CALLUM:

    Reuniting with Ben at my grandfather's Fourth of July party was quite unexpected for me. He was the first man I had sex with (excluding the unsuccessful attempt at anal with Dad's neighbour Paul) and as such he carried a special place in my heart. I knew that Ben and I had no future so I never got my hopes up, but I wasn't immune to his gorgeous looks and drawing charisma either.

    At Grandpa's holiday pool party, Ben and I had a few drinks, sticking together since we knew the fewest people at the party anyway. Ben shared that he's thinking of having another kid and I talked about my plans for university, until the liquor started to hit and the conversation turned a lot sexier and flirtier. One thing led to another… and Ben and I ended up in my room, fucking two times in a row.

    In a weird way, a part of me felt like I was "cheating" on my dad, but I disallowed myself to think that way. After all, Dad and I weren't a couple… obviously, he was MY DAD! The alcohol helped lower my inhibitions in the moment with Ben. But then as I sobered up, the gnawing guilt set in. Dad and I weren't "a couple," but we were definitely something. Something more than just your average father-son duo. But what did that even mean? Did I need Dad's permission to have sex with other men? 

    The following day, Ben invited me out for lunch. There, he revealed that he knew about the sexual aspects of my relationship with my father; Dad had shared the story with him. Although I initially felt panic, I realized I was actually exhilarated to have someone to talk to about this.

    "All I know is your dad loves you a lot," Ben said to me in his own paternal way. "He's confused. Take it easy on him. And just as importantly: take it easy on yourself. Whatever you guys decide to do, just give it time and be honest with each other."

    On one hand, Ben's advice was comforting. On the other, it didn't offer anything as far as actual solutions go. I decided to take the guidance to "be honest" to heart. After lunch with Ben, we said our goodbyes and I texted Dad, asking if he wanted to go to the beach together.

    At the beach, Dad and I took our shirts off and picked a spot where we could talk undisturbed by other beachgoers. There, I told Dad that I got fucked by Ben the previous day.

    "I know," Dad nodded calmly. "I heard you from the other side of the door."

    "Oh. I see," I said, feeling confused. "And… was that okay for me to do? Like, does it upset you?"

    My father looked out at the ocean and pondered for a few moments before answering.

    "It doesn't leave me unfazed or indifferent," he admitted. "But I also have no objections to it. Callum," Dad put his hand on my back, "you've just started having sex and exploring, and I think you should do it with multiple people if that's what you wanna do. I certainly did at your age. Besides, I love you, but I am not your boyfriend," he added earnestly. As much as I knew he was right, it still felt like a stab through the heart to hear those words so bluntly. "And you aren't mine. We can never be 'boyfriends' or anything of the sort."

    Looking out into the ocean, I knew my father was right.

    "But can we still have fun?" I asked hopefully. 

    "We can still have fun," Dad smiled, rubbing my back reassuringly.

—

    About a week later, I was up for a new surprise at my grandpa's house. While passing Grandpa's office I heard grunts and moans coming from it that could only mean one thing: somebody was having sex in there. Either that, or some porn was left playing on the computer really loudly. Was this a prank my uncle Blake was playing on me, to see how I'd react? The more I thought about it, that's probably what it was. Grandpa's wife was away for a few days, and if he was gonna have sex with another woman at the house, they wouldn't be so loud, right? Or maybe it was Dad fucking somebody in his father's office for some kinky reason? Either way, I took the bait and decided to check it out.

    I opened the door slowly and carefully, and what I saw in Grandpa's office felt like being hit by thunder. The grunts were indeed coming from my grandfather, who was clearly in the midst of blowing his load down my father's throat. Dad was on his knees, sucking Grandpa's cock like there was no tomorrow. Since Dad was busy drinking his own parent's cum with his eyes closed, he didn't even notice me but my grandfather sure did. Grandpa and I made eye contact just as he continued to bust the rest of his load down my father's cum-guzzling throat, giving me an instantaneous boner. 

    If this were some sort of fictional sex story, this would probably be the part where I step into the office and the three of us start fucking one another, taking each other's loads. But in real life, even though I felt horny and turned on, I also felt panicked, and shocked, and confused. I took a few seconds to stare at the scene and really take it in, before closing the door and dashing off to my room, closing the door behind me for privacy.

