Tale of Two Sissies

This is a story of reluctance, seduction, surrender, sissification and enslavement. If any of these offend you, skip this story. All characters are over the age of 18.

Making of a Sissy - In the Park

Max was on the prowl. Max was on the prowl for a new boy. It had been two weeks since he had sold his latest sissy, Chubby Charlene, to his friend Lew. Lew liked chubby sissies and had been salivating at the prospect of owning Charlene for weeks. Max, on the other hand, was not especially fond of chubby boys. He liked them short and slender and pretty of face. Max loved to take an unsuspecting boy and seduce him into the world of gay sex. He was very adept at turning a boy from a straight male to a slut lusting after cock. First turn them gay, then make them sissies. That was Max's modus operandi.

Max usually had good luck finding boys in the park near his bungalow. But he had already made three circuits of the park this morning with no results. There just weren't many people in the park on this weekday morning. There were some mothers with their children, but the cute little boys were much too young for Max. He wasn't a pedophile after all, he liked them in their late teens; still young and impressionable, but also susceptible to being seduced by a strong man. And Max was definitely a strong man; six-three, two hundred seventy-five pounds of mostly muscle, and an appropriately masculine hairy body, mesmerizing eyes and a domineering personality that easily overwhelmed the weak boys he was able to snare.

He was making his last circuit of the park before giving up for the morning when he spied him. He was sitting on a lonely bench under a tree reading what appeared to be a textbook. The boy was slender and, even though he was sitting, Max could tell that he was short. He was wearing a t-shirt and a pair of baggy khaki shorts with gym shoes and athletic socks that came up just below the knee. His sandy hair was long, coming just below collar-length and hanging down over his face as he bent over the textbook. He had the nervous habit of pushing his hair back behind one ear as he attempted to read.

This boy was worth exploring. Max sauntered over to the bench and hovered above the boy.

"May I join you?" Max asked as the boy looked up at him.

"Uh, sure. It's a public park, mister."

"Call me Max. That's my name. What's your name?"

"Jim."

"Nice to meet you, Jim." Max extended his hand in greeting as he sat down on the bench.

"Nice to meet you, Sir." Jim replied as he took Max's outstretched hand.

Jim's little hand was quickly swallowed up by Max's large paw. Max gripped Jim's hand tightly and caressed the back of the boy's hand with his thumb before releasing him. The boy had smooth hands, like the hands of a little girl.

"You playing hooky from school, son?"

"No, sir. I already graduated high school."

"I see," Max smiled. "So you studying a college course?"

"Kind of, sir. I didn't make it into a college. I didn't make it into junior college either; missed the sign-up date, so I got to wait until the next semester. Figured I'd buy the books and get a start on learning the stuff I need."

"That's very commendable, Jim. Do you have a job?"

"No, sir. I don't got a job yet. I applied at a couple places, but no one's hired me yet."

"How old are you, son?"

"I'm nineteen, sir."

"A wonderful age! Do you have a girlfriend?"

"No, sir. I took a girl to prom, but she's away at college now. It didn't really go that well anyway."

"Oh no? What happened?"

"I'm kinda shy and I think she was lookin' for some fun."

"I understand. Do you have a boyfriend?"

"You mean, like, guys I hang out with?"

"I mean, like a special friend that you can get naked and play with."

"Oh no, sir. I'm not like that. I don't like boys that way."

"So you've tried things with boys, but didn't like it?" Max smiled slyly.

"No. No, I never tried nothing with a boy."

"Then how do you know you wouldn't like it?

"I don't know. I. . . .I; you ever done things with guys, Sir?

"With girls and with boys."

"But. . . but, ain't it wrong with guys?"

"I make boys feel good; real good." Max smiled. "It's not wrong to feel good, is it Jim?" Max asked as he slid closer to the boy on the bench.

"I. . . . I don't know. I guess not." Jim stammered.

"I like to make boys like you feel good; real good." Max smiled as he placed his hand on Jim's thigh and gently squeezed. "Would you like me to make you feel good, baby-boy?'

"Like I said, I'm not really into guys, sir." Jim said, nervously scooting away from Max.

"That's not a problem, son. You said you're getting ready for college?"

"Yes, sir."

"You know what the college boys are doing in the dorms now?"

"No, sir."

"They're experimenting, son. With girls; with other guys; they're learning what they like."

"You mean boys are kissing and playing with other boys?"

"They sure are."

"I-I don't know if I'd like that." Jim said uncertainly.

"Well, you'll never know unless you try it, right? Why don't we experiment a bit; just like college?" Max said as he slowly slid closer to Jim.

