A Fortunate Encounter

"Hey mister." Simon almost jumped in surprise at the voice. "Are you lost?"

Nervously, he turned around. There, only a few feet away, stood a young woman, head cocked to the side in curiosity.

Well, he thought woman, but she could just be a schoolgirl. Short, with long blonde twin tails and bright blue eyes, the girl wore a white button up shirt with a blue tie. Her short skirt ended mid-thigh, and she was wearing white thigh length socks. The very picture of a beautiful schoolgirl, but then in this district...

"You look a little lost." She continued, "People usually have a...reason to come here."

It was a Saturday afternoon. Why would a schoolgirl be out in uniform on a Saturday? Which meant...

"Ah, I though, er..." Simon mumbled, in the face of her open, cheerful expression, "I mean, I'd heard things about, well..."

"Ah, right!" She said brightly, "I thought that might be it. Most guys who come around here know what they are looking for, but we get some curious waifs too."

"Yes, well...I don't really know what I'm doing."

"I can see that." The blonde said with a girlish giggle, "But that's okay. Everyone starts somewhere. So, how about me?"

"You?" He stammered. Could it be that easy? The girl was stunning, no doubt, but it seemed too good to be true.

"Well, I did find you first!" She said, clutching her fist to her chest, "And I'm great with newbies."

"I...ah, how...how old are...?"

"Oh, silly, of course I'm old enough." The girl stepped closer, lightly punching his shoulder. She smelled of lilies, "I'm eighteen."

"And you...er, have...er..."

"Oh, don't you worry about that. I'm more than enough for you, sweetie." She giggled again, "So, how about it?"

"Ah...er, I mean..." Heart pounding, Simon stared at his feet to avoid the dazzling gaze of the young woman, "I think...I'd...I think I'd like that." He managed at last.

"Hurray!" The girl cheered, hugging him. Simon almost started hyperventilating at the feeling of her slim body pressed against him, "Come on, my apartment isn't far."

Completely out of his depth, Simon allowed himself to be led down the street. The girl - Abby - chatted endlessly, seemingly unperturbed by his inarticulate mumbling. It helped, somehow, to have her acting so comfortably with everything. She did say she was used to newbies.

As they walked, he couldn't help but steal glances as they went - she was so pretty and bright, it was so strange to find her in a place like this. Or for her to find him.

"Do you like my uniform?" She asked, catching his eye as he glanced her way once again.

"Ah!" Simon clammed up, feeling a blush forming.

"It's real you know. I'm in my last year now, but I'll probably keep it around. Guys seem to like it."

"It's...cute." He managed.

"Right?" She gave a small twirl, skirt briefly billowing out. It really did suit her; the tight shirt and tie emphasised her sizeable boobs, and clung in tightly around her narrow waist. The short skirt just framed the pale, perfectly smooth band of exposed thigh, highlighted further by the long, tight thigh highs clinging to her slender legs. "Aw, mister - you'll make me blush."

Realising he was staring, Simon snatched his eyes away, and Abby laughed cheerily.

"Here we are." Abby said after a few more minutes leading him along the quiet streets. She had stopped outside a modern looking apartment block, turning to face him. Behind forward slightly, she looked at him with a big smile.

"So, are you ready to have some fun?"

"Y-yes!" He almost barked.

"That's great!" She beckoned him forward, waving a pass at a detector by the door. He pushed it open to enter, and she followed behind. As he stepped inside, he felt her hand brush against his butt, squeezing gently.

He let out a small yelp, looking back over his shoulder. She met his gaze, eyes sparkling.

"Come on, it's on the third floor."

Palms sweating and heart pounding, Simon made his way upstairs through the brightly lit building, with Abby at his side still chatting away.

As they ascended the last flight up to the third floor they passed a tired looking young woman coming the other way, carrying a large black bin bag before her.

"Hi Cat." Abby said cheerily, waving.

"Oh, hey Abby." The young woman said wearily, blinking as though noticing them for the first time. Her eyes drifted to Simon, and a knowing expression formed. He cringed back involuntarily.

"Take it easy on him, Abby. He looks terrified."

Abby blew a raspberry at the other woman.

"We'll be fine, shoo." She said.

Cat shrugged.

"Well, you know best I suppose. Have fun kids."

Abby waved him onwards as Cat continued on her way. A short distance down the next hallway she waved her pass again and nudged open the apartment door. He followed her in, stopping just inside as he heard the door closing behind him.

