Dare Me ... More! (Chapter 8)

By Evelded
published May 24, 2021
5334 words
Summary

As Dylan and Brandon’s temporary amnesia is lifted, they have a flashback to the previous day and recall just what the hell their “Master” had them doing.

Previously, our heroes, Brandon and Dylan, both of whom are under a compulsion to take any dares they’re given, (a) realized that they had twelve or so hours of missing memories due to a dare; (b) performed a sexy striptease for Brandon’s crush, Dana, and her friends; (c) took a somewhat harrowing naked ride to Dylan’s house that involved frequent nude Chinese Fire Drills on public streets and also oral sex while driving, and (d) got into bed together and started giving each other handjobs before (e) finally forgiving each other for the malicious (and frequently sexual) dares they’d forced on each other in the past. Then, to their surprise, upon agreeing to bury the hatchet, both guys suddenly regained their memories of what their mysterious “Master” had been doing with them over the previous day.


Saturday morning, 11:30 a.m., about 15 hours earlier (Brandon)

“Okay boys! SHOWTIME!” said Kyle, the manager/owner of Miss Pretty’s House of Pleasure, the costume shop and sex toy emporium that Dylan and I had been dared to visit as part of our upcoming strip show.

Unfortunately, by happenstance, Kyle became aware of how Dylan and I were compelled to accept any dare given to us. Dare, in this instance, was broadly defined, and it was possible to dare us to do things like get instantly hard, to masturbate for hours without cumming, and even to no longer have a gag reflex. After forcing us to reveal everything that had happened to us since this whole mess started, Kyle even had the nerve to lecture us on how we’d used the dare compulsion against each other even though we’d been friends since high school. And Kyle then decided to take on the role of karmic avenger and punish us both for being “assholes” to each other.

Which was how Dylan and I ended up butt-ass naked in front of the guy. And also why we’d just spent the last five or so minutes with rock hard dicks grinding up against one another while moaning out a lot of gay sex talk, much of which I suspect had been recorded on the digital camera we were now facing. I couldn’t even get angry over it because the fucker had dared us to “smile at the camera,” and so we were both grinning like loons as if we were thrilled to be in whatever homemade porno Kyle was setting up.

As I looked around, I realized Kyle had set up more than just a camera. There was also a flatscreen TV he’d brought in that was hooked up to the camera, and on it, I could see Dylan and myself, both with our throbbing cocks and delirious smiles. There was a laptop plugged into the TV as well.

“Okay, listen up, boys,” Kyle said imperiously. “You guys have graciously volunteered to perform a striptease for a bachelorette party, and being something of an expert in that, I insist on making sure you put on a good show. To that end, I’ll be giving you a crash course in how to shake your money-makers. So … I dare you to be completely attentive to everything I tell you. I dare you to do your best to remember and absorb the lessons I’m about to give you on stripping. And I dare you to be completely excited and fully into learning how to be a good male stripper.”

He paused. “I also withdraw my dare about you smiling all the time. It’s just … creepy.”

Finally, my mouth relaxed out of that grin that was beginning to hurt a bit. While I couldn’t help but focus on everything Kyle said and was going to say, none of his dares required us to be respectful about it. So naturally, Dylan had to open his big mouth.

“You’re an expert stripper?” he asked in disbelief.

And to be honest, it did seem improbable. Kyle looked to be in his 50s and had a pretty big gut. The idea of him pole-dancing in a G-string did seem unlikely. But I winced at the question anyway, since there was no telling what he could do to us for the sin of rudeness.

“I will have you know, asshole, that I was a successful professional exotic dancer for fifteen years before I saved up enough money to open this store. And while I may have let myself go in semi-retirement, I had washboard abs for most of that time.”

Then, he narrowed his eyes before grinning. “I dare you both to believe that I’m the best stripper coach in the world and to be completely awestruck and incredibly grateful that I’m willing to give you pointers. Oh, and I also dare you to call me Master. In fact, after you leave here, I dare you to forget everything you know about me except that my name is Master. Got it?”

