Sissy Candy Pt. 01

This story is currently a work in progress. This posting includes Chapters 1 and 2. Chapter 3 has been completed, but not much beyond that yet. Please leave feedback. It encourages me to write more - Tawny!

Sissy Candy

The Rise and Fall of a Sissy!

by Tawny Suede

Chapter 1 - Boy, You'll Feel Like a Woman Tonight!

"Just relax kid, this is going to hurt a bit!" growled Uncle Mike as he slowly pushed forward.

And it did! Oh fuck, the pain was intense. Nineteen year old Candy squealed and his eyes bugged out and he began to cry as Uncle Mike's thick cock head pushed past his tight anal sphincter and slid slowly up his well lubed pussy chute!

Candy stifled those cries as much as he could. And Uncle Mike's large hand clasped tightly over his mouth.

The sounds of his fucking were muffled so that they did not rouse the neighbours, but the sobs themselves did not stop. Tears poured from Candy's eyes. He bucked and thrashed and tried to pull away from his uncle. But he was a slim young man, barely larger than a small boy, naked, on all fours with his ass raised and held firmly in the grasp of the much older man who was huge and hairy and powerful. Uncle Mike's powerful furred legs held the boy steady, and his arms gripped Candy, one on the mouth and the other on his rounded ass, as Uncle Mike continued to push his large cock into his nephew's beautiful and oh-so-fucking-tight asshole!

Candy had wanted this, had needed this. He knew it would hurt, this first time. But god fuck almighty, he had never dreamed it would hurt this much! He tried to pull away. He HAD to get away. But Uncle Mike held him firm and continued to push his large cock into the femboi's ass. "You wanted this kiddo. It's gonna hurt this once, but after this you are going to be begging for my cock - any cock - in your ass on a regular basis!"

Earlier that morning......

Kenny Spence threw up for a second time, kneeling beside the toilet bowl. Thankfully his hair had been trimmed back and was not in the way. He had kept his hair long until a couple days ago, when he went to a stylist across town and had it cut special for today.

The queasiness did not leave his stomach. His nerves were on edge. His stomach would not settle down until the day was done. Until the deed was done. Until he was no longer a virgin.

Kenny had planned for this day, ever since his parents had announced that they would be taking a trip to Europe during the summer. They had told him this over breakfast three months earlier. Kenny had butterflies in his stomach, and an erect penis in his panties every day since then.

Kenny looked at himself carefully in the mirror. He shook his head and his newly trimmed hair bobbed and shook but fell back into place pleasingly. He'd had it trimmed into a more feminine cut, and had the ends dyed a lighter blonde than his own normal colour. He liked the contrast of the darker roots and the lighter ends. He had also had his eyebrows plucked into feminine arches and had them dyed darker. It was a daring look for him, but it was one more step toward releasing his inner sissy.

Kenny's sister Constance had started attending college on a basketball scholarship almost two years earlier. While she came home to visit occasionally, she was going to be spending this summer with her college team, practising all summer long! Kenny would be all alone while his parents were away for almost two months. However his parent's had asked Kenny's father's brother to look in on him from time to time.

Kenny carefully applied his makeup, ever so lightly. He wanted just a hint of femininity. A touch of pale pink eye shadow and a touch of mascara. And just the faintest of lipstick. He had been practising with makeup for years, first with stuff he had borrowed from his sister and mother, then with makeup he had daringly purchased on his own.

Kenny had been a disappointment to his father. A big disappointment. Edward "Big Ted" Spence was a burly man. He had been a linebacker during his high school and college days, a big thick man who stood tall and wide. He had married one of the college cheerleaders, a small petite girl with large breasts (for her size) and a bit dim of mind, but a good woman.

Kenny looked at the skimpy bikini lying on the bed that he had bought just for today. He had tried on the swimsuits his sister had left behind, but was not satisfied with any of them. His sister was much bigger than him, so he had bought his own from a store across town. He would put on the bikini just before going outside, otherwise it would be stained with all of his precum. His boi clitty, as he had come to think of his small penis, was rigid from the anticipation.

Ted and Stacey's first child had been a girl, and Kenny had come along two and a half years later. However, sister Connie had inherited her dad's height and athletic abilities. Kenny had taken after his mother - small and thin of stature and not the quickest of intelligence.

Kenny stepped into the mules he had bought for lounging around the back yard pool. They had two inch cork heels. He had worn them several times already and was quite comfortable walking in them.

