Chess Swindle

[Perplexed]

I managed to carve out a bit of time to write this short story. Any feedback is always appreciated.

Chess Swindle:

This Saturday morning, like all Saturday mornings, Kyle was walking through his local park and towards the chess tables that were set up. At only 24, Kyle had already been promoted to a Portfolio Investment Manager with the investment business he started with right out of university. Only a year in, and although Kyle loved his job, he appreciated having his Saturdays off to destress and play some games of chess before going about his weekend. Sure, he mainly ended up playing against older gentlemen that he hardly had anything in common with, but the stakes were nothing and let him relax himself.

Unlike the stereotype, Kyle wasn’t a slouch in the fitness department either, making sure to eat healthy and go on runs before work. With a good height of 5 ‘10, Kyle had the appearance of a sleek fit runner, never having tried to bulk his muscles up, but rather simply kept them toned and respectable. His member was equally respectable at 7’. Combining this with his work ethic and generally handsome and well groomed features, along with his warm personality, made sure that Kyle was quite the catch. In school, as well as at work, Kyle could tell that a number of women had their eyes on him. Enjoying their company, Kyle went on a number of dates, but a pattern soon emerged, he never went for the office hottie, but rather, the quieter office nerds.

As Kyle passed along the tables, he saw the usual suspects hard at work trying to best each other. After going to the park for weeks, Kyle quickly learned that some of the men went to the park to hang out with their buddies and would only play the same person each week, while others were looking for new challenges. As Kyle walked, he saw a new face this morning, a small Indian girl who couldn’t have been much older than 20 with a slightly out of shape frame. Her large glasses and focus on the puzzle she had set up on the board had already gotten Kyle smiling as he looked down at her. Sure, she had fairly plain features, but Kyle could see intelligence behind her big brown eyes and thought she looked cute.

Staring a couple seconds too long, the woman looked up at Kyle and smiled.

“Care to join me?” the woman greeted

“Sure, I think you’re the prettiest opponent I’ve had in a long time. I’m Kyle.” Kyle greeted, holding out his hand to the woman

“I’m Jenna, nice to meet you.” Jenna replied, blushing slightly

Quickly, the two took down the puzzle and rearranged the pieces so that they were in their starting places, with Kyle taking the black pieces.

“Are you okay with black?” Jenna asked meekly

“Definitely, if we have another game we can always switch.” Kyle confidently answered with a smile

Although Jenna seemed to be shy to Kyle, the way she stared into his hazel eyes showed an inkling of either desire or confidence and he couldn’t quite put his finger on it. Meeting her gaze, Kyle just smiled as she made the first move. Looking down at her move, Kyle was puzzled as unlike most players, she wasn’t moving a pawn up into the middle of the board, but instead moved her outside pawn up a single square.

“Maybe there’s some kind of trap here that she’s going for?” Kyle queried to himself

Moving up the pawn in front of his king two squares, Kyle watched as Jenna once again moved up another outside pawn, one square on the other side of the board.

“She’s not fighting for the middle?” Kyle continued his inner monologue

Seeing this opening, Kyle took the center of the board with the pawn in front of his queen. The game continued in this vein for another 15 moves as Kyle built up a stranglehold in the middle of the board, while Jenna seemed to be lacking any strategy at all. Her pieces were split to the sides of the board, while she left her king in its starting place.

“It’s like she’s trying to get me to attack her or something?” Kyle questioned, before moving in for the kill

Piece after piece of Kyle’s went in for the attack, and the king hunt was quickly on.

“I think I might have you in this one.” Kyle smirked

“Oh umm, maybe?” Jenna smiled back

As Kyle had predicted, it wasn’t much more than another five moves before Jenna’s king was trapped and checkmated. Still with most of her pieces on the board, but out of position, they were helpless to help Jenna protect her king.

“Oh darn,” Jenna laughed, “How about another and this time a bet?”

“Like if I win, I get to take you out on a date?” Kyle laughed

In response to this, Jenna leaned over the board ever so slightly, showing off the slight cleavage her B cup breasts could produce, before Kyle felt a hand trace up the inside of the leg of his jeans. Stopping just shy of making contact with his member, Kyle gulped.

