Let Me Help You Cum
This year, I would get to celebrate Thanksgiving on three different occasions. On Thanksgiving Day, I was to spend the holiday back in Ohio with my ex-wife and our kids. The weekend right after the holiday, I was already invited to David and Sven's apartment, where we would all have a large dinner with our sons… like a family.
The thought left me quite emotional. After almost half a year in Boston, the Hillbeckers truly considered me a part of their family. It meant that much more since my own family was officially dissolved now that my divorce was final. I had a long way to go before establishing myself in Boston, but at least now it felt like home. Of course, the upcoming birth of Eric and Will's child – my first grandchild – was what filled me with excitement and anticipation more than anything else.
But before all of that, I was also invited to celebrate "Friendsgiving" with my three housemates. Living with three college students took some getting used to at first, especially since I never went to college myself. However, in a way, it turned out to be exactly what I'd needed. The three boys were all very friendly. After a long day's work, it felt good to come back home and have someone to have a beer with. They even taught me how to play video games! It was nice to be amongst people who were younger, more optimistic, less jaded by life. None of them were 21 yet so they called me their "Beer Daddy," since I was in charge of procuring the booze for everyone. It made me smile, and I wore the title with pride.
The celebration at our house took place the Saturday before Thanksgiving, before everyone left Boston to go back home for the holiday. The boys invited around 20 people over, a few of which I'd met already, including two of their girlfriends. Our final housemate was gay, as were most of his friends whom he'd invited. What struck me most was how cool this generation of kids was around each other whether gay or straight or anything else. When I was their age, my group of straight guy friends sure as hell were homophobic; and even though I wasn't the worst offender of the bunch, I'd certainly said and done things I wasn't proud of either.
The Friendsgiving party went well and ended around 9 PM, due to the fact that two of my housemates had early flights the next day. This worked out great for me because I had to go to work, even though it was a Sunday. The following morning, I woke up and went down to the kitchen to see my two housemates and their suitcases, waiting for their taxi to the airport to arrive. They were both fully dressed and I felt a bit awkward strutting around in front of them in my boxer briefs, but this wasn't the first time this had happened. (Indeed, when I first moved in and the weather was warmer, the boys seemed to wear hardly anything but their underwear around the house, a habit which had stuck to me as well.)
We kept our voices down since our last housemate Troy was still asleep. When the cab arrived, I gave them a hug to say goodbye and I went back upstairs to take a shower. That day, there was hardly any work to do at the office. That was often the case on a Sunday but now, probably due to the upcoming holiday, it was extra slow. Around 1 o'clock, I was given permission to go home and – feeling like a child let go from school early – I returned to the house.
I kept the noise down when entering, unsure if Troy was still asleep or not. However, as soon as I was in the house I realized he was most definitely awake: he was shouting at the top of his lungs. At first I thought he might be in some sort of trouble but I quickly realized… those were sex noises. Troy was having sex up in his room! With the door open, by the sounds of it. He expected me to be at work all day; he thought he had the house to himself.
I climbed up the stairs and went to my room, which was a couple of doors down from Troy's. I was certain he and whoever he was in bed with didn't hear me over all of the noise they were making. I was just about to shut my bedroom door when I stopped in my tracks with what I heard.
"Fuck me, Daddy!" Troy moaned loudly. It made me pause for a second for some reason. Next, a deeper voice grunted, "Fuck yeah. Take that, boy!" This voice clearly belonged to an older man, maybe even older than me by the sound of it.
During yesterday's Friendsgiving celebration, a couple of Troy's friends had cracked jokes about him being into "older guys," but I assumed that meant guys who were 25 or even 30… not somebody older than me! Troy was our youngest housemate, barely 19 himself. Suddenly I felt a weird fatherly instinct to go to his room and break up what was happening, to defend him somehow. But he didn't need defending; he was asking for this. "Fuck me!" he kept moaning over and over again.
I reached down between my legs to adjust myself, when I realized I was popping a boner in my uncomfortably tight slacks. I hadn't had sex since before my separation from my wife, and these days it didn't take much to get me hard. As I adjusted my penis I felt it growing harder in my pants. I needed to change out of my suit anyway; I took my shoes off, untied my tie and unbuttoned my shirt and tossed them aside. Finally, I pulled down my slacks and looked at a hard cock filling out the pouch of my underwear.
After separating from my ex, I looked up articles on "how to get back into dating in my 50s." A piece of advice on one of the lists was "Invest in some good underwear (yes, gents, this applies to you too)." Upon reading that, I'd gone to a department store and with some help from a very attentive gay male employee I'd revamped my entire underwear drawer. The pale-blue boxer briefs that I was currently wearing were soft and extremely comfortable, even though they were also very snug and pretty much outlined every detail on my tool, especially in its current aroused state.
Moans and grunts continued to echo from Troy's room. Then unexpectedly, a memory that I'd forgotten for over 40 years suddenly came back to me.