While Ted had taken his daughter to softball, swimming, basketball and various other competitions that she excelled at, Kenny had mostly stayed at home reading and watching tv and being a loner. His mother had doted on him. In the eyes of the father, the boy was soft.

Kenny opened his cigarette pack and pulled out one cigarette. He posed in front of his full length bedroom mirror, putting his weight on one foot, and then the other. He looked sexy, didn't he? A small pretty boy, naked and hairless, with a small erect clitty moist with precum pooling at his peehole. Pretty. That's what he was. That's what he wanted to be.

He had known from a young age that he was not like the other boys. He wanted to play with the girls. He wanted to be like the girls. He had snuck into his sister's room when she was at practise and had lain on her bed, smelling her sheets, and her clothes. His mother had caught him, but she never stopped him. She had understood.

Over time he had started trying on her clothes. When he was old enough, he always got erections when he touched any of her clothing. The first time he had put on her stockings and a pair of her panties, his penis had throbbed and he had ejaculated into those panties, cumming and cumming and cumming. Sobbing and sobbing and sobbing his shame, and his relief.

Stacey had found him crying and had helped him wash those panties. They never talked about the incident, but he knew that she knew. And if she knew and said nothing, then this couldn't be wrong, could it?

He lit the cigarette and inhaled. Funny, he had always thought of smoking as disgusting. But when he was wearing makeup and stockings, a cigarette was irresistible. The sight of his own lipstick on the filter always made him so very hard. He had jerked off many times while just staring at filters coloured with his own lipstick.

He used a tissue to dry off the tip of his clittie, careful not to stimulate himself more than his wild imagination was already doing.

He looked at the clock. Half an hour. An hour at most, before Uncle Mike arrived.

From a very young age, Kenny had been infatuated by his Uncle Mike. His father's brother had given him more attention as a child than his own father ever had. While Ted had given all his attention to sister Connie, Mike had been the one to take Kenny to the zoo, and they had spent a lot of time reading and watching tv and swimming together in the pool.

One of those times in the pool, Mike had come up behind Kenny and hugged him and then lifted him from the pool. When he did, Kenny could feel something long and hard pressing briefly into his buttocks. And from that moment, Kenny's mind had been filled with quite different thoughts about his uncle.

When Kenny passed into puberty, his dressup became more serious. He regularly wore panties and stockings when no one else was home. His sister's were too large, but he found he was close enough in size to his mother, and there always seemed to be new pairs in her drawers for him to try on.

At school he was a loner and so never engaged in the conversations with the other boys about the girls and what they would like to do with them, or had done with them, on dates. He never thought of dating the girls. He wanted to hang out with the cool girls, but was too shy to approach them. He did find himself checking out the boys though, and found himself wondering if any of them had something in their shorts as large as what he believed Uncle Mike had!

Kenny's parents had been gone for a week now. His sister Connie was almost a continent away. He was alone in the house. School was over. His high school days were over. They had celebrated his eighteenth birthday just before they went away. But he had no idea what he would do with his future. His grades were not good enough to get him in to college. He was not really bright enough, and he didn't really care. All of his thoughts were on his dressing. He just wanted to be a pretty boy. He just wanted to be a pretty sissy, whatever that entailed.

His uncle Mike had dropped by the house three times the past week. Each time Mike had immediately changed into his swim trunks and then cooled off in the back yard pool. Afterwards they had shared pizza or gone out for burgers. Uncle Mike had talked about his other weekly commitments and they had agreed that he would be dropping over two nights a week plus on Saturdays for awhile.

Kenny put on his pink bikini, top and bottoms. He gathered up his cigarette package and two women's magazines and went to the kitchen where he grabbed a wine cooler from the fridge. He went outside to the pool area and spread his towel on the grass. He lay on his stomach and read the magazines while he smoked and drank his cooler and waited.....

Ten minutes later he heard the front door open and Uncle Mike yelled out, "Kenny I'm here!" Uncle Mike had to change into his swim trunks before he appeared. Kenny trembled in excitement. The time had finally arrived.

Kenny trembled with anticipation as a few minutes later, Uncle Mike emerged from the house. Kenny leant up on on his one elbow and smiled, but Uncle Mike was paying no attention to the lad as he trotted to the edge of the pool and dove in. As per his usual routine he then proceeded to swim a dozen or more strong lengths of the pool, barely lifting his head from the water.

