Ms. Wittmore Pt. 04: Challenges

Placing the phone receiver down Ms. Wittmore sits back in her office chair and smiles to herself. She hadn't thought much about Councillor Davis since his last visit to the club but now that the new Mayor was starting to make noises regarding new licencing laws, he was very much on her mind. Well more how useful he and a few more of his fellow councillors could be to her.

Turning her attention away from business matters for a moment, she lets her mind wander to Cally and she can't help but smile once again, but this time her smile is soft and true. Flicking her computer screen to look at the live feed from the surveillance cameras she secretly had installed at Cally's apartment, she quickly scans each room. Finally clicking to enlarge the picture of the camera covering Cally's bedroom, where the she is still sleeping, completely unaware of their existence and the fact she is being watched.

Settling back in her office chair, sipping her coffee she slowly zooms in on Cally's face, she looks so peaceful and content sleeping softly, Ms. Wittmore can't help but adore and admire her. Every test and every challenge she put before her, she more than meets and exceeds all her expectations. Lightly she runs her finger tip over the screen as if tracing Cally's face and gradually zooms out to watch as her Cally begins to stir from her deep sleep.

Cally slowly wakes up, stretching her long legs out, feeling the tightness in them. Then continuing to stretch her tired aching body out she finally opens her eyes trying to focus on the bedside clock. Its almost midday, but seeing as she didn't get to bed before 5am that's not surprising. Grabbing the pillow next to her, she pulls it over her head and groans deeply, not wanting to get up but knowing she will need to be at the club soon.

Ms. Wittmore smiles as she watches the way Cally covers her eyes with the pillow so tightly, its sweet and endearing to see. Its such an innocent act, almost normal, but she knows behind it Cally's mind will be racing, retracing the events of the evening before. She had come to know Cally so well, seeing daily the battle in the woman, the way she wanted to fight what was happening to her, yet the way in the end she just simply caved and submitted fully.

Dragging herself out of bed Cally heads to the shower, spending longer than required but taking advantage of being able to do so and enjoying the feel of the hot water flowing over her. Carefully she checks over her body, looking for new marks or bruises and smiles to herself and blushing a little at the memory of each tiny one. Continuing to check her body over, her fingers run over her legs, sliding all the way up to her mound and on feeling the start of regrowth, she reaches for her razor, the last thing she would want to do is fall foul of one of Ms. Wittmore's easier rules.

All the time Ms. Wittmore watches Cally's morning routine, moving from one camera to the next as she moves around house. She knows her movements inside out, but then as she watches her every morning and Cally is a creature of habit that isn't surprising.

She continues to watch as Cally re-enters the bedroom, letting her silk robe fall to the ground. Ms. Wittmore can't help but admire the way Cally's body is toning up, the extra sessions with Ms. Wittmore, along the dancing at the club are really beginning to show. Watching as she walks over to the chair in the corner of the room, sorting through the clothing thrown over the arm, letting most fall to the ground, she tuts to herself at the her untidiness and makes a mental note to make a surprise visit to her apartment soon and correct this lazy behaviour.

As Cally begins to dress, Ms. Wittmore's attention is finally averted as Seb enters her office. Closing the screen down she turns her attention to the man now stood in front of her with an arm full of files.

"Good morning Ms. Wittmore."

"Well officially it's afternoon now Seb."

"True, very true, where would you like these?"

Clearing a space on her desk she points for him to place the files down, lifting the first off the pile.

"Is this everything we have Seb?"

"Yes Ms. Wittmore, every record of every member of the City Council that has and does use our clubs and services."

"Good, good... And have we managed to fine anything of interest about the Mayor himself?"

"I have a couple of very good people working on that as we speak, they assure me they will find anything that is there to find."

"Very good... Thank you Seb."

"You are welcome Ms. Wittmore," replied Seb as he turned and left the office, making sure to leave the door ajar as Ms. Wittmore liked it.

Opening one of the files in front of her Ms. Wittmore begins to leaf through the pages, all the information she needs to aid her in getting councillor Davis on side, even he if is reluctant at first is sitting in front of her. A man like Davis relies on his reputation, a wealthy business man with his fingers in many pies, so to speak, will do what is required to avoid a scandal. Plus a young family and wife who has expensive tastes, all this Ms. Wittmore knew exactly how to use for her own gain. His uses were limited but if it came down to a vote in council chambers, she would see that she secured his.

Opening the next file underneath, she couldn't help but smile wider, Councillor Raymond, unlike Councillor Davis was most definitely going to be more use. His position within the Council put him in direct contact with the Mayor daily and would be very useful indeed. There was plenty to use on Raymond to get him on side, one way or another. Councillor Raymond was well known in her clubs for his tastes and was known to mishandle the girls at times. Turning the page Ms. Wittmore was faced with one such incident, where Raymond had got heavy handed, the photograph of Lilly's black eye and cut lip could be very useful indeed.

A while later, as she opened the final file and began to take a few notes she heard approaching foot steps, a light tap on the door and automatically she knew it would be Cally, just arrived.

"Enter!" She called out and sure enough Cally walked confidently through the door.

"Close the door, my dear," she instructed and with a nod of her head Cally complied.

It was rare that Ms, Wittmore ever closed her office door fully, it was a sure sign to anyone approaching not to disturb and in Cally's presence it normally meant under no circumstances disturb.

Cally closed the door and walked forwards, greeting Ms. Wittmore as she approaches the desk. Ms. Wittmore in turn stands up and moves around the desk, holding her arms out for Cally to walk into. Wrapping her arms tightly around Cally's waist and pulling her into a passionate kiss.

"Now my day is complete." Ms. Wittmore declared as finally she broke their kiss.

Moving back behind the desk, she tapped the top instructing for Cally to sit next to her as she sat back down in her chair, closing the file open in front of her and moving them all to make a space for her to sit down.

"How did you sleep Cally?"

"Hmm soundly, thank you Ms. Wittmore."

"Of that I am sure my dear!"

Cally blushed deeply, which made Ms. Wittmore smile even more. Her innocence still was her biggest appeal, yet she still submitted in every way and this alone made her prefect for Ms. Wittmore.

Attempting to change the subject and avoid having to discuss the previous nights details, Cally ran her finger over the files in front of Ms. Wittmore, looking intently at the photograph that somehow was now sat on top and fully on show, she slowly turned it towards her.

"Someone you know my dear?" Ms. Wittmore asked.

"I think so, who is it?"

"His name is Leonard Rawles."

"Leo, yes I remember him," Cally replied.

"Oh? From where do you remember him?"

"A while ago now, but he used to come into Gus' bar a lot."

"Really! Now you have my interest, tell me more."

Cally looked up and saw a strange glint in Ms. Wittmore's eyes. She thought back to those early days working at Gus' bar and small smile crossed her face when she remembered how shy Leo seemed to be when she first met him.

"What exactly do you want to know?"

Sliding her hand up Cally's thigh, pushing her short skirt upwards as she did, Ms. Wittmore stood up and moving so she now stood directly in front of her, forcing Cally's legs apart, she leaned in towards her. Teasingly kissing her way up her neck as her hand moved higher and higher she whispered softly, yet firmly into the girls ear.

"Tell me everything and if I like what I hear you will receive a sweet orgasm my dear."

"And if you don't like what you hear?"

"Hhmmm if I don't like it, you'll receive such a spanking you will struggle to sit down for the rest of the day."

Ms. Wittmore smiled as Cally let out a moan, as much as she tried to not show it, Ms. Wittmore knew Cally got turned on when she was talked to in this way and to emphasize her words she let her finger nails dig into her thigh and was rewarded with a deeper moan. She stepped in closer and let her fingers drag over Cally's bare, soft, smooth mound.

"Such a slut, look at the way you spread your legs and you think I don't feel you pushing your hips forwards. Always so greedy to be touched, to be used. But these things have to be earned as you know, so tell me how you know Leonard Rawles and I'll decide which reward you receive."

Cally moaned again, she could feel her pussy becoming wet and she was trying to discreetly push herself closer to Ms. Wittmore's fingers, to feel her touch. She cursed herself for being so predictable and her body yet again giving into its needs.

Taking a deep breath as Ms. Wittmore's fingers continued to tease her inner thighs and over her mound, she slowly started to tell Ms. Wittmore about the Leo she knew. Starting from the first time she remembered noticing him at the bar, always sat alone, at the far end, nursing a glass of whiskey. He never interacted with the dancers, seemed hardly to even notice them really, which made him more interesting to Cally. She attempted on a number of occasions to draw him into a conversation but only ever got short abrupt replies, so in the end just gave up and left him to his drink and to sit and look on from a distance at the girls dancing.

Ms. Wittmore in turn listened intently to all Cally told her and as her story continued she became more and more interested, pressing for more details and rewarding Cally by slipping a single finger down between her now wet folds but careful not to make contact with her ever needy clit. She was already beginning to draw a picture of Mayor Leonard Rawles in her mind and a twisted plan was beginning to form.

Cally moaned more with frustration than anything else as she felt Ms. Wittmore's finger and continued on with her story. Remembering the first night he moved to one of the front tables, still with the whiskey in hand and still not really taking any notice or interacting with the girls on stage.

That was until she took to the stage, suddenly he was sat bolt right up and his eyes never left her, following as she moved around the stage. When she had approached he had held his hand up to stop her when she was just out of hands reach to him. She had stayed at that point and finished her routine, making it almost a private dance for him and as the lights went down and the music faded at the end of her set, he simply got up and walked out.

Later that night when Cally was leaving the bar, Gus had approached her and handed her an envelope, telling her she had a new fan in his normal smirking way, even though he knew unlike others she didn't really do as they put it extras, or up till then hadn't.

Ms. Wittmore pressed for more details, asking what was in the envelope and when Cally replied a hundred dollar bill and a simple note that said "you are too good for this place," she couldn't help but laugh out loud.

"Seems Mayor Rawles knows talent when he sees it Cally," she scoffed.

"Mayor?"

"Oh yes my dear sweet Cally, Leonard Rawles is no other than the Cities very own new Mayor and you my dear could be the answer to all my worries."

Cally moaned deeply as Ms. Wittmore's finger finally pressed against her clit in reward and automatically she spread her legs wider, causing Ms. Wittmore to laugh out loud once more.

"All in good time my little slut... Continue, tell the rest and we'll see which reward you are due."

As Ms. Wittmore's finger started to circle just above her now hardening clit Cally continued on, telling her how from that night he would appear almost nightly, sat at the bar until Cally came on stage, when he would move to the same table at the front and she in turn would dance almost just for him. Then at the end of the night she would be handed an envelope by Gus who would smile sweetly and hold his hand out, expecting her to give him half of whatever Leo had left for her.

After a few weeks, Gus, never wanting to miss out on a good thing then suggested that Cally should dance twice a night, other customers were noticing this special attention from Cally and were starting to grumble.

So Cally would dance twice, first early in the evening when the bar was quieter and again as normal when the bar was full and busy. Basically as soon as Leo would appear, she would simply dance solely in front of him for him and she explained how she watched him get braver and braver at these quieter times, until the night he stood in front of her and ran his hand up her leg.

Ms. Wittmore suddenly stood back, almost in shock and not believing what she was hearing, could it really be this simple.

"You allowed him to touch you?" She demanded.

Cally could feel the blood rush to her face as she blushed, this wasn't something she was proud of and it had been the first time she had let herself to be touched on stage and Leo was the only one to do so. Well until she met Ms. Wittmore that was of course.

Ms. Wittmore on the other hand was now excited and sensing Cally's embarrassment, she moved in close again and decided to take control of the situation in order to get the rest of the story before Cally clammed up on her entirely, which she knew was very likely to happen when the girl became embarrassed.

Grabbing Cally by the waist she pulled her off the desk, spinning her around, slamming her palm in the middle of her back and pushing her roughly back down onto the desk. Grabbing her arms, forcing them behind her back, holding her wrists with one hand nice and tightly, she yanked her skirt up over her hips, kicking her legs apart and pressed her own body down on top of her.

She Dragged her finger nails up her inner thigh, making them dig into her flesh, hard enough to leave a mark but not actually breaking the skin. She smiled as Cally moaned out once more and that smile broadened when she gave out a loud scream as the first of Ms. Wittmore's stinging slaps landed on her bare ass.

"Tell me the truth slut, you enjoyed him touching you?"

Shocked by the sudden change in the situation, as well as both the smacks raining down on her ass and the tone in Ms. Wittmore's voice Cally stumbled to reply.

"Noooo of course I didn't," she cried out.

"Liar, you let him touch you, you enjoyed it like the dirty slut you are," continued Ms. Wittmore.

"Gus!..." she managed to get out before the next combinations of perfectly timed and aimed smacks landed on her now burning cheeks.

"Gus?" Spat Ms. Wittmore.

Through building tears of pain and confusion Cally explained than when she had looked across the bar at its owner and her boss, Gus, he was flapping his arms in a way to encourage her, no demand her to let Leo touch her and back than she was more than a little afraid of Gus so she had complied.

Ms. Wittmore gently slid her hand over Cally's red hot cheeks, pulling back and beginning to softly kiss each in turn. As she slid her hand between Cally's legs she wasn't at all surprised to feel her girl was soaking wet, almost dripping. Gently she stroked her from behind, parting her folds and letting her index and middle finger slide up and down her slick slit.

"Hmm good girl, my sweet Cally, my slut," she whispered as she continued to slide her fingers. "How did he touch you Cally? She asked.

"I don't remember Ms. Wittmore," Cally replied.

"Now now Cally, we both know you do.. Was it like this?" She asked as she pushed her fingers up over her hard clit.

"No," Panted Cally, as she felt Ms. Wittmore's touch and her body instantly reacted.

"Oh well, did he just go for the home run then?" She asked as she slid her two fingers deep inside of Cally.

Cally let out a deep satisfactory moan and automatically pushed back against Ms. Wittmore's fingers.

"Did you let him finger your tight cunt Cally, as I am now?" Asked Ms. Wittmore.

"No..."

"No? So what did you let him do slut?"

"Please, Ms. Wittmore."

Thrusting her fingers deeper, beginning to twist and turn Ms. Wittmore laughed, giving Cally a warning of withdrawing them before she could enjoy them fully.

"No.. Please Ms. Wittmore, please don't stop!"

"Then tell me Cally, what did you let him do to you?"

Cally bit her bottom lip, in a way she had always thought herself better than the other girls that did tricks on the side but really she wasn't. When it push came to shove, as soon as she found herself in that position she hadn't done anything to stop Leo and in fact under Gus' watchful eye she had encourage him.

That first time she had simply placed her hands on his shoulders, lent in and whisper in his ear telling him how much she wanted him to touch her. Through teary eyes she told Ms. Wittmore all this and how he had fumbled and seemed so inexperienced, almost afraid to actually touch her. In the end she had, had to grab his hand and press it against her, while she ground down on his fingers and finally instruct him to push his fingers inside her.

At this comment Ms. Wittmore scoffed "To think I thought I was the only one to bring the true slut out in you Cally!" and thrust her fingers deeper.

Cally moaned out and tried to explain the difference but Ms. Wittmore just laughed and began to finger fuck her even more roughly.

"I'm not disappointed Cally, far from it, you delight me more than you will ever know with this information."

All the time Ms. Wittmore continued to finger fuck Cally from behind, as if to encourage her to talk. If nothing else Cally was a proud girl and far from a common slut, so to be admitting she had let a man use her in the days before Ms. Wittmore was a big thing and a huge eye opener for Ms. Wittmore. She began to wonder what else there was to the sweet Cally she didn't yet know.

She thrust her fingers in and out, twisting and turning as Cally told her story in between pleasurable moans as her orgasm built within her. She hadn't planned on letting Cally cum just yet but she felt compelled to give her the one pleasure she normally had to work so hard for. After all unbeknown to Cally she was now Ms. Wittmore's secret weapon and boy was she going to use it to her advantage.

As her orgasm hit, Cally thrust back and bucked her hips wildly, from her view behind Ms. Wittmore got to enjoy watching her and to feel her juices squirt over her fingers. She felt her inner muscles clamp down tight on her fingers and suck wildly at them, which once more made her feel the pangs of jealously for any man that had experienced her orgasming on his cock.

She gently stroked Cally's back as she recovered, telling how wonderful she was and how proud she was of her, giving her all the reassurance she both craved and needed, until her breathing finally returned to normal.

Finally Ms. Wittmore withdrew her fingers, normally she would present them to Cally to lick clean for her but today she wiped them clean by sliding them between her ass cheeks, pressing her finger tips against Cally's tight ass hole as she did and delighting as Cally automatically pushed back against them.