Chapter 2: Building Tension
The sun had set, casting the city in a cloak of twilight, as JT found himself standing in Kendall's opulent living room, his heart pounding in his chest like a drum. He had been summoned, not by a phone call or a text, but by a curt note delivered by a stern-faced assistant. "Kendall requests your presence at her penthouse this evening," it read, as if he were a servant being summoned to the queen. And in a way, he felt like one. He was, after all, just her assistant, her plaything, her toy to tease and torment.
And as he stood there, his heart hammering in his chest, he felt a familiar stirring in his pants. His cock twitched, already half-hard at the thought of seeing Kendall again, of being at her mercy.
The penthouse was quiet, the only sound the soft hum of the city below. JT took a deep breath, steeling himself for whatever Kendall had planned. He didn't have to wait long. The sound of heels clicking on marble echoed through the vast space, and then Kendall was there, standing in the doorway of her bedroom, her eyes locked onto his.
She was dressed in a sheer robe, the material so thin that it left nothing to the imagination. JT could see the outline of her nipples, the dark triangle of hair at the juncture of her thighs. His cock twitched, hardening even further at the sight of her.
"Kendall," he managed to choke out, his voice barely above a whisper. "You wanted to see me?"
She smirked, her eyes gleaming with amusement as she sauntered towards him. "Oh, darling," she purred, her voice a low, sultry growl. "I always want to see you.
You're my favorite little plaything, aren't you?" Kendall stopped in front of him, her eyes locked onto his, her breath hot on his face. She reached out, her fingers trailing down his chest, making his nipples harden. His cock was rock hard, straining against his pants, aching for more.
"But tonight, darling, I have something special planned for you," she whispered, her voice a low, sultry growl. She stepped back, her eyes never leaving his, and untied her robe.
It fell open, revealing her naked body to him. Her tits were perfect, round and firm, her nipples hard and dark. Her stomach was flat, her hips curvy, and her pussy was bare, her lips glistening with arousal. JT's cock throbbed, pressing painfully against his pants. He wanted to touch her, to taste her, to fuck her.
"Take off your clothes, darling," she commanded, her voice a low, sultry growl.
"I want to see that tiny little cock of yours."
JT hesitated for a moment, his eyes locked onto Kendall's naked body, his cock throbbing. He knew she was going to humiliate him, knew that she was going to taunt him, but he couldn't help himself.
He reached for the hem of his shirt, pulling it off in one fluid motion. He tossed it to the side, his eyes never leaving Kendall's body.
He could see her nipples hardening, could see the desire in her eyes as she watched him strip. He unbuttoned his pants, pushing them down his legs along with his boxers, until he was standing before her completely naked.
Kendall's eyes flicked down, taking in his cock. She smirked, her eyes gleaming with amusement. "Well, darling," she purred, her voice a low, sultry growl. "That is even smaller than I remembered."
JT felt his cheeks flush with embarrassment, but his cock twitched, aching for more.
He couldn't help it, he was turned on by Kendall's dominance, by her humiliation. He was a fucking mess, and he loved it.
Kendall sauntered towards him, her hips swaying, her tits bouncing with each step. She reached out, her fingers wrapping around his thigh, making him gasp. He was so hard, so fucking hard, and her touch sent electric shocks through his body.
"God, you're pathetic," she whispered, her voice laced with amusement. Let’s take this to my room.
I want to play with you properly there." Kendall said, her voice a low, sultry growl. She turned and walked towards her bedroom, her hips swaying, her ass bouncing with each step. JT followed, his eyes glued to her body, his cock throbbing with anticipation.
The bedroom was dimly lit, the only light coming from a small lamp on the bedside table. The bed was massive, the sheets a silky black, and the pillows piled high. The sound of giggling came from the closet as Kendall turned around to shush her friends who she secretly invited.
"Good evening, ladies," Kendall said, turning back to JT who was still naked, standing awkwardly in front of her. "I'm so glad you could make it."
JT blushed at the thought of being paraded before Kendall's friends. He had masturbated to images of them and now he was here, standing in front of them, all because of Kendall.
Bella, the most dominant of Kendall's friends, stepped forward to inspect JT's body.
