Anything I Want?

They were both nervous as she opened the door and let him in. His eyes wandered over her body for a lovely minute before he caught himself and forced his eyes back to meet hers. Jackie was terribly nervous, and could not help but to wisecrack.

"I expected you to knock at the back door," she said with an arched eyebrow and a grin.

Jake laughed too hard at the jibe, clearly as nervous as she was. She took the offered flowers and sniffed them approvingly. Once again she raised an eyebrow when she read the label on the wine. Neither of them were really oenophiles, but this was a serious bottle of wine by almost anyone's standards. Jake was really pulling out all the stops on this, Jackie realized.

She took the time then to really look him over. Oh, he was a good-looking guy. That had never been a question in her mind. Despite how annoying he could be, she had always known he was a handsome man. He wasn't out-of-her-league gorgeous, but he was very attractive. He was almost a foot taller than she was. She reached up and began unfastening his tie after she had set the flowers and wine on her kitchen counter.

"You, sir, are overdressed," she said softly.

"Sorry," he croaked. He was far too nervous to make an attempt at humor.

"Kiss me, Jake," she ordered in that same soft tone, her hands deftly removing his tie and tossing it to the floor.

He complied, his lips gently seeking hers as she continued to undress him. Jake was a far better kisser than she had imagined. Jackie was on fire with lust as she removed his shirt and cast it aside. Jake managed to maintain the kiss as he kicked off his shoes. Jackie unbuckled his belt and trousers and let them drop to the floor.

Oh, boy, she thought, that is bigger than I thought. That is one huge dick.

The massive pillar of cock meat protruding from the front of those boxers was worthy of a porn star. One of the better-endowed porn stars, at that. Jackie had lubricated her asshole and prepared it with her biggest dildo, but even that monster was still not quite as big as the real thing.

This is really going to stretch my ass wide open, she thought. That thought made her pussy drool in anticipation.

Jake was completely at a loss for words when Jackie reached out to squeeze his erect cock in her small hand. Her nipples looked incredible as they poked against the lace of her sexy gown. He followed automatically when she pulled him along by his dick. Jake had never been to her place before, and felt like he should say something complimentary about her condo. He just couldn't take his eyes off of her mesmerizing ass or form a coherent thought.

This had been his fantasy forever, and he just expected that it would end as it always had, with him disappointed but trying to be a nice guy about it. That sweet ass looked like the stuff of his wet dreams, close enough to touch. He did reach out and gently squeezed Jackie's taught cheeks when she stopped at the side of her bed and looked over her shoulder at him.

"Oh, god," he moaned. Her asshole was glistening when her cheeks spread slightly. She had lubricated it for him. She was completely serious about letting him fuck her in the ass.

She turned and slid his boxers down his thighs, opening her lips to take the tip of his bloated cock head into her mouth. She moaned around that salty mouthful as Jake carefully stepped out of his underpants. Jackie licked her way around his head and shaft, until the length of his cock was wet with her saliva. It was all a delicious preamble, not intended as proper lubrication. She gave the tip one final kiss before rising to her feet.

Jackie reached over to her nightstand and handed him the bottle of lubricant. "Do you know what to do?" she asked. Her face was completely serious, as was his response.

"I have been waiting for this my whole life," he breathed. "I know what to do."

"Good," she replied simply, turning and sliding onto the bed. Her shapely bottom was pointed directly at him, and her hands reached back to spread her cheeks open invitingly.

Jake carefully lubricated the length of his cock before setting the lube down within easy reach. Thanks to his height advantage, he was able to pull Jackie's hips toward him, lining up the bulbous head with her tight little pucker as he stood by the bed. Jackie looked over her shoulder at his lust-contorted face. She felt the heat of his mushroom head as it pressed against her tight little ring.

She carefully controlled her breathing and her fear. She focused instead on the obvious, naked hunger on her longtime friend's face instead. God, he looks so hot, she thought. She could not help but gasp, though, when she felt her sphincter being spread open by that massive cock head.

Jake jerked reflexively when he heard her sharp intake of breath. He stopped trying to press forward and held still. "Am I hurting you?" he asked in a pained voice. Years of rejection showed on his face, and it was clear to Jackie that he expected this to be the end of it.

