Carole’s Story 07 – The New Boss

He put his hand on her thigh. “They get paid more, for doing more.” His hand came up slowly to her hip. He rested it there. She didn’t respond negatively to his touch at all. “Yeah, that’s right,” he said, moving his hand up further until he slowly ran his finger over her hard nipple. “You would be great.”

She smiled and then looked over at the Boss. “I don’t think so,” he said. “Not right now anyway.” He laughed and stood up.

“Too bad,” the man said, still holding onto her tit. “You would make a shitload of money.”

“Dinner?” the Boss asked the group.

“Sure,” was the reply.

Carole picked up her wrap and tied it around her waist before the six of them left the conference room for the restaurant. They found a big table and sat down. During the entire meal, the men stared at Carole’s naked chest and smiled. “Hard to concentrate on food, with those big things right there in front of you. Makes you hungry for milk.” Everyone laughed.

After dinner, they went over to the bar for several drinks before the Boss invited everyone up to their room. The clients readily agreed. When they were in the suite, Carole served everyone a drink. When she came up to one of the clients, he reached down and pulled the bow tie of her wrap. “No reason to cover up in here, is there?” he asked her, pulling it off her and tossing it on the bed. Then, wrapping his arounds around her and pulling her into him, he leaned down and kissed her on the mouth.

He looked over at the Boss to see his reaction. Seeing that the Boss didn’t care, the man moved his hands down to her naked ass. Grabbing hands full, he squeezed.

“I’m gonna fuck the shit out of your little whore,” the man told the Boss.

“Go ahead,” he laughed. “That’s what I have her for.” Carole saw the Boss sit down in one of the chairs. He smiled and raised his glass to her.

The man was already sucking her tits. Without his mouth leaving her nipple, the man took off his shirt and dropped his pants. Then he pushed her back onto the bed. Like the good slut she is, her legs spread automatically as the man moved up between them. He mounted her. She let out a long sigh as the man pushed his cock into her pussy.

“Oh, fuck, yeah,” the man gasp. “Nice and fucking tight.” The man used her for his own pleasure. He fucked her hard, fast, and deep. Just before he came, he reached down and pulled his cock out of her. He pointed it up her body and let to a long thick blast of cum. The hot liquid shot up her stomach and between her tits. She looked down to watch it burst and some hit her in the face. She wasn’t expecting it and she flinched. Then she just smiled, looking back up at the man.

When he rolled off her, he high-fived the next man who got on the bed with Carole. “Turn over,” the man instructed. She did. He pulled on her hips, bringing her up onto her hands and knees. He pushed his cock into her wet pussy. Carole gasped and she turned her head to look at the man. He slapped her on the ass and started fucking her.

One of the other men said, “Look at these big titties swing.” He reached in from the side and cupped on in his hand. Then the man, apparently not wanting to wait his turn, got on the top of the bed. He pushed his hard cock into her face. Instinctively, Carole sucked the cock into her mouth. The two men bounced her back and forth between them for several minutes before they both exploded in her. The man behind her grabbed her hips and held his cock deep inside her as he unloaded. The man in front of her, held her head tight. Her forehead against his stomach, his cock was all the way down her throat as he pumped his big load straight into her stomach.

When they got off her, the next and last client moved up behind her. With her still in the doggy position, the man thrust into her. Carole gasp. A couple minutes later, the man added his sperm to the collection already in her. He got up and Carole fell forward onto the bed.

As the clients got dressed, one of the men said, “I’m serious. Anytime you want to earn that extra money, you give me a call.” The men left.

The Boss moved up close to Carole’s face and whispered, “You know what’s next, don’t you?”

“Yes,” she said, looking him in the face.

“Then spread your cheeks.” The Boss dropped his pants and pulled out his stiff cock. He climbed onto the bed and on top of her. Carole let out small squeals as he butt-fucked her hard.

