The DILF Bet

 

Vince had been an avid football fan since he had accidentally stumbled upon clips on YouTube in highschool when a search for ‘football shocking last minute upsets’ bought up videos from a World Cup, which features a sport most Americans like himself would not have called ‘football’. Lucky for Vince, the linguistic quirk was a blessing in disguise and he quickly became a super fan.

Vince had been excited for the 2022 World Cup for months so was surprised when his dad Mike had suggested he’d throw a viewing party with his college buddy Nolan. Neither Nolan or Mike knew the first thing about the sport. However, Mike had found himself swept up in his son’s growing excitement, plus he hadn’t hung out properly with his good mate in some time and his wife was going to be out of town the day of the match so - regardless of genuine interest in the World Cup - it was the perfect opportunity to get drunk, cheer at sports (an American pass time regardless of sport) and throw in some bonding time with his son.

Though Vince fancied Belgium, who wasn’t playing this particular match, the two goofy man-children on the couch had chosen the team to cheer for seemingly at random, literally basing their decisions on their color preference of the team’s uniforms. Mike had picked one team and a jocular Nolan, always the contrarian, had picked the other. After thirty minutes of no scoring in the match, but lots of drinking by the two men, Nolan stood up during a commercial break and made a sophomoric bet.

“If my team loses, you can kick me in the nuts... “ 

He pretended to count on his fingers, “Fifty times!” 

It wasn’t a random number; Nolan had just turned fifty and his version of a midlife crisis meant leaning even harder into his juvenile tendencies in an attempt to fight back the hands of time. Time, as it always does, was winning. Even though Nolan’s body still rivaled even twenty-somethings under his shirt, he was starting to feel the time slipping away, all the more reason he jumped at the chance to just hang out in Mike’s basement and pretend that they were young again. Mike’s bar stocked with premium liquor and his fabulous 80” television with immerse surround sound was an added bonus.

Mike roared with laughter as the usually-buttoned up Nolan threw back another shot of vodka before lifting his shirt and striking a victory pose he imagined the scoring player on his chosen team would eventually make. Nolan was in much better shape than Mike due to his near obsession with the gym and serendipitous genes, but he wasn’t showing off. He was genuinely just being goofy but the brief glimpse of Nolan’s rippled, fuzzy abs got Vince excited. He awkwardly shifted his popcorn bowl to hide the bulge growing in his shorts.

As the game neared its end, Vince was offered drinks every time his father or Nolan went to the bar for a refill, but declined.

“I’m only twenty, so I’m underage,” he said politely to Nolan as he headed to grab yet another beer.

Nolan noticed that Vince was blushing uncontrollably, and though he was tempted to poke good-humored fun, he remembered he was the literal adult in the situation so took the mature route and ignored it.

“Right, only twenty. But it’s the World Cup and most of these countries have a drinking age of 18 so...”

“Stop corrupting my son, Nolan!” Mike laughed, “That’s my wife's job!” 

Everyone erupted into laughter just as the game took a sudden turn.

Nolan sat at the bar holding a half-empty beer, draped in the flag of his team, his gaze fixated on the giant screen in front of him as he shouted out totally random advice at the players on the screen. The final moments of the match slipped away and at the absolute last moment there was a goal. The stadium, and pubs around the globe, exploded into cheers and groans. The final buzzer marked the end of the match.

“What the fuck was that!?” Mike screamed in excitement.

“Are you kidding me!” Vince, the only actual football enthusiast in the room, frantically rewound the scene to watch the miracle kick over and over. Even though Vince's dad and Nolan didn’t fully grasp the technical aspects of the shocking win, they couldn’t help but be swept up in the moment. 

“Not going to lie, I didn’t; know what I was watching most of the time but that was awesome!” Mike said with zero sarcasm, the slurring forty-seven year old heading to the bar for a refill.

Vince continued to sip on his soda chuckling in bemusement as the two middle aged men jumped around and cheered and did celebratory tequila shots.

“See, dad! I told you you’d like it.”

Mike smiled warmly. He had actually enjoyed watching the match with his friend and his son even if the World Cup hadn’t been top on his list of priorities.

