Ms. Wittmore Pt. 04: Challenges

"You never fail to impress me Cally, I wish we had more time to continue this fun but alas you need to get out into the bar and earn your keep and I have some calls to make."

Removing her fingers and pulling Cally up off the table, Ms. Wittmore gave her one more sharp slap on the ass and sent to her shower room to get ready for the evening ahead.

As soon as Cally left the room Ms. Wittmore picked up the office phone and dialled through to the bar.

"Seb!"

"Yes Ms. Wittmore?"

"I have a plan, the perfect plan, as soon as you see Cally in the bar come through to my office and I will explain what is going to be required."

"Of course Ms. Wittmore," Seb replied.

Cally didn't see Seb slip through to Ms. Wittmore's office, she didn't hear the conversation between them, in fact she was oblivious to the plan Ms. Wittmore and Seb were now putting in place. Nor was she aware of the part she was to play in their plans in the coming hours and days, she just went about her evening as normal, moving amongst the regular guests, laughing at their jokes, avoiding their roaming hands and making sure their tables were served and the drinks were flowing freely.

As Ms. Wittmore finally made an appearance that evening, she first stood at the sidelines and watched Cally at work. She watched as she worked the room, greeting guests, it all seemed so natural to her these days and Ms. Wittmore couldn't help but smile to herself at how confident Cally was. As she made her way slowly towards Cally, she too greeted guests and chatted idly all the time her eyes never left the girl now just almost in reaching distance.

Finally she was stood behind Cally and wrapped her arms around her waist, she felt the way she automatically tensed and then the way she relaxed and leaned back against her when she whispered her greeting into her ear.

"How's my slut doing this evening?"

"Good Ms. Wittmore and even better now," Cally replied as she felt Ms. Wittmore's hand slide down her body.

Ms. Wittmore no longer hid what was between herself and Cally, in fact she made a point to make it very clear to all in the club that Cally was hers and these public shows of affectionate or more accurately dominant displays were quite the norm. But she also still liked to test Cally, push her beyond her limits, its what gave her the greatest pleasure, that and to see the daily struggle with the girl. She never grew tried of Cally, it was almost like getting to break her again everyday and she never failed to please. However the next test she had for Cally would be the toughest yet and she couldn't allow the girl to fail.

Sliding her hand lower, Ms. Wittmore caught the eye of the gentleman who's glass Cally had just been refilling, she saw the lustful look in his eyes and the way he followed her hand as it moved between Cally's legs. As Cally automatically began to part her legs, a wicked idea came into Ms. Wittmore's mind, suddenly she pushed Cally forwards over the table in front of her, as the four men sat there quickly moved glasses and bottles out of the way.

Once Cally was flat face down Ms. Wittmore lent over her and began to tell the men around her of the story Cally had told her earlier about the man, although she mentioned no names, as she was too clever for that and about how Cally had enjoyed the attention of such men.

The way Ms. Wittmore relayed the story made Cally appear to even more of a slut than was actually true, but she was painting a picture for the men of a very different Cally they had all come to know. She continued to exaggerate Cally's story, confusing both the men around her and Cally herself, but that is exactly what she wanted to do. Keeping people on their toes, not letting them get to comfortable, Ms. Wittmore was beginning to enjoy herself.

She pulled Cally's short skirt up, exposing her bare ass and instructed her to spread her legs wider, which of course Cally did without argument. She looked directly at the man Cally had been serving, she couldn't even remember his name, he was a nobody really, which made this all the more pleasurable for her.

"You see..." She began as she stepped back, "Cally is a very sweet girl, as you all know.." She continued as her fingers spread Cally's ass cheeks.

The man nodded in total agreement, as he adjusted himself in his seat.

"However.. What you don't know is that she is also a total slut!"

Cally gasped in shock and received a sharp slap of Ms. Wittmore's palm in response.

"I see you don't believe me Mr ..."

"Mr Edwards, Jacob Edwards, Ms. Wittmore," the man managed to reply.

