A Simple Bet

by: doctorpluto



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A Simple Bet "You have got to be kidding." Tony had just finished his second drink in the smoky bar as he listened to his friend speak. He leaned back in his chair as his friend spoke. "No, dude. I'm serious." the auburn- haired young man took a swallow from his glass. "I bet you ten dollars for each piece of clothing that you're too shy to cross-dress. Tony laughed, the cigarette smoke in the air stinging his nostrils. "How much are you offering, Chet?" "Well..." Chet added up in his head. "The stockings are one piece, then the dress, apron and necklace... That's forty bucks right there." He wiped his mouth on the sleeve of his jacket. "And the shoes are another ten, and if you wear the whole thing a week, you'll get another two- hundred." Tony took a breath in through his teeth, not sure what to think of getting 250 dollars just for wearing drag. He drained his third glass of lager and wiped the condensation off on his napkin. "I'll do it." He said. "I figured you would." Chet said with a chuckle. "Bet starts tomorrow; I'll drop the outfit off later tonight." He raised his glass. "Deal?" Tony chuckled. His olive-skinned nostrils flared, his brow furrowed. He raised his glass to Chet's. "It's a deal, you perv." -- The first day of the bet came and Tony found himself going to work with a black lace bra and panties on under his uniform. The dark brown nylons Chet picked out for him were hidden well under his dress pants, but throughout the day he felt odd. He scooted and turned in his chair in an attempt to get comfy. His hips felt funny. He looked up over the rows of cubicles to make sure nobody was looking, and then he dug his shaking hands under his pants and probed around with his fingers. Beneath the cotton lace panties and the nylon, his hips felt bigger, softer. The seat of his pants felt tighter as well, and his chest felt tingly. That was the only way to really describe it, a tingly heat that flared up every so often. Tony thumped his heel against the chair as he tried to keep his mind on his work. The hours crawled by and Tony struggled to get anything done. If it wasn't his pants feeling too tight on his hips, it was his chest feeling tender and sensitive under his shirt. And if it wasn't that, it was his nylons bunching up under his pants. Work let out and he was almost happy to come home and change into the full outfit. He locked the door to his apartment behind him and shut the blinds for good measure. He had it laid out on his bed: A plum purple 50's style swing dress with a black stripe around the waist, a frilly white apron, pearl necklace and a pair of high-heeled pumps the same plum color as the dress. The young man exhaled through his nose and thought about the money as he took off his tie and work shirt and threw them to the floor in a pile. His belt and black trousers joined them a moment later as he took the dress. It was a nice dress, at least; silky smooth, glossy satin. He slipped it on over his head, feeling the sleek fabric caress his swarthy skin. He smoothed it down, letting the knee-length skirt flow around his muscular legs. He did a little twirl in front of his mirror, giggling at the sight of the outfit on his lanky frame. "I look ridiculous." Tony smiled, more than a bit amused at his reflection. He plopped down on the bed, sticking his legs in the air. He rubbed his paw up and down his nylon-clad legs. Savoring the cool, soft fabric on his legs, the way the fully-fashioned style soles looked on his soft feet... He caught himself. Why was he enjoying the stockings so much? He sat up and pulled the heels on, pushing that particular thought to the back of his mind. He stood, wobbling in the hells until he got his balance right, and took the apron. "An apron isn't really women's clothing, but whatever..." Tony whispered to himself as he put it on and tied it good and tight in back. He had just put the pearls on when he heard a knock on the door. "Come in, Chet." His friend walked in and bit his lip trying to suppress laughter at the sight of his friend dolled up. "Oh man, you actually did it..." Chet said in a lilting, triumphant tone. "Yeah yeah..." Tony rolled his deep yellow eyes as he walked unsteadily in his heels towards his friend. "Where's my money?" Chet hummed a bit as he counted out forty dollars, plus ten for the shoes, and held it out for his friend. Tony snatched the bills from his paw and the two busted out laughing. "Okay..." Tony said, rolling his brown eyes. "I guess if I make it to Saturday with this crap on, I'll get the 200?" "Exactly," Chet smiled. The sight of his friend, straight-as-a-razor Tony Bello, in drag was worth 50 bucks. Chet pulled his phone out. "Strike a pose, little lady." And Tony put his hands on his cheeks and kicked his leg up, making the goofiest face he could envision as Chet's phone snapped a picture with a soft click. "Totally sharing that," Chet said with a toothy grin. Tony grinned at him friend sheepishly. What was even his intention? Was it to embarrass him? Was he getting off to it somehow? "Alright, I gotta go," Chet said as he headed out the door, hands in the pockets