Drinking Game (TG)

    Finn was an overworked art teacher at his local high school. He was beloved by the students but demands from the administration and parents had driven him to the edge. The once fun and cool teacher now were always tired and apprehensive. What was once a job filled with fun and passion was now depressing and stressful to Finn. His art department at school had little to no funding, it being cut year after year to continue increasing the sports budget. Even Finn's art club, which he used to help lead in statewide competitions had to end years ago, another byproduct of the school administration not caring about the arts. Even parents, which when he had first begun teaching, supported art, were complaining at school board meetings about art class and how it made their children gay or trans or whatever. To Finn, he was just tired and exhausted. He needed an escape, and so, for the first time in his life, the frustrated Finn found himself going to a bar! 

    Finn was totally out of his element. The place was filled with businessmen off work, or blue-collar workers taking the stress off. Finn, wearing a paint spattered jumper was definitely the odd person out. As he opened the door, every patron in the bar turned and stared at him, just like in the movies. Finn had been recommended this bar by his colleague, Cassidy, the P.E. teacher who told Finn it was a good, quiet place to rewind after work. Finn awkwardly walked up to the bar, sitting on a stool. The bartender didn't even look at Finn, busy cleaning glasses and serving other, most likely regular patrons. 

"C-Can..." Finn cleared his throat. "Can I get a drink?" Finn nervously asked. The bartender slowly and heavily walked down the bar, across from Finn. 

The bartender sighed, "What kind of drink?" Finn hadn't thought that far, but quickly replied in panic. 

"U-uh... a beer!" Finn stammered out a reply. 

Again, the bartender sighed. "What kind of beer?" 

"Don't worry Frank just get the guy something good, put it on my tab" an unknown voice called out, then a guy plopping down next to Finn. Finn looked at the guy.

"Oh, err thanks" Finn extended out his hand trying to thank the random guy. 

"Name's Andrew" the man took Finn's hand. 

"Name's Finn. Im sure you can tell but this is the first time I've been here... and well-"

"No need to over explain." Andrew chuckles as the bartender places a beer in front of the two guys. "Everyone here has been new at some point, well besides Frank, but you get what I mean" Finn nodded along as Andrew talked. Finn eyed the beer and carefully sipped on it. The slightly cold drink slightly burned going down. Finn had never been a drinker, but with how shitty everything was, Finn found himself sipping on the beer. "How is it kid?"

"Oh... well its different but not bad I suppose" Finn nursed the beer, Andrew drinking several in the time it took Finn to drink a single glass. 

    For the next few weeks, Finn headed to the bar after school, spending an hour or so chatting with Andrew before going home and grading and dealing with angry calls and emails from the administration or parents. The bar soon became Finn's only safe haven in the world, where he could just forget the outside world. 

    One day, as soon as Finn plopped down on his usual barstool Andrew hopping up next to him. "Yo Finn you ready for your initiation as a bar regular?" Andrew threw an arm around Finn. 

"Uhh... initiation what now?" Finn was a little confused. 

"Thats right. In order to become a regular, you have to defeat Frank in a drinking contest" Andrew said. 

"I mean that's fine. I don't want to impose..." Finn shifted on his stool a bit. 

"You won't be imposing at all! Hell, the guys will even pay for your uber home so you don't have to worry about being drunk." Finn wasn't exactly convinced by Andrew. "I'll let you in on a secret, Frank is a lightweight, literally everyone here has beaten him in the drinking contest. Finn mulled about, but as the rest of the patrons cheered him on Finn finally caved. 

"Alright fine. I guess I'll take on this challenge or whatever" Finn stood triumphantly, hoping to impress the guys. Maybe he could find a community for him, free from all the stress and complaints. 

"Awesome! Frank. Finn. Get ready!" Andrew stood and pulled a table into the center of the bar floor, a chair on either side of it. People gathered around as Frank appeared from behind the bar. 

"Well kid? You challenging me or what?" The gruff Frank spoke out. Finn nodded and the two sat across from one another at the makeshift table. Andrew and other patrons prepared a wide range of shot glass, filled with various liquors from behind the bar. "You better have gotten the cheap shit for this" Frank complained but had no intentions of stopping the little contest. Andrew and the other patrons cheered, as a shot was placed in front of each contestant. Finn looked down at the small clear glass of brownish liquid. By the time Finn looked up, Frank had already downed his first shot. "Another. Hit me" Frank tapped the table, another shot placed in front of him. "If you wanna win kid, you better start drinking." 

