Sweet Pain

"That's what caught my eye," Madelaine said. "It stood out."

"I guess that means I get to be the lucky one this time."

"Yeah, but you make your own luck."

"Don't we all?" he asked, once more sipping from his glass, a gesture Madelaine repeated.

"We're flirting right now aren't we?"

"And having good conversation," said Wayne. "Multi-tasking."

"Mmmm," Madelaine said while nodding. "Should we dig a little deeper then? I mean if we're going to avoid dancing around things maybe that should include where we met, at least virtually. I mean, it's not like it was Christian Mingle. Though honestly you're probably going to fine way bigger kinks there once you start digging."

"Ha!" he laughed, deep and genuine. "Fair point. But, as I see our server is coming, how about we give him our order, then we can get into the nitty gritty of getting down and dirty?"

Madelaine agreed and shortly after the server took their order of what Madelaine assured Wayne was the biggest nacho platter he'd ever seen that had vegan queso to die for. He took her word for it and the server said it'd be right out.

"You know a lot of times guys who aren't vegan are hesitant to trust me," Madelaine said. "Like somehow I'm going to secretly order them nothing but bean sprouts using super secret vegan Morse code with my blinks or something. Because that's the vegan agenda of course; bland unseasoned vegetables for every meal."

"I'm familiar with the manifesto," Wayne joked back. "I learned a long time ago, defer to the experts. You're the vegan, I'm not so my tastebuds are in your hands."

"I like that," Madelaine said. "I don't know, I always expect someone who's more on the dominant side side be...resistant to help. Not always the case of course but it's happened enough to be something that crosses my mind every time."

"Not my style."

"Then what is?" she asked with a smirk and raised eyebrow.

"I think I'm fairly ordinary outside of the bedroom. But if we're focusing strictly on the bedroom, I want to be clear about one thing. That thing is dominance isn't overbearing. It's not threatening. Personally when I hear what some do in that position without being asked to or having it made clear the sub is in to it doesn't sound like dominance to me, it just sounds like someone wanting to hurt someone else and call it sex. I prefer pleasure spiked with pain. Just the slighting tinge. Like the salt on a margarita glass."

"Exactly," Madelaine agreed.

"It sounds like every page turned to is one we're both on," Wayne said. "Promising. Of course it also helps that I'm enjoying just talking to you in general."

"Thank you," she said. "You're not exactly boring either. I really do find the whole toy sculpting thing interesting. I mean some of the stuff my friends have, I kind of get lost in looking at them. I love catching all the details. Like a good painting."

"Maybe I'll show you some of my work some time," Wayne said. "I get comps of it. I don't really put it on display because that just seems gauche but I could dig them out of storage if you ever wanted to see. Though not tonight. Inviting you over to my place seems a little forward right now."

"Well, let's just see where things take us," Madelaine said, letting a little bit of her Cheryl Blossom flirtiness sneak out. She agreed with his assessment of course but that didn't mean they couldn't be just a wee bit playful about it.

The playfulness continued through the night of shared nachos. Though the end goal both parties had in mind for this outing was simply finding out if there was enough chemistry there for a sexual partner for a few romps. As hours went by like minutes however, both were discovering something a bit more stable than a fuck buddy.

Still, the pair went Dutch on the meal, Madelaine Venmo'ing the cash to Wayne before they left. Wayne however insisted on handling the tip, which was fine with Madelaine. When she noticed he overtipped, she knew this was going to be something more than a round of fuck and run when it got to that point.

"Want to take the same cab?" Wayne asked as they headed for the exit. "We can even stop by my place first if your nervous about a stranger knowing where you live."

"Well you're not really a stranger anymore, are you?" Madelaine asked with friendly and flirtatious tone. "Yeah, I'm cool with that."

It didn't take long to hail a cab once they were outside. It was an SUV number and both got in the backseat of the car. After getting both their addresses, the cabbie was off to Wayne's place first.

"You know I really don't mind if you see my place," Madelaine told him as they headed off. "I mean I'm pretty confident that's going to end up being a destination for you at some point."

"Really?" Wayne asked. "I did that well?"

"Flying colors." Madelaine answered.

"Then I suppose this isn't an issue." Wayne leaned over and pressed his lips to Madelaine's, a gesture returned and added upon as she insisted on tasting his tongue with hers.

