This is my first story, please feel free to leave comments or suggestions. Feel free to message me as well, enjoy.
**All characters are 18**
This is a work of fiction
Mike and Josh were the best of friends growing up, they came from the same small well-to-do town in the Midwestern United States. Both friends were very athletic which in turn made them very competitive. It was always about who could run the fastest, jump the highest, and lift the heaviest object. As they got older this spilled over into sports, they played them all, Baseball, Soccer, Basketball, and Football. It was always about who got to be the team captain, who had the highest batting average, or who scored the most points/goals in a season.
As they grew older girls became a bigger part of this competition in middle school. They were determined not to let a girl come between them so they made a pact, neither would ever steal a girl, but until the first kiss, it was all fair game. Being the popular kids they went through their share of chicks always a conquest to show the other one up. That was until late freshman year when Josh’s dad got in some pretty serious legal troubles, something called insider trading that neither of the boys really understood.
It was a whirlwind at the end of Josh’s freshman year, his dad took a plea deal to keep from doing the max, but that meant 5 years of jail time leaving Josh and his mother to fend for themselves. The Feds required them to sell their house to pay some of the money he stole back, this forced Josh and his mom to move away from their well-to-do neighborhood to the city in some low-income house. This also forced Josh into a new school, and most of his old friends and even Mike looked down on him for that. Turns out part of what his dad did cost a lot of his friend’s parents some money, and Mike’s parents lost a lot.
So Josh wound up with a new school, a rougher inner-city school. He never saw any of his old friends from his old life, so he had to rebuild himself. He leaned heavily on his athletic ability and was soon with the in-crowd at the new school. This led him to a new set of girls, they were on the rougher side but still got the job done for a young teen.
Flash forward to senior year, both Josh and Mike are the star quarterback on their football teams, on a collision course for the state championship game. Josh reaches out to Mike for the first time in years with a wager for the game. Josh, with nothing to lose offers up his girlfriend Shea, but only if Mike offers up Emily, his longtime girlfriend.
Shea and Josh have been dating a few months, she is a thick busty black girl, 38DD, with thunder thighs and a bubble butt, the kind you see twerking in those music videos. Emily and Mike had been dating for a few years, she was the typical All-American Barbie, cheerleader, 32B, flat tummy, tight ass, fit from hours of expensive fitness classes every week.
Mike could not believe the message, this had to be a joke, Josh’s team was major underdogs in the game, but could he really risk Emily? He has always wanted to be with a black girl. Mike soon found himself on Shea’s Instagram scrolling through her pics, most of them showing off her massive tits or her thick ass. Shea definitely wasn’t shy. Mike couldn’t believe how hard he got from these pics and closed the app and tried not to think about the wager and Shea. Mike had some wild dreams that night, about black girls, and mostly about Shea, he woke up with raging morning wood that only took 2 pumps for him to make a mess in his boxers. Before Mike even cleaned up, he grabbed his phone and sent Josh a one-word replay…”DEAL”
Three days later Mike and Josh walk to the center of the field for the coin flip to kick off the game. The two boys looking at each other, knowing a lot more is on the line than the State Trophy. Josh’s team wins the coin flip but that is about all they on in the first half, as Mike’s Knights take a commanding lead at halftime, up 28-7. Mike is pretty happy with himself at halftime, thinking of the new experience he is going to have after the game and how much fun it’s going to be to play with Shea’s big tits and slap her fat ass.
After halftime the tables turned hard, Josh’s Tigers looked like a new team, a team on a mission. Mike watches as his team seems to make every mistake, led by Mike’s 3 interceptions. As the clock ticks down there is nothing Mike can do as the Tigers run out the clock, final score Tigers 42, Knights 35.
As the teams shook hands, Josh tells Mike “meet you in the old locker rooms in 30 minutes, if you bail the Tigers a going to come looking for you, and you may not walk away from it!”
Josh went off to the locker room to wait for his prize thinking Mike would welch on the deal but hoping deep down he would show with Emily. He stripped down to his padded compression shorts that outlined his thick bulge quite nicely, at least that’s what Shea always told him. As he sat on the bench waiting, losing hope he heard the door open and he stood up.
Much to Josh’s surprise in walks Mike with Emily in tow, they are both greeted with Josh wearing just his compression shorts and an ear-to-ear grin. “Hey, Emily… it’s been a while huh?” Josh says as Emily stands there in semi shock, the guy she used to know has changed, he is ripped from head to toe, the sweat from the game glistens on his body and the compression shorts leave little to the imagination.
