Sissy Candy Pt. 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"What about other men?" asked Uncle Mike.

Candy smiled. "No one has touched me. No one knows about Candy. But yeah... I do look at some older men and wonder what it would be like if they did touch me. I think about my history teacher, Mr. Clements a lot. And Mr. Jenkins who lives a few doors down. But I've never been brave enough to let them know I'm a sissy. And I always knew,..." Candy dropped his head shyly, "I've always wanted you to be the first man who knew about Candy."

"Well it looks like you have recovered from your little cummies!" said Mike looking at the stiffie in Candy's lap. "Perhaps it's time you returned the favour, huh?" Mike spread his legs and Candy could see the very distinct shape of his cock in his swim trunks. Candy slid off of his lap and knelt between Mike's legs. Mike lifted his ass from the chair and tried to peel his trunks down. But because they were wet, they resisted. He raised himself higher, and Candy eagerly grabbed the edges of the trunks and helped pull them down, and off. As he did, Mike's impressive thick cock bobbed inches from Candy's face.

"Ooooo... " moaned Candy as he touched the warm cock with his hand.

"Is this the first cock you've touched?"

"Other than my own, yes!" whispered Candy. "It's beautiful! So long, so thick, so warm!" he said as he stroked it lightly.

"Go ahead baby, give it a kiss, why don't you!"

Candy had wanted this for so long. Finally, he had a real hard stiff cock in his hands. He marvelled at how large it was, not like his three inch peenie. As he lightly stroked it, he watched precum burble from the peehole. He could not resist. He had to know what that tasted like. Candy's first touch of a cock on his tongue was to swipe at the precum and lick it into his mouth.

And then he did not stop. His tongue licked around the head of the cock. His tongue lapped along the sides and then... and then he sucked the head of the cock into his mouth and began to bob his head on the wonderful meaty shaft. He had never had a cock in his mouth before, but he had watched lots of videos online. He knew what he was supposed to do!

Mike stroked his head. "Oh yeah baby. Suck my cock with that sissy mouth. You're a cocksucker now honey. You are my cocksucker!"

A cocksucker! That was what he was now. He wasn't just a sissy in waiting. He had a cock in his mouth. He was a sissy cocksucker! Oh, he loved it! As he bobbed his head up and down the shaft, he also adored the wonderful dick with his hands. Then his hands found the heavy meaty balls and he knew he had to taste them.

As Candy pushed his uncle's thighs wider, Mike took one last puff on his cigar and stubbed out the remnant. He knew where his cute nephew was headed and he scooched forward so that his ass was on the very edge of the chair.

Candy lifted the cock out of the way and admired the large ball sac. If was large and very very hairy. Candy's face was just an inch away and then Mike grabbed his head and pushed Candy's face fully against his nuts. "Get in there good kid!" smiled his uncle.

Candy inhaled the full masculine scent of his uncle's balls. Oh god, he thought. This smells so wonderful! The balls were moist with Mike's manly sweat. Candy loved the thick odour! He swiped out his tongue and tasted the salty sweat captured by all the hairs. Then he eagerly lapped and lapped at the nuts. Hairs caught between his teeth as he continued licking. He swallowed sweat and hair and bliss!

But then Mike pulled his head away, bent the head of his cock down and pushed his dick back into Candy's mouth. Candy resumed sucking that glorious meat! He pushed his head as far down the cock as he could, eager to engulf it all... eager to pleasure his uncle!

"Go easy, Candy!" moaned his large uncle. "This is your first time. You're not going to be able to swallow my dick this time. There'll be plenty more chances for you to try!"

Candy popped the cock from his mouth and grinned. "We can do this again?"

"As many times as you want sweetie!" Mike leaned back and enjoyed the sensation and sight of his sissy nephew bobbing up and down on his cock, but soon Candy slowed. "I bet your mouth is getting tired, isn't it?"

"Uh huh" admitted Candy, setting back on his heels. He wiped his mouth with his hand. "But I really want to suck you off!"

"I want that too, sissy! But it can take quite a bit to get me to cum!" Mike rose and stood over Candy. "Open wide," he said. "And stick your tongue out" Mike lay the tip of his dick on his nephew's tongue and began to pump his cock. God, he thought, this was so fucking sexy. Candy's makeup was a bit of a mess now, but his nephew looked up at him adoringly with those big dark eyes and that oh so sweet and sexy mouth. It took just a minute and then he groaned, "Here it comes!" he grunted.

