Triple Play

Triple Play- Baseball to Santa to Smiles... by Strappy Sandals

This is a Winter Holiday 2023 contest submission, so if you like it, please vote!! And, as always, all characters engaging in sexual activities are over the age of 18. I enjoyed writing this story, and truly hope you enjoy reading it. Merry Christmas to all!!

Jimmy, it breaks my heart to tell you this, but I can't offer you anything good right now," said Harry Witkowski, GM of the Philadelphia Phillies. "I've got Hector Gonzalez, who had a breakout year in Reading ready to play second base. And I've got Willie Clendenon, and Tommy O'Malley with the Iron Pigs ready to come up as well. If things break the way I think they will, my roster is already over-booked for next year," he continued. "Jimmy, you're a good player, and a great luxury on a winning team, but right now, I'm not sure the Phillies are that team," Witkowski said, trying to justify the bad news. "And I'm only telling you this because you're a great guy. You were a big part of our team last year. We hung till the very end, mostly because you filled every hole in the lineup. You kept us afloat; I get it!" the GM sympathized. "I want you back; I swear I do, Jimmy. But I got to see how the shit shakes-out before I can offer you anything. I just can't do it right now," he redundantly stated, trying to justify his position.

Jimmy Skizinski, or "Jimmy 2-Ski", as he was also affectionately known, was a thirty-year old professional baseball player for the Philadelphia Phillies. The season before last, he was a Cardinal for one season. Before that, a Miami Marlin for one season, before that an Oakland A, prior to that a Texas Ranger, and his rookie year was spent with the Milwaukee Brewers. Six years in the big leagues, on six, mother-fucking-one-year contracts, with six different clubs. Every fucking-year, a one-year contract. That is incredibly hard to do in major league baseball.

2-Ski's career slash-line was .269 / .338 / .455, (batting average / on-base percentage / slugging percentage) which is MLB, "pretty-fucking-good". Scott Rolen just got into the Hall of Fame this year, and his slash line (.283 / .377 / .469.) is only marginally better than Jimmy's. 2-Ski is a good left-handed hitter, capable at multiple defensive positions, a great team-mate, and up to this point, always healthy and available. But GMs always seem to focus on the half of the glass that's empty. Jimmy makes great contact, but he doesn't walk much, thus lowering his on-base percentage. His power is consistent, but unspectacular, in what is now a power game. Plus, he's now out of his 20's, and "jack of all trades" good, but not a super-star at anything. On every team he has ever played, he's found himself in the "odd-man-out" position. Either he was a kid, and the team wanted experience, or the team was going with a youth movement, and he was too old. Or they had a phenom coming up to play his position, or they needed to carry another pitcher, or a DH, or a right-handed bat, or some fucking-kid that sucked but the GM drafted him. Every year, it seemed the same fucking-story; No matter his production or presence, Jimmy 2-Ski was a luxury that a team couldn't afford, until all their other options went to hell.

"Harry, I had a fucking-career-year here," Jimmy countered. "In 302 at-bats I slashed .278/ .375 / .465, with 51 RBIs, and 16 fucking-dingers. Extrapolate that out to 600 AB's, and we're talking 32 home runs and 102 RBI's. Those numbers would have led the club, Harry, and been top 10- in the league," Jimmy argued. "I don't understand how you could NOT offer me a multi-year deal," he added. "I'm not giving myself away for free," Jimmy continued, "but I will give you a 'home team discount. I want to play for the Phillies, but I want a three-year deal; minimum. I love this fucking-town! I love playing at C.B.P., and I love playing for the Phillies, but I need a deal that represents my value Harry," Jimmy continued with increased volume. "I started 6- games in left, 12- in right, 12- in center, 13- at second base, 14- at third, 6- at short. Fuck, I even caught in 2- games, Harry. No way Gonzalez, Clendenon, and O'Malley combined will give you that flexibility or production. I don't care how fucking-good they are," Jimmy added to close his argument.

"Jimmy, I know all that," the GM conceded. "But I need time to see how things shake-out. Why don't you go home and enjoy Christmas, then call me after the holidays. At that point, I'll know better how the market has moved, and what I can do," the GM offered the dissatisfied player.

It was at that moment of defeat for Jimmy, that Mr. Witkowski's assistant knocked on the door to interrupt the negotiation. "Mr. Witkowski sir; Oh, 2-Ski, I am so sorry for interrupting, but we have a huge problem, sir," she announced to her boss. "We have the Cleft Lip and Palate Christmas party scheduled for 3pm tomorrow, and Fig was supposed to play Santa for the children," the assistant went on. "And he's ah," she began mumbling.

