Lucky Pt. 02 Ep. 06

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The Dirty Dirty Boy.
4.2k words
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Part 21 of the 27 part series

Updated 06/08/2023
Created 11/25/2017
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The Dirty Dirty Boy

"I think I'm going to love it at the new firm," Cheryl said through heavy breaths as she bounced up and down on Lucky's cock.

She had jumped him as soon as she entered the apartment. She had a wild look in her eyes and couldn't wait to feel him inside of her, or at least that's what she had said to him as she began undressing as soon as she closed the door behind her.

Lucky lied on his back on the bed as he watched her breasts bounce in the moonlight. Her pussy pulsating around his dick as he rubbed the tops of her thighs.

"My new assistant is really nice too," she continued as she leaned forward and began grinding her hips back and forth, rubbing her clit against the backside of his shaft. "I'm still not used to having a personal assistant, to be honest."

Lucky reached around her backside and pressed the tip of his finger into her asshole as she continued grinding her hips on him. She cried out in pleasure, but otherwise continued the same pattern of grinds.

"It's also strange that I don't have a boss," she breathed heavily, her face pressed almost against his. "I am the boss."

Lucky hooked his finger further into her asshole and pulled her closer to him as he looked into her eyes.

"At work," she started in a long gasp. "I'm the boss at work."

He smiled at her. He wasn't trying to get her to take a submissive role in the bed, but he would take it if she was willing to give it up. She cried out as he thrust his hips forward and pressed his lips to her neck before giving her a playful nibble.

"I have the power to fire people," she started to say but was cut off by another thrust of Lucky's hips and hook of his finger.

"I feel like I made the..." she started to say something, but was cut off as he felt her pussy tighten around his cock. "I'm cumming!"

She threw her body down on his chest and jerked about as he continued to thrust his hips forward over and over again. She cried into his chest as he grabbed her hips and worked her up and down on his throbbing cock.

She wanted him, but he wanted her just as bad. He had grown used to her. He had grown used to her smells, sounds, touches and couldn't imagine going a day without her. Her warmth felt amazing as it pumped around him. Her hot breath spreading over his chest as he pounding his cock into her over and over created a mix of erotic desires that he couldn't overcome. He knew that his orgasm was approaching.

His balls tightened and dick swelled, giving him the signs of an upcoming blast of his cum. She could feel it too and screamed for him to cum inside her.

He slammed her down on him one last time and shot load after load of his cum into her womb as she screamed in acceptance.

Once finished, Lucky released her hips. She lied on top of him with his dick deflating inside of her for a few minutes as she caught her breath before rolling off of him and stepping out of the bed. She made her way to the bathroom and he heard the shower turn on.

"I'm really glad you like your new job," he said as he sat up on the bed and pulled his underwear back on. "I told you."

"You were right Lucky," she said from the shower. A mist began billowing from the open door. "How was your day?"

"It was good," he said thinking about Toshiko and Lois.

"What'd you do?" she asked.

"Just sat around mostly," he answered and to be honest it was the truth. Having sex with Toshiko was only a portion of the day he had without Cheryl. After he had returned to the apartment, he had picked up the book that he had been reading and got a few more chapters done.

The conversation went as normal as he would have expected. Cheryl asking him little questions here and there and Lucky asking her questions about her new job. She finally got out of the shower and crawled into bed wearing one of Lucky's t-shirts. His shirt looked like a gown on her.

Within a few minutes, Cheryl was deeply asleep, exhausted from her first day on the job. Lucky lied next to her and stared at the ceiling for awhile until he realized that he wouldn't be able to fall asleep that easily. He quietly stood up from the bed and tiptoed out the bedroom door, closing it behind him. He sat down on the couch and picked the book up once more.

Addison rushed to his head once more before he was able to open the book. He could almost see her face as she smiled at him. He could remember the smell of her burnt eggs as she tried to cook him breakfast in the mornings. Her corny jokes as they walked through the forest around her cabin. He remembered her bright brown eyes as she would look into his and tell him things that made his heart flutter.

Shaking his head as if the thoughts would release, Lucky angrily opened the book and began reading.

