A Gift from Grandpa
"Dad... Have you ever gotten a blowjob by a guy?"
My eldest son Josh surprised me when he popped this question. We were sitting at my second son Kris's wedding, which made Josh's query even more unusual. Surrounded by hundreds of friends and family members, I had no idea what made Josh think of this now but I decided to humor him.
"What, you wanna do it here? It's a bit public, but sure. Get on your knees," I joked, pulling on my zipper.
"Dad, stop fucking around! It's a simple yes-or-no question," he insisted.
"Yes, yes I have. Some of the best in my life," I said, looking across the well-populated wedding hall. Coincidentally or not, I made eye contact with an old acquaintance known by most as Colonel Brown (a moniker he received after serving in the Air Force when he was younger), who winked at me when he spotted me looking.
"Why?" I turned back to Josh, curious about his reasons for asking the question.
"I was just wondering how many straight men have done something like that. Turns out, quite a few," he noted and got up, jotting off before I had a chance to share my story with him. Too bad, as it was quite an interesting story as well. My very first blowjob ever was by a guy, as a matter of a fact. A guy in this very room.
By the time I turned 18, everyone around me thought I had everything I could ever ask for. My family – which had recently relocated from New York to San Francisco – was now one of the wealthiest families in our new city. It took a LOT for the cross-country move to happen; the Van den Bergs had been settled on the East Coast since the days of New Amsterdam. But my grandfather Ron, who I was named after, decided there was a lot of money to be made in California and, at least in our family's case, he was right.
On the day I became an adult in the beginning of the '80s, I immediately inherited a fortune bigger than what most people would make in their entire lives. I was always a confident kid – cocky even – and the social status certainly helped. There was just one thing I was insecure about, a secret I hid from everyone, an issue I lied to my friends about whenever it got brought up in conversation. It was something that bothered me deeply no matter how silly it might seem to anyone else. The problem was: I was still a virgin.
Growing up, I was always pudgy. Adults called it "cute," but by the time I reached puberty I realized it ain't something most people found attractive, especially when it came to sex. It fucked with my head royally. On the one hand, I had all the money and coolest clothes in the world. On the other, even at 18 years of age, I still hadn't gone further with a girl than kissing and groping. Not counting some over-the-pants action, no other person had touched my dick since the day I was circumcised.
One day, I learned that even my widowed grandpa was getting more action than I was when I walked in on him getting his dick sucked. The real shocker was: the sucker was a guy! A boy who looked barely a year older than I was! I stood in the doorway of the living room, watching the kneeling cocksucker slobber and feast on my grandfather's raging 9-incher, my head reeling. Grandpa and I made eye contact just as his throbbing tool went inside the servile boy's mouth. I quickly bolted out and didn't tell anyone, trying to ignore the stirring that took place between my legs when I witnessed the scene.
That night, my grandpa called me over to talk about the incident. When I asked him if he was "a fag" he said no, and told me not to use that word. He explained that sometimes men just "get urges" (the way he put it) and that any willing help was much appreciated. Apparently, the cocksucking boy was a year out of high school, without much direction in life, but one thing he was good at was sucking men's pricks, so my grandfather let him go down on him occasionally.
And then I got a kooky idea. If I let the guy suck my dick, would that maybe help me feel more relaxed around girls? I just wanted to get my first time over with, in an effort to get rid of some of my mental baggage. By this point, I was so insecure about my lack of sex life that I felt like this couldn't hurt. True, I could always go to a female prostitute – something I'd considered many times – but for some weird reason the prospect of doing it with a guy made me less nervous than going to a woman. Not because I was attracted to men; it was just the opposite. After some hesitation, I asked my grandfather "Would your… friend be willing to suck me off as well?"
