TYLER:

    Looking for any excuse to visit Uncle Dixon's house, I woke up early in the morning and drove to a nearby bakery to get coffee and bagels for breakfast. Standing at my uncle's door, I knocked softly, hoping that he wouldn't hear it. When there was no response, I used the spare key to get into the house. 

    "Uncle Dixon? It's me, Tyler," I said. I left the food in the kitchen and crept up the stairs holding the two cups of coffee. The bedroom door was wide open, and I could hear my dad's brother snoring in bed. 

    When I walked into the room, the sight that welcomed me was precisely what I'd been hoping for. Uncle Dixon was stark naked, sleeping with his hard dick pointing up at the ceiling like a flagpole. I licked my lips, remembering what that dick tasted like in my mouth last night. I was tempted to wake my uncle up with a blowjob, but before I had the chance to act Uncle Dixon opened his eyes.

    "Oh, hi Tyler," he said, unperturbed by the fact that I had pretty much broken into his house.

    "I knocked but there was no answer," I said quickly. "I used my parents' spare key to get in. I brought coffee and bagels. I figured you probably don't have any food in the house yet so I—"

    "Shhhh, too much information this early in the morning," Dixon said groggily. "Lemme try that coffee."

    I handed him one of the cups and watched him reach out for it with his right hand while his left hand grabbed a hold of his boner and gave it a single stroke.

    "What's this?" my uncle grimaced after taking a sip.

    "A regular latte. This other one has pumpkin spice in it, if you prefer."

    "I'd rather drink my morning piss," he said. "But I appreciate the gesture."

    "The food is downstairs. I can bring it up if you wanna eat in bed."

    "I'm not hungry yet, but I'll probably have some of it later. That's nice of you."

    "I just wanted to say thank you for yesterday," I said, staring at my uncle's erection, which was now glistening with a fine coat of precum on the tip. "I had fun."

    "No need to thank me, man. I had fun too. If anything, I should be thanking you. I haven't had a good blowjob in a while."

    "I can… do it again," I offered hopefully.

    With a smirk on his face, Uncle Dixon spread his legs wider and placed the coffee cup on the nightstand. I put down my own cup and I crawled into his bed, kneeling between his hairy legs and running my hands from his knees up his thighs, all the way to his warm crotch.

    I stroked his ballsack for a bit, watching his face for a reaction. He nodded his head approvingly. I wrapped one of my hands around his dick, giving it a few slow strokes, causing more precum to ooze out of his piss slit. 

    My tongue left my mouth on its own, drawn to my uncle's cockhead like a magnet. Two seconds later, I was licking the prejizz off his dick and sliding my lips down his shaft. It's funny: this was only my second time giving a blowjob, but it already felt like it'd done it two hundred times. The nervousness I felt last night was now gone, for the most part. I knew I could do this. It felt familiar, yet different at the same time. Uncle Dixon's crotch smelled different – even muskier – first thing in the morning. His pubes tickled my nose as I got almost all the way down his shaft. 

    "Fuck, Tyler. You're a fast learner, kid," my uncle said, grabbing the back of my head and shoving that final inch down my throat. "There we go, buddy. Fuck, just like that. I'm warning ya, you gon make me cum soon."

    Even if I wanted to pull off, I couldn't, not with him holding on to my head. I did my best to relax my jaw, letting Uncle Dixon fuck my throat for merely a minute before he started flooding my mouth with his jizz.

    "Fuuuuck. Just what I needed. Fuuuuck, Tyler, you're so fucking good. Fuck, man," he kept grunting, thrusting his hips and fucking my face while pulling on my hair. All I could do was focus on my breathing and swallowing. Although the blowjob had been brief, my uncle's orgasm went on for a while, and he kept thrusting inside my throat even after he was done cumming.

    Finally, I was able to pull my head up after Dixon let go of my hair. I made eye contact with him and we both smiled, this time thanking each other without using any words.

    "Best way to start the day," my uncle said, standing up and stretching his entire body. Even from a few feet away, I could smell his hairy armpits.

    "We can do this every day," I suggested early. "Or… we can do more."

    My uncle raised his eyebrows.

    "Uncle Dixon… You've mentioned doing stuff with guys. Have you ever had sex with a guy? Like, anal sex, I mean?"

    "Yes," he nodded stoically.

    "I've been curious about stuff like that. About getting fucked, I mean," I continued. "I just thought… I would feel really comfortable with you doing it. If you want to."

    "Tyler, have you ever been fucked by anything? Like a toy or whatever?" Dixon sat next to me on the bed, his dick still not fully flaccid yet.

    "No," I admitted.

    "Then my dick isn't the best tool to start with. It ain't exactly beginner friendly," he chuckled. "But tell ya what: one of these boxes here has some sex toys that you can use to try to loosen up your hole."

    "I wouldn't know how to do that on my own," I said.

    "Come over tonight and I'll show you," Uncle Dixon winked. "Now if you excuse me, I gotta go take a shower. I'll meet you down in the kitchen for breakfast."

—

    I spent most of the day researching online about how to make "anal action" painless and seamless, followed by a long thorough shower, just like the guides recommended. I was buzzing with excitement, and as soon as my uncle texted me to say it was good to stop by, I sprinted next door.

