JOSH:

    With all of the back-and-forth traveling and bonding time spent with my son, I was falling behind on my dating apps. One rainy evening, I came back home from work and decided to log on and scroll through the over 100 messages I'd received, some of them from fresh faces, and others from women I'd talked to in the past.

    Since the weather was horrible and I was in no mood to go out, I found myself with plenty of time. While I lay naked in bed with some random show playing on TV, I scrolled through all of the messages, replying to some but ignoring the vast majority of them. I remembered my goal of landing a wife before I turn 40 (fourteen months to go) but that mission had been put on the back burner lately, seeing as I was prioritizing my relationship with Callum.

    Finally, after having scrolled far enough in my inbox, I found the last message from… Cat. Seeing "her" photo still evoked fond feelings in me, even though I knew she wasn't real (or rather: she was some random photo off Google Images). I tapped open our chat history; in a bizarre way, a part of me still felt like this was an exchange with a woman who was no longer in my life. As I scrolled through the explicit – and at times romantic – messages, I had to actively remind myself that it had all been typed by my son. By now, the anger and betrayal I felt when I first found out about the catfishing had dissipated. As I read our old texts and watched some of the sexual videos we'd sent to each other, I felt a weird sense of nostalgia. I found myself typing the words "I miss you" and hitting Send.

    Ten minutes later, just as I'd begun jacking off to kill the time, I got a notification on my phone. It still said "New Message from Cat." I smiled, and while working my boner with my left hand, I tapped open the message with my right. It was a simple "I miss you too, Daddy 🥰." It was something that Cat might say, as she – just like Callum – called me that. 

    My left hand stroked up and down until there was enough precum oozing out of my piss slit that I could now hear the fapping motion echoing in the room. While I looked for what words to type next, I was beaten to the punch. I received a new text asking: "What you doing?"

    "This," I replied, sending a photo of my hard, precum-soaked dick. As a response I got a string of emojis: "😛😛😛😛😛😛."

    "I'm out with some mates," said the next text, "but if you want I can come take care of that for you 🍆💦."

    Just like that, "Cat" and I had a date. Half an hour later, there was a knock at my door. Still naked – and still hard as a rock – I went to answer it. Standing there and grinning like a joker was my son, his wet hair sticking to his face, making him look extra devilish.

    "Mind if I come in and get out of these wet clothes?" he said, inviting himself in with a confidence he certainly lacked when we first met.

    "Sure," I answered, smiling back. "But you gotta be quick, I've got a lady coming over soon."

    "Oh really?" said Callum, giving me a kiss as I shut the door. "Who is it?"

    "Oh, just this woman named Cat that I'm really into," I continued jesting. 

    "Well I'll make sure to leave before she arrives," Callum smirked before burying his tongue back in my mouth. 

    His wet clothes sticking to me felt uncomfortable for both of us, so I made sure to take them off as fast as possible. As I pulled my son's pants down, I found myself facing his uncut cock, in a state of semi-arousal after our passionate making out. I parted my lips and just like I'd done in the past, I took Callum's teenage prick in my mouth.

    "Ahhhhh, Dad," he moaned out loud, combing his wet fingers through my hair. I stayed squatting down for a while, sucking my son off until he was just as hard as I was. I would've kept going but Callum interrupted me by saying "My turn" and going down onto his knees so he could suck me in return.

    Unwilling to deny him his treat, I stood up and allowed my boy to take my dick in his mouth. He sucked it up like it was a pacifier offering him comfort. While blowing me, Callum placed his hands on my glutes and squeezed. I found myself flexing my muscles and thrusting my hips, fucking my son's face, venturing deeper down his throat until he'd started gagging. Whenever he choked, I let Callum catch his breath for a couple of seconds before getting right back at it, face-fucking him like there was no tomorrow. I could cum right down his gullet, but I knew my son would prefer my cum somewhere else.

    "Want Daddy to fuck your pussy now, huh?" I grunted, filling the horny teen's throat so he couldn't say anything but a "mhm" in response. Once I got to the very edge, I pulled my tool out and left it throbbing in my son's face for a few seconds, holding back from cumming just let. 

    "Let's go to Daddy's bedroom," I said. Callum stood up and we got entangled in another passionate kiss, going on for several minutes all the while stroking each other's slicked up cocks. 

    Finally, we made our way to my bedroom. From my "sex drawer" I took out a bottle of poppers, allowing Callum to indulge in a few huffs while I went to eat his ass. Every time my son took a hit, I felt his hole loosening up around my tongue, which gave me the opportunity to bury it deeper down my boy's chute. Now that his mouth was empty, Callum "Ahhhhh!"-ed and "Mmmmm!"-ed loudly, swearing like an angry sailor. His sex noise reached its peak when I grabbed my hard cock and swiftly shoved it inside his cunt, piston-fucking my son like a whore… which was just the way he liked it.

    "Fuck yeah, Dad! Wreck that hole!" he begged, opening up wider for me. "Fucking ruin my cunt!"

    "Yeah? You want it all stretched out and sloppy?" I grunted in between my aggressive thrusts, my balls smacking loudly against Callum's thighs.

    "Fuck yeah. Stretch it out real good," he moaned, taking another hit of poppers.

    We fucked like this for almost half an hour, until I could take no more. With a loud "FUCK!" I deposited my DNA inside my son's asshole, breeding his guts with the same sperm that made him. It made Callum blow his own load handsfree, shooting his cum all over my sheets while riding my dick.

    "Fuck, Dad. That was intense," my boy said when we were done jizzing. With my cock still inside of him, I pulled Callum in and gave him a kiss on the back of the neck. Slowly, he pulled away and let my cum-covered prick plop out. Securing the lid on the bottle of poppers, he crawled toward my nightstand to put them back in the drawer.

