It was a beautiful morning on the Great Lakes as the sun rose over the treetops. The crisp air was making her nipples hard; they were rubbing blissfully against the inside of her flannel shirt. She was enjoying a cup of coffee in her room before making her way down to the casino floor. She contemplated her wardrobe to accomplish her two main goals for the day - ease of access was the first. She did not want to be too encumbered when playtime finally arrived. The second goal was to show off her deep cleavage to help her finish seducing her suitor.
Wendy settled on the classic "little black dress" for her outerwear, and her favorite pair of black lace panties with a wide waist band. She would not be wearing a bra today. "Free the nipple!" she thought to herself and let those thoughts wander toward the future. What would the day hold? Would she be successful in her personal mission?
Wendy unbuttoned the shirt and tossed the flannel into the suitcase, and watched it land on top of the cuffs and restraints she brought with her in anticipation of her evening.
Jim spent the better part of the morning driving toward the casino on the lake. He was a little anxious because he was speeding so as not to be late. His mistress demanded punctuality, and he did not want to disappoint her. It would be the first time they met face-to-face, and he desperately wanted to make a positive first impression. He pushed the pedal down and raced his way up the highway. His thoughts began to consume him, and he wondered what lay in store for him.
Jim had never experimented with bondage or submission, but it was something that seemed to call to him. He relished the idea of pleasing his mistress and being rewarded for his obedience. As the miles ticked past him, his anticipation built proportionally. He was no more than 10 minutes away now, and he was practicing his greeting when his cellphone rang.
"Hello, this is Jim," he said.
Wendy answered him with, "Hi Jim, it’s Wendy. Are you close? I am getting hungry!"
"Yes, I am about 10 minutes out. I should be there a few minutes early, Mistress," he replied.
She let out a sigh and said, "Good, I do not like to be kept waiting. I will go ahead and get us a table, just meet me in the restaurant, please."
"Yes, Mistress. I'm hungry too, though I don't know if I will be able to concentrate on breakfast with you there." His voice betrayed his desire to prolong their introduction. He was lusting for her.
Sensing his tension, Wendy reassured him, "Don't worry, Jim, we are going to need plenty of energy if we are going to get through the rest of the day." She said it as much to commit her resolve as she did to ease his mind. "I'll see you when you get here, and Jim, do hurry." And with that, she hung up the call.
Jim pressed harder on the accelerator and heard the engine rumble in response. He was really pushing it now and prayed there were no police between him and the casino.
As he rolled up to the casino with a few minutes to spare, he tossed the keys to the valet and asked, "Can you point me toward the restaurant?"
The young man deftly caught the keys in one hand, jerked his thumb back over his shoulder with the other and grunted, "Straight back that way."
Jim took the extra few minutes to duck into the nearby bathroom to quickly freshen up and check himself in the mirror. After a quick coif, he took a deep breath and deliberately slowed his pace out of the bathroom.
Wendy was seated at the table facing the entrance to the casino so she could see him arrive. She checked her watch as he strutted through the door and made a mental note that he was exactly on time. As he walked up, she stood and greeted him. "You're right on time, Jim. Please have a seat. I took the liberty of ordering you a cup of coffee, they serve it in individual French presses here. It's divine."
Jim nodded his head in thanks and moved behind Wendy to push in her chair as she sat down.
"Oh, such a gentleman!" she exclaimed. "I do love a man with manners."
Jim let himself relax a little and slid into his chair. He placed his napkin into his lap and took a moment to drink in the sight of her. She looked well put together without trying too hard, and the smoothness of the dress let him admire her full hips. The cut was so low in the front that he felt a slight vertigo trying to see to the bottom.
Wendy cleared her throat and said sharply, "My eyes are up here." She laughed when he snapped his head up so fast that his grey hair fell over his eyes. She was only half-kidