Tale of Two Sissies

Max removed his tongue from the boy's mouth and licked his face; his forehead, his eyes and nose, his chin.

"Mine." Max breathed into Jim's ear as his hands gripped the boy's ass-cheeks and kneaded and squeezed. "Sissy's little clitty likes Daddy's attention, doesn't it, bitch?"

"Yes, Daddy!" Jim panted.

Jim gasped as Max's finger found his rosebud and rubbed and teased it. Max played with it briefly, then rolled over to retrieve the lube from the nightstand. Max applied a large blob to his finger and then returned the digit to Jim's asshole, massaging his rosebud and then slowly invading the boy's rectum.

"Ooooh!" Jim gasped as Max slowly finger-fucked his boy-pussy.

"Does that feel good, little sissy-gurl?"

"Ye - yes, Daddy!"

Max slowly removed his finger and then applied lube to three of his fingers. He squeezed the boy's ass-cheek briefly and then inserted his fuck-finger into the boy's hole. It went in easily this time and Jim responded by softly moaning as Max massaged and loosened his passage. Then Max inserted his index finger and fuck-finger into the boy. Jim tensed a bit on entry, but soon accommodated both invaders. Max began kissing and licking the boy's ears and neck as he slowly finger-fucked him. Then Max licked down to the boy's chest and licked and teased and gently bit the boy's nipples into erectness. Jim raised his hips to meet the third finger that entered him.

"Oh, yes, Daddy! Please, Daddy! More, Daddy!" Jim moaned as new sensations of pleasure and lust coursed through his trembling body.

"You're ready, boy. Daddy is going to breed you. Daddy is going to make you his little sissy-bitch." Max breathed into the boy's ear as he removed his fingers from Jim's boy-pussy.

Jim did not resist as Max threw his skinny legs over Max's massive shoulders. Max positioned his throbbing love stick against the boy's pulsing rosebud.

"Your cherry is mine!" Max grunted as he eased his cock into Jim's boy-pussy.

"Noooo! No, Daddy! It's too big!" Jim begged as his body trembled from the invader and he held on for dear life to Max's shoulders.

"Shhh! Shhh! Just take it, bitch." Max urged as he slid deeper into Jim.

Jim held on tightly as tears of pain coursed down his cheeks. Max grunted as his monster bottomed out in Jim's boy-pussy. Jim could feel Max's cock throbbing inside of him and Max's large balls resting against his ass-cheeks. Jim gasped as Max began to withdraw his throbbing organ until only the moist head of the uncut cocked remained inside him.

"Oh, noooo!" Jim moaned as Max slowly slid back into his boy-pussy until it was totally buried in Jim's ass.

"That's it, baby. Take it, baby." Max urged as he began to slowly fuck his new sissy.

Jim was totally overwhelmed. The musky smell of Max's sweating body, the pain of being fucked by Max's pulsating monster. It was too much for his senses. Jim didn't think that he would be able to bear the pain of being fucked much longer. But then he realized that the pain had actually begun to lessen as Max rhythmically slid in and out of him. As Max picked up the pace of his fucking, the pain in Jim's boy-pussy was actually being replaced by a pleasurable feeling the boy had never experienced.

Now Max was fucking him in earnest. The boy's ass-pussy was so tight and slick from the lube and Max's pre-cum that Max was losing control. He could feel the boy's little prick throbbing against his stomach. The boy was now moaning and growling incoherently as Max fucked him hard and fast. Max could feel his spunk building in his balls, ready to shoot into his new sissy-victim. And then Max could no longer contain himself. With a loud grunt the first deposit of sperm erupted into the boy's bowels.

"Ahhhhh! Oiigggrrrrzzz!" Jim railed incoherently as he felt his boi-pussy being filled with load after load of Max's spunk. They looked like two, wild animals in heat; fucking for dear life. Jim's own body shook uncontrollably as his legs tightly grabbed Max's torso and Jim's little prick erupted, depositing his own little load onto his tummy.

Spent, Max collapsed onto the boy. They lay there clinging to one another, both shaking from the violence of the orgasms that shook them to the core. Jim's arms and legs plopped onto the bed as he lay there, senseless, with Max's huge cock still throbbing inside of him. Max lay, panting, on top of him, exhilarated from the ease of his conquest and the breeding of a new sissy. As his cock began to go flaccid, Max slowly withdrew from his new boi-pussy and rolled onto his back on the bed.

"Come here, sissy-gurl. Come to your Daddy." Max cooed as he pulled Jim into his arms. They lay there, sated, and soon both drifted off to sleep.