She stood tall, her sharp features highlighted by the dim light. "Well, well, well," she said, narrowing her eyes at JT's tiny cock. "Looks like Kendall wasn't exaggerating, you really are an insignificant little thing, aren't you?"
JT swallowed hard, his eyes locked onto Bella's face, willing himself to stay hard despite her words. He wanted to impress Kendall's friends, to prove himself to them.
Kylie, Kendall's sister, stepped forward next.
She had always been known for her no-nonsense attitude, and her evaluation was equally as humiliating as Bella's. "He's a weak little thing, isn't he?" she said, her voice laced with disdain. "I bet he can't even last a minute in bed. I mean, look at him.
He's so small, he's practically non-existent." Kylie chuckled, her eyes gleaming with amusement. "Kendall, why do you bother keeping him around?
He's so tiny, he's practically useless," Bella said, a cruel smile spreading across her face.
JT could feel himself growing softer with every word they said, his cheeks burning with embarrassment. He knew his small size was a turn-off for most women, but he never expected it to be thrown in his face like this.
But despite the humiliation, he couldn't deny the fact that his cock was still aching for attention. It was a confusing mix of emotions, and he didn't know how to process them.
But before he could dwell on it, Kendall's voice cut through his thoughts.
"Don't just stand there, darling," she said, her voice laced with amusement. "Come here and let me introduce you to my friends properly."
JT hesitantly stepped forward, his eyes flicking between the four women. He recognized them all – Bella, Kylie, Elsie, and Hailey – from the countless tabloids and magazines he'd scoured for pictures of Kendall. They were all stunning, each in their own way, and he felt like a small, pathetic worm standing before them.
Kendall's eyes gleamed with amusement as she watched him squirm.
"Girls, this is JT," she said, gesturing towards him. "My new assistant, and my new... toy."
The women chuckled, their eyes roaming over his naked body, lingering on his cock. JT felt his cheeks burn with embarrassment, but his cock twitched, loving the attention.
"Turn around, darling," Kendall commanded, her voice a low, sultry growl. "Let them see all of you."
JT hesitated for a moment, then turned slowly, showing off his ass, his back, his everything.
He could feel their eyes on him, could feel their amusement, their judgment. He wanted to cover himself, to hide, but he knew better than to disobey Kendall.
She walked around him, her heels clicking on the hardwood floor, her eyes never leaving his body. She stopped in front of him, her hand reaching out, her fingers wrapping around his chin, tilting his head up to look at her.
"You're pathetic, you know that?" she whispered, her voice still laced with amusement. "But you're mine.
My little plaything. My little simp," Kendall continued, her voice dropping to a low, sultry growl. She released his chin, her hand trailing down his throat, his chest, his stomach, until it reached his balls. She wrapped her fingers around them, making him gasp. "Isn't that right, darling?"
JT nodded, his eyes locked onto Kendall's, his cock throbbing above her hand. "Yes," he managed to choke out. The pain and tension making it difficult to speak.
"Answer me, little man," Kendall snapped, squeezing harder.
"Y-yes," JT stammered, his eyes watering. "I'm yours."
Kendall released his balls, making him breathe a sigh of relief. But it was short-lived. “Now JT I can see you’re familiar with everyone in here even though you’ve never met. Would you like to tell my friends how you know them?” Kendall asked, her voice dripping with mock innocence. JT's face turned beet red, and he couldn't meet anyone's gaze. “Come on, darling,” Kendall prodded, “Don't be shy. Tell them how you've jerked off to their pictures, how you've dreamt of fucking them.”
The room was filled with their giggles and the sound of Kendall's heels clicking on the hardwood floor as she paced around JT. He could feel the weight of their stares, the pity, the amusement, the disgust. He wanted to disappear, to sink into the floor and never come out.
But he knew better than to disobey Kendall. He took a deep breath, steeling himself for what was to come. "I-I've seen their pictures," he admitted, his voice barely above a whisper. "I've... I've jerked off to them."
The room erupted in laughter, the sound echoing off the walls. Kendall smirked, her eyes gleaming with amusement. "There you go, darling," she purred. "Always so honest. It's one of the things I love about you."