Finn finally picked up a glass, and sipped the liquid, wincing at the taste. He took another sip, the liquid burning his throat, but Finn powered through and finished his first shot glass, after Frank had finished two more. 

"I'm already ahead Finn. Think you can catch up?" Frank was already downing another one. 

Finn hunkered down and began drinking faster, the burning sensation spreading from his throat throughout his body. By the time Finn had taken his fifth shot, his vision was beginning to blur and wobble. 

Andrew smirked and began sliding Finn new shots, these however, filled with a distinctly different liquid than booze. This booze was bright orange and as Finn took the glass and brought it too his lips, taking a sip, his lips plumped up massively, the orange colour spreading over his lips in the form of orange lipstick. Downing the shot glass and slamming it down, Finn's entire face looked foreign than when he had brought the glass to his face. His face now looked like that of a woman's. Beyond the massively plump, orange painted lips, his features were soft, skin smoother with no facial hair. His nose had shrunk, eyes turning an alluring brown, a beauty mark right by the left one. As his lashes grew out into full volume, wrinkles began to appear around his eyes showing an increase in age, but these wrinkles were soon covered up by makeup. Orange eyeshadow and thick eyeliner hiding any signs of an older age. Finn's brows thinned out drastically. And lastly, his messy black hair was now a silky brown bob, perfectly framing his now older face. 

Finn grabbed another shot glass, having no clue what was going on with his face. His hand grasped around the shot glass of liquid, watching Frank down another shot easily. "So that's what ya guys are up to? Well as long as they work for the bar I don't give a shit." Finn's brain had been dulled by the liquor, and he barely understood the meaning of Frank's comment. With a slight shrug, Finn gulped down the next shot. Shivering a bit as the liquid ran down his throat, Finn's adams apple vanished, withering away and leading Finn to now have a milfy voice, perfect for alluring men and boys. His shoulders crunched inwards, each arm thinning out. As they did, the skin became creamier, losing hair, clearly kept up with lots of creams and lotions. His hands shrank down, each finger becoming long and slim, with a manicured, orange painted nail growing out on the end. Luckily, Finn's hands were still perfect for holding paintbrushes, but now excelled at wrapping around something else specifically. 

Frank let out a burp. "Sill up for it kid?" 

Finn blinked, "S-S-" Finn was a little confused by the voice escaping his lips. It sounded like that of an older, mature woman. But feeling a little drunk Finn kept talking. "Sure am Frank!" Finn let out a small hiccup and grasped the next shot glass, studying his hand for a bit, Finn couldn't exactly remember when he had painted his nails. But they did look cute. So Finn took another chug from the shot glass, to the cheers of Andrew and the other patrons! 

Finn slammed the shot glass down and felt a rumbling feeling throughout his body. Finn began to feel horny, and shifted in his seat as his cock began to grow in his pants. Underneath his shirt, his nipples grew hard and itchy, the more prominent nipples being surrounded by larger areolas. Fat and flesh began to grow underneath Finn's nipples, Finn in the middle of raising another shot glass, moaning out in pleasure, spilling the glass all over his shirt. 

"Ack! That's no-good Finn!" Andrew placed a hand on Finn's shoulder. "You should get changed out of that. Don't worry we got spare clothes in the back left from other patrons." Finn nodded and wobbly stood out, his chest slowly yet surely growing in size and sensitivity. Holding onto Andrew and the wall, Finn was lead into the back into a private room. Laid out was a green dress, white coat, and heels. It would clearly show off a lot, but it was better than a booze stained and smelling shirt. Finn stripped down, his chest wobbling as they hung free, still ballooning outwards. Sliding into the dress was easy enough, until Finn got to his chest. Looking down, Finn's chest was massive! Two heavy, sagging tits were siting where his flat chest had once been. Attaching the choker and tying the straps allowed the dress to barely cover his fat tits. Finn must've been hallucinating. He thought the liquor was playing tricks on his vision. Throwing on the white fur coat did help cover some, but Finn ignored the heels. His drunk ass would not be able to walk in those, even if they were cute... 

Finn wobbled back to the table, his chest jiggling and wobbling as he did. Finn sat down and instantly downed another shot, the growing crowed cheering, each member drinking their own drinks of course. Finn's waist narrowed down as the liquid hit his stomach. His waist cinching inwards while his stomach flattened up drastically. Finn grunted and moaned as his hips shot outwards, stretching the dress at the hips. With a crack they stopped widening at a shapely, and child birthing width. Finn struggled to sit up and grab new shot glasses. 

