Living His Fantasy Pt. 02

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She finds new ways to torment him.
5.3k words
4.62
11.6k
8

Part 2 of the 2 part series

Updated 06/09/2023
Created 10/28/2018
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LittleKay
LittleKay
308 Followers

Lane sat at his desk at work on Thursday morning, finally just about back to normal. Or at least, his ass didn't hurt. The color from the bruising was yellowed and fading. He spent the entire day on Monday trying not to shift or seem uncomfortable. But his arse had still been so fucking sore from his weekend tryst that just sitting was turning him on. He spent as much of his time that morning on his feet and walking the office as possible, but he realized he was making his employees nervous. So sheepishly, he took an agonizing seat in his office.

There was a knock on his door, and his secretary peeped in. His eyes stuck a little too long on her grape purple colored stilettos, before looking her in the eyes. "Sir, are you ok?" she asked him. "You seem nervous this whole week." she bit her lip - his crotch stirred- and he shook his head.

"Er, no. Yes. No, I'm fine, just a little... er, sore."

"Worked out this week?" she said with a smile. "I didn't think that would make you sore, I see you jogging every morning." Suddenly, her face turned ashen and her mouth gaped like the cutest goldfish in the world. "I-I mean... I'm sorry, y-you... I don't follow you, Sir, you run right by my apartment building." she stumbled over her words. "O-on the w-way to South Park..." she cleared her throat, smoothed her hands down the front of her dress, and awkwardly excused herself.

Lane raised his brow, the ache in his ass in the back of his mind. She watches him? After all, she'd have to be looking out her window every morning 2 hours before work started to notice such a pattern. The thought made him giddy; he did always think she was attractive. Maybe...

The afternoon wore on and he looked down at his phone. He and Mayra, the woman who... indulged him over the weekend... had exchanged phone numbers before she left his hotel room. But she never did message him. He bit the inside of his cheek. He was seriously on this fence? To text, not to text... should he do it first? If he didn't, would she at all? If she didn't, does it mean she doesn't want to talk to him? But what if she was more ashamed than he was? He ran his hands through his hair and picked up his phone, staring at a blank NEW messages box. He hesitated, wrote "hey", all lowercase, casual, not even a period, and sent it. Then he threw the phone away from him. He felt like a schoolboy, texting an older girl who waved to him in the hall.

His phone pinged, and he looked down; she replied, and within minutes too. he picked his phone up eagerly.

[ Who is this? ]

His heart sank. He put the phone down, head in hands. She seriously hadn't even bothered to take note of his number. Had their night been that forgettable? His phone pinged again.

[ Kidding! Took you long enough, stranger ]

He sighed with relief, a smile cracking at the corner of his mouth, typing in his own reply.

[ I wasn't sure how to follow

up with you ]

[ Well, when you open up a phone, there's a

new message button... ]

He smirked. She had humor. He wondered if it was to make him feel better.

[ Yeah, I've figured it out...]

[ So, I was thinking maybe

we could have coffee ]

[ Well that's boring. ]

She really had no respect for his heart health. Which was as healthy as could be but he still felt as if it would fail at any moment.

[ How about dinner? ]

[ Did you have a place in mind? ]

[ Well, you're paying ;) so I figured

I'd let you choose, I don't want

to make you spend too much. ]

He smiled. She was being considerate, which he admired, but money was no object.

[ Well, do you prefer Italian, Chinese,

good ol' fashioned steakhouse? ]

[Hmmm, I could always use a

good steak. ]

[ tonight? ]

[ Well, do you need time to

debate on how to use a GPS

to pick me up? ]

[ You've got jokes. :P ]

[ Watch it, or I'll put that tongue

to good use. ]

[ 7pm is when I'm free. ]

He turned red, and sent a confirmation, with a "Yes Ma'am" for good measure. He called out to his secretary, asking her to make a reservation for him for 2. He thought he noted a bit of dissapointment on her face, but if she was upset that he had a potentially persona dinner date, she hid it well. He picked a place that was nice, with linen tablecloths and had great steak, but wasn't so strict on a dress code. He didn't want to scare her away. He often met clients there, and has gone out with his father to dinner on occasion.

