Chloe’s Initiation

Tony placed his key in the slot and unlocked the main door of the apartment building he had called home for the past five years. He checked his mailbox and pulled out the usual assortment of bills and junk mail. Doing a quick sort, he deposited the junk mail into a recycling bin next to the mailboxes and shuffled through the remaining mail on his way over to the elevator.

The elevator doors opened as he crossed the lobby and a pretty young girl stepped out. Chloe from across the hall. Her long brown hair shone and her green eyes sparkled as she smiled at him, holding the doors open.

“Hi, Tony!” she said as he approached.

She was fifteen, with a set of tits that he was sure swelled a little more each day. He silently chided himself for thinking that way about his neighbor’s kid. But the truth was, she wasn’t really a kid anymore and was very quickly becoming a beautiful young woman. They had moved in about a year after he had. Her father had run off when she was only a baby, leaving her mother, Catherine, to raise her alone. Catherine worked nights and Tony, who had taken an instant liking to the precocious eleven year old, volunteered to look after Chloe while she was at work. He was a freelance writer so his schedule was somewhat flexible. Besides, she was a great kid; very smart and she somehow seemed impressed that he was a writer. That all stopped when she turned fourteen and was old enough to look after herself. But they remained close and he almost thought of her as a niece, or at least a close friend.

Catherine was also quite a looker. She was thirty-five, only five years older than he was, but looked much younger. She had the same green eyes and long, wavy hair as her daughter and a very pretty oval shaped face with high cheekbones and thick, pouty lips. He often lay awake at night masturbating and imagining those luscious lips engulfing his cock. Unfortunately, it soon became clear that she only thought of him as a friend and neighbor.

‘Oh, well,’ he’d thought to himself. ‘Plenty of other pretty women out there. And they don’t live right across the hall.’ That could complicate things. Maybe it was a blessing in disguise that she didn’t seem attracted to him.

Realizing he hadn’t yet greeted Chloe, he returned her smile. “Hi, Chloe. Thanks.”

She gave him a quick salute, still grinning. “No problem!” She turned to go and Tony found his eyes drifting involuntarily to her cute ass inside her tight jeans. Suddenly, she stopped and turned, causing him to quickly avert his eyes.

“Oh, I meant to ask . . . are you going to be home tonight?” She didn’t appear to notice his roving eyes. He paused, taken by surprise at her question. It wasn’t like she never came to visit, but lately she hadn’t been over as much. Teenagers had much more important things to do with their time than sit around with their thirty year old neighbors, he had assumed.

“Uh, yeah, I think so,” he replied, looking up at her from his mail. “Why?”

“Would it be ok if I came over . . . say around seven? I have an essay due next week and I could use some professional help.” She flashed him a broad smile.

He nodded. “Sure, come on over.”
“Great!” she said as the doors began to close. “See you later!” She turned and he got one more brief glimpse of her ass before the doors slid shut.

‘Tony,’ he told himself, ‘you behave yourself!’ He chuckled as the elevator stopped at the fifth floor and he walked down the hall to his apartment, the image of the pretty teenager still fresh in his mind.

Chapter 2

The dishes were drying on the rack and Tony was flopped on the couch watching some mindless sitcom on TV. He’d finished his column for the paper before supper and had e-mailed it off. He should be working, though. Like most writers, he had a book partially written and it wasn’t going to finish itself. He glanced at his watch. Six-thirty. Chloe would be here soon, anyway. No point in working on it now.

He was somewhat troubled by the impure thoughts he had been having ever since he spoke to her earlier. She was only fifteen, for gods sake! A kid! He flipped through the channels, hoping to find something that would take his mind off of her. He finally settled on a documentary about World War II on the History Channel. He was still watching it half an hour later when there was a quick knock at the door and Chloe came in, closing the door behind her. She went over to the kitchen counter and dropped a few books onto it.

“Hey, there. Mind if I borrow a Coke?” she asked, opening the fridge and peering inside.

“Help yourself,” he replied, turning off the TV. He got up and went into the kitchen, where her cute little ass was sticking out of the refrigerator. “Find one?” he asked, playfully slapping her butt.

“Hey!” she exclaimed, straightening up with a can of Coke in her small hand and a bemused look on her face. “I was just seeing if you had anything to eat! I got the munchies!”