That is how Grandpa Ron and I ended up getting blowjobs side-by-side from the same sucker. At first it was only supposed to be me, but the boy suggested that Grandpa stayed in the room and joined us. In the heat of the moment, we said "oh, what the hell" and we went with it. The guy did an excellent job, paying each of us equal amounts of attention. Whenever I wasn't fucking the boy's throat with my rod, I was watching him choke on my Grandpa's meat, which was shorter than mine but thicker, and surrounded by a forest of salt-and-pepper pubes. He was the first to shoot in the cocksucker's mouth, followed seconds later by me, his favorite grandson. I felt leftovers of my grandfather's spunk in the boy's mouth as I filled it with my jism as well. The whole thing was so hot, I could actually see this becoming some sort of ritual for us. Unfortunately, a few weeks later, the boy – urged by my grandpa to get his shit together and do something with his life – joined the Air Force.
"Hello, Colonel," I said to my old buddy, walking up behind him and putting my hands on his shoulders. "Care to join me for a cigar?"
Colonel Brown and I left the table and walked across the wedding hall, heading out to the yard of the palatial five-star hotel. Now in our late 50s, we were different people than we were in our teens, but one thing we still retained was our youthful libido. I knew this for a fact, because I'd had my cock serviced by the Colonel several times over the past couple of decades, ever since he left the Air Force and returned to San Francisco. Throughout my marriages to three women, and his marriage and divorce with his ex-husband, the Colonel and I remained faithful buddies that got together whenever "the urge" struck, to quote my late grandfather.
Out in the yard, surrounded by a few other smokers, the Colonel and I puffed on some Cuban cigars I'd brought, and after we were done we decided to go for a walk somewhere more private. Hiding behind bushes and shrubbery like two horny teens, the Colonel sucked my dick at my son's wedding. "This one's for you, Grandpa," I thought as I shot my spunk down the cocksucker's throat. He was every bit as good as he always was.
Four months after Kris's wedding, I got to see my eldest son Josh again when he visited from London for the Fourth of July. We celebrated Independence Day in my bed, where Josh gave me a handjob that made me cum all over my belly as well as his face.
Although my sex life had been off to a slow start as a teen, I more than made up for it in my 20s and onwards. I never lost the weight, but I learned that it doesn't have to impede me from being every bit as sexual and freaky as I felt on the inside. I fucked hundreds of women, occasionally engaging in a liaison with another man as well.
More than anyone, my firstborn had taken after me. From a young age – much younger than me – Josh was sexually (over)active. He would often share those experiences with me, and we had also done things like get our dicks sucked side-by-side at bachelor parties or such. I never knew anything about his potential experience with other men, but I knew that there had to be at least a little something there, curiosity if nothing else. It was impossible to be as sexual as we were and still completely ignore members of your own sex.
So the handjob on the Fourth didn't come as a big surprise. It was a spontaneous activity in the spur of the moment that I was all too happy to engage in. A couple of days later, Josh was in my study, running through his investment portfolio with me. I liked what I was seeing, even though I only half-paid attention to the numbers. The truth was: I hadn't cum since the thrust with Josh in my bed and I was getting too randy to function. Unfortunately for me, my wife was gone for a few days, so I had to seek release somewhere else.
"You know my buddy Colonel Brown?" I asked my son, changing the subject from his finances.
"Yeah, what about him?" Josh asked, standing next to my desk and leaning over my shoulder.
"Remember when you asked if I'd ever gotten a blowjob from a man? Well, he's sucked my cock," I revealed. "More than once. On quite a few occasions, actually. I'm thinking of texting him and inviting him over. I'm so fucking horny today," I admitted, squeezing my bulge through my thin slacks. This summer heat wasn't helping me cool off either.
Josh seemed interested in my history with the Colonel and he asked for more details. So I shared the saga with my son, going all the way back to when I was 18 and my dick was just getting acquainted with the insides of a man's throat for the first time. My son seemed equally impressed and surprised by the story.
"Wow. I never knew that about Great-Grandpa Ron," Josh exclaimed. "For some reason I always assume old people had really boring sex lives back in the day; but some of you were certified freaks."