"Don't you dare fucking stop," she hissed at him, meeting his eyes with a determined horniness that matched his. "We didn't get this far just to quit now. Stop teasing me with that dick, and start giving it to me!"

Jake's hands shook on her hips. It took all of his self-control to make sure he did this right—the way he had practiced it in his mind, just in case he ever got the chance to actually do it. His eyes flitted back and forth from Jackie's face to her asshole as his thick cock head stretched her wide open. They both gasped out loud in disbelief when the ridge finally slipped inside that maddeningly tight little ring.

"The...the head is inside," Jake groaned, licking his dry lips to form the words.

Jackie was breathing heavily and just nodded in response. Her tortured little asshole felt impossibly stretched by that thick cock. It was all she could do not to cry out. She knew, though, that if she did he would likely pull it out. That would hurt more, and she desperately wanted to feel that massive member deeper inside her. She dropped her forehead to the sheets and managed to speak.

"Keep going," she croaked out. She hoped she didn't sound like she was in pain.

It did hurt, but it also sent shivers of sensation the likes of which she had never imagined. She saw stars, fireworks, and other flashes of light as she nearly blacked out. Oh, it hurt like hell! At the same time, the pleasure was already almost orgasmic. That rubbery little ring of muscle was stretched further than she had ever thought it could be, but it was starting to grudgingly relax around the thickness of that massive shaft.

Jake held still with the head and the first inch of his shaft buried in the impossible tightness of a woman's ass for the first time. He carefully controlled his breathing as his eyes feasted on the vision. Even if this was as far as it went, he would savor that image for the rest of his life. He held still and felt the muscles of Jackie's bottom squeezing him delightfully. Oh, he wouldn't come from this. Still, it felt amazing.

It was a real shock when she started pushing back, slowly forcing more of him inside. He stopped breathing entirely and watched his cock disappearing little by little. After three minutes, he took a ragged, noisy breath of air.

"Jesus," he groaned. Half of his massive dick was now inside Jackie's ass! This is really happening! his mind screamed. You are fucking Jackie IN HER ASS!

He suddenly remembered his 'training' from reading all those books and watching all those instructional videos. He reached over and grabbed the lube, dribbling a bit more of the stuff around the juncture of his shaft and her sphincter.

"Damn, that's cold," Jackie grunted.

"Sorry," he replied in a whisper.

She groaned again as he pulled back slightly, working the slippery stuff around his shaft before sliding it slowly deeper into her clutching bowels.

"Oh, fuck!" she gasped out. The thick ridge of his cock head had just mashed her g-spot through the thin walls separating her hungry holes. Her body shook as a mini-orgasm shook her to the core.

Jake read her reaction correctly for once, and he held still and savored the tightness gripping his cock. He waited for her to relax again, and then he slowly slid another inch in before pulling back and applying more lube. He set the bottle down and leaned over her back, reaching his hands up under her gown to find and fondle her aching breasts.

"Jackie," he murmured, "your ass is fantastic. I still can't believe I'm fucking you in the ass."

She groaned as she felt his thick glans once again pressing deep inside her. He slid in and out, very slowly, three more times. She let out a gasp when she felt his balls touch her soaked pussy lips. Her head came up off of the bed, and she turned her wide-eyed face to his.

"It's all the way in!" she whispered in disbelief. He nodded, but his wide eyes let her know that he couldn't believe it either.

Their panting began to synchronize as Jake slid in and out of her with full-length strokes. Those were almost painfully slow...at first. A glance at her bedside clock revealed that they had taken almost half an hour to get to this point. However, the hard part—the 'work'—was done. Jackie's asshole was now comfortable with the girth that was sliding in and out of it.

"Faster!" she hissed.

Jake released her hanging breasts and rose to grab her hips. He shook his head in disbelief once again as he watched his glistening shaft drive in and out of that sexy little butthole. Her shapely little bottom shook and the muscles rippled each time he thrust his hips forward to slap against her.

"Oh, fuck. Oh, fuck! Oh, fuck!" she muttered as he built up speed and fucked her ass. "Coming!" she let out as a strangled cry.

He stopped thrusting, but only for a moment.

"No! Keep going!" she howled.