“You did say I’d like it! I love you, Vince!”

Mike stammered over to Vince and gave him a big hug, practically pinning his still-sitting son to the recliner. 

The three men stood around talking about the match, everyone but Vince just repeating the announcer’s analysis in an attempt to sound smart on the subject. Suddenly Mike jabbed Nolan in his chest with his pudgy finger and couldn’t help but nod in honest admiration at Nolan’s rock-hard abs. But that didn’t take away from the momentous announcement he was about to make.

“Hey! Don’t forget, Nolan, you said you’d take fifty to the bag if your team lost... and they just lost!” Mike roared. 

Nolan blushed and his hand hovered instinctively over the front of his jeans.

“I mean, I was just being silly. I was drunk...” Nolan stammered.

Mike only gave a telling smile as he took a step closer to his buddy.

Vince looked on quizzically as his dad stepped forward, sometimes stumbling, until he was face to face with Nolan secretly wishing he was in his dad’s place. 

“So? Are you going to pay up?” Mike laughed.

Nolan winced as his inebriated friend reached out and clutched the bulge in his jeans. Vince’s cock twitched at the site of his long-time, DILF crush having his goods grabbed, even if it was by his own father.

Nolan gulped and tried to take a step back but Mike’s surprisingly strong grip on his boys only made him wince. The two middle-aged men stood in silence for a moment, almost forgetting another young man - Mike’s son - was still watching.

Mike, whose alcohol fueled brain suddenly became aware that his son was watching, released the huge bulge in his hands and smiled. Mike wasn’t nearly as ripped as Nolan but his job as a construction worker meant he still had a decent amount of physical strength. Vince could feel a weird tension building so wanted to call an end before things got weird.

“Hey guys, you both literally randomly picked teams. My dad just got lucky! Why don’t you just forget about the stupid bet?”

Vince finished his self righteous speech without being able to pull his gaze away from the bulge in Nolan’s crotch. Vince had been hard ever since Nolan had shown off his body in his boastful dance.

Mike laughed as he went to the bar and poured three shots of premium tequila. He returned and handed one to his buddy Nolan and his son.

Vince grimaced at the site of it and the look suddenly reinforced the fact that Mike was a dad. He snatched the shot glass from his son and handed it to Nolan.

“Bottom’s up!”

Vince snickered as he watched his dad and his crush getting more and more drunk. Just seeing Nolan, a usually conservative DILF, showing off his body, drinking and acting half his age was getting Vince rock hard. Nolan, and Mike, noticed.  Although Vince thought he wasn’t obvious, it wasn’t a secret to his dad or Nolan that Vince had a crush on Nolan, his father’s bestie and family friend, since highschool.

After a bit more chatting and laughter, Mike made a random, drunk proclamation, “Actually, son, I think Nolan oughta pay up. It would be a good life lesson on keeping your word... or something,”

Vince gulped as his eyes darted to the bulge in Nolan’s jeans.

“So was that fifty kicks total or fifty kicks from each of us?” Mike laughed.

Mike wrapped his arm around his son’s shoulder as he playfully poked Nolan’s pec with his free hand.

“Dad!” Vince recoiled in feigned disgust. He wasn’t so much grossed out at his dad’s toilet humor than the fact that the conversation was revolving around Nolan’s package; the same package Vince had spent years dreaming about.

Nolan took another sip of his drink before taking a wide-footed stance, as if he was just waiting to be kicked.

“I guess fifty each!” Nolan shrugged. Alcohol is often called liquid courage and it couldn’t have been a more appropriate moniker in this situation. Nolan knew he was a stud, and often showed off in the gym locker room. He knew he was strong. He knew he was tough. And now he was feeling cocky enough to literally put his balls on the line against his dad-bod best friend and his scrawny son.

Before Vince could change the topic, his dad smiled and chortled “Okay man, it’s your funeral!”

Mike reared back his foot and sent it sailing between his friend’s beefy legs. Nolan winced slightly at the less than powerful kick. Mike had been more focused on not spilling his drink than actually hurting Nolan so the well-aimed kick barely connected. 

