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Staying with Uncle Stan


Stretching His Hole


    "Mmm," I moaned in my sleep, enjoying a satisfyingly sexy dream in which I was getting my dick sucked. Ahhh, what a wonderful sensation. The person doing the sucking really knew what they were doing, and how to do it exceedingly well. Fuck, if only this was real. Still in a state of half-sleep, I brought my hands to my groin, ready to jack my cock, which was throbbing in all of its morning glory. But then… I touched someone's face. I ran my fingers through someone's short hair. I began to hear the slurping sounds as their head bobbed up and down on my dick.  

    This wasn't a dream – I was getting a blowjob in real life! Somebody was waking me up by sucking my dick. I've had this happen a few times before, but only when I was sharing a bed with a partner or a fuck buddy. I went to bed all alone last night. Who the hell was deep-throating my dick first thing in the morning? 

    "Nash," I said as I opened my eyes to see my teenage nephew looking up at me while sucking the precum off the tip of my dick. Even with a mouthful of cock, I could tell Nash had a shit-eating smirk on his face. "I really need to start locking that door." 

    "But then you wouldn't get to wake up like this," the young cocksucker said before diving all the way down and burying his nose in my bushy pubes. Up and down, up and down, he worked me with his lips, his tongue, and both of his hands. Within a matter of minutes, I was feeding my brother's son my morning spunk.  

    "Fuck! You little bastard. Fuck, that feels good!" I groaned, pulling Nash's hair while shoving my tool as far as it would go, painting the back of his throat with my jizz. 

    "Mm. Yum," the teen smacked his lips before extracting my sensitive dick from his mouth. "Thanks for that, Uncle Stan. I hope you don't mind I went down on you while you were asleep. You  were already hard so I had a feeling you wouldn't have a problem with it. I came in here to ask you a question and when I saw your morning boner… well, I just couldn't resist." 

    "You little cocksucker. What'd you wanna ask me?" I said, laughing out loud as a way to let Nash know I didn't mind being woken up like this. I almost told him he could do it more often but I didn't want to encourage him too much. 

    "I wanted to ask if you'd be home tonight. I need you to do me a favor after school." 

    "What kinda favor?" I said. Now that my dick was going soft, I was becoming more aware of my need to take a piss. 

    "I'll tell you tonight. Will you be here?" Nash said with a secretive smile. 

    "Fine," I agreed. I figured I owed him one after that masterful blowjob he just gave me. 

    Later that evening, after I was done with work, I was washing up some dishes in my studio above the garage when I suddenly felt a blast of chilly air, setting my nipples erect. I looked at the door, which was open. A second later, Nash walked in, carrying a small backpack similar to the one he wore to school. He smiled and waved at me, letting himself in of his own accord.

    "Hey, Uncle Stan. Can I put on some porn?" the teen asked, removing his coat and boots, and barely waiting for my grunt of approval. He walked over to one of my bookshelves, selected a vintage vanilla gay flick on DVD, and popped it in the player. As the scene started, my nephew emptied his backpack, and I realized he hadn't brought school supplies after all.

    Somehow, Nash had amassed a small collection of anal toys in various sizes. He still had his job at the hardware store and I guess now that he was making money he was finally a paying customer at The Adult Arcade, instead of just being their resident cocksucker.

    "Woah, buddy, what's all this stuff?" I questioned, eyeing the assortment of toys. "Does your father know you're here?" 

    "Nah, he's at Kelly's. He told me not to wait up, he'll be out all evening," Nash assured me as he set a bottle of lube on the table, the bag now completely empty. 

    "And what's this all about?" I asked again.

    "I've been working on stretching my hole with some toys lately. There's someone I think I'm ready to go all the way with," Nash explained while starting to strip naked. "But it's... not going too well. Like, I can only take the smallest dildos and plugs. So, I was hoping... maybe you could help me with it?"

    My first reaction was to laugh out loud, assuming this was some teenage joke. But based on the look on Nash's face, I realized he was serious. When it came to sex, my nephew didn't get embarrassed easily, but now his face was glowing red. I felt bad – I didn't want Nash to think I was making fun of him.

    "Sorry, I didn't mean to laugh at you," I apologized, looking him in the eye. "Um, of course. Of course I'll help you if I can." 

    His face immediately switched back to looking gleeful. This was certainly unorthodox, but it's not like the rest of our uncle-nephew relationship was what most people would call "normal." I saw that Nash had brought some cheap lube, so I got out my own instead, as well as some poppers from one of my nightstands. I turned up the heat to the max so Nash would feel comfortable naked. Then, since I felt too hot, I decided to take off all my clothes as well. Lastly, I got a few towels from the bathroom, spreading one out over my bed. 

    "Here, come over to the bed so we have more room to work with," I offered, patting the towel. 

    Nash gathered up his collection of dildos with a smile on his face and joined me. He got on top of the towel on all fours, wiggling his teen butt in anticipation. I had to admit, his ass was perfect – hairless, rosy-pink hole, and completely virgin. For a moment, I had to remind myself this was my brother's son and not some random twink. But hey, I could still at least enjoy the view, right? 