It was a book about a world where magic and elves ran through fighting other creatures in great battles. Something about the fantasy of the world drew him in more than any other book he had read had been able to do. It helped rid his thoughts of Addison if only for a moment. He was in a section where a dragon was terrorizing a small village and the group had to get together and find a way to fight it. He didn't know how it would be possible for such a small group of elves to fight off a large dragon that could devour an entire village within minutes, but he had faith in them.

A soft knocking on the door had Lucky placing the book back down next to the couch and walking over to see who was knocking. He opened the door to find Lois and Toshiko standing together and smiling at him.

"Is Cheryl asleep?" Lois asked in a whisper so soft that Lucky had to strain to hear it.

"She just fell asleep a few minutes ago," he answered. "Everything okay?"

"You wanna come over?" Lois asked with a look that told Lucky everything that he needed to know. She was wanting some more of what she had received in the morning. She had more time this time though. He looked to Toshiko and must have had a questioning look on his face because she spoke next.

"We've been talking and would like to include you in the conversation," Toshiko explained with a shy smile. She was so small that Lucky had to look down to look her in the eyes.

"Sounds fun," he said with a smile as he followed them across the hall to Lois's apartment.

Once he stepped inside behind them, he closed the door and watched as they continued to walk toward the bedroom in the back, beckoning him with curved fingers.

He followed them into the bedroom, but they didn't stop at the bed. They stepped into the master bathroom where Lucky noticed for the first time that Lois had a large jacuzzi put in to replace the shower that Cheryl still had.

The jacuzzi was already full of steaming hot water and the jets were already on.

Lucky watched as Lois gripped the bottom of Toshiko's shirt and pulled it over her head, revealing her small but firm breasts. Her nipples were sticking out from the cool room air touching them and the steam coming from just beside her off of the water. Lois slowly ran her hands down Toshiko's chest and stomach to grip the waistline of her shorts before pulling them down and revealing her firm ass and shaved pussy. Goosebumps ran up and down the small Asian woman's arms and legs as she looked over to lucky with a wide-eyed expression.

Toshiko turned to stare at Lois, who was still dressed in her business clothes. She worked her slender fingers over the buttons of Lois's blouse as she slowly revealed the blonde's large breasts, covered by a black bra. She pulled the blouse untucked and pushed it off of her shoulders and arms before reaching around her back and unfastening her bra to allow it to drop to the floor. Lois's nipples were erect as well and her large breasts seemed to defy gravity as they did not slump in the slightest. Toshiko dropped to one knee as she released the button of Lois's trousers and pulled them, along with her panties to the floor to reveal a fully nude Lois for Lucky to take in.

Both women stood in front of him in the nude and looked over to him before calling him over. He stepped toward them and Toshiko sat down on the side of the jacuzzi as Lois walked around behind him. The small Asian woman pulled his pants and underwear down slowly, following the fabric with her lips to his skin as she pulled them down. Lois reached around him and pulled his shirt up over his head.

Lois began kissing his back as her hands slid down his stomach toward his cock. Toshiko slid her hands up the back of his legs as her head moved back up. She pressed her face so close to the side of his cock that he could feel her warm breath wash over it as Lois's hands slid closer.

He looked down to see Lois grip his shaft in her hands and Toshiko rolled her head over until her lips were pressed against the soft back of his dick as she looked up to him with her large and dark eyes.

"Toshiko wants to feel your dick in her ass," Lois whispered in his ear as her hands gripped him tightly.

Toshiko opened her mouth as Lois's hands pulled his dick down until it was aimed directly at her lips. She pushed her head forward and Lucky let out a slight moan to the sudden warmth of the small Asian woman's mouth around his cock.

Lois's hot breath followed every kiss on his back as her hands gripped the very cock that Toshiko was sucking on. Small wet kissing sounds made their way to his ears, driving him crazy.

Finally, Lois released his cock and Toshiko pulled her head back at the same time. Toshiko slid backward from the rim of the tub and into the water with her feet still sticking about of the water as Lois stepped around and stepped into the water before lowering her body in until she was sitting chest deep in the water.

"Come on in," Lois purred. "You need a bath, you dirty boy."

Lucky didn't need any more prompting than that. He stepped into the water, slowing his movements when he felt how hot the water was. It was a lot hotter than he had anticipated. He slowly lowered himself until he was sitting between the two beautiful women.