“And if I win, I get your dick. Deal?” Jenna whispered in a sultry voice

“Oh, yes, deal.” Kyle said flustered and shocked by this unexpected response

“You’re really cute and you don’t know how long I’ve been waiting to meet someone like you. What do you do, by the way?” Jenna continued

“Oh I’m a portfolio investment manager with an investment business. I’ve only been there a year, but they hired me right out of university because of my GPA.” Kyle replied, taking the moment to show off a bit

“Oh wow, that’s amazing.” Jenna smiled almost predatory

“What do you do?” Kyle returned the question

“Oh you’re a few years ahead of me I think. I’m still a student in university, just wrapping up my second year.” Jenna answered with a dismissive wave of her hand

“Well I’m 24 so I guess that would make you 21.” Kyle answered as he finished setting up his pieces for a second game, this time as white

“True, not that I care about that.” Jenna winked

Kyle could feel his heart starting to thump a bit in his chest, fully smitten with the girl in front of him who seemed to be the one with all of the power in their dynamic, regardless of being younger than him. Smiling, Kyle made the first move, once again moving his king’s pawn up two squares.

This time, however, Jenna moved her king’s pawn up one square, and Kyle could see that they were already going to have a bit closer of a game. Without hesitating, Kyle began to move his pieces, a smile growing across his face. As they moved back and forth, a real battle was underway with neither giving the other one an inch. Every attack Kyle tried to start, Jenna stopped, while Jenna failed to get her pieces even close to attacking Kyle’s king. Looking over at Jenna, Kyle couldn’t get over how cute she looked as she was sitting there thinking, and he could hardly keep his mind on the moves he was making. He watched Jenna move up her queen, his eyes lingering on her intently focused face for a few seconds.

“Even if I win, she can have my dick and I’m going to take her pussy and show her just how much she can cum.” Kyle laughed to himself mentally

Moving without thinking, due to his mind wandering, Kyle immediately saw his mistake.

“Distracted?” Jenna chuckled

“Shit, yeah. Not a good move.” Kyle answered with a bit of annoyance coming through in his tone

Kyle watched as Jenna immediately took advantage of his mistake using her bishop and skewering his queen with a check on his king. The two had been very evenly matched, Kyle thought, during this game, but with his one mistake it was all over. He debated playing on and seeing if he could make a comeback, but going home with Jenna seemed to be a great result.

“I resign.” Kyle smiled, turning over his king

As Kyle spoke the fateful words, he felt his body tense up for a second, as if the air around him had grown heavier.

The change that had taken place for Kyle, was barely perceptible due to the speed at which it had taken place. Atop his head, his blonde hair had grown from the short inch he had always kept it at, down to his shoulders. Before Kyle had even felt the tickle of his hair passing by the sides of his face, his ears had grown smaller and became pierced, while his skin also became softer and smoother. The overall shape of his head rounded out as his features softened, his nose shrunk, his eyelashes grew and his eyebrows thinned. Even Kyle’s lips had puffed up ever so slightly, making them fuller and more enticing. Although Kyle’s face had changed, he still bore a resemblance to his old self, now with the face of a beautiful sister, rather than the handsome brother.

The transformation continued downward with speed though, pushing in his Adam’s apple as his neck thinned and his skin continued to become softer and more smooth. As Kyle’s shoulders next pushed in to become more narrow, along with his chest, his pectorals gave way and reshaped themselves into two C cup breasts that sat perky on his chest. Following his chest, Kyle’s stomach pushed in, remaining firm but giving him a slight hourglass shape.

As Kyle’s stomach had pushed itself in, his hips had flared out, along with an expansion in his butt. Now with a nice feminine rear that had been sculpted through yoga and running, the remaining muscles of Kyle’s arms and legs became less prominent and softer. Instead of having any strong features left, Kyle’s appendages looked like they belonged to a woman that kept herself in fit and healthy shape, but not one that lifted weights. With this shift in look, Kyle’s body hair vanished and the rest of his skin smoothed itself out to match his face and torso. With Kyle’s arms and legs changing so quickly, he couldn’t have noticed as his finger and toe nails grew out slightly, before a respectable peach nail polish spread across them. The last thing to change was between Kyle’s legs as his member shrunk up into himself, before being replaced by a tight and well-shaven vagina.

Shaking his, or rather her, head, Kyle looked down at her body and immediately grabbed at the breasts on her chest. Still wearing her old male clothes, the lack of a bra allowed Kyle to grab her new boobs directly, feeling slight pain at how sensitive they were.

