Hadley's Other Cherry Ch. 02

Before he knew it, he was ready to explode again. "Goddamn," he groaned in disbelief, "Hadley, baby, I'm gonna cum..." He pulled his thick wet cock from her swollen lips and aimed it at her freckled a-cups. He moaned as his balls spasmed, spurting two or three thick ropes of white cum in between her tiny tits, her sensitive pink nipples stiffening as he shot his load.

When he came down from his second powerful orgasm of the night, he looked down at her shining face and smiled. "I think we should clean you up a little, don't you?" he asked mischievously.

Still naked, he led her into the pristine hotel bathroom and turned on the bath. "Get in," he told her, smiling.

Hadley hopped into the bathtub, testing the water with her foot, and wrinkling her freckled nose in reaction. "It's lukewarm," she protested.

"You don't want it to be too hot," he explained, "you'll get scalded." She watched him switch the water to the handheld shower head, and he pointed the stream of water at her sticky chest. He gently sprayed her tiny tits, washing the evidence of their love play away from her young breasts. The water felt cool and refreshing. "Now get on your hands and knees, honey."

Hadley knelt down in the shallow water on all fours, her head looking at Jack quizzically.

"No, Hadley, turn your bottom towards me," Jack corrected her, amused at her innocence. Hadley laughed as she wiggled around so her head was facing the faucet. Her ass was raised in the air tantalizingly offering him a glimpse of her jeweled butt plug, and some of his pearlescent cum still clung to her swollen, well-used pussy. He parted her pink nether lips with his fingers, studying a thick drop of semen that was slowly dripping out of her hole and onto her perfect little clit. She shivered as he rubbed his cum onto her swollen clit, and then felt the gentle spray of the shower head as he rinsed her off.

When she was all clean, Jack turned his attention to her sweet asshole again. He could hear her suck in her breath as he wrapped his fingers around the edge of the plug and pulled gently. He worked the plug in and out of her tight back door until it finally dislodged. Hadley shivered and groaned as the metal object slid out of her slippery asshole.

Jack rinsed off the plug and set it on the edge of the tub and then turned his attention to the delectable sight in front of him. Her tiny pink knot of an asshole, which had gaped open slightly when the plug came out, had already fluttered closed and sealed itself up into a (slightly more loose, but still pretty tight) knot again. He ran his finger over the little pink pucker between her cheeks and groaned his pleasure. When he finally got to take that virgin ass it would feel so amazing, he thought.

"Stay just like that, Hadley," he said as he stood and walked out of the bathroom. He grabbed the bottle of lube off of the end table, and a box from the drawer, and returned quickly. He squirted a small dollop of the thick substance on his finger and began working it in and around her tight backdoor. After a minute, he was pleased to notice that his index finger gained quick entry into her warm cavity.

"Good girl, Hadley," Jack cooed, as he started to saw his finger in and out of her tight tailpipe, "You've been practicing, it's very clear."

"You're pleased with me?" Hadley asked hopefully.

"Oh yes, baby girl, I'm very pleased with you," he replied. He withdrew his finger and applied more lube. Then he pressed two fingers against her small orifice. She grunted as his thick fingers pushed into her asshole. "Are you okay, baby?" he asked.

"Yes, Jack, it just feels so... intense..." Hadley gasped again as Jack slowly started sawing his fingers in and out again. Jack had already cum twice, but he could help but get hard again at this incredible sight. The pink ring of her open ass clung to his lubed-up fingers with every thrust. Damn, he wanted that tight hole.

"Are you going to fuck my ass?" Hadley asked. Jack could hear the worry in her voice. She had come so far since last week but he knew if he wanted her willing, he couldn't push her that far today.

"No, not today, baby girl," Jack said to her, still fucking his thick fingers in and out of her slick chute. He felt her relax slightly in relief. "We're just going to practice opening you up. I promise. Now, Hadley, I want you to play with that sweet pussy for me." He watched her as she reached her slim fingers underneath her and began to rub her swollen clit. "That's a girl."

As Hadley played with her throbbing pussy Jack could feel her asshole flower open slightly, giving his fingers even more room to manoeuvre. "Good girl..."

He rested his other hand on her lower back, holding her in place while he slowly began to separate his fingers in her asshole. She moaned at the intense feeling. "Keep going," he urged her, "just breathe through it."

Slowly he scissored his fingers open and closed, stretching her tiny hole, until he could separate his fingers a full inch apart. He couldn't help himself: he pooled some saliva in his mouth and then spit into the small opening, perversely enjoying this lewd act. He smiled as he imagined how good it would feel to slide his cock up her well-lubed butthole.

Jack snapped out of his reverie when he realized, much to his delight, that his innocent little princess was hunching her tight ass into his hand, fucking herself with his slippery fingers. That little vixen! He thought to himself. She's a fucking natural...

Jack pushed back at her, fucking his fingers in and out of her greased chute as she quickened her pace, diddling her hanging clit at a furious rhythm. All of a sudden, he felt her body shudder, as she groaned and panted through a toe-curling orgasm. Hadley felt the tingles all the way through her body as her spasming asshole clenched involuntarily around Jack's fingers. Finally, she collapsed forward in the tub, his fingers dislodging from her wet ass with a slurp.

"Oh my God..." she moaned, "That was incredible..."

Jack, pleased with his protegée, wiped his fingers on the bath mat and reached for the box at his feet. He opened it and took out a slightly larger plug, this one with a purple jewel. He quickly squirted some lube onto the plug and spread it around the bulbous head with his fingers.

"Hold your cheeks open for me, Hadley," he instructed. He was pleased to notice that she did as she was told automatically, even as she asked him why. "I got you another present," he replied. He slowly but easily slid the bigger plug inside her loosened hole until it was lodged in place.

"What's that?" Hadley asked, gasping at the intense sensation in her still-sensitive asshole.

"It's a bigger plug," Jack replied. "This will help get you ready for my cock."

"When will that be?" she asked with a shiver in her voice. He could sense her fear, but also her anticipation. He had her right where he wanted her.

Jack smiled in response. "On prom night. When your friend is losing her virginity to some clueless high school boy, I'll be taking your virgin ass."

To be continued...