of his hoodie. Tony couldn't quite understand why, but a part of him was sad that his friend had to leave so soon. Day two of the wager came around and Chet brought Tony over to his place. It was a small house, but it looked pretty cozy with its red brick walls and white picket fence. The little hairs on his back bristled as Chet held his arm as they walked up the wooden porch steps. "Dude, I get that I look like a 50's girl, but do you have to lead me around like one?" Chet laughed. "What, you'll dress up for me. But me escorting you, that's where you draw the line?" Tony just rolled his eyes as they walked in. Chet led him to a couch in front of the TV and sat him down. "You can take the shoes off, we're inside." "Thanks," Tony said, kicking the hells off and wiggling his aching toes. "Those heels are murder on my feet." "Can I get you anything?" Chet said, going into the kitchen. "I'm good," Tony said as he looked over the den and couldn't help but frown. Magazines and paperbacks lying all over the coffee table and floor, stains in the rug, a floor that hasn't been swept in ages. Tony's nostrils flared as he took in the smell, sweat and dust. "This place is a mess..." He muttered to himself. "How does Chinese sound?" Chet said from the kitchen, getting the black plastic phone off the hook. "How about I cook something?" Tony said as he stood up. "Make some real food?" Chet was more than a little surprised to see Tony stroll so purposefully to the stovetop, his dress flowing with every step. He got out some frozen salmon and laid it out, and then he set out some onions, some celery and carrots to cut up while it thawed. He hadn't read the recipe, only knowing it by watching his mother make it, but it was enough. Chet watched his friend cut the vegetables, season the fish with salt and lemon pepper, and mix all of it together in a pan with some oil. "You've been dressed as a woman for only two days and you're already in the kitchen," Chet said with a chuckle. Tony just smiled as he worked. He would be the one laughing when he collected his money at the end of the week, yes sir. And on top of that, he looked damn good in those nylons and... Tony stopped himself. He focused on the cooking, ordering himself not to think of the outfit. He would make the salmon and not think at all how his butt looked so firm and shapely under the dress. He finished the dish: salmon pan-fried in olive oil with a mirepoix. Chet sat at the table with his eyes closed, breathing the scent in. Tony served his plate first before sitting down to eat himself, he watched as his friend took the first bite. Chet put a forkful of salmon in his mouth and his blue eyes snapped wide open. "Oh, my..." Tony looked at him, watching his reaction closely. "Is it good?" "It is amazing," Chet said, immediately taking another bite. "When did you learn to cook?" "I cook for myself all the time." Tony said with a smile as he watched his friend eat. Some part of him was happy Chet was eating something healthy for once. He smiled at Chet and he smiled back, wiping a bit of sauce off his thin, pale lips. Tony wished he used the napkin instead of his sleeve, but he would work on that later. And there it was again, his mind wandering. "Something wrong, buddy?" Chet said, snapping his friend out of it. "Erm... No, I was just thinking about something," Tony said, prodding his meal with his fork. "Like what?" Chet looked at him, running his fingertip along the rim of his glass. "What do you like in a girl?" Tony said, reaching down with his other arm to adjust his stockings. Maybe he could talk Chet into throwing in a garter belt for anther ten bucks, and then maybe they would stay in place a little better. Chet's fair-skinned face was flushed. He smiled awkwardly. "Well, I like a girl who's curvy," he said, taking another bite of salmon. "Shapely legs, nice hair, a good personality," Chet took a drink from his glass. "A gal you'd think about coming home to and get excited about it." Tony nodded, and thought that it was fortunate that he was close to the ideal laid out by his friend. There was something comforting in knowing that Chet would find him attractive if he were a woman. He wasn't sure why he felt that way, though. On the morning of the third day, Tony called in sick. He had woken up feeling weird all over, for lack of a better way to describe it to his boss. He felt an odd sort of hot tingling starting in his abdomen and flowing down between his legs, not to mention he felt... heavier around the hips and chest. As he put the phone back on the hook, Tony caught a glimpse of himself in the mirror and thought he was dreaming at first. He had breasts. They were small, barely A cups but they were breasts all the same, his nipples stood on the end of them, making them look just that much more pronounced. "The hell is going on?" He muttered under his breath. Even his body hair was different, thinner and less of it. Even his treasure trail, that long black strip of hair leading down to his manhood, was gone. He ran two fingers down his midsection, he was never exactly ripped but he could tell that some of his muscle definition had vanished. His arms were very much softer, smoother, almost