KEITH:

    Even though my grandson Dennis and I were now closer than ever, there was still one secret I was keeping from him. Dennis continued to be unaware of the hidden camera in his room. On several occasions, I watched as Dennis entertained one, two, or all three of the triplets from next door. Whenever he wasn't having sex with them, my grandson could be found in my own bedroom, using his throat or ass to milk a load out of me. Sometimes, Dennis even fell asleep in my bed, cuddling with me all night. The winter was cold in Pennsylvania, and this was one good way to make it feel warmer.

    Of all of the hidden-camera sex shows I'd seen take place in Dennis's bedroom, one really caught my eye. It took place on a Wednesday evening. Wyatt and Finn were both in my grandson's room, and both brothers were trying to stick their dicks up Dennis's hole – at the same time! I'd seen some DP porn in the past, enough to be familiar with the term, but that always involved women. I winced at the thought of being able to take two hard cocks up the ass. From what I could see, Dennis seemed to be struggling with it as well. Finn and Wyatt tried several times, switching positions, but they weren't able to both penetrate my grandson at the same time. In the end, they settled for going one by one, and I jacked off as I watched Wyatt and then Finn dump their cum in Dennis's receptive asshole. 

    Three days later, I woke up on a cold Saturday morning to find coffee and breakfast ready and waiting for me on the kitchen table. "Oh wow," I said to my grandson, who was rinsing the frying pan he'd used to fry the eggs.

    "I made breakfast," he said with a proud smile.

    "I see that. What brought upon this development?" I asked, taking a sip of coffee.

    "I just thought I'd be helpful," Dennis said, taking a seat at the table across from me. "Hope you like it."

    "You're certainly… full of surprises," I said to my grandson. I was originally going to say "You're certainly different from when you first got here," but I didn't want to sound reproachful in any way.

    "Surprises galore," Dennis added with a smile. "I take after my grandpa."

    "You think I'm full of surprises?" I asked, chuckling. As a middle-aged high school principal, I was used to people thinking of me as square, predictable, and boring.

    "Are you kidding me?! The things you've told me about your past – I would've never guessed," said Dennis. "Not to mention everything we've done over the past couple of weeks. It's been so much fun."

    "Speaking of fun… Do you have anything fun planned for today?" I asked. I found myself hoping my grandson was free, in which case I was going to invite him up to my bedroom. 

    "Aha," Dennis nodded with a mouthful of eggs. "Mr. Crane is coming over."

    "Oh," I said, looking down at my plate.

    "You're okay with that, right? It's just easier for him to drive here than for me to go to his place every weekend," Dennis added casually. 

    "Yeah, yeah," I pretended to be fine, even though I was jealous another man would get to spend the day having sex with Dennis. Looking to change the subject, I told Dennis, "Your brother Ethan is coming over next weekend. You haven't seen him since you were little, so make sure not to make other plans. It'd be nice for you guys to spend some time together."

    "Oh, okay. I'll let Crane know I'm not available next weekend," said Dennis, who had probably been planning on meeting up with his math teacher next weekend as well. Since Dennis and Ethan grew up in different states they never had much of a relationship, even though they were half-brothers. I'd seen 20-year-old Ethan recently and knew that he'd aged into a very handsome young man. I couldn't help but wonder how Dennis would react when they met.

    A few hours later, Crane arrived at the house. I'd intended to be in my office when he arrived. We'd kept things absolutely professional at work since the Super Bowl. Not at all awkward but not any more familiar than before, either. Even if there wasn't any pretense about why he was visiting my house today, I'd have preferred to avoid any small talk before he went upstairs to shove his cock into my grandson's eager holes.

    But of course, I happened to be in the middle of making a cup of coffee in the kitchen when the knock at the door came. I assumed Dennis had heard it and would be coming down to admit his math teacher and fuck buddy. But when Crane knocked a second time, I sighed and walked to the entryway. I could faintly hear the sound of the shower running upstairs.

    "Good afternoon, Ross," I said with a polite smile.

    "Keith," he said, with a nod of his head. He stepped inside and I shut the door quickly to keep the house warm.

    "Uh... would you care for some coffee?" I asked, realizing that I had my own steaming mug in my hand. "Dennis is in the shower."

    "No thanks," he said curtly, removing his coat and placing it on one of the hooks near the door. "Though if you can make it an Irish coffee I might change my mind." He smiled and raised one eyebrow.

    I just chuckled and went to grab the Bailey's. We sat quietly at the table for a few minutes and chatted. Not about work, or about Dennis, or anything particularly interesting. But it was pleasant, all the same, and I was reminded that Crane was actually a pretty nice guy, even if he did have a questionable lack of boundaries with regard to fraternizing with students. But who was I to judge, at this point? I was fucking my daughter's son several nights a week, and jacking off while spying on him on the nights he wasn't in my bed.

