Operation Simon Pt. 01

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My friend plans to hook up with his son like I do with mine.
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Part 1 of the 4 part series

Updated 06/08/2023
Created 05/31/2017
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"So what's the plan?" I asked Guy.

It was Wednesday evening and he and my son Jake were slouched on the settee working their way through a pack of beers while I was sitting opposite with a glass of wine.

"I dunno," Guy shrugged. "It's gonna be a difficult one. We're gonna have to play it dead careful 'cause I sure as fuck don't want him tellin' any tales to his mother."

We were discussing what we were going to do on Friday night when he brought his own son, Simon, around for a little get-together at my house. That in itself wouldn't pose much of a problem, but Guy had an ulterior motive which made detailed planning absolutely essential.

"You still want to start playing around with your kid then?" Jake asked without taking his eyes from the movie the three of us were half-watching.

Guy chuckled. "He's your age, Jake... just gone twenty-one. Don't make this sound any more weird than it needs to..."

"You wanna shag him, though," Jake persisted, still staring at the TV. "I mean, that's your ultimate aim...?"

"Not necessarily," Guy replied. "I just really like what you guys have together. The way you use each other for sex is kinda logical really... you're both men and you both get horny so sometimes you help each other out. That's how I want it to be with Simon."

"You want to get sexual with your son?" I asked. "You're absolutely sure about that?"

"Maybe not at first. I want him to see how it works with you pair... how natural it looks for a dad and a son to get physical together..."

"You want us to get intimate in front of him?"

He shrugged. "Perhaps, yeah... but nothing too heavy. He's gonna freak out big time if you guys treat him to the demo you showed me..."

We'd been staying over at a Travel Lodge before going to the Liverpool match. Jake and I had surprised our companion by showing him that we'd started having occasional but extremely fulfilling incestuous sex. My son had bobbed down to consume a good half of my large erection in front of Guy's disbelieving eyes and then we'd awoken him next morning by Jake taking me roughly from behind as we'd squatted alongside him.

"Maybe we play a game of 'Twister'," Jake suggested. "I end up with my face in my dad's butt and say, 'Oh Jesus, his arse-crack smells so fucking horny!' and Simon'll be like, 'Aw fuck yeah... I gotta have a sniff of daddy ringpiece for myself!'"

Guy sniggered but shook his head. "Come on, buddy. You know as well as I do that Simon's not like that. He'd run a mile if he had to shove his face in my arse. I'd be up for having a sniff of his, but if I did he'd probably run a mile too!"

"But maybe the game idea is worth pursuing," I proposed. "It would keep things light-hearted."

"How about strip poker, then?" Guy asked. "Once we're all stripped down to the buff, we change the rules so the loser has to wank the winner. Simon gets to see Jake giving daddy's big dick a good pullin'... so next time when he loses he won't be so shy about reachin' over and playing with mine!"

"Can you really see Simon agreeing to play strip poker?" Jake laughed. "I guess we could start out playing for pennies or something, but even then he'd probably say he felt uncomfortable with gambling."

"I agree," I chipped in. "The game would have to be played purely for fun but then gradually manoeuvred in a sexual direction."

"Okay..." Guy replied, staring over at the fireplace as he struggled to come up with something that would fit both requirements, perhaps thinking back to his days on the oilrig.

"Truth or dare?" Jake tentatively offered.

"Yes... that's more like it," I agreed. "How about we make it a card game and arrange the order of the tasks very carefully beforehand...?"

Guy looked unconvinced. "So how would that work?"

"We can have the top cards giving people silly dares at first, but we can set it up so that after a few rounds Jake's task is to get the person to the left of him sexually aroused... which will, of course, be me."

"Okay," Guy grinned. "I like where this is going!"

"Jake will whisper stuff into my ear and I'll deny that I'm getting at all turned-on and then you, Guy, will insist that everyone can see whether I really am becoming aroused. After some initial reluctance from me and hopefully some persuasion from Simon, I'll pull my penis out through my trouser fly and show the room that it might be long and thick but it is unquestionably limp."

Jake asked, "You won't mind Simon seeing your todger?"

I shrugged. "I used to take you pair camping when you were younger... he's seen the thing swinging around between my legs many times before..."

"Okay," Guy chuckled, "since sonny-boy's whispering hasn't done much for daddy's droopy dick, Jake resorts to reaching over and having a little fondle of it!"

"Oh sweet!" Jake guffawed, just about to take another swig from his beer. "That'll be so cool... Simon watching me having a squeeze of my old man's donger sticking out from his fly!"