Mike watched as his first two strong spurts of cum shot into Candy's mouth. Then Mike pulled back and shot his next few ropes across Candy's face, one dollop landing square across his sissy nephew's left eye. Then Mike collapsed back in the chair.

Candy closed his mouth and for the first time tasted the cum of a strong man. The flavour was powerful. He swirled it in his mouth and then swallowed. Oh he loved it! He used his finger to wipe his eye clean. He made eye contact with his uncle who smiled as Candy slowly licked his finger clean. Then he leaned forward and took the tip of his uncle's wilting dick in his mouth and eagerly sucked the last few drops of cum from the burly man's piss slit.

He leaned back on his heels, his own dicklette incredibly rigid and smiled at his uncle. "Mmmmmmmm!"

"You liked?" smiled Mike!

"Oh yeah!" exclaimed Candy. "I'm a sissy cocksucker!" He clapped his hands together excitedly. "I want more!"

"Not right now, sweetie! I need to cool off again. Why don't you go order us a pizza while I do a few more laps!"

Candy pouted, stroking Mike's dick and trying to bring it back to life. Mike swatted the sissy's hand away, but he was grinning. "Go!" he told the sexy sissy. Candy wandered back into the house, looking over his shoulder and blowing a kiss at his uncle. Mike smiled back, then dived into the pool.

When the pizza was delivered, Mike gave Candy the cash and made him answer the door. Candy had put his bikini top and bottoms back on and wore his mother's robe over top, but he was still nervous. But all he got was a faintly puzzled look and a smile from the delivery boy.

Candy sipped a soda with his pizza while Mike had another beer. They sat on the couch while they ate, watching some silly sitcom. Candy sat right up against his uncle, constantly rubbing his body as they ate. At time's Mike would tousle Candy's hair, or put his arm around his waist and draw him closer for a brief kiss.

At one point Mike handed Candy a blue pill and told him to swallow it with some coke. "Viagra?" asked Candy.

"It's not mine. I got it from your dad's stash in his room. I don't need to take it but your father likes a bit of extra help. And you.... well, you're young enough not to need it, but I want to keep your sissy clitty rigid and on edge for the next few hours!" he grinned.

When they finished eating, Candy cleaned up the cans and pizza box. The sky was getting darker and the evening was cooler. The two lovers closed up the doors to the outside. Mike suggested that Candy change out of his swimsuit and sat down to watch tv as his nephew went to change.

Candy knew exactly what he wanted to wear next. As he opened drawers, he felt a bit light headed, and his heart seemed to be racing. And his dicklette was so very very hard!

He pulled out a pair of dark stockings and drew them up his legs, fastening them to a garter belt he had pilfered from his mother almost a year ago. He went to his mother's room and sat at her makeup table and darkened his eyes, using heavier eyeshadow. He borrowed Stacey's bright red lipstick. Much sluttier he thought gleefully! He then spritzed himself with some of his mother's perfume. In her closet he found a pair of four inch heels that he adored and had borrowed a few times already, so he was confident in them. Lastly he went to his sister's room and relieved her of a kimono that came down barely below his ass.

His cockette was almost painfully rigid as he strode back into the living room area where Mike was sitting naked, waiting on his nephew. Mike's eyes went wide as he Candy entered. "Fuck me!" he exclaimed.

"Oh I will, Uncle Mike!" grinned Candy. "Do you like?" asked the sissy as he slowly turned for his uncle.

"You've got fucking great legs kid! I've always loved dark stockings!"

Candy sat straddling his uncle's thighs, their faces just inches apart, his rigid cocklette also just inches from his uncle's own thick dick. "Your eyes look great," complimented his uncle. "You must have been practising for quite some time now!" Candy leaned closer and ran his tongue along his uncle's lips. Mike tried to kiss his sissy nephew but Candy drew back, smiling, teasing.

"Chanel!" said Mike, "You smell like your mother! I like it!"

Candy blushed. "I like Gucci better, but I couldn't have that in the house. If my mother smelled another perfume, she might get suspicious!"

"Kid, she is long past suspicious! After today," Mike said, "you can wear whatever perfume you like! Leave that to me!"