I was in a situation just like this once before… when I was little… at my parents' house. They were very private people who never showed any PDA except the occasional peck on the lips on a special occasion, and they certainly didn't have sex with the bedroom door open. But one time they must've overlooked it. One time, I was in my room, just like this, when I heard sex noises coming from the main bedroom. Feeling curious, I stealthily walked up to their room and took a peek through the door that was cracked open just a few inches. I didn't even know what sex was back then, and that's how I learned: by watching my dad fucking my mother missionary-style in their bed, lying on top of her so I mostly got a view of his hairy ass and ball sack thrusting up and down. I don't remember touching myself or anything like that. I knew what I was doing was "forbidden," so I only watched for a couple of minutes then ran off to my room, blocking it out of my memory until this day.
And now, feeling equally curious, I left my room and headed to Troy's bedroom. I walked down the hallway slowly and quietly, just like the child that I once was. I had no idea what I was doing, I had no plan. Before I knew it, I'd reached Troy's door which stood half-open, giving me a view of his bed where he lay on his back, getting his ass nailed by the man on top of him. I was right: the man looked to be my age or maybe a couple of years older. He might've been overweight but he was clearly strong: he was managing to hold himself up in a pushup position while thrusting his hips back and forth, splitting my housemate's asshole in two.
I stood in the doorway, my heart thumping, my dick pulsating in my boxer briefs, leaking out precum that stuck to the material. I grabbed my crotch again, massaging it slowly while my housemate yelled out "Fuck that ass, Daddy! Fuck my ass!" That's when I realized… that Troy kind of looked like my son Will. Their hairstyles were different, and Troy was a few years younger, but other than that the similarities were striking. At that very moment, I felt an even larger spurt of precum shooting out of my piss slit, seeping through the cotton material and sticking to my fingers.
"You like watching?" the strange, older man's voice suddenly said. I freaked out when I realized he was talking to me. His back was still turned to me, but then I spotted a mirror on the other side of the room. The man could see me standing in the doorway, playing with my cock while spying on them. I was acting like a perv, but it didn't seem to disturb him. His next words were, "Wanna join?"
"N– No," I stuttered. I wanted to add "I'm not gay," but I figured there's no need for that.
Troy looked up and saw me looking, and he just smiled at me before letting his head fall back onto the pillow. "Fuck yeah, fuck me right in front of him!" he commanded his buddy, who was all too happy to obey and started going even harder on my teenage housemate's ass.
There was no hiding anymore. I pulled my boner out of my underwear, gripping it firmly in my hand. Eager to get a closer view, I took two or three steps into the room. Then, I watched the gay couple fuck for ten minutes while I masturbated and enjoyed the show. I'd never seen two men fucking, not even in porn! I'd also never fucked a woman up the ass, so this was all fairly foreign to me. Despite that (or maybe, because of it) it felt extra hot to be standing here, witnessing this scene.
As Troy's moans got louder and louder, I got the impression he was close to cumming. I came in closer and looked between his legs to see him clutching his own hard dick with his left hand. I was surprised how big it was – bigger than mine at any rate! It was made even more obvious by the fact Troy's frame was significantly smaller. Just like… just like my son. Just then, I wondered if Will's tool was also bigger than my own. The thought pushed me to the very edge. Troy's right arm fell off the bed and I realized he was reaching toward me with his hand. He and I made eye contact and his eyes – so similar to Will's – seemed to say, "Let me help you cum."
Thinking with my prick rather than with my head, I stepped closer until I was a foot away from the bed. Troy's right hand wrapped itself around my boner, sending an incredible thrill all over my body! He was the first other person to touch my dick in over a year. Man or woman, it was irrelevant at this point: it felt AMAZING!
My son's doppelgänger gripped my tool as firmly as his soft fingers could muster and I began to thrust my hips, fucking his hand. The teen did an excellent job focusing on three things at once: getting fucked, jerking himself off, and fisting my cock. He and I looked at each other's eyes and we knew just what was coming next.
"FUCK!" I shouted and let my balls explode all over my young housemate's chest. I was cumming and cumming like I'd never cum before, absolutely drenching the teen with my jizz.
"Holy shit!" the man fucking Troy said, impressed by my cumshot so much that he stopped thrusting for a moment. But just a couple of seconds later, he picked it back up, going faster than ever and soon letting out a loud "Fuuuuuck!!" himself. He was blowing his load, I could tell. I could clearly see that they were fucking bare, which meant the man was shooting his load straight in the teen's ass.
"AHH!" Troy moaned, joining us and nutting all over himself. Seeing that made me shoot out yet another huge wad of cum – whether it was my second load or just one long orgasm I couldn't even tell. I fucked the teen's hand until I couldn't take it anymore. My dick was raw, still glistening with cum and sweat as I took a step back from the bed. While catching my breath, I watched as the unknown man pulled his thick tool out of Troy, whose asshole gaped like a wide-open crater, a few dollops of spooge oozing out of it before Troy clenched it shut. Once again, I thought of Will and wondered who fucked whom in his relationship with Eric. Did Eric blow his loads inside my son's asshole, leaving it gaping and dripping with jizz just like Troy's?
"I… I'm gonna go take a shower," I said, unsure what else to say or do.
"Okay, Daddy," Troy smiled at me, lying in bed covered in both of our cum. He'd called me "Daddy" before, all of my housemates had done that playfully. But this time, it somehow felt different.