Executive Decisions: Working Dinner

The message popped up on the computer screen and filtered out of her speakers. “You have one new message.” Startling Madie out of her most recent fantasy.

The computer beeped again. “You have two new messages.”

Clicking open her email program, Madie looked at the inbox. Her heart raced as she saw the messages were from Grayson. The header to the first one read “A working dinner” and the second one said in the subject line “Stop fantasizing and read my message.” Quickly, she opened the first message. “Good afternoon, Madie. Tonight, we will be having a working dinner. Bring your notes on the proposal for the northeast division and do the following exactly as I have written out. Behind the door to your office you will find an outfit hanging on the hook. Put it on before you leave. Don’t worry it will fit. I’ve had my hands on you. I know your exact measurements…”

Madie jumped up to look at the outfit before finishing the message. Thoughts of his hands on her body had her pulse racing and skin tingling. She closed the door and found a blouse and skirt similar to what she normally wore. She removed the blouse and found it to be made of the sheerest most delicate material she’d ever known. She put it to her lips caressing the silky softness. She inhaled. He’d sprayed his cologne on it. Her pussy clenched at his musky scent. She could feel the moisture building along with the excitement.

The skirt made from the same sheer silk ended just above her thighs, any shorter and there’d be a clear shot to her crotch. In fact when she sat down she knew her pussy would be completely visible. When this thought came to mind she moved back over to her computer screen to read the rest of the message.

“…How do you like the outfit? I’m sure you couldn’t wait. I know you, my love. Are you wet right now? Touch yourself. Good. The shoes I want you to wear are under your desk. We saw them the other day, the black fuck-me-pumps as you called them. I loved the way your ass curved above your long luscious legs in them. No bra. No panties. Remove your jewelry. There is a velvet choker in your top drawer. The nipple chain you asked about is next to it. Put both on. Button the bottom two buttons of the blouse and no more. Make sure everything I have noted has been done. You will go to Legend’s and sit at the table I have reserved. Be there at 7 no later, no earlier. Wait for me.”

Fired-up beyond imagination, Madie wished the day away. She replied to her work emails and returned a few phone calls. Renate came in just before six and asked Madie if she wanted to join her and Griffin for a drink after work. Madie smiled, “Maybe some other time Renate. I have plans this evening.”

“By that wicked grin on your face I’m sure those are some pretty exciting plans, Madie. I can’t wait until the next poker game. I could stand taking more of your money. You have the worst poker face I’ve ever seen. One of these days you will have to tell me who this mystery man is.”

“One of these days Renate. I promise. Right now I’m just enjoying him as much as I can. I can’t help it. I want him all to myself.”

“If that is the outfit you are wearing tonight, I’d say he’ll be enjoying YOU!” Renate laughed as she walked toward Madison’s door with the clothes hanging on it. “Have fun sweets. I’ll hold you to that promise. I have a feeling this story will be quite interesting.”

Tossing her head back, Madie laughed out loud at Renate. A group of them got together once a month for a poker game. Madie won more from luck than anything else at times. If she had to rely on her poker face as Renate alluded to, she would have lost her shirt. A wicked thought came to mind maybe she should suggest a game to Grayson. “Thanks Renate, you have a good night too. I will talk more with you tomorrow, we’re doing lunch right?”

“You betcha!” Renate smiled and left Madie to close up her office for the night. Madie shut the door behind Renate. She was so excited she forgot to lock her door. She remembered the lock only after she’d removed all her clothes. The thrill of someone walking in on her made her enthusiasm increase.

She slowly stepped into the silk skirt and slid it up her thighs over her hips, zipping it in the back. It ended exactly where she thought it would, just below her curvaceous ass. Her hands caressed the soft material barely covering her backside. After putting on the nipple chain, her fingers circled her areolas. Rivulets of breast milk leaked from her nipples. Watching her nipples pucker further still had her breathing heavier knowing Grayson would notice her breasts immediately. Madison tugged gently on the chain moaning at this action. Grayson would not be so gentle.

Smiling, she eased into her top, the creamy color accentuating her tan. Buttoning up the blouse she left the top three undone exposing her slender neck with a hint at the nipple chain as she had been directed. She clasped the choker smiling as the Celtic cross dangled in the hollow of her throat.

Her hands traveled to the warm spot between her thighs. She dipped a finger into her moist heat. Wow. Wet. So very very wet. It always amazed her that she could get so aroused, so soaked just at the thought of him. The tip of her index finger tickled her clit and caressed her outer lips. Madison shivered knowing this would be an amazing night.

The clock in her office chimed the half hour mark. Madie shook off her state of arousal and looked at the time. “Oh my gawd. If I don’t get out of here now I will be late. He said to be there exactly at 7. Well, if I’m a minute or two late it won’t be so bad.”

She grabbed her pocket book and maneuvered her feet into her high, high-heeled shoes. She walked around her office a couple of times to get adjusted them. As soon as she was accustomed to the new height, she set off for the restaurant.

“Damn, I am two minutes late. I hope he isn’t here yet.” Madie walked up to the hostess. “Table for two under the name Grayson Brooks, please.”