"Some of us still are," I corrected him with a smirk. My right hand was still on my crotch, rubbing my cock which was now rock-hard after sharing that story with my son.
"Hey, Dad… Instead of texting the Colonel, what do you say we take care of this ourselves?" Josh suggested. He pointed down at his own crotch, where his dick looked every bit as hard as mine was.
"Alright, then," I agreed. "Should we go for some visual stimulation. Not that we need it, haha."
I got rid of the spreadsheets on the computer screen and opened up a porn site. Unwilling to browse, I just clicked on the top video of the day. As it turned out, it was a threesome between two men and a woman, who sucked one of the men's dicks while the other guy ate her pussy.
"This alright?" I asked my son, unzipping and pulling out my boner. Since I was already hard, it took some maneuvering to get it out of my underwear and through my fly.
"You mean the movie? Sure," Josh replied, not too interested either way. Standing by my desk chair, he pulled down his shorts so they were resting below his asscheeks and his smooth ball sack. His rock-hard dick was now just a few inches from my nose.
"Damn, Son. I never realized just how similar our cocks were," I noted. It was extra unusual, since Josh and I didn't look alike very much other than in the johnson department.
"Yeah, I've always been impressed by that," my son said, looking down at his cock and then scanning my own.
"So you've noticed it?" I asked, gathering some precum from my yawning piss slit and using it to start stroking up and down my shaft.
"Yeah. Remember when I was like 14 or 15 and walked in on you jerking off? It's stuck in my mind since then."
"Huh," I nodded. "So even at that age you looked like me? Good boy," I patted my boy's bare ass cheek the way a coach pats his players after a good game (at least they did in my day).
The video had us both leaking more and more precum, eliminating the need for lube, which I sometimes used while jerking off. We were going all natural and organic, California style! As hot as the actress on screen was, I couldn't help but turn to my right and focus on my son's prick more than anything else. At my age, I was developing wrinkles and freckles all over, including my dick. Josh's rod looked like a younger, photoshopped version of mine, free of graying hairs and darkening veins.
Feeling attracted to it like it was a powerful artifact from my past, I raised my right hand and wrapped it around my son's bone. "You don't mind, do ya?" I asked casually.
"Go for it," Josh gave me his blessing. I jerked myself off with my left hand while simultaneously providing pleasure to this strapping young man's cock with my right. This strapping young man who just so happened to be my firstborn son.
"Ever seen Callum's prick?" I asked my son suddenly.
"Yes," he nodded, letting out a little moan as I gripped his member tighter.
"Does he take after us?" I continued curiously asking questions.
"Not 100%, no. But he might still grow," Josh said politely.
"Let's hope so. He could use a big old rod like his dad's. Bet all the boys would be all over him," I noted, since I was aware that my grandson was gay.
"I think Callum's mostly concerned with attracting men with his ass, if you know what I mean," my son filled me in.
"Oh, is that so?" I wasn't surprised to hear my grandson was a bottom. Now that I thought about it, it should've been my first guess.
I continued stroking both mine and my son's cocks, closing my eyes and realizing that they felt identical in my hand. Blind, I couldn't tell which was which. I switched up my hands a few times, transferring intergenerational precum from one cock to the other.
"Is this more fun than what you did with the Colonel?" Josh asked.
"Well, this is fun. But the Colonel sucks my cock, so that can't really compare."
Suddenly, I felt my son's dick pull out of my hand. With my eyes still closed, I was surprised when two seconds later I felt a pair of lips around my sensitive cockhead. I opened my eyes and realized my son was now kneeling on the floor with my dick in his mouth, sucking off my precum and teasing me with his tongue.
"Fuck, Son!" I moaned out loud. Josh had jerked me off last week, but I didn't expect to have him sucking my cock as well!
From the job he was doing, I could tell my son wasn't used to this. He wasn't horrible, but he was clearly no experienced cocksucker. I wondered if he'd ever done this to anyone, or if I got to do the honors and pop his throat cherry.
