Blackmailing a MILF Boss

"Hey, Tasha!" Jason greeted, strolling towards where his supervisor, Tasha, was staring out over the large pool.

"Oh, hey, Jason!" she said, her eyes sparkling.

Tasha was married with kids. She'd been a supervisor at the aquatic center for quite some time. Jason couldn't help it as his eyes moved down to her busty, Ecups.

"Are you ready for a good day of lifeguarding?!" she exclaimed, almost too happily. She didn't even notice Jason was still staring directly at her chest.

"Yeah," he responded. "Did you have a good night out last night?"

"It was super," she said, flashing her white teeth.

"Sure looks like it," Jason, said, showing her his phone.

"Where did you get this? It was supposed to be private," she said, staring at the phone.

It was a photo of her in the club, flashing her bare breasts. She could barely remember the night before.

"I didn't know your husband was happy with you doing this?" Jason said, knowing very well he wouldn't approve.

"He won't be." she said, still staring at the phone. "Follow me."

Jason followed Tasha into one of the locker rooms.

"Jason, you totally can not tell him. Please." she begged. Her usual ditzy demeanor had faded a little.

"Sure," Jason said, stepping closer to her. He placed his hand on her hip, feeling the material of her one-piece swimsuit. He moved his hand down over the front of her hip, slipping his finger between the hem of the swimsuit and her inner thigh.

"Jason." she said, trailing off.

Jason could feel the bulge inside his pants growing harder. And it became very obvious after a few seconds.

"Maybe we can make a deal?" Jason said, standing on front of Tasha, placing his hands on her ass and pulling her closer. He could smell the perfume on her neck, as he pressed his erection against the front of her swimsuit.

"Like what?" she responded reluctantly.

Jason dug his fingers into her ass cheeks before pulling the back of her swimsuit to the middle and jerked it up hard, creating a mock thong. Tasha gasped. He jerked it upward again, harder this time.

"Ow," she exclaimed.

He stepped back and stared at her body. The front of her swimsuit was pulled in between her legs, outlining her pussy perfectly.

"Show me your tits," he said.

"But Jason, I'm your supervisor," she tried.

Hesitantly, she pulled the straps off her shoulders. She pulled the costume down as her massive pair of breasts bounced out. Jason stared at her large, dark round nipples. He grabbed one, feeling the ridges on her areola. He pinched her nipple, watching her face grimace a little.

"Get on your knees," Jason said.

She went down onto her knees in front of him, her breasts bouncing. Jason pulled his shorts down, allowing his bulging erection to break free. Tasha stared up at him with her dark eyes, her face an inch away from his cock. Without a word, she looked back down and wrapped her plump lips around the tip of his erection.

Tasha sucked on it. Hard. She moved her head back and forth, her lips sliding up and down the length of his veiny shaft. Jason grabbed a handful of her long, dark hair and shoved himself deep into her mouth. He shoved his cock deep down her throat as she gagged and sputtered. In and out, over and over.

Finally, he pulled her head away. Her face was soaked, saliva ran all the way down her big chest. She stood up again. Jason slapped one of her breasts hard.

"Ouch!" she exclaimed again.

He slapped the other one, watching it bounce to one side. He grabbed her nipples again, tugging at them, pulling her body towards him. They were rock-hard.

Jason walked over to the wall and grabbed a long piece of rope that was attached to one of the ring buoys. He walked over to Tasha and started binding her hands in front of her body. He grabbed the top her of swimsuit that was now on her hips, and jerked it all the way down to her feet, revealing her perfectly smooth shaven pussy lips.

"Bet you know how to use this," Jason quipped, slapping her lips. Tasha moved back a little. "Bend over this bench."

Tasha bent over a bench in the locker rooms, her bare ass in the air. Jason tied her hands and arms to the bench. He then stood behind her, and slapped her ass hard. And again. She whimpered, feeling welts forming on her cheeks, burning and stinging.

"Spread your legs," Jason said.

Tasha parted her knees as much as she could, her big tits pressed against the bench. Jason could see her moist, pink lips from behind.

At that moment, two other lifeguards walked in. One male and the other, female.

"Jason, what the fuck?" the guy said.

"You guys are just in time for the show," Jason said, going onto his knees behind Tasha, his cock long and erect as ever.