Nolan collapsed to the ground clutching his jeans-clad balls faking fits of hysterics. Mike laughed as he helped his friend back to his feet as if he had taken a truly devastating blow. The theatrics were adorable and Vince almost forgot he was watching men in their late forties and early fifties, one of which was his dad.

“Okay, your turn!” Nolan chuckled and he put his hands behind his back and resumed a spread-legged stance.

Vince tried to joke his way out of the increasingly off-the-rails situation but his inebriated dad and Nolan were able to coax him into playing along. Vince gave Nolan’s balls a half-hearted kick. Whereas Mike’s first kick had been weak from a combination of alcohol-induced inattention, Vince was willing himself not to unleash his full strength. With his clothes on the twenty-year-old Vince still looked like a scrawny high schooler, but in actuality he was a ripped, svelte young man who was as adept at streaming on Twitch as he was hitting the gym and his accelerated metabolism only helped him keep off fat.

Nolan barely winced as Mike and his son let out a few more playful kicks. Nolan could tell his best friend and his son were holding out, and his earlier tequila shots were clouding his judgment so he spread his legs wider. He was starting to get hot so ditched the flag and scarf he had been wearing, then his sweater until he was only wearing jeans and a T-shirt. Vince’s mouth was watering but his dad and Mike were totally obvious to how turned on the young man was getting.

“Oh, I’m sorry, I didn’t realize two sorority girls were invited. These kicks are so weak!” Nolan roared in laughter.

Mike acted offended, though his smile made it obvious he was joking, as he unleashed his first true kick. He wasn’t as fit as Nolan and especially not as fit as his son, but he was strong enough to do some real damage with his kicks if he wanted to. Nolan’s eyes crossed and he clutched his bulging nuts. Mike and Vince laughed as if Nolan was still joking but the handsome daddy wasn’t kidding. He had been totally taken aback by the impact of Mike’s shoe colliding with his junk in the game’s first sincere, actual kick that wasn’t just played for laughs.

Vince was up next and unleashed a devastating blow to his crush’s groin, his own cock twitching as he felt Nolan’s meaty bulge deform under the blow. Nolan pretended to laugh off the pain and stood again with his arms behind his back, legs spread, bulge on full display. Mike had seen Nolan naked dozens of times over the years so new his DILF friend was packing an extremely hefty set of sperm pods, though they were smaller than the monster pair of nuts Vince had always imagined Nolan having.

Father and son took alternating turns on Nolan’s bulge until, after Mike’s fifteenth kick, Nolan’s eyes crossed and he slumped to his knees clutching his sore nuts through his jeans. In that position he just happened to be eye-to-eye with Vince and Mike’s crotches and Vince couldn’t help but imagine the hunky man ripping open both their jeans and going to town with his mouth. Afterall, he had seen porn where father-son pairs had tag-teamed some bimbo, so why not swap out the woman with Nolan?

After Nolan got to his feet, Vince grabbed his shoulders and slammed his knee into Nolan’s jeans, feeling the beefy bulge flatten from the impact. Nolan gasped and reached out for Vince’s shoulders for support. Vince was aroused - and alarmed - by the studly man’s reaction.

“My turn!”

CRUNCH

Mike wasted no time kicking Nolan’s balls so hard that Mike’s leg ached. It reminded him of their crazy roshambo games in college.

“Hey fellas, I may need a break,”

Nolan laughed to cover the increasing pain in his groin. He and Mike headed to the bar for another drink and Vince stood there barely trying to conceal his boner. He had been hard nearly the entire game so it was too late to hide anyway.

Nolan took the next twenty blows - ten per kicker - like a champ thanks to a combination of true bravado, alcohol and a playful need to ‘win’ the silly game he was was playing with his best friend Mike.

Vince opted to use another knee for his thirty-seventh turn. It has hard. Really hard.

Really, really hard.

Vince instantly felt terrible as he watched Nolan’s eyes roll into his head as he screamed, a genuine, pained scream, and collapsed to the ground. Mike chuckled, holding a beer, as he watched Nolan fall. He knew him and his son weren’t really going to hurt Nolan... on purpose at least.

“Mr. Matson!” 