She walked around him, her fingers trailing along his skin, making him shiver.
She stopped behind him, her hands gripping his shoulders, her nails digging into his flesh. He could feel her breath on his neck, her tits pressing against his back.
"Now tell them each how you’d fuck them if you were a real man," she commanded, her voice a low, sultry growl. "Let my friends get a good look into that kinky little mind of yours. How about you start with Kylie. Could that little cock even reach past her ass?"
Kendall laughed, looking at Kylie who smirked back at her. "Alright, darling," Kendall said, turning her attention back to JT. "Let's hear it. How would you fuck my sister if you were a real man with a real cock?"
JT's face turned beet red, but his cock throbbed at the thought. He tried to push the image out of his mind, but it was no use. He could see Kylie's large breasts, her round ass, her wet pussy. He could picture himself behind her, gripping her hips, slamming into her. But he knew he couldn't say that.
Not here, not now, not with Kendall's friends watching, laughing, waiting. So, he took a deep breath and said the first thing that came to his mind. "I-I'd grab her hips, pull her onto me, slam into her. Hard. Over and over again. Until she screamed my name."
Kylie smirked, her eyes gleaming with amusement. "Is that right, little man? I’d scream? And what about Hailey? How would you fuck her?"
JT's breath hitched as he turned to face Hailey. Her face so much prettier in person.
He had always fantasized about her perfect lips giving a sensual blowjob. The thought of it made his cock twitch, and he swallowed hard, trying to find his voice. "I-I'd pull her hair, fuck her mouth," he managed to choke out, his voice barely above a whisper. "Make her deepthroat my cock, make her take it all."
Hailey's eyes widened slightly, but she didn't look away. Instead, she licked her lips, her tongue darting out to wet them. "Is that right, little man?" she asked mockingly, her voice a low purr.
"And what about Bella? How would you fuck her if you were a real man?"
JT's eyes flicked to Bella, her sharp features and dominant aura making him shiver. He knew she was a formidable woman, both in and out of the bedroom. He took a deep breath, trying to find the right words. "I-I'd bend her over, spank her ass until it was red," he admitted, his voice barely above a whisper. "Then I'd fuck her hard, make her take every inch of my cock. Make her beg for more."
Bella smirked, her eyes gleaming with challenge.
You think you could handle me?"
JT swallowed hard, his cock throbbing at the thought. He knew he couldn't handle Bella, not really. But he liked the idea of trying, of pushing himself to his limits.
"Elsie," Kendall said, turning to her friend. "Why don't you help our little man here? Show him what a real woman feels like."
Elsie smiled, her eyes twinkling with mischief.
She was a beautiful woman, with big natural breasts and a perky round ass. She was also the most sympathetic to JT, but she wasn't attracted to him because of his small penis. She sauntered towards him, her hips swaying, her dress riding up her thighs. She stopped in front of him, her hand reaching to rub his thigh.
"Poor little thing," she cooed, "So tiny, so hard. I honestly didn’t know penises could be this small. I know that must be so frustrating for you.” Elsie's hand moved higher, her fingers brushing against JT's balls, making him gasp. "How about I help you out, little man? Let me show you what a real woman feels like."
She gave his balls a playful squeeze then pulled him in for a hug. Her breasts pressed snugly against his chest sent chills through his body. She then began to slide her panties off to give to him.
“Here, put these on, little man. I want you to wear them while I tease you.” She said, her voice dripping with mockery. JT hesitantly took the panties, feeling the warmth and smoothness of the fabric from where her pussy had been. He put them on, his small cock tenting the tiny garment. He felt ridiculous, but also incredibly turned on.
Kendall laughed at the sight of him. “Look at you, darling. You look like a runway model. You can barely even see your little bulge.” The girls were dying of laughter at the sight. JT had never felt so embarrassed yet he felt his cock stirring with arousal. His throbs restrained by the tight red lace panties.
His cock twitched as Elsie's hands moved to his chest, her fingers playing with his nipples, making them harden. She was teasing him, playing with him, and he fucking loved it.
"God, you're so tiny," Elsie whispered, her voice low and sultry. "I can't believe Kendall keeps you around with all the big dicks she fucks. I’m sorry you’re not one of those lucky big guys"
JT could feel his cheeks burning with embarrassment, but his cock was rock hard, aching for more.