This was it. He was here, finally, after so long just thinking about it. It was terrifying.

"Hey, turn around."

Quivering, he did as she asked.

Sighing softly, Abby stepped in close and wrapped her arms around him, resting her head against his chest. After a moment, tentatively, he put his own arms around her.

"You're here now, mister." She said quietly, "Don't you worry about a thing, I'm going to lead you through everything."

"R-really?"

"Of course!" Abby squeezed him tighter, one hand drifting down to cup his butt, "I said I'm good with newbies. You just need to relax and let me make your dreams come true."

"That...that sounds good." He managed.

"It is good." Abby said enthusiastically, squeezing him tighter. "So, I know you've never been with a girl like me before, but have you ever...well..."

"I...no..." He said, embarrassment welling up again.

"Oh wow, I love being a guy's first ever." Abby said enthusiastically, "I'm super excited now."

Taking his hand. Abby led him through the clean, modern looking apartment and into the bedroom. The room was large and spacious, dominated by an opulent looking king sized bed.

Turning around, Abby grinned up him, her pretty face dazzling once again. Blushing, Simon stared down for a moment, before his notice was taken by something else.

Below, her blue school skirt, previously resting against her pristine thighs, was bulging outwards dramatically. His eyes widened in astonishment.

"I said I was excited." Abby said softly.

Her...he could barely bring himself to think the word aloud in his own head. He had known; of course he had known. That's why he'd come to the district in the first place.

But he'd never expected it to be so...so much.

"Is this what you wanted?" Abby asked, her confident smile betraying the fact that she already knew his answer.

Struck dumb, Simon could only nod, his mouth dry.

"Don't worry. I know I'm a big girl, but that's why it's going to feel so good." Abby stepped forward and grabbed his collar, pulling him down into a kiss.

Like with everything else, Simon had almost no experience with kissing, and he was completely unprepared. Abby's lips moved firmly and forcefully against his, her tongue prodding for admittance almost immediately. He responded as well as he could, kissing back to the best of his abilities, but it was clear she was dominating proceedings. More distractingly, he could now feel her large manhood pressing firmly into his thigh.

As she kissed, Abby looped one arm around his neck, tousling her hand in his short hair, while the other reached around to grab at his ass. At the same time, she began to rock against him, grinding her stiff length between them. Overwhelmed and at a loss, he allowed his arms to settle loosely around her slender shoulders.

"Can you feel me?" She breathed, breaking the kiss for a moment, "You've got me really hard."

Before he could respond, she pounced to kiss him again, and he could only whimper into it, his knees going weak. Adjusting her stance slightly, she started driving her cock between his legs, the astonishing length allowing her rub along the underside of his own crotch despite the difference in height. Feeling her powerful member thrusting against his own thoroughly average effort was both emasculating and incredibly arousing all at the same time. Abby's lips moved forcefully against his, and her tongue wrestled his into submission. Simon felt completely overwhelmed, assaulted from all angles in ways he had never experienced before, and when Abby's hand slipped into his jeans, one languid finger poking at his core, he broke.

With a surprised groan, he felt his knees buckle, and he slumped to the floor. Breathing heavily, he put a hand to his forehead, trying to recover his senses.

"Oh my," Abby said, a teasing note in her voice, "you are keen."

Simon raised his eyes, but got no further than her crotch. Just inches from his face, jutting out proudly, was Abby's erection.

Her skirt, which had previously been bulging out, was now reduced to mere drapery, unable to cover up her full length. It jutted out perpendicular to her body, long and smooth with an intimidating thickness. Her head was just inches from him, a glistening bead of pre-cum forming at the tip. With her skirt held up, he could see her smooth, heavy balls nestled between silken thighs.

As he stared, Abby started shaking her hips slightly, and her cock bobbed before him in response. It was almost hypnotic, the way the pale, hard flesh swayed back and forth.

"Do you want a taste?" Abby said in a sing song voice.

Finally managing to tear his eyes away, Simon looked up at her, unable to speak. It was all so overwhelming. She looked down at him, a curious, gentle smile on her face. He wondered how many other men she had looked down on like this over the years.

"Do you want to suck my cock?" She said with a gentle tone belying the rawness of her words.

Mouth dry, Simon nodded up at her.