Vince dropped to his knees to make eye contact with the writhing stud. Vince’s cock twitched as he helped Nolan to the couch.

“Aww, does the baby need an ice pack?” Mike joked.

Vince cut his drunk dad a look of annoyance.

Nolan jumped to his feet and approached Mike and for a moment Vince thought the two were going to fight. Instead Nolan let out a deep laugh and gave his friend a bear hug and a kiss on the cheek. Vince had never seen his father kissed, even on the cheek, by another man and was relieved that his one-hundred percent straight dad didn’t have an unhelpful reaction. Instead, Mike laughed and gave Nolan a peck on the forehead. 

“Okay, no holds barred, I guess, since these are the final kicks!” 

Nolan had grossly underestimated how many more kicks he had agreed to. Both mike and Vince had over ten each.

Unfortunately for Nolan, Mike’s thirty-eighth kick hit a nerve. Literally. Nolan felt like Mike’s shoe was going to keep crushing into his jeans until his swelling right nut literally burst. His eyes bugged out as he again slumped to the ground clutching his crotch. Only this time he couldn’t joke his way out of the tears running down his face, an automatic reaction to the nut crushing blows.

Mike laughed but Vince was genuinely concerned, especially after Nolan swatted again his hand when he tried to help him up. Nolan was in real pain; Vince was naturally stronger than he looked - and wasn’t holding back at this point - and Mike was too intoxicated to regulate his kicks. They had stopped being friendly roshambo blows and were now full-force, membrane warping blows. And Nolan was too drunk to fully register the severity of the situation, letting his ego and the overall good vibes force him to take blow after blow.

Vince, the only sober one in the bunch, could tell that Nolan was in serious pain, and maybe being injured despite the levity. The last thing he wanted was to hurt Nolan, his dad’s bestie and a friend to the family from before Vince was born.

“Mr. Matson, lemme’ get you some ice..” Vince started.

Nolan chuckled through gritted teeth.

“No, I’m fine,”

Nolan went to stand but was stricken with pain. That’s it, Vince thought.

“Okay, guys. Funs over!” Vince said in a serious tone but trying to laugh it off.

Nolan wasn’t having it. Despite the pain, he was still too sauced up to think straight. He was a stud, afterall. He could take some kicks from his dad-body buddy and a scrawny twenty-year old. 

“I’m fine! Look!”

Nolan stood up and pulled his jeans to his ankles before kicking them off with a flourish. Vince licked his lips instinctively as he drank in the sight of Nolan’s over-stuffed briefs. It looked like someone was smuggling two jumbo hen’s eggs in them. Meanwhile Nolan was getting hot from pain so casually peeled off his shirt too. He was now standing just in his tight underwear, his chest glistening with sweat. Vince’s heart was pounding.

Mike respectively pretended not to notice how turned on Vince was getting and was grateful how classy Nolan was being just treating the whole event as ‘bros being bros’ instead of making a joke out of Vince’s increasingly aroused state. 

On Mike’s fortieth kick Nolan dropped to the ground. And stayed there. He was grasping his swollen nuts and gasping. Mike and his son weren’t holding back at this point and he knew he still had a combined twenty more kicks. His nuts felt like they were going to explode despite the fact they were far from real danger. Fifty years of experience had taught him it took more than a few dozen kicks to actually pop a testicle. Vince, however, didn't’ know any better and was convinced he and his father were doing actual damage to Mr. Matson’s crotch Nolan stood up, arms obediently behind his back and braced for Vince’s kick.

“What are you waiting for, son? It’s your turn?” Mike encouraged; he’d been impressed at the powerful kicks Vince was delivering. Powerful impacts that filled the basement with their loud echoing crunches. 

“I think Mr. Matson’s had enough, dad. This is getting out of..."

Mike didn’t let his concerned son finish his thought before he reached out and pulled Nolan’s underwear to his feet. Vince was mortified as his cock twitched in his jeans; Nolan was totally naked and ridiculously hot, much hotter than Vince had ever imagined all the times he had wanked off thinking about him. His swollen nuts were bigger and puffier than normal, red and hanging quite low after they were freed from his underwear. Above them his completely flaccid cock was an astonishing six inches and thick and Vince couldn’t help but imagine how big it would get fully hard. Vince’s cock was throbbing, his heart was racing and he was finding it hard to focus on the game. Nolan picked up on how uncomfortable Vince was getting and bent down to pull up his shorts but Mike stopped him.

