In Times of Need

Without saying a word, Paige reached out, grasped him and guided him in. She was so well lubricated by now that he slid in with little effort. She felt herself getting fatigued from all the action, so much so that she no longer seemed to care that it was her son inside her.

Kevin paused and enjoyed the feeling of his mother's cunt holding him in a tight grip. He felt her begin to rock gently under him, as if urging him on. He put one hand on her buttcheek and gave it a playful squeeze. It felt smooth and firm in his grasp. Not wasting any more time, he began pumping at her. Gently at first, speeding up steadily. He heard her breathing quicken to match his pace. She began meeting his thrusts, pushing her ass back into him. He put both of his palms on her buttcheeks and spread them lightly. Looking down, he saw her small butthole. It seemed to be winking at him invitingly.

Skipper appeared at his side, which made Kevin feel uncomfortable at once.

"There it is," said Skipper, angling his hand-held camera to get a view of Paige's asshole. "Let's get her ready. Start probing it with your fingers," he instructed. "Massage it. Get it used to something touching it. Then start digging your finger inside. Little by little. Here, use plenty of lube. It will help. Just don't rush it. Once you get one finger in there, try to work another one in. Assholes are very flexible, they are just temperamental."

Kevin's eyes were glued to his mom's anus. He's often wondered what anal sex might feel like. And now, he could barely wait to find out.

"Paige," Skipper continued, "you should try your best to relax your ass. Breathe deep and think of something pleasant."

She didn't answer, but spread her legs further apart.

Kevin slid a thumb down and placed it lightly over her puckered hole. He kept it there for a few moments, seeing how his mother would react. She didn't seem to care. He began kneading it, slowly spreading it this way and that.

"Use more lube," said Skipper and squeezed more lube right into her crack.

"Hey!" Paige exclaimed, clenching her ass as the cold fluid ran down her skin.

"It'll make things easier," explained Skipper and backed away.

Kevin rubbed the lube onto his fingers and over her anus. He felt her relaxing again. Using his index finger, he began probing the opening. It didn't yield at first. He went back to massaging it, then tried to stick the tip of his finger in. He put some force into it and felt the tip of his finger slide in. He just held it there as he continued pumping her from behind. Just barely, but his finger began sliding in and out of her ass, each time going in a little deeper. He was up to his second joint inside of her, when he decided to try and add another finger. His middle finger began rubbing the rim of her anus, looking for a way inside. It was more difficult than he thought. Her asshole was tightly wrapped over his one finger. He began wiggling it around to create some space. Little by little, his second finger was making its way in.

Kevin noticed that he wasn't pumping her anymore, concentrating on fingering her ass. Instead, she was rocking back into him, doing all the work. Two of his fingers were inside of her now, much thanks to the lube. Her ass seemed to be clutching at his fingers, and yet he kept working them. Sliding them in and out, he tried to spread them apart to make her opening wider. He could smell the aroma of lube and anus, and it seemed so very arousing to him.

"Okay, that looks good," announced Skipper. "I think it's time to try your cock."

Kevin nodded and pulled out of her pussy. He kept his fingers inside of her ass, though, as if afraid that it might close forever.

"I know you are well lubed," said Skipper. "But more can never hurt." He squeezed more lube onto Paige's ass.

Paige turned her head to look back behind her. What a strange sight she saw - a camera pointed at her, and her son lubing up his hard cock behind her, keeping two of his fingers inside her ass. She wanted to laugh hysterically, realizing how unreal this all seemed. It didn't help that his probing of her ass tickled her to no end.

"Go very slow," she warned, looking at her son's cock. "Very easy."

Kevin nodded and prepared to enter her anus.

"Get down on your elbows, Paige," Skipper instructed. "Stick up your ass and relax."

"Easy for you to say," Paige grumbled. "If it starts to hurt, we stop."

"Yes, yes," Skipper agreed. "Of course. We're just going to try."

Paige took a deep breath and lowered herself to her elbows. Putting her head on the pillow, she spread her legs a bit further and tried to relax even more.

Slowly, Kevin pulled his fingers out. As soon as he did, her anus closed shut. Quickly, he brought his cock down and pressed his tip to her dark rim. He pushed with his hips.

Paige's eyes grew wide as she felt the rising pressure on her anus. Where before, his fingers felt ticklish at best and uncomfortable at worst, this was entirely different. It felt like a ram was trying to enter her from behind. She bit down on her lip, to keep from crying out.

"Spread her ass with your hands," she heard Skipper say. She was amazed to feel something thick and slimy begin to slide into her anus. She let out a small groan as the tip of his cock made its way inside. The pressure on her anus eased, but was replaced with an odd feeling. It wasn't painful, but it felt out of place. His cock was slowly sliding deeper and deeper inside.