“Sure thing!” I said almost giddily. It was a small price to pay, after all, to get instruction from the best stripper coach in the world, no matter how unhappy I was about being forced into a strip show anyway.

“Whatever you say, Master!” Dylan added earnestly.

And with that, Master clicked something on the laptop, and Billy Idol’s “Hot In the City” started playing. Master moved to stand between us, and he started showing us how to work our bodies in time with the music. I was so intent on learning everything he had to teach us, that I really didn’t mind the fact that I was totally naked and erect the whole time, and Dylan obviously felt the same way.

Then, to give us a better idea of what he wanted, Master also played a video that had been saved on the computer. And to our surprise, it was Master from a performance back in the 1990s. He was indeed very lean and muscular back in the day. I still wasn’t gay—no matter how many sexual dares I’d gotten from men lately—but I was enough of a gym rat to appreciate the male form. Young Master did indeed have a well-developed six-pack back in the day. At Master’s direction, we started trying to imitate his moves while he critiqued and demonstrated.

After a couple of hours of practice, my stomach was growling, and Master kindly asked if we’d eaten that day. Neither of us had eaten since breakfast. I’d scrambled up some eggs and fried some bacon for myself. I’d also scrambled some eggs for Dylan … and then dared him to jerk off into them before eating it all. Master frowned at that, but I was unrepentant, even though I knew I’d pay for it later. Master then dared us to give him all the cash in our wallets and also to continue working on our routine while he was gone on some errands.

We did as commanded, though tensions remained high between us. We’d been naked and hard for hours at this point, and we started arguing with one another about whose fault it was. I bet it would have looked funny to any outsiders, because we were having this shouting match with one another while bumping and grinding and generally thrusting our dicks at one another. And the weirdest thing? More than anything else, right now, I was mad at Dylan for arguing with me because it distracted us from perfecting our routine! Master had dared us to be “completely excited and fully into learning how to be a good male stripper,” after all, and at the moment, fulfilling that dare took precedence over all the other reasons we had to be pissed at one another.

And thus, when Master strolled back in thirty minutes later with several bags under his arms, he was treated to the sight of us calling each other names while twerking our asses into the camera and looking over our shoulders to make sure we were doing it right.

“God, you two are ridiculous baby-men!” he snapped while putting the bags down on a table. There were several sacks from a local drive-in restaurant—not my favorite place, but pretty famous for their jumbo foot-long chili dogs which I could smell from here. There was also a large bag from a Pay-Less Shoe Store.

“I dare you to stop following all the dares I gave you after I first said ‘Showtime’ except that you’ll remember everything you learned about stripping and you’ll keep calling me Master. I like the sound of that. Oh, and I dare you to keep the hard-ons, at least for a little while longer.”

Instantly, it was like someone had splashed cold water in my face. I clearly remembered the time Dylan and I had spent learning the dance moves Master had taught us. But the obsessive need to master them was gone. Well, for the time being, anyway. Mainly, I was focused on how hungry I was, even though chili dogs weren’t my favorite food by any means. Master looked at us, still angry at our constant bickering.

“So,” he said. “Refresh my memory. When was the last time each of you came? And under what circumstances?”

The dare to always tell him the complete truth had been made before he said ‘Showtime,’ so we both had to answer.

“I dared Dylan to wake me up with a blowjob this morning. I also dared him to have no gag reflex, and I made him dare me to not have any hangups about receiving blowjobs and other sexual favors from him.”

Dylan glared at me, but I just shrugged. It was the truth after all.

“And I came several times last night after Brandon dared me to have erotic dreams about public humiliation,” he practically snarled. “Before that, it was when he dared me to jerk off into a protein shake and drink it!”

Despite the situation, I couldn’t help but laugh at his expression. Master just shook his head. He opened up the food bag to pull out a foot-long chili dog. He unwrapped the monster dog, put it on a paper plate, and then set it in the middle of a small table standing nearby. Then, he took the camcorder off its tripod so he could point it manually.

“Okay, boys,” he said. “Time to get your protein for today. I dare each of you to become incredibly horny and to start jerking your dicks over that hot dog. And when I give the word, I dare you both to spooge all over it!”

