DENNIS:

    "You've had sex with lots of men, right?" I asked.

    Lying in bed next to me, Ross Crane – my math teacher and fuck buddy – let out a laugh.

    "Uh, sure," he said, reaching for the water bottle on the nightstand and taking a sip. Then, he offered some to me. As the cool water slid down my throat, I simultaneously felt some of Crane's cum oozing out of my ass and onto his expensive bedsheets. He'd deposited a load in me a few minutes ago and as much as I tried to maintain possession of it, my loose hole let some of it leak out.

    "And did many of those guys have wives, or girlfriends, or ex-girlfriends or whatever?" I asked him next.

    "Yeah, sure. Why do you ask?" he said. 

    "Well, up until recently, I thought vast majority of men were straight, and only a small number were gay or bi or whatever, and those were the ones who hooked up with other men. But now I'm wondering if maybe most men have fooled around with another guy, you know?"

    "Listen," Crane said as he sat up, "I'm not gonna tell you most men have fucked or been fucked by another guy cuz I don't think that's true. But if you include everything: mutual maturation or getting a helping hand… I think you'd be surprised by how many quote-unquote straight men have experimented. Why, what made you think about all this?"

    "My grandfather," I confessed to Crane. "I never thought of him as anything but straight. Then I find out he was actually younger than me the first time he sucked a dick."

    "Ha. Just goes to prove: you never really know what people do behind closed doors," my teacher chuckled.

    "Oh there were no doors, this happened out in the middle of the woods," I laughed. "I'm surprised they had cruising grounds back in the day."

    "Are you kidding me? That was the heyday of cruising. Before the internet, that's how people met up," Crane said.

    "Would you take me to a cruising ground, and watch other men fuck me?" I asked flirtily, leaning against Crane's bare chest and playing with one of his nipples.

    "Oh, you'd love that, wouldn't you, you little slut?" he grinned. "I'll consider it. But for now, the only place I'm taking you is your grandfather's house."

    "Really? You wanna drive me there?" I asked. As per usual, I'd taken the bus to get to Crane's house, and he'd never driven me home before.

    "Well, now that Principal Osborne knows that we're fucking, there's no need to hide," Crane said. "Besides, I'm driving that way to visit a friend. C'mon."

    Before getting dressed, I used a cum rag to wipe the jizz off my ass. Luckily, most of Crane's load was still safely inside my hole. Crane drove me past the bus stop where I'd chained my bike (I'd have to pick it up some other day) and we soon arrived in front of Grandpa's house, where I gave Mr. Crane a kiss and said goodbye to him.

    When I entered, I went into the kitchen to get a glass of water and found my grandfather at the table doing paperwork of some kind. From where he was sitting, I knew he'd had a full view of the front of the house and would have seen me getting out of Crane's car. We greeted one another and Grandpa just looked at me curiously while I took a drink.

    "Was that Crane who just dropped you off?" Grandpa asked finally. There wasn't any judgement or concern in his tone.

    "Yeah," I said, giving him a smile. Crane was right, there was no need to hide anything now. Even though Grandpa and I hadn't spoken a word to one another about what happened the day of the Super Bowl a couple weeks ago, he also didn't act like he was freaked out by it. Things just seemed... normal (well, our version of normal, at least). Finn had been over a few times over the past two weeks, and he and I spent hours up in my room having sex. Once, I realized afterward that we hadn't fully closed the door. My grandpa could probably hear everything we were doing, and he was obviously fine with it.

    "So you and Crane...?" he asked, and then he paused. I had the impression he was waiting for me to finish the sentence.

    "Had sex at his house, yes," I added. Smiling again and feeling a sense of confidence, I walked into the living room and waited to see if Grandpa would follow me.

    "Did you have fun?" he asked a moment later as he walked in. I'd taken a seat in one of the chairs and he sat down on the couch, at the end closest to me. Our knees were almost touching.

    "Yeah, of course," I replied. "It's always fun." I found myself wondering, as I'd done often these past weeks, about what my grandfather's kinks and fantasies might be. Now that I knew he wasn't just some boring, celibate principal like I always thought, it was kinda fun imagining all of the stuff Gramps might do in his private time. "Did you do anything fun at home?" I asked, letting a teasing tone slip into my voice.

    "No, not really," Grandpa said, sounding slightly disappointed. I was still feeling horny even after the long fuck session with Crane. All of a sudden, I remembered what it was like to suck my grandfather's cock that one time. It almost seemed like a dream, and sometimes it was hard to believe the incestuous blowjob had actually happened. I wondered if anything like it would ever happen again, if Grandpa and I found ourselves in the right situation. Which is what this felt like.

    "How about… we do something fun as well, then," I suggested. I let that sit and just watched my grandfather's reaction. I felt a rush while he pondered the idea, and we both knew how this moment right now was pivotal for our relationship.

