Family Issues Ch. 01

"That scar of hers and the eyepatch," Kevin said. "Helen scares me."

"I know. A bit of a freak show," Diana shrugged. "You'll get used to it."

"No, I meant that I get the feeling that she hates me."

"Helen hates all of my boyfriends. But don't you worry your pretty little head about it. It doesn't mean that she'll do anything about it. She'll simply ignore you."

"What happened to her? A car accident?"

"Are you seriously going to stand here naked and talk about my bitch sister? Come here this instance, beautiful. You owe me an erection since you stole the last one. Use that kitten tongue of yours to lick me proper instead of wagging it." She stretched her back on the bed and opened her thighs.

Kevin crawled quickly between the warmth of Diana's parted legs.

"So eager? Good boy." Diana placed her hands behind her head and sighed happily at the ceiling. Kevin eagerly took the base of her cock in his small hand and licked through her length with his soft tongue. Once her cock was slick with his saliva, he pulled the mushroom head deep into his velvety mouth.

Life was so good. In fact, if it'll get any better Diana figured that she might explode. "You'll be bringing your stuff in here tomorrow. Did I tell you to stop? Don't give me that puppy look, Kevin. Being a couple means living in the same house and sleeping in the same bed. That's what grownups do."

He nodded, and his cheeks caved in around her sensitive tip as he sucked.

"Oh, that was great. Do that thing again with your tongue. Like you were trying to burrow into the slit. Good boy. Good boy. We'll make a decent cocksucker out of you yet."

After that, she went quiet. Just happy to give in to Kevin's hot mouth. It was in cahoots with his plush lips and soft tongue, working their magic on her girl-cock. For some time later, there was no talk just the sound of his lips sucking air around her pulsing shaft, and the obscene symphony when his lips swallowed the head and rolled all the way back to the tip.

"Jesus. No way! I'm about to pop again."

Kevin smiled, his mouth still on her cock.

"No way, baby. It's time. Raise your head. I need five!"

"Time for what?" His voice was shaky because he wasn't born yesterday. He knew what girls like her did with boys like him.

"Don't worry, sweetie; we'll take it slow." She pulled herself into a lotus pose. Her massive cock was pointing skyward.

"But you're huge, Diana. It can't..."

"I'm only three inches."

"Are you counting in dog years?"

"Three inches wide from the base to the tip," she gave her devilish giggle. "Don't worry baby, we're going to do this with a ton of lube," she winked. "It's in the drawer."

Kevin found the blue gel tube. Diana leaned back and nodded in the direction of her massive member. Kevin poured a generous amount on it. His ass was quivering from the stress.

"Breathe, baby, in and out. The key is to relax."

"Easy for you to say."

"It'll be fine. You're not my first virgin. Now squat!"

Kevin stood up on the bed, facing her, spread his legs and lowered himself slowly to her waiting embrace. He clasped her fat cock, firmly, and aimed it at his quivering starfish. The spongy head bumped into the tiny entrance. Kevin shuddered. "No, I'm sorry, I'm..."

"Come on."

"I can't... I can't do this, Diana. I thought I could, but I just can't."

"Okay, so just the tip."

"Just the tip?"

"Just the tip. You've been such a good boy tonight; I think I can cut you some slack."

"Just the tip." He lowered himself further. The slippery head moved up and away from his starfish and Kevin fell into her lap. Diana giggled.

"Hey."

"Your tiny boy clit is so cute."

"My what?"

"Look," Diana pointed down. Their cocks stood head to head, touching. More precisely, head to belly, because Big Bird dwarfed Kevin's cock both in length and girth. "Your little chick looks like Big Bird's little brother. It's like a boy clit."

"Stop it."

"I'm fucking with you, baby."

"Not funny. I thought we were trying to fuck, not fuck my self-esteem. "

Diana smiled and kissed his lips. She had managed to convince him to deflower himself, which added a sweet cherry to the top of this beautiful boy cherry popping.

