Hunter’s love for Futa

Chapter 383: A Fortunate Encounter by PenguinEmperor



"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." 

With one finger, Abby began to massage to cool liquid into him, and he yelped as she slipped it inside. She grinned at him, working her finger in and out steadily.

"You're super tight - have you ever had anything up here before?"

"No..." Simon shook his head.

"Well, we're going naught to one hundred today then." Abby laughed, "I think that should do it."

Withdrawing her finger, Abby shuffled forward again, urging his legs wider with her thighs. Simon swallowed hard as her dick came up against him, and she slowly started running her head between his ass cheeks.

"Are you ready?"

Nervously, he nodded.

"Okay then. Try to relax." Smiling encouragingly, she glanced down to where her hand guided her prick to line up with his hole. After a moment, he felt it nestling there, its thickness parting his cheeks and pressing gently against his core.

Then, Abby began to push.

"Ugh." Simon grunted, surprised at the pressure she was able to bring, and a moment later he felt something give. "Argh!"

It had only taken a few seconds and her head was inside. She was so impossibly hard, her cock was not going to be denied for a moment. His ass cried out in protest at the invasion, pain coursing out from his stretched out ring. She was so big; he wasn't prepared at all.

"Shh, it's okay baby." Abby said softly, reaching out one hand to stoke his cheek, "Just breathe and relax. This is the worst bit, just hold on for me and it'll ease off."

Staring up into her eyes, Simon nodded. He trusted her; he just needed to get used to it. Surely.

"It's okay." She said again, and now Simon felt a little comforted, "God, you are so tight. I haven't fucked a guy this tight in a long time."

Breathing slowly, Simon clenched and released his grip in the bedsheets, trying to relax himself. Looking up at Abby helped. Her encouraging expression, her warm eyes, the gentle caress of her fingers against his cheek all help to calm him. She was calm. She knew what she was doing.

Slowly, the pain began to subside, and Simon felt himself relaxing a little, a tension he hadn't even noticed draining away from him. Abby seemed to notice to, and her smile widened.

"See?" She said, "Now we can start having fun."

Simon swallowed nervously, and nodded.

"Okay! Now remember to try and relax." Abby said cheerily, and started pressing her hips forward.

The pain began to return once more, and he let out a low hiss, but it was not so sharp.

"Abby." He groaned.

"Shh, it's okay baby." She said, encouragingly, "Just breathe and relax. You're doing well. So well."

"It stings."

"I know baby, I know, but it'll pass." Shifting slightly, Abby nudged his knees outwards so that she was fully between them, all the while pressing forward, "Just a little more."

Lying on his back as he was, looking down was awkward, but he shifted up on his elbows slightly. Looking past his own flaccid member, he could see a length of her thick shaft still exposed.

"Are you peeking?" Abby said, and suddenly she lurched forward. Simon collapsed backwards, groaning as a sense of fullness overcame him. The throbbing pain was balanced out by the new sensation, a strange and alien feeling deep within him.

"Oh god." He mumbled.

"Mhmm, you're squeezing my cock so tightly, baby. Like you never want to let me go." She let out a long sigh, and then collapsed forward suddenly, burying herself inside him.

"Aargh!" Simon groaned as he felt her slender hips pressed him, and her heavy balls slap up against his ass.

He was totally filled, and for a moment he could hardly breathe. She was completely inside him, her huge cock occupying every nook and cranny of his ass, pressing and squeezing against him every which way. Something inside him sang with an alien sensation, while other parts cried out in fruitless protest.

He was hers, as completely as a man could be. Even more than the pain, the fullness, the strange tingling, it was the sense of emasculation that struck him. He was being fucked. An eighteen year old girl, so small and feminine, yet twice the man he could ever be, was fucking him.

Having flopped against him, Simon could feel Abby's full breasts, still constrained by her school shirt, mashed up against his chest. Blinking to clear the stars that swam across his vision, he blearily looked down to meet her gaze.

"How do you like it, Simon?" She said, softly, "How do you like ten inches of schoolgirl cock right up your asshole?"

"I...I..." he started to mumble.

"You're such a good little boy, Simon." Abby said, "My cute little bitch. So happy to take my big, manly dick. Do you love it, Simon? Do you love my big fat cock?"

As if to emphasise her words, Abby slowly ground her hips against him, and he let out a gasp.

"What was that?" She said cheerfully.

"I..."