"Far from it," she said as he pulled back, licking at his lips before they were too far away.

"Then I also hope this wouldn't be too out of place." Wayne placed his hand on Madelaine's thigh. She looked up at him, the brown eyes giving off a very green light message. As his hand went further up the smooth skin of her leg her red lips turned up into a grin. She was about to speak when he shushed her.

"Act normal, Madame," he said, her screen name sounding even more sexual when she heard it come from his authoritative yet-whisper quiet voice. "As normal as you can. Look ahead, look all around...but don't let him know...this is for us. Understood?"

"Yes," she said.

"Yes what?" His hand was up her skirt, his fingertips just barely touching the damp spot quickly forming on her panties.

"Yes...yes sir." Madelaine turned her focus ahead just as the idea of her trying to not sell what was going on. The gentle touch of his fingers on her thigh. They danced there briefly before pushing her panties her panties aside and getting acquainted with her velvet depths.

Madelaine bit her lip and tried to choke on the moan that was desperate to come out. Two of Wayne's fingers were inside of her, conducting a symphony of pleasure inside of her. He may have played as though everything was casual but Madelaine could quite literally feel how his attention was 100% her...or maybe the mathematically impossible 110% as she felt his thumb begin to play with her clit.

The smile gave it away. The barely there smile. He knew full well what he was doing to her, what Madelaine desperately wanted to do. He knew she wanted to lay down and let him have his way with her, back of a cab or not. She wanted to scream in tongues of her passion. Instead, she was doing what he told her, as best she could. This was her test as the dinner was his. And it was straight A's so far. Sure, she shivered when he got her in just the right place. A tiny moan sometimes escaped from between those luscious red lips, but it was stifled. She was looking forward, doing everything in her power to play it as normal as possible while melting in his hands. Just watching her he was sharing many of her urges. He couldn't wait to make her melt in his mouth as well.

Madelaine ached for this as well. Every cell of her being screamed for her to lay back and let Wayne have it take, to take her in any way he wanted. But she didn't. And not for the obvious reason. Sure, she was in a taxi and while that was certainly on her mind it was the main reason. That was that Wayne had told her different. Wayne had told her to act normal. To not sell for a moment how good he was making her feel. She was doing all right, though a couple things slipped that Madelaine was able to cover as a cough or yawn. As Wayne turned up the heat on her however she must have seemed dead tired to the driver during a yawning fit.

"I bet you want to cum," Wayne whispered in her ears. Madelaine turned to him, her lips pursed tightly together as she nodded in return. "I'm going to let you...just not yet." Wayne then turned his attention to the driver. "I'm sorry, we must seem like total asses being so quiet and all."

"Nah, not at all," said the driver. "Most people just stare at their phones anyway. No skin off my back but thanks anyway."

"Must drive you crazy sometimes," Wayne said, his fingers continuing in their quest to make Madelaine squirm and shiver. "You know, all the silence."

"You know I see where you'd think that but honestly it just gives me a lot of time to think. I mean now that's there's GPS and all that I don't even need directions or nothing so it's pretty much all me, myself and I. Get a lot of good thinking done."

"I bet." Wayne replied. He continued his conversation with the taxi driver while his fingers operated with surgical precision within Madelaine. The skilled way in which his thumb pressed her button and his fingers waltzed within her, how he hit every sweet spot in her liked he choreographed the dance ahead of time was making the struggle to contain the pleasure a full on war.

A pause in the conversation brought Wayne's full attention back to Madelaine as his lips back to her ear.

"You'll get to cum soon," he whispered. "I promise. You still want that, don't you?"

"Yes sir," she whispered back.

"Good. I just need to ask you one thing."

"W-what is it?" she asked, her eyes on him. "What is it, sir?"

"Do you want me to kiss you?" Wayne asked, his lips barely containing his smile.

"Yes sir." Her full lips were met once more with his as his fingers began to work their magic on her g-spot, casting a spell of pleasure that was fixing to rock her like she hadn't been rocked in far too long.

"You can cum now," he whispered once more. "But...keep it quiet. We don't want our friend in the driver's seat to know, do we?" One more kiss and Wayne turned his attention back to the driver, though that was only surface level as Madelaine could feel within that she was the recipient of his focus, falling deeper into the fog of pleasure her was leading her into.