---------------------------------------------

Lane pulled up to the townhouse 5 minutes to 7. He rubbed his hands on his jeans, nervous, looking up to the lit windows above. He could have sworn he saw a shadow move across a window, but he didn't want to be -that guy- staring. He got out of the car and approached the door, fist poised to knock, and froze. He felt himself drain of color.

He had been so selfish to trick a woman for his own desires. He already knew Mayra intimately, and it was hard enough approaching this door. To enter, being told you were being given one thing, already this anxious and to have your expectations flipped on his head.. He gnawed at the inside of his cheek. He should be ashamed of himself, putting her in such a position. He stood there like this, frozen, and the door swung open in front of him. He jumped, and looked up to meet the eyes of a beautiful Mayra. her brown hair was done in curls, bouncing around her face. Her makeup was done, and she wore a black and pearl colored dress, a silver necklace with a heart charm, and black heels. His gaze lingered on all the wrong places as he took in her appearance. He smoothed his pressed blue dress shirt, and cleared his throat. "Well... you look, er, nice." he said, smiling.

Her forehead scrunched as she looked him up and down. "You look much different, dressed and greeting me from the front." she said, smiling. He picked up on the same humor he'd seen in her texts. She was a sarcastic girl, but her words made him slowly turn red.

"I-I... Speaking of which, I-"

She rolled her eyes and pulled him over the threshold, "We can at least have this conversation indoors." she said, smirking. She stalked away from him into the kitchen, and filled two glasses with water, and handed one to him.

He looked around, taking in the coziness of the apartment. The furniture was minimal, but it was cluttered in a way; a pile of work files lay on the floor by the couch, books and a few pens sat haphazardly on the coffee table. The couch was a chocolate brown and he saw a tear in the arm. Photos of family and cousins and nieces and nephews and what he assumed were her parents' wedding hung on the wall in mismatched frames. He was distracted, and felt suddenly strange. Her home looked lived in. What would she think if she came to his? If a home was the reflection of a person, his was empty.

"You were speaking of something?" she asked.

He smiled. "How about we talk at the restaurant? We have a 7:15 and we're already going to be fashionably late."

-------------------------------------

They spoke of odds and ends as they drove; work, friends, the little stuff. When they arrived, he pulled up to the valet parking garage across the street, and he placed a hand on the small of her back as they crossed to the restaurant. He pulled the doors open and led her inside. She smiled. "Well would you look at that." she said, taking in the grand design of it all. She looked him up and down. "You look under dressed." she said. A host who recognized Lane approached him and led them to a private circular booth. They sat, and they brought water and a bottle of wine, and took their orders. They each chose to allow the chef to choose their steaks.

Mayra leaned forward, and smiled across the table. "So... How's the behind?" she asked.

He turned red, and he cleared his throat. "I uh... I wanted to apologize for that." he said. "I didn't mean to make you uncomfortable. I wasn't thinking when I set that up, and I'm sorry."

She smiled back at him. "So this is a pity date then?" she said with a smirk. "Just going to dine and leave me in the dust, never to explore the dark things you brought out in me last weekend?"

He coughed on his wine, clenching his teeth. "I uh... so... you don't regret it? You aren't angry at all?"

"Sweetie, if I were angry, I wouldn't have come out with you." she said. "I found a very dark desire with you last weekend, and I've spent time since researching the items we used together. A few days on the internet makes me no expert but I've looked up safety and health in regards to such practices. And so that brings me back to my original question; how is your behind?"

He looked down at the table and fiddled with the cloth napkin folded on top of it. "It doesn't hurt anymore. Still a bit discolored." He looked up at her as she leaned on the table, her chin propped on her hand.

"And you felt alright after I left?" she asked softly.

"I... I was ok." he said, "A bit overwhelmed."

She tilted her head at him. "I want to play again with you. But if it is too much..." she watched his eyes widen and light up. Despite being an apparently wealthy and successful man who handles himself with dignity with others, he was a puppy with her, his walls completely collapsed. She loved it. "Perhaps we can see what else you have to play with at your place." she said. "after dinner."

