This story was available to  Gold Supporters  in January 2021. It takes place after My Boyfriend and My Two Dads, Chapter 46: "Father-Son Striptease"

 

JUNIOR:

  From what I knew about my father's past, he used to be quite the ladies' man; the kind that most girls fought over in high school and college. Which is why it came as such as surprise to most people when he came out as gay three years after divorcing my mom. I was twelve by that point, an age where I knew what was going on but I didn't care too much about it.

    Apparently, coming out came with some unexpected side effects. Dad was well into his 30s by then, already losing some of his hair and growing a gut. He'd decided that if he was going to attract a man, he should get back in shape. He started going to the gym as well as a bunch of fitness classes, where he met new people (most of who were probably gay men) to socialize with. 

    Meanwhile, I was preoccupied with my own early-teens life. I saw dad every other weekend, and stayed with him in his new apartment in Downtown Boston. The place was MUCH smaller than our house in the suburbs, at times it felt too small even for just the two of us. Still, I was thrilled to be in the city, and the weekends I spent at Dad's were some of my fondest memories from when I was in middle school.

    Dad's personality kind of started to change as well. Maybe it was the fact that he was now a bachelor, or maybe it was just that I was getting older and he felt more comfortable making rude jokes around me. Off-handed comments about stuff like sex or drinking were no longer taboo. I liked this new side of him. Since I didn't have any friends downtown, he and I spent most of the time together when I came to stay over. In a way, the divorce made us closer than we'd ever been.

    I still remember when my father started walking around in his underwear in front of me. He never used to do it when I was little, but now that he was working out I guess he grew more comfortable in his body. I was 13 or 14, and impressed by how... manly he looked. Of course, at that age I was obsessed with "being a man" as soon as possible myself, and I hoped I would take after my father.

    Dad also made the switch from boxers to briefs right about that time. I remember feeling mesmerized by his bulge, which was pretty much always on display whenever we were at his apartment now. I was happy with my size, but he was clearly bigger! Once, while I was having breakfast, he stood on a chair right in front of me to change the light hanging over the dining room table. I was pretty much head-on with his crotch, and since he couldn't see me, I used that time to analyze the outline of his cock, including the helmet head which was fully distinguishable. 

    I often heard my father watching porn in his room during those years. Even more often, I did the same. Eventually we started to joke about it, since there was no disguising it anymore. I was mostly into straight porn, but every now and then I ventured into the gay categories, thinking "Is this what Dad is into?" I wasn't turned off by most of it. With time, I started to jerk off while watching those videos as well.

    When I started having sex with girls at 16, it was a no brainer for me to go to my dad and tell him about it. By that time, Dad was in a serious relationship with a guy named Angelo, and the two of them were making plans to get married. With Angelo moving into the apartment, there was even less space for all of us. From that point on, almost every single night that I stayed over, I fell asleep to the sound of the two of them fucking in the next room, sometimes jerking myself off to sleep as I listened.

    I walked in on Dad and Angelo fucking more than once as well, usually when they were doing it in the kitchen or living room. They both seemed to have quite an exhibitionist streak to them (even though I didn't even know what "exhibitionist" meant at the time). I even caught them with other guys occasionally; this one time, I could swear the boy they were spit-roasting was hardly older than me.

    As I graduated high school and started BU, I was still mostly into girls. I was a football player, and there were a ton of hot jocks on my football team, but I always looked at them like buddies and bros, even though I admired how sexy most of them were. I had no big interest in guys my age. But for some reason... I had an eye for daddies.

    I have no idea how much my attraction for older men had to do with my father. Right before I graduated high school, I jerked off my football coach a couple of times, which was my first hands-on experience with another guy. Over the next year, I downloaded Grindr and hooked up with several men who liked to get fucked. I didn't check the app too often, but whenever I did I had hundreds of messages, which wasn't too bad for my ego as well.

    After a year of living in the dorms, I moved into an apartment with a couple of other kids from school. At our housewarming party I met David, a man who coincidentally happened to live across the street from my dad. I fucked David in my room, in front of his very own son, who was a few years older than me. After that night, my relationship with my own father would never be the same either.

    I kept thinking about David and Eric after the party. Dad and I were "open" in front of each other, but I'd never watched another man fuck him the way Eric did his dad. It confused and turned me on at the same time. And it made me wonder just how far I could push things with my own father.