"And what will you be doing?" I asked Guy.

"Cheering and egging Jake on... trying to get Simes to join in... I reckon he'll up for it, actually... he'll probably find this really funny..."

I smiled. "So I say, 'Okay, it's getting a bit stiffer, I think that's a win, Jake.'"

"And I'm like 'No way!'", Guy laughed, becoming increasingly enthusiastic about the plan. "I call over, 'Come on, guys, the dick's gotta be fully hard! I wanna see the bell-end go shiny... that's the sign of a proper boner!'"

"So I wrap my hand around your big knob and start wanking you off," Jake grinned at me. "I mean, actual masturbation... with your foreskin sliding up and down."

"Aw yeah!" Guy chortled. "And I'll be like, 'Oh my God... this is so fuckin' funny!'"

"Would you still be okay with that, dad? Having Simon seeing my wrist bashing away and making your cock grow a stiffy!?"

I thought about how we would look: me perched on the settee with my large phallus exposed through my gaping zipper and Jake reaching across to eagerly stimulate it. Simon would likely look surprised - though hopefully also amused and intrigued - watching his friend masturbating his father right in front of him. I'd chuckle back at him as my manhood achieved its full proud stature inside the grip of my son's fingers, until the domed helmet throbbed as two shiny purple lobes.

"Yes," I grinned, "I think I'd rather enjoy it!"

Often when Jake's sleepover buddies are lumbering out of his room for a pee in the morning, I make enough sound from behind my half-open bedroom door to let them know I'm enjoying a moment of self-induced pleasure. Sometimes a young man will creep along the corridor to take a peek at their friend's father vigorously tending his morning hard-on. I sit opposite the door so that if an inquisitive face cranes around it, I can smile at the young man while my hand pumps frantically up and down, and my two big bollocks slap up against my fist. Occasionally my performance will be rewarded with a cheeky smirk and a growing bulge in the boxers, in which case I flaunt my huge erection as I wank it until we're both staring, mesmerized, at my blasting gusher of cum.

"Perhaps Simon will too," I mused. "Some young men find the sight of mature male masturbation very appealing!"

"You reckon?!" Guy blurted his beer out laughing. "Well if that's right then maybe our Simes will start popping a boner himself..."

"Will we be able to see it if he does?" I asked. "I mean, will it be obvious in the front of his trousers?"

"Yeah, he's got a long dick," Guy admitted. "It can make his pyjama shorts stick up dead high like a flagpole!"

"He's got a nice cock," Jake nodded. "A bit small when it's limp, but it grows really, really long when he's horny."

When Guy and I looked quizzically at him he explained, "We used to wank off together a few years ago. His cock would get longer than mine but nowhere near as thick."

I went on, "Okay, once Simon's trying to conceal the rising tent in the front of his trousers, I announce that my penis is now fully engorged so Jake stops rubbing it and we all laugh at the dare. After that I casually mention that, being so sexually comfortable with my son, it's not the first time that Jake's hand has given me relief."

Guy nodded. "So then I'll ask you, Rob, if you ever help laddo out with his stiffies."

"And I'll say, yes of course... I think it's a very fatherly thing to do."

"Yeah, that's it!" Guy laughed. "Simon likes a good wank... he spends most of his time in his bedroom bashin' his prick off! I reckon he'll like the idea of having free handjobs on tap from the other bloke in the house!"

"Will you still have your cock out through your fly, dad?" Jake asked. "I mean, will you be sat there with it standing up on full bone?"

"I can be," I nodded. "It grows very large, as you know, so I can say it needs a few minutes to soften enough to tuck away. Why?"

"Well, your turn is next so maybe the card could dare the other players of the game... us three... to pull our cocks out too. Mine will be rock hard from wanking you off... you know how I like the feel of it... and we reckon Simon's will be running wood by now..."

"Mine'll be nicely firm after watching Jake get to work on daddy's dong," Guy chuckled. "So yeah... that'll be hot... the four of us sitting around with our pork-swords raised high on full salute!"

"Actually, that'll be hilarious!" I grinned. "Surely even Simon will be enjoying the evening by now... especially after he's had a few beers down him!"

"So let's say he's sat right next to me with his foot-long stickin' out through his trouser fly," Guy proposed, "d'you reckon he might be up for me reachin' across and givin' it a rub?!"

I nodded. "We could set it up so that the next card dares you to do just that!"

Guy wavered, mulling the idea over, before saying, "No... on my turn the card says I have to admit something secret. So I say, 'I like how you guys are so chilled with each other that you can do sex stuff together without it being a big deal. I think it's awesome, actually.'"