Mike grasped Candy's ass in both hands lifting the sissy and placing him back down so that his cock was now behind him, nestled along the crack of his nephew's ass. Mike took one of Candy's nipples between his lips and sucked and nibbled. "Oh, Uncle Mike, yes!" cried Candy as electricity snapped through his body.

At the same time, Mike probed at Candy's asshole with a finger. He found it slick and his finger easily penetrated to the first knuckle. "You've used some lube!"

Candy blushed, his face still taut with the excitement of having his nipples played with for the first time. "Uh huh." he managed to utter.

"You're expecting to need that?"

"Oh yes! I hope so!"

"You ever have anything up there before?" asked Mike?

"Just... just a carrot. I had to know what it feels like!"

Mike thrust his finger in the the next knuckle and began to push in and out of Candy's sphincter. His lips found Candy's, and the two kissed passionately for a few minutes. Candy found it hard to continue the kiss. His excitement was mounting. His dicklette was aching so very very much! He was panting furiously as his uncle tried to add a second finger to feed his hungry ass. Oh god, it was going to happen! He knew it! It was finally going to happen!

And it was!

Mike stood, picking the sissy up in his arms and carried Candy upstairs to Candy's bedroom. Well, actually to Kenny's bedroom. It was still very much a young man's bedroom. Kenny had not had the nerve to decorate the room to Candy's tastes, so it was still a masculine room.

But not for much longer. Mike lay Candy down on the bed and as Candy watched, Mike removed his sandals and pulled off the shirt he had put on when they came inside. He stripped off the shorts and underwear he had worn while they ate pizza. Mike was now naked. Hairy, thick, smelly. All man.

Mike removed Candy's kimono. The sissy was now dressed only in his dark stockings and heels. Mike pulled Candy to a sitting position and without uttering a word pushed his cock between Candy's lips. Candy eagerly sucked on his uncle's thick gorgeous cock. His hands played with his uncle's heavy balls. He was frenzied and he bobbed his head eagerly on that lovely dick!

"Get it nice and wet, honey" Mike said gruffly. "You're going to want to get it nice and slick!" Candy pulled his head back and continued to fist the dick while he looked up into his uncle's eyes!

"I want this!" he said.

"What do you want, sissy!"

"I want you to fuck me! I want you to fuck my sissy ass! I've wanted this for so long!"

"Well you're going to get it, sissy! Up on the bed! Get on all fours!"

Candy eagerly turned around and got onto the bed. But Mike grasped him and turned him so that his knees were on the edge of the bed, his feet projecting out. Mike stood behind his nephew. He pulled Candy's ass cheeks apart and stared at the young man's virginal pucker. "Where's your lube, boy?" Mike asked gruffly. "You're going to need some help!"

"In the drawer of the bed table!"

Mike leaned over, opened the drawer and pulled out he lube. Flipping the cap, he drizzled a long stream of lube onto Candy's ass hole. Candy shuddered from the sudden chill, then moaned as Mike used a couple fingers to push the lube into his ass.

"Oh, Uncle Mike! Yes! That feels so good! Put it in me, please! Put your cock in my ass! Fuck me!!"

Mike placed the head of his dick at Candy's hole. He dragged it up and down the ass crack, lubing the head. Then he grasped Candy's hip with one hand, and held his dick in place with the other, and pushed. The head slipped in! Candy gasped. Oh heavens, he was finally being fucked! He had wanted this for so long. He had needed this for so long. He was a boy, a man. It wasn't right for a man to want to be fucked. But long ago he had realized he was a sissy. And sissy's were meant to serve cock. To suck cock. And more importantly to be fucked by cock.

And now, finally, he was being fucked by a cock!

"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. 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's 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 more 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!"

Candy grasped the bedding in his hands and squeezed. Mike pulled his cock back briefly, then pushed again, sliding another inch into his nephew's rectum. Candy's eyes watered but his sobs stopped as he started to gain control again. The shock of the pain was over. He grunted as another inch pushed into his bottom. Realizing that the screaming was done, Mike removed his hand from Candy's mouth and used both hands to grip the sissy's hips and pulled him closer, another two inches slid into the femboy!

"Oh, you are so tight, baby! You have a gorgeous ass! So round, so plump for a boy! Made for fucking!" Mike grunted as he began to saw his cock in and out of Candy's bottom. It was so hot, so tight. He pushed harder again and slid even further into that dark channel!