Emily turns to Mike “What is going on here?!” Mike on the verge of tears explains to the girl he loves, the terrible bet he made, how stupid it was and how sorry he was, as Emily stands there in shock, not believing it until she turns and sees the look of animalistic lust on Josh’s face. Her only response is “no no no this cannot be happening” Josh responds with “Mike, you know the other option here” Mike turns to Emily “His whole team will beat me probably to death if you don’t do this, I’m so sorry Em!”
Emily still in shock at this turn of events mutters out “fine” trying to act tough, but both of the boys knowing that she is scared of what’s to come.
“Mike, before we get started have a seat” Josh orders, Mike unsure of why sits on the end of the bench, and before he can react Josh has a zip tie around a wrist and around the steel leg of the bench “There we go, I don’t want any funny business from you” Josh says as he pats Mike on the cheek. Josh then turns to Emily “Well baby, why don’t you strip that cheer uniform off…you won’t be needing that tonight” he says with a chuckle.
Emily with tears in her eyes can’t look either of the boys in the eyes, Mike, out of disgust for the deal he made and Josh out of fear of what’s to come, she has seen him start to grow in his shorts and he is already bigger and thicker the Mike is. As if she is accepting her fate she moves back to Mike and squats down to have Mike unzip her cheer uniform. Mike whispers “I’m so sorry baby” as he reaches up with his free hand and pulls the zipper down from her neck to her lower back exposing her shoulders and her white sports bra.
Josh grins with excitement as Emily steps forward, putting on a tough face as she pulls the left shoulder of the uniform and then the right down, exposing her sports bra and tight tan tummy to the eager Josh. Josh notices how perky her tits look, and how he can just make out the little bumps her nipples are making as they start to harden.
As Emily’s uniform falls past her hips revealing her tight white bloomers she looks up to see the still growing bulge in Josh’s shorts, she quickly looks away with a gulp. Mike can’t help but stare at it too, knowing it’s already bigger than he is, knowing that might be a problem for Emily, as Mike was her first and only partner, until now.
Josh breaks the silence “damn she’s a dime piece huh Mike?” giving Mike a wink. “Alright Emily, let’s see those tits!” Josh says looking right at her. Emily, seeming to accept her fate lowers her head slightly, crosses her arms grabbing the sides of her bra, and pulls it up over her head exposing her perky B’s to Josh, the second guy to ever see them. “Wow Emily, those are perfect, and are you nips already hard baby?” Josh says with a grin. Emily doesn’t respond, just lowers her head farther.
“Time to get to work Emily” Josh orders as he nods down to the ground, Emily plays dumb, she hates giving Mike blow jobs, it’s a special occasion kind of thing. “Emily, knees sweetie!” Josh says in a stern voice. Emily takes a deep breath and kneels down in front of Josh, looking up, somewhat intimidated by the large tent now in front of her face.
Sheepishly Emily reaches her hands up and grasps the elastic of his compression shorts, the smell of his sweat and musk fill her nose. Josh grins looking down and her and mutters “go ahead, baby”. Emily starts to slide them down, pulling them over his bulge and then down. She gasps and falls back when his 8.5 inches springs out barely missing her face. She hears Mike behind her on the bench mutter “Jesus” as it comes into view. Emily swallows a big lump in her throat as she reaches a hand up and starts to stroke Josh’s massive cock, the biggest she had ever seen even in the few porn videos Mike had her watch.
Josh moans with approval as she strokes laughing to himself at both of their reaction to his size. He has never seen Mike’s cock but knows he has him beat in the size department by quite a bit. “Come on baby it won’t bite” Josh says as he takes half a step forward his cock less than an inch from Emily’s pretty face. Emily looks up with a defeated look and slowly parts her lips as Josh puts the tip in her mouth. Emily has to fight the urge to gag not wanting to give Josh the satisfaction. The fact that she hates giving head and the taste of his sweaty cock is almost too much. She wants to pull off is even thinking about it when she feels Josh’s hand on her head. Her eyes widen as he starts to pull her in with a fist full of hair, her cheeks swell as she takes the first inch of his rock-hard cock. She can feel the bulging veins as they slide past her lips and into her mouth.
Emily instinctively places her hands on Josh’s sweaty thighs to hopefully slow his cocks advance but he easily overpowers her attempt and keeps sliding more of his cock in. He starts to work up a slow rhythm as Emily starts to drool out the side of her mouth dropping down onto her perky tits. Emily’s eyes water as Josh feeds more of his cock in her mouth as she fights the urge to gag. As Josh gets about half his cock in she gags and tries to pull off, but Josh holds her hair firm and keeps her on his cock.