    There was a lot I needed to process. Number one, I didn't even know my grandfather was open to having fun with guys. He always seemed like such an old-school kinda straight man who just cared about making money and chasing women in a way that was unabashedly problematic. So to see him getting his dick sucked by another man – any man, let alone his own son! – was probably the most shocking in a series of unexpected discoveries. Nonetheless, the shock didn't take away from my horniness! As I lay in my bed with my eyes closed, I replayed the blowjob scene over and over and over in my head. My father down on his knees, sucking his own dad's cock. Grandpa blowing his cum-load in Dad's mouth while looking me dead in the eyes. My hand unbuttoned my shorts and pulled out my cock, which had never felt harder. Here, five thousand miles away from London, I felt like I was on some sort of sex planet where all of the male members of my family engaged in mutual fun. With my hand pumping up and down on my erect cock, I started to imagine what it must feel like for Dad to have Grandpa's dick in his mouth. That's something Dad and I had in common now: we'd both tasted our fathers' cocks!

    With my loose foreskin sliding up and down my sensitive bell-end, I started to leak copious amounts of cum. I used my fingertips to play with it, finally bringing it up to my lips for a taste, imagining it being Dad's or Grandpa's seed instead. Just two or three minutes later, overexcited by the thought of my family members, I blew my load all over my stomach, making sure to pull up my T-shirt so as not to make a mess. When I was done cumming, I brought the jizz to my lips and swallowed it, just like Dad had swallowed Grandpa's cum a few minutes ago.

—

    Even though I wanted to be honest with Dad, I decided not to tell him about the fact that I caught him and Grandpa at the office. The way I saw it, this was Dad's story to tell, and it was up to him if he wanted to come out with it first and tell me about what happened. However, it seemed like Dad had no intention to do that, at least not for right now. Maybe he was just trying to spare my feelings, but he never told me "I sucked your grandpa's dick. Just like you, I am a dad-sucker."

    The weeks went by, and I started to get ready for the trip back to London. It was the beginning of August and the weather in San Francisco was wonderful, but I had to go back and spend some time with Mum's side of the family before the school year started. The Sunday before I left, Blake and I decided to go shopping and hang out, doing typical teenage stuff together.

    Of course, walking around San Francisco, we were surrounded by a ton of hot gay men. Since Blake and I were both openly gay, the conversation often turned to us rating the hotties around us and choosing whose pants we'd like to get into (and we weren't being very choosy).

    "Blake… What was your first time like?" I suddenly asked as we sat at a kitschy diner in the Castro. Even though Blake and I liked to joke about sex, I'd never actually asked him this personal question before.

    "My first time fucking? I've… never actually done that," Blake said awkwardly, even though he was obviously trying to sound nonchalant about it.

    "Really? Wow," I replied. Since Blake often talked about sex without shame, I kinda assumed he was getting a ton of dick, especially in a place like SF. "Not that that's bad! I mean… I just assumed you had, but it's totally cool if you hadn't," I was quick to add.

    "I've done other things," Blake added. "I quite like sucking dick."

    "Ha. It runs in the family," I thought and cracked a smile.

    "My first time doing that was with our school team's quarterback," Blake continued, obviously trying to impress me and show me he wasn't some innocent virgin.

    Growing up in the UK and watching a lot of American teen movies, I was often confused by concepts like "school sports" and "school spirit," which was not something we did back home, especially not to that degree. So when my uncle told me how a while back, when he was writing for the school newspaper, he got to interview their team's quarterback and ended up sucking his cock, it sounded like an American movie to me; a movie that was equal parts teen flick and porn. It only got raunchier when Blake told me that after that, the quarterback left a raving review with the rest of the football team, some of which occasionally came to Blake now and had him service their cocks.

    "Wow!" I said, positively impressed. Even though he was an anal virgin, my young uncle's sex life seemed pretty crazy and hot.

    Under the table, I was sporting a semi that I tried to rub discreetly. I told Blake that my first time having sex was with Ben. Blake, who was a huge fan of Ben's modeling career, let me know how jealous he was. Then, he added that he himself had sucked Ben's dick a year ago.

    My uncle and I continued talking about Ben and how hot he was until we ran out of material. Then, we both checked our phones, which we'd been ignoring for most of the day.

    "Huh. Did you know today's Gay Uncle's Day," Blake said to me.

    "What?" I asked.

