Dare Squad

By Cliffy B

Published on Jun 3, 2021

Gay

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All events are fiction. All characters are a figment of imagination. All character's represented in this story are 18 or over.

Hope you enjoy, any feedback is welcomed and much appreciated. E-mail me at: bootusrim@gmail.com.

Dare Squad

"Dude, Sephiroth is way too overpowered. You need to stop using him." I was beginning to get frustrated with having my ass handed to me by Craig on Smash Brothers.

"Fuck that, I paid good money for him; I am going to use him!" Figures. Craig's always been competitive.

"Stop whining. You just need to get good, Ty." That's easy for Lewis to say, he has the game so gets to practise.

"How about I dare Craig to not use Sephiroth anymore?" I give a cheeky grin as I try to make Roy jump high enough to get the Smash ball.

"Oh, that's lame. That can't be an official dare. Lewis?" Craig gives me a gentle kick in the back.

"Due to all members not being present there can be no official dare." My grin turns to a frown as I finally get the Smash ball, only to find it was a fake, exploding in Roy's face and catapulting him across the screen. My last life lost, I silently curse my luck as I drop the controller to the ground.

"What up, ladies?" I look behind as the fourth member of our group joins.

"Hey, Dayle." We all greet him as he slumps into the grey comfy chair, sweaty from the spring heat.

"So, now we're all here; can I make the dare official?" Craig and Lewis's characters are still battling it out on screen. Both still with two lives.

"Ooooooh, a dare. Let's hear it!" Dayle's eyes widened with excitement.

"Calm down, it's super lame." Craig is still unimpressed by my dare. Though, he would be. Means he has to use another character. Not that he wouldn't still be able to beat me. Just means I'll last longer.

"It's not lame. I dared Craig that he couldn't use Sephiroth anymore." Okay, it is lame. And petty. But I'd like to have the chance to win, if just once!

"Oh. Naw, dude. That's totally lame. Besides, I'm here now, so you're going to get your ass beat no matter who Craig plays." I give Dayle the middle finger.

"Shit." Craig kicks me again, though this time accidentally as he shuffles into a new position after losing a life to Lewis. "So, does the council officially strike down the dare?"

"Yes." Lewis and Dayle give each other a look before answering in unison.

Okay, let me explain a few things. Me, Lewis, Craig and Dayle have been friends since our first day of elementary school. Assigned to the same table, we'd spent class chatting and being friendly as only six-year-olds can. Then when lunch came around Dayle didn't like his sandwiches, so dared Craig to swap with him. This caused a few arguments as we went around daring each other to swap sandwiches, chips, candy bars and drinks. In the end, Craig loudly proclaimed there had to be some rules to daring each other. From that point on, we've been inseparable.

Now in our last year of high school, you'd think the whole dare thing would have lost its appeal, but if anything the opposite has happened. While once they were silly things like swapping sandwiches or picking a flower from Mrs McGinn's garden, they'd escalated to things like mooning the principal, changing Molly Thompson's test score and streaking during the football playoffs. Well, not a full naked streak. As I said; we had rules. Most dares we can debate on, with the ones not involved in the dare being the council'. They give the final verdict on whether the dare is official' or can be disregarded. However, there are four rules that are not up for debate:

  1. All four members must be present for the dare.

  2. Only one official dare at a time.

  3. No dare can put anyone in harm's way or get them arrested.

  4. If you refuse an official dare that has council approval you can no longer be a part of the group.

Only once has any of the four rules been broken. We used to have another friend, however, he-who-shall-not-be-named flaked on a dare and as such was cast out. It might seem harsh, however, if you're not going to be up for it, then what's the point? Maybe, the whole, not saying his name or speaking to him or acknowledging his existence is going a bit too far, but, it's certainly meant no one else has turned down a dare.

While we've had fun, we quickly got a reputation for ourselves. We used to have rules that dealt with other guys wanting to join the group. But, those have never been used. It's not that we've ever done anything to hurt anyone, and Molly Thompson got her real grades in the end, it's just we signalled ourselves as being outsiders to everyone else. A reputation that travelled with us through middle school and to high school. Even the jocks left us alone after we put dye in the showerheads. They ended up going round as smurfs for almost a month. Thankfully, no one could prove it was us, so we never got into any official trouble.