Lois pushed herself against his side, rubbing her large breasts against his arm.

"She's a little nervous about the anal thing," Lois whispered in his ear as she rubbed her fingers up and down his shaft from underneath the hot water. "You might need to start things for her."

Lucky looked at the tiny woman, her feet still sticking out of the water. Her tiny frame seeming even smaller in the water. He brushed his hands up her back, causing her to startle and jump a bit. She looked at him and gave an embarrassed chuckle.

"Maybe you should start by showing her how to take it," Lucky suggested toward Lois, who looked at him with a broad smile and widened eyes.

"Are you going to stick your dick in my ass?" Lois said loudly enough to bring Toshiko out of her trance. The small woman turned to regard Lois, who was smiling at her.

Lois rose enough to drift her body over one of Lucky's legs and pulled her hips back until she could feel the head of his dick slide down her crack until it pressed against her closed asshole. She stopped for a slight moment as she appeared to be bracing herself for the intrusion, but it didn't take long for her to start lowering her body.

He felt the head of his cock press roughly against her asshole as it resistant him for a brief moment. Finally, he felt her ass open slightly enough to accept a part of his tip. She moaned as she lowered herself a bit more and a bit more until he could feel half of his throbbing cock in her asshole.

"It feels so good Toshiko," Lois moaned as she looked over at her friend.

Toshiko was watching with an intense expression on her face. Lucky watched her as she watched Lois lower herself further down on his rod.

It didn't take long for Lucky to feel Lois's asscheeks pressed firmly on his hips as his entire dick sat inside of her asshole. She leaned forward and gripped the side of the tub as she moved her hips back up a bit. He stroked her back as she rose and lowered her body to him at her own comfort level.

She began to move a bit faster, with deeper ups and lower lows until her moans had shifted into screams. He felt her hole tighten around him. He could feel her heartbeat around him. He could feel her asshole open and close on him as if it were trying to eat his cock. Water splashed along the walls of the tub as her body began jerking this way and that in throws of an orgasm.

Once she settled, Lois rose off of his cock and sat back in the waters next to him as she caught her breath and smiled at Toshiko.

"I'll be gentle," Lucky offered the timid Asian woman.

She smiled at him as she lifted her ass out of the water to step over his leg the same as Lois had done. He watched her tiny ass hover over his face as she lowered it into the water over his hungry cock.

He gripped the base of his cock with one hand and guided her ass by the hip with the other as she slowly lowered herself into the waters just above. He felt her tight asshole press down against the tip of his throbbing cock and she stopped.

She gripped the rim of the tub and was frozen solid.

"We don't have to do this," he offered as he stroked the side of her asscheek.

"No," she whispered. "I need your help though."

Lucky looked at Lois, who smiled and nodded before rising to her knees in the water and placing her hands on the woman's back. He could feel the pressure of her asshole grow a bit more as Lois pushed down. He could feel Toshiko's ass open up slowly and slightly as the end of his head began to push its way in.

"Slow down," Toshiko begged with a sharp gasp.

Lois tried to adjust herself, but her knees slipped, causing the woman to fall onto Toshiko's back, pushing her hips down with all the force of her falling body weight.

Lucky's eyes went wide, Toshiko screamed and Lois gasped as he felt his entire dick penetrate the tiny woman's asshole in one quick and rough motion.

Toshiko sat frozen on his cock with her back thrown straight back and her face aiming for the ceiling like a wolf howling in the night. Her screams subsided into whimpers as Lucky felt her tight asshole pulsating in protest around him. He didn't know what to do. He didn't know how to make it better.

"What the hell," Toshiko gasped in quick breaths.

"I'm so sorry," Lois said in a panic. "I slipped. I'm so sorry."

The tiny Asian began to relax a bit as her pain slipped away and seemed to be replaced by pleasure, for her hips began to sway back and forth ever-so-slightly.

Her cries of pain were soon replaced by moans of lust as she continued her motions, Her face remained facing the ceiling. Lois, seeming to notice the change in mood as well, slid her hand down in front of the tiny woman and began fingering her as she shifted back and forth on his cock.