"Well then," Abby grinned, "let's have some fun. Open wide."

With that, the girl edged forward, her huge dick poking towards him. Taking a breath, Simon leaned forward to meet her, pressing his pursed lips to her tip.

"Aw, that's sweet." Abby said, and Simon blushed. He'd just kissed her dick - what kind of tool did that? "But why don't you taste me too."

He felt her hands rest gently on his head, and then suddenly she was pressing forwards against him. Surprised, he opened his mouth, her thickness forcing him to open as wide as he could.

He had a dick in his mouth. After so many fantasies over so many years he was finally there, knelt before a beautiful girl with her huge dick in his mouth.

His own cock had never been harder.

Trembling, he brought a hand up to touch her shaft. Her cock was smooth and warm, with an iron like hardness just below the surface. He could barely grip all the way around, such was her girth.

Sucking gently, he savoured her taste, running his tongue around her head and probing at tip, hoping for another salty bead of her flavour.

"That's it." Abby said softly, "Why don't you stroke me, too?"

Happy to be instructed, Simon started to run his hand along her length, squeezing experimentally as he did so. Her hard cock twitched in response, and she sighed approvingly.

"That's good, keep that up."

Wanting to please, Simon began sucking with more vigour, massaging her head with his tongue has he did so. He stroked her enthusiastically, marvelling at how he could pump her huge cock while still sucking her.

"Mhmmm." Abby murmured happily, "Are you sure this is your first time?"

Unable to withdraw, Abby's hands holding him in place, Simon looked up to try and meet her eyes, nodding as well as he could manage.

She held his gaze as he worked her, smiling warmly down at him. She was so young and beautiful, like the prettiest girls he had gone to school with; girls who had never even known he existed. But she knew, and he wanted to do everything he could to make her pleased with him.

He didn't know how long he sucked, but his jaw started aching from the effort to accommodate her, and his pace started to slow. He wanted to withdraw, catch his breath, but Abby still held him in place. As though sensing his weariness, she began to slowly gyrate her hips, nudging herself deeper inside him.

"Just relax." She said gently, noticing his alarmed expression, "Open wide and I'll do the work." She giggled, one hand stroking his cheek, "I'm going to face-fuck you a little, okay? You'll gag a bit; just tap my leg if it gets too much for you."

Excited and scared all in one, Simon opened his mouth wide around her, moving to grip Abby's waist.

"Here we go."

He felt her grip his head a little tighter, and then suddenly push forward, her thick cock probing the back of his mouth and throat. Simon gagged immediately, coughing and gasping around her length even as she pulled back. Unperturbed, she thrust again, holding him firmly in place.

Desperate to please, Simon didn't protest, and Abby quickly built up a rhythm, panting softly with each thrust. His eyes watered, and he could only look up at her with blurred vision as she fucked his mouth. In felt like she was filling him up each time, but so much of her never even passed his lips and he knew she was taking it easy.

"You're doing so well." Abby said encouragingly, and Simon felt a surge of pride. "We'll have you deep throating in no time."

Eventually, her thrusts probed just a little too deep, and his gag almost turned into a retch. Tapping her leg urgently, he backed away, gasping for air as she withdrew.

With a few deep breathes, Simon rubbed the tears from his eyes, before looking back up at Abby. She had taken a few steps back, her magnificent cock glistening with his saliva, jutting out proudly from beneath her skirt. She watched him with concern, but grinned when he met her eye.

"So," she said, "how do you like sucking cock?"

"That was...intense." He managed.

"Not many boys are able to take me that well on the first go." She said, offering a hand to help him up, "It's just practice. Come see me often enough, and we'll have you taking the whole thing."

Smiling weakly, Simon allowed himself to be drawn close to her, and she pulled him down into another deep kiss. Once more he could feel her hard cock, and she ground her hips against him even her tongue invaded his mouth. Her hands roamed across his back, before descending to his waist, tugging at and eventually releasing his belt. Deft fingers popped open his jeans, and in moments they were piled around his ankles. Abby's dick rested heavily against his thigh, the saliva slickened flesh sliding against his now exposed skin.

Without warning, she shoved him hard in the chest, and he staggered backwards, jeans tangling around his ankles. The backs of his legs hit the bed and he toppled over. Just as he gathered his bearings Abby was there once more, standing over him, biting her bottom lip.

"I love the sight of a cute boy in my bed," she said softly, "waiting for me to take his innocence."

