Consoling Casandra

John watched as the tear rolled down her cheek. She discreetly brushed it away while keeping her head down, partially covered by the black veil she wore in mourning. He couldn't believe his boss, Mr. McMahon, had suddenly dropped dead from a heart attack at only 45 years old. Of course, John also found it hard to believe that the beautiful young woman across from him at the grave site was his boss's daughter. He remembered once seeing a picture of Casandra on his boss's desk and assuming he'd landed a hot young piece of ass as a trophy wife. Of course, when he said as much to Mr. McMahon, the man immediately snapped at him that the beautiful young girl was his daughter and that if he tried anything with her it'd be over his dead body.

He snickered suddenly at the irony, causing Mr. McMahon's wife and daughter to both glance up in his direction. He tried to cover his inappropriate laugh by clearing his throat, but for just a moment, his boss's daughter caught his eye before bowing her head once more.

After the service ended, everyone came by the McMahon's home to offer their support and pay their respects to the family. John felt awkward showing up to the house given that he'd only met his boss's wife once or twice. He always felt this tradition was intrusive too, forcing a grieving family to host the after-party for their loved one's funeral. But oh well, he thought. At least there's food and drinks.

As John walked through the house, he said his hellos to colleagues from work and tried to stay out of the way mostly. At one point he saw Casandra sneaking some hard liquor into her drink. She had lost the veil between the cemetery and here, it seemed. Though he knew 19 was hardly old enough to drink, he figured the circumstances warranted a little empathy. In camaraderie, he poured himself another glass as well. When in Rome and all that.

After an hour or so, with the alcohol and stories flowing about Mr. McMahon, John could feel the shift in the room from grief to nostalgia. He considered leaving but realized this was a great networking opportunity, as shallow as it might sound. He stood around the living room with coworkers who knew Mr. McMahon much longer than he and laughed along at their tales of his early years in the company. John soon found himself distracted however when he heard whispered arguments down the hall.

"Can't you just tell them to leave?" Casandra's voice sounded shaky and upset.

"No, Casandra, I cannot. They loved your father too," her mother responded curtly.

"If they really loved him, they wouldn't be able to laugh and tell jokes right now." John thought he heard Casandra's voice crack.

"Listen honey, I know this is hard, and everyone is finding their own way to grieve. Why don't you go up to your room for the rest of the evening? I'll make sure no one goes upstairs for the rest of the night, and you can have some time to yourself."

John glanced back toward the hallway and saw Casandra quietly make her way up the stairs in her simple black dress and Mary Janes. She shouldn't really be alone with all she drank, he thought to himself. He quietly excused himself to use the bathroom, though he wasn't really close enough to anyone for them to notice his absence. Once he got to the hallway, he looked around for any company and then took his leave up the stairs before anyone could see.

He took gentle steps down the upstairs hall until he heard the faint sound of crying. He listened for a moment to be sure and then walked into the room like he had no idea anyone was in there. Casandra gasped at his intrusion and quickly used a tissue to wipe at her tear-stained cheeks.

"Oh my god, I'm so sorry! I was trying to find a quiet space and...I didn't realize anyone was in here," John explained, feigning ignorance quite well he thought.

"It's, uh, ok I guess," Casandra replied, trying to gauge the situation in her inebriated state.

"No, really. I just couldn't take any more of their laughter and jokes right now but, I'll go find somewhere else to go," he moved toward the door, though he had no intention of leaving.

"You couldn't take the jokes either?" Casandra asked, then suddenly burst into tears again.

"Oh dear," John sat beside her on the bed and wrapped an arm around her shoulder. "I'm so sorry."

"I juss miss him so much," Casandra slurred slightly as the alcohol mixed with her grief.

"Me too, Casandra, me too." He stroked her shoulder with his thumb softly.

"You...you know my name?" Casandra almost hiccuped, and John felt his cock start to harden at the vulnerable sight of her.

"Of course Casandra. Your father talked about you all the time."

This caused new tears to spill over and she leaned into his shoulder for comfort. "I juss miss him so much..." she confessed again into the warmth of his shirt. There was no denying his arousal now as his cock strained against his dress slacks.

"I don't want to hurt anymore," she admitted.

"Is that why you were sneaking alcohol?" John asked with a hint of reproach in his voice.

"No! I mean, I wasn't...I mean..." a hiccup interrupted her abysmal attempt at lying.

"It's ok," John soothed her as he rubbed her arm and hugged her into his chest. "I know you just want the pain to go away."

"You won't tell my mom will you?"

"Casandra, you are safe with me. I just want you to feel good too," John smiled to himself. "Do you have any special memories of your dad? Any traditions you would keep?"

Casandra sniffled slightly and murmured, "he would always kiss me on my cheek before he left for work. No matter how big of a rush he was in, he never left without it..." her voice became thick again with emotion.

"Oh Casandra," John said gently. "Like this?"

He pulled away from her slightly and then leaned in and offered a soft peck on her cheek. She nodded her approval, and he did it once more. As he pulled away to look at her, he saw her eyes closing and her body swaying a bit. Obviously the alcohol was starting to effect her more.

"Do you want me to make you feel good?" He whispered in her ear.

"I don't want to hurt anymore," she mumbled without opening her eyes.

John kissed her cheek once, twice, and then began to let his lips travel across her face, leaving soft kisses everywhere they touched. When he reached her mouth, her lips responded slightly out of habit, but he watched her brow start to furrow in confusion.

"Don't worry Casandra. I'm going to make you feel better." With that last promise, he began to lean his body into hers as he kissed her neck. Her body went willingly into the bed, as the alcohol had weakened its strength and resolve. She mumbled something incoherent, which he took as encouragement, and he kissed his way down her sweet skin until he hit the neckline of her dress. He continued to press his lips against the thin black fabric as he slid down her body to where her knees met the edge of the mattress. Then he slowly slid her dress up her thighs, following his fingerprints with soft suckles, leaving goosebumps every place that he tasted.