"Shooo much boossee" Finn moaned out, wrapping his hand around a shot glass, spilling some of its contents. But he managed to down the beverage. A rumbling in his lower body forced Finn to raise in his seat, fat rushing into his ass, raising Finn in his seat as his butt grew out larger and larger, jigglier and fatter. Underneath Finn now sat a fat ass, comfying up the seat for the drunker and drunker Finn. His thighs fattened up next, putting pressure and squeezing his hard cock. Each leg slimmed down, feet slimming down as well. 

Finn moaned out, and drunkenly reached for the shot glass. "Cooooomeee on gotta winsh!" Finn slurred out. His hand grasped around the shot glass and brought it up to his lips, hiccupping before downing the shot glass. Finn's cock was throbbing, spurting out pre cum, but with no release, Finn's cock began shrinking back towards his body. Finn let out a loud moan as his cock slinked back into a worn pussy, seeing years of use. And with that, Finn had someone fully become a woman. 

"Hey Finn! Pose for us!" Andrew whipped out his phone at the drunk Finn. Finn letting out a hiccup tried to give a sexy pose, but with her body it worked, Andrew taking one photo of the new woman. 

    Andrew looked at the photo and smiled. "Hey Finn, you're about to win, just one more drink to finish off" Andrew was grinning ear to ear, but Finn was far too gone, drunk to really comprehend. Andrew and a number of other guys headed into the back, Finn left sitting at the table, woozy and vision spinning. Frank got up and began cleaning up glasses.

"Congrats on winning kid. I look forward to working with your further" Frank said, grabbing stacks of empty shot glasses, all the while Finn smiling and giggling drunkenly. Finn sat there for a bit, looking around as other Patrons either left or went back to their drinks. Finn was feeling very hot and sweaty from the drunkenness and so he shed his coat, sweating sheening his body and glistening underneath the lights. 

Out of the corner of his blurry vision, Andrew returned with a glass filled with what looked like milk at a distance from Finn. The glass was placed in front of Finn. Finn looked at the tall glass filled to the brim with milk. 

"Thanksh" Finn slurred and picked up the stem of the glass. The glass of milk smelled awful, and was warm. "Ooo warm milk..." Finn brought the glass up to his lips and... began chugging the thick liquid. It was warm, and the taste was... salty. "What kinda cocktail is thish?" Finn hiccupped between gulps. 

"Oh just one of the bar's specials" Andrew held back laughter as Finn went back to guzzling the glass of patrons cum like it was the tastiest drink in the world. As the thick cum hit Finn's mouth and slid down his throat, the salty and hot cum sent sparks throughout Finn's alcohol addled mind. Finn's mind was in a rush. The taste of cum... was just so... TASTY! Finn eagerly chugged down the glass empty. 

"Anutha pleash!" Finn hiccupped his mind assaulted by the taste of the cum. The more and more his brain was wracked with cum, the more his entire mindset changed. Finn... no Finley, that was more accurate. That's right, why be a deadbeat art teacher when you could be a sexy, milfy vixen able to guzzle up all the cocks and cum one could want! Now dont get me wrong, Finley still remembered being an art teacher and such. It wasn't a total mind break. Finley's mind melt was interrupted when another glass of piping hot cum was set in front of her. Finley picked it up and eyed the glass. It looks so rich and creamy and tasty... Finley licked her plump lips and, began downing her second glass. Finishing it off with a satisfied moan Finley placed the glass on the table. 

    "Now about your payment..." Frank stepped forward. "All the shots plus those two house specials cost a lot." Frank and Andrew stood side to side while Finley gulped.

"That's right Finley" Andrew added. "Your tab adds up to like 100 thousand dollars" Finley almost fainted upon hearing how much she owed. 

"Don't worry though, you can work for me to pay it off" Frank smiles. "We've always needed a sexy vixen here to drum up business. So from here on out, ya work for me, every night till you pay off your debt." 

Finley trudged into the bar after a long day of teaching art, no one really questioning why their art teacher turned into a hot milf. Thats the public school system for you. Finley walked into the bar, wearing that green dress and coat, considering it was the only clothes she owned. 

"Ah good afternoon Finley" Andrew was sitting at the bar. Finley's heart skipped a beat, why was Andrew suddenly so... handsome and hunky? Finley sat at the stool next to him. "So Finley? Ready for work?"