Kenny stood up and grabbed the extra towel. Uncle Mike finished his laps and swam to the edge of the pool where with a mighty heave he drew himself out of the water and onto his feet. Water dripping in his eyes he reached for the towel Kenny handed him, wiped off his face and then finally looked at his nephew. "Kenny?!? What...?"

Kenny smiled softly, his head tilted down. "What are you wearing?" was the next thing Uncle Mike said, though almost at the same time he also said, "What have you done with your hair?"

Kenny bit his lip nervously, his lipstick staining his teeth. He shifted his weight from one foot to the other, pushing his hips out slightly, and slowly turned. "So, um... what do you think, Uncle Mike?" he asked in a faltering voice.

"I think YOU like this!" the older man said grinning his eyes looking at Kenny's groin where the outline of Kenny's very hard cock was visible, trapped in the tight pink bottoms, with a large moisture stain. Kenny blushed and moved his hands to cover his peepee.

Uncle Mike took his hands and stopped him. He drew the young man to him and hugged him tight. Kenny let out a long breath and relaxed. Mike pushed him back a bit and took another look. "What do I think? I think you look great. I think you look incredibly sexy. And I think it is darn well about time!" Mike drew Kenny back into his arms again, but this time he tilted the lad's face up and kissed him, very hard and very very long.

Kenny melted as his uncle's tongue invaded his mouth. He had never been kissed meaningfully on the lips before - just pecks from his mom and his sister. But this! Oh, it was so wonderful to have a strong man holding him, and sucking on his lips and his tongue. Kenny kissed back fervently. Oh he had waited for this... wanted for this... for so long!

"Oh wow!" exclaimed Kenny, as the two finally drew apart. "Did... did I do that right?"

"The kissing? Sure kiddo, you did fine. With a bit more practise, you'll be great!"

This brought a beaming smile to Kenny's face and he stepped back into his uncle's arms. "Not just yet though," said his uncle. "Why don't you go grab me a beer while I finish drying off."

Kenny pouted, but he walked back towards the house. Mike admired his nephew's body as he walked. The corked heels, though not very tall, did accentuate the young man's legs. "That's a nice ass, you have their Kenny!" Kenny gave his ass an exaggerated sway for the last few steps into the house. Before grabbing the beer from the fridge, Kenny went to his bedroom and quickly touched up his makeup and especially his lipstick, coating his lips a bit heavier this time. He had loved the feel of his waxed lips sliding over those of his uncle. So erotic! His clitty pulsed as he imagined what the next hour might hold!

He returned to the back yard, beer bottle and glass in hand. When he reached the back yard table, his uncle had lit a cigar and was leaning back. Mike was a tall muscular man with very little fat around his midriff. His body was very hairy. Mike put his cigar down as Kenny handed him the beer, but shook his head to the glass. He put his other hand around Kenny's waist and pulled the cute young man to sit down on his thigh.

Mike leant forward and kissed his nephew hungrily. Kenny eagerly returned the kiss, at first repulsed by the flavour of the cigar in his uncle's mouth, but then realizing that this was the flavour of a true man!

Kenny sighed and leaned his head against his uncle's shoulder as Mike drew from the beer then took a drag on his cigar. Kenny ran his hand through the thick hair that matted his uncle's chest. His hand strummed along the thick muscles of the chest. Kenny's dicklette strained in his panties and the pre-cum stain spread!

Mike's free hand stroked along Kenny's back. The sissy lad shivered and moaned. Mike smiled and kissed Kenny on the forehead. Kenny raised his head and mashed his lips to his uncle's feeling the older man's tongue forcefully probe his mouth again as Kenny whimpered and eagerly sucked on the invader. Almost unconciously, Kenny's hand moved to his uncle's lap and he pressed against the thick member which was half erect in the swim trunks.

"You are the eager little sissy boy, aren't you?" smiled the older man. "You know, if I hadn't had my share of younger seaman encounters when I was in the navy, you might have found me reacting quite differently! But.... " said Mike with a grin as his strong arms lifted Kenny in the air.

Kenny squealed as his uncle lifted him, and then set him back down. Now Kenny was sitting across both of his uncle's thighs, face to face with his idol. Kenny's bottom rested firmly atop his uncle's hot dick that was now fully rampant in his shorts. Kenny moaned as he moved his ass back and forth across that thick slab of meat. Kenny knew what he wanted, and now he knew that before the day was over... heck before the hour was over... he would finally get what he wanted.