"Would you like me to ask you if it's something you'd want to do yourself?"

"Yeah," he nodded. "And I'll be like, 'I reckon I could... I think me and Simes are cool enough for it not to be a big deal.'"

"Okay," I chuckled, fairly sure that his son would by now be realising where the evening was heading.

Guy went on, "So the next card he takes dares him to wank me off. I reckon by then he'd be up for it... he's seen you guys doing it... heard that I'm okay with it. He'll probably lean over and give daddy's thick dick its first taste of son-stroke!"

Jake grinned over at him, acknowledging the pun while he took another swig of his beer. Then he said, "If you can get him wanking you off, I reckon you'll have him sucking your cock after a couple of weeks."

Guy nodded enthusiastically, no doubt envisaging many pleasant evenings to come in which his son would be kneeling in front of him, bobbing merrily at his crotch.

"Full anal intercourse will take rather a lot longer," I suggested.

"I don't mind if we don't fuck. To be honest, I mainly want him to suck my cock if he's home and I'm horny."

"You really don't like having to use your own hand," I chuckled. Guy would only rarely masturbate so, when we did get together, he was always extremely horny and desperate for us to have sex.

"It just seems such a waste... me jazzin' my dick off while he's in the next room with a nice wet gob that could be slurping up and down it!"

Jake asked, "Would you suck him off? I mean, if he did the same you...?"

"Come on, I'm not selfish," Guy shrugged as if it was a ridiculous question. "I worked on an oilrig, mate... I know how give and take works!"

Jake smirked, "So if eventually Simon were to let you fuck him, would you be okay with him doing the same to you?"

"'Course I would," laughed Guy. "He's got a lovely round arse and when he bends down you can see the tightest little pussy hiding between his cheeks. He could have his turn on my bigger, hairier version, as long as he bends over for his old fella and lets me baste off up his!"

"Does he have anal sex with his friends?" I asked. "If he enjoys intercourse with them, he'll be more open to the idea of doing the same with you."

"I really don't know," Guy mused, his eyebrows furrowing with thought. "I mean, sexually, he's incredibly secretive... apart from all the wanking off he does when he's on his own in his room."

"Does he look at males or females when he masturbates?" I queried.

"I don't even know that... he passwords all his devices and these days you don't find dirty mags in lads' rooms. He has a lot of mates he hangs about with but there isn't a particular guy he mentions more than the others. He talks about having girlfriends but I think they're just girls he's friends with, not girls he's dating."

"I reckon he's straight," Jake observed, before treating us to an especially noisy belch. "When we used to wank off, he never even once suggested we did anything more so I think he's into girls but probably just too shy to ask any of them out."

"Or maybe he was just too shy to ask you?" I suggested.

"Maybe," Jake shrugged. "But he'd always get really uptight about gay stuff. I mean, at scout camp and stuff when lads were messing around, Simon would get all prissy even when it was just meant as jokes."

I took a drink from my wine and when it became clear that there was no further speculation to be had about Guy's son's sexuality, I decided I'd summarize the course of action we'd now agreed.

"So stage one of our plan is for us to play a game which gets increasingly sexual on Friday night after Simon has had a couple of drinks. We get him comfortable with the idea that it's perfectly natural for fathers and sons to enjoy a physical connection, and then we see if he's willing to masturbate his dad."

"Or just touch my prick," Guy clarified. "See what it feels like..."

Jake nodded before suggesting, "Maybe pull your foreskin back... see daddy's one-eyed monster!"

"If I'm boned, my skin'll already be right back and my chub-end'll be out like a big red lipstick! Maybe he could touch it and make me wince from how sensitive it is... that could be kinda funny... having him touch his dad's cherry-popper to see how much I shudder!"

I coughed, wanting to get back to formulating our plan.

Then I continued, "How successful we are during stage one determines how we progress things thereafter. We'll reassemble before he comes around for a second visit so we can decide how we're going to proceed during stage two."

"Fuckin' hell!" Guy laughed. "This is like 'Operation: Simon'!"

"Wasn't a free holiday mentioned for the four of us if we can get him to first base?" Jake chuckled as he reached for another bottle of beer. At the Travel Lodge Guy had specified a number of destinations depending on how receptive Simon was to getting frisky with his dad.

"Yeah, that's the deal," Guy agreed. "If he admits he likes the idea, we go to Paris. If he gropes me, Barcelona. A handjob, New York. L.A. if he gobs me off."

