A Fortunate Encounter

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.