"Sara, what's the damn problem?" the GM asked, somewhat perturbed.

"Fig says he won't do it, Mr Witkowski. He says his agent has booked him for a paid appearance at Delilah's Lair, and, according to him, 'he can't be doing no fucking-charity work', when a paid appearance is an option."

"He's blowing off sick children to appear at a fucking-strip club?" Witkowski questioned incredulously. "What the fuck is the world coming to?" he asked, mostly to himself.

Fig was the nickname for the Phillies perennial, all-star first baseman, Newton Figarelli. Rarely did anyone ever call him by his given name. Most everyone knew him as either Fig, or Fig Newton. He was a big, gregarious, high maintenance, highly paid, self-centered sort of player, and personality. He was the Phillies' biggest star, and the center of their marketing campaign. A fact in which he took generous advantage.

"Can't you call some sort of Santa hotline to get a replacement?" the frustrated GM asked. "What do the department stores do when Santa gets sick?"

"Sir, the event was marketed as 'Fig Newtons with Santa'. If we try to make a second-rate substitution, sir, there will be an awful lot of disappointed children, as well as parents, and ticket holders. We could certainly explain his absence due to sickness, but we'd need a suitable replacement. Is there any way we could get another player to become Santa for the afternoon?" the assistant asked.

"Sara, all the players have scattered, and gone home," the GM responded. Nobody is magically going to fly in with reindeer to play Santa Clause," he added. "You call the Santa hotline, or whatever replacement options you might have, and I'll call Fig's agent to see if I can get him to delay the stripper meeting till later in the evening," Witkowski offered, showing at least some sympathy for the young assistant's problem.

"OK, thank you, Mr. Witkowski," Sara responded, hoping for a miracle somehow.

Alas, the miracle did not occur. Harry Witkowski did call Figarelli's agent, and he was basically told to "fuck-off". Essentially, Fig liked strippers a lot more than challenged children, and he was not going to change his mind for Harry Witkowski.

Jimmy 2-Ski watched the Fig Newton drama unfold, while simultaneously scheming to make his final pitch to the GM before departing for his own winter break. As Witkowski hung up the phone with Figarelli's agent, Jimmy saw Witkowski's eyes light up and grow, sort of like the Grinch after finding the true meaning of Christmas.

"2-Ski, I know your contract has expired, and I know you're technically no longer a Phillies player, but I'm going to ask a big favor of you Jimmy; can you play Santa Clause for us tomorrow?" the GM asked. "You're still living in town, aren't you?" Witkowski added to pressure Jimmy.

"Oh, what the fuck, Harry?" Jimmy 2-Ski bellowed. "Fig's fucking- six foot five, 265. I can't pass for Fig." Jimmy protested. "And you ain't got no room for me, remember?" he added for emphasis.

But the GM totally ignored Jimmy's refusal. "Sara, can you come back in here for a moment", the GM requested via the telephone speaker. Then, turning to 2-Ski added, "we can fluff you up with a couple pillows, Jimmy. Don't you worry about the details, Sara will handle that shit," he added, to help Jimmy swallow the bitter chaw.

"Sara, meet Santa Clause," the GM proudly announced to his assistant, while pointing at Jimmy 2-Ski.

Jimmy again voiced his disapproval of the whole situation by stating "I can't pass for Fig. This whole idea is stupid," he added. I'm not even a Phillie anymore," he continued to balk.

"Oh Jimmy, thank you so much," Sara beamed appreciatively. "This is going to work out so well," she added. "And I know you're going to love it when you see the smiles on those children. Many of them face difficult circumstances, so when they have happy days, it is magical," she added to close-out Jimmy's negativity.

Jimmy 2-Ski, while still working under protest, realized he had been defeated by the GM and the pretty-little marketing assistant. Truth be told, Jimmy truly enjoyed volunteer work, especially with children. Being single, he found himself lonely on more than a few occasions, and working with children, and families, helped him feel better about his own place in the world. So, as he began to mentally accept his fate, he also let his mind wander to how attractive Sara was. Jimmy 2-Ski had scouted her out almost immediately after signing on with the Phillies, but the club had an unwritten rule about employees dating players. So, to minimize trouble for them both, he mostly admired her from afar. But this little Santa assignment might provide an opportunity to get to know her better without putting either at risk. And, technically, he was no longer on the Phillies roster.

Sara was very petite, maybe 5- foot tall, or so, and slender. She always wore heels, so she looked taller than she actually was. She had long, golden, curly blonde hair cascading down to her lower back, and beautiful skin, smile, and face. She was also nearly completely flat chested. Almost no tit whatsoever, but it really worked for her in an athletic sort of way. She was beautiful, sweet, and stylish, while strutting around in those high heels, making her a complete TEN in Jimmy's eyes. Very nice!