He smiled, and looked up as the wait staff brought them their steaks, sliced, and he pulled his napkin off of the table, flicked it open, and laid it over his lap. He smiled and nodded. "You've got me excited." he whispered. "I erm..." he reached into his pocket then, pulling out his checkbook. "I-I don't want to make you feel... don't take it in a bad way. But I promised last weekend I would pay you. I never did." he laid his checkbook on the table, his thumb ready to flip it open. "But... If we're going to continue... this..." he looked up at her, and her expression was blank. "I want to show my gratitude. A-and I'm more than willing to pay for anything if you want to get anything you find fun, or..." he didn't get a response from her, and fumbled with a pen in his pocket. He quickly flipped open the well worn book and sketched out a check, leaving the total blank. "When I told you I'd pay you, I wasn't sure how much. I would have given you anything. What do you want?"

She mulled his little rambling over in her head. He did promise. But she didn't want to feel like a prostitute or a Mistress, or obligated to him in any way. "Keep your money. If you want to buy me something nice, or something to play with, by all means. I enjoy a well thought out gift here and there. But please... keep it."

He smiled, and clicked his pen and put both it and his checkbook into his pocket. "Good..." he said, nodding. "Good."

---------------------------------------

They walked back to the car after a fantastic meal-Maya was quite pleased by the visit from the chef who wanted to make sure his food was enjoyed-and a strange silence fell between them. It wasn't awkward, but rather loaded with what they would be doing tonight.

Lane took his keys from the valet after helping her into the passenger side, taking the moment of solitude to collect his thoughts as he crossed over to the drivers side. Finally behind the wheel, he shifted the car into drive and pulled out into the street.

"So... what sort of things have you been finding that have interested you?" he asked, shifting gears as he took a ramp towards the city.

She didn't say anything at first. Then, she said in a quiet voice, "Ma'am."

Confused, he glanced at her. "Wha...?"

"You will call me Ma'am." she smiled over at him. He thought her voice had become low because she was shy, but he could hear the lilt in her voice now. She was anxious. Anticipating the evening.

And Lane felt appropriately admonished. With a heavy swallow, he lowered his head. "Yes Ma'am."

"Good boy." she said crossing her legs. Her voice was barely audible, but it made his heart race. He didn't ask further about her findings in her research, feeling quite dismissed by their small interraction. This woman... He felt as if she were natural. Domineering and on top without the stage acting. He found her so alluring that he was hard and aching in his jeans before they even reached his home.

Parking in the garage and taking the elevator up to his apartment, he was hard pressed to supress a groan as he heard her heels click on the tile of his foyer. "Ma'am..." he said again, nervous, reaching for her coat. She smiled back at him, as if she knew exactly what she was doing to him.

"My feet are a bit sore. Do you mind helping me out of my heels?" she said, sitting down in a stool at the kitchen island as Lane hung up the coat by the front door. He nodded as he turned to look at her, his mouth suddenly quite dry. "And what do you say?"

"Oh... y-yes Ma'am." he whispered, his voice cracking. Slowly he approached her and knelt down sliding a hand around the back of her calf to lift her leg gently. As if scared t touch her too much, he grasped the buckle of he heel and pulled, loosening the straps of the heels as he removed the first one. Her feet were soft and light in his hand, and he placed the shoe down on the floor with a clatter.

"Don't be shy. Why don't you show me how much you appreciate that I'm here while you undo the next one?"

Lane swallowed, and glanced up at her. His face felt warm. "H-how..." he cleared his throat. "How would you like me to do that, Ma'am?"

Mayra chuckled. "However you'd like. Show me what you would like from me."

Lane sighed, and nodded. "Yes Ma'am." he said. This time, he slipped his hand higher behind her knee, leaning his head down and pressing his lips to the soft skin of her knee. The intimacy of this moment made his heart leap into his chest as he squeezed her calf gently, kneading his fingers in the muscle as he kissed down her shin. She sighed in appreciation, and he felt encouraged as he slid his hands lower and lower, finally gripping her ankle as he popped the strap. Once there, he lifted her other foot, already bare, and rested it on the junction of his thighs. He could feel his hardon raging through the thick fabric of his jeans, practically begging to be touched by her beautiful feet.

He never did see himself as a foot guy, despite loving a girl in heels. But he would do anything to be touched by any part of her. And to prove it, as he pulled the other heel from her foot, he lifted her bare sole, running his nose from heel to toes, planting kisses along the way.

"Mmmm... that is definitely a nice way for a woman to come home from work. Hypothetically that is."

