The Baseball Bet

I remember this one getting quite a few notes on tumblr years ago before it was deleted, and though I'd love to take all of the credit for it, the gif attached to the post did a lot of the heavy lifting. That gif and a few other sexy baseball themed photos I've collected over the years are linked on the Discord server for VIP members.

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Jim stood with his bare feet in the dirt, waiting on that stupid fucking kid to throw the ball. The college’s pitching coach, an old friend, had gotten conked in the head at practice last weekend, so they called him to fill in before the rivalry game against Carter State this Thursday. He hadn’t coached in years, but he was itching to get out of his house and back onto the field. He’d been here for just two days, and he was already questioning if the pay was worth it. This fucking perv on the pitcher’s mound had suggested a unique game to finish off practice: for every strike against Jim, he’d strip. For every hit, the pitcher would strip.

Jim thought he’d quickly embarrass the kid and head to the locker room, but the little fucker had been sandbagging all week. His first pitch was 30 mph faster than what he’d been throwing all week.

And that’s how Jim ended up here, with his cleats and socks neatly sitting beside home plate. The next pitch headed straight down the line, and Jim knocked it into left field.

Let me see that scrawny chest, kid.

The pitcher looked stunned that a hit had even been made, but he pulled off his shirt anyway. Well, he was skinny, but that tight frame was complete muscle. Jim could clearly count his eight pack all the way at home plate. He felt his cock twitch a little, but ignored that to focus on the next pitch. But it wasn’t gonna happen no matter how focused he was- the ball sailed right by him. Jim reached for the collar of his shirt, but the kid was already yelling.

Old man, I get to choose what you strip, remember? You’re losing those pants first.

Jim couldn’t believe what he was hearing. Now don’t get it twisted- Jim was damn proud of how good he still looked in his sixties, but he still would have liked time to prepare for this. Jim unbuckled his baseball pants and pushed them to his ankles. He was now standing with his cock out for that smug little bastard. Jim hadn’t worn a pair of underwear in decades, and he was actually completely confident in having his cock out. He had always been a shower, impressive from the get-go. Long and thick.

The kid was bent over laughing, but inside, a switch had flipped.

Nice dick, geezer. It looks like you haven’t used that thing in decades.

Ask your mother- she’ll prove you wrong. Now pitch, one more strike, and we had back into the locker room.

Jim got into his batting stance and tried to ignore the breeze currently blowing across his exposed asshole. He was prepared to miss swinging on the next pitch, doff his shirt, and head to the locker room. But when an easy pitch came across the mound, he instinctively swung and made contact. The kid was now unlacing his cleats while laughing. Fuck. This kid was now just throwing easy shots to keep me almost naked out here, and he wasn’t going to miss on purpose now to give the brat the satisfaction.

So, the game pressed on. Jim had sweat running all over his body, and there was a problem. He was starting to get hard.  As much as he didn’t want to admit it, this confident little prick was  turning him on. He had already lost his shirt and shoes and was wiggling out of his baseball pants… to reveal a pair of gym shorts. The pitcher started laughing as soon as he saw Jim’s face.

That little shit had conned him.

By now, the rest of the team had already changed and showered and were heading back to the parking lot which was right behind the field. As soon as they got within viewing distance, they started whistling and catcalling their substitute coach. A couple of them had to shift their duffel bags in front of their crotches.

Jim hit another easy pitch, and the pitcher shimmied out of his shorts into a pair of boxers. As he hiked his leg up to get ready to pitch, the tip of his cock slipped into view. Jim knew that he was going to knock this pitch out of the park no matter what. The pitch seemed to come towards the plate in slow motion, and he heard the audible crack as his bat connected with the ball. The pitcher watched it sail past the fence. When he turned around, Jim was standing right in front of him holding the cracked bat.

Looks like you owe me another article of clothing, boy.

And with that, Jim yanked the boy’s boxers to the dirt. The boy’s hairless cock burst into view. He tried to get his underwear back up, but Jim had his foot on top of them. One of his teammates had snuck up behind him, grabbed his clothes, and slapped him on the ass. Admitting defeat, he stepped out of his boxers and started the long run back to the locker room.

Jim passed off the bat to one of the players and walked back to collect his stuff. He may not pitch as fast as fast as this kid, but he had someone waiting for him at home. He walked to his car with shoes in hand and pants over his shoulders.