"Easy," Paige purred a reminder. She wondered how deep he would go, how far she could take him. Surely that whole thing could not fit inside of her. And yet, it didn't seem to stop its advance. Her lips were pressed tightly and she realized she was tensing. She took a deep breath and tried to relax again. Finally, she felt him stop. Her ass felt stuffed, and yet there was something satisfying about it. They spent a few long moments, neither of them willing to move.

Kevin stared down at the sight of his cock buried deep in his mother's little ass. He was afraid that he was hurting her, and yet, he felt a powerful urge to pump away at her. He pulled his hips slightly back and noticed how tight her anus held his shaft. If it wasn't for the lube, he guessed they might be stuck like that. Nevertheless, his cock began to glide slowly out. He watched with intense curiosity, but any fears he might have had were put to rest. He paused about halfway out and pushed back inside of her.

"Oof!" Paige quietly let out.

Kevin began to softly pump at her.

"Reach around, down to her clit and rub it," instructed Skipper, his camera floating near by.

Kevin complied. He didn't really know what or how he should be rubbing it, so he cupped her mound with his palm and massaged it back and forth.

Despite herself, Paige began whimpering softly. The feeling of a cock in her ass while her clit was stimulated sent her senses into overload. She felt light-headed and was losing control. Such sexual pleasure was beyond anything she'd ever experienced. She felt her body begin to quiver, and she wondered how much longer she could take this. Strangely enough, she actually wanted to find out.

Paige almost didn't realize what was happening to her, it had been so long. She felt tingling up and down her anus and her pussy. The sensation spread all the way down her legs and up her spine. A ball of tension was building somewhere deep in her belly, like she was going down a rollercoaster. Her clit was the center of bliss while it was getting furiously rubbed. She almost forgot that there was something going in and out of her ass. Almost. She felt her heart begin to pound in her ears. She shut her eyes and buried her face in the pillow. It felt like something exploded inside of her and shot electrical currents across her entire body. She cried out into the pillow as her body jerked involuntarily. She clenched her ass hard and her legs shook. She clutched tight at the sheets and let herself go.

Kevin and Skipper both watched her wreathe in ecstasy. They heard her muffled cries, as orgasm washed over her body. She squirmed under him as he held her by the hips, his cock inside of her ass. He felt how her entire anal canal trembled around his shaft. The fact that he caused his mother to orgasm, made him even more aroused. With renewed energy, blood flooded into his cock. He felt like he would cum at any moment.

Paige's orgasm finally began to settle and she sagged onto the bed. She was becoming aware of her surroundings once again.

"I'm about to cum," she heard Kevin say.

"Good," said Skipper. "Let me swing around to get a good view of the cumshot. Paige, how are you doing?"

She lifted her head and gave a ragged sigh. "Fine." She felt her son's cock begin to slide out of her ass. She seemed to both spurn and welcome the feeling. When he pulled out of her, she suddenly felt exhausted.

"It's almost over," Skipper tried to encourage. "Kevin is ready to cum. Are you ready for the cumshot?"

She gave a small, tired nod. Her eyes were half closed and her head spun.

"Great! Okay, sit up."

Slowly, she complied. She saw Kevin standing above her, sweat rolling down his forehead and cheeks. His his manhood was before her, in all of its glory. Nevermind that it was just in her ass, she wanted to reward him. Smiling, she looked up at him. "You did great, Kev."

He smiled back in response.

"Are you ready?" she asked her son.

He nodded.

Her eyes dropped to his cock. She reached out for it and pulled him closer. She moved her face up to it and hesitated. It was oily to the touch and smelled like lube with a hint of fragrance.

"Go ahead," she murmured and began stroking him. "Let it go."

Kevin watched his mom's hand move up and down his shaft. His oversexed tip was mere inches from her face. He thought that he could feel the heat of her breath on it.

"Relax," Paige went on. "Release."

Kevin groaned. "Here I come!"

"Quick!" urged Skipper. "Make sure he shoots inside your mouth."

Paige felt her son's cock expand in her hand. Leaning in, she opened her mouth and closed her eyes. She heard him grunt as he began ejaculating. He shot his first, huge load across her chin, into her mouth, and into her throat. She didn't have time to swallow as he released again and again. She opened her eyes and looked up at him. His eyes were glazed over and he was breathing heavily. His spunk seemed to fill her entire mouth. She could never have guessed that there could be so much of it. She could taste its saltiness on her tongue. She looked back down, and gave his cock a squeeze, forcing a few drops fall to the floor.

"Magnificent!" Skipper broke the moment. "Paige make sure to swallow it all."

Paige glanced over at him. He was at the viewfinder of the main camera. She felt in the spotlight. She was performing. Closing her mouth, she tilted her head back. She didn't mind the taste of it, but its texture was stringy and not easy to swallow. It took her several tries to get all of it down. She used the back of her hand to wipe the rest off of her lips and chin.

"That's it," she said plainly.

Skipper grinned at her merrily. He pulled out an envelope and laid it on the bed. "Twenty thousand, as we agreed. I hope it was worth it."

Sighing she looked at her son - his cock was beginning to deflate. "I hope so too."