He couldn't help it, he was turned on by the humiliation, by the way Kendall and her friends were treating him. He could tell they were amused by seeing the type of weak fan who jerks off to there photoshoots was like.
They were all looking at him, laughing as if he was some sort of joke. He hated it, but his cock was throbbing, loving the attention. He wanted to prove himself, to show them that he was more than just a pathetic little assistant.
But before he could say anything else, Kendall's voice cut through his thoughts. "Enough talk, darling," she said, her voice laced with amusement. "It's time for some action. Elsie, why don't you sit on the bed with the girls I think you’ve given JT more than he’s ever felt from a woman. JT that was some big talk earlier telling them all how you’d fuck them. Now let’s see how tough you are in front of them all when you’re stroking that tiny cock in front of them?"
Kendall taunted, her eyes gleaming with mischief. "Show us all how you'd fuck us, little man. Show us what you've got."
JT's breath hitched, his cock throbbing at the challenge. He knew he was small, knew he couldn't compare to the men Kendall usually fucked, but he wanted to prove himself. He wanted to show her, show all of them, that he was more than just a pathetic little assistant.
He took a deep breath, his eyes flicking between the four women. They were all watching him, waiting, their eyes filled with amusement and challenge.
JT could feel the weight of their stares, the expectation, the humiliation. But his cock was hard, aching for more, aching to prove himself.
He took a deep breath, his eyes locked onto Kendall's. He could see the challenge in her eyes, the dare. She wanted him to fail, wanted to humiliate him further. But he wasn't going to give her the satisfaction.
He reached down, his fingers wrapping around the elastic of the red lace panties Elsie had given him. He pulled them down, his small cock springing free, hard and aching.
He could hear the girls giggle, could see the amusement in their eyes, but he didn't care. He was past caring, past feeling embarrassed. All he cared about was proving himself, showing Kendall that he was more than just a pathetic little assistant.
He gripped his cock, his fingers barely able to wrap around it. He started to stroke, his hand moving up and down, his breath coming in short gasps. He could feel the heat building in his balls, could feel the tension coiling in his stomach.
"Come on, little man," Kendall taunted, her voice laced with amusement.
"Show us what you've got. Jerk that tiny cock for us. Let's see how long you can last before you embarrass yourself."
JT gritted his teeth, his hand moving faster, his grip tighter. He was determined to prove Kendall wrong, to show her that he could last, that he could make himself last long in front of her and her friends.
"Oh, look at that," Bella mocked, her voice dripping with disdain. "He's actually trying.
I'll give him that," Kylie commented, her eyes gleaming with amusement as she watched JT's hand move furiously up and down his tiny cock. "But look at the size of it. It's like a fucking pinky finger."
The girls chuckled, their eyes locked onto JT's small dick. He could feel their stares, their amusement, their pity. He was terrified he’d cum prematurely from all the teasing. He knew he had to last long to impress them at all.
His hand moved faster, his grip tighter, his breath coming in short, sharp gasps. The sound of his hand slapping against his skin filled the room, the wet noises of his pre-cum lubricating his strokes.
"That's it, little man," Kendall taunted, her voice a low, sultry growl. "Faster. Harder.
JT's hand moved faster, his grip tighter, his cock throbbing, aching for release. He could feel the pressure building in his balls, could feel the tension coiling in his stomach. The girls began to tease in different ways to excite and overwhelm him. Elsie spread her legs she was still bottomless from giving JT her panties and she began to finger herself. Kylie revealed more of her boobs and jiggled them while laughing. Hailey seductively began to suck on her fingers as if she was giving a blow job. Bella sat unimpressed hurling insults at JT.
"Look at the size of that pathetic dick. Even if you could last, which you won't, there's no way you could satisfy any of us with that tiny thing. You're a joke, little man. A fucking joke."
JT's hand moved faster, his grip tighter, his knuckles white with effort. He was determined to prove Bella wrong, to show her that he could last, that he could make himself last long enough not to cum prematurely in front of them all. But the humiliation, the constant attacks on his masculinity, were taking their toll. Seeing the women he had fantasized and jerk off to so many times tease him had him on the edge of cumming.