“What? We’re all guys here, just a couple of bros. A couple of drunk bros!” Mike laughed as he grabbed Nolan’s underwear, not letting go until Nolan reluctantly stepped out of them and they were tossed across the room.

Mike and Nolan had been friends literally longer than they could remember so Mike had no qualms about teasing his naked gay friend and was totally comfortable with his clearly enamored son having a chance to sneak a peek. Vince wasn’t feeling so progressive and his hands were getting clammy as the reality of the situation collided with his fantasy... though he was still rock hard.

Nolan chuckled.

“It’s okay, Vince. They’re fine, see?”

Nolan took one of his large nuts in each hand and gave them a playful squeeze, doing his best to disguise his wincing. 

“So, by my count, we each have ten more kicks left,” Mike sneered. 

From the outside it may have looked as if Mike was being menacing but Nolan had known Mike too long and they both burst out laughing.

Mike took a running start for this forty-first kick, nearly launching his hunky friend off his feet on impact.

“Fuck, man!”

Nolan struggled to stay upright.

Vince figured he would just give Nolan another knee. He grabbed Nolan’s shoulders for leverage but before he could strike his dad spat out a joke.

“Don’t worry, Vince. Guys like him don’t want kids anyway!”

Vince, his arms still around Nolan’s shoulder, turned to his father in disgust.

“Guys like him? Like him? You mean, like me? Gay? You meant gay, right?”

Nolan’s heart sank. Mike stammered for a response. He actually hadn’t meant that at all. Mike’s comment was a drunken jab at Nolan’s Devil-may-care, go-it-alone attitude and not any kind of veiled insult. Mike’s face flushed red, he was so embarrassed he didn’t know what to say.

Suddenly Vince burst out laughing. He’d finally succeeded in making the two of them feel almost as awkward as he felt and smiled smugly as he became ‘one of the guys’. His dad and Nolan had only just realized Vince had been feigning his indignation before Vince’s knee slammed into Nolan’s crotch with a disturbing, wet splat. 

Nolan’s eyes crossed and he would have collapsed to his knees if Vince hadn’t been holding him up. 

CRUNCH

CRUNCH 

Nolan’s deep screams made Vince nearly shoot his load as he slammed his kneed over and over into Nolan’s crotch, slamming his heavy balls into his pelvis until he had completed all fifty of his kicks, with a few extra. Vince had lost count. 

“Yeah, I don’t think Mr. Matson wants kids,”

Vince let Nolan slump slightly after the rapid fire knees but just before Nolan could fall to the ground Vince held him up, feeling Nolan’s sweaty chest against his as he whispered one more thing into Nolan’s ear.

“I really hope you don’t want kids, Mr. Matson,”

Nolan’s eyes crossed as he slumped to his knees, mildly disturbed by the indifference in Vince’s voice. Vince really didn’t want to actually hurt Nolan- or at least not unless his dad was on board. After all he was a close family friend, but the act of threatening him nearly made Vince blow his load by itself.

Mike gave his son a drunken high five.

“That’s my boy!”

Mike reached down and took one of Nolan’s ankles in each fist before rising to his feet. Mike looked down as his stud best friend, whose legs were wrenched into the air, leading down in a perfect V shape with Nolan’s fat, swollen balls at the intersection.

Nolan knew instantly what was about to happen and shouted - in genuine terror - begging. But a bet’s a bet, Mike thought.

CRUNCH

CRUNCH

CRUNCH

Nolan thought he was was going to vomit as Mike slammed his shoe down onto his bare nuts over and over, grinding each time. Nolan was certain Mike wasn’t trying to actually ruin him or anything, but Mike also wasn’t going easy on him as he stomped out the last ten or so of his turns.