Kevin rose up again. This time he closed his warm hand on her massive cock and held it firmly. He aligned it until it nestled on the starfish's opening, then shuddered and lowered himself down. Diana's cock was slippery and didn't breach his virgin hole, so he tried to coerce it into the opening with his fingers.

"It's impossible, Diana, that's like stuffing an anaconda into a coke bottle."

"Try harder."

The young man laid one arm on her shoulders and used it to steady himself as he slowly skewered himself on the thick spear. His expression transformed as his small sphincter yielded around her fat knob. Millimeter by agonizing millimeter he felt his ass opening, as more of the big intruder claimed him. Kevin huffed like he was giving birth and his brow had lines of sweat.

Diana's legs started shaking. There was no denying the insane effect this young boy had on her body. His amazing eyes, tight body and scent combined to a senses overload. On top of it all, Kevin's sphincter was giving her sensitive head a firm massage. Despite everything Diana didn't close her eyes and didn't surrender to the pleasure. She stared at him, not even blinking, unwilling to miss even a heartbeat of her conquest.

After several minutes heavy breathing Diana's patience ran out, and she decided to give Kevin a helping thrust. His Scream went through the roof and the bulbous head through the quivering muscle, into the tight Embrace of his ass. The sphincter closed around the bulbous head and locked it inside a loving prison.

Kevin tried to scream again, but nothing came out of his mouth. "It hurts, it hurts, take it out."

Diana lifted him, and the burning pain returned as the head jammed into the closed muscle.

"Don't take it out, don't take it out. Just stay still! Don't move!"

"Take it out, leave it in. I think you misunderstood the roles in this relationship."

"It hurts," There were tears in his eyes.

"Don't be a pussy."

"Let's just wait till you go soft again, and then you can pull yourself out."

"Might take hours."

"I don't care," he huffed, "don't fucking care."

"Kevin, baby, so that you know, you're officially the best piece of ass I ever had the fun to visit." Diana placed her hands on top of Kevin's thighs and pulled.

"No," he huffed, "no."

Slowly but surely her cock conquered his super tight tunnel.

"P... P... Pull it out."

"Oops, sorry," she laughed, and instead of pulling it out she drove it deep into his rectum.

"Uhnnggghhh," he grunted loudly as she continued penetrating, stretching parts of him that weren't meant to be stretched so far. His ass was clenching and unclenching, driving her pleasure to peaks she never conquered before.

"Baby, your ass is so good, I just can't wait any longer," Diana forced herself balls-deep inside poor Kevin. His ass cheeks came to rest on her thighs. He screamed again, but she muffled it with a loving kiss, tonguing him deeply. She continued to kiss him while she began to withdraw her massive cock from his aching ass and then feed it back in. He tried to push her away, slapping her frantically like a blind man. He just wanted to escape the giant cock that was rearranging his insides. Diana loved those moments of deflowering. She pinned his arms to his body, and her stroke increased.

Kevin tried to squirm free. His attempts made his ass squeeze hard, sending Diana over the edge.

She thrust harder and faster, exploding a torrent of white cum deep in his bowels. Each thrust lifted him up from the bed, jerking him violently. When she was spent, she hugged him tight and rested her head on his shoulder.

Kevin felt lost. There was nowhere to run. His head sank between her little breasts, and he concentrated on breathing.

"Sorry about that baby."

"No, you're not." Kevin's face was red and tearful. The pain subsided, but the humiliation only grew when he reflected on the situation. He wanted to run away, but he simply couldn't find the energy to lift himself. "That was cruel, Diana. I thought you said you liked me."

"Sweetie, you were a virgin. The first time is always the hardest, but you'll soon learn to love it. I promise."

"What if I won't?"

"You're already starting."

"Are you mental, Diana?"

"Then why is your stomach so wet with your own cum?"

Kevin looked. Sometime during his ass ravaging he ejaculated on himself. He was too focused on the pain to notice. "It wasn't fun and I didn't like it, Diana. You said, 'just the tip.'"