"Yes Yes of course.. Jacob! How silly of me to forget, so many guests unfortunately sometimes one becomes muddled with names," she laughed.

"No problem at all Ms. Wittmore and no I can't believe Cally is anything but sweet."

"Oh I assure you she is Jacob... Come see for yourself, all this talk has made her wet I am sure... Feel for yourself."

Jacob looked at Ms. Wittmore in surprise and didn't move.

"Come, come Jacob, I can't believe you are shy or maybe I should offer this opportunity to one of your friends here..."

The other men around the table all looked at Jacob and urged him on with their eyes, even though they themselves would have jumped at the offer.

Slowly Jacob rose from his seat and stood, he ran his hand over Cally's bare ass, feeling her soft, smooth skin. He felt the heat from the area Ms. Wittmore had recently slapped Cally and was tempted to add his own slap but thought better of it. Instead he slid his hand down, pushing his middle finger between Cally's cheeks that were still being held spread by Ms. Wittmore. As soon as his finger reached beyond her ass hole he could feel her wetness and the deeper he went between her legs the wetter she was.

Cally meanwhile was in slight shock, not only from what Ms. Wittmore had be saying about her but that now she was allowing someone other than herself to touch her and worse still her body was reacting to all that was happening. Even before she could stop herself she felt her hips move back against his finger as her needs grew stronger within herself and as he continued to slide up and down her wet slit she couldn't contain the moan that escaped her lips.

"Who else would like to feel?" Asked Ms. Wittmore.

Looking at each man in turn she smiled wickedly and so it began. Each first taking in turn to touch her, feel her wetness and then through Ms. Wittmore's encouragement as a group.

She stood back and gave them more room as they stroked Cally's bare ass and explored between her legs. She moved around the table, dragging a chair with her and sat so she was in front of Cally, directing her to look up at her. Cally did as instructed and Ms. Wittmore saw the confusion on her face and the battle raging within her as her body began to react more and more to the attention.

Ms. Wittmore continued to watch and study Cally's face for a short while longer then standing up she instructed Cally to turn over, which she did. Now lying on her back Ms. Wittmore leaned over her and undid her blouse and yanked the thin lacy bra up over her breasts, then she leaned forward more grabbing Cally's thighs and pulling her legs apart. The men now all gathered in front of Cally had a perfect view of her half naked body and when Ms. Wittmore took hold of Cally's wrists, lifting them about her head and holding them down as she sat back into her chair she simply nodded at the four men.

They didn't need any more encouragement, suddenly there were hands all over Cally. Feebly she tried to struggle free but the weight of their hands and the way Ms. Wittmore had her hands pinned above her head made it impossible to move. She turned her head side to side unsure what she was meant to do, this was not anything she had experienced before, not only that but this was in the middle of the club, something that was totally unheard of before now.

Ms. Wittmore stood once more and leaned over Cally looking directly into her eyes, she saw the fear and uncertainty in her and smiled as sweetly as she could. Leaning closer she kissed Cally, ran the tip of her tongue over her bottom lip, deepening the kiss she felt Cally relax more and begin to kiss her back. As there kiss became more passionate Ms. Wittmore felt Cally's body respond more and more to the attention from the men, she began to moan lightly into their kiss.

"See what a true slut you are my dear," she whispered to Cally.

In response Cally just stared at Ms. Wittmore and felt her cheeks flush, which just made Ms. Wittmore laugh.

"Should I let them have their way fully with you my dear? I bet they are hard as rock and I know you do like to feel a hard cock buried in your slutty cunt!"

Before Cally could protest Ms. Wittmore silenced her with another passionate kiss.

Ms. Wittmore looked up and watched as these four men fondled and molested her Cally, she watched as they became braver and urged each other on. Jacob was now knelt between Cally's legs licking her, while another younger looking man stood behind him holding her legs up bending them at the knees and spreading her open for his friend. Meanwhile a third one was busy sucking and nibbling on her now rock hard nipples, moving happily between each breast, leaving tiny marks across her soft skin. The fourth was leaning over her from the other side, touching any part of her body he could get his hands, then suddenly they would swap positions, each getting to taste and enjoy Cally.