The next day, after lunch, the Boss took Carole to play pool in the bar. Carole was still only allowed to wear her semi-transparent wrap. “Why don’t you go get us a drink while I set up the game?” the Boss suggested.

When she didn’t come back as fast as he thought she should have, he went up to the bar to see what was going on. As he approached, he saw her standing at the bar, waiting for the drinks and talking with two men. “You here with someone?” one of the men asked her.

“Yes,” she admitted. “My Boss.” The men were both wearing speedos that were tight enough to outline their dicks. Carole noticed they were both well endowed. That made her smile.

“Oh, that’s too bad,” the man said. “I was hoping you were here with another stunningly beautiful woman.” He smiled at her.

The Boss interrupted the conversation. “What’s taking so long?” he asked.

“Oh, I’m sorry,” one of the men said to the Boss. “Just talking to her.”

“That’s okay,” the Boss replied. He looked the two men over. “Why don’t you join us? We are about to play some pool.”

The first game two men just watched. The Boss broke, but he didn’t put any in the pocket. Carole shot next. When she leaned over to shot the ball, her nipples landed firmly on the felt table top. She pocketed one of the balls. She moved around the table looking for her next shot. Then she leaned over right in front of the two other men.

The Boss leaned into the one of them and said, “Nice ass, huh?”

“God, yes,” the man said.

Carole heard them both, of course, but just shot the ball. She pocketed another. She moved to the other side of the table. Again, the men watched as she dragged her tits across the felt.

“So, she is your secretary?” one guy asked the Boss.

“Yeah,” he said. “With benefits,” he laughed.

“I can see that,” the man said, with a smile. “She’s married?”

“Yeah, he doesn’t mind.”

“He knows?” the man said with some surprise.

“Oh, yeah,” the Boss confirmed. “She even works as a whore every now and then.”


“Yup,” the Boss said, as Carole moved back around to their side of the table. “I usually just use her for fun on these trips.” When Carole was in front of the Boss, he pulled her over to him and kissed her. At the same time, he pulled the knot free on her wrap. He took it from her, leaving her naked in front of everyone. “Go ahead,” he told her slapping her on the naked ass. “It’s still your shot.”

She leaned over, her ass and pussy right in front of them. What a magnificent sight. “Wait a second,” the Boss told her. “Freeze.” She stopped, but didn’t stand back up. She turned and looked at him.

“I’m getting tired of you dragging your tits all across the table.” He turned to one of the men. “Can you help?” The man jumped up. “Put your hands under them and keep them off the table for me,” the Boss told him, with a big grin.

The man got a huge smile on his face as he pushed his hands, palm up, under her big tits. “This okay?” he asked the Boss.

“Better.” The Boss smiled at Carole.

Carole, now distracted by the man groping her tits, missed the next shot.

The Boss missed his shot, on purpose.

The man followed Carole around the table. When she leaned over for her next shot, the man stood directly behind her and reached down on both sides and picked her tits up off the table. The position put his crotch on her ass. He pushed his cock against her ass. Carole felt the man’s cock harden and move. It straightened up and moved right into the crack of her ass.

Carole missed the shot. As she stood, the man didn’t move. Instead his hands came down her sides and grabbed on to her hips. The man thrust a couple of times, dry-humping her. 

The Boss laughed and then took to the game and cleared the table. “Hey,” he said. “Why don’t we go to my room. Drinks are cheaper there.” He smiled. Carole knew what he had in mind.

“Sure,” both the other men agreed happily.

Half-hour later, Carole was airtight. The Boss was down her throat with the other men in her ass and pussy. The fucking continued until all three had cum inside her, then they got up off the bed, leaving her in a puddle of sweat and cum.

The men all stood around and drank, staring at her naked body. “Anyone for a second go?” the Boss asked after a while.

“Fuck, yes,” one of the men said, jumping to the chance. He climbed on top of her. He pushed her legs apart with his and shoved his cock into her pussy. Carole groaned.