"Oh, grow up for fuck sake." Diana lifted him, and her soft cock plopped from his ass. A stream of baby making juice followed it and dribbled down his legs. She lay down on her side and motioned him to spoon into her.

Kevin stared at her. She must be the most self-centered person he had ever met. When something didn't go as planned or wasn't to her liking, she just pretended it didn't happen.

"Well?" She said. "I need a good cuddle."

"I need to wash, Diana. I got to call my dad; he'll be worried."

"Call him."

"I think I left my phone on your sister's desk when I showed her the contract."

"Be super quick about it. I wanna sleep."

$$$$$$$$$$$$$$$$

Helen had an intense masturbation session on her bed. She usually used Jaime Lannister's photo, but tonight she had a new image etched deeply in her mind, that of the naked lithe form of Kevin.

"Oh Kevin," she whispered at the ceiling. "You're as beautiful as a Michelangelo Statue. You want me bad, don't you? Yes, you do. You like older women with a massive credit card, don't you? Well, I have something massive for you. Do you feel it inside you? You feel super amazing, Kevin. Oh..." Her body was already hot, and it needed little encouragement before it went over the edge and she had to change her wet sheets. Then, she had to replace them for a second time. On the third session, she sat on her bathroom's toilet, because enough was enough. She closed her eyes and pictured Kevin's purple eyes as she rubbed her rigid pole.

Diana was right. There was just something irresistible about the young man. She told herself to let it go, that it was only a weird state of horniness that overwhelmed her tonight. But as she imagined Diana and Kevin squirming passionately on her sister's big bed, Diana's body going like a piston up and down between his thighs, Helen felt a nasty pang of envy.

Why couldn't it be her for once instead of Diana? What if she told Kevin that he must to be her boyfriend?

Helen stared at her image in her bathroom mirror. She scratched the eyepatch and then trailed her finger along her scar, down all the way below her neckline, where more scars awaited.

"He would probably run for the hills; you freak," she told her image, sighed, and went outside for a drink.

Someone was in her study. She saw Kevin's willowy form as he picked his phone off her desk. He wore boxers only, and his back was flushed with exertion. Kevin dialed a number but hung up immediately, wiped his eyes, and breathed deeply. He then he sat down, buried his head in his palms, and cried silently.

Helen's maternal instinct kicked into gear. A minute ago, in her imagination, he was just ass and lips for her pleasure. The dissonance between the imaginary sex toy and the real broken boy that was sobbing in her study, made her heart ache. Shame overwhelmed her. She wanted to go over and hug him. To tell him that everything is going to be alright and that they'll figure it out together somehow. But then he composed himself and dialed.

"Dad," his voice was shaky, and he was trying very hard to control it. "Yeah, I'm sorry that I didn't call you earlier. It took longer than I thought it would. No, no, everything is all right. Everything is-" He froze in mid-sentence because he finally noticed Helen standing in the hallways and staring at him. The look of pure hate he gave her, hit Helen's stomach hard.

"Sorry. No, nothing, I hit my toe on the... No, I'm okay. Really. I just sound like that because I ran up the stairs. Don't worry. I met the new landlord. Yeah, I told you I would I sort everything out. Yeah. She is. My new landlord is also a futa lady, like Mrs. Lewinski. Yeah, one of them dickgirls. No, this one's not pretty at all." Kevin straightened his back and stared at Helen, defiant and hateful. "In fact, she's as ugly as fuck. On the inside as well as on the outside. But I managed. It's okay. I've made a deal to sort out my debt. I'll call you tomorrow. Love you too."

Kevin hung up the call and went past Helen, back to Diana's bedroom. He didn't look at her or even acknowledge her existence. She felt transparent. Helen stared at Kevin's back and then stood in the hallway for a long time after he was gone. The big clock in the dining room and her only memory left from her mother chimed Twelve O'clock. She shuddered and ran back to her room, fell on the bed, covered her head with her pillow and cried for a very long time.

To Be Continued