… and I was only just getting started. Soon, my salivating tongue found its way deep into his luscious and delectable bonus hole. After a wonderfully lengthy make-out session with his sweet, tender extra entrance, I let the starry-eyed twink know that I needed to fuck him far, far more than his toy did. No sooner had the words been spoken than those whipped-cream-soft jock thighs spread open for me. As I pressed my hips towards him, I unzipped my fly and slipped out of my slacks so that nothing remained between me and his hole. Nothing could come between us, except us. Luke pulled me on top of him and I slid myself, painfully swollen with lust, all the way inside his hole. Not one to brag, really, but honestly my cock kinda makes Luke’s dildo’s look small. And, boy-oh-boy, does Luke love giant cock! As I pounded my nephew into the mattress like a forty-horsepower piledriver, it’s like he started speaking in tongues. He gripped the sheets and begged for me to never stop. We worked up quite a sweat, and I eventually suggested that Luke and I change positions, that he hurry up and ride my dick. One of the things that I’ve really come to love about our new, budding relationship is that I never have to tell my nephew something twice. He really respects his elders. As Luke deliriously bounced himself up and down on my meat, I drilled up into the boy with swift, upward strokes. He would match my rhythm and slam himself down on my cock. His eyes rolled back when he hilted himself onto me. All the while, the turned-on twink fingered and played with his t-dick with wild abandon. I lost track of how many times that my nephew came while riding my cock. My crotch and pubic hair were soaked at this point, drenched in Luke’s sweet juices. I could feel my own orgasm quickly building, hurtling to the finish like a runaway train. I pulled the boy off me and laid him, again, onto his back. I pushed his twinky legs up and plunged immediately back inside of him. He cried out loudly and clenched the bedsheets as I thrust into him several more times, and then erupted. I looked down at my cock as I pumped what seemed like an impossibly massive amount of cum into Luke. My nephew gasped and stared at me with wide-eyed wonder. He couldn’t believe how much semen was blasting out of me, and how quickly it filled him to the brim. When I slowly pulled my cock out of my nephew’s boypussy, thick rivulets of cream came pouring out. Luke laughed playfully as we very slowly came down from our shared mind-bending climax. For as long as he chose to stay, I decided that I’d check into Luke’s bedroom more frequently…
6. TV Teaser 26mn
As Mr. Wheeler and his stepson Luke snuggled together on the couch watching television, there were two things that Luke had on his mind. First, he couldn’t help but contemplate the surprising speed at which he and his stepfather’s newly-budding sexual relationship had been going. The FTM twink had found that, although the carnal pleasures shared between them were a little weird at first, things had quickly become comfortable and easy. Yes, there was always that nagging voice second-guessing him, but it was losing–getting quieter over time. Second, Luke couldn’t help but be quietly fascinated—and pleased—by his always-randy stepfather’s fingers playing and massaging over Luke’s thin underwear. Mr. Wheeler made Luke’s sensitive genitals tingle and pulsate with pleasures the likes of which felt far more right than the more logical side of his brain was sometimes willing to admit. But, that wasn't all they were doing. They weren't just fooling around or exploring each other's bodies anymore. No, this was something more significant. It was an important moment, a milestone; Mr. Wheeler had said so himself. They were starting to find a rhythm together in each other’s lives. The television glowed, and Mr. Wheeler’s hands roamed. They clearly had no interest in watching the latest sci-fi TV teaser when beside each other. Mr. Wheeler also has that nagging voice—how could he not, given his own history with his father, Dale? The sensuous Daddy smiled contentedly as he nuzzled up against Luke’s baby-smooth yet masculine body. Mr. Wheeler, for his part, was still riding up on top of the peaks of this wave of craving he just couldn’t seem to quench for his stepson. Luke’s transformation–becoming the awesome man and person he was growing into–filled his heart with so much joy. Helping Luke find comfort in his transition and power in his new life made Mr. Wheeler very happy. When Luke would glance over and smile, Mr. Wheeler’s dick would twitch in whatever he was wearing, and instantly get hard. This stepdaddy now found it nearly impossible to keep his hands and fingers away from that smoking hot, seemingly always wet boy slit. Soon, the TV was completely forgotten. Now all that Luke wanted to watch was the manner in which Mr. Wheeler made out with his bonus hole. Luke’s juicy boyhole was practically smothered by Mr. Wheeler’s twirling tongue while also lustily inhaling the boy’s aroma. Luke arched his back… and climaxed. Mr. Wheeler finally came up for air some time later, licking his chops as Luke grinned with drooling happiness. The proud stepdad marveled at how perfect and beautiful this boy was to him, beaming with the confidence Luke has both in his body and in knowing himself. If Mr. Wheeler was being honest, he thought Luke will be even more handsome once he fully developed. The TV was just another object in the room, background noise. Life was good, and the sound and sensations of it was far greater than anything a screen could show them. So when Luke practically begged his stepfather to put his hard cock inside of his boyhole, the only dilemma that Mr. Wheeler had now was this: should they just get rid of the TV? Who needs cable when they could entertain themselves inventing countless ways to make each other cum?
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