"Alright, alright, I'll do it," 2-Ski announced what was already a done-deal to everyone else. "When is it? And what do I need to do?" he asked.

"Oh Jimmy, thank you so much," Sara screeched, while leaning in to hug Jimmy. While hugging Sara, Jimmy let his hands linger a moment on her back, curiously noticing no bra straps at all, while simultaneously pleasuring in her intoxicating feel and fragrance. This whole Santa Clause opportunity just might not be a bad thing he mindlessly thought to himself.

The reality for Jimmy Skizinski was that he did not have much in the way of family. Both sets of his great-grandparents were Polish immigrants, who left Poland in the late 1930's to escape the horrors of Nazism. For one odd reason or another, both Jimmy's grandmothers, his mother, and he, were all only children, leaving him with virtually no brothers, sisters, aunts, uncles, or cousins to share his life, or holidays. So, given his dearth of family, and his status as a single man living the life of a baseball vagabond, he routinely found himself in an annual predicament to find purpose, and a little love, at Christmas. Maybe playing Santa Clause would provide a fun diversion to escape the loneliness, and his suddenly dour baseball situation.

"Jimmy, can you be back here about 3pm tomorrow," Sara questioned, trying to lock Jimmy into her plans. "The party will start at three, with a meet and greet for the parents, children, and Phillies employees. Ideally, you'll be here at that time, and we'll introduce you as Jimmy Skizinski, the great ball player. You can meet the kids and parents, and hand out a bunch of Phillies gear with the Phanatic. At some point we'll usher you away for 45 minutes or so, while we do lunch, and announcements. While you're disappeared, we'll feed you, and then the CLAPA team will dress you out and turn you into the greatest Santa Clause ever. We'll outfit you with a bag of toys, then call you out to meet the children. Each child will get a few minutes with Santa, then we'll hand you a gift specially chosen for that child as they depart. You should be out, no later than 6pm," Sara said, concluding her schedule plans. "How does that sound?" she hesitantly asked, hoping Jimmy did not change his mind.

"Sounds like you've got it all figured out," Jimmy concurred with a smile, and suddenly a very good feeling about the whole thing.

"Oh, Jimmy, thank you again so very much," Sara said while hugging Jimmy once more.

Jimmy 2-Ski was a stickler for preparation, so on his way home, he decided to drive to the Columbus Ave. mall to check out the operation of an actual working Santa Clause.

Thankfully, Jimmy mused while walking, he was able to stroll the mall anonymously. He was not the Phillies' most popular player, but he had a good year, got a lot of playing time for the home team, and was pretty much on television every night for the past six months, so he was generally recognized around town. The Eagles being 8-1, and Jalen Hurts battling for the M.V.P. award probably had everyone focused on the more popular football team, but whatever the reason, the mindless anonymity was a true pleasure.

Anyway, Jimmy 2-Ski found a bench, opposite the North Pole Operation, and spent an hour or so scouting the program, people watching, and making a few observations. First and foremost, Santa was the star player of the entire show. The game revolved around him. Good Santa; good operation. Bad Santa, the whole thing sucked, Jimmy theorized. Today's mall Santa was a fucking-sad-sack loser. No energy at all. No smile, no welcoming greeting, no hugs, and no interaction with Mom or Dad. Nothing, but a dude collecting a check, and Jimmy played with enough of those losers to recognize the poison immediately.

Secondly, the elves ran the show. Clearly, their priority was to keep Santa happy and refreshed, which they were always working to do. But they were also responsible for managing the line-up, coordinating the needs for each child and parent, directing the photo shoot, providing the parting gifts, as well as keeping a happy and fun ambience at the North Pole. In short, they worked their asses off to keep everyone happy. At this mall they had three young ladies working to support the Santa experience. They hustled, they were friendly, and they were always busy.

Curiously, each of today's elves was a beautiful woman in her own right. Each wore a unique, but thematically similar little uniform. Each outfit had different cut and color but was similar in exposing some nice titty-top, and a lot of leg beneath a short, tight skirt. Also, each girl was wearing identical, red, high heeled shoes, which added an extremely nice element to the outfit. Playing in today's game, we had Elf one, who was a gorgeous redhead, with classic green eyes, curvy build, athletic, and bubbly. Elf two was a little pixie brunette. Short in stature, short dark hair in a bob cut, olive skin, thin, and with the bounciest titties that Jimmy had ever seen. And fucking-Elf three was a stunning black girl. She was tall and thin, maybe 5'-10" or so, had perfect café-au lait skin tone, braided afro hair, and tits that were big, just short of huge. Quite a starting line-up, but, as good as these elves were, they could not overcome the weakness of the star-player. This Santa sucked!