    Turns out, I didn't need to push anything; it was Eric himself who'd be doing the pushing for me. Shortly after the housewarming, he showed up at my father's place and asked us both to fuck him. I was dumbfounded! I thought it was some kind of prank at first. Not to mention the fact my father had no idea that I was into men.

    Apparently, there was no need to mention that fact in the first place. Everything sort of happened, without a big coming-out moment. Dad came inside Eric's ass, then encouraged me to do the same right after him. It was WILD, fucking a warm ass right after it'd been fucked by my own father, his jizz serving as my lube.  

    "Give it to him, son!" Dad cheered me on until I bust my nut inside Eric's hole. Minutes later, our bottom was on his way back home, leaving me and Dad to talk about what happened.

    "I don't know about you, but I'm starving after that," Dad said, sitting next to me on the couch. We were both naked, our cocks still half-hard and glistening with cum. Mine had my own as well as Dad's all over it.

    "Let's go out and eat," Dad patted my thigh and started to get dressed. Fifteen minutes later, we were at a restaurant downstairs, biting into our sandwiches. "So, I take it this wasn't your first time with a dude?" my father asked casually while chewing his food.

    "No," I admitted. "It's been over a year."

    "Over a year of doing what?"

    "Fucking other men. Usually older. Eric was actually the first younger guy I've fucked."

    "Older men, huh? So you into daddies," my father smirked.

    "Guess so," I chuckled.

    "Ain't nothing wrong with that. Just be careful. And have fun."

    "Oh, I am. I'm having lots of fun," I grinned.

—

    A few weeks later, Dad and I got another shot to have some more fun together. Once again, it was facilitated by David's family. I was having lunch at the very same restaurant with Dad and Angelo when David walked in, this time with Eric's husband, Will.

    Dad was the one who suggested we all go up to the apartment after lunch. As soon as he said it, I had an idea where this might be going. Sure enough, we all ended up in my father's bedroom. It was David's birthday, and Dad and I gave him a lap dance, and stripped for everyone else in the room. This time, Dad and I were hands-on, rubbing each other's bulges and pulling down one another's underwear. It started off as a joke but it quickly progressed to something much, much hotter.

    Will turned out to be just as hot and mischievous as his husband. He offered his ass to me, while my father and Angelo worked on David from both ends. I came inside Will's ass shortly before my father blew his load inside David, all the while holding his hand on my shoulder. It filled me with a level of horniness – and love! – the kind of which I never thought I'd experience. 

    After Dad's neighbors left, the three of us lay in bed, cuddled up. Angelo praised my performance, before saying "I thought you were into older men, though?"

    "Mostly, but not exclusively," I replied. 

    "Cuz I know one older man who hasn't been fucked in a while..." Angelo suggested, looking at my dad.

    "What?" I asked, confused.

    "Who you calling 'older'?" my father objected, and started to play-wrestle with his husband in bed. It was funny that he objected to the word choice, but not to the suggestion itself.

    "You guys don't flip-flop?" I asked, curious to know more. I tried to make it sound as casual as possible.

    "Sometimes we do," Angelo replied, "but it's usually your dad fucking me. He's been grumpy about bottoming lately." Angelo smacked my dad's bare ass, and I realized just how nice Dad's ass was.

    "I've been saving it for a special occasion," Dad defended himself.

    "Well this is a pretty special day," Angelo once again made his insinuation, squeezing my dad's thick ass while talking. I looked up and made eye contact with Angelo, who asked me, "Do you feel like it?"

    "F–Feel like what?"

    "Fucking your dad. I'd love to watch you guys."

    I looked at my father, fully expecting him to object to all this, or to start laughing because this was all some sort of joke. I mean, it was one thing for him and me to fuck the same guy, or to fuck side-by-side... but for me to fuck him?! There's no way he'd go for it.

    Still, Dad just sort of shrugged, as if to say "Up to you." I couldn't believe this! Before I knew it, I was nodding my head and saying "Okay."

    "Go for it," Angelo grinned ear-to-ear and made himself comfortable on the bed, like a kid whose favorite program was about to start on TV. I lay on my back, with Dad on his stomach next to me. It started with a kiss, as he leaned closer and put his lips on mine, like he had many times in the past when I was little. But this time, instead of giving me a peck, he opened his lips and let my tongue enter his mouth, before returning the kiss and shoving his own tongue inside me.

    "Mmm," I moaned out in unexpected pleasure, closing my eyes and running my fingers through my father's thinning hair. Fuck, I loved this man!