"And a butt-fuck gets us to the moon," Jake laughed.

"There's no way in hell he's gonna be up for doing that so soon, but if by some surreal turn of events he does end up taking a stiff one up the arse, I'll dip into my savings and we'll go to Australia."

"Wow!" I grinned over at Jake. "We've really got to make this work! We could go and pay your cousin Shane a visit while we're out there."

"Okay, you're on," Jake chuckled. "Let 'Operation: Simon' commence!"

===

A few hours later, I was sprawled on my bed with my large cock standing upright, its round helmet full and shiny, and my face enveloped by Guy's big backside. His lush hairy crack was smothering my nose and mouth, the two cheeks he sits on pressing into those I blush with and his two bollocks resting heavily on my chin. I was revelling in a long, leisurely face-sit, sniffing my boyfriend's deliciously pungent rear while my tongue was savouring the meaty flavours of his opening and teasing the delicate flanges surrounding it.

Suddenly I heard Jake's voice as he strolled into my bedroom. "You fellas up for some fun? I'm horny as fuck!"

He saw Guy squatting over my face, his own cock as excited as mine and curving upwards between his legs, and laughed, "Aw yeah... nice one! You mind if I join in with big boys?"

"Fine by me," Guy chuckled. "Your dad can't reply, what with his tongue being shoved up my arse, but I reckon he'll be okay with it!"

"What do you think, dad?" my son asked as I nuzzled deeper into Guy's wonderfully flavoursome butt-cleft. He'd been out on a job today, plumbing in a new build, and his arse gets especially sweaty and musky after a day of manual labour.

"Okay, let your cock answer," Jake said when it became clear that my mouth was currently for rimming and not for talking. "One twitch means yes, two twitches no."

I twitched my cock just once and Jake laughed, "Cool! Let's have a bit of fun!"

Jake stripped off the t-shirt and shorts he'd been about to sleep in, saying, "I was just gonna have a wank and then I thought why am I lying here rubbing one out when the good stuff's going on next door?"

"See, that's exactly how I want Simon to start thinking. There's a nice wet mouth waitin' for him in his dad's bedroom... as long as whatever I do for him, he does back to me."

"How d'you want me, then?" Jake asked.

"Suck my cock while your dad eats my arse out."

"Yeah, and what's in it for me?"

"You could stoop over him," Guy suggested. "Frot your cocks together while you get to work gobbin' down on mine."

That sounded interesting. I'd never frotted properly with Jake and, with the thick girth of his erection and the veiny roughness of its shaft, I thought it would be most arousing for us to thrust our two large manhoods together.

But Jake seemed rather less impressed. "I'm not really into dick-on-dick stuff. I don't mind a sword-fight but that's more of a two-way thing."

"Well, sit on his cock, then," Guy tried instead. "Slide your arse up and down on it while your mouth does the same to mine!"

"Will you wank me off if I do that, dad?" Jake asked. "Stroke my dick same speed as I'm butt-pumping yours?"

I managed a muffled 'mmmm' in response as I basked in tongue-fucking my boyfriend's behind, but Jake needed further clarification.

"Come on, one twitch yes, two twitches no."

I twitched my cock upwards and held it fully engorged above my stomach. Jake laughed at how high his dad's big hard-on was hoisted, with the head of it pulsating expectantly at the prospect of being smothered by his lovely hot, slimy bum.

"Okay... so one twitch and a pearl of precum forming on the slit," he chuckled. "I'll take that as a very emphatic 'yes'!"

I felt him clamber onto the bed and was waiting for him to lower his swollen opening down onto me, but instead I heard Guy say, "Wrong way round, buddy... your dad's cock's that way..."

"I need a bit of lube," Jake replied. "I'll hold my cheeks open... see if you can spit on the bullseye!"

Guy chortled and then hocked up a thick gob of phlegm from his throat. After three or four violent spits they both laughed and Guy called out, "That's got it... right in the fuckin' brownie!"

Jake pushed his luck a bit further and said, "Lick it in for me... go on... tongue it right into the hole...!"

"I'm not gonna lick your arse!" Guy laughed. "It's not like you're offerin' me a fuck!"

"Rub it in with your fingers, then," Jake suggested. Then he moaned gently and gasped, "Aw yeah... that's nice... work it deep!"

"It's like fingering a pussy," Guy giggled, as he slowly teased my son's gaping arsehole. "Only a pussy doesn't leave a stain on your fingers!"

"Fuckin' sniff it!" Jake urged him. "Go on... lean in for a nice long whiff while you're sliding in and out!"

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