    I found Uncle Dixon in his bedroom. All of his stuff seemed to be fully unpacked by now, except for one box that sat on the bed next to a laid out towel. He greeted me shirtless, wearing a pair of gym shorts. Even though the fabric was loose, my freeballing uncle sported a large bulge in his shorts.

    "You ready for this?" he asked casually, followed by an enthusiastic nod from me. "Take a look through that box and see what interests you. And don't worry: everything in it has been thoroughly washed."

    Uncle Dixon leaned against the wall and watched me with an amused expression as I started rifling through the box on the bed, which I could now see was full of sex toys. There was a set of butt plugs that increased in size, vibrators that he probably used on women, nipple clamps, some silicon cockrings, and a couple of dildos. One of the dildos looked pretty tame but the other was much bigger, almost as big as my uncle's dick.

    "Have you ever used these? On yourself, I mean?" I asked him, curious to know if any of the anal toys had been inside my uncle's hairy ass.

    "I've had other people use 'em on me," he revealed coolly. "But only the smallest ones. Honestly, my hole ain't exactly loose."

    "What should we start with?" I wondered out loud.

    "Grab the lube and one of those plugs," he suggested, walking over to the bed and putting his muscled arm around my shoulders. "Best to start small."

    I picked the smallest of three plugs, which I figured was a safe place to start. I handed it to my uncle along with a bottle of lube, before quickly shirking all of my clothes. Standing next to Dixon, I felt so small with my slim frame, but his larger, more imposing size made me feel safer in a way. I got on all fours on his bed, waiting anxiously.

    "You ready?" he asked me softly, followed by the sound of the lube bottle squirting into his palm.

    "Mhm. I fingered myself in the shower a little bit before this," I admitted.

    "Is that so?" my uncle chucked.

    He went quiet and that's when I felt one of his thick fingers tracing the outline of my hole. He pushed in with his forefinger. I moaned softly as I was penetrated by another man for the first time. I was glad I'd practiced a bit earlier, so I was able to take his finger without too much resistance. My dick instantly grew hard, just like it did in the shower earlier when I was fingering myself.

    "I'm impressed," Uncle Dixon said, resting his other hand on my smooth asscheek. "That slid right in. Let's try a second finger."

    My dad's brother then pushed his middle finger into me, making me moan even louder as my hole started to stretch to its current limit. The pain wasn't unbearable, but it wasn't exactly comfortable either.

    "Mmm. Nothin' like a fresh, tight, virgin hole," Uncle Dixon said under his breath, fingering my ass with two of his fingers, adding more lube every couple of minutes, until I could feel my hole loosening up. At that point, my uncle grunted, "You're definitely ready for more."

    His fingers retreated and were soon replaced by the smallest of the plugs. The toy wasn't as thick as my uncle's digits, which came as a temporary relief. Uncle Dixon used the plug to fuck me for a few minutes, moving it back and forth rapidly, and making me leak precum all over his sheets. His other hand rubbed my taint and my nuts, even reaching forward and giving my boner a few strokes. When he concluded that this was too easy for me, he asked me to hand him the medium-sized plug. 

    As the second toy went in, I groaned in frustration, feeling the pain of the stretch this time.

    "Deep breaths," Uncle Dixon soothed me, stroking my back while he kept steady pressure, pushing the toy in slowly. "Try to relax as much as possible."

    My hole kept wanting to clench but I did as he instructed. Little by little, the toy pushed into me until at last, he stopped. He let the plug sit there until my insides got used to it. Eventually, the discomfort went away, and my dick felt harder than ever.

    "You're doing so good, boy," Uncle Dixon assured me. "I'm not gonna use anything bigger just yet. How does that feel?"

    "It feels okay. I'm getting used to it," I said.

    "Does it feel good?"

    "Um, yeah, kinda, but… Honestly, your fingers felt much better," I confessed.

    "Well, if that's what you like…" Dixon said, pulling the toy out without finishing his sentence. Now that it was empty, my hole instinctively wanted to tighten, but before it had the chance to close, my uncle slipped two fingers inside me again.

    I wriggled my hips, loving the feeling. My uncle started pushing in and out, using his thick fingers to fuck my ass. I wasn't sure what he was doing, but at one point he got deep enough to hit a spot inside me that made me leak precum like crazy. Shit, that must be my prostate! For the first time ever, I could feel it! FUCK, it felt so good!!

    "Uncle Dixon," I gasped, barely able to speak. "Don't stop!"

    He didn't stop. If anything, he pushed even deeper inside me. I moved my body back and forth, fucking myself on my uncle's fingers. His other hand rubbed my lower back, which was sticky with sweat by now. Then, he reached between my legs and grabbed my boner again, stroking it up and down while continuously pressing on my prostate. 

    "Fuck. Fuck! Fuck!!! FUCK!!!" I shouted, unable to control myself as I began to experience BY FAR the strongest, most explosive orgasm of my life so far. My dick vibrated within my uncle's fist, spraying jizz all over the bed. My arms were shaking, barely able to support me. A split second after I was done cumming, I collapsed onto the mattress, reeling from the most intense sensation of my life. 

    Uncle Dixon withdrew his two fingers from my hole, slowly, then used the towel to wipe them clean. I could feel my hole gaping for a few seconds before it finally closed. "You might be ready to take a dick soon," my uncle's voice hinted.