Finally, Mike let Nolan’s legs go and the hunky man grabbed his balls and curled into a fetal position. Mike laughed but Vince was incredibly turned off at the site of the naked, muscular daddy on the ground.

It took Nolan a long time to compose himself enough to stand. His nuts were swollen and bruised and he was glad Mike and Vince were just playing a friendly - albeit unrestrained - game. He didn’t even want to imagine the outcome if the father-son team had actually been trying to really hurt him.

“Cover yourself up, idiot!” Mike roared in laughter as he threw Nolan’s underwear at his face.

Nolan rolled his eyes in comic annoyance, “Ugh, Mike you’re such a loser!” he laughed as he put his underwear on and rose to his feet. Even though the mood was jovial, Mike and Vince both winced, and were kind of turned on, at the look of pain on Nolan’s face as his swollen nuts were compressed by the fabric of his tight underwear. Nolan smiled trying to play off his autonomic response lest he make his best friend or his best friend’s son uncomfortable. 

At that moment Mike’s phone rang and he pulled it out of his pocket. 

Mike’s son and Nolan were impressed at how the clearly drunk DILF was able to sound totally sober over the brief conversation with someone who was clearly from Mike’s job. 

“... Yeah, I’ll send you the file right now. Gimme’ a bit.”

“I’ll be right back, duty calls.” Mike headed up the basement stairs to send whatever file his work colleague was asking about but before he disappeared up the stairs he shouted for Nolan to make him another cocktail.

Nolan headed to the bar, still only wearing his underwear, and Vince followed behind. As he made himself and Mike a drink Vince laughed.

“Wow, you two are tanks! You’ve been drinking all day!” 

Nolan smiled and winked “We’re very experienced,”

They made their way back to the couch. Nolan smiled as he eyed his best friend’s son up and down and Vince bit his lip at the site of the sweaty, busted stud. Finally Vince blurted out.

“Wow, Mr. Matson, you’re a DILF!” 

Nolan raised his eyebrow.

“I’m... umm.. I’m not a dad, Vince. But thanks! I don'ts want kids anyway,” 

Nolan took a sip of his drink.

“Well then maybe next time we need to make sure you can’t be,”

Vince gave an evil laugh as he bought his hand down - hard - onto the two oval lumps in Nolan’s briefs. Nolan gasped, spilling some of his and Mike’s drink on his crotch and the sofa. 

It was just in time for Mike to reappear down the basement steps.

“My couch!” You ruined it!” Mike declared dramatically, racing to the piece of furniture as if an actual person had died. Nolan laughed at his friend’s theatrics.

The two DILFs were laughing so hard that at first they didn’t hear Vince, whose cock was dripping as the literal man of his dreams was sitting almost naked on the couch. 

“Mr. Matson, my mom just got this couch. She’s gonna’ be pissed. I think that’s worth at least fifty more kicks...” Vince said half joking.

Nolan laughed, but started to get nervous as Mike and his son stood over him on the couch. They wouldn’t really hurt him, right?

“Oh, dad! Fun fact, when you were upstairs Mr. Matson told me he really doesn’t want kids,”

“Not a problem at all!” Mike laughed, still drunk and eyeing his buddy’s mounding crotch.

Nolan smiled as he started to stand, trying to diffuse the weird tension that was building, but was stopped by Mike pressing down on one shoulder and Vince on the other.

“Wha... what’re you guys doing?”

There was a brief pause with all three giving darting glances between themselves.

“What do you think? We’re gonna stop you from having kids!” Mike chuckled.

Nolan again tried to stand but was held in place. Then he noticed Mike and Vince were both eyeing the massive lumps in his briefs with different perspectives - admiration from a drunken Mike and lust from Vince - but the same goal; destruction.

“Umm.. guys...” Nolan said through a smile but was becoming increasingly nervous by how vulnerable he was wearing only his underwear as two strong blokes held him sitting on the couch.

“...Guys!” Nolan screamed dramatically, trying to use humor to break the spell his semi-busted nuts were having on his best friend and his young admirer.

It didn't work.

Family-line-ending commotion ensued in Mike’s basement while the next match of the World Cup played on in the background.

In the end, it was a good thing Nolan really didn't' want kids...