Jimmy's third observation was the intensity of the parents, and their laser-focus on their own child. Each was almost in pain trying to provide their child with that memorable Santa Clause experience. Most were pleasant and patient, but the unrealistic desire made some of them belligerent, bull-headed, and oblivious to anyone, or anything around them as they pursued the desired outcome. It reminded Jimmy of his early Little-League years, and how some parents saw nothing except for the actions of their own child. The whole fucking-bench could be on fire, but if their little boy was at the plate, they'd let the dugout burn down. In mom and dad's eye, their kid was the next fucking-Willie Mays. Managing the parents could be a challenge, but if he could keep the kids happy, mom and dad would stay out of the dugout.

2-Ski's final thought was to appreciate how the experience was a true American melting pot. Black, White, Oriental, Spanish, Indian, and every flavor in between. Tall kids, skinny kids, heavy kids, well-dressed, and kids not so well dressed. 2-Ski watched as kids with casts, in wheelchairs, mentally challenged, glasses or blind, or with other issues, all smiling as big as they could, waiting for their turn with the jolly old Elf. Those smiles sent chills up Jimmy's ass, and made him vow at that moment, he would be the mother-fucking MVP of Santa Clauses tomorrow. "Put me in coach, I am fucking-ready," he whispered to himself as he strolled out of the mall.

Jimmy Skizinski currently lived on the penthouse floor of a luxury Condo building on Locust St., in the Society Hill section of the city. The condo was only a short drive away from the mall, and thus 2-Ski was home in a matter of minutes after his scouting assignment. Before heading up to his apartment for the night, Jimmy decided to stop for dinner, and a drink, at Bridgette Foy's, his favorite Philly eatery, before parking himself in front of the TV to watch college football before bed.

Jimmy loved Bridgette Foy's Bar and Restaurant. A true Philly hotspot. He loved the staff, the ambience, the customers, as well as the food and drink. It was all good at Bridgette Foy's! As he walked into the bar area, Jimmy immediately made eye contact with the barmaid Joanie, who, with a wink of her eye and a twist of her head, gave Jimmy the sign that she had a seat for him at the end of the bar.

Conveniently, Joanie met Jimmy at the end of the bar and showed him a seat next to an older gentleman, quietly having dinner alone. "Jimmy 2-Ski, meet my Uncle Arthur. Uncle Arty, meet Jimmy Skizinski, my friend, and my absolute favorite player on the Phillies," Joanie announced to her uncle as she leaned over the bar to give Jimmy a big hug.

Jimmy 2-Ski loved Joanie. She was his first, and one of his best friends in Philadelphia, and the most beautiful person Jimmy had ever met. Joanie was a MILF of the truest kind. Jimmy did not know much of her personal life, but he did know that she was on-again / off-again with her husband, with whom she shared two young daughters, one of which had some physical ailments. Joanie was likely in her mid to late thirties, 5'-6" or so, thin, smallish tits, but with a bubbly ass that was to die for. She also had the most luxurious, porcelain skin, deep blue eyes, and long, straight, jet, black hair; so soft and black, it was almost blue. Uniquely beautiful in a 'Morticia Adams' kind of way, without the weirdness. But her most memorable trait was her pleasant demeanor. Joanie was always happy and eager to serve. Always there to help anybody at any time, which Jimmy witnessed and experienced on many occasions. In fact, Jimmy's first meeting with Joanie was clearly one of those occasions.

Their initial meeting occurred almost one year ago tonight, at Bridgette Foy's. Joanie had been attending a wedding on a Saturday afternoon but came into work later in the evening to fill in for another server who had gotten sick on the job. She went straight to work in her heels, and luxurious, wedding-guest dress, looking great as she served up dinner and drinks to the pre-Christmas crowd. Jimmy was just finishing a whirl-wind weekend, having moved into his apartment, and signing his Phillies contract. He was dining with agent, and his assistant, while dressed in a nice suit and tie, and looking as good as Jimmy 2-Ski could make himself look. Long story short, Jimmy got excited telling a funny story, jumped up laughing and throwing out his arms, and backing right into an over-loaded Joanie with a full tray of food for other customers. Meatballs, gravy, spaghetti, mac & cheese, creamed spinach and more, now covered both ballplayer, waitress, and surrounding floor. A complete shit-show of a mess.