Jim slept in Max's arms for about an hour. He was awakened by Max nibbling on his ear and licking his neck. The licking soon turned to gentle bites and then Max's mouth on his own. He could feel his little prick stirring as Max's cock was already hard and leaking pre-cum against his leg. Max maneuvered Jim onto his tummy and sat across the boy's legs while he grabbed the container of lube and slathered it all over his throbbing cock. He slipped it into the boy's pussy in one slow motion. It went in easy this time and he began slowly fucking the boy as Jim moaned senselessly beneath him.

Max fucked him for hours. Jim soon learned that Max could recover quickly after blowing his load in Jim's ass. He would generally be hard again in ten to fifteen minutes. Max fucked him missionary style. He mounted him while Jim lay on his stomach. He took him on all fours, doggy style.

By the time three in the afternoon rolled around, Jim had been fucked in every conceivable position imaginable. Max had reduced him to a mindless little fuck-slut who craved all that Max could give him. But Max was hungry for food and he wanted the boy to keep up his strength for the night ahead. So they broke for lunch.

"C'mon, baby gurl. Let's get something to eat. You need to keep up your strength." Max said as he got out of bed and slapped Jim on the ass.

"Yes, Daddy." Jim said as he drunkenly stumbled out of bed and followed Max downstairs into the kitchen.

Jim sat on a stool at the kitchen island as Max made sandwiches for them. Max pushed a sandwich across the island to Jim and poured him a glass of sissy-milk to go with it. Max popped a can of beer open and drank it with his own sandwich. Jim didn't realize how hungry he was. He wolfed down the sandwich and his sissy-milk then asked Max for a second glass. Max smiled as he poured the second glass and then finished his own sandwich and beer.

"Tell me, baby-gurl. Do you live alone or with your parents?"

"I - I live with my aunt. My parents died."

"I'm sorry to hear that, sweetie. Is your aunt nice?"

"She's a bitch, Daddy!" Jim said angrily. "She got my parent's house and custody of me when they died. She's a useless drunk who's on welfare. She treats me like shit!"

"So move out, honey. You're nineteen. You're an adult."

"I don't have the money to live on my own."

"You don't need money, baby. You're Daddy's gurl now."

"You mean move in with you?" Jim asked incredulously.

"That's exactly what I mean, sweetie."

"I'm just so confused." Jim said despairingly. "I don't know who I am or what I am anymore!"

"It's quite simple, baby. You're a sissy. You're my little sissy-gurl."

"But I'm not a girl!" Jim protested. "I'm a boy!"

"No, baby. You stopped being a boy when Daddy took your cherry and my sperm filled your tight, little ass. Cock goes in, mind goes shut. You're my sissy now."

"And you want me to live here?"

"Yes, baby. Daddy will take care of you from now on."

"I'll - I'll need to go get my clothes."

"No, baby. Daddy will buy you new clothes; sissy clothes."

"But - but I have to tell my aunt."

"Does she have a phone?"

"Yes."

"Text her!"

"Just text her?"

"Text her now. Tell her you're leaving and not coming back."

"Yes, Daddy." Jim retrieved his phone and tapped out a text for his aunt. "It's done, Daddy."

"Good gurl!" Max affirmed. "We'll go shopping tomorrow to buy you some sissy clothes. But you also need a sissy name. Jim just won't do anymore. Let's see. . . Jenni! From now on, you are Jenni - J-e-n-n-i! My little sissy bitch!"

"Yes, Daddy." Jenni surrendered.

"Now, give me your phone, sweetie." Max said holding out his hand.

"Why, Daddy?"

"Sissies don't need phones, honey. Not unless their Daddy gives them one. Now give me your phone."

Jenni handed her phone to Max. Everything was just moving so fast. What was going to become of him/her?"

"Good gurl! Come with me." Max walked to the couch in the den with Jenni following close behind. When they got to the couch, Max sat down with his arms across the back of the couch and spread his legs.

"Kneel in front of your Daddy, slut."

In a daze, Jenni knelt in front of Max.

"Worship Daddy's cock, bitch."

Jenni rubbed his hand over Max's flaccid member causing it to awaken and begin to grow. He licked it from base to head and then began to suck.

"Good gurl. Good sissy. Good slut." Max affirmed as he put his hand on Jenni's head as his new sissy sucked contentedly.

Jenni wore no clothes for the next seven days. Jenni did not leave the house for the next seven days. Jenni spent all of his waking hours sucking Max's cock or being fucked by his new Daddy. In every possible position. Jenni learned to impale himself on Daddy's monster and ride it till his boy-pussy was filled with Daddy's cum. For seven straight days Jenni lived for only one thing - COCK!