Helpless to resist, Dylan and I moved over to opposite sides of the small table and started masturbating. Instantly, a wave of sexual energy poured over me as I jerked faster and faster. Dylan’s face was ecstatic, so I knew he felt the same. Meanwhile, Master was filming us from all angles. The bastard kept us on edge for about five minutes before finally giving the word.

“Okay, boys. On the count of three, I dare you to have the biggest orgasm you’ve ever had. And I dare you to make sure to cum all over the half of the chili dog that’s nearest to you. One! Two! THREE!”

For a second, I thought I was having a stroke. My entire body shook with the force of the orgasm. Ropes of cum came out of both my dick and Dylan’s. My vision blurred for a few seconds. And yet, somehow, both of us were still able to aim our dicks properly, and nearly all of the cum landed on the chili dog. It was amazing precision, I had to say. It was also revolting to look at. Once my vision cleared and I could start breathing normally, I took my hand away from my spent dick and looked at the violated junk food. It looked kind of like someone took a jar of mayo that had gone bad and dumped it all over the chili dog. Just looking at it made me want to puke. And yet, with the way my luck had been going, I was pretty sure I’d be eating the disgusting thing in the next few seconds. Sure enough, Master pulled the camera up from the dog to focus in on Dylan’s face.

“So, Dylan?” he said. “After drinking your own cum in a milkshake and then Brandon’s cum during a blowjob, what do you say? Should we make Brandon eat your cum and his along with that dog?”

Dylan smirked cruelly. “Hell yeah! Let the fucker choke on it!”

I glared at him. “Laugh it up, Dylan. You’ll get yours at some point.”

But Master just sighed loudly.

“Right. So the concept of being the bigger man is completely lost on you both.”

With that, Master reached down to the table to rotate the paper plate 180 degrees.

“There we go! Now, you’ll each get to taste what the other’s cum is like when used as nature’s condiment!” We both cursed under our breath. “When I give the signal, I dare you to pick up the dog together and start eating from opposite ends until you reach the middle. I dare you to think that the taste of cum and chili together is the best thing you’ve ever eaten in your life. I dare you to feel waves of orgasmic pleasure with every taste. Go!”

And with that, we each carefully grabbed our end of the cum-laden hot dog, bit into our respective ends … and moaned. I can’t describe it. I fucking lived it and I still can’t describe it. The best explanation I can offer is that it was like having a cum-free orgasm with each bite, followed by a sustained mini-orgasm for as long as the taste of chili lingered in my mouth. Looking back, I’m amazed that neither of us collapsed due to our knees buckling. We were both torn between eating the chili dog as fast as possible to experience the pleasure overload and savoring each bite to make the after-orgasm last as long as possible.

After what seemed like an eternity but was probably less than two minutes, we met in the middle, biting the last bit of chili dog in two to finish it off. In the process, our lips brushed together, and we simultaneously realized the same thing. By this point, we both had several days of stubble on our faces, and even under the best of circumstances, it’s hard to eat a chili dog and be neat about it. Consequently, both of our mouths were covered in chili.

Dylan and I stared at one another with glassy eyes. Then, without even being dared, we started forcefully licking one another’s faces to get every last bit of that mind-blowingly delicious taste we could. And when we’d both licked each other clean like a pair of hungry, slutty dogs, we both realized that the taste of the chili still lingered in our mouths. And so we went from licking one another to kissing one another … hard. For several minutes, I explored every bit of Dylan’s mouth that my tongue could reach, and he did the same to me. And the whole time, we were both maddeningly horny, not for each other, but for the slightest taste of the spicy food that I feared I might now be addicted to.

Finally, after several minutes of this, the obsession died down enough for us to pull apart, and we each took a step back. We were both breathing hard, and even after that massive ejaculation earlier, we were both erect again.

“Did you both enjoy your chili dog?” Master asked lightly. I turned towards him and saw he was still holding the camera. I wiped my hand over my face in a futile effort to clear it from the haze of what had felt like a five-minute-long orgasm, the culinary equivalent of getting our brains fucked out. Dylan just nodded dumbly.