For this sunny, April afternoon, we'd come to Craig's house. We often came to Craig's house. His dad left and his mum works long hours. Meaning we often get a lot of privacy. Not that any of our dares get sexual or anything. We're four straight guys after all. Well, there was the time last year when Dayle dared me to jerk off into my sandwich and eat it. However, that wasn't about it being sexual. Dayle was just being a dick because I'd dared him to steal his dad's beer and he'd been grounded for a week.

Sitting on the floor, in front of Craig who sat next to Lewis on the couch, I thought about how none of us has ever had a girlfriend. An unfortunate result of us being outcasts I suppose. Though, Dayle says he lost his virginity to a girl while on holiday last summer, I don't think any of us believe him.

Not that he isn't attractive. He's a pretty handsome dude. Shiny brown hair, combed over to the right of his triangular face. High cheekbones and a mischievous smile with a clear complexion. He never had the acne troubles most of us did. He's pretty skinny and just under 6' it kind of shows in how his clothes all look pretty loose on him.

No, the reason why we don't believe him is that he's been known to lie about these things. He once said he'd made out with Kirstein Winkler behind the bleachers on the field, so we dared him to go up and talk to her. Kirstein is a beautiful and popular cheerleader, the conversation did not go well. Even in his humiliation he still wouldn't admit he'd lied. Thankfully for him, we decided that daring him, to tell the truth, was too lame and despite really wanting to know we let it go.

"Well, if Ty-Dye's dare's a flop, I've got one." Yes, yes it was me who was dared to put dye in the locker room showerheads. The trick to avoiding detection from the security cameras was to climb through the window. Since then Dayle's given me the nickname of Ty-Dye.

"What you got for us?" Craig pauses the game as we all look at Dayle.

"I dare Ty-Dye," he looks me dead in the eyes as he puts his sneakered feet up onto the pouffe in front of him, "to give me a foot massage."

"Oh, fuck off!" I turn to the council on the couch. "That's so stupid. You can't let the dare stand." It's not like Dayle to make such a stupid dare. He doesn't dare often, but when he does they're usually pretty juicy.

"If it helps, my feet are pretty ripe from walking around town all day looking for a suit for my sister's wedding." Dayle gives a hopeful smile to the council.

"No." Craig and Lewis answer in unison. We've gotten pretty good at that over the years. "The council turns down the dare." The guys unpause the game and turn back to the large, flat-screen TV.

"Okay, I'll enact the multi-dare clause." The game is instantly paused again as we all turn back to Dayle.

The multi-dare clause is a risk. It means we can make a dare without council approval. However, the dare must have multiple parts -as the name suggests- and once all the parts are complete the council will then get to judge if it was satisfactory or not. The risk being if ruled to not be satisfactory the one that was dared gets a free punishment hit on the one who gave them the lame dare(s). This has never happened. The multi-dare clause has rarely been called, but we've discussed punishments before. The most popular one being a free-kick to their balls.

"Well, as long as you're sure and you know the risk of the dare being lame?" Craig gives him the chance of backing out.

"I understand and I will continue with the multi-dare." Dayle toes off his sneakers, his cocky grin plastered on his face as the black vans make a soft thud on the carpet.

Rolling my eyes, I crawl over to the pouffe. All I can do is hope the other parts are as lame as this one and I can get a free-kick at his balls. It's not that I dislike Dayle or anything, it's just that his cocky attitude can get on my nerves. He can also be pretty self-centred at times. He's the only one who's had a dare turned down for putting another at risk. It would be my pleasure to have Craig and Lewis hold him down as I get to kick him down a peg or two.

Kneeling up in front of the pouffe, I reach out to Dayle's feet, covered in white `invisible' socks. You know, the ones that don't go past your ankles so you can wear socks and shorts without it looking stupid.