At the end of seven days, Max took his new sissy shopping. They went to the girl's department of a local department store where one of Max's lady friends took charge of Jenni's wardrobe. They walked out of the store with bags of new clothes for the sissy; panties, camisoles, lingerie, girl's short-shorts, girl's tops, short skirts, girl's shoes. A whole new ensemble to reflect Jenni's new reality - sissy.

The next stop was the tattoo parlor owned by one of Max's friends. Max like his sissies to be marked. And so Jenni was marked; "Sissy" tattooed on his tummy right above his little prick, "Slut" on his left ass-cheek, "Bitch-in-Heat" on his right ass-cheek.

Then Max took him to an "Adult" store that carried all sorts of BDSM paraphernalia. Max bought a cage for Jenni's cock, a vibrating plug for Jenni's ass, a collar and chain for Jenni's neck, cuffs for Jenni's wrists and ankles, and a pink choker embossed with "Max's Sissy." Max made it clear that the collar and cuffs were always to be worn at home and that Max would lock the cock cage onto Jenni whenever he was to be left alone. The butt plug was to be worn whenever Max decided and it was controlled by an app on Max's phone.

Then it was back to Max's house and another seven days of fucking and sucking. As Max frequently stated, it was "Cock goes in, brain goes dead." By the end of those fourteen days, Jenni was conditioned to think primarily of cock. By the tenth day, Jenni would actually begin to salivate whenever Max pulled out his monster meat. By the end of the two weeks, Max was very satisfied with what he had accomplished. It was time to take his new creation out into the world.

Meeting Kaci

The world turned out to be a gay leather bar that Max liked to frequent. He dressed Jenni in pink panties and white ankle socks with pink fringe; tight, white short-shorts; a white cut-off tank top that exposed Jenni's tummy; platform sandals; and, of course, Jenni's choker that proclaimed him "Max's Sissy." The ensemble was completed by Jenni's collar and chain.

Max was dressed in an all leather ensemble: tight, black leather pants, black leather boots, and a black leather jacket left partially open to expose his curly chest hair. Max led Jenni into the bar by the chain attached to his collar. The bar was filled with men dressed like Max. There were an almost equal number of men who were obviously gay and submissive to the "real" men in the bar. Some of the subs were dressed as women, with greater or lesser degrees of success. Some went for the look of feminized boys. None of them were as pretty as Max's sissy.

Jenni could feel all eyes on him as Max led him into the club and up to the bar. Jenni felt anxious and afraid and slightly aroused as the men looked at her; some with mild interest; many with outright lust in their eyes. Max sat himself on a barstool and drew Jenni to stand between his legs. He squeezed Jenni's ass-cheek, then rubbed his hand across his sissy's little prick. His mouth found Jenni's cheek and hungrily nibbled at his neck while he played with his bitch's prick. Then Max plunged his tongue into the boy's sweet mouth, then gave Jenni's prick a final squeeze and turned to order drinks. All in the bar understood that Jenni was Max's property.

Max possessively kept his arm around Jenni while they drank.

"Look at the real men, sissy." Max said to Jenni. "They all look at you with lust in their eyes. They want you. They want to fuck your sexy, little sissy-ass."

The next hour or so was a blur for Jenni. The drinks came - a shot and a beer for Max, a strawberry daquiri for Jenni. Various men came to greet and talk with Max and to check out his new sissy. All who came to talk asked Max for permission to pet his new sissy-boy. All were given permission. It turned out that petting the sissy meant fondling Jenni's crotch. Jenni came twice and by the time the ritual was over, his pants sported a large, wet cum-spot on Jenni's crotch. Then Max settled down to talk with a guy sitting on the stool next to him. Max kept his arms possessively around Jenni and occasionally, idly squeezed Jenni's ass or pinched his nipples.

Jenni had basically tuned out his surroundings after realizing that Max's mind was elsewhere. The quiet hum of conversation permeated the atmosphere. Here and there Jenni could see a Dom, like Max, kissing or fondling the boy that was with him. And then the bar began to buzz again as a new couple entered the room. It was a large, heavy-set, rather out of shape, man with one of the prettiest girls Jenni had ever seen in tow.

"Wally!" Max shouted with glee at the man. "Get your ass over here, man!"

Wally smiled from ear to ear and led his girlfriend by the hand to where Max and Jenni sat. As they drew closer, Jenni had to revise his opinion of Wally's companion's appearance. The closer they got, Jenni realized that the girl was actually a boy; a very pretty, feminine looking boy; a sissy like Jenni. The boy was slightly taller than Jenni, but just as slender. He was dressed in tight, khaki short-shorts that looked as if they were painted on his squeezable little ass and a midriff-length pink t-shirt. The boy also wore a pink, lace choker emblazoned with "Sissy-Slut." As they approached Max and Jenni, the boy began to smile from ear to ear.