Without a word, the other lifeguards took out their phones and started recording. Jason grabbed Tasha's ass cheeks roughly, and moved his hips forward. The tip of his cock pressed against her moist pussy lips. He watched as he inched himself forward, his cock spreading her smooth lips apart. He pushed forward as his cock started stretching her tight hole. Tasha gasped, feeling Jason's thick cock opening her wide. She closed her eyes and bit down on her bottom lip. It felt like he was tearing her in half.

"You have such a tight little cunt..."

Jason could feel her tight opening squeezing his shaft as he shoved himself into her, hard and deep. Tasha let out a cry, her pussy contracting hard around his cock.

"This is good," the female lifeguard said, zooming in on Tasha's face.

Jason grabbed onto Tasha's hips, digging his fingers into her skin as he started pounding her, harder and harder. His balls slapped hard against her sensitive clitoris with each powerful thrust. Tasha moaned louder and louder, unable to move her hands. Her heart was racing. She cried out again, feeling Jason's cock ravaging her pussy.

A few minutes later, Jason pulled himself out. Tasha was soaked, her juices running down her inner thighs onto the floor. Jason moved to her face, grabbed her hair and shoved his wet cock into her mouth.

"Does your pussy taste good?" he asked, pumping his erection in and out of her mouth, her lipstick smearing all over her face.

By then, a few more lifeguards had come in, all watching or recording. Jason pulled his cock from her mouth and went behind her again. He slapped her ass hard.

He used both hands to part her cheeks as he pressed the tip of his monstrous cock against her ass. Jason grunted and groaned as he tried to slip his thick shaft into her ass.

"Come on!" he shouted with frustration.

He slid his cock between her legs, lubing his shaft up with her juices before he tried again. His fingers dug into her hips as he tried to part her tight cheeks even more. Jason started gyrating his hips back and forth with the hope that his cock would slip right in at some point. He soon realized it would require some more work.

Jason shoved two fingers into her ass, twisting them around as he tried to loosen her up. He pulled his fingers out and pressed his cock against her ass again. This time his pulsing purple tip breached her ass with little effort. A proud smile flashed across his face.

He grabbed her hips and with a loud groan moved himself forward as his thick cock slid into her tight ass. His shaft was red and his veins were bulging as a result of all the pressure. Finally, he was inside her completely.

"Fuck yeah!" he shouted in victory. It was like something from an amateur spring break porno.

He pulled himself out halfway and shoved his hips forward, forcing his cock back into her tight hole. Tasha gasped and moaned loudly as Jason increased the intensity. He started pounding her ass hard, his fingernails digging into her soft skin to keep her hips steady. He grunted and heaved, dripping with sweat as he rammed himself into her ass over and over and over.

He leaned forward and grabbed a fistful of her long hair. He tugged at it, causing Tasha to cry out.

"Take it like a whore!" he shouted, ramming her ass as he pulled on her hair.

The floor under Tasha was soaked with her juices. They were both panting uncontrollably.

Finally, Jason felt a build-up deep inside. He increased the intensity of his fucking. At that moment Tasha felt her entire body tingling. She closed her eyes as her body started shaking uncontrollably. She cried out loudly as an intense orgasm ripped through her tired body. She writhed in ecstasy as her pussy and ass contracted hard around Jason's cock. Jason pulled himself out of her ass and shoved himself into her quivering pussy. At that moment Jason erupted, filling her pussy with a long stream of hot cum. He continued fucking her, expelling every last drop deep inside her.

Moments later, he pulled his pulsating cock from her ravaged hole. One of the other male lifeguards had already shoved his cock down her throat.

"Anybody else?" Jason panted.

Two other guys came and fucked Tasha, filling her with their cum. A third guy came, fucking her tight ass until he unloaded in her too. Even the female lifeguard came, fingered her cum-filled pussy and slapped her ass a few times, before sitting in front of Tasha, making her east her pussy out until she climaxed on the bench, covering Tasha's face with her squirting.

Jason untied Tasha and she lay back on the floor, her legs wide apart, watching as the semen overflow oozed out of her pussy and ass. A last lifeguard came, putting his cock between her big tits, fucking it frantically before unloading all over her chest and face while the small crowd that had gathered cheered him on.

Afterwards, everybody left to return to their duties.

Tasha stood up, exhausted. Her legs felt like jelly. If this is what she got for being slutty on a night out, maybe she should do it more often.