Tale of Two Sissies

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

"It's time to finish the game now, sweetie." Max said quietly.

"I thought we were finished." Jim responded.

"No. We made you feel good; very, very good. But now you have to play the strawberry game with Max's body."

"Ho - how?"

"Go to the kitchen and get a strawberry." Max ordered.

Jim stood up slowly, looking timid and confused. But he turned to the kitchen and walked to the island. While he did, Max quickly shed his own clothes. When Jim returned with the strawberry, Max was sitting naked on the couch with his legs spread wide. His thick, twelve inch cock began to twitch at the sight of the naked boy.

"Come here, baby. Don't be afraid of Daddy Max."

Jim walked over and stood in front of Max as if in a trance.

"Kneel, sweetie." Max ordered softly.

Jim slumped to his knees in front of Max.

"Now you will put the strawberry juice on Max and then lick it off, baby boy. Put the juice on Daddy's tongue."

Jim reached up tentatively and squeezed a little juice on Max's tongue. Max grabbed the boy by the arms and drew him into an enveloping embrace. Jim sighed in surrender and put his tongue on Max's tongue. Max hungrily opened his mouth and drew the boy into him. They kissed passionately, saliva dripping from the boy's mouth as Max ran his hands over the boy's back. Jim's tongue was bobbing wildly against his own as Max caressed the boy's ass and squeezed his ass-cheeks. Jim was out of breath by the time Max released his mouth.

"Put the berry juice on Daddy's nipples, baby gurl."

"Yes, sir." Jim whispered.

"No, no, you must call me Daddy from now on."

"Yes, Daddy." Jim whispered as he squeezed some juice on each nipple on Max's hairy chest.

"You know what to do now, sweetie. Lick the juice off of Daddy's nipples." Max breathed.

Jim put his hands on Max's hairy chest. He was surprised at how soft the black, curly hair was. Jim bent his head and licked one nipple, then the other.

"Suck them, baby gurl." Max gently commanded.

Jim began to suck on the left nipple like a little baby trying to drain its mother's milk.

"Oooh, yesss! That's good baby gurl." Max said as he cupped the back of the boy's head, holding him to his chest.

"Now the other one, honey. Make the other one feel good."

As Jim switched nipples, he could feel Max's huge tool throbbing against his chest. The tip was already moist with precum.

"Daddy needs berry juice on his man-cock, sweetie. Coat Daddy's man-cock with juice." Max instructed.

Jim detached from the nipple and moved the strawberry to Max's throbbing cock. He gently squeezed the berry and coated the cock with juice all over, tip to hairy base.

"Yesss, yesss. Now lick it and suck it. Take it in your mouth you little slut." And Max grabbed Jim's head and guided it down to his needy organ.

Jim licked tentatively at first; exploring this huge pulsating monster. Then he timidly placed his mouth over the head and licked precum from the slit. Then he slid the throbbing rod into his mouth. Max guided him and the cock sunk deeper and deeper into the boy's throat. He began to gag.

"Breathe through your nose, baby. Take it all."

Jim did as instructed and the cock slid further and further down. Jim began to gag a couple of times, but Max backed off slightly before further invading the boy's throat. As Max's cock pulsed in his mouth and throat, Jim could feel his own little prick harden and throb.

"Oh that's good, you little slut!" Max said approvingly. "Now I'm going to fuck your face until I cummm!" Max groaned as he began to rhythmically plunge his tool in and out of the boy's mouth.

Jim could feel his own body responding to the sexually charged atmosphere. He felt helpless and possessed with Max's throbbing organ inside his mouth and throat, pulsating with power. But he also felt excited and aroused as never before in his life. It seemed to take forever, but, finally, Jim could feel Max's cock begin to spasm. Max tensed up and then began to shoot load after load of semen down the boy's throat. Jim began to moan around the mouth-fucking cock as he felt his own throbbing, little tool begin to spasm and then shoot its load onto the floor. He didn't think Max would ever stop cumming. But finally, the deposits slowed and then stopped. Max held Jim's head in place as his cock began to soften in the boy's mouth. Then Max pulled out completely and lifted Jim back up to his lap and wrapped his arms possessively around the boy.

"Good boy. Good boy." Max said soothingly as his hands explored the boy's body, yet again. Jim's cock was still semi-hard. The boy shuddered as Max wrapped his hand around the softening prick and smoothed his thumb over the head.

"Did you cum, baby boy?"

"Ye -yes, Daddy." Jim whispered and hid his head in Max's chest.

"Good gurl. Oh yes, you're a good gurl." Max said approvingly.

