Chapter 11

“Well, Jen, what do you have in mind for this week’s rent?” On her knees in her relaxed position, knees spread to elbow width, her pussy lips open in front of him, she glanced behind her where the gift boxes were usually on display but saw nothing. As her eyes returned to his, he could clearly see the question in them before she answered with, “I don’t know, Sir. I thought you probably had some new challenge for me this week.”

“Are you seeking another contract from me, Little One?” Black asked with a hint of a smile on his lips.

“Yes, Sir.”

“Ok then, we have enjoyed a month of fun together thus far. You have shared openly and honestly with me and have met all challenges with courage and commitment. You have brought daily smiles to our little family and I have truly appreciated observing your achievements.

“Do you want to continue these weekly contracts or would you like something more long-term?” Black watched her closely, seeking to follow her thinking process.

However, she only took seconds to reply, “What would long-term look like?” she sweetly asked.

He had expected more tentativeness but he saw none. “I am thinking about a one-month contract for now,” he continied, “we would set the parameters of that contract in advance. You would commit to complete compliance and we will have some more fun.”

‘Fun suggests only one thing now and that is something involving me and a sexual act’, she was thinking, ‘it hasn’t been all that hard so far’, her slightest smile emerging. ‘But what does he want for a month’?

“Still, Sir, I can’t commit until I know what you ask of me.”

“It’s quite simple, really. You agree to do everything I ask of you without complaint and continue to show me the high-quality effort and achievement you have shown thus far.”

She knew she wasn’t going to get any further details but she wanted to stay where they were. Brian was safe here and she didn’t mind the games they had played so far. He hadn’t touched her or hurt her, or Brian, in any way. She had no choice as she thought it through, “Ok, I accept the terms of the contract.”

“Very good,” stated Black clapping his hands together, once. She saw the little boy in him at the moment and her motherhood instincts wanted to cuddle him to her bosom.

He reached into the side pocket of the Parker and drew a mauve-colored envelope and proceeded to hand it across. She accepted it as he motioned for her to rise as he did so himself.

On the way to the door, “As always, do not open the envelope until you get into bed. Sleep well, Little One, sleep well.”

Once Brian was settled down for the night she flew through her wash and brush. Jen couldn’t wait to jump into bed and read his letter. For some reason she didn’t want to think through as she was now looking forward to a new challenge. She was having fun.

She could hear his voice on reading that word. Her bum muscles tensed. She understood.

For tomorrow’s attire, please wear your red strap dress, no bra and bring along Bob to lunch.

Sleep well.

“Rough job, but hey, somebodies got to do it,” ran threw her mind as her hand entered her panty to begin her twenty minutes of edging. With a smile on her face, “This should be easy,” were the last words spoken for the night.

Sunday, report time.

As he opened his door and was saying good evening, she scurried past him with her head down and going straight to the living room. He followed and took his seat.

She assumed her presenting position, chin up, eyes on his, hands on each thigh, knees just over elbow width apart, her cunt agape, soaking wet, her labia lips engorged, almost purple, pulsing in front of him. ‘Probably due to the change in air temperature’, was his smiling thought. Finally, below her pussy he could just see the hint of the new jewel that adorned the top of the anal plug she held in her ass. ‘Gorgeous, simply gorgeous,” was his thinking.

After his slower-than-usual visual inspection he looked into her face, her eyes. Her make-up was perfect but nothing gaudy. She used highlights only as her mascara was thin, black and captivating. Her lips were full, plump and soft red, perfect.

But her eyes. Not her eye makeup, her eyes, the windows to her mind, were craving, wanting. She needed something with that desperation only a few are ever in a position to attain. She was an animal right then. Every fiber of her being was ready to pounce, to act.

He could smell her need. He smiled, “Well, Little One, here it is, another Sunday and time for your report. I must say you look ravishing this evening. Beautiful just isn’t strong enough, thank you.”

She didn’t nod or respond in any way. She just stared into his eyes. Waiting. Craving. He moved his hand indicating she could begin, supporting the movement verbally as well, “Please begin.”

It took her several seconds to start, “Please, Mas...” his hand had immediately risen to a halting command. She stopped mid-word and then lost control and burst out with, “Sir! Please let me cum, please, I can’t think straight enough to provide any kind of report,” she rapidly whined.

Starting to fall into herself he flicked his finger which she knew meant to get back into position and she did. “Please...” tears ready to burst forth.

He extended his shoed foot to her. He had been in town all day at business meetings having to rush home to be there on time to open his door. He was wearing a well-polished, rounded-toe, black businessman’s shoe. She saw him move his foot into position, directly in front of her, toe up, heel resting on the floor.

“I believe you could provide me with a detailed report right now if you choose to. I do. However, if you think you can’t then you may bend over and slather the toe of my shoe with your saliva and, once well covered, you may squat and fuck my shoe. Your choice, report or get your tongue to work.”

He wasn’t commanding her as his voice had remained conversational in tone. He waited sitting back in his chair with his shoe toe in the air. It would have to be her choice since he only provided the options.

She was horrified as she looked at his shoe. She didn’t want to do this. She couldn’t do this. This was just too much. She looked up expressing her horror. Black saw this so suggested, as he settled back, “Please commence your report. Always remember, Jen, it is always going to be your choice. I will never force you to do anything. How about you start with your reading of Sunday’s missive.”