    By now I was totally oblivious to the porn playing in the background. I grabbed a pillow, dropping it to the floor and kneeling onto it. My nephew's tight hole was basically at my eye level now. I picked up the smallest toy he'd brought, no bigger than a sharpie, and applied a liberal amount of lube on it. There was little resistance when I tried to insert it into Nash's asshole, but he eventually let me in. I began to move it back and forth slowly, and it only took a few pushes before he was taking it without any tightness.

    The second toy I selected resembled a cock this time. It was probably about as thick as my pointer finger and middle finger side-by-side. As I started to push this one in, Nash hissed in pain. I kneaded his asscheeks with my free hand, encouraging him to relax and breathe deeply. He heeded my advice. He needed a few moments to adjust to the size increase, but just like the first toy, he was eventually able to take it in stride. This one even made his teenage cock grow into a full-on boner.

    For the next hour, I trained my nephew's ass with progressively larger dildos and butt plugs. After a while of being on all fours, he switched to lying on his back, holding on to the back of his thighs to give me continued access to his gradually looser hole. Nash stayed hard the entire time, leaking out a healthy amount of precum that was now pooling on his slim stomach. As we got to bigger toys, the combination of fucking my nephew with rubber dicks and listening to his increasingly louder moans made my cock as hard as steel as well. 

    Eventually, we got to a toy that was only a few sizes smaller than my own dick, both in length and width; but it was still a nice, average-looking piece. Like all the others that came before, Nash experienced a moment of pain when I pushed the head in. This time, I waited a minute or two, giving his hole more time to adjust to the invasion.  

    "Nash, buddy, you're doing amazing," I soothed him, reaching for the bottle of poppers. "I want you to use this now, it'll help your body and hole relax. Just close one of your nostrils and inhale through the other one." 

    I offered him the small vial and he did as I instructed. I waited a few more seconds and then started to push the bigger dildo inside my nephew. The effects of the poppers were nearly instant, and his anal cavity parted, letting the toy slide in like a warm knife through butter. Nash took another whiff, and I was able to keep pushing until the toy was balls deep.

    Nash's cock was now harder than ever, practically squirting out precum like a water gun. I couldn't resist and I took my nephew's dick into my mouth, just like he'd done to me this morning. I swallowed him until my nose was buried in his small bush, savoring the flavor of his precum on my tongue. I started deepthroating him all while pulling out the dildo and shoving it back in his hole.

    "Oh, fuuuck! I've never felt so full before, Uncle Stan," Nash gasped as I continued fucking him with the dildo. "Unnnggghhh, you're gonna make me–" 

    Before Nash could finish his sentence, he began feeding me his delicious spunk. I made sure to swallow every tasty drop of teenage jizz, and I wouldn't let him out of my mouth until he had started going soft. Finally, I pulled the dildo out of his ass, setting it on one of the spare towels. I stood up and held his ankles apart, admiring his little gape. Nash put his arms behind his head and bit his lower lip.  

    In that moment, I wondered what it might feel like to fuck his virgin hole now that he was loose and ready. My cock twitched. I was sooo fucking tempted to just slip it in and show my nephew what a real man's cock felt like. I bent slightly at the knees, my hard cock hovering inches from his waiting and willing hole. Nash must've sensed my desire and lust. He opened his mouth to speak… when my phone started ringing. 

    I let go of his legs and saw my brother's name flash on the screen. Worried this might be an emergency, I answered the call. After a few moments of talking to Ray, I hung up and turned to his teenage son.

    "Your dad wants to talk to me. Says it's important, but wouldn't tell me what it is over the phone. I need to go meet him."

    "Okay," Nash said humbly. "Um, I'll pack up my toys and leave. And Uncle Stan…"

    With that, my nephew got up off the bed and planted a big kiss on my lips, tasting his own jizz in my mouth.

    "WHAT??!!" I shouted loudly at Ray. Thankfully, the music at the bar where he wanted to meet was loud so nobody stared at me, except for my brother.

    "Yes, she's pregnant," Ray repeated the shocking fact that had made me shout in the first place. "And I wanted to tell you first. But why do you seem so upset?"

    "How far along is she? Are you sure it's yours?" I asked, my heartbeat accelerating.

    "She's about to enter her second trimester. And yes, she hasn't had sex with anyone else for months, other than that threesome we had. And not like you could've knocked her up."

    "Why are you so sure?" I said, panic rising within me as I did some quick math in my head.

    "Dude," Ray laughed. "Are you serious? I don't know if you missed sex ed, but you can't get a woman pregnant by fucking her in the ass. Remember, that's what you did?"

    "Oh my God," I said. "Ray, I remember that night vividly. When I was about to cum, I pulled out and… I came on your dick, bro. I don't know if you even noticed. But you continued fucking her, with my load all over your cock."

    "So that means…" Ray said, the smile quickly wiped off his face.

    "If that's the night she ended up pregnant… either one of us could be the dad."

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