"Cover your teeth, boy," I instructed him, placing my hands on Josh's head and gently guiding it up and down my member. I lifted my hips off the chair and started to gently fuck my son's mouth, careful not to go in too deep too soon.
With the tip of my dick, I felt Josh's throat start to relax. Little by little, I ventured deeper inside of it, making my son gag a couple of times. But Josh was a fighter if there ever was one! There was no bitching and moaning, like my wife sometimes did. It was clear my boy was eager to learn.
Gushing precum all over Josh's palate, my cock slid farther down his mouth until I was finally hitting the back of his throat. My son's lips were now at the hilt of my baby-maker, his nose buried in my bushy pubes, taking in his father's musk. With my hands still on Josh's head, I aggressively pushed him down just one time, causing him to choke. I was teasing him, but also exploring the depth of his oral cavity.
Most of the men who'd sucked my dick throughout the years were openly gay or bisexual men. Some, however, were straight, I was certain of it! Whether married or single, they simply wanted to experiment. For many of them, it was their first (but not necessarily last) time. In a city like San Francisco, the stigma around this was especially low. Now, Josh reminded me of all of those straight men. Maybe this was just a moment of experimentation for him, or maybe an opportunity to bond with his old man. God knows I won't be around forever. Why not make one more unforgettable memory together?
In order to better hump my son's mouth, I got up off the chair. Standing up and thrusting my hips with gusto, I was now properly fucking my son's throat! For a beginner, Josh's deepthroating skills were beyond impressive. Going into dad mode, I felt a burst of pride that my kids excelled at whatever they set their sights on.
When I looked down, I saw my son's wonderfully full set of hair. My fat fingers were combing through it as Josh's head bobbed up and down, taking me deep in his throat and then allowing me to pull out so that only my mushroom head was inside of him, before slamming back in. Back and forth, up and down, we played this game until the amount of precum I was oozing resembled a waterfall sliding down my son's throat. I wondered… if he'd swallow my babies when I finally cum…
"Fuck, Son, this is intense!" I said loudly, referring both to the physical as well as the emotional effects of this blowjob.
"Mhm," Josh nodded with his mouth full. Even with a mouthful of cock, he still looked like a strong, macho man. My boy.
"Fuck, boy, you're doing a great job. I'm getting close to the edge," I admitted, fully aware I couldn't hold it in much longer. In case Josh wanted to pull out, this was the time.
My son, however, seemed to have no such intention. Instead, he only went harder and faster on my dick, sucking it like a goddamn pro! I let go of his head, allowing him to operate by himself. Just like when I was teaching him how to ride a bike or drive a car: at first he needed my directions, but then he took over control. He was a quick learner, and I was a proud daddy.
"Fuck, fuck," I panted as my son's mouth went to town on my engorged cock. It was all too much. "I'm gonna cum. I'm gonna cum!"
The words only served to get Josh to suck even more intensely. A couple of seconds later, my ball sack contracted and started emptying its contents. My baby batter slid down my straight son's throat as I shouted and hollered in unbridled pleasure. Maybe it was wiser to keep it down, but it was a large house, and everyone knew not to come into my office without knocking.
… Which is precisely why I was so surprised to look up and see the door open. Caught unaware, I saw my grandson Callum's head peeking in, getting an eyeful of his daddy swallowing my jizz. I was mid-orgasm and unable to stop. Josh's eyes were closed so he couldn't see his son, but Callum and I made intense eye contact just as I fed my semen to his hungry dad. Fuck!
Without saying a word, Callum kept the door open for several seconds before closing it and disappearing behind it. Just as I was done unloading, Josh opened his eyes, looked up at me, and started stroking his cock until he busted his nut all over the hardwood floor in my office. As he jacked to completion, my son kept my prick in his mouth, nursing on the last driblets of cum I had for him.