He wasn’t letting her wrap herself in any single emotion. He was keeping her moving and her mind was having to move from one set of thoughts to the next before her emotions could fully catch up. Report.

She enhanced her present position then took a deep breath as she fought to focus, “When I got home Sunday evening, I was quite excited to get Brian asleep and read your letter.” Truth was her only option. It was thoroughly ingrained in her now.

“On first reading I thought this was going to be an easy week. Twenty minutes was nothing. I could easily forestall an orgasm. And it was, and I did. Well, it was a bit of a challenge winding down and falling asleep Sunday night, but..., I rolled through Monday with relative ease.”

He nodded his head in support then looked up and stated, “Details,” said as a soft reminder. She understood.

“Monday morning, I woke up to a very vocal Brian because his mother had not pulled his window blind tight the night before.” Black expressed a tisk-tisk sound through his teeth.

She continued, “I jumped out of bed to calm him and I had to feed him. Basically, it took about two hours before I completed my toiletries, settled on the couch, and then began fingering myself. I wasn’t in the mood but worked my kitten over for maybe even twenty-five minutes or so but couldn’t generate any real arousal.”

“I had to start over again about a half hour later to make lunch on schedule.” She was keeping her eyes on his trying to get a read. Did he believe she was being honest? What is he thinking?

“Since I wasn’t getting much from my fingers earlier, I thought I would climb into bed and use my vibrator. This worked better and I was able to edge twice.” The memory brought a small smile to her eyes.

Black asked, “What is edging?” her smile evaporated as she dropped her eyes to think. He flicked his fingers and she knew she was to lift her head.

She did and as she opened her mouth to speak, he spoke first, “Actually, instead of explaining how to edge, how about a proper presentation, Jen? Yes, let’s walk me through one full cycle of edging. You may relax your arms and use your hands.”

He was kind of smirking seeing that maybe she wasn’t sure. Then he leaned forward adding some intensity, “Without cumming.” He saw she was going to say something by the look on her face, maybe argue? He didn’t need it.

His look was enough for her to understand that he meant what he was saying. She had no choice so slowly her hands dropped into her lap. He nodded his head in encouragement.

Her right hand, fingers, started to pet her pussy as her eyes closed. Her left hand rose to her breast to fondle her nipple. The speed of her hand movements began to accelerate. Within a minute sweat began to appear on her brow and her skin began to redden.

Her fingers entered her now sloppy cunt. You could hear the squishing sounds as her fingers stroked in and out. Her face flushed and her breathing had picked up. The tip of her tongue protruded from her lips as she started to shudder. She was close.

Black quietly stated, “No.” Even in her above-normal sexual need she heard his, ‘No’. Three seconds later she stopped her manipulations and she was panting now.

“Look at me,” Black encouraged. She opened her now dazed, unfocused eyes. Slowly they found his face, his eyes as her eyes begged for release.

He looked at his toe and she did too. He added, “The reason you want to slather the toe with your spit is to ensure the toe is clean. That way you won’t get any unlucky infection or something.”

He waited and then wiggled his toe. She looked once again into his eyes with tears forming in hers and then leant forward. Taking his shoe into her hands she lowered her head to his toe. As she bent forward, the last thing he noticed was her cute little pick tongue peeking through her lips and his next feeling was the light pressure she applied to his shoe. She was licking it.

He gave her thirty-forty seconds before he encouraged, “Make sure you get the toe really wet. Slather it well.” Her speed was picking up as he added, “Finger yourself as you lick,” which she did. Another half minute and she lifted off the shoe so he glanced down.

The top of the shoe was dripping saliva and her right hand was pumping in and out of her very sloppy, needy cunt. Her begging eyes sought approval of the prep work.

He nodded and she moved forward to position herself over his shoe. She tried squatting over the big, wet, black shoe toe. She couldn’t really get any good pressure on her cunt so she came further forward by placing her hands on his knees and lowering her hips over his toe. She positioned her cunt lips on the toe and began experimenting with pussy to shoe placement and various speeds.

With her head between his knees and her hands gripped his knees as she rolled her hips back and forth driving her pussy across the shoe leather.

“Eyes.”

She opened hers and sought out his. The lust in her eyes was so evident his balls tightened up into their own cum producing moment in support of the most rigid hard-on he could ever remember experiencing. She fucking amazed him.

Observing her features he could see her orgasm was close. “Ok, my Little One, on the count of five I want you to come for me.”

Looking into his eyes she just nodded her head while pushing down even harder onto his shoe toe. “One, my horny, Little Slut.” Her right hand left a knee and started rubbing her clit while she worked her cunt over the shoe.

“Two, a good slut gets rewards.” She slammed her hips forward.

“Three, bad sluts get spankings.” She groaned out loud now as every hip swing drove the shoe deeper into her cunt and her fingers were a blur over her clit.

“Four, are you my little slut, Jen?” She nodded letting out a hissed, “Yes.”

“Five, cum for me, my Little Slut, cum!”

She exploded. Her eyes rolled into the back of her head as she screamed out her pleasure. Her orgasmic juices splashed onto his shoe and down to the floor. It was a flood as her fingers continued to flick across her clit. For two minutes her whole body shuddered in spurts and spasms.