"Nuh-uh. Remove my socks first, please, Ty-Dye." Ever since he gave me the jerk in my sandwich dare, Dayle's has been pretty condescending towards me. Another reason I'd love to kick him in the dick.

With a sigh, I take each sock in turn and pull them off his feet. My nostrils are instantly hit by a sweaty, musky scent. I make a show of scrunching up my nose and face, however, the smell's really not that bad. They're not cheesy at least!

Grabbing his right foot in both hands, I press both thumbs into the centre of his soles, making small circles. The skin's damp from his sweat and radiates heat into my hand. Dayle sighs above me as he sinks further into the comfy chair.

I hear the sounds of Smash Brother's as I assume they've unpaused the game once more.

Despite being pretty tall, Dayle's feet aren't especially big. I've no idea what size he is, but as I move my thumbs up and down the spongy muscle I can't help but notice how small they are for him. As I press against his big toe, I can't help but smile as I notice how squat it looks. You know what they say about feet size and cock size. I stifle a giggle as I think about Dayle having a small weiner.

"Fucking hell! See, Ty. Sephiroth isn't overpowered! You just suck." It seems the game's over, and Lewis won. "You jumping on Dayle, seeing Ty's unavailable?" Despite Dayle's earlier statement, he's probably the worst out of us at Smash.

"Naw, dude. I'm just going to enjoy my foot rub." Looking past his feet to his face, I can tell how relaxed he is.

"Well, you want to team up against CPU's?" Craig obviously doesn't want to have another 1-on-1 with Lewis.

"Sure."

Changing feet, I give the same treatment to his left. My thumbs are now getting a bit tired from the pressure needed. Maybe he noticed I'm no longer putting as much effort into it, so decided to get the next part of the dare going.

"Okay, Ty-Dye. Now lick my soles and suck on my toes." Really? Does he think this will escalate his lame-ass dare enough to not be punished? It's obvious he just wanted a foot massage.

"Didn't realise you had a foot fetish, dude." Maybe if I can make him feel some shame about it he'll call it off now and we can move on.

"Hey, don't judge it till you try it." No luck. Though, Dayle is pretty shameless.

Without any further objections, I lean down and put the big toe of his left foot in my mouth. Sucking a little, I then move onto his other toes. A bit salty, but not unpleasant.

With the toes finished, I hold up his foot in my hand as I prepare myself to lick the sole. Taking a deep swallow, I stick out my tongue and drag it from his heel to the bottom of his toes. Again, just a bit salty. Going back down I do it again, slower this time.

Though smallish, his feet definitely are not dainty. Not like a girls'. It's definitely a dude's foot. Which makes my twitching cock a little embarrassing.

Okay, I admit; I'm the one with the foot fetish. My favourite thing to jerk off to is a girl on her back, legs sticking up with her feet together. I've shot countless loads to thinking about fucking Sara McMillon while holding and sucking on her toes.

Tragically, I've never had the opportunity to experience this, what with still being a virgin and never having had any sexual contact with anyone else. Maybe that's why this is causing my cock to harden; I'm getting to live a fantasy. Just not with the right gender.

Putting his left foot down, I close my eyes as I start sucking on the toes of his right. This time imagining it's Sara with her toes in my mouth and not Dayle.

Taking my time, the fantasy and the flesh in my mouth have me raging hard. Thankfully, Craig and Lewis can't see how much I'm enjoying myself.

With his feet fully licked and sucked, I pull my head away and look up at Dayle. His own eyes are closed, and if I'm not mistaken a slight bulge in his navy blue cargo shorts. If it wasn't for my own erection, I might have pointed it out to the others in the hope of making him too embarrassed to continue.

"There, all done. Now, I submit to the council the lameness of the multi-dare and request permission for punishment."

"Hey, not so fast Ty-Dye!" Dayle interjects even before Craig can pause the game. "This isn't over yet!" I look up at Dayle in confusion.

"Okay, but just to clarify that you can't make him do something completely different. The multi-dare has to all be related." Craig looks at Dayle with scepticism.