"Tell me how much you love it, Simon." She said, smiling, "Tell me and I'll reward you."

"I...I love it." He gasped, looking up into her eyes, "Please...you're so big, Abby."

With a happy squeak, Abby leant forward and kissed him softly. His eyes fluttered closed as her velvet lips moved against his, her tongue brushing briefly against his. Despite the awkward position and the bewildering sensations echoing out from his core, he couldn't help but relax in her arms.

Then, without warning or any break in the kiss, he felt her start to draw back. The withdrawal of her huge pole seemed to suck at his insides as the thickness tugged and nudged at him as it went.

Then, just as unceremoniously, she thrust back in again, her hips and balls tapping firmly against him.

Simon let out a half howl, half groan even as she continued to kiss him. His ass exploded in sensation; the fullness, the throbbing stretch of his insides, the siren song of his prostate as her thick meat squeezed and bumped along past it. It was too much; he was losing his mind.

In moments, Abby started working up a rhythm of steady, shallow thrusts into him. His gasps and moans were muffled by her determined kiss, but the slap of flesh on flesh echoed clearly around the room. Again he clawed at the sheets, his toes curling almost painfully.

Maybe growing tired of his inability to respond, Abby broke off her kiss and drew back slightly, never breaking motion. She looked a little flushed, but otherwise serene.

"God, you're so tight." She said huskily, giving him a wolfish grin, "It's like you're trying to squeeze the cum right out me."

"Abby." He breathed, "It's...aaah."

"Feels good, right?" She said, glancing down. "Looks like your little man agrees."

Blearily, he followed her gaze down. True enough, cowering before her strong, thrusting hips, he had become hard. Each time she drove into him he felt a throb below the base, and his dick twitched uselessly.

"I think we're warmed up now. Let's take it up a notch."

Without waiting for a reply, Abby knelt up straighter, grabbing him by the waist. With a happy sigh she pulled back - on and on, more and more of her impossible length dragging free - until he felt almost empty, only to skewer him once more.

"Aaaaah." He gasped, his eyes rolling back as his insides exploded in outcry and exaltation once again.

"Oh that's so sweet." Abby said, "You're a cock slut already. I'm so happy."

She drove into him with long, hard thrusts now, and his whole body jolted each time. He moaned and squealed as she pounded him, each gasping cry as good as forced from him by her powerful length.

"That's it, baby." She said, sounding slightly breathy herself, "Moan for me. Are you gonna cum for me?"

At her words, Simon suddenly realised just how close he was. The thrumming cocktail of pleasure and pain within him was swirling and building with each thrust, and he was painfully erect, his cock flopping between them.

"I'm..." he breathed, "I'm close."

"Like a true bottom boy. How perfect." Abby sang, "I'm close too. Let's cum together. I'll fill you up with all my love."

Despite everything, despite the ferocity with which she was fucking him, despite the raw animalistic lust that lay heavy in the room, she still looked so composed. She smiled down at him with her beautiful smile, prettier than any girl he had admired back in high school; the girls who had never noticed him. Abby had noticed him, she had captured him, she had taught him and now she was taking him. The lovely schoolgirl of his dreams, smiling sweetly for him, while she fucked his asshole to a quivering mush.

"That's it. Squeeze me tight - here...it...comes."

The mounting pleasure within him reached a crescendo just as Abby let out a moan, slamming into him with all her might. His own hips bucked involuntarily against her, and he could feel her thick cock start to spasm.

"Aaaaah." He let out a gasping cry.

Deep inside him a burst of warmth suddenly bloomed, pulsing and expanding with each twitch of Abby's dick. She was filling him, her love seeping into him like a warm balm.

He felt strangely proud in that moment. For all the failures in his love life up to now, he had succeeded in something. His poor, pathetic body had served this Goddess, and brought her to orgasm. And now she marked his insides as her own.

The pleasure roiled through his body, and he panted desperately, vaguely aware of his own climax, his own member twitching and splitting, completely untouched. He tossed his head from side to side, toes curling once again, overwhelmed by the feelings inside him. All the while, Abby watched him intently, her eyes sparkling with her own excitement, her endless orgasm filling him with her searing cum.

Finally, unable to take everything in, Simon tossed his head back, screwing his eyes shut, waiting for the tide to wash over him.

It could have been a matter of seconds or hours before he came down from his orgasmic high, to the feeling of Abby stroking his cheek. Blinking his bleary eyes, he gazed up at her. Like an angel, untouched by the rigors of the world, she met his gaze warmly.