"Did you enjoy sucking Daddy's man-cock, little gurl?"

"Yes, Daddy. Daddy?"

"Yes, little one?"

"Does that, does that make me gay?"

"Yes, little one. And Daddy will show you how to become his little gay sissy.

That thought frightened Jim and he felt that he must escape before this went any farther.

"I have to go." Jim said and popped up before Max knew what he was doing.

Jim ran into the laundry room. He quickly retrieved his briefs and shorts and put them on. When Max walked into the kitchen, Jim already had his shirt on and was pulling on the first sock.

"Where are you going, baby gurl?" Max stood there, totally naked, his huge cock hanging down in front of him, arms crossed over his hairy chest.

"I - I'm going home, Daddy. I don't think this was right. I have to go."

"Okay, honey. No one is going to stop you. You go home and think. Think about what your life can be. On the one hand, you can get some minimum wage job and wait for junior college to open for you. On the other hand, you can come back to Daddy. I'll help you release the sexy, little sissy that's hiding inside of you."

"I - I don't think I'll be back, Daddy." Jim answered.

"You'll be back, honey. You'll go home to your miserable little life and tonight you'll have a wet dream of what life can be like with your Daddy. And tomorrow, you'll think of Daddy and your little pecker will grow and you'll find yourself walking up the steps to Daddy's house. I'll expect you to knock on my door by noon tomorrow."

"No. No. I won't. I can't." Jim protested and then ran out of Daddy's house, eyes tearing.

Making of a Sissy - Jim to Jenni

When he got home, his aunt was laying on the couch, robe open, one sagging tit half-hanging out, in another one of her drunken stupors, chugging from a bottle of wine.

"It's about time you were home, you useless little bastard,!" his aunt slurred. "Go get me another bottle of wine from the fridge. And make sure you open it this time."

Jim complied with her request and then went back to the kitchen and popped a frozen dinner into the microwave. While he waited for it to heat up, his phone buzzed. It was a text from Max! Jim didn't remember giving Max his number, but even more disturbing was the contents of the text. The message was simple:

"Hello, slut! This message is so you think of me before you come to me tomorrow." The text was accompanied by two pictures. The first was a full shot of naked Max in all his hairy glory; his huge, flaccid cock hanging down almost to his knee. The second was a pic of Max's full erect cock, its tip glistening with precum.

At the sight of the pictures, Jim's little prick began to grow and harden in his pants. Jim stared, mesmerized at the pictures and he began to rub his crotch as he remembered the things he had done with Max earlier in the day. But those things were wrong! The microwave bell brought him back to the present and he closed out of IM and half-heartedly ate his dinner.

Bedtime was worse. He stripped down to only his briefs and propped himself up against a pillow thinking about the events of the day. Why had Max singled him out as someone who would respond to his sexual overtures? Why had Jim become so mesmerized by Max that he had succumbed to his stroking and fondling on the park bench? Why had he allowed himself to be led to Max's house? Max could have been a serial killer or a pervert! But weren't the things they did together perverted? Wasn't that type of sex condemned by society? Maybe not in this day and age when everyone seemed to have their own identity and their own "truth." But Jim wouldn't go back to Max's house tomorrow. He couldn't go back. He wasn't like that! He was a normal guy who had had a moment of weakness with an aggressive man.

The buzzing of his phone startled him. It was another text from Max. "Dream about me tonight, baby. Jack-off to the memories of today and the pictures I sent you. Come to me tomorrow and Max will make you cum!"

The pictures of Max were right above the IM. Jim clicked on the picture of naked Max and it filled the screen of his phone. Jim's prick began to immediately twitch to life. As he stared at Max's cock, Max's beautiful cock, remembering how it had tasted in his mouth, his own little love stick began to harden and throb. Jim groaned as his hand traveled down to his own little love-stick and he rubbed his hand over his crotch. Jim snaked his hand into his briefs and squeezed and fondled his little prick. He mewled like a little kitten as he swiped to the picture of Max's erect penis. He tore off his briefs and grabbed his stiff little love handle and began wildly stroking it.

"Oh shit! Oh yes! Ooooooh, pleeeease!" Jim moaned as little ropes of love juice began to spurt from his spasming prick. "Ooooh, no!" Jim sobbed as the last spurt deposited itself on the bed. "What's wrong with me? I can't do this, I just can't do this!"

He lay back in bed and scooted under the covers, tears streaming from his eyes. He knew what he had to do. He had to go back to Max's house tomorrow and tell Max that he wasn't doing this anymore. He would tell the man not to text him again, just to leave him alone. Finally, Jim fell asleep.