"Yeah I suppose so" Finley muttered to herself. "What does my job even entail?"

"You'll just stay around the bar and drum up business" Frank walks up and gives both Andrew and Finley a glass of beer. It wasn't on the house, but Finley didn't know that. For the next several hours Finley tried her best to be friendly and flirt with patrons to get them to spend more. But in return all she received was pokes, pinches, and slaps to her shapely curves. Occasionally, a patron would stuff dollar bills down Finley's cleavage, the sweaty bills being given to Frank to pay for drinks and Finley's debt. In order to cope with all the harassment, Finley drank more and more, increasing her debt, but also getting drunk. 

It was closing time, besides Frank, only Finley and Andrew were at the bar. Finley was completely sloshed and was leaning over the bar, a half empty glass in her hands. She had been eyeing up Andrew all night, her lower lips feeling a little damp just being next to him.

"Are you two leaving our what?" Frank gruffly asked. 

"Yeah guess so" Andrew stood up and stretched, Finley almost falling over as her support moved. 

"Wait... *hic* Wherses yous goin?" Finley slurred. 

"Im going home. As should you." Andrew replied, somehow not drunk after drinking so much. "Ah but wait. You're wasted... Come home with me" 

"Forward basterd... *hic*" Finley giggled. "Okeys I go withs yoush!" Finley got up and wobbled over to Andrew, holding onto him as he lead her to his car, driving Finley and himself back to his house.  Finley stumbled into Andrew's home, collapsing on the couch, Andrew getting a great view up her dress. 

"Need anything Finley? A blanket? Some water?" Andrew asked, standing over Finley. Finley's vision was spinning, but all she saw was a total hunk in front of her. 

"All I needsh is you!" Finley moaned out, groping her breasts. 

"Heh? Me? You're way to drunk Finley, just rest up" Andrew placed a blanket next to Finley and went to his bedroom to prepare for the night. Finley hiccupped and looked at the blanket. The couch looked so uncomfortable and so, wobbly, Finley got up from the couch. She walked around Andrew's flat, opening the fridge and drenching down some much needed water. Gazing over at the closed door to Andrew's room, Finley licked her lips. And then she went in for the kill. 

Swinging the door open, Andrew caught Andrew in the middle of changing clothes. "W-Wait!? Finley!?" 

Finley rushed forward and pushed Andrew down onto the bed. "Shaddup" Finley said, with a hiccup. Finely's small hand wrapped around Andrew's cock and began to pump it. 

"Lets c-calm down Finley! You're way too drunk for this-" Andrew was cut off by a sloppy kiss. Finley's soft hand pumped up and down, Andrew's cock quickly hardening up. 

"Purrfect!" Finley broke off from the kiss and positioned herself lower, her massive bust resting on Andrew's crotch. "Letsh have fun" Finley took her tits out of her top and nestled Andrew's cock in between them. Andrew's head fell back, his hard cock enveloped in warm fat. Finley began to shift and massage Andrew's hard rock on with her tits. The warmth felt like two big warm water balloons rubbing up and down Andrew's cock satisfyingly. Finley's cleavage quickly got slick with sweat and pre-cum. Andrew look down at the act as it was happening: 

 "Fuck Finley... they feel great..." Andrew let out a moan. 

"Thanskh!" Finley giggled. which was interrupted by a hiccup. "Ive had my eyesh on you since the beginning" Finley admitted, keeping up the massage with her massive melons. Andrew clenched onto the sheets. 

"God damn... im already close" Andrew grunted, his cock throbbing eagerly for release. 

"Dontchu worry! Im a *hic* art teacher~ Paint all over my chest" Finley licked her lips and worked the cock harder. "My boobsh are a canvas for your cock!" 

Andrew let out a grunt and came, ropes of cum shooting all over Finley's chest, painting a piece of cum abstract art all over her fat tits. Finley collapsed and cuddled up with Andrew. 

"Sho... good..." she was already asleep, holding onto her man. 

Finley continued to work on paying off her debts. Spending every night at the bar, flirting and fucking patrons for money, while growing her debt due to drinking. But while she did whore her body out, she remained true to Andrew. Making sure her clients only came on her chest, painting a portrait of cum. And Finley always made sure to go home with Andrew and letting him fuck her. Every time Andrew's cock plowed her mature pussy, Finley would loudly moan out the names of famous artists in bliss. With another pussy full of Andrew's cum, Finley cuddled up with her man, now extremely happy she got to play that drinking game.