    "You know how they have a day for everything? Apparently today's Gay Uncle's Day. And I'm gay and I'm your uncle, so it's technically my holiday," Blake smiled proudly.

    "Okay, Uncle, well let me pay for our food then," I said and I got the check.

—

    Back at the house, Blake came to my room to help me pack. He wasn't really much help; he mostly just sat on my bed while I took socks and underwear and all the new clothes I'd bought and tried to fit them in my overstuffed suitcase.

    "Wow! These are hot," my uncle said and reached for a jockstrap from my pile of underwear. It was the white jock that my dad bought me for Christmas last time we were here. "Mind if I try 'em on?"

    "Umm. Sure, go right ahead," I said to Blake. 

    "I know it's weird to be trying on someone's underwear but I've… I've never actually worn a jockstrap before," my uncle explained as he shook his clothes off. With his back turned to me, I didn't get a view of the front, but I got a VERY good view of Blake's bubble butt as he slipped the jockstrap on. Once he did, it only made his cheeks look even better! I was quite proud of my own arse, but my uncle could definitely give me a run for my money.

    "How do they look?" Blake asked, turning around and letting me check out his family jewels as well, stuffed in the tiny pouch of the jock.

    "Looks great!" I said truthfully. Looking at himself in the large mirror, Blake turned around a few times, checking out his arse (which was exactly what I was doing as well).

    "Callum… Can I ask you something?" Blake turned to me. "You said you've been fucked by Ben but have you… ever fucked anyone else?"

    "Umm, no," I admitted.

    "So do you think you're a 100% bottom," my uncle asked. Even though he was asking about me, I could tell that he was also trying to figure out his own sexuality, which wasn't particularly easy for gay guys our age to do.

    "I don't know. Sometimes I think I might be, but how do you really know without giving it a try?"

    "That's what I mean!" Blake said, and then surprised me by adding, "So, would you like to try?"

    "Try what?" I asked.

    "Try being a top."

    "Yeah, sure."

    "I mean, right now. With me."

    My young uncle stood in front of me, looking at me hopefully. Behind him, I could see his arse reflected in the mirror, and I couldn't deny that his offer sure was tempting.

    "Are… Are you sure?" I asked.

    "Yes. To be honest, I'd love for my first time to be with you," Blake told me. "I trust you. And you're going back to London, so this can just be a fun little thing we do before you leave. My Gay Uncle's Day present."

    I smiled, and so did he. Noticing the effect his arse was having on me, Blake turned around so I was directly faced with his butt again. Without asking any more questions I fell to my knees and commenced with every good top's task: the rim job.

    Holding my uncle's cheeks in my hands, I spread them open as far as I could, exposing his smooth, hairless hole. A virgin hole unlike mine, it was every bit as tight as you'd expect it to be. I licked my lips, closed my eyes, and dove right in, touching Blake's arsehole with the tip of my tongue.

    "Mmmm!" my young uncle moaned. I'd never even kissed Blake and here I was, kissing his arse lips for the first time. My tongue slid up and down Blake's crack, focusing on his slit. Unlike my dad or Ben or Paul, Blake smelled different. He lacked the manly musk those older adult men had; but Blake's smell was not at all unattractive. In fact, I was surprised by how nice his arse smelled and tasted. 

    After a couple of minutes, I felt my uncle's hole relax and open up, allowing me to penetrate it with my tongue. My lips were now kissing Blake's arse lips, sucking on them and fighting the temptation to take a bite. With my hands on my uncle's thighs, I felt the hair that was there start to raise and goosebumps appear. 

    "Any of your football buddies ever did this?" I asked Blake.

    "Mmmmmm, no," he continued to moan, leaning against the mirror and pushing his arse out into my face, causing me to suffocate.

    I was popping a semi in my pants by this point, just like earlier at the diner. This time, there was no need to be discreet about it. I pulled out my cock and started wanking while feasting on Blake's arse. After I reached full erection, I took some of the precum I was producing and rubbed it on my fingers, bringing it up to my uncle's hole and using it as lube. When my tongue went inside Blake's hole next, I could taste myself inside of him.

    After fifteen minutes, Blake seemed relaxed enough to finally take a dick, at least as far as I could tell with my limited experience. Looking down at my boner, it didn't look like the biggest cock in the world, but maybe that was only because I was comparing it to a giant like my father's. 

    "You ready?" I asked, getting up behind Blake and placing my hard-on between his arsecheeks.