"Good boy." She said, softly, "You did so well. You made me feel really good."

Giddy from the praise, Simon grinned stupidly up at her.

"Did I make you feed good too? I think I did."

"Oh god, yes." He croaked, "Yes. I never...I mean, I...I don't know what to say. Thank you. Oh god, thank you."

"I told you I was good." Abby gave her hips a little shake, and Simon let out a yelp as he was instantly reminded that she was still sheathed within him, "And I love helping boys enjoy their first time."

"I...you're so amazing."

"Thank you!" Abby said brightly, "You're not so bad yourself. The tightest little asshole. I've not cummed that much in a while."

"I can feel it." He murmured.

"I bet you can! I cum a lot anyway, and this was a corker!" She leaned in close, "Your butt has been marked, now. I've claimed it with my jizz."

"Forever." He said.

"It's a promise!" Leaning against him once more, careless of Simon's own more modest seed spilt out across his chest, Abby kissed him again.

Eventually Abby pulled out, her erection finally subsiding somewhat. Her cock, slick with a mixture of lubricant and cum, slipped out easily, bringing an emptiness that surely only a ten inch rod could achieve. His asshole, suddenly free of titanic obstruction, felt widened and exposed in the open air. Almost immediately, like an uncorked bottle - which, he supposed, he more or less was - Abby's thick, warm seed start to seep onto the bed.

Cheerily, Abby went to get a towel to clear up the mess. As she flitted around the room the girl made idle small talk, and he tried to keep up as best he could. Somehow, the situation seemed even more absurd than the sex; the beautiful schoolgirl mopping up her cum leaking from his ass while complaining about roadworks that had messed up her bus route.

Eventually satisfied, she stood at the foot of the bed and looked down at him.

"So, lazy bones, can I interest you in a shower?"

Abby's shower, as it turned out, was more of a full on wet room than a small cubicle. The shower stood at the far side of the room, a large section of floor partitioned by a slightly raised section of tiling, with a glass barrier closer to the mounting. Simon gingerly walked over, still clenching his abused butthole to keep from spilling the rest of his creamy cargo.

Abby followed him inside, skipping in front of him to turn the shower on as he stood watching dumbly.

Once the water was running and she had checked the temperature, Abby turned back to face him. With a well-practised tug she loosened her tie, tossing into a corner of the room, before starting to work on her shirt buttons.

"I thought I'd join you." She said.

Simon's eyes were drawn to her impressive chest as she popped open the buttons. The white fabric, still pristine and unruffled, fell open a little as the tension was released, revealing the creamy curve of her substantial cleavage.

She quickly shrugged her shirt off, tossing it after her tie, before turning her attention back to him.

"So," she said, smirking at him, "what do you think. Do you like my boobs best - " for emphasis, she folded her arms beneath her chest, thrusting her already full, firm breasts up and together, " - or do you like my cock?" With a shake of her hips she drew his attention down to where her thick python bounced and swayed, already hardening once again.

He found himself mesmerised as she made her penis dance around, the meaty length swinging like a club. Just minutes later, and with her warm cum still leaking out of his rear, it seemed unbelievable that it had been inside him.

"Jeez, I get it," Abby laughed, "boys always love my cock the most."

Blushing, Simon looked up to meet her eyes.

"Hey, I'm not complaining." She said with a wink.

She followed him into the shower and turned on the warm water, pointing out all the shelf with all the soaps and gels. Relieved, Simon finally allowed his butt to relax, letting more of Abby's thick semen ooze out of his ass and down his legs to the shower floor. Abby spotted it and give him another of her smirks, but didn't comment.

Simon was surprised as how comfortable it felt, showering with Abby. He was awkward with girls at the best of times, and absolutely beauties like Abby left him completely tongue tied, yet somehow he was able to stand so close to her stunning, naked self and clean up without dissolving into a gibbering mush. Maybe being fucked had broken down some of his barriers.

Abby talked constantly as she washed, and mostly about sex. She describe her conquests of various boys in her classes at school; the popular boys, the nerds, the sports stars - none seemed immune to Abby's charms

"If a cute guy is desperate to take my dick I'm hardly going to say no." She said with a shrug, "My school is full of slutty boys."

"I can see how you might have the effect."

"Oh, you charmer." She said with a giggle, "And you're one of my slutty boys too, right?"

"I...I guess. For you."