Lane smiled and set the other heel down on the floor. A groan escaped his lips before he had a chance to restrain himself, as her foot began to rock and knead on his groin. "Ah... I would love to be there to take your shoes off after a long day again sometime." he replied, dropping his gaze and locking his eyes on the way her foot danced on his jeans.

"Eyes on me." Mayra said, smiling. "Unbutton your jeans and free yourself a bit. But keep your eyes on me."

"Yes Ma'am!" he whined lifting his butt form where it rested on his heels in order to quickly unbutton his jeans. He kept his eyes on her soft brown eyes as commanded, and tried his best not to disrupt her dancing foot as he removed the thick fabric from between them. He pushed them down to mid thigh, and gave a soft moan as her warm toes spread across his raging cock.

"Oh..." he whimpered. He felt like a virgin again. He kept feeling the urge to glance down at her foot kneading his cock but he didn't want to disappoint her. He began to rock his hips against her foot, but as soon as he tried, she lifted it away. He gasped in disappointment, looking down in surprise as if he would have her touch back if only he could see it.

"Tsk tsk. Two more infractions. I didn't say you could move. And I didn't say you could look away from me." her voice was strong and commanding as she reprimanded him. Confident. But as he raised his gaze back to her face, he noted the glee in her smile. She was having fun. She was exploring her little fantasy she'd created in this past week. And she was enjoying it immensely.

"I'm sorry, Ma'am!" He planted his ass back against his heels, his hands in white knuckled fists on his thighs. He locked his eyes with hers, an obediant and eager puppy.

After a breath, her foot returned to his groin and he bit his lip to keep still, aching as he tried to absorb the pleasure he found in the increasing tempo of the dance on his hard member. He was desperate to grind against her, find more speed and friction, to end this torture.

"You will be sorry." she countered, and the promise of a punishment sent a shiver up his spine. Her toes poked into the slit in his boxers and he shuddered at the feeling of her skin on his. "I want you to stand up when I say. You will select the item you will be punished with. You will return to me here. And you will decide how many lashes you will recieve for each of you three infractions."

"Three, Ma'am?" Nervous excitement made his spine tingle.

"Three. Because I had to instruct you in taking off my shoes, did I not?" She smiled. "I'm sure such a hesitation won't happen again in the future, if I nip it in the bud now."

Lane bowed his head. Three mistakes. Mistakes he will never make again. Tonight he has learned quite a few things about what Mayra liked, and he liked them too. She dropped her foot from him just then, much to his disapointment, but a simple, "Go." released him to pick his instrument.

He considered smiply selecting a spatula from the kitchen, but instead took the stairs to the loft and unlocked the wooden chest at the end of his bed. He inhaled the scent of polished wood and leather, and selected a particularly narrow leather strap. It was looped, like one might loop a belt for a spanking, and attached to a stiff braided handle.

Rushing back downstairs, he found her sipping a glass of water, leaning against the kitchen island barefoot. She glanced at the item in his hand and her eyes sparkled. "Get undressed." was her only comment, however, and he rushed to do as he was told.

He was bare in just a minute, cock jutting out from his body, toned chest heaving with excitement. His head was bowed before her. "I didn't mean to disappoint you, Ma'am." he panted, unable to find his breath in his anticipation.

She pushed away from the countertop, bare feet making no noise on the hard floor. She pointed towards the counter, and instructed him to place the strap down on the granite surface, and lean forward to grip the edge, parting his legs. He did as she asked immediately, keeping his feet flat as he leaned forward, his shoulders flexing as he gripped the edge of the island.

"How many will you take for each transgression?" she asked him, her voice lilting with curiosity and excitement.

"T-ten is always a good place to start, Ma'am. This strap... It is harsh. It won't leave general redness like the spoon..." he paused, hesitating, as he didn't know if she meant for him to explain, but she didn't stop him. Instead, he felt her fingers on his ass, nails grazing the still slightly discolored skin. He took her silence and touch as encouragement to keep speaking. "I-It will leave welts. The thin edge will mark the skin, almost between a belt and a whip."

He heard her breath hitch, and felt her finger wander down the crack of his ass, passing over his rectum and sending a shiver up his spine. Her fingertips touched against the back of his balls between his thighs.

"And where is it best to use this tool?" she asked softly. "I wouldn't want to become overbearing on your sweet ass, as it still has not returned to normal."

LittleKay
LittleKay
308 Followers
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