He opened a cupboard and tossed her a big bag of chips, which she managed to catch against her perky tits. “Will those do?” he asked and reached around her to get a beer from the fridge for himself.

“Uh-huh,” she replied, opening the bag and stuffing some into her mouth. “Thanks,” she mumbled as she made her way into the living room. She dropped to the couch and turned on the TV. “The History Channel again!” she exclaimed, rolling her eyes. “Man, you need to join the modern world!”

He sat down next to her and grabbed a handful of chips. “Those who don’t remember the past are doomed to repeat it,” he said. She arched an eyebrow in a way that he thought made her appear much older and he added, “or something like that. I’m paraphrasing.”

She munched on some chips and turned back to the TV, flipping through the channels.

“Whatever,” she said absently, as only a teenager can do. She stopped on the Fashion Channel, where a scantily clad model was showing off the latest swim wear.

“I’d love to have one of those,” she said. The white thong bikini was so small it left very little to the imagination.

“Very nice,” he commented. “But I think your Mom may object.”

She shrugged, then turned to him. “But don’t you think I’d look good in one?”

Uh-oh. A picture of the young girl next to him in a skimpy bikini suddenly filled his mind. She would look good in one. She really would. She may be only fifteen, but she was developed to the point where she could pass for seventeen or eighteen, or even older with the right makeup.

“Well?” she asked, a note of impatience in her voice. He realized that he had been staring at her.

“Well what?” he asked, trying to bring himself back into focus. He turned back to the TV and watched another too-skinny model strutting along the runway.

“Don’t you think I’d look good in a thong bikini?”

He sighed. There was really no right answer. “Sure, I guess,” he finally replied, still staring at the TV.

“Really?” She was watching him closely.

He turned to her, a hint of irritation in his voice. “I said yes, didn’t I?”

“Ok, ok,” she said sullenly, turning back to the TV. “I was just asking.”

They sat in silence for a moment or two, absently staring at the images on the TV, until Chloe said quietly, “Have you had many girlfriends?”

He shrugged, wondering where she was going with this line of questioning. “A few, I guess. Why do you ask?” Was she trying to set him up with her mother?

She leaned back and took a sip of her Coke before answering. “We’ve been learning about sex at school. I was just wondering what it was like.” She continued to stare at the TV, not looking in his direction.

He stared at her. “What do you mean, ‘what it’s really like’? Isn’t that what they teach you?”

She placed the nearly empty bag of chips on the coffee table. “Well, yeah, sort of. I mean, they tell us how it’s done . . . how babies are made.” She glanced over at him. “But it’s all so . . . boring.” She scrunched up her face. “And even a little gross.”

Tony chuckled, remembering the clinical films and texts from his own sex ed class. He supposed it probably hadn’t changed that much over the years. “Yeah, I guess they can make it seem pretty boring.” He found it difficult to meet her eyes.

“So it’s not really like that?”

He squirmed uncomfortably. “Well, yes and no. It’s . . .” He stopped, eyeing her suspiciously. “Shouldn’t you be asking your mother about this?”

A look of horror came over her face. “Are you kidding!? I could never ask Mom about sex! She’d think I was planning to screw every boy at school and I’d never be allowed out of my room!”
He gave a short laugh. “I don’t think she’d be that bad!” He paused, his mood growing more serious. “But she has good reason to worry. You are becoming a very beautiful young woman. The guys are soon going to be chasing after you relentlessly.”

She looked at him, her green eyes sparkling and a smile forming on her lips. “You think I’m beautiful?” Her face blushed slightly and she looked so cute. So innocent. Oh, shit.

Realizing he was cornered, he knew he had to say something. “Well, of course. You must hear that all the time.” He looked back at the TV, pretending to find the shampoo commercial interesting. She didn’t reply, but turned back to the TV. The commercials ended and more models prowled the runway in haute couture fashion. Weird shit. ‘Guess I just don’t get high fashion,’ he thought, trying to get his mind off the sexy teen sitting beside him. It wasn’t working.
Suddenly, Chloe picked up the remote, turned the TV off, and stood up in front of him. Her jeans were tight enough that her graceful curves were well defined and her t-shirt was the type that showed off a portion of her bare naval. His eyes moved up to her face, not failing to notice the tiny bumps of her hard nipples under her t-shirt.