"What, what kind of experiment, sir?"

"We'll try some things out and if you don't like it, we'll stop."

"We, we can stop?"

"Of course, honey. But I have a great reputation for making boys like you feel good. So good I'll bet you won't want to stop."

"I. . . . I don't know. I guess so. I. . . . how would you make me feel good?"

"Can I touch you, baby?" Max asked. "If you don't like my touch, I'll stop."

"Where, where do you want to touch me?"

"How about above the waist?" Max chuckled.

"O - Okay. I guess that would be alright." Jim responded.

Max smiled and reached his hand out to caress the side of Jim's face.

"Such a pretty boy you are." Max said as he caressed Jim's face and then moved his hand down to the boy's ear. Rubbing the lobes and gently putting his little finger in the boy's ear canal.

"Do you know about your erotic spots, baby?" Jim smiled.

"N-no, sir." Jim sighed in reaction to the teasing of his ear.

"The ear is certainly one. Does this feel nice, baby?"

"Oh, yes, sir." Jim sighed.

"Should I go on?"

"Yes, please."

"Good boy." Max smiled. "Another erotic spot is a boy's chest. Most people think only a girl gets aroused from playing with her chest and nipples. But boy nipples are just as sensitive." Max said as he slowly moved his hand down to Jim's chest and began to rub through the t-shirt. Jim caught his breath as Max pinched and teased first one nipple, then both through the cloth of the shirt.

"Omigod!" Jim gasped as felt his little prick began to stir in his pants. It was as if there was an electrical connection between his nipples and his cock.

"Do you like that, baby boy?"

"Oooh, yes!"

"Should we stop, or do you want more?"

"Mo-more, please."

"Good boy!" Max said as he moved one hand down the boy's tummy to the boy's thigh while the other hand continued to minister to Jim's nipples.

The boy was breathing heavily now that Max was caressing his thigh and his nipple. Max snaked his hand up the boy's thigh, inside his shorts leg and found Jim's hardening little prick with his fingers. The boy squirmed at Max's touch and raised his hips slightly to grant Max fuller access to his moist little penis.

"Do you like that, baby boy?" Max teased as he deftly manipulated the boy's throbbing organ, spreading his cum-stain over his briefs.

"Oooh, yessss!" Jim hissed as Max brought him close to climax.

"Do you want more, baby?" Max encouraged.

"Oh, please don't stop. It feels so gooood!" Jim breathed.

"Let yourself go, sweetie. Let Max make you explode." Max encouraged as his tongue went to work on Jim's ear; licking, kissing, biting, caressing.

"Oooooh, pleeeeeease!" Jim exclaimed as he felt his body respond totally to Max's ministrations.

"Cum, baby, cum! Cum for Max, baby! Cummmm!" Max cajoled as he felt the boy's little prick begin to spasm. Max tightened his grip on the quivering rod as it spewed it's juice, coating Max's hand and the boy's wet briefs.

"Omigod, omigod!" Jim gasped as his orgasm shook him. Jim threw his arms around Max's neck and held on for dear life as rope after rope of cum spewed from his spasming prick. The boy shook in Max's embrace until his orgasm was spent and his body started to quiet down.

"Shhh! Shhhh! Good boy. Good boy." Max whispered as the boy shook in his arms

"Good boy. Pretty boy. Pretty baby. Good gurl." Max whispered soothingly as Jim began to calm down.

"Did you like the way Max played with you, pretty baby?" Max softly asked.

"Yes, sir. I never felt anything that good in my life, sir."

"Do you want more, pretty boy?" Max asked enticingly.

"Yes, sir. Please, sir." Jim implored, looking up at Max with puppy-eyes.

"Good boy, good gurl." Max smiled. "Do you see the houses across from the park there?"

"Yes, sir."

"That's where I live, sweetie. We'll go there now and Max will teach you things that will make you feel even better."

"I. . . . I don't know, sir. I should get home so they don't worry about me."

"You're nineteen, right?"

"Yes, sir."

"Then you're an adult. You can make your own choices. If you want to come with Max, no one can stop you, can they, honey?"

"I guess not, sir."

"Do you want to experiment more with Max, honey?'

"Ye-yes, sir." Jim acquiesced.

"Then take my hand and come with me, sweetie." Max commanded as he stood up from the bench and extended his hand.

Jim took the outstretched hand and stood up shakily. At five-five, he was dwarfed by Max's height.

"What will we do there, sir?" Jim asked rather timidly.

"We'll play, boy. Max will guide you into a new world of pleasure. Now let's go, honey."