curvy. He made a mental note to exercise more over the weekend as he lay back on the sheets and watched a program about hummingbirds. On the fourth day, Tony's shift ended early and he thanked the universe and every deity in it for that. His pants were too big in the waist and too tight in the hips after fitting just fine for the longest. His nipples were so sensitive he couldn't take his mind off them or the bra under his white button-up. And worst of all, his crotch was buzzing red- hot all day long. Every minute of every hour it went from being rock- hard to too sore for Tony to even sit with his legs closed. He fumed and fondled himself the entire drive home and he started undoing his fly the instant he stepped into his apartment. He kicked his khaki work pants off and fell back onto the bed, his member fully erect and feeling like it was burning a hole in his boxer briefs. He began stroking almost without thinking, pumping up and down, faster and harder with no further thought. He thought about seeing a shapely young dark-haired lady in the outfit he was in. She had bows in her red fur, black lace underwear and long legs with stockings. She had that come-hither look in her green eyes and Richard muttered a suitable name for her under his breath as he stroked himself. As his climax approached, his mind abruptly turned from being attracted to the woman to simply being her. He saw himself in her place as a big, strong Italian-American stud took her and bred her deep and hard. It was just a mental image, but it was too much. He climaxed loud and messily, feeling a mix of gratification and confusion as he lay there panting. What did he just do? What the hell was that all about? It felt wrong, but at the same time he wanted to take that fantasy further. He lay in bed for the rest of the day, wondering and daydreaming about what happened to that pretty little woman. -- It was the evening of the fifth day and Tony knew he was going to win that bet. That was the only thing on his mind as he got out of bed, looked at himself in the mirror, and saw a pair of big, perky breasts. His breasts, perky C-cups right there on his chest. He blinked, blinked again, and touched them, bouncing them in his palms. "Son of a..." Then he looked in the mirror again and saw what was unmistakably a woman's face. It was his face, with big doe eyes and smooth cheeks and a soft chin. His lips curled in a perplexed sneer as he studied himself. His hair had darkened and grew longer, into shoulder-length curls so soft and silky the hair looked like it spent the last day at a salon. Tony didn't know what was going on, but he had ideas. He made a mental note to punch Chet and also get a haircut as he strolled over to the TV. He breathed a long, tired sigh through his nostrils as he turned it on to a bridal show. They interviewed a recently married couple as they planned their wedding. Tony found himself looking more and more at the woman as she tried on her wedding dress. It really was quite gorgeous to Tony, flowing white satin down to the lady's ankles, matching elbow length gloves, and the low-cut neckline did such a good job supporting her perky bust. Tony crossed her...his nylon-clad legs and watched. There was something about the dress, how elegant she looked in it, how happy she was to put it on and show it to her husband that made Tony smile. A dress was so much more stylish than a tux, so much can be done on a dress but you see one tuxedo and you've seen them all. He really wished he could wear something that pretty when he got married. Tony stroked his cheek in thought as the show cut to a commercial for orange juice. Maybe he should settle down, the couple on TV looked so happy after all. Maybe Tony just needed to find a nice, strong... spouse to treat her... him right. Something was wrong. He shook his head. "I need to sleep," he muttered to herself...himself. He was confused, no doubt tired from work. The whole thing about the bet and getting back at Chet could wait. -- Friday had come and Tony had pretty much won in his mind. He woke up and put his bra on, marveling at how snug it had felt since yesterday. Time to move up a size, no wait... he wouldn't have to because the stupid, stupid bet ended today. It ended today and he could collect his money. He stepped into the lace panties and discovered that something was missing. No bulge in front, none at all. Tony cursed under his breath; oh he was definitely going to punch Chet's lights out when he got his money. He reached down the front of his panties and nearly hit the ceiling when his hand grazed his new, very sensitive womanhood. Just brushing over its lips felt like an electric current flashed through his spine. It was weird, it was unwanted... it felt really good. He wanted to explore it, try it out. But Chet was coming over soon and how awkward would that be? She... no he took in a deep breath and ordered himself not to touch it. As he pulled his stockings on, he looked at himself in the mirror, catching a glimpse of a classy young lady staring back at him. Perfectly curvy legs tightly nestled under the nylons, supple olive- toned skin that showed up her deep brown eyes and silky black hair