"Please Mr...." Cassandra's quiet begging trailed off as she attempted to think of his name.

"Do you know who I am?" John asked curiously.

"Umm...no, I...I'm sorry...but..."

"Shhhh," John said against the lace of her undies. "It's ok. I'm the man who's gonna make you feel better."

"But..."

Before she had a chance to finish her protest, he licked her panties with his tongue flat. Her sudden intake of breath made her sound so innocent, so new to this. The very thought urged him on as he sucked on her sweet pussy through her now damp undies. His fingers played with the edges of the tiny fabric keeping him from tasting pure heaven. He began to suck and lick at her clit through the barrier, causing quiet moans to come from the nearly incoherent girl. Oh so gently, he slipped a finger into her panties and felt the growing wetness that met him there. That's the beauty of the body, he thought to himself, it doesn't need an alert mind to respond to what it wants.

And it was so apparent that her pussy wanted him, he determined as he slid his finger inside her and began to pump it in and out. Her moans increased somewhat and her body began to react to this pleasure. His sucking grew more insistent as he added another rough finger to her wet, inviting opening and even her mumbled "no, please" was contradicted by her legs spreading wider.

Oh yes. She wanted to feel better, whether she knew it or not, he thought as he curved his fingers upward toward her G-spot.

"Unnggghhh..." Casandra's sounds we're no longer controlled by logic, he could tell. Her pussy began to clench around his fingers and he knew she was almost there.

"Please...unnggghhh...not my dad's friend..." Tears streamed down her face as her breath quickened. Her body writhed against his hand as he fingerfucked her closer and closer to the edge. Suddenly he slipped his thumb into her panties and rubbed her clit as he coaxed her.

"Yes, Casandra, let me make you feel better..."

"Ohhhh my...oh my....I'm...oh god!" Casandra cried out as she came hard on John's hand. He quickly slipped his fingers out and lapped up her juices in ecstasy.

What began as cries of pleasure dissolved into sobs as she tried to grasp what had happened.

"Why? Why did you do that?"

"Oh baby, you said you wanted the pain to go away. I was just doing what you asked me to. But," he continued as he pulled down her panties, "if you're still crying then I haven't done enough for you yet."

"Wha--"

Before she could finish the question, he undid his slacks and pulled her closer to the edge of the bed by her knees. Then he spread her legs and placed his cockhead at her opening.

"I promised I would make you feel better, and I won't stop until you do."

With those words, John thrust into her tight little cunt in one move. The groan that erupted from him mixed with the cry that escaped her. He had never felt a pussy milk his cock like this, he thought as he thrust deeper and harder.

Casandra's sobs continued as she begged, "please stop the pain. Please..."

"Oh fuck Casandra, yes," John breathed heavily as he enjoyed going bareback in this sweet teenage pussy. He looked down to admire her lips enveloping his cock, and that's when he noticed the pink tinge to her juices as they coated his shaft.

A virgin?

"It hurts..." she moaned as she cried.

"Casandra, baby, fuck you're so perfect. I know it hurts now baby, but I'll fuck the pain away."

With that, John leaned over her and started drilling her harder. Tears slid down her cheeks as she arched her back to try to accommodate his rock hard cock as he fucked her. He pulled at the neckline of her dress to expose her pert, supple breasts. Fuck, they were gorgeous! He took her nipple in his mouth and started sucking it like a starving babe. He laughed at the irony that she was closer in age to a baby than he was and felt his cock twitch at the thought.

"Oh baby, you feel so good. You're so good at this."

"But I've never....oh, please stop...unngghh!" Casandra moaned involuntarily as he lifted her legs and began to hit her G-spot with every thrust. She didn't have to say it. John knew he was the first man to ever fuck that pure, innocent pussy of hers and even her cries of pain were bringing him closer and closer to exploding.

"Oh Casandra, you're so good, you're gonna make me come. Don't worry. It'll make you feel better to feel my hot cum inside you. Don't you wanna feel better?"

"Please...I just want the pain to go away...I want my daddy..."

"Oh Casandra, let me be your daddy right now." His body pressed down on hers as his lips met hers. For a moment she complied in her intoxicated state, and he dared to slip his tongue between her lips. This invasion cleared her mind just enough to turn her face away from his.

"No, please...I want my daddy...I want my daddy..."

Her begging for her daddy as he fucked her sweet pussy was more than John could take, but he refused to come alone. He began rubbing her clit again as he fucked her as deep as he could.

"Oh god! No...please...daddy...please...I'm gonna..." Her incoherent begging took them both over the edge, and John thrust deep inside her tiny hole as he came hard, spurting his hot semen all over her walls. Casandra's young body spasmed and convulsed as she came, milking his cock for every drop of spunk as she cried out.

Finally they both finished and John collapsed on top of his teenage dream. He kissed her passionately, even as she tried to turn away in her delirious state.

"Thank you Casandra, baby. I feel so good now. Don't you?"

Casandra responded only with silence as tears continued to stream down her cheeks. John stood up and pulled up his slacks. As he stared at her gorgeous, ravaged teenage body, he considered covering her up but couldn't bring himself to do it. Instead he took out his cell phone and captured a single picture before he quietly left the room.

As expected, no one even heard them over their drunken laughter downstairs. He slipped out the front door and headed home, without anyone noticing. If anyone asked the other guests, they would say he had left hours ago. They might even say he missed out on the best part of the evening. But John knew that nothing could compare to consoling Casandra.