A Fortunate Encounter

"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.