"I'm well aware of that." Dayle pauses, all cockyness gone from his face. If I'm not mistaken, he actually looks a bit apprehensive.

"Okay then, what's the next part of the dare? And you can't delay it." I'm pretty sure Craig actually has the rules written down somewhere.

"I know, I know. Okay," Dayle takes a deep breath, before looking down at me, the cocky grin returning to his face. "Next part of the dare, is for you to take off my shorts." Pause, "and underwear." Another pause as I look at him with horror. "And suck my cock."

"Fuck off! I am not sucking your fucking dick!" I'm instantly on my feet! "Guys! Sucking dick is not a legit dare!" The fuck? Why is he asking me to suck his dick? Is he gay? I know I'm not gay!

"Actually, Ty, there's no actual rules against sucking dick. It also doesn't breach the four unbreakable rules. As such it is a legit dare." I open and close my mouth, trying to find something to say, some rule that will get me out of this. However, I can't find any. I either have to suck Dayle's dick or be kicked out of the group.

"Besides, it looks like you enjoyed sucking my feet." All eyes go to my crotch. My dick's still pretty hard, bulging out the front of my thin football shorts.

"I was imagining it was ... Sara McMillon. Only thing stopping me from throwing up!" I throw the last part at Dayle as I try to kill him with my gaze.

"Either way, Ty-Dye, the council has spoken." Dayle flutters his eyebrows at me as he pushes the pouffe to one side and spreads his legs.

"Wait, Lewis hasn't said anything!" I look to Lewis, pleading with him to help me.

"Sorry, dude. I'm with Craig on this one. Plus, the council can't intervene until the final part's been completed." He gives me an apologetic look as I turn back to Dayle.

Never before have we gotten sexual. I mean, sure we dared each other to show our cocks or flash our bits. But that was just curiosity and kids being stupid. Though, we haven't done anything like that since we hit puberty. I think we just became a bit too self-conscious. So, why was he doing this now?

"It's okay, Ty-Dye. I'll go easy on you." He gives me a wink as I resign myself to my fate and kneel back in front of him. "Mum woke me up early to go shopping, so I didn't have a chance to jack it off this morning, so I'm super horny. I'm sure you won't be down there long." I guess that explains why.

"Well, couldn't I just jerk you off then?" I'd rather not do either, but given the choice, I'd rather take jacking off any day.

"Sorry, Ty-Dye. Need to make sure it's good enough so I don't get kicked in the nuts." I hear a suppressed laugh from behind me. I got to give it to him; that was pretty clever.

Taking several deep breaths, I eventually gather up the courage to reach up and undo the button of his shorts. The dares always give me nervous butterflies. It's the whole thrill and reason I enjoy them. And while the butterflies are definitely there, it's different this time. There's something so ... personal about sucking another dude's cock.

Suppressing my nerves, I grab the waistband of his shorts. Well, if his feet are anything to go by he's got a small dicks at least. So, I shouldn't have any problems with it. Hell, maybe I can embarrass him over his size and get him to drop this stupid dare.

Pulling his shorts down over his knees, I let them drop to his feet as I stare at the bulge in his boxers. The material being lifted up by what I assume to be a cock much bigger than I was hoping for.

Tentatively, I grab hold of the black boxers, lifting the waistband over the hard cock, my mouth gapes open as I get my first look at Dayle's big dick. Probably reaching up to around 8 inches, it's also fairly thick. Definitely a mouthful. I also take in the head of Dayle's cock. A rounded triangular shape, which is different to my own.

"Impressed?" Dayle gives me a friendly, yet cocky smile. It's weird. I've never seen him with such a smile before.

I don't reply. I close my mouth and look away from him. I finish pulling his boxers down, letting them pool with his shorts. I just stare at his hard, bouncing cock as it lays against his white, baggy t-shirt. His balls and pubes are completely shaved. Though, that's not a decision Dayle made. Craig had dared him to never have pubes. I think it was because Dayle was the first to get them and Craig was jealous. Every week he has to pull the front of his shorts down to show that he's still cleanly shaven. No need to do that this week.