“Right this way, ma’am.” The petite hostess looked up at Madie and led her to a U shaped booth facing the entire dining room and the window out front. Madie had to sit on the edge of the seat and swing her long legs together into the booth to keep her skirt from riding up any further. Even with this effort her skirt hiked up showing a bit of crotch to anyone who looked in her direction. The other tables were lower than the booths along the outer edge of the room.

A note taped to a bottle of wine read “Knees shoulder width apart. Have a glass of wine.” An arrow directed her to turn the paper over. “You are late.”

Madison shivered at the last line as she moved her knees to follow his directions. What did that mean? Will he not show up? Is he angry with her? She was only two minutes late. It wasn’t even her fault. Damn traffic. She searched the room for Grayson, sadness reaching her eyes when she could not locate him.

The waiter brought her a menu. He stared at her nipples clearly visible, and aroused, through the thin, light colored shirt. She looked at his crotch noticing his erection. She brought her glass of wine to her lips to occupy her hands. Her pussy twitched in anticipation of Grayson’s arrival. “Thank you” she managed to mumble forcing her attention to the list of appetizers. Should I order? Or should I wait for Grayson?

She continued to look over the dinner specials when she noticed a shadow move over the table. Thinking the waiter had returned, Madie prepared to tell him she would wait for her companion to arrive before ordering. Her mouth opened and no sound came out as she looked up into steel blue eyes staring back at her. She beamed her pleasure at his appearance. He continued to stand quietly before her. Hand reaching out, Grayson knocked a fork onto the floor. Bending to retrieve it, he took his time rising making it obvious what he was looking at.

Madison shifted slightly in her seat. She ached for his touch. She felt a trickle of her juices slide down to her ass. He lifted his head and continued to stare at her as he rose to full height. His eyes came to rest at her breasts. A smile crossed his face. “I’m glad to see you followed my other details.”

He sat down next to her taking her hand in his. The waiter returned to the table and Grayson placed their order, not asking or waiting for her to make a choice. She nodded, barely noticeable was her agreement to his selection for their meal. He leaned into her pulling her body against his chest, wrapping his arm around her. Sliding his hand down her shoulder to her hip he let his thumb trace her leg inching up her skirt. When the skirt reached the desired location his fingers dipped down between her thighs spread apart as he’d asked her to do. “Now for the appetizer. I don’t want you to cum until I say you can. Then you will do as I request.”

His fingers slid over her smooth shaven lips into the folds and curled deep inside her. In and out twisting like he so expertly does. “Mmmm…you are so warm here baby.” Grayson’s fingers tapped on her mound and lower. Then he smacked her bare wet lips startling her. “What have you been doing? You are so wet for me.”

Before she could speak he dipped his head to claim her mouth. Her fears of being watched and everyone knowing what they were about melted quickly, along with her body into him. She gave in and over to him allowing him complete control of this moment and of her. She wanted to beg him right here in front of the entire restaurant to take her, fuck her, make her cum until she couldn’t remember her own name.

A couple at a nearby table moved their chairs to afford a better view, the scent of sex mingling with the intense aroma of Italian food. The waiter who had enjoyed Madie previously sat at an empty table to pretend to go over his receipts for the evening all the while watching intently focused on her glistening pussy, clearly visible from this vantage point. He rubbed his erection while shuffling the papers on the table.

Grayson’s tongue darted in and out of her mouth, keeping a smooth rhythm with the finger on her clit. His other hand reached up and tugged on her nipple chain. She squealed with pain and delight, overcome with sensations. Lightly kissing across her soft cheek to her ear, he nibbled her lobe.

Breathing in deeply tickling her ear with his wiskers, “I can smell your arousal. Are you ready to cum for me?” His fingers massaged her pussy, teasing her clit with a quick flutter. The flicking increased building with her orgasm. Grayson watched as her gray blue eyes glazed over and she bit her lower lip, a sure sign Madison was about to cum. She never could hide her emotions from him. Madie wanted desperately to cry out her desire.

His mouth sought her lips and sucked on the same lip she’d just bitten. Grayson bit her lip and his fingers dove deeper into her twisting and sliding along the sensitive walls. Without removing his mouth from her’s, “Now. You may cum for me now.” Mumbled into her mouth he bit her lip once more and reached to pull and hold her nipple chain as he felt her cunt walls contract and pulse, rippling over his fingers still moving around inside her. She cried out oblivious to the attention she’d drawn. Her auburn hair feathered over his shoulder as she tossed her head back against him.

Grayson knew her body well and stopped moving his fingers inside her to enjoy the effects of her orgasm dripping on his hand and between her thighs. As her breathing began to slow again, he moved his fingers within her once more, immediately extracting another orgasm from her. He continued this five times. Madison, completely lost in the lust filled moment rode each wave of pleasure valiantly. Grayson looked into her eyes as he made her cum once more, drinking in the expression on her face and the passion in her eyes.

He pulled his fingers quickly out of her noting her disappointment and brought them to her thick pouting lips. He eased them into her mouth urging her to taste her cum on his hand. Her tongue darted around his fingers suckling the juices he’d drawn from her. Signaling to the waiter who’d been caught staring, he ordered another bottle of wine.

“Now about the proposal I told you to bring with you.”