"Looks to be getting close to the first stop huh?" Wayne said, Madelaine on the edge of orgasmic oblivion.

"Looks like sir," the driver said, oblivious to the situation behind him. "Any second now."

"Sounds about right," Wayne said, flashing a grin at Madelaine who at this point couldn't help but at the very least breathe deep. Anything could push her over the edge at that point and anything did. The cab slowed down to take a speed bump, however what speed couldn't do gravity would take care of with the sudden rise up and down hitting a Konami code inside of the redhead, unlocking everything that had been building up in the fifteen minute cab ride.

Her mind, body, and soul all wanted to cry out in that moment, but she held it for Wayne and his smile made it all worth it as her cunt constricted and squeezed around his fingers. Her pale skin flushed and pink, sweat on her brow, Madelaine was out of breath and exhausted from both the orgasm and herculean effort it took to hold it all in.

Wayne withdrew his fingers from the ginger's snatch and brought them to his lips, sucking them clean, which made Madelaine's hunger grow once more. However, reality was about to intrude on that.

"First stop," the driver said, pulling up to Wayne's apartment building.

"That it is," Wayne said,. He gave Madelaine a kiss goodbye. A quick one, but still enough to taste herself on his lips. "So, see you next week?"

"Definitely," Madelaine said with a big smile. "Can't wait."

"The feeling is very mutual." Wayne got out and handed the driver some cash. "That should cover myself and the lady. Whatever's left, you keep it."

The driver looked at the hundred dollar bill in his hand. "Uh, you know what you gave me, right?"

"Yep."

"Well all right," said the driver. Wayne then gave Madelaine a wink before he entered his building.

As she was driven back to her place Madelaine knew it was going to be a long week. Wayne had left quite the impression. And while it was a long week, it wasn't quite what Madelaine expected. She and Wayne and exchanged numbers and he had called her the next day. His voice calm, but assertive and it made Madelaine melt like butter.

Under his careful direction she masturbated for him. He directed her very movement during these calls. Never harsh nor a cross word but Madelaine knew when he hit a certain tone of voice, a calm and soothing authorty, that she would do whatever he said because it was guaranteed to make her feel something beyond words.

On her couch, in her bed, in the kitchen, in her car before driving to her personal training session, and finally on the bathtub. It was almost upon that one week mark and he was given her one last bit of aural pleasure before things got very real between them once more.

"Ohhhhh Goddddd," Madelaine cried out. While the taxi had its unique charm, the at home sessions meant she could more full enjoy herself with Wayne, even if he was a few miles away. She reclined in her large tub, breasts just below the sudsy water of the bubble bath she was submerged in and her hand between her legs, working her pussy to Wayne's explicit directions.

"Feels good doesn't it?" he said, voice emanating from Madelaine's phone, resting the wide lip of the tub. "Tell me."

"Yes...yes sir it does," the redhead moaned, eyes shut tight as the turned her own dial all the way. "Oh....oh my god.....so good...."

"Do you know tomorrow you're going to feel even better?" he asked. "I can guarantee you that...you just have to do one little thing for me."

"Anything sir," she said, desperate pleasure in her voice.

"I need you to not cum tonight." He said. "I need you to stop right now."

"But..."

"I thought you said you wanted to feel even better than you do now?"

"I do..."

"Then do as I say and I guarantee it."

"Yes sir," Madelaine said, pulling her hand away from herself.

"Don't be so glum. It will be worth it. Don't you trust me?"

"Yes sir," Madelaine said. "I trust you."

"Then know I'm not lying. I only have one last request. Well two, honestly. You can call me by my name now."

"No problem Wayne," she said with a smile, her voice getting casual once more just as his was now. "What's the other thing?"

"Tomorrow, I want you to wear that outfit from your profile. I want you in that."

"Mmmm, nice to know you enjoyed it."

"I can't think of anyone who wouldn't," Wayne said. "So, we on?"

"Like you wouldn't believe. See you then. Bye."

"Bye." The line went silent and Madelaine reclined in her bath, tense from the ending that wouldn't come until the next night but relaxed beyond belief. She couldn't wait for what the following night would bring.