“You really think I’m beautiful?” she asked in a timid voice, taking his hand. Tony swallowed, unable to think of anything appropriate to say. The truth was, he wasn’t sure he wanted to say the appropriate thing right now. She raised his hand to her breast and pressed it to the soft flesh, all the while chewing nervously on her lower lip. “Do you think I’m sexy, too?” she asked, her voice almost a whisper.

Tony suddenly realized what was happening. His expression changed and he quickly pulled his hand from the soft, pliable flesh of her young breast. “Chloe! No, no! Absolutely not!” he exclaimed, shaking his head. “Whatever made you think I’d do that!?”

She moved a little closer. He could sense her trepidation, but she didn’t back down. “I’ve noticed how you look at me when you think I’m not looking.” He swallowed hard and felt his face getting warmer. “And it’s ok. I don’t mind.” She managed a nervous smile. “Actually, I kind of like it.”

“It’s wrong,” he muttered, shaking his head and staring down at his clenched hands.

Her hands were moving over her torso and across her curved hips. “Why? Why is it so wrong?” she asked. “You do think I’m sexy, don’t you?”

“Yes! No! I mean . . . aw, hell!” He took a deep breath and looked up at her. “Chloe, you’re only fifteen.”

“I’ll be sixteen next month,” she replied defiantly, her hands still caressing her firm young body. She certainly wasn’t making this easy!

He ignored that comment. “You’re fifteen. And I’m thirty. That’s why.”

She took another step closer and moved one of her long, slender legs between his knees. “So what? I find you very attractive. You don’t even look thirty.” She was moving her leg seductively against his inner thigh and her teenaged pussy was only inches from his face, leaving him at a loss for words. “And I did some checking. The age of consent here is fourteen, so I’m not jailbait.”

He pushed her back, stood up, and quickly walked over to the kitchen, afraid that she might notice his hardening cock if she got any closer. He leaned against the counter that divided the two rooms and looked over at her, willing his cock to go down. It wasn’t working. Just the opposite, in fact. She stood where he had left her, looking very cute, very sexy, and still very young and innocent, dammit!

“Look, Chloe, you’re very beautiful and I’d be lying if I said I wasn’t tempted. But legal or not, it would just be wrong!”

She sighed and slowly walked over until she stood at the opposite side of the counter, facing him over it. “Tony, I’ve decided that I’m ready and that I’m going to have sex. Soon.” She paused for effect, searching his eyes, then continued. “I could easily find a boy at school or in the neighborhood, but he would be as inexperienced as I am. I’d rather do it with someone I know and trust. I’ve heard you telling Mom that you’ve had a vasectomy, so I can’t get pregnant. And we wouldn’t have to worry about diseases. I know how careful you are.” He silently cursed himself for admitting to her once that he always used a condom unless both he and his partner had been recently tested, trying to impress upon the budding teen the importance of safe sex. It was becoming obvious that she had been giving this some serious thought.

He stared back into her hypnotizing green eyes. She made a good point. Oh, shit! Now he was starting to think with the wrong head! He sighed and looked down at the counter for a long moment before looking back up at her.
“If, and I do mean ‘if’, I agree to this, you have to promise to tell no one. And I mean no one. Not your friends; not in chat-rooms; no one! Understand?”

She nodded, a smile forming on her lips as she felt him giving in. “I promise, Tony,” she said softly, placing her small hand over his. He studied her face until he was satisfied she was telling the truth, then let out a long breath.

“If I say yes, when would you want to do it?”

Her smile widened and her eyes sparkled. “Right now. Tonight. My Mom’s away until Sunday.” Tony remembered Catherine mentioning that earlier in the week. She had asked him to keep an eye on Chloe while she was away. Today was Friday.

“I see,” he replied, feeling his cock twitch. “And what exactly did you want me to teach you?”
She gave him a puzzled look. “I want you to teach me how to . . . have sex,” she said with a shrug.

“Yes, but what kind of sex?”

This caught her off-guard. “There are different kinds?”

He nodded. His cock was now straining at his jeans and he was glad he had the counter to hide behind. “There are many different ways to have sex. There’s intercourse – screwing, fucking – whatever you want to call it.” She nodded, listening intently. “Then there’s oral sex,” he continued, “blow-jobs, cunnilingus.” She nodded again.

“I’ve heard girls at school talking about blow-jobs. They don’t seem to like it that much.”
He shrugged. “Some girls do, some don’t. You won’t know until you try.”