Abby squealed happily, leaping forward to hug him from behind. Simon froze, his breath catching, as her breasts mashed against his back and her hands ran across his bare chest. He heard her humming as she rested her head against his shoulder.

"Hey, I'll wash your back."

With practiced hands Abby lathered him up and started scrubbing gently with a loofah. Simon stood facing the shower, closing his eyes and relaxing as the water ran down his face.

As she cleaned Abby's hands wandered a little, all lingering touches and gentle squeezes. It was a nice feeling; something low key and calm to follow the punishing fucking she had delivered only a short time before.

"You've got a cute body, you know." Abby said absently.

"R-really?" He managed, surprised. No one had ever really complimented his looks before. He was the dorky, quiet fashion disaster; why would they ever?

"Oh yeah. Nice and lean, but not all skinny and weak." She said, "Just my type. I don't like tiny sissy guys, you know? I like men who are men; it makes it hotter when I bone them."

Simon found himself blushing again. Her casual sexuality, the matter of fact way she talked about such an unusual...configuration was so out of the norm for him.

"Do you..." he said weakly, "Er...do you ever let guys...you know..."

"Hmm?" She hummed the question at him.

"Um." He stammered, struggling for words, even with someone as open as Abby, "...I just wondered, you know? If...er...if you ever do things the other way around. Like...er...let a guy..."

"Oh, nope, that's not for me." Abby said with a laugh, "I like fucking guys, and guys who come to me get a big dick up their ass. It's win-win, really."

"R-right. Of course."

"I mean, maybe, if I had a proper boyfriend we might mix it up occasionally, if he really wanted to." Abby continued thoughtfully, "But he'd still be taking it pretty much always."

"Got it." He nodded.

"Why, are you interested?" Abby said mischievously, one of her hands roaming around to the front of his body, teasing down towards his crotch, "I don't think you are. If I can fuck an orgasm out of a guy on the first go I just know he's made for it."

"No!" He said quickly, "I was just...curious, is all. I don't know how these things work at all."

"I'm just messing." Abby said with another giggle, wrapping he arms tightly around him. Simon let out a gasp as he felt her full, firm breasts press into his back, and her thick, hard cock press into him a little lower.

The stood in silence for a moment, as the water cascaded over them both, with Abby's hands gently running up and down his torso. It was a wonderful feeling to be held by a beautiful woman, the raging hard on resting between his ass cheeks notwithstanding. Heart pounding, Simon let out a gasp as one of her hands wandered down to his crotch again.

"Looks like someone is ready to go again." Abby said softly, a whisper directly into his ear.

As she squeezed him, she also began to move her hips against him. Her cock slid between his cheeks as she did so, a thick, meaty hotdog between his anxious buns.

"Abby." He mumbled, weakly.

"Why don't you bend over for me?" She said, breathily, as she released her grasp around him after one final pull at his dick.

Pulse racing, Simon almost fell over in his effort to comply, before steadying himself with his hands against the wall, eliciting another of Abby's sweet giggles. She rested one hand on his hip, the other running up and down his back whilst she continued to slide her cock back and forth against him.

"Could you bend you knees a little?" She asked. Simon mentally slapped himself for not thinking of it before.

"Y-yes!" He said, the word coming out as a strangled squeak.

"Good boy." Abby said approvingly as she reached over to pluck a bottle from amongst the soaps and gels. "This is view I'll never get tired of." She gave his ass a gentle slap, and he let out a surprised gasp in response.

Looking back over his shoulder, he could see she was working her cock once more with lube, the slick squelch of her hands running back and forth audible over sound of the shower. She caught his eye, and gave him another dazzling smile.

"Are you ready for this? You've had a warm up now, so I'm going to go a little harder this time."

"Yes." He said, "Yes, whatever you want."

"Whatever I want?" She grinned wickedly. Looking down, she started lining her cock up with his entrance. He felt the bulbous head resting against him. "You might not be quite ready for that, but I'll give you a good...hard...fucking."

As she spoke the last words her hips started moving forward, and she entered him with much more ease than the first time around. He gasped as the pain returned, duller than before, but this time she kept pushing, burying herself inside him in one long stroke. Her hip bumped against him moments later, and he knew she was full sheathed.

 "You okay?" Abby said, stroking his back encouragingly, "I thought I'd taught your ass a lesson, but it's like it's trying to squeeze my dick off again."