She didn't have to ask twice. Jake was reveling in the amazing feel of her tight ass as he pounded his full length in and out of her. He did slow down briefly to reach over and add more lube, but he was being overly safe at that point. Jackie was delirious as he pounded her horny asshole.

"Yes! Yes! Fuck my ass!" she cried out.

All too soon, he felt his balls clenching up. "Oh, fuck!" he bellowed, "I'm going to come!"

"YESS!" she cried out loud, "Do it! Come in my ass!"

Jake's cry was strangled, and his whole body shook as he erupted inside her. Jackie once again saw a light show as her own orgasm exploded through her body. They shared what looked like an epileptic fit as they jerked out of control with the intensity of that shared climax. After his cock slowed to gentle pulses of cream inside Jackie's ass, they both collapsed forward onto the bed.

They panted together, and Jake's lips found her earlobe and nibbled on it while he struggled for breath.

"That...was amazing," he panted into her ear, "Thank you...so much, Jackie."

She turned her head and her lips found his. She kissed him back, and then softly bit down on his bottom lip.

"I hope you don't think we're done," she said.

Jake's dick lurched and started to harden again inside her stretched and well-fucked asshole.

"Mmm. That's better," she said, kissing him again. He pulled back and thrust his renewed erection into her ass with a wet smack! "MUCH better!" she gasped.

Round two was just getting started. His knees got between hers and forced her legs wide apart as his dick pounded her. Jackie gasped and came over and over as her body was pinned, helplessly wide open beneath his. The angle of penetration was unbelievable—it felt like that fat cock was just thumping directly into her sensitive g-spot every time it drove into her ass.

The sheets beneath her hips were drenched with her juices and the massive load from Jake's first orgasm as his cock forced it out of her. She did black out, briefly, following a particularly intense orgasm. When she came to, he was still relentlessly fucking her ass.

"Wait," she managed to gasp out. After two more thrusts, Jake held still. He was breathing heavily into her ear.

"Do you need to stop?" he asked softly.

"Just for a bit," she said, "I'm having trouble breathing like this."

"Oh! Sorry!" he said, quickly rolling off of her.

They both shivered as his impossibly long shaft slid out of the tightness of her bottom. Jackie rolled onto her side, facing him in her bed. She cradled his face in her hand and kissed him softly while looking into his eyes.

"I wasn't sure I would be able to go through with it," she said softly after that kiss.

"To be honest, I really didn't expect you to," he grinned in reply, shaking his head sympathetically. "That couldn't have been easy for you."

She reached over and found his cock, stroking it gently. "No, it was not," she replied. "But it was totally worth it."

She kissed him again, pushing her tongue into his mouth and letting him know they were not done before pushing him onto his back. His eyes lit up as she reached for the lube. She squatted above him, looking impossibly sexy as she slid his freshly-lubricated cock back into the welcoming heat of her tight ass.

"Oh, god," she groaned as she sank down on him.

Jake reached up to squeeze her breasts as she rode him, and she whipped the gown over her head to give him better access to them. He sat up as best he could to worship her nipples with his mouth. His hands reached around to cup and squeeze her bottom as she bounced up and down. She was taking him like a champ, and her orgasmic cries just made it that much more intense for both of them.

Jackie shook through one final, crazy orgasm before she had to stop. They were both awfully shaky as they walked out to the kitchen. She poured them each a tall glass of ice water, and sat on his lap at her dining room table. He was still fully erect, and his shaft protruded between their bellies as she faced him and sipped her water. She swallowed the water in her mouth, and reached down to touch the huge dick once again in disbelief.

"Still can't believe it fit inside you?" he asked.

"That, and I can't believe how much I want it in there again," she replied.

Ten minutes later, she was pressed against the wall in her shower as that gigantic cock once again pounded into her horny asshole. She shook as she felt him thicken inside her, and they both cried out when he filled her ass with a second massive load of cum. Once again, she was struck at just how gentle he could be. Her legs failed after that intense orgasm, but he caught her and held her carefully until she regained her strength. Afterward, he was tender as he cleaned the sloppy mess out of her well-used bottom.