Ms. Wittmore knew Cally couldn't last much longer, this kind of onslaught would be too much for her to be able to contain those ever building needs. She judged each man for his performance and skills, silently placing a bet on which would finally tip Cally over the edge and bring her to orgasm. She could be mean and stop this now or she could be meaner and let them continue, she has already fed the idea of letting them fuck Cally to the girl herself and she knew although she wouldn't believe Ms. Wittmore would allow that she would be doubting herself as well.

Cally was fighting with all her might to try and block out what was happening to her, she could feel their hands, their fingers, lips and tongues all over her body and in turn her body felt like it was on fire. Each nibble or bite sent a million shocks through her, each lick on her swollen needy clit made her body want more and more. Her mind was in turmoil, she was feeling used and as if she was being abused yet her body loved it, reacted to it. Sweat ran down her back, over her torso, she bit her lips to try and smoother the moans that escaped them. She shut her eyes tightly as her hips began to thrust out of her control, she knew Ms. Wittmore was watching her, she couldn't look back at her, she felt betrayed yet excited at what was happening.

What surprised Ms. Wittmore wasn't so much how Cally still managed to fight off her approaching orgasm or orgasms but that when she looked around the other guests and staff were continuing with their evenings as if nothing was happening out of the ordinary on this table, she almost had to laugh to herself, could these people not be shocked by anything these days.

Her attention was fast bought back to Cally as she felt her body begin to buck as a first orgasm ripped through her body. It was quickly followed by another and another, each she knew stronger and wilder, the men didn't let up, now encouraged that they were making her orgasm over and over. When Cally finally squirted her juices over the young unsuspecting one of the group's face causing him to fall backwards in surprise the action came to a sudden halt, as if they couldn't quite believe what they just saw.

Ms. Wittmore laughed out loud and finally released Cally's wrists but the girl didn't move, she just lay on the table breathless and spent.

"Now I think you believe me," Ms. Wittmore simple said as she gently helped a very confused Cally up from the table.

The four men could only nod at Ms. Wittmore and as she took Cally in her arms and hugged her tight. She looked over Cally's shoulder and gestured for Louis to come from behind the bar, he approached carrying a small blanket that he gently wrapped around Cally, leading her away.

Meanwhile Ms. Wittmore spoke quietly to the four men and then summoned over one of the waitresses to serve the gentlemen with whatever they required for the rest of the evening free of charge.

Louis guided Cally back towards Ms. Wittmore's private quarters, once in her private room he carefully helped her lay down on the couch, giving her a slight kiss on the forehead and without saying a word left. At the door he was met by Ms. Wittmore, he gave her a disapproving look and walk back towards the bar. Ms. Wittmore smiled to herself, she knew Louis had a soft spot for Cally and now he too had seen just how much control she had over her. She wasn't normally into such games but there was high stakes and she needed everyone to be reminded who they were dealing with. She was even tempted to have Seb fire Louis later but then again she needed good staff around her at the moment and she knew no matter what he might think, Louis was loyal.

Ms. Wittmore approached the couch and gently sat down next to Cally, whom then crawled into her arms. She lightly kissed her girl on the head and let her bury her head into her shoulder.

"Why?" Cally simply asked.

"Because I could my dear... And because I need you ready."

"Ready for what?"

"All in good time my dear, but know this evening you have made me very proud of you."

Cally closed her eyes and Ms. Wittmore pulled her closer, breathing in deeply. Cally smelt strongly of sex from her orgasms and even though it wasn't through her fucking it was still alluring to Ms. Wittmore and she realised almost addictive.

She decided to let the girl rest a while here then she planned to do the one thing she had never done, she was going to take Cally to her home and let her spend the night with her in her bed. She felt a sudden need to keep her close, especially when she thought of what was coming, it would be Cally's biggest test, but also probably also her own.