He threw his arms around his uncle's neck and kissed him hungrily, wantonly, eagerly.

"Easy honey... go easy. We have all day. We have all night too! Mmmm... you taste so sweet baby!" Kenny drew back and blushed. "I don't think we can keep calling you Kenny when you are dressed like this, can we?"

Kenny shook his head but remained silent. "Do you have a girl name for yourself when you are dressed?" Kenny nodded his head. "And what is that? What should I be calling you?" persisted Mike.

"Candy!" whispered Kenny.

"I couldn't hear you sweetie. What's your name?"

"Candy!" said the young lad more loudly. "My name is Candy when I'm dressed!"

"Well, Candy, I'm pleased to meet you. Why don't you get up and get me another beer!"

Kenny... no, now Candy... Candy eagerly hopped to the kitchen to get his uncle another beer. As he passed him, he gave him a playful spank on the ass. He arched his back and wiggled his ass at him briefly, noticing him grip his cock through his trunks.

He again fixed his lipstick but this time brought his lipstick case outside with him. He handed his uncle the beer, then went to where his towel was spread on the ground to retrieve his cigarette pack. He sat down in the other chair and lit a cigarette, and inhaled. He was lost in the moment, briefly. His uncle said, "I didn't know you smoked!"

Candy smiled as he tapped off his ash. "Kenny doesn't smoke, but Candy thinks its sexy!" he said.

Mike noticed his nephew staring at the filter. "You get off on seeing your lipstick there, don't you?"

Candy smiled shyly. "Uh huh" Then he added, "You weren't surprised to see me dressed like this?"

Uncle Mike exhaled his own cigar smoke. "Kiddo, I've watched you grow up. Your mother has told me about some of your dress up sessions. I knew it was only a matter of time before you would realize just how different you were from the other boys!"

"Mama told you? Oh, my.... " tears started to form in Candy's eyes. Mike took Candy's hand and squeezed it.

"Don't worry, Candy. Your mother is your biggest fan. She only wants what is best for you. And if this is what you want..." Mike leaned back and spread his legs, grinning... "if THIS is what you want" he said gripping his cock... "then your mother is all for it!"

"That's one reason your parents went away for several weeks. Your mother figured you needed some alone time to explore your Candy side! It wasn't hard for her to convince your Dad to take a long vacation."

Candy stubbed out his cigarette and again sat on his uncle's lap. He kissed him briefly and then nestled his head in his neck, kissing him there. He inhaled the strong masculine scent. Even after his dip in the pool, Uncle Mike still smelled of the heavy sweat he had worked up on the construction site all day under the hot sun.

Mike reached down and cupped Candy's groin in his large hand. Candy moaned as he pressed his rigid dickie against Mike's palm. Mike seized Candy's penis and Candy moaned louder. "Oh, Uncle Mike! That feels so good!"

"Why don't we get this thing off of you?" said Mike, pulling at the string that held Candy's bikini bottom in place. He tossed the small piece of pink fabric to the ground.

Candy's penis stood up rigid. Mike took it in his hand again and Candy winced. "Oh, Uncle Mike!!" he cried as his tender dicklette throbbed in his uncle's hand. He could not help it! This was the first time anyone else had touched his cocklette. And it was his Uncle!!

Candy let out a frustrated yelp as his dicklette tensed and then shot his load of creamy spermies. He fired once, twice, three times... excited spurts that flew high in the air. Withe each ejection he screamed softly. Oh fuck, he was in heaven!!

Mike grinned as his sissy nephew's head threw back and his eyes widened. He had known Candy needed relief but he was definitely surprised at how little it had taken to trigger the little cream puff's orgasm!

Candy collapsed against his uncle, his lips seeking the older man's strong lips and once again Mike's tongue invaded his mouth. Candy purred with contentment.

"That was your first time?" asked Mike.

"Uh huh," said Candy. "I've had plenty of wet dreams already, and have jerked myself off a couple of times, but that's the first time I've ever had anyone else make me cum!"

"None of the girls in your class, or boys?"

"No. None of them. The girls just frighten me. I'm.... I'm not very brave! And the boys... well, I have to admit I like looking at them, but letting them touch me? No way. They're just boys! So.... so immature!"