    "I'd like that a lot, Dennis," he finally said with a kind smile.​​

    Before he had a chance to change his mind, I slid off the chair and onto my knees, positioning myself between Grandpa's spread legs. It was wild to actually see his cock swelling up in his pants, pushing the fabric out as it grew. Mine had shot up fast when he agreed to play around, fully hard before my knees had even hit the floor.

    My hands quickly undid his pants and together we slid them down and off of his legs. I massaged his shaft through his underwear for a moment, feeling the warmth of it through the cotton. Then, we had those removed in a flash, and Grandpa's cock jutted into the air right in front of my face. I was struck again at what a great piece of meat my grandfather had. Long but not intimidatingly so; thick but not too thick.

    It turned me on that I was getting enough experience to know how deep in my throat I could take a cock on the first plunge based on its size. Grandpa's would slide down just perfectly. I grabbed his shaft and brought the head to my lips, taking some time to polish the sensitive knob and make him moan softly. He was already leaking precum and I noticed that he tasted different from Crane, and also different from the triplets (who, unsurprisingly, all tasted the same). I heard myself moaning softly too, as I suckled the head in my mouth to get every salty drop.

    When I suddenly leaned forward and slid Grandpa's entire dick down my throat, he yelped in delighted surprise. I pushed my nose into his pubes and moaned again when I felt his hands touch my scalp, gently pushing his cock a little deeper. I would have been happy to stay like that for a while, but I also wanted to treat my grandfather to a full range of oral services.

    Over the next ten minutes I made sure that my tongue touched every millimeter of his cock and balls. Now and then I'd deepthroat him briefly, then return to worshipping his dick with my lips, tongue and hands. Grandpa told me how good it felt, both with grunts and words, and when he moaned "I love you, Dennis" I felt my face flush while I licked his nuts. I knew right then that I wanted him to fuck me tonight. Not just tonight, but right now.

    He seemed surprised when I stood up, and it seemed like he might be about to stand up himself. Before he could do that, I moved forward and straddled him with my knees on the couch. I lowered myself down and felt his cock side up my asscrack, the head coming to rest right at the small of my back. I reached behind myself and pressed his shaft against my skin, stroking him a little bit as I did that. My cock was sticking straight out in front of me, dripping precum onto my grandfather's T-shirt, which had the school's mascot on it.

    "Oh, shit... Are you going to...?" Grandpa said, taking in a quick breath as my hand moved up and down his slicked-up shaft. I didn't let him finish the question. Moving fast, I raised myself up again and pushed his cock toward him slightly, until I felt his swollen knob brush against my recently-bred hole. I wondered if Grandpa would feel Crane's load inside of me. I knew the jizz inside my ass would provide enough lubrication to let me slide a good amount of Grandpa's cock inside me at once.

    I lowered myself down again, holding the base of his cock as the first few inches pushed up into me. My grandfather's words dissolved into moans and utterances of "oh my God," and his hands went to my waist, gripping me tightly right above the hips. I paused for a moment to let my ass get used to his cock before I took the rest inside me. Crane loved to just shove all the way in on the first push, and that was hot but could be pretty intense. I found that I liked to enjoy going a little slower, savoring the sensation of being penetrated deeper and deeper.

    When I started to push down again and felt Grandpa gently pulling me down as well, my cock throbbed and got even harder. It was very pleasing to feel my grandfather really getting into this right away. When I felt my ass come to rest on his thighs, we both let out a long breath. I looked him in the eyes and then I felt his arms move up to pull my upper body toward his. He embraced me tightly, even pressing his chin into my shoulder. If his cock hadn't been balls-deep in my ass, it would have been just like when I was a boy sitting in his lap and hugging him.

    "You're so... loose and open. But it feels tight at the same time," he said as I moved to be more upright again. I smiled wide, feeling proud that my ass was trained so well. I had Crane to thank for that of course, though the triplets certainly did their share. Wyatt had recently whispered to me that he was starting to prefer my hole to Mason's, and hearing Grandpa's compliment gave me the same rush. I felt pretty sure that my ass was the first one he'd ever had.

    With so much emotion and desire pent up inside me, I was overcome by it all and began to ride my grandfather hard. I wanted this to be the most memorable sex of his life. His hands explored my body as I fucked myself up and down on his cock, bracing myself with my hands on his shoulders. He didn't last long against that all-out assault, and when he shouted that he was about to cum, I realized I was close as well. Slowing down just enough to let his cockhead press against that magic spot inside me, I felt myself start to shoot at almost the same moment that Grandpa's dick began twitching and pulsing in my ass. I pushed down hard one last time, wanting his family seed as deep in me as possible. We were both moaning loud and I could hear it echoing through the house.

    As the waves of pleasure started to subside, a feeling of exhaustion came over me. I slowly lowered my upper body down until my chest rested against Grandpa's. I felt my load, which had blasted across the front of his school T-shirt, press warmly into me. I nestled my head into my grandfather's shoulder and relaxed into another embrace. He turned his head toward mine and I felt a gentle kiss right behind my ear. We stayed like that for a while and enjoyed the sensation of his cock slowly softening inside me.

    "I love you, Grandpa," I whispered.​​