    "Oh my god, you still have this?" Callum suddenly said, pulling a box out of my sex drawer. 

    Almost a year ago, I took my son to a Soho sex shop and brought him an assortment of butt plugs and dildos. Back then, Callum was just getting started with bottoming, and he was worried that his hole might be "too tight" to ever take a dick. Ha! If only he knew that several months later he'd be a seasoned pro with a sloppy hole. The day when we got all the ass toys, I helped my son practice with the smallest of the butt plugs. After we were done, he took all the toys to his mom's flat, but he walked out of my flat with the smallest plug still in his ass – so he didn't need a box for it. To this day, I still saved the box in my drawer.

    "You know, Dad, I don't know if I ever thanked you for being so cool," my son said now. "Like, thank you for taking me to that shop and buying me all those toys to practice with that time. They were a HUGE help. A couple of weeks ago, I met this other gay boy at school, he's a year younger than me. We got to talking about sex and his parents are super prudish; like, they'd never talk about sex, especially anal sex. And we had sex ed at school but that hardly explained anal stuff either. So, I realized how lucky I am to have you, to support me while I was figuring it all out."

    "Aww. Trust me, I'm the lucky one, Son," I smiled and gave my boy a hug.

    "I'm done with those smaller toys, by the way," said Callum. "You can have em back if you want."

    "Hahaha, I think you can keep em."

    "They felt REALLY good. So gay or straight, I think every bloke should give em a go."

    I thought about this for a second. With all of the anal sex I'd been having lately, I'd be lying if I said I wasn't growing curious about my own hole. Besides, the thought of using the same ass toys that my teen son had already used kinda turned me on.

    "You know what… why don't you bring those butt plugs over next time you drop by?" I said and watched a mischievous grin take over my son's face until he looked like the Cheshire Cat.

 

CALLUM:

    Before bringing my old sex toys to my dad, I made sure to use them one more time while enjoying a wank and watching the hot videos that he had sent "Cat." Afterwards, I gave them a quick rinse and brought them over to Dad's flat one weekend, offering to help him get started.

    "Well… I did assist you your first time," Dad recollected. "So I guess it's only fair."

    My father and I took our clothes off and went to his bathroom, where I slathered the smallest butt plug with lube and started inserting it up Dad's hairy hole. My dad's arse was never particularly hairy compared to some men out there, but he did have a fair amount of hair in his crack, which was soon sticking to his cheeks thanks to the lube. 

    "Ah, fuck!" Dad gritted his teeth as I shoved the tip of the toy inside of him. By now, I could take this plug without blinking an eye, but my father was still a beginner. 

    "Shhhh, it's alright. Just breathe," it was my turn to soothe him now, thinking back to the first time I took this plug in this exact same bathroom. 

    My father breathed, and his arsehole relaxed. Another inch of the toy disappeared from sight, until it was all in to the hilt. "Good job!" I lauded Dad and smacked his arse. He smiled proudly, wagging his hard cock in my face, and it wasn't long until that same cock was in my mouth, and then later: up my arse. Dad fucked me while maintaining the toy inside his arse, which he said felt mind-blowingly amazing afterwards.

    Meanwhile, my Grandpa Ron was still gallivanting around Britain, visiting places like Edinburgh or Oxford and reconnecting with people he knew there. Whenever he was in London, he took us out to dinners at the city's poshest restaurants – places I'd never thought I'd get into growing up. Although it was interesting at first, the novelty had quickly worn off, and I found myself looking forward to being at Dad's or Grandpa's flat more than any of the fancy restaurants or bars we would frequent.

    On one such night, the three of us enjoyed a nice meal and then retreated to Dad's flat. Once there, Grandpa quickly reverted to one of his favourite topics of conversation: sex. I could tell that he was flirting with me (at the lack of a better word), hoping to "score some ass," as Americans might put it. Since the night when Dad and Grandpa spit-roasted me, my grandfather hadn't been back inside my arse. Once again, we were all a bit tipsy – the perfect amount to get us in the mood for trouble.

    "You know… Dad has been practising a new skill," I revealed to my grandfather with a wink.

    "Oh really? What is that?" Grandpa made eye contact with Dad.

    "I don't know what he's talking about," my father replied coyly.

    "Oh, c'mon." I decided to be a snitch and I told my grandfather all about Dad's venture into arse play, and how he was using toys to get his hole used to the sensation.

    "And what's the end goal, taking a dick some day?" Grandpa asked Dad.

    "Not necessarily," Dad said, surprising me with his reply, since it wasn't a flat-out "no."

    The overpriced scotch I'd been drinking was starting to hit me. Since I was in a shit-stirring mood, I turned to Dad and I said,

    "Well, if you're ever looking for some good dick, I know where you can find one."

    "Oh yeah?" Dad smirked before taking a sip of his drink. "Where?"

    "Right there," I said, pointing at my grandfather. After all, Granddad had fucked me on more than one occasion and I could vouch for him as a top.

    I expected both of my family members to burst out laughing, and maybe call me a twat or something like that. Instead, Dad and Grandpa just made eye contact once again, staring intensely at each other and they seemed to… smile.

    "Well, you've already sucked my dick…" Grandpa said.

    "I don't know if that's quite the same," Dad replied.

    "There's a first time for everything," Grandpa reminded his firstborn son.

    "Okay, enough fooling around," my father said, breaking eye contact and looking down at his glass.

    "Oh, I ain't fooling around," Grandpa assured him. "I'd fuck you if you wanna try."

    I watched my father's Adam's apple go up and down as he swallowed and said,

    "Shit. Dad… You're serious?"