“Good! Because you’re both growing boys, and you need more than half a hotdog each if you’re going to make it through the day!”

He slid the paper plate back over to us. Apparently, while we were trying to scrape every last bit of chili out of each other’s mouths, he’d unwrapped a second foot-long.

“I dare you to start jerking again.”


3:00 p.m. (Dylan)

Finishing off the second cum-soaked chili dog took even longer. Master dared us both to eat slower and chew each bite twenty times before swallowing. He also dared us to feel that same mini-orgasm with each chew. Basically, we were edging ourselves like crazy without even touching our dicks. Between eating the chili dog and then licking each other clean like we were actual dogs, it took nearly half an hour to finish.

And then, Master pulled out a third chili dog.

I whimpered at that because after a night of wet dreams and the two mammoth cumshots I’d just made, I wasn’t sure I had anything else in me. Luckily, Master had something else in mind.

“As I recall, Dylan, Brandon here indirectly made you suck off a pizza delivery guy and then intentionally made you wake him with a blowjob, right?”

I nodded slowly.

“Whereas you only indirectly ordered him to suck off a repairman. So the way I see it, he’s still behind one blowjob.”

And with that, Master dared me to stand still with my hands behind my head. Then, he dug his fingers into the chili dog and smeared the now-cold chili all over my erect cock.

“Okay, Brandon, I dare you to suck all the chili off this dog! I dare you not to bite Dylan at all but to get every trace of chili off of him. And I dare you to continue feeling orgasmic pleasure from the taste of it. Dylan, I dare you to stand there and enjoy it but not to cum from it. And since you did it to Dylan first, Brandon, I dare you to no longer have a gag reflex.”

Brandon glared at me, but he was helpless to resist. He dropped to his knees and started sucking me off. Almost immediately, he started moaning softly just from the taste of my cock, and soon, I was moaning as well. I longed to put my hands on his head and run my fingers through his hair like he had with me this morning, but my hands were still stuck behind my head. It took Brandon about five minutes of continual licking and sucking to get my dick clean enough to suit Master, and he finally had Brandon stop. Then, Master turned to me.

“So what do you say, Dylan? Are you two even now? Or do you think Brandon should suck another load of chili off of you?”

I looked down at Brandon, who was still on his knees in front of me. His eyes looked desperate. While he was ‘in the moment,’ he was happy to experience the weird pseudo-orgasm from Master’s dare, but once the dare ended, he was disgusted with himself for his responses.

I had a brief stab of pity for Brandon. But then, I remembered the disgust he made me feel after that trick with the “piggy porn” he’d forced me to watch and be turned on by. The thought of making Brandon suffer through another round of “food porn” was irresistible.

“Well, Master, we do have some more chili to finish off, right?” I said with a smirk. “Seems like a shame to let it go to waste!”

Master just sighed loudly. “So the concept of proportionate revenge is something you don’t understand either. I swear, you two are the most pig-headed straight boys I’ve ever met. Fine. I dare both of you to get on the floor in a 69 position.”

I felt the blood drain from my face as I obeyed the dare. ”Shit!” I thought. ”We might have been done with this if I hadn’t decided to get back at Brandon some more!”

Brandon evidently agreed. “Idiot,” he muttered loudly as he positioned his head next to my cock. Then, Master smeared some more chili onto both our dicks before daring us to go to town. And as we worked on each other in a frenzy of lust that made my head spin, Master kept adding chili as needed to make sure we never quite finished.

Imagine giving and receiving head for an hour and feeling the effects of an orgasm the whole time but not actually cumming!

When Master finally ended the dare, Brandon and I both rolled over onto our backs. I could only stare at the ceiling in silence, too tired to even wipe the mix of Brandon’s pre-cum and my own drool off of my mouth. And the craziest thing is that somehow, after everything I’d been through in the last few days my dick didn’t even feel sore!