He could feel her ass loosen up as she moved and moaned. Her body wiggled and shook from time to time as she felt an orgasm approaching. Her moans grew a bit louder as she began to grind her hips at a quicker pace.

He slid his hands up her tight stomach and cupped them over her breasts as she began to slightly bounce on him. She didn't bounce enough for his cock to slide up and down, but enough so that her asshole seemed to be jerking him off.

"I'm cumming," she announced as her body jolted violently, splashing water over the rim of the tub.

Lois worked her fingers quickly as Toshiko rode her orgasm out until she eventually stopped and lied back against Lucky.

"Thank you," the small woman breathed as her chest moved deeply in and out. "Finish with me however you want."

"Are you sure?" Lucky asked. He wasn't sure that Toshiko knew what she was telling him to do.

"Use me Lucky," she breathed. "You've earned it."

Hearing what he needed to hear, Lucky pressed his hand over the woman's back and shoved her down until her stomach was pressed against the edge of the tub and she was holding herself up by pressing her open hands to the bathroom floor.

He pulled his dick slightly out of her asshole before slamming it back in, bringing a shout from straight from her lungs. She screamed louder and louder as he began to pump his cock into her ass as hard and fast as he could.

Lois eyed him in shock and awe as he worked his way in and out of the woman's asshole. He placed his hand on her back as well and pushed her over the tub until both women were bent over and holding themselves up in the same fashion.

He pulled his cock out of the tiny woman's asshole so fast that it made a popping sound before shifting over until he was behind Lois. He gripped his cock in his hand and shoved it into her asshole as hard and fast as he could.

Lois screamed a low and guttural scream as his cock filled her ass completely, spreading her wide. He worked himself in and out of her over and over as she screamed in a mixture of pain and pleasure. After a few minutes, he pulled out of her and shoved his cock into Toshiko's ass once again, drawing another series of screams.

He continued this for as long as he could. He worked one woman's ass until he decided to move on to the next. Eventually, the feeling of his climax was taking over and he knew he wouldn't be able to hold back much longer.

He pulled his cock out of the last woman's asshole and gripped his throbbing dick as he shot blasts of his hot cum over each woman's backs until he wiped the last droplets of cum from the tip of his dick against Toshiko's open asshole.

He grabbed each woman with a hand on the shoulder and pulled them back into the water as they each pressed their backs against the walls of the tub and eyed him in awe.

At first, he thought he had made a mistake. She said to use her however he wanted, but maybe she didn't know what he would do. Maybe he had messed up.

"That was amazing," Toshiko finally said in a whisper. "Unexpected, but amazing."

"Told you," Lois said with a self-assured tone to her voice.

"Thank you," was all that Lucky could think to say. He quite knew how to respond to women when it came to compliments, but a thank you always seemed to go a long way.

"No," Lois said as she leaned over and kissed him on the side of the face. "Thank you."

"Yeah," Toshiko said as she leaned over and kissed the other side of his face. "We have to do that again sometime." A grimace of pain shot over her face before she added, "but not tonight."

Within a few minutes, Lucky had dressed and stepped back across the hall to find Cheryl in her deep sleep on the bed. He smiled as he looked down at her. She lied on the bed sprawled out with her legs spread wide and his shirt pulled up above her navel, revealing her white silk panties. Her mouth wide open as she breathed in heavy breaths before releasing in a long and low hum.

He slid his fingers up her legs and stopped at the waistline of her panties before looking down to see that his dick was already growing again.

He didn't know what was happening to him, but he felt a need to have sex with her right then and there. She slapped her lips together as she rolled her head around a bit before settling into her normal deep sleep.

He looked down once more and seen that he already had his pants down on the floor and his cock was in his hand. Even though he was shocked by his instinctive actions without a single outward thought, Lucky began stroking his cock as he stared at his master's face. He ran his gaze down her neck and chest. He stopped as he stared at the muscles in her stomach move to her heavy breaths before moving down to her white panties. Her legs spread out and her toes curled up as she slept.

He continued to stroke as he pulled her panties down, gently enough to not wake her, and left them hanging off of one foot as he slid his fingers back up to her slit. She stirred in her sleep a bit as his fingers pushed inside of her pussy, feeling her warmth around his digits as he stroked his cock.

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