The man fucked her fast and furious. Carole held on to the headboard, as he rammed his long hard cock into her. Just as he was about to cum, he pulled out of her and shot his load up onto her stomach.

The next man climbed on and took the first man’s place. This man was slower, but fucked her just as hard. Carole moaned loudly as she took the man’s cock. He didn’t pull out when he came. Instead, he unloaded inside her, refilling her wet pussy. The man got up when he was done.

“Well, don’t just leave them standing there,” the Boss told Carole. “Clean them up so they can go.”

Carole knew what that meant. She got up off the bed and got to her knees. She sucked the two men clean before they put their speedos back on and left the room. The Boss shook their hands as they left and closed the door.

A minute later, Carole was standing, bent over the small table, as the Boss forcefully rammed his cock into her ass.

After dinner, the Boss took her to the club. He danced with her and let other men dance with her. Naked, Carole was openly groped by the men as they danced with her.

An hour or so after they arrived, the Boss sent Carole to the bar to get another round of drinks. She picked up the two glasses and turned around. When she did, she ran right into a very small man. The man was tiny. Carole, at five foot four, towered over him. He couldn’t have been much over four feet tall. Carole was shocked. The Little Man, however, had conveniently maneuvered himself so that his face was directly between her large soft tits.

Embarrassed and surprised, Carole tried to backup, but the bar was right behind her and the Midget kept pushing forward. “I’m sorry,” she said, still trying to maneuver herself out of the situation.

The Midget, still keeping his head between her tits, looked up at her face and said, “Don’t worry about it. I don’t mind at all.” He smiled widely. “As a matter of fact,” he turned his head to one side and kissed her breast, “I think I should thank you.”

Carole nervously smiled down at him and turned to get away from him. For a second, she stared at the Midget. He was perfectly proportioned, only small. She did notice, though, that the bulge in his shorts was a nice size. She walked back to the table where the Boss was waiting. She didn’t notice, but the Midget followed her. Boss, however, did see the man. When the Midget saw that she was going to a table with a man, he got a disappointed look on his face and started to turn around. The Boss, however, waved him over.

The Boss was just as surprised as Carole was at the size of the Midget, but the Boss was a lot more devious. “Would you like to join us?” he asked the Midget.

“Thank you,” the Midget said. “Don’t mean to interrupt, I just ran into your girl at the bar and I thought I might, well...get to know her better,” he grinned.

“I bet,” the Boss laughed. A man walked up to the table and asked if he could dance with Carole. The Boss agreed and sent them off to the dance floor. The Boss and the Midget watched the couple dance. “She’s got a great body, doesn’t she?”

“God, yes,” the Midget said in agreement. “Your wife is beautiful.”

“Oh, she’s not my wife,” the Boss. “I am her Boss. Her husband lets me bring her on trips like this.”

“He knows about this?” the Midget asked. The Boss nodded. “Nice guy,” the Midget said with a smile. “She does have some really nice tits. I would need some mountain climbing gear to get up them,” he laughed.

“You wanna try?” the Boss asked the small man.

“Fuck, yeah, I do.”

As soon as the song ended, Carole left the man at the dance floor and returned to the table. The two men stood. “Come on,” the Boss said. “We are leaving.”

Carole saw that they were going back to their room and the Midget was going with them. She knew what that meant and she was not excited about it, at all. As they walked, the Midget took her hand. The Boss opened the door and let the three of them into the room. As soon as the door was shut, the Midget dropped his shorts and pushed Carole onto the bed. He climbed on with her.

He pushed her down onto her back and started kissing her. Carole kissed the small man back. The Midget’s little hands went immediately to her big soft tits. For several minutes, with the Boss watching, the Midget kissed and groped her.

Finally, the Midget broke free. He moved up the bed, bringing her dick up to her face. He sat back against the wall and watched as Carole rolled over and took his hard cock in her mouth. Carole was happy to see that, while it looked huge on him, it was at least average sized. “Oh, fuck yeah, baby” the Midget moaned as she took his entire shaft down her throat with ease. “Suck that cock...”