    Soon, Dennis came bounding down the stairs; wet, squeaky clean and totally naked. His cock looked like it was half-hard, and he had a bright smile on his face. He glanced at Crane and seemed amused that we'd been sitting and having coffee together.

    "Hey," he said to the teacher.

    "Hey," Crane said in response.

    "Ready?" Dennis asked.

    "Yeah," the older man replied, and then knocked back the rest of his beverage and stood up.

    "Enjoy," I said as he left the kitchen, and then wondered why I had said anything at all.

    "We always do, don't we?" Dennis quipped, looking back with a smirk before he turned the corner.

    I went to my office and shut the door, then sat down to access the camera system as I'd been planning to since I'd learned Crane would be here today. Watching Dennis with any (or all) of the triplets was hot. But his sex with Crane was next level. They got rough and intense. Dennis would sometimes cry out, but he always had a smile on his face, so I'd learned not to worry, even when Crane had his hands around my grandson's throat.

    Today, I noticed Crane brought a small brown bottle with him, as he did on some past visits. I knew about poppers but I'd never taken any so I only vaguely understood the effect they had when inhaled. Now, I watched my grandson take a hit of poppers just as Crane shoved his entire cock into his ass, with a pleased expression on both of their faces. Soon, I could hear Dennis moaning through the walls as the teacher slid out and slammed back in repeatedly. My cock was hard before I even finished getting it out of my pants, and I was stroking in time with Crane's thrusts into Dennis, thinking about how nice my grandson's ass felt when I was doing the same thing to him.

    After a while, I noticed that one of Crane's hands was remaining near his cock, in between his body and my grandson's ass. The camera angle made it hard to see, but eventually I figured out that Crane was fingering Dennis as well as fucking him. That made my cock throb even harder, and reminded me of Wyatt and Finn trying desperately to fit into my grandson at the same time. "If only Crane had been there to help them stretch Dennis out more," I thought with a perverse laugh.

    Suddenly, Crane pulled back and Dennis got up from the bed, both of them still fully hard. They certainly weren't done yet, but I saw Dennis moving toward the bedroom door slowly while saying something. I saw Crane nod his head, and then I heard my grandson out in the hallway. I stopped stroking but my cock was still on full display when Dennis shocked me by bursting into my office. I quickly put the tablet down, thankful that Dennis wasn't able to see what I was looking at since I was facing the door. I'm sure he assumed I was just jerking off to some hot porn. Which was true, only my grandson had no clue that he was the star.

    "Grandpa, would you, uh... care to join us?" Dennis asked, one hand idly stroking his dripping cock in the doorway. He was breathing hard, still clearly winded from their fucking. I was genuinely shocked at my grandson's request.

    "Uh..." I stammered, still processing all of it. "Are you sure?"

    "Yeah," my grandson replied with a look of excitement on his face. "There's something I really wanna try out, and we need another guy for it."

    "Well... okay," I said, standing up and deciding to just step out of my pants since they were already around my ankles. I took a moment to pull off my shirt as well. I pondered what my grandson wanted to "try" as I stepped into the hallway, but by the time I was entering his bedroom and locked eyes with Crane, it hit me: Dennis wanted us both to fuck him at the same time, like he'd been trying to do with the neighbor boys.

    I was feeling a little daunted before Dennis even began to reveal his plan, and it took some concentration to feign surprise when my grandson confirmed what I suspected. He looked giddy with excitement, while Crane looked very pleased with himself.

    "Are you sure you can handle this?" I asked. "Have you ever tried this before?" The concern in my voice was real, but I knew all of us noticed that I was just as hard as Crane and Dennis while we discussed the plan to DP my teenage grandson.

    "Not successfully," Dennis admitted, "but Mr Crane says he's helped plenty of bottoms take two cocks for the first time." The older man just nodded when I glanced at him, still looking pleased but maybe also a little impatient. I agreed to let Crane take the lead, and he set about getting us into position.

    I sat at the edge of the bed with pillows behind me so I wasn't lying totally flat. Dennis straddled me and sat on my cock, facing away from me and looking at Crane. The other man approached and stood between our spread legs, then put his hand on Dennis's chest and pushed him backward slowly. As my grandson's back pressed against my chest, I instinctively wrapped my arms around him, keeping him steady while he brought his knees up. Crane looked down salaciously, and I knew he was enjoying the sight of a grandfather's cock fully embedded in his grandson's ass.

    Crane handed the bottle of poppers to Dennis, who chose to clutch it in his hand for the moment. My cock throbbed inside its warm resting place as I felt Crane's dickhead push against my balls and slide up to the base of my shaft. He nudged it forward, first gently and then more forcefully, pushing on the spot where my grandson's sphincter was stretched tightly around my dick.