"It's good." He gasped, realising the truth of his words even as he spoke them. Already the feeling of being full and the strange pleasurable sensation deep inside him were welling up and overwhelming the pain. Maybe he truly was made for this.

"Mhmm. You ready for me to start giving your prostate a good pounding?"

"Yes!"

With that, Abby placed both hands on his hips and started to pump her hips. The now familiar explosion of pleasure and pain erupted as she did so, and he could help but moan aloud. She picked up the pace quickly, driving into him with long, fast strokes that jolted him forward each time she bottomed out. Each thrust was accompanied with a loud slap as their bodies came together, and her heavy balls thudded against his. Whatever button she had found inside him flared time and again, the exotic pleasure drawing loud groans out of him.

"That's it, sweetie, moan for me." Abby said, her voice breathy, "Your ass feels so good, I want to hear you're enjoying it too."

"It's so good." He managed, "God, fuck me. Please, fuck me harder Abby."

"It would be my pleasure."

Tightening her grip on his hips, Abby upped the tempo once again. Each thrust slammed into him, her massive meat ploughing through his body and churning him up inside. As she drove her hips into him she pulled firmly back on his waist, driving him down onto her cock each time. It was like being impaled; he was completely skewered by her manhood, and all his fevered brain could manage was a desperate thirst for more.

"I'm going to ruin your ass, Simon." Abby panted, her voice punctuated by her own cute little groans, "Once I'm done with you nothing else will do. Only my big fat cock will satisfy your thirsty hole."

"Make me yours, Abby."

"I will, sweetie. I'm going to hammer my imprint so deep inside you."

"I'm close Abby - oh god." He could feel it clearly now, just like the first time, but even more intense. The same whirl of pleasure and pain churning inside him, throbbing brightly with each of Abby's mighty thrusts.

"Cum for me, Simon." Abby breathed, "I want to screw every drop of jizz right out of you."

He could barely hear her now, as the wave began to crash over him, urged on by the constant attention of her cock. There was no escaping, and the pure ferocity with which she fucked him drove the sensations to new heights. His body felt far away; knees weak and trembling, arms numb, and vision cloudy. Everything except his ass and cock, which bounced stiffly along with every slap of Abby's body against his.

"Ah - ah!" He moaned, fingers and toes curling all at once, "I'm...I'm...aaaaah!"

His orgasm exploded out of him, as though physically driven from his body by Abby's relentless pounding. The pleasure swam through his body, with a singing high note accompanying every one of her thrusts. Feeling overwhelmed again, he could do little more than let out an inarticulate cry as his seed spat out into the swirling waters of the shower.

"I'm almost there." Abby breathed, "Keep squeezing like that. Your ass is so...fucking...tight."

Just as his own orgasm started to subside, and Abby's strokes started to stoke a growing over-stimulation, he heard her gasp, slamming into him with all her might.

"Here...it...comes." She groaned excitedly, "Take it all, baby."

Once again he felt her thick length jerk and throb inside him, pulsing fitfully against his abused body as she shot her viscous cum into him. He could physically feel the pressure build within himself as her warm load flooded in to his already packed rear, mixing with the remnants of the deposit she had already left him earlier.

With a long, satisfied sigh, Abby flopped down upon him, wrapping her arms around his chest and clinging tightly. Her full breasts pressed flush against his back, whilst her panting breaths ghosted across his neck. It was like heaven; all her womanly charms assailing him, while she simultaneously pumped him full of cum.

Even as her own orgasm started to subside, Abby humped him a little more, grinding her hips, the small movement still enough to churn her cock inside him as she seemed determined to wring out every last drop of her seed. Even now, in his post orgasm haze, her every little twitch sent his over stimulated senses strumming.

"Oh that's good." She murmured softly, squeezing him tightly.

"Aaaah." He let out a long, shuddering breath, barely able to form thoughts, let alone words.

"Mhmm." She whispered softly in his ear, "I like that. That's the sound of a boy who's been well and truly fucked."

"I'm so full."

"I should think so, with two loads to keep my cock company." Abby giggled, "You've done so well, Simon. Anyone would think you were a seasoned slut, with how well you've taken to this." She gave another twist of her hips, grinding into him and forcing another gasping yowl unbidden from his lips, "Well, if you weren't so damn tight. I really love breaking in virgins."

"I love...I really love it too." He said, arching his neck to look back at her, "I never thought it would be so amazing."