“Oww…oh my god, my voice…my body. This isn’t real, it can’t be.” Kyle squeaked in a panic, her voice coming out much higher than she was used to

“Well I did say I’d get your dick if I won.” Kyle heard a man speak across from her

Looking up, Kyle could see a small Indian man where Jenna had been smiling up at her.

“You did this?” Kyle questioned

“Yes, and if you want to be a man again, you’d have to beat me….Kylie.” Jenna grinned predatorily

“Kylie? I’m Kyle. Fuck, why would you do this?” Kylie questioned incredulously, realizing that she must have looked silly still calling herself by her old name

“To get to be a man? Why would I want to be a girl? Think of this as a chance to get to see the other side and call me John.” John laughed

“But, but…fuck!” Kylie started, trying to wrap her head around what had just happened

“So, shall we play?” John asked, still smiling

“Fine, and if I win, I get my body back.” Kylie replied in frustration

“That sounds fair, but if I win, I get your height.” John answered as he began grabbing black pieces

“My height?” Kylie said in fear

“Yes, you think I want to be a small man. No, I want to be able to really dominate a girl I take home, not be the submissive one.” John smirked

“Fuck you, I won’t be the submissive one either.” Kylie snapped

“Such an angry mouth on such a pretty girl.” John laughed

Kylie could feel herself growing red with anger, but chose not to respond and instead began setting up her white pieces, ready to beat this John and get her gender back.

Even more confident than before, John matched Kylie’s moves almost immediately. Kylie, however, was feeling even less confident than before. With each move of her arm, Kylie’s unsupported chest bounced ever so slightly, a feeling that she could never have imagined she would feel. In addition to her chest rising and falling with each breath she took, and bouncing as she moved her arms, Kylie was equally distracted by the new padded feeling on her backend, as well as the new emptiness between her legs.

“How is John so calm?” Kylie questioned mentally, making another move

Try as she might, Kylie could barely keep her mind on the game at hand, regardless of the consequences. Playing through the distraction, Kylie simply made moves that made sense to her, rather than looking at what her opponent was doing the majority of the time.

“Check.” John noted calmly

“Oh…” Kylie gasped

“Guess you must have been distracted, there goes your queen.” John chuckled

“This body….I just can’t focus.” Kylie whined

On the board, John had forked Kylie’s king and queen with his knight, easily putting him in a commanding position of the game.

“Can we talk about this? I was just too distracted.” Kylie protested

“Is that the case?” John smiled

“It is. These boobs keep moving, and then my hair is in my face and…” Kylie pleaded

“Maybe we can play again after then. You know, if it’s only because you were distracted.” John suggested

“Fine.” Kylie huffed, crossing her arms and pushing her boobs together without realizing it

As Kylie saw John’s eyes lock onto her bust, she pulled her arms back in humiliation.

“Pervert.” Kylie fumed

“Well, you were the one giving me the show.” John winked

“You’re just an asshole, fine I resign.” Kylie answered in defeat

With the game ending, Kylie braced for impact knowing just what she would lose this time. As quickly as her gender had changed, her height changed at the same rate. Still being 5 ‘10, Kylie had been definitely considered a tall woman, but that would no longer be the case. Quickly, the inches shaved off her frame as she plummeted down to an even 5’ tall. The board was now much closer to her chest, instead of her stomach, while the man across from her now towered over Kylie. To add insult to her loss, Kylie watched on as John inspected his new larger frame, beaming from ear-to-ear.

Looking down at herself, the C cup breasts on her chest now looked even larger when compared to the rest of her torso. That is when Kylie noticed one other change that had taken place. Her feet, which had been resting firmly on the ground during the last three games, were no longer touching the ground. Instead, she could kick her feet freely, only able to touch the ground if she fully leaned forward.

“I’m so small.” Kylie noted out loud sadly

“It looks good on you. A nice petite girl.” John laughed

“Shut up!” Kylie spat

“Well I guess just petite then, petite and fiery.” John continued

Feeling her face growing red in frustration, Kylie stared daggers into John, looking almost ready to punch him over the table.

“Now, before you do something you might regret, remember I’m your only way back to your old life. If you attack me, and I doubt you could really hurt me with your new size, then I also might just get up and leave, leaving you in whatever new life this version of yourself would have fallen into. Maybe a secretary or a waitress? Maybe this version of you already settled down with a nice strong man and you have some kids at home? Is that a risk you would be willing to take?” John said with a shit-eating grin

Kylie wanted to stop herself, but John’s smile was just too much. Before even thinking, her hand swung forward, instinctively throwing a slap, instead of the punch she would have thrown as Kyle. As if expecting this, John batted her incoming hand away, with a chuckle.