“Okay,” said Master while fiddling with my cellphone. “I need to run a few quick errands, and you boys have had a long day. I dare you to take a nap and not wake up until either I wake you or the alarm I’m setting goes off. While you’re asleep, I dare you to dream about everything you’ve dared the other to do but to imagine it had been you forced to obey the dare instead of him. Nighty-night.”

I tried to speak, but my eyes fluttered. In seconds, I was out cold.


5:30 p.m. (Still Dylan)

“Wakey-wakey! Eggs and bakey!” Master said loud enough to jerk me out of the dream I’d been having. The one where I was the one forced to act like a dog for the entertainment of a repairman before sucking him off. Oddly, I took to it better than Brandon seemed to. Weird.

“Okay, boys. Play-time is over for now. Let’s see how you look in your costumes!”

He gestured towards the table which had two identical UPS driver stripper-outfits waiting for us, along with breakaway boxers and thongs. In the Pay-Less Shoe Store bag were two boxes each containing Timberland work boots in our sizes, along with some brand-new wool socks. At Master’s direction, we quickly dressed. He didn’t even need to dare us. By this point, we were desperate to feel something covering our naked bodies, even if it was something we knew we’d be taking off again soon enough.

“Hot stuff, fellas,” Master said. “The hens will just love you. Now let’s see how well you can put together all the stuff you learned earlier today while actually stripping.”

We were both moving a bit slow, as the mindfuck of the past few hours was still playing with our heads. Master looked at us with something oddly like pity.

“I dare you both to feel upbeat and full of energy and to be totally focused and excited about stripping.” He paused and spoke again. “I dare you to forget about all the stuff you did to each other with the chili—and everything else you did today that you feel was traumatic in some way—until I tell you to remember it again.

Boom! A rush of energy hit me, and just like that, I was excited to get back to work on our routine. Clearly, the nap had done me a world of good, and despite our situation, I was grateful to Master for giving us a chance to rest a little. The only distraction was the odd awareness of the taste of chili in my mouth, even though I didn’t remember eating anything since this morning.

Brandon seemed as cheerful and upbeat as me, and at Master’s direction, we quickly got back into the swing of male-stripping. It was weird at first learning how to properly yank on our breakaway shorts so that they came free at the right point in the music, but thanks to the dares we were under, both Brandon and I were quick studies. On some level, I marveled at how this Dare Me curse could actually be beneficial, and I wondered if I could persuade Master to dare me to go to the gym more regularly or to stop smoking and drinking so much beer.

After a couple of hours, Master had us stop. We’d just completed a run-through of the routine that ended with us throwing aside our UPS caps in perfect unison on the last beat of the song. Then, we both froze in place, with big grins on our faces, our hands on our hips, and our dicks at full mast, while we waited for Master’s critique. He said nothing at first. Instead, he simply walked around us to check out our bodies from all angles. Despite the fact that he was gay and we were butt-naked, he wasn’t leering at us so much as judging us. It was mildly intimidating. Then, he looked at his watch.

“Yeah,” he muttered. “We’ve got plenty of time.”

By now, it was 7:30, and I couldn’t help wondering what he meant. “Um, plenty of time for what, Master?”

He smiled evilly. “Manscaping! I can’t let you two give a strip show with all that butt-hair and those overgrown bushes.”

“Now wait just a minute…!” Brandon started, but Master gave him a warning glare and he shut up fast.

“Okay, I’ll need to make a quick phone call, but before I go …” he paused thoughtfully. “Do either of you think that there’s anything the other dared you to do that you still want revenge for?”

To my surprise, Brandon didn’t say anything. Unfortunately, I was still under a dare to always answer truthfully, and there was one thing Brandon did to me that really pissed me off.

“Um, I kinda still want revenge for that “laugh uncontrollably until you piss” dare,” I said hesitantly.

Brandon fumed. “Goddammit, Dylan!”

“I’m sorry!” I said sincerely. “Really! But I can’t lie about it! And laughing that hard for that long really sucked!”

“Hmm,” said Master. “Well, neither one of you is peeing in my store! But … if I remember the story correctly, that asshole repairman made you piss on your living room floor, right Brandon? And then Brandon made you piss in your car, right Dylan?”