While the night wasn't exactly sleepless, it did take a little longer than usual for the redhead to drift into slumber without the release she was expecting. She told herself something even better was coming the next night and that positive affirmation helped. Though it wasn't so much an escape as it was a slight numbing of her desires. Her dreams were filled with images of what might be. And though her fingers wandered between her legs, even in slumber she kept her word to Wayne.

Sleeping in fact was the easy part. Once she woke up and had her shower and matcha tea the waiting game went into hard mode. The clock even seemed to jump back a minute or two as she waited. Finally it was 4:00, two hours before she had to be over to Wayne's. Close enough to the event that she could start getting ready.

Shower, make-up, hair; she took extra care with it all. Just the right lavender scented soap, the perfect shade of red on her lips and getting every hair just where it needed to be. Then came the outfit. Piece by piece she put it on, finishing up by zipping up her thigh high boots and fastening the choker in place. The last non visual piece of the puzzle was a light spritzing of perfume, just enough to play with the lavender scent from her bath. Sure by the end of the night she's most like be a laughing, sweaty heap, dick drunk with hair all over the place but just because a gourmet meal was going to leave behind an messy plate didn't mean presentation didn't matter.

Everything looked perfect and she looked at the clock. 5:15. It was time. She put a coat on, covering the outfit and grabbed her purse, smiling wide the entire short trip to her car. And that excited smile didn't fade, even in L.A. traffic. Now time seemed to go by in a flash.

It was 5:45 by the time she made it to Wayne's apartment. She pulled into his parking garage and handed the guard her ID as instructed and he gave her a guest parking pass and gave her directions to the assigned spot. Once she parked her car and set the pass in the windshield she headed out towards the elevator, barely able to contain the excitement she felt. She was already wet, desperate to see what he had in store.

Time slowed down one more, teeter tottering like mad as her craving grew. The numbers on the elevator seemed to take forever and a half to change until finally she hit Wayne's floor and walked to his door. Her knocks sounded thunderous in her ears, like time had finally slowed to a complete crawl until she her the door unlock and open, revealing Wayne behind it. He was dressed far more formally than their first date. Black jacket, white shirt, black tie, even his hair was far more coifed and in order. She liked it and the aura he projected, the authority...the dominance.

"Well hello," he said. "Come in." he held the door open for her and once Madelaine was in he shut and and locked it behind her. She took in his place. It was sizeable for an apartment. It was pretty much a loft for all intents and purposes. There were a few unique aspects to it, as in the redhead's experience most lofts didn't have closets or cupboards. His kitchen was unique as well, though not anything she hadn't seen before. It had all the usual things, but also had a flair to it with a higher cabinet and barstools along it. It all seemed to fit though, especially with the assorted posters on the wall among the other knick knacks.

"Hope being early isn't an issue," she said, removing her coat and showing him the outfit that caught his eye live an in person as an added bit of punctuation.

"I'd rather have you early than not at all." he replied.

"Good call." She smiled at him, taking a seat on one of the barstools and laying her coat on the one next to her. She loved these few moments before the real action started, a few fleeting moments of being the one in charge before giving herself over to someone else.

"Can i get you something to drink?" Wayne asked, heading to the kitchen. He went to cupboard and took out two glasses then opened the fridge. "Nothing alcoholic though. I don't really think that's appropriate, to be honest. I want any inhibition you let go of to be 100% of your volition."

"How gentlemanly. What are my choices?"

"Mainly juices and La Croix. I'm just going to have some plain club soda with a bit of lime."

"Sounds perfect." Madelaine said. Drinks were poured, lime was added and the two toasted to the night ahead. Madelaine licked her lips after the first sip, the light tartness of the lime delightful. Then Wayne walked back around the bar to face Madelaine, give her something beyond the club soda when he placed his lips to hers in a deep, sensual kiss. "As was that."

His eyes connected with hers and the switch was flipped. Conversation could wait. There were far more pressing matters to deal with.

"Would you like to see something fun?" Wayne asked.

"Yes," Madelaine said.

"Yes what?"

"Yes sir." She smiled at him and he returned one right back at her. She spun on the barstool in the direction he walked. Wayne went to a wardrobe near his bed, opening it up and taking a shiny wooden box out of it. Her eyes widened in anticipation of this new mystery.