"Uncle Max!" the boy shouted happily and threw his arms around Max's neck in a big hug. The boy's hip butted into Jenni's crotch as Max hugged him.

"Give your uncle Max a big, sloppy, wet kiss you sexy little piece of ass!" Max ordered happily.

The boy eagerly opened his mouth to accept Max's tongue. After a long kiss, the boy separated from Max and looked Jenni up and down.

"Is this your new sissy, uncle Max?"

"Yes, baby. This is sissy, Jenni."

"Ooooo! He's pretty, uncle Max! Can I play with him? Please? Pretty please?!"

"Ha, ha! Settle down, little slut. You haven't even introduced yourself yet.

Wally's sissy smiled lasciviously at Jenni. "My name is Kaci. I'm a sissy and I think you're so cute, I just want to eat you up!"

"Slow down, Kaci." Max instructed. "First I want to tell Jenni your story."

"Can't it wait till later." Kaci pouted.

"No, baby-gurl." Max said and turned to Jenni.

"Kaci is Wally's nephew. When his parents died in an auto accident, Kaci went to live with Wally, her only relative. Kaci was a normal teenage boy of eighteen but hard to control. Always getting into trouble at school; usually for pestering the girls. Kaci's parents left a significant estate that came into Wally's control when he took responsibility for Kaci. Wally doesn't want to lose control of any of that wealth, so he came to me for help. Even though he is not into boys or men, Wally asked me to transform Kaci into a sissy-gurl who would be easy for him to control. It took four intensive weeks of conditioning, including sissy hypnosis. I had to leave the little bitch tied to a bed for two weeks straight with a vibrating plug in her boi-pussy and another vibrator strapped to her clitty. At the end of two weeks, Kaci was a mindless mass of sensual sensations. His body twitched uncontrollably, drool came constantly out of her mouth and his mind was completely blank and ready to be re-written. At that point it was easy for me to program Kaci's mind to make him a good little sissy-gurl. Are you a good little slut, Kaci?"

"Oh, yes, uncle Max! I'm a good, horny little slut!" Kaci exclaimed happily. "Can I play with your new sissy now? Please! Pretty, pretty please, uncle Max!"

"Jenni, put your arms around Kaci's waist." Max instructed and Jenni stood and complied. "Kaci, put your arms around Jenni's waist." Kaci eagerly complied.

"Good gurls!" Max said. "Put your hands on each other's ass-cheeks."

Both gurls complied and Kaci immediately began massaging and squeezing Jenni's ass-cheeks Jenni's little prick began to grow in his tight pants and he could feel Kaci's much larger prick beginning to grow and throb against his own. Jenni began to breathe heavily as he stared into Kaci's eyes as their boi-clitty's rubbed against each other and Kaci continued to fondle his ass. Jenni was mesmerized by Kaci's constant, intent stare and the smell of Kaci's intoxicating perfume.

"Please, can I kiss Jenni!" Kaci begged.

"Yes, baby. But remember that we are in a public place. So all you can do is kiss and squeeze your asses and rub your clitties together."

Kaci needed no further encouragement. He quickly covered Jenni's mouth with his own and plunged his tongue into Jenni's yielding mouth. Jenni was losing control to Kaci as the boy kneaded Jenni's ass-cheeks and rubbed his prick against hers. Soon they were groaning into each other's mouths, drool running down the sides. Jenni held on to Kaci for dear life as Kaci ground his cock against her little prick. A growing spot of precum spread across both of their crotches as their hardened rods rubbed against each other. Jenni tried to break the kiss, but Kaci immediately grabbed the back of Jenni's head with one hand to hold him in place while he continued holding Jenni's ass with the other hand. Jenni knew there was no escaping Kaci's embrace; so he simply shut down his mind and surrendered to the sensations coursing through his body. The two sissies kissed and drooled and rubbed against each other for almost ten minutes; passion mounting and stopping impossible. The men in the bar drew close to get a better view of the show, egging the sissies on and encouraging them. Then came the inevitable eruption. It was violent and intense for both of the quivering boys. Animal noises emanated from their throats as they bucked and humped each other. Their spunk shot out of their pricks spreading across their crotches, uncontained cum dripping out of the legs of their short-shorts. They broke the kiss and clung to each other, shaking and panting and cumming in their pants. As their sissygasms began to subside, the men and boys in the bar applauded appreciatively and hooted and hollered for more.

Kaci was the first to gain control of himself. He turned Jenni around so his still hardened cock was resting between her ass cheeks. He wrapped his arms around Jenni, one hand resting possessively on her still hardened little prick. Jenni simply slumped against him in surrender.