They walked hand-in-hand across the park towards Max's abode. To anyone casually observing, they looked like a daddy leading his little boy by the hand. To anyone who observed close up, they couldn't help but see the cum-stain spreading across Jim's crotch and the look of lascivious triumph on Max's face as he led the boy to his fate. Jim was still somewhat unsteady from being drained by Max on the bench and before they were halfway across the park, he stumbled drunkenly and Max wrapped his arm around Jim's waist to steady him and guide him. Max marched him up the steps outside his bungalow and unlocked the door, holding it open for his new prey.

"In you go, gurl." Max said as he placed his hand on Jim's ass-cheek and gently pushed him into the dark hall of the bungalow.

As the door closed behind them, Jim stood in the darkened hall as if it were a strange, new world that he had stumbled into. A combination of anticipation and fear took hold of him as he felt Max's guiding hand squeezing his ass and pushing him forward.

Making of a Sissy - In Max's House

Max steered the young boy into the kitchen. The shutters were only partially opened letting in a miniscule amount of sunlight. Jim looked around anxiously as he began to wonder about his decision to follow this man blindly into his home.

"It's kind of dark in here, sir. Isn't it?"

"It helps keep the house cool in the hot summer months; air conditioning doesn't have to work as hard."

"Oh, that makes sense."

"Have a seat, honey."

Jim hoisted himself up onto one of the barstools next to the island in the center of the kitchen. Max walked over and stood in front of him, smiling a rather predatory smile.

"It's cool and comfortable in here." Max said. "But you can't be very comfortable with these wet pants of yours." Max cupped the boy's crotch with one hand and gently squeezed and rubbed.

"I - I should probably be going, sir." Jim said as he squirmed under Max's touch.

"You can't go anywhere with such wet pants." Max responded. "Let's get them off of you and into the dryer." And Max unsnapped the top button of Jim's shorts and slowly pulled down the zipper. "Lift up a little." Max instructed. Jim lifted his hips off the seat and Max deftly stripped him of his shorts.

"Oh, but look at your undies. They're all moist and stained." Max exclaimed as he ran his finger over Jim's little prick and then squeezed it gently.

"We'll have to dry these too." Max said and smoothly stripped the briefs off of Jim.

"Just wait here, baby, while I throw these in the dryer."

Jim sat and waited while Max walked the few steps to the laundry room and threw Jim's things into the dryer and turned it on.

"You know, baby boy, you look rather silly sitting there in socks and shoes and no pants. Let's get you more comfortable." Max stripped Jim of his shoes and socks without waiting for his assent.

"That's better, honey." Max said approvingly. "You thirsty?"

"Yes, sir." Jim answered as he squirmed self-consciously on the barstool.

Max walked over to the refrigerator and produced two bottles of beer, offering one to the boy. Jim took a long drink of the cold liquid. He didn't realize how thirsty he was.

"I - I don't think I should be here, sir." Jim said timidly.

"Why not, baby boy?"

"You did things to me in the park that boys shouldn't do to each other."

"I did things to you that many boys do all the time. Did it make you feel good, sweetie?"

"Well, yes, but, but isn't it wrong?"

"No, baby, it's natural; just a real man enjoying a boy's body and making the boy feel good. You want more, don't you, honey."

"I - I don't know. I'm confused."

"Did I hurt you, sweet boy?"

"No."

"Then let's just spend some time together. Let's get to know each other better and you'll see that I only want what's right for you. Max isn't here to hurt you. Max is here to guide you and show you pleasure that you never realized existed. What do you say? Will you stay for awhile and play?"

"Okay. I guess it can't hurt."

"Good! Now, are you hungry?"

"A little."

"How about some fruit?"

"That would be good."

"Great."

Max went back to the refrigerator and grabbed another beer for each of them. He didn't even ask Jim if he wanted another; he just plopped it down in front of him and watched approvingly as the boy took a pull from the new bottle. He began to cut up some fruit into a bowl as he watched the boy look around the kitchen. From Max's point of view this was all going perfectly. He had successfully lured the boy into his lair and now intended to continue the work of corrupting the boy and turning him into his new sissy.

"Here we go." Max said as he pushed a bowl of peaches, pears and strawberries across the island to Jim. Jim dove in hungrily and began to eat the offered fruit. After he had consumed about half the bowl, Jim was feeling better about everything. Max was okay, he thought. He wasn't pushy and Jim was feeling a pleasant buzz from the beers he had consumed.

"Do you think my clothes are dry?" Jim smiled at Max.

"No. It's too soon. How about we play a little game?"

"What kind of game?"