He awoke twice during the night; both times with a raging hard-on. And he relieved himself jacking off to memories of Max.

Max had said to return by noon the next day, but Jim was too antsy and worked up to wait long. He texted Max at nine-thirty: "Can I come over?"

"Yes, baby. Come to Daddy now." Max texted back.

Just before ten, Jim found himself standing before Max's door. His feelings were confused as memories of yesterday fought with his upbringing. But, resolved to end it, he knocked on the door. He could hear Max walking down the hall. Then the door opened.

"Welcome back, sweetie. I'm so glad you were anxious to come to Daddy. Enter Max's lair." And Max opened the door wide for Jim to enter.

Max was hardly dressed. He had on a pair of short pajama pants that came down to the knee - and nothing else. Jim could clearly make out the outline of Max's meaty appendage hanging down almost to the bottom of the pajama leg. And Jim was dismayed that his little tool was awakening in his own pants at the sight of barely clothed Max. Jim had come to end this relationship, but he realized that he had hardly dressed himself for 'serious' discussion. Jim was wearing another pair of khaki cargo shorts, a t-shirt and sandals.

"Let's go into the kitchen, baby boy." Max said, wrapping his arm around Jim's waist and leading him to the island scene of yesterday's fruit seduction. "Have you had breakfast yet, sweetie?"

"No, sir."

"How about some fresh fruit?"

"I - I don't know." Jim stammered.

"Don't worry, honey. Daddy won't be using strawberries to get you going today." Max chuckled as he began to prepare a bowl of fruit for Jim.

"Actually, sir. . ."

"Daddy. You are to call me 'Daddy'"

"Actually. . . . Daddy, I just came over to let you know that I won't be doing anymore of what we did yesterday. I think we should just not contact each other anymore."

"Well, then let's talk about that, sweetie." Max responded, sliding a bowl of fruit to Jim and opening the refrigerator to retrieve a bottle of milk.

"What makes you think we shouldn't pleasure each other again, baby?" Max asked as he poured a full glass of milk and slid it across the island to Jim.

"Well, I'm not really gay, Daddy. And the stuff we did yesterday was gay."

"Did you enjoy what we did?"

Jim speared a grape and thought while he chewed.

"I enjoyed it, Daddy. But isn't it wrong? I mean I'm not gay."

"Let me help you understand what you are, honey. Some boys grow up to be big, manly men, real men. That's what I am, a real man. I have a masculine body and a man sized cock meant for breeding good little girls and boys. I'm assertive and aggressive and dominant, just like a real man should be."

"But some boys grow up shy and submissive. They tend to have small, tender bodies with really little pricks that are really more male-clits than cocks. That type of boy is what I refer to as a sissy. You are a sissy, whether you realize it yet or not. As a sissy, your job is to serve real men. And you are going to start by serving me."

"What would you do to me?" Jim timidly asked.

"I'm going to turn you, baby. Any bit of masculinity you think you still have, I'm going to fuck right out of you. When I'm finished with you today, you will be my eager little sissy-bitch. You'll be Daddy's gurl."

"I - I can't, Daddy. I just can't." Jim pleaded.

"Yes you can, baby. And you will. And we have all day to recreate you. So relax, eat your fruit; drink your milk."

Jim was confused by Max, yet again. Had he tacitly agreed to what Max was proposing? He took a long draught of the milk and made a sour face.

"This milk tastes funny, Daddy."

"That's because it's sissy milk, sweetie. You'll come to like it."

"What's in it?" Jim asked after taking another drink.

"Well, milk, of course." Max chuckled. "And a healthy amount of Max's semen. A real sissy drink for my new sissy."

"I - I still think I should go, Daddy." Jim sighed as he downed the last of the sissy-milk.

"All we've done so far is talk, baby. But I'm guessing that our sexy talk has caused your little clitty to spring to life. Hasn't it, slut?"

"N - no, Daddy?"

"Let me see, baby." Max said and walked around the island over to the stool that Jim was perched on. Max spread Jim's legs, unzipped Jim's shorts, wriggled his hand inside and cupped his crotch. He could feel the little clitty doing pushups against the palm of his hand.

"Ooooh, no!" Jim moaned as his body responded to Max's touch and he ground his crotch into Max's engulfing hand.

"Oh, yes, you little slut. Hump Daddy's hand until your little clitty spits its juice."

The ache for release made Jim's inhibitions melt away and he was moaning and grinding his prick uncontrollably against Max's hand. He grabbed on to Max's shoulder to steady himself as Max squeezed his little prick driving him over the edge. With a little whimper that turned into a prolonged moan, Jim bucked his hips and spread his seed all over his undies and shorts and Max's possessive hand. Then he collapsed against Max laying his head on Max's shoulder, his body trembling.