"Move back a sec." Shuffling back on my knees, I look up to Dayle. Hoping he's changed his mind.

However, no luck. Reaching to the bottom of his shirt, he pulls it over his head. Revealing his slim, pale, hairless body. Though, being this close I can make out some light abs. There's also a bit of definition in his pecks. Looking at his chest, I also notice his dark nipples. Given full access to look at his body, I also notice the beginning of a tan on his arms and legs, which while they haven't been shaved still only have a light dusting of hair on them. Different to my own hairy legs

He also takes the opportunity to kick off his shorts and underwear, sitting back down completely naked.

Holding his dick up in his right hand, he beckons me towards him with his left index finger. Shuffling back to him, I hesitate. My entire body rejects what I'm about to do. Telling myself over and over again that I'm not gay and that I shouldn't be doing this. Though, I shouldn't have done many of the dares I've done.

"Here, how about you start by licking my balls?" Dayle pulls back his cock, giving me full access to the hairless eggs in their wrinkled pouch.

Okay, Ty. Just treat this as any other dare. Once you've done it no one will say anything and definitely not tease you about it. It's just another dare.

Closing my eyes, I stick out my tongue and move forward. Making contact with the skin I give them a lick, the bumpy, wrinkled texture making it impossible to think it's anything other than a ball sack that I'm licking.

Giving them a few licks, the saltiness is heavier here. There's also another taste that wasn't present when licking his feet. Something I can't put my finger on.

"Good, no go lower." Dayle's voice is barely above a whisper as he lifts his balls, revealing a much hairier taint. I guess, Craigs never thought about checking here.

Licking the skin below his balls, I can feel the hairs rubbing against my tongue. That, along with the taste being more pungent here, has me doing everything I can to keep my face down between his legs. The musky smell of sweat and ball funk filling my nostrils as heat radiates from his undercarriage. There's also a clamminess that makes the experience pretty unpleasant. Maybe I should have just sucked him off. Could have skipped this step.

The licks are soft but seem to be doing the trick as Dayle gives a long sigh.

"Now, lower." Dayle lifts his legs onto the sofa, revealing his hairy butt hole.

"Come on, dude! I'm not licking your hole!" I don't move my face as Dayle's manly musk fills my head. Opening my eyes, his pink hole is like a beacon from within the dark brown forest.

"Just one -slow- lick. I swear, I'm already close. It won't be much longer." Looking up past the hair and balls, I can tell Dayle's jerking himself.

Deciding it's best to just get this over with, I close my eyes once again and lean my face down. Sticking my tongue out, I jump back as it hits wrinkled skin. Opening my eyes, I realise I'm much closer than I thought.

Readjusting, I go back to it. Starting from the bottom I slowly drag my tongue over the pink, puckered hole. My nose scrunches up as the sharp taste hits me. The feel of the coarse hairs making this the weirdest experience. Girls don't have hairy butt holes.

I feel Dayle's body shake as his jerking gets faster and a quiet moan escapes his lips.

Getting to the top of the wrinkled ring, I pull my head back and Dayle lets his legs relax, his feet once again resting against the floor.

Dayle's face is flushed as he continues to slowly work his big dick.

"Okay, now just put the head in and suck on it." His voice is ragged and breathy.

Without argument, I lean over and put his cock head in my mouth and close my lips around it. My lips feel the hardness of the shaft, while I probe the soft, spongy head with my tongue. Dayle gives a loud moan as his hand speeds up on his shaft.

"That's it. Lick the head. Bob up and down." Talking between gasps, it's obvious he's enjoying this as his cock throbs in my mouth. I follow Dayle's orders, getting a drop of precum that I quickly swallow, noticing the lack of taste, just a thick texture.

"Yeah, Ty, keep going. That's it." I can feel Dayle's body trembling through the chair as I take the head and an inch of the shaft in my mouth.

"Okay, Ty. For the last part of the dare. Swallow my load." Before I'm able to remove my mouth from his cock, Dayle's left-hand presses on the back of my head. Not overly forceful, but enough to stop me from rising up. Which is probably for the best. If I fail the dare now, what was the point of all this?