    "Yes. Go for it," he granted me permission, pushing his bum out even more.

    I peeled my body off of Blake's and quickly retrieved a bottle of lube I had in my room. I was just about to slather some of it on my cock before Blake stopped me.

    "Wait. I wanna suck you off first," my uncle said. Next thing I knew he was on his knees in front of me, wrapping his lips around my meat like I was the school's quarterback.

    "Mmm. Fucking nice," I said, enjoying the expert blowjob I was getting. A few weeks ago, Dad and Grandpa. And now, me and Blake. This house really was like a sex planet.

    You could tell Blake had been sucking cock for a while now. All those presumably straight boys at his school had taught him how to do a good job. Maybe he didn't need a lot of teaching in the first place. It sure seemed to run in the family.

    Blake's lips were carefully covering his teeth, massaging my shaft as he bobbed up and down on it. He was good… too good! If he wanted me to fuck his arse, he needed to stop before I came in his mouth.

    "Stop. Turn around," I told him and flipped him up against the mirror again. I took the lube and applied some on my dick before smearing some on Blake's hole as well. As I rubbed the lube on there, Blake's arse lips pulsed open and closed, devouring my fingertips and begging for something more substantial.

    "Here it comes," I announced, sliding the tip of my dick inside my uncle. I expected him to hiss and squirm, like the first time I did when taking a cock up my bum. But, other than some moaning and deep breathing, Blake managed to take it surprisingly easy. 

    "You alright?" I checked in on him.

    "Yeah. Keep going," he nodded, and I felt his arsehole pulsing again, sucking my cock in by itself without me even needing to push much.

    Before I knew it, I was halfway inside my uncle's hole. A few more inches, and I was in balls-deep. "Fucking hell, you're a champ!" I offered my praises to Blake.

    "You just did a good job opening me up," he said humbly, turning his head over his shoulder to face me. Then, in a moment of undeniable sexy passion, I leaned forward and planted a big kiss on my uncle's lips. I shoved my tongue in his mouth at the same time as I shoved my dick up his hungry arsehole. Blake reciprocated, sucking on both of my organs.

    "Holy shit," I panted. I hadn't expected to find myself topping anyone, but this felt amazing. Blake was right: this was the perfect way to end my summer in San Francisco.

    Sweat was running down my spine and into my arse crack. As I started thrusting, the moves came natural to me. The soft insides of Blake's body felt incredible on my cock, squeezing it and milking the precum out of it. I regretfully had to admit that I probably wouldn't last long.

    "Don't worry about it," Blake reassured me. "It's no big deal. Just keep going."

    "Alright if I cum inside of you?" I checked.

    "Yes. Fuck yes. Load me up," he grunted, and we dove in for another passionate kiss.

    I actually managed to fuck Blake for almost ten minutes, which I didn't consider too bad. My young balls were begging to bust, and I couldn't deny them the pleasure any longer. I humped my uncle like a dog in heat, set on breeding. I grasped onto the waistband of my own jockstrap that Blake had on while I fucked him. In the mirror, I saw that Blake had taken his own hard cock out of the pouch of the jock. He wasn't wanking, but his cock looked close to cumming nonetheless. Maybe if I did it right, I could fuck it out of him.

    A few moments later, there was no more holding back. "AAAAH!!!" I shouted and let my balls explode inside my uncle's guts. I filled Blake up with my young sperm, letting his bowels taste cum for the very first time. But my proudest moment came when I saw Blake shoot his load all over the mirror hands-free. I'd managed to fuck a load out of him! Even if I never topped again, I would always have that accomplishment under my belt.

    While still unloading inside Blake's guts, I brought my fingers to the mirror and took the cum that was on there, bringing it up to my uncle's lips and feeding it to him. Then, I scooped up some more and got a taste of it myself, swallowing my uncle's babies while shooting my own inside his no-longer-virgin arse.

    "Phew. Fuck. Holy shit!" we both spewed obscenities. After my balls were all empty, I slowly pulled out of Blake's hole, which closed shut immediately after, retaining my cum.

    "Can I keep this jockstrap?" Blake asked me with a satisfied grin on his face and a bucketful of sweat running down his forehead. 

    "Sure, Uncle Blake," I said. The jock was a present for Dad, but I could get him to buy me another one. It had brought good luck to me, and now it was time to pass it on to my uncle.