Simon swallowed hard, propping himself up on his elbows as Abby dropped to her knees. A moment later, having tossed aside his shoes and jeans, she looked up at him, grinning wickedly.

"Why don't you shuffle back a bit?" She said.

Nodding, anxious to please, Simon did so, and Abby crawled onto the bed after him. Nudging his legs apart, she moved forward to kneel over him.

"Let's get rid of that shirt, too."

Abby reached out to start unbuttoning him, and Simon moved to help, his fingers fumbling the buttons hopelessly. She met him in the middle, and he sat up a little to shrug it off. Abby took it from it, tossing it onto the floor behind her.

"Well now." She smiled down at him, "That's better."

He couldn't help but stare once again, taking her in as she looked down at him. She was still fully clothed, her standard uniform transformed into a sexy outfit by her raw sexuality. His eyes drifted down, across her stunning curves, before settling once more on her crotch.

In this position, with him now naked, her rock hard cock loomed imposingly over his own. He was by no means tiny, but hers was half as long again, and almost twice the girth. His semi-hard dick lay against his belly, as though cowering in fear of the monster that reared above it.

"It's cute." Abby had followed his gaze, and was now smiling once more.

"I'm not sure how I feel about that." He grumbled.

Abby laughed.

"Don't worry, don't worry. It's a lovely dick - above average, if it helps." She grinned, "I've been with much smaller guys before, but it's not like it really makes much difference."

Of course not, when she was packing near enough ten inches. Not many guys would be able to top her.

"I guess not." He managed.

With a happy nod, Abby collapsed forward into him, toppling them both back onto the bed with a pomf. Wrapping her arms around him, she kissed him enthusiastically, her small tongue lapping at him once more.

It felt amazing. Her soft lips working against his, her tongue invading his mouth, bringing with it the faint taste of mint, her full breasts mashing against his chest while her hands ran ribbons of heat up down his side. But, most of all, the jolts of pleasure that ran through him each time she ground her hips against him, crushing her heavy dick against his.

"You like that?" She whispered into his ear, breaking their kiss, "Just feel how hard I am. How thick I am." For emphasis, she pressed tightly against him, squeezing his dick again with her own.

"Oh god, yes." He moaned, "It feels like you're massaging me."

"I know, right? A massage with my dick." Abby chuckled, kissing at his neck, "There's a much better place I can do that, though."

Simon didn't respond, simply burying his face in her silken hair, breathing deeply in the soft scent; another touch of feminine perfection to offset her ultimate symbol of masculinity. He revelled in the moment, allowing his hands to roam her back, her pert behind, those impossibly smooth thighs. The joy of holding a woman in his arms, something so rare in his life, all the while delighting in her multi-pronged assault against him.

"So, what happens next?" Abby said, so softly it took him a moment to register it.

"W-what?" He managed.

"What happens next?" She repeated, "What does the strapping young man in my bed want to do?"

He let out a gasp as she pinned his cock with her own, grinding it slowly.

"I...I want..." he stuttered nervously, "I want you to choose. To...to show me."

"Mhmm, do you know what I want? What I really want to do?" Abby said softly, "I want to fuck you, Simon. I want to break in that tight little virgin ass, and fill you to the brim. I want to drill you until you squeal and cry out my name. I want you to feel my cum deep inside you. That's what I want to do." She kissed his neck again, "Is that what you want?"

"Abby..." He managed.

"I thought so." Abby said, happily.

Pushing back up to her knees again, Abby grinned down at him. She looked a little dishevelled now, her twin tail frazzled where he had been nuzzling and her shirt rumpled.

Reaching into a pocket of her skirt, Abby pulled out a sachet and tore one end. Seeing his confusion, she held the packet it out to him.

"Lube." She said cheerfully, "Never leave home without it."

"Oh...right."

Abby quickly squeezed a large dollop of the clear liquid on her cock, one hand running up and down the length as she poured. The faint squelching sound the lube made as she spread it upon herself was strangely erotic.

Once satisfied, she turned her attention to him.

"Lift your legs a little." She urged, guiding one up with her hand. Eager to please, Simon did as he was asked, acutely aware of how expose he now was.

"What a cute little pucker." Abby said, cocking her head. Simon let out a small gasp as she poured more of the lube directly on to him. "This is going to be a tight squeeze, I think. I can't wait."