“Shall I go then, or will you play again?” John asked, still smiling

“Uh, I hate you!” Kylie exclaimed in frustration, before grimacing and asking, “Fine, I want my height and gender back. What do you want?”

“Only what I think would be fair. I would love to finish the change and look like you with your old face and body, you know, your genetics. So, how about your old genetics and life against mine” John calmly requested

“But then I would look like you used to look?” Kylie questioned

“Is that such a bad thing? I thought you thought I looked cute? Or you could win and go back to how you were before, are you willing to take that risk?” John asked, knowing the answer already

“I did think you looked cute, so why are you doing this to me? I liked you?” Kylie questioned, tears forming in her eyes

“Because I wanted to be you.” John batted away her question, before adding, “Look at your body, you’re a petite girl. The only difference will be looking like you’re a part of my family instead of yours. Is that such a big change to have my genetics and be from my family instead?”

“I guess not.” Kylie admitted in defeat, hoping to be able to win and pull herself back into her old body

“Good, then let’s play and I’ll even give you white.” John smirked

“Maybe if I play a rarer opening, John won’t know what to do and I could score an easy win? I think he might be better than Jenna had let on.” Kylie thought to herself, pausing as the two set up the pieces

With a few more seconds passing, Kylie seemed almost frozen with indecision, before John piped up.

“No one is forcing you to play this game. You can walk away now and be the cute and little Kylie if you want.” John smirked

“Shut up!” Kylie shock back, before making her first move

“Oh, a new opening.” John smiled, seeing that Kylie had moved a knight forward instead of any of her pawns

With the smirk still planted firmly on John’s face, Kylie felt her confidence growing smaller and smaller as she looked on. She had begun with a move that had only been played against her in the past, but never by her and was hoping it would be enough to skirt by. As John made his move, Kylie tried to match his smile and made her move immediately, hoping to exude the confidence that was lacking internally.

Almost as if the pair had been playing a round of speed chess this time, they each made their moves back and forth very quickly. John’s moves were immediate and precise, leaving Kylie trying to play catch-up as she tried to keep up the facade. Only ten moves in each, however, John stopped after Kylie let go of her queen.

“You really don’t know what you’re doing do you?” John asked with a condescending tone

“Of course I do.” Kylie retorted, a bit taken aback at John statement

“Then you would have known that by moving your queen forward like that, you’d be falling into an opening trap. Your queen could run back, but then you’ll get checkmated in the next three moves. Or you could sacrifice her and try to play on without your most powerful piece.” John gloated

“Wait, what?” Kylie answered, perplexed, before closely looking down at the board

“He’s right!” Kylie thought to herself after a mere few seconds, as John’s move came into focus

As Kylie looked down at the board, John merely sat back in his chair. He didn’t have to even make the move, which looked crystal clear to Kylie now.

“Shall I make my move, or will you just resign?” John chuckled to himself

“There has to be a way out.” Kylie whispered to herself, her face contorted somewhere between concentration and despair

With Kylie’s pain fully on display, John slowly picked up his bishop and advanced it into an attack on the pawns in front of Kylie’s queen, as well as her queen itself. This left Kylie with the painful realization that she could either give up her queen and trade it for the attacking bishop, delaying the game by a few more minutes or pull either her queen or another piece back to let John win.

“Don’t worry, I’m sure you’ll love being me more than I did. I just failed out of school, so you really were a lifeline. I’ll make sure to take care of your life though and get lots of promotions, while you get sent back to India when your student visa expires.” John continued

“What’s going to happen to me?” Kylie said in shock

“Well, I was only a student on a visa, which is about to run out, especially with how poorly I’ve been doing. That’s why I came down here with this magic set. I couldn’t bear going back home, getting stuck marrying someone from my old town, and end up just popping out some babies for them. Given the choice between being stuck at home all day as a maid with no future except to be a mother, and being free with a nice paying job, you can’t be surprised why I was happy to swindle you into this game. I didn’t want to be one of those sixty year olds you see around here. Although I did consider the one lady I saw, I just couldn’t get her to play me a second time.” John monologued

“So you entrapped me?” Kylie cried

“You could say that, but either way…move or don’t and forfeit the game.” John sternly added

“Fuck! Then I’ll just refuse to move and we can be stuck like this.” Kylie protested

“I thought you might say that, but you see all chess tournaments have judges and this one is no different. In the event that you refuse to move, you lose. The chess set is the judge of this game.” John laughed

Kylie looked around the board for a way out, but nothing was coming to her mind. It seemed that John had thought about everything and she was trapped.