    "Do it," Crane said, and for a moment I wasn't sure what he was talking about or which one of us he was talking to. But then Dennis brought the small brown bottle close to his face and unscrewed the cap. As he brought the bottle to his nose, I caught a whiff of something that reminded me of the chemistry classroom. Dennis took a huff in each nostril and then hastily closed the bottle. A second later, I felt the amazing sensation of my grandson relaxing back into my chest, prompting me to squeeze him again with my arms. He sighed out a deep moan, and then I felt the tightness of his insides relax around my cock.

    Crane seized the moment and I felt him push hard with his dick pressed down against my own. Dennis's hole relaxed even more, and then suddenly the tightness was back, much more than before. A good portion of Crane's cock was now inside Dennis along with mine. My grandson and I both gasped, though his turned into a long moan.

    "Oh my God..." He said slowly, "It's... it might be too much... fuck."

    "You can take it," Crane said sternly, and I could tell he was itching to shove the rest in and get balls-deep like I was. Dennis whimpered softly and I sensed apprehension in him. His head was resting back on my chest, tucked into my shoulder. I turned and found that my mouth was right at his ear, and I kissed him softly there.

    "You're doing so good, son," I whispered to him. "I'm so proud of my boy. I know you can do it." Dennis relaxed a little bit and let out a longer sigh. The intense clenching around our cocks let up a little. "Do you need more?" I asked Dennis, tapping the brown bottle clutched in his hand. 

    "Mhm," he replied quietly. Remembering how he had done it, I opened up the poppers and held the small bottle to one of his nostrils, using a finger to close the other one. He inhaled, and we did the other side quickly. We made eye contact briefly as I replaced the cap, and I heard my grandson whisper "thank you" before he closed his eyes and lost himself to whatever feelings were rushing over him.

    As soon as there was a little less pressure, Crane pushed the rest of the way in. It was intense, feeling his cockhead rubbing against my own in the tight space. I understood why this was something men liked to attempt. The level of intimacy was unlike anything else I'd experienced. I felt deeply connected to both Dennis and Crane right at this moment.

    The other man slowly started pulling his cock out a little and then back in, fucking Dennis's stretched hole gently. Having our cocks rub together like that felt amazing for me, and I reflexively started making similar motions to keep that friction going. I wasn't able to move as much or as firmly as Crane, but after a minute or so we got into a rhythm where he'd push in while I pulled out, and vice versa.

    The effect on Dennis was absolutely wild to witness. He squirmed a little though he remained relaxed for the most part, letting us penetrate him. My grandson's moaning and whimpering was loud and continuous. At moments it sounded like he was in pain, though I understood that it was a number of sensations mixed together. His hard-on wobbled in front of him, pointing up at the ceiling and oozing a steady stream of precum that ran down his shaft. It was almost as if the added pressure from inside was squeezing the fluid out of him.

    When Crane paused for a moment and then matched my rhythm, we were both pushing in together and things got even more intense for all of us. With both cocks in him all the way, Dennis seemed almost out of breath. And then, when we both pulled back, it felt like he was trying to slide lower down to keep us inside him. We found a new rhythm where my grandson was matching us and fucking himself on our cocks.

    Suddenly, Dennis cried out and I watched his erection turn into a fountain, spraying his teen cum in almost every direction. Much of it landed on his own torso and stomach but I know both Crane and I got splashed. With every spurt of his dick, Dennis's hole clenched our cocks and pushing deeper became more of a struggle, though Crane was not deterred by the added pressure. When he started breathing fast, I figured he was close, and I felt myself nearing climax as well. The way Dennis's insides twitched and massaged my shaft while he was cumming always did me in, and this time feeling Crane's cock up against mine made it even hotter.

    I'm not sure who started cumming first, but as I experienced the rush I also felt the space inside my grandson fill up fast with both of our loads. Everything was much warmer and more slippery, and a few seconds later my nuts were wet with jizz that seeped out around our throbbing cocks. Crane and I had filled my grandson to his limits, clearly.

    It took a while for all of us to catch our breath, and when Crane stepped back and finally withdrew his softening cock, even more cum cascaded from Dennis's ass, dripping around my shaft and down my nuts. My grandson slowly rolled off me and stayed on his stomach on the bed as I stood up. He seemed exhausted.

    "Holy shit," I said softly, unable to contain my reaction when I saw Dennis's gaping asshole. It was red and raw and coated with the creamy remains of our loads that continued to leak out.

    "Yeah," Crane said in an approving tone, smacking the teen ass in front of us. Then, he turned to look at me and placed his hand on my shoulder. "It's good that you were here. He's going to remember this night his whole life." He spoke with such assuredness, it seemed like this wasn't the first time he'd led a young man to sex with someone in his own family. Crane must have an interesting history, I reflected, and maybe sometime I'd ask him about it.

    But not tonight. Before getting dressed, Crane scooped Dennis up and carried him into my bedroom. It seemed like he knew that what my grandson and I needed to do now was cuddle up and rest. The math teacher let me know that he would see himself out, and I climbed in bed next to Dennis to wrap him in my arms as well both drifted off to a well-earned slumber.​​