We both nodded.

“Okay, then. When you’re done with the strip show for the girls, I dare both of you to go back to Dylan’s place to spend the night. When you get there, Brandon, I dare you to pee all over the inside of your vehicle. Dylan, as soon as you step inside your house, I dare you to pee all over the floor. That’s fair, right?”

“You have an incredibly fucked-up definition of the word ‘fair,’ Master,” Brandon said drily.

“So I do. As for the laughter bit …” He told us both to take a seat facing each other and dared us not to get up until he gave permission. Then, he handed me my phone and dared me to pull up a stopwatch app.

“Now then, when I say go, Dylan, I dare you to start the stopwatch. At the same time, Brandon, I dare you to imagine that you’re incredibly ticklish and are being tickled all over your body with feathers, fingers, vibrators, whatever. I dare you to laugh until it hurts but to be unable to get out of that chair or do anything to stop it. I dare you to laugh harder and harder until Dylan here says Stop.”

Brandon went completely pale as Master turned back to me.

“Dylan, whenever you genuinely feel that Brandon has suffered enough, I dare you to say Stop to end his tickle torture. At the same time, I dare you to pause the stopwatch and see how long you left him to be tickled. With me so far?”

I nodded slowly, though I was confused about why Master was giving such an overcomplicated dare.

“Next, after you stop Brandon’s tickling, I dare you to set a timer for the same length of time that he was tickled. Then, I dare you to start it and say ‘Go.’ At that point, I dare both of you to be tickled insanely until the timer goes off!”

My eyes widened. So I would get revenge against Brandon for the laughter dare but we would then both suffer for the same length of time. More of Master’s fairness.

“One final thing, Dylan,” he added with an evil smile. “I want to see if this works. As soon as I say ‘Go,’ I dare you to forget the last part of that dare until you pause the stopwatch. In other words, I dare you to forget that however long you choose to tickle torture Brandon, you and he both will then get the same amount of torture together!”

My eyes widened in horror. That meant that however long I chose to see Brandon tortured, I would get the same treatment myself right afterwards, a fact I wouldn’t remember while I was watching him be tickled! If I chose to be a jerk (which seemed to be my default state lately), we both might get tickled for hours!

“Brandon, I dare you to not say anything to Dylan about that last bit. You can beg for mercy all you want, but you can’t tell Dylan that he’s actually deciding how long he’s getting tickled next.”

Brandon fumed but said nothing.

“Ready! Set! Go!”

I hit the start button while Brandon began laughing hysterically and flopping around in his chair. In no time at all, he was begging for mercy.

“D-D-DYLAN, HAHAHAHA, PLEASE! I’M B-B-BEGGING YOOUAHAHAHA!”

Now oblivious to my own waiting torture, I leaned back in my chair to enjoy the show. Within minutes, Brandon was clutching his shaking ribs, and tears were flowing down his face, even as he roared with laughter. At first, I was enjoying the sight of him and the knowledge that I was getting my own back. But as his suffering increased, I remembered what I felt like laughing like a maniac in my car last night. It was awful—sheer torture. And despite my desire for revenge, I grew uncomfortable with Brandon’s suffering. We’d been through a lot together, and I’d learned the hard way the value of mercy. Even if I was, as Master put it, “a hard-headed straight boy.”

“STOP!” I yelled out, and instantly, Brandon’s laughter died away. He looked at me with what seemed almost like gratitude. But then, my own eyes widened as I remembered what I’d been dared to forget. I glanced down at the stopwatch.

“Fourteen minutes, thirty-three seconds,” I said hollowly as I set the timer for that duration.

Honestly?” Brandon gasped. “I … I figured you’d have … gone a lot longer.”

I smiled grimly. “Maybe I’m learning to not be such a shitty friend. Ready?”

Brandon took a deep breath and nodded. I started the timer, said ‘Go,’ and within seconds, we were both hysterical. We sat across from one another, bellowing out our laughter as invisible fingers and feathers ripped us apart.

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