perfectly. "What the hell did Chet even do?" she... he muttered under his breath. There was a knock on the door, payday for Tony. He strolled over in the most brusque, masculine walk his heels would allow him and swung open the door, fighting the temptation to just pop that son of a bitch right on the nose and let him keep his stupid damn money. Chet had a smug little grin on his face and Tony just stood there fuming in silence for a good couple of seconds. "You look nice today," he said smirking. "Shut up," sneered. "Well..." Chet said, his hands in the pockets of his jeans. "You're about to win the bet." "What do you mean about to? It's Friday, I'm in drag. Fork it over." Tony balled a fist, gripping the doorknob like it was Chet's neck. Chet just chuckled, pushing past the former man into the apartment. "You'll win the bet if you put one last thing on, I promise." "And you'll undo whatever... this is?" Tony said, almost shouting as he pointed at his well... womanly body. "Sure, if you want." Chet held out a ring, just a regular gold ring with no markings or embezzlements, just a ring. "Just slip this on, and you'll win." Tony took it, hesitating. It was such a delicate little thing, shiny and thin, and really quite elegant. It was simple in design, but it exuded femininity. He breathed a long, low sigh through his nose as he slid it on. "Think of the money," he repeated in his mind. And no sooner than when the ring fit all the way on his finger did he... no she receive a flash of insight. It was like a light being flipped on in her mind. It all added up, the dress, the changes, the ring. Tony knew what was going on, oh yes. "You, you want to marry me?" Chet nodded, caressing her chin. "Absolutely. You and nobody else, Tanya." "Oh Chet..." she said with a breathy sigh. "Of course I will!" And why wouldn't she? He was just so handsome, with his soft green eyes and his smile. His copper hair was so soft and shiny, his car was nice, his job was even nicer. Tanya threw her arms around him, their tongues dancing together as they kissed long and deep. Chet was the first to break the kiss, his hand trailing down to Tanya's rump. Such a naughty boy he was. "Now why don't you make us breakfast and we can plan our wedding?" Tanya's eyes misted up as she smiled. "Of course hun, I have so many things I want to do. It'll be our special day!" Chet let the eager woman lead him into the kitchen where he pulled up a chair and watched her cook a full breakfast; it was like poetry watching her. "I'm such a lucky guy," Chet said, and Tanya shot him a knowing smile as she fried eggs the way her mother taught: over easy with paprika and salt. As they ate, Tanya described in minute detail her perfect wedding as Chet listened. It was her big day, and they would make it special. -- It'd been a year since the honey moon, almost to the day. Tanya swept the floor in the den, taking breaks to watch her shows every time the commercials ended. The house was much nicer now, tidier and the walls repainted a nice cherry red. It was a sunny summer afternoon so she had the air conditioning on, and every so often she would pass over a vent and it would blow her dress up and Chet would look at her butt. Not that she minded, every time he gawked at her, every time he called her pretty... it made it all worth it. She sat down next to him on the couch, kicking her heels off. "Been on my feet all day hon," Tanya said as she wiggled her toes beneath her fully-fashioned pewter gray stockings. And as a good husband should, Chet scooted over to her on the couch and attentively began to massage them, showing great care as he tenderly knead and rubbed her nylon-clad feet. "Oh thank you Chet..." Tanya moaned, "Just what the doctor ordered." Chet just smirked as he kept massaging, putting more attention into every soft curve of her feet. He brought one of her soles to his lips, kissing it softly, then going back to work on them, she had a lot of tension in them. "Oh Chet..." she moaned. Before long, he was on top of Tanya. She reached under her dress and rolled her panties down, he unzipped his fly. They kissed, time seemed to stand still. Chet reached under her dress and stuck a finger in her waiting folds, nice and moist; she blushed and smiled at him. And so he thrust into her, slowly at first, picking up speed with each stroke into her. Tanya growled lustily as she hooked her arms around him, bucking and grinding against his girthy member. "Oh honey... honey..." Tanya moaned over and over as he pumped away at her, kicking her stocking feet against the sofa cushions. He leaned in and playfully nipped at the supple skin of her neck, kissing up and down her cheek as their climaxes neared. Tanya ran her hands up and down his back, kissing him deep and wet as their tongues danced. He came first, just as he pulled out. Her little gray dress spattered with his seed. She followed almost immediately after, her musky sex running down into the wadded up pair of cotton panties around her thighs. "How about we call in for takeout?" Chet said, panting. "It'd give us more time..." "Takeout sounds great." Tanya smiled. Oh yes, it was worth it.

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