He could feel the pressure building in his balls, threatening to spill over. He was determined to hold out, to prove himself, but it was getting harder and harder to resist the urge to cum. "You can do better than that. Show us what you've got. Make us believe that tiny cock of yours can actually pleasure a woman." Elsie encouraged. He was panting now, his breath coming in short, sharp gasps. He couldn’t stop imagining all the ways he said he’d fuck them. He knew he could never handle that. Now he was about to bust embarrassingly fast in front of them all.
He couldn't hold back any longer. He was going to cum, and he didn't want to, not like this, not in front of them. "I-I can't," he stammered, his hand slowing down, his grip loosening. "I'm going to cum."
Kendall smirked, her eyes gleaming with victory. "That's right, darling," she purred. "Cum for us. Show us what you normally do to our pictures.” Kendall demanded, her voice dripping with mockery. “Show us how you jack off to us, thinking how you’d fuck us. Show us how you’d cum thinking about our bodies that are too hot for you to handle.”
JT began to whimper as his legs began to shake. He was past the point of no return and it was the most intense feeling he ever had. It had barely been more than a minute of stroking and he was going to cum in front of his celebrity crushes further embarrassing himself.
His body was no longer under his control. He was at the mercy of his hormones and the humiliating words of Kendall and her friends. His balls tightened, his cock throbbed, and with a final, desperate stroke, he came undone.
"Fuck!" he cried out, his body convulsing as he came. Strings of cum shot out of his cock, landing on the floor, on his hand, and even on his stomach. He continued to stroke, milking every last drop out of his tiny cock, his body shaking with the force of his orgasm.
He couldn't open his eyes, couldn't look at the women he had just cum in front of. He could hear them gasp and laugh at his quick performance He was mortified, humiliatingly so, and he just wanted to disappear.
But Kendall wasn't going to let him off that easy. She walked over to him, her heels clicking on the hardwood floor, her voice laced with amusement. "Well, darling, that was quite the performance," she said, her hand reaching out cupping his balls.
"I've never seen anyone cum so fast. You must have been really thinking about us, huh?"
JT could only nod, his cheeks burning with embarrassment. He knew he should feel ashamed, humiliated even, but his cock was already hard again, aching for more attention.
Kendall smirked, her eyes gleaming with mischief. "I bet you are. I bet you've been dreaming about fucking us, about making us cum on that tiny cock of yours."
She squeezed his balls, making him gasp.
"But you know what, darling? I think you need a little punishment for that pathetic display." Her voice was sweet, but her eyes were cold. "You've embarrassed yourself, and worse, you've embarrassed me in front of my friends. I can't have that, now can I?"
JT shook his head, his eyes wide with fear and anticipation. What did she have planned for him? "Good boy," she purred. "Now, let's see.
What kind of punishment would be fitting for a little worm like you?" Kendall mused, her fingers still playing with JT's balls, making him squirm. He could feel his cock stirring again, aching for more, despite the humiliation he had just endured.
Kendall looked over at her friends, her eyes gleaming with mischief. "Girls, any ideas on how we should punish our little man here?"
Elsie smirked, her eyes twinkling with mischief. "How about we make him eat us out?
After all, he's clearly desperate for some female attention," Elsie suggested, her voice dripping with mockery. The other women nodded in agreement, their eyes gleaming with excitement.
Kendall grinned, her eyes locked onto JT's. "I like that idea," she said, her voice laced with amusement. "What do you say, darling? Ready to earn your place here?"
JT gulped, his eyes flicking between the four women. He knew he had no choice, knew he had to do whatever Kendall told him to. He nodded, his voice barely above a whisper.
"Yes, Kendall."
Her smile widened, and she turned to her friends. "Alright, girls. Let's see what our little man can do."
Elsie, Kylie, Hailey, and Bella began to undress, their clothes falling to the floor in a heap. JT's eyes widened as he took in their naked forms, his cock hardening at the sight. He had seen their pictures, had jerked off to them countless times, but nothing compared to seeing them in the flesh.
Kendall pushed him down onto his knees, his face level with their pussies.