After a while, the Midget pushed her off his cock and back onto her back. He scooted down the bed and rolled over on top of her. He mounted her. Carole let out a small groan as the man’s cock pushed up into her pussy. Because of his size, the Midget’s mouth was right on top of her tit. He sucked a nipple into his mouth as he fucked her.

Lasting longer than Carole thought he could, the Midget eventually pulled out of her and turned her over. Carole came up on her hands and knees and the Midget moved up behind her. Standing, he forcefully rammed his cock back into her. He grabbed onto her hips and rode her.

It didn’t take him long in this position to started to cum. He groaned loudly as he shot his hot cum up into her. Spent, he pulled his limp cock out of her and sat down at the head of the bed. The Midget watched in awe, as Carole took his wet cock back into her mouth and sucked the remaining cum out of the shaft.

It was then that the Boss climbed onto the bed. He pushed he face down on the mattress and then looked up at the Midget. “Watch this,” he said with an evil grin. “Carole,” he instructed, “look up into his face.” Carole lifted her head as best she could and looked at the small man.

The Midget watched Carole’s expression as the Boss slowly, but forcefully, pushed his big hard cock into her ass. “Oh, fuck, yeah,” he said. “Take it up the ass, you slut...Fuck.”

He watched as the Boss fucked her ass hard until he came deep inside her. The Boss rolled off her, leaving her sweaty and panting on the bed, cum leaking out of both holes.

“Go clean up,” the Boss told her. She went into the bathroom. “The whore is something else, isn’t she?”

“Damn right she is,” the Midget agreed.

“Why don’t you take her with you for the night,” the Boss said. “Just bring her back in the morning.”


“Yeah, sure,” the Boss told him. “She is yours for the night.”

“Wow, thanks,” the Midget said, shanking the Boss’s hand. Carole came out just at that moment. “Come on,” the Midget said, taking her hand. “Let’s go.”

“What? Wait...” Carole started.

“Do what he tells you to do,” the Boss said, disappearing into the bathroom. 

The Midget walked her back to the club. For almost an hour, the danced and drank. As they danced, the Midget’s face was always between or on her big tits. The rest of the people on the dance floor watched and smiled.

As the Midget led her of the dance floor, he made her lean down to him and he whispered, “I need a blowjob. Follow me.” He took her by the hand and led her into the men’s bathroom. There were other men in the bathroom, when they entered, but the Midget just led her right by them and into a stall.

Leaving the stall door wide open, the Midget climbed up onto the toilet. Standing on the toilet, he pulled Carole’s head down to his crotch. “Suck me, you fucking slut,” he told her. She took his cock into her mouth. The other men in the bathroom walked over to the stall so they could watch.

In front of the growing audience, Carole sucked him dry a couple minutes later. Standing back up and wiping her chin, she turned around to see all the horny hard dicks in front of her. The first man put his hand on her shoulder and pulled her head down to his throbbing erection. Carole sucked off and drank the cum of four men before the Midget dragged her out of the bathroom and headed for his room.

Once in the Midget’s hotel room, she went into the bathroom to clean up. While she was in there, the Midget got out his video camera and set it up. He videoed Carole as she came out of the bathroom and got on the bed. Then he put it on a tripod and climbed on the bed with her.

The first thing the Midget did was turn her over onto her stomach and fuck her in the ass. After some recovery time, he fucked her again in the pussy, before ending the night with a blowjob and cumshot all over her face.

The next morning, he made her suck him off again before he took her back to the Boss.

The Boss let her back in the room. “How was your night?” he asked, laughing at her.

“Fine,” she said, looking down at the floor.

The Boss kissed her and then turned her around. He bent her. She squealed.

The Boss brought her home the next day. I had her recount the story in detail and then I made her suck my cock. All was right with the world.
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