"A game that will help you get in touch with your body's erotic zones. The strawberry game."

"The strawberry game? I never heard of it."

"Take your shirt off."

"My shirt? But I'll be naked!"

"Really?" Max chuckled. "You've been sitting here all this time, naked below the waist, with your pretty little cock and balls hanging out for all to see and you're shy about taking off your shirt?!"

"I just don't know."

"Look, honey, either you're an adult who wants to experiment and experience life and pleasure, or you're still a little boy who needs to run home to mommy so the big, bad man won't eat him up. Which is it? Are you an adult or a boy?"

"I see your point. I guess I'll be adventurous." Jim said as he stripped his shirt off.

Max selected a strawberry from the bowl and bit the end of the juicy fruit.

"Now, Max is going to squeeze some berry juice on a part of your body. Then Max is going to lick it off. When we are all finished, you will know which parts of your body are your most erotic zones. That way we can make you feel best when we play."

"O - okay." Jim warily responded.

Max smiled and walked around the island and sat on the barstool next to Jim.

"Just relax, baby boy. This will be fun."

And Max rubbed the strawberry on the tip of Jim's nose. He leaned forward and slowly licked the juice from the boy's nose.

"How was that?" Max asked.

"It was - nice."

Next Max rubbed the berry across Jim's lips, coating them with the sweet juice. Slowly, Max licked the boy's quivering lips.

"Stick out your tongue, baby." Max cajoled.

Jim complied and Max squeezed some juice onto the boy's little dart. Then Max covered Jim's mouth with his own and his tongue slithered into the boy's mouth. Max's tongue teased and massaged Jim's tongue as the boy responded eagerly to the invasion.

"Hah!" Jim gasped as Max released him.

Max rubbed the strawberry onto Jim's ear and licked inside and out, then gently biting the earlobe.

"Ooooh. Omigod!" Jim gasped with pleasure.

Max plucked a new berry from the bowl and held it up to Jim's lips.

"Bite the tip off, baby."

Jim bit and closed his eyes as Max rubbed the tip down his neck, over his chest and then squeezed juice over both of the boy's nipples. Max smiled approvingly as he noticed the boy's little five inch joystick doing pushups on the barstool. Then Max hungrily licked and gently bit the boy's neck. Max slowly ran his tongue from Jim's neck to his chest.

"Oh! Oh! Yes, Pleeeease!" the boy begged as Max flicked his nipple with his tongue and then gently bit down on it.

Max could see the boy leaking precum as he expertly worked first one nipple, then the other. Max stood from his chair and smiled down at the boy. In one motion, he took him under the arms and lifted him up, seating him on the island counter. Max smiled lasciviously as he squeezed and rubbed strawberry juice all over the boy's hard, throbbing little prick.

"Now Max is going to suck out all of your little boy-juice, slut!"

Max bent over the boy's crotch and he took the boy's tool in his hand. He squeezed it gently as he ran his tongue over the tip tasting a combination of strawberry juice and precum. Then Max slowly sucked the entirety of the little prick into his mouth. Max sucked slowly, but insistently while teasing the little love-stick with his tongue.

"Oooooh! Please! Please take me! Please take. . .! Pleeeeease!" the boy begged and squirmed as Max positioned his fuck finger at the boy's rosebud. Max slowly pushed his finger into the boy's asshole until he found his prostate.

"Omigod! Omigod! Omigod!" the boy screamed, frantically grabbing onto Max's head with both hands as Max sucked the juices out of his pulsating little prick. Spasm after spasm shook the boy as his cock spewed its juices into Max's mouth and his ass spasmed on Max's finger.

As the boy's spasms began to subside, Max slowly released the boy's still pulsing cock. Max smiled triumphantly at the quaking boy.

"Kiss me, slut! Kiss your cum from my mouth."

Max grabbed the back of the boy's head, holding him in place as his mouth covered the boy's and his tongue sought its new home. Jim tasted his own cum for the first time as his residual sperm slipped from Max's mouth into his own. When Max broke the kiss, Jim slumped into his arms, shaking and quivering.

"Good boy. Good boy. Good gurl." Max whispered as he lifted Jim into his arms and carried him into the den adjacent to the kitchen. Max sat down on the couch with Jim on his lap holding him tightly as he began to settle down.

It took ten minutes for the boy to finally stop quivering and breathe normally. Max held him the entire time and constantly ran his hands soothingly over the boy's body avoiding only his penis and his asshole. Max was happy with their progress, but he didn't want to scare the boy off. Still, it was time to test the boy's limits and see what could be achieved. Max ran his fingers through Jim's hair.