"Uh, yeah, yeah, fuuuuuuuuuuck!" With whimpers and groans, Dayle's hand continues jerking his shaft as the first shots of cum erupt from his cock slit.

The first shot splits into two, part of it hitting my tongue, the other going straight down my throat making me gag. Dayle's hand on my head stays rigid, stopping me from moving.

The second shot does the same, however, this time the cum that lands on my tongue is much thicker and the shot that goes down my throat weaker.

Thankfully, the next 5 shots just land on my tongue. I try to swallow the thick goo as my throat muscles clench, trying to cough it back up.

Fully satisfied, Dayle releases his hold on my head, allowing me to pull away from him. I continue to try and swallow the cum in my mouth - not wanting to fail the dare - however, with the choking it was very difficult. I'm pretty sure some ended up coming out of my nose, leaving a burn and the smell of bleach. Thankfully, most of it went down my throat. An acrid, taste of nothing really. A bit salty. The worst part was how thick and gooey it was.

"Not finished yet, dude." Dayle's voice sounds sleepy as he points at the cum now trickling down his shaft, mixing with my saliva and the cum I'd coughed up while still stuck on his cock.

Giving Dayle my death glare, I grab his shaft and shove a good 5 inches into my mouth, sucking the last of the nasty goo down. I'm tired of this and just want it to be over.

The dare over, I quickly take my place back in front of Craig. There's no need to ask if the dare was satisfactory. I know it was. I'm not sure if I'm more pissed at having to suck Dayle's dick or the fact I won't be able to kick it. Or maybe it's that Dayle's cocky attitude might have a solid basis in the size of his cock. For a moment there I thought I'd had him beat on cock size.

Dayle stayed naked for a little longer before getting his clothes back on and joining us in a few games of smash. As is usual, no one said anything about the dare. No teasing. No mocking. No calling me a cocksucker, queer or fag. We just continued as usual. Well, except I refused to have much to do with Dayle the rest of the afternoon.

A couple of hours later, Dale got a call from his mum. Apparently, they'd found the perfect suit and needed him to go try it on. I've no idea why it's taking them so long to find a suit. I imagine he'd look good in one.

Me and Lewis stayed at Craig's until his mum came home at 10. It's not that she doesn't like us, it's just that she doesn't want us in the house at the same time as her. She didn't kick us out, but the less than enthused greeting and informing us of her desire for a bath and quiet was a pretty big hint.

"You fucked up, you know?" Walking home with Lewis, we'd mostly been quiet until the accusation.

"How?" Shit, is he saying that sucking Dayle's dick was a mistake? Do they hate me now? Think I'm some sick pervert?

"Being such a baby about the dare." Oh. So the opposite. I should have been more enthusiastic about sucking another dude's dick?

"What? I was supposed to just be okay with sucking on a dude's dick?" I turn to look at Lewis's soft features. His light, coppery brown hair glints in the street light. His fringe swept to the left, just skimming the top of his eyebrow as it settles next to his ear.

"Yeah. Like every other dare, dude." I don't have an answer for that one. "Now, we all know where your limits are. We know how to get to you." His usually heavy-lidded, sleepy eyes widened with excitement.

He was right. We all revelled in finding each other's lines and making them cross them and I'd just demonstrated that sex was mine. Shit.

"Anyway, see you at school tomorrow." I just limply waved as my mind filled with possible dares I'd get in the future.

Fuck.

If you've enjoyed feel free to drop me a message at: bootusrim@gmail.com. Also check out my other stories:

https://www.nifty.org/nifty/gay/adult-youth/the-morality-of-cheating

https://www.nifty.org/nifty/gay/adult-friends/desperate-times/

https://www.nifty.org/nifty/gay/encounters/i-aint-gay/

https://www.nifty.org/nifty/gay/sf-fantasy/might-and-magic

https://www.nifty.org/nifty/gay/encounters/pretty-boy-and-the-pauper

Next: Chapter 2


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