Candy could not believe how full he felt! It hurt so much... but that pain was easing. Mike's cock pushed deeper and lightning struck as his cock grazed across Candy's prostate! Candy did not know what that was, or what was causing it, but a bolt of delight zapped through his body. He tossed his head back and shuddered in pure delight! "Oh yes, Uncle Mike! Right there. Do that again!"

Mike responded by fucking Candy faster. In another few moments he bottomed out, his cock thrust as deeply into the he-slut as he could. His heavy ball sac bounced against Candy's tight little nut purse. "That's it honey! You've taken my entire dick! How's it feel, sweetie?"

"It's.. it's... it's so wonderful, Uncle Mike! I feel so full! Oh god, I love having your cock in my ass! Fuck me, Uncle Mike! Fuck my ass, please!"

"Anything to oblige my cute sissy nephew," Mike grinned. He slid his cock back until the head was almost out, and then slid the full length back inside. Mike grunted. Candy grunted. Candy smiled. He was in sissy heaven!

Candy's ass was now one large pleasure zone! Mike set up a steady rhythm of sliding his cock in and out of the sissy's ass. Waves of pleasure surged through Candy's body! "Fuck me, Uncle Mike! Oh that's fucking wonderful! Harder! Ram my ass harder!!!"

Mike withdrew his cock. Lube slime spilled from Candy's ass onto the floor. Small brown flecks coated his cock. He grasped Candy and flipped him over so the gorgeous sissy was on his back. Candy looked up at him adoringly. Candy's pricklette was rampant and drooling precum. Mike pushed Candy up on the bed, raised the sissy's ass and then speared his cock deep into his nephew's asshole with one thrust! "Yessssssss!" moaned Candy.

Mike was on his knees, the angle of his penetration awkward. While kneeling on the bed, he picked up Candy's body and pulled him close. Candy was now vertical, and his ass slid down solidly on his uncle's cock. Candy felt the heavy sweat captured in his uncle's thick chest hair. He inhaled his uncle's heavy masculine scent. This was where he belonged - in the arms of a man, with a dick up his ass!

Candy's mouth sought his uncle's. Mike's tongue invaded his mouth and they kissed hungrily as Mike raised and lowered Candy on his dick. Two firm thrusts ran across Candy's prostate. He threw his head back and screamed as his sissy cockette erupted, spurting his boy seed across his chest. He bit into his uncle's shoulder as his cum squirted deliciously!

"My turn!" growled Mike. He lifted Candy off of his cock. He grabbed a couple pillows and put them under Candy's ass raising it up. He held his cock and teased the sissy momentarily. "Put it back in me! Please!! I need your cock inside me!!" whimpered the sissy, his legs raised and spread wide. His brown pucker seemed to wink at Mike!

"Oh you are going to get fucked good now!" said Mike as he lanced his cock back into his nephew. Mike then set up a furious pace. His dick pistoned in and out of his nephew's ass. Each time he pulled back, Candy's ass distended, trying to hold on to the invader as long as possible. Candy thrashed his head about in ecstasy!

"Here is comes, baby, here it comes!" cried Mike. He fell across the sissy as he buried his cock deep and his cock spurted and pumped jet after jet after jet of hot cum deep into that glorious tight ass. Candy's head was trapped in Mike's armpit as the heavy man convulsed uncontrollably. Candy breathed in the heavy musk of his uncle.

Mike rolled over, exhausted. His cock slipped from Candy's ass, and a torrent of cum sluiced from the sissy's ass onto the sheets. He pulled Candy closer and they kissed a long passionate kiss. Candy lay with his head on his uncle's thick muscled arm and ran one hand through the damp mat of hair on his uncle's chest.

"That was fucking fantastic baby!" panted his uncle, his heart still racing. "Your ass is so tight and so sweet!"

Candy could have stayed there all evening, adoring his uncle. But he had to pee! As he got up off of the bed, he felt his ass expel a glob of cum and as he walked to the bathroom a rivulet of cum ran down his leg. He shivered.

In the bathroom, his dickie was still rigid from the viagra. He had to sit and try to bend his penis down in order to pee. This opened his ass a bit more and he suddenly farted and he heard more cum dribble from his asshole. When he finished peeing he wiped the tip of his penis and his ass. As he flushed he was pleased to see there was no blood going down the drain.