Josh looks up at Mike who is watching intently. “ She’s gagging on 4 inches old buddy is that all your are packing? Josh says as he laughs, Mike just glared at him not being able to think of a witty response since it’s mostly true.
Josh let’s go of Emily’s hair “show me how you suck Mike off” he orders Emily with a grin as he brushes the hair off her face. Emily pulls off of his cock as her drool hangs off of it, taking a second to catch her breath. She takes a deep breath and then puts his cock back in her mouth. Just then a thought creeps into her head ‘if I make him cum maybe he won’t fuck me, I know that cock is gonna hurt’
Emily quickly gets to work with her new plan, she only works on 2 or 3 inches of his cock not wanting to gag anymore. She quickens her pace and uses all the tongue tricks she learned to try to get Mike off quickly the next time he asks for a bj. Mike looks on in shock as she sucks Josh’s big cock in ways she has never sucked his.
Josh enjoys this treatment for a minute or two and then pulls back from Emily his cock leaving with a pop as she tries to suck up all the drool to keep as much as she can of her perky tits. She tries to lean on to Josh’s cock again to finish her plan. “As much as I was loving the head baby it’s time for more fun” Josh grins at Emily as a look of defeat rushes over her face as she knows her plan was foiled. Josh nods to the bench Mike is tied to “ hop up Em”
Emily sits on the bench in front of Josh. Josh leans into her grabbing both of her tits with a firm squeeze and he pushes her back on the bench. Her head is not too far from Mike’s crotch where Josh notices a bit of a tent. Josh wastes little time as he hooks both his thumbs under the waistband of Emily’s bloomers and quickly pulls them down revealing a freshly waxed slit that glistens with wetness. Josh grins as he tosses the bloomers into Mike’s lap landing them on his tent. Josh quickly moves into position between Emily’s legs with his cock looming over her.
Emily looks up and Josh and pleads with him ” please go slowly, you are like really big” embarrassing Mike in the process. Josh grins as he runs the tip of his cock up and down her slit, making sure Mike hears how wet her pussy is. Josh slowly applies pressure and he pushes the tip into Emily as she gasps. She bits her lip and closes her eyes fighting back the tears as Josh pushes his big cock into her tight hole. She winces in pain as Josh starts to quicken the pace, going faster and deeper into her. Emily’s tits are bouncing and the bench is shaking under them.
Josh keeps on fucking Emily for about 5 minutes, Emily is starting to almost enjoy the big cock buried in her when Josh stops and pulls out. “Em, flip over I want to do doggie”. Emily objects, her and Mike only do missionary she is worried doggie will hurt more. Josh losing patience grabs onto her leg with his strong hands and fips her over. She lands hard on her tits, the inside of one of her legs slamming into the bench as she grunts. As she looks up, she sees the tent in her boyfriend’s pants right in front of her, she cannot believe he is getting turned on watching his girlfriend get used like this.
Josh spread Emily’s legs and then grabs a fist full of hair forcing her to arch her back as she gasps. Josh whispers “I know it was your Dad that used my Dad as the fall guy to the Feds” Emily is shocked, she opens her mouth to protest or apologize but before she can Josh slams his cock into her virgin asshole. Her words are replaced with a scream as the pain hits her. She never let Mike do anal even with his much smaller cock, she had only tried a finger a time or two but that always hurt. Now she is trapped between the bench and a massive cock pushing into her tight little hole.
Josh keeps pushing, going deeper and harder into her asshole as she screams and cries, he doesn’t care, this is his own little payback for his dad’s sake as he keeps fucking. Forcing his cock deeper into her tight little hole he can feel it gripping the shaft tightly. He keeps pounding getting closer and closer to the edge. Jake lets out a grunt as he makes a few last hard thrusts and then pulls out. He gives his cock a few quick strokes and then shoots a massive load all over Emily’s ass, back, and hair, some even spraying onto Mike much to his dismay.
“Oh shit” Josh blurts out as he cums. Mike, already pissed that he got spayed “Let me go jackass, let me comfort her” As if almost on cue, all 3 of them hear a commotion in the hallway, as Josh says “just on time” Mike looks up, “what the fuck is that?” Josh grins and says” how do you think I rallied my team at halftime? I told them they got a piece of the head cheerleader if we won”
END
Source: reddit.com/r/Erotica/comments/pew5w0/a_bet_gone_wrong_2400_words