“What’s cunni . . . cunnil . . .”

“Cunnilingus. That’s when a man does oral sex on a woman. Just about every girl likes that.” He grinned and she blushed a little.

“Is that all?” she asked.

“That’s the basics,” he replied. “There are many different positions, different ways to give oral, but most are easier to demonstrate than to explain.” She gripped both of his hands in hers and met his eyes with a pleading look.

“So you’ll do it, then?”

He sighed deeply and looked at the pretty young virgin who was practically begging him to fuck her. “Maybe. Just how much do you want to learn?” He was hooked, and she knew it. She grinned mischievously.

“Everything. I want to learn everything!”

He looked into her eyes for a long moment then nodded resignedly. “Ok, then. Just remember your promise. Tell no one.”

She ran around the counter and embraced him, her firm body pressing against the hardness in his jeans. “Thank you, Tony!”

Despite his reservations, he returned her embrace. “Don’t thank me yet. I’m still not convinced that this is a good idea. In fact, I know it isn’t!” She released him and stood back, some of her enthusiasm waning. He took her hands, his voice softening. “And one other thing. The first time, there will be some pain. It may only be a little pinch, or it may really hurt. It’s normal. It happens to every girl. I just wanted you to know.”
She smiled at him. “I knew that, but thank you for being honest.”

He slowly took in her tight body, knowing that she was now his for the taking, for better or worse. “Ok. Shall we get started?”

She bit her lip and nodded nervously.

Chapter 3

Tony took Chloe by the hand and pulled her to him. He noticed that for the first time, she was trembling. Reality of what they were about to do had set in. He raised her tiny hand to his lips. “Are you absolutely sure you want to do this?” he asked, giving her one more chance to back out. “Because it’s not something you can undo.”

She paused before answering and he thought for a minute that she was going to change her mind. “Yes, I’m sure,” she finally said, looking into his soft brown eyes. “I’m just a little scared.”

He took her hand and led her over to the couch where they sat down, his cock leaving a prominent bulge in his jeans. He pulled her face to his and their lips met. He probed at her lips with his tongue and she immediately parted them, inviting him in, her tongue meeting his. She was actually a pretty good kisser.

After a moment, they pulled apart and he smiled at her. “You’ve french-kissed before.”
She grinned bashfully. “Only twice. But I like it.”

“What else have you done before? Have you ever given a boy a hand-job?” She shook her head.
“Have you ever seen a real cock?” Again, she shook her head, seeming embarrassed. He smiled and stroked her luxuriant hair. “That’s ok, honey. I just need to know how much experience you’ve had.”

She smiled at his use of a pet name. It felt nice, like he was her boyfriend. “So what’s next? Do we kiss some more?”

“Later. Right now we have to get undressed.”

This seemed to lessen her enthusiasm somewhat. “Oh . . . ok.” Her hands went to the hem of her t-shirt and, after a brief hesitation, she slowly lifted it over her head, pulling it free from her long hair. She was wearing a white lace bra under it that she seemed to have outgrown. Her tits were straining at the thin fabric.

“Now take off my shirt,” Tony said. He was wearing a white cotton buttoned shirt and Chloe’s hands trembled as she undid the buttons. When she finally finished, she pushed it from his shoulders, revealing his bare, toned chest and arms. He was no body builder, but he was comfortable enough with his body to go shirtless at the beach, often receiving lusty looks from female beach goers. “Touch me,” he said. “Rub your hands over my skin.” She reached up and did as he instructed, her small hands gently caressing his chest.

After a moment, he said, “Ok, now stand up.” She stood up in front of him and he undid the button of her pants. As he lowered the fly and began to wriggle the tight jeans over her curvaceous hips, she looked down at him.

“Shouldn’t we turn off the lights?”

He met her eyes and smiled as the jeans slid lower, revealing her white cotton panties. “No, definitely not. Down, maybe, but never off.” He slid the jeans down her long, slender legs and she stepped out of them. He detected a musky aroma and noticed a damp spot on her panties. He explained about the lights. “If you turn the lights off, you can’t fully appreciate your lover’s body or see their face. That’s very important. It’s also important for you to tell me what you like or dislike. Understand?” She nodded, looking very much like the little girl that she was, standing there in her little girl underwear. For the hundredth time, Tony wondered what the hell he was doing. Then the scent of her sex reached him and he once again switched operational control over to the other head.

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