"Well!" Taking advantage of his change of angle, Abby stretched forward to capture his lips with her own. For a moment Simon was lost in bliss again; her huge, still hard cock stretching out his ass, hot with her fresh cum; her slender body pressed up against him; her massive breasts against his back and her delicate hands roaming up and down his chest; her darting tongue invading his mouth with skill and confidence. Each one just hours before would have been a far off dream in his life - now Abby granted them all at once.

After thirty seconds or an hour she broke the kiss.

"Now you know. And next time will be even better."

Once Abby had withdrawn from inside him, teasing all the way, they returned to cleaning up. This time things were more functional - Abby had obviously been intending to fuck him in the shower all along, so now that they were done it was time to clean for real.

Simon was a little unsteady on his feet for all the exertion, with his ass throbbing and dripping, but Abby immediately recovered all her poise. Catching sight of himself in the mirror, Simon could see he had been through the wars, but Abby looked as pretty and unflustered as ever. No one would ever have thought she had just fucked him senseless - twice - just moments before.

This time around she paid special attention to his ass, helping him clean out as much of her semen as possible now that she wasn't planning on dumping more in there. He was sore and abused, but still full of adrenaline, and she was wonderfully gentle.

Finally, after drying and dressing, he found himself standing in her hallway, looking down at the small, beautiful girl who had rocked his world so deeply.

"So..." He said, nerves taking over despite everything, "I...er...owe you...er..."

He'd never even asked how much she charged. In all the craziness of the situation, from her swooping on him in the street, to leading him through the craziest of sexual situations, it had been driven from his mind. But that's what he had come for.

"Hmm?" Abby smiled up at him, "Oh, silly. You don't owe me anything. I took payment of one cute boy's anal cherry already."

"But...I mean..."

"Shhh." She put a finger on his lips, "Whatever you are thinking, today wasn't that." Her eyes sparkled with amusement; she'd obviously known exactly what he was thinking, "I had lots of fun filling you up. Next time, maybe you can take me out for a nice meal as payment, hey?" Tugging his shirt, she pulled him down so that she could whisper in his ear, "And afterwards, I can fuck you so hard you won't be able to walk for a week."

"I...I would like that." He stammered.

"Then I'll give you my number." She cocked her head, looking thoughtful, "Actually, why don't you give me yours too? That way I can sort it out and we don't have to wait for you to build up the nerve. Best for everyone, right?"

"R-right."

"Great!" Abby said with a happy cheer.

After exchanging numbers, she gave him one last lingering hug, her roaming hands squeezing his ass as a final reminder of her ownership. Simon just held her tightly, taking one final moment to burn the sensation of having her in his arms to memory.

"Right...I better go." He said at last, releasing her and taking a half step back.

"Okay." Abby replied with an easy smile, "Thanks for playing with me today, Simon."

"N-no, thank you. This meant...so much to me." Simon mumbled, struggling for the right words as always, "It's like you've shown me a new world."

Amazingly, Abby flushed, but her smile grew even wider.

"Jeez, you better get going before I jump you again." She said with a laugh, "You sexy little dork."

Simon couldn't help but grin himself, his own face heating.

"Well, bye then."

Hopping forward, Abby took his face in her hands and offered one final, small kiss.

"Bye bye, Simon." She said warmly, "Until next time."

The apartment block was quiet and he didn't come across anyone else until he let himself out. Half in a daze, he wandered back towards the subway station, vaguely aware of the soreness in his behind as the adrenaline that had been coursing through him finally started to subside.

Halfway back towards the subway station, he felt his phone buzz. Hooking it out, he saw a new message, from Abby.

Here's something for you to enjoy!

The message was accompanied by a photo. As soon as it popped up, Simon flushed, looking frantically around to make sure no one was close enough to see his screen.

The photo was of Abby, taken in her bathroom mirror. She was wearing her white shirt and tie again, this time with a navy blue jacket that matched her skirt. Below the waist, she was naked, and the hand not holding her phone was wrapped around her huge erection, directed pointedly towards the viewer.

Another buzz: Next time you jack off I want you to look at that picture and imagine my big fat cock inside you again!

As if he would be able to think of anything else. Smiling, he sent a short reply.

You got it. Thanks for the pic.

He waited a few moments for any reply, then put his phone away and set off again.

Grinning like an idiot, tired and achy, but happier than he had been in the longest time, Simon went home, his mind filled with a beautiful young woman with a beautiful big cock who had changed his life forever.


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