He was every bit as thorough and careful as he gently sponged the rest of her sensitive body clean beneath the warm spray. He dried her body and her hair, and even brushed her hair as he stood behind her in front of the bathroom mirror. She felt him touch her right buttock, and reached down to find his cock. Once again, he was getting hard. Jackie looked at his handsome face in the mirror as her hand closed on the fat shaft of his dick.

She was wondering how many times that amazing dick could come in one night. She smiled softly when she realized it had become her goal to find out.

"What's so amusing?" Jake asked her when he saw that smile.

"I just realized we're not done yet," she replied, "and I am surprisingly happy about it."

"Good," he said, "because there is something I have always wanted to try."

They made their way to the living room, and once he had thoroughly lubricated her ass, she found herself bent over the back of her couch. Jake was careful, once again, but it took only a minute before she was ready for another vigorous pounding. Jake stood behind her and feasted his eyes on the incredible sight of that sexy bottom once again surrendering to his thick cock.

His phone started going off in the pocket of his discarded dress slacks, just a few feet behind them.

"Who could that be?" he gasped, still driving into her sexy backside.

Jackie started to warn him not to stop, but then she thought better of it. "You should probably unh! see who it is," she grunted.

Once again, they both groaned as his slick cock slowly withdrew from her tight embrace. He grabbed his phone and answered it without bothering to see who it was, feeding his cock back into her hungry sphincter as he spoke.

"Hello?" he said.

"Well?" Andrea's voice came over the line, "Did she actually go through with it?"

"Not yet," he lied, as his cock slowly pistoned in and out of Jackie's tight and welcoming asshole. "I think we are both way too nervous for it to actually happen. Maybe if we had a second or third date, it could."

Jackie bit her lip to hold back her groan as she listened to Jake and felt his massive dick fucking her ass again. She was already coming. She understood what he was doing with this phone call—paving the way for more sessions like the one she was currently relishing, while at the same time keeping it secret.

"Well, I have to tell you," Andrea said, "I can not believe how turned on it got me, just thinking about it."

"You know she's right here?" Jake said, cutting her off, "She can probably hear what you're saying right now, Andrea."

"Oh!" Andrea gulped, "Sorry! I'll let you get back to your 'date' then. Will you be over tonight?"

"Maybe," Jake replied, really thrusting hard into Jackie's eager asshole, "depends on how long I'm here. I'll call and let you know, okay?"

"Okay."

Jake hung up and dropped the phone. His hands seized Jackie's hips and he gave her a series of really strong and deep thrusts. She once again cried out loud as one orgasm gave way to a more powerful second one. "OHMYFUCKINGGOD!" she screamed.

Jake had been right on the verge of his own orgasm, but he held back and slowed his pace. He wanted to continue, and feared that the third load from his balls might drain them for the night. Jackie's phone started to ring, then. Jake pulled out and she waddled over to her counter to pick up her phone.

"Hey, Sally," she said, settling onto a bar stool. She swiveled her hips from side to side, her ass hanging invitingly off of the back of the stool facing Jake. His cock wagged in front of him as he stalked up behind her to take that inviting ass.

Jackie shivered when he entered her, but she managed to control her voice on the phone. "He's still here, actually. I'm not sure I can go through with it, you know? Oh, here he is. Mind if I call you back later?"

Once again, she bit her lip. She threw her head back and sucked in air as her ass was filled. This had been a fantasy of hers, ever since she had seen it on a video online. After Sally hung up, Jackie switched her phone to video mode and handed it to Jake.

"Make a movie for me," she gasped, "I want to see you fucking my ass from behind like this!"

* * *

An hour later, they lay in her bed and watched that video together. It was shaky, of course. That made it no less arousing to watch.

"God, I still can't believe that huge thing fits in my ass," Jackie sighed, stroking the cock in question with her right hand while holding her phone in her left.

At the end of the video, Jake had pulled his rampant erection out of her and stroked it, shooting his load all over her upturned bottom. One rope of the stuff had shot right into her wide-open little hole. When he had finished firing off those five impressive shots, he thrust his dick back into her ass and held it there. The camera showed half of his pulsing length as her tight asshole drained the rest of his cum.

"That was so fucking hot," she breathed. The hard dick throbbing in her hand clearly agreed with her. She looked into Jake's flushed face. "Nobody else ever gets to see this, got it?"