"Good boy. Good boy." Max affirmed. "Good sissy. Good gurl." He said as he wrapped his arms around the boy and held him close.

Jim sighed resignedly as Max rubbed his back and squeezed his ass-cheeks.

"You got your clitty juice all over Daddy's hand, baby. Be a good gurl and clean Daddy's hand." Max said as he lifted his hand to Jim's mouth.

Jim hesitated, then stuck out his tongue and began to lick his own cum from Max's hand.

"That's right, sissy. Lick Daddy's hand clean and eat your own cum, you little slut."

Jim felt confused, foolish, ashamed and aroused as he licked Max's hand clean. He had come here to break off the relationship before it went any further. But here he was, mesmerized again by this man he had only met yesterday; doing things he never would have even considered two days ago. He couldn't just keep obeying Max's commands. But he also couldn't deny the physical effect Max had on his body. Jim had never experienced such pleasure and outright lust.

"Your pants are all wet, baby boy. Let's get you out of these clothes." Max said as he coaxed Jim out of his chair.

Max pulled Jim's shorts down over his ass and let them drop to the floor. Jim stepped out of them. Max put his thumbs in Jim's briefs and pulled them down dropping them to the floor. Jim stepped out of them. Max cupped Jim's ass-cheeks with both hands, squeezing and kneading.

"Mmmm, you have a nice little ass, baby-gurl; with a nice little boy-pussy just ripe for fucking." Max said as he rubbed a finger into Jim's crack and over his rosebud. "Let's get this shirt off you, too. Raise your arms, sweetie."

"Why do you call me a gurl sometimes and a boy sometimes?" Jim asked as he raised his arms and let Max strip his shirt off, leaving him totally naked and exposed.

"Because you're not really either, honey. Your body is very girlish, but you still have this little boy's love handle between your legs." Max said as he fondled Jim's little prick and balls. "You are just the perfect little sissy."

Max drew the boy into a close embrace, folding his arms around him and holding him tightly.

"You are my little sissy." Max breathed in Jim's ear.

Jim knew he should push Max away, grab his clothes and run out of here before this went too far. But he felt safe and snug in Max's powerful embrace. With his head nestled against Max's muscular, hairy chest, he was overcome by the musky scent of the man. And he could feel Max's hardening cock against his tummy, straining to free itself from the constricting pajama shorts to claim its prize. Jim went limp in Max's arms as Max began to lick and bite his neck and his ears.

"Time to take you to bed and breed you now, baby; time to make you Daddy's little sissy-slut." Max said as he picked the boy up and carried him like a virgin bride approaching the threshold of her new reality.

"Yes, Daddy." Jim sighed in surrender as Max carried him towards the staircase that led to the second floor bedrooms.

They ascended the staircase and Max carried Jim into the master bedroom. It was a very large bedroom with a huge bed, larger than any Jim had ever seen. The bed was covered with white satin sheets and pillowcases. A large jar of lube was standing on the nightstand next to the bed. The mirrored ceiling stated unequivocally that this was a boudoir as well as a place for sleeping.

A shiver coursed through Jim's body as he both dreaded and desired what was about to happen to him. Max nuzzled his neck and then licked from Jim's shoulder to his ear like a lion tasting its prey.

"Mine." Max stated matter-of-factly as he gently bit the trembling boy's earlobe and then teased the boy's inner ear with his thick tongue.

Then Max deposited the boy onto the bed. He quickly stripped off his pajama bottoms and his massive cock sprang free. Jim could see that it was hard and throbbing and leaking a copious amount of pre-cum. Max had a devilish smile on his face as he crawled onto the bed towards Jim. Afraid, Jim backed away until he was in the middle of the huge bed. Max simply smiled a predatory smile and grabbed Jim's ankle to halt his progress. Max slowly crawled toward the boy. Jim lay back, helpless. Max crawled onto him, his large body totally engulfing the boy as Max's mouth found Jim's and Max plunged his tongue into the helpless boy's mouth. The kiss seemed to last forever as Max's tongue explored and licked and teased; drool leaking down the side of Jim's cheek as Max's tongue hungrily explored.

Jim had never been so overwhelmed in his entire life. Max's musky odor was overwhelming and Max's huge cock throbbing and pulsing against Jim's thigh made the boy feel helpless and possessed. Jim could feel his own body begin to respond. Even though he had just shot his load in the kitchen, Jim's little prick was growing and hardening again as Max's hand began to explore his body.