“I resign.” Kylie sadly answered in a barely audible voice as she turned her king on its side

As her king hit the board, Kylie watched on as the final changes began. Her white skin began to tan quickly into a dark caramel. Her hand had gone from almost matching the piece she was holding, to looking much closer to the black wooden pieces that had been in front of John. With her skin changing, the peach nail polish on her hand also darkened to a light brown. With her skin tone changing, Kylie noticed that she wasn’t only changing in color, but also in weight. Instead of keeping her trim physique, her body inflated ever so slightly into the slightly pudgy range. This version of her body wasn’t fat by any means, but gave off more of a couch potato vibe. Making this worse, Kylie’s breasts deflated slightly, going from C cups, down to Bs, and looking even smaller on her now larger frame.

Following this, glasses appeared on the bridge of Kylie’s nose, but felt right. Kylie’s vision didn’t even seem to blur, and she knew immediately that she would need these for the rest of her life. Around the glasses, Kylie’s face began to morph, losing the bright beautiful features she had only had after losing her gender, and in their place, gaining more plain features. Around her head, the blonde hair she had possessed darkened into a deep brown, which matched her new eyes. Her nose had widened slightly with these changes and now held her glasses in place.

What Kylie wasn’t expecting was the new memories popping into her head. Instead of remembering her old life as Kyle or even Kylie, she was now Jenna. Having grown up in India, she now remembered her name as Jenna, and how she had to fight with her parents to even get the chance to go to the United States. Jenna had always been a natural prodigy, but also fiercely independent. She picked up hobbies with ease, but her parents were always there with their judgments. They had always wanted her to settle down, and had even set up a man to marry her, but Jenna had hated this prospect. Having easily gotten into a university as an international student, Jenna realized that she had thrown away her chance to get her degree by partying and skipping class, relishing the new freedom she had obtained. It had even started to show on her frame, as she had past the freshman fifteen by a few extra pounds.

“No, you’re just taking the easy way out again and letting me pay for your mistakes.” Jenna pleaded to the new Kyle that was now before her

As Kyle was picking up the pieces and throwing them in a bag, Jenna noticed his clothing beginning to change. The bra and v-neck shirt he had been wearing morphed into a crisp white dress shirt, while his pants changed into a more dressier and less stretchy material. Jenna instantly knew just what Kyle had been wearing, as she looked down at her own new outfit.

A black push-up bra had appeared on Jenna’s chest, giving her some much needed support, as she also felt her shirt become shorter and better fitting. Instead of her professional look, Jenna’s V-neck showed off her cleavage slightly. With this change, she could also feel her underwear changing in shape as her boxers became a matching black thong that wedged itself between her cheeks. On her legs, the dress pants she had still been wearing, shrank to fit her new height, while also becoming tight black leggings that had been left over from ten pounds ago. Her shoes were next to change as they lost their professional quality, changing into simple black flats.

With the changes coming to an end, Jenna was left sitting in stunned silence as Kyle continued to pack up the board and pieces.

“It was great playing with you. If you ever manage to make it back here to America, I’d be happy to play again. Until then, maybe I’ll get bored with your life, maybe not. Either way, I have the option to change.” Kyle laughed as he walked away

Jenna didn’t even respond to this jab, instead trying to work her way through the information overload she had just received. Gone was all of her work to gain promotions, or even graduate, while she was left trying to now pick up the pieces of the life that Jenna had so unkindly offloaded onto her.

As Jenna continued to zone out and stare off into space, an older man sat down across from her with a smile.

“Sorry to bother you, but will you be playing anymore? Me and my friend here could use the table if you’re done with it?” the man asked hopefully

“Oh umm…yes, I’m done thank you.” Jenna answered, getting up from the table and seeing the second man beside her

Even though the man wasn’t all that large, he still towered over Jenna, and she felt herself feeling new feelings of intimidation. Walking out of the park, Jenna only hoped that her new parents might give her a second chance, but with how much her predecessor had screwed up, she knew that there was little hope of that.

The End