    One of my favorite things about older men was how smooth and experienced they were. Dad ran his large hands down my muscular body, giving me goosebumps everywhere. He teased my nips with his fingertips gently, pinching them just as the pleasure started to heighten. He was an amazing kisser... probably the best I'd ever had.

    With all of this, it was no wonder that I was rock hard in no time. I reached down to my cock but Dad guided my hand away. 

    "Let me do that for you," he said, then went back to kissing me. He wrapped his right hand around my cock and squeezed firmly. He released the pressure, then squeezed again. He did this multiple times, barely stroking up and down, until I was leaking precum all over his hairy fingers. When he noticed how excited I was getting, he let go of my dick, making me whimper and beg for him to continue.

    "Shhh, give it some time," he reassured me. 

    "Daddy," I said for the first time since I was a little kid.

    "I'm here, baby. Daddy's here," he replied gently, and wrapped his fist around my cock again. This time, he stroked me up and down, driving me wild with every single move. He went on until I was close to the edge again. Then, as if he could read me better than anyone, he stopped at just the right time.

    I wasn't even aware of my father's husband in bed with us, watching the show and probably stroking his own cock. This was all about Dad and me. Wanting to return the favor, I put my hand around Dad's hard cock and started to jack him off. His dick was still sticky with cum which had come out of David's ass earlier. Up and down, I stroked the cock that made me, bringing my father to the edge and then letting go, making my dad laugh out loud.

    "You little fucker," he said, and lay back down on his stomach, poking his ass up in the air. "Go for it."

    This was it: I was about to fuck my dad's ass. I got in position, straddling him from behind. I squeezed both his asscheeks and started kneading them; they were too tempting to ignore. I played with them like a child playing with Play-Doh, while my erect cock bobbed right above the cleft of Dad's ass, which was covered in fine hair.

    Finally, I grabbed my cock in my right hand and used the fingers of my left to spread his cheeks open. Dad's hole winked at me, pulsing invitingly. I spit on my hand and rubbed his asshole with my fingertips, massaging his sphincter and occasionally slipping one or two fingers in. Every time I did so, my father arched his back and moaned, asking me to keep going.

    I felt proud I could provide him with this pleasure; but this was only the warm-up still. I continued to finger his hole more and more aggressively, using two, then three fingers. Finally, when it was opened up enough, I pressed my wet cockhead right against it and started to push.

    "ARGH!" Dad shouted out. It was true that he was tight – I could tell he didn't get fucked too often – but I knew he had it in him. If anyone was a fighter, it was my dad. I continued to push further, feeling his hole slowly relax around my cock. 

    "There we go," I encouraged him. He was doing an excellent job and I wanted him to know it.

    Two minutes later, and his hole felt completely relaxed and ready for fucking. Wanting to make sure, I asked, "How does that feel?"

    "Feels fucking amazing, son. Feels fucking amazing," Dad said in a voice I'd never quite heard from him. Turned on by it, I started to pound his ass faster, my hand on his broad muscular back. 

    "There you go, Daddy," I said as he arched his back, inviting me to go in deeper. I often called the men I fucked "Daddy"... this time, it was quite literal.

    We kept going like this for over half an hour. I went fast, then slow, then fast again, without ever taking my dick out completely. I came close to the edge many times, but always knew when to stop and slow down. Until, at last, I knew I couldn't hold it in anymore.

    "It's coming. It's coming. I'm cumming," I started to pant, piston-fucking my father without control.

    "Fucking blow your load, son. Fucking bust you nut," Dad cheered me on. He started to grunt, and I did too, and a few seconds later...

    "Ah. Fuck. FUCK! Aaaah, yes!" I was blowing my load inside my father's guts, filling his stomach with his own son's cum.

    "Attaboy. Attaboy!" he kept repeating like this was one of my football games. His right hand was reaching between his legs, and I could tell he was jerking himself off to completion as well. As we came at the same time, we roared loud enough for David to hear us all the way across the street.

    Even though it was my second of the day, this was my most intense orgasm to date! I didn't want to pull out of Dad's hole, and even after my cock started to go soft, I remained inside for a while, churning my own cum that was in there. Finally, I pulled out, and my dad turned around to lie on his back. Feeling powerless, I plopped down onto my dad's body, face-to-face, and he wrapped his arms around me. Then, he smiled before planting another passionate kiss on my lips.

    "Phew. Well, that was fun," Angelo chimed in, using a cum rag to clean up the load he had shot all over himself. "Good job, Junior."

    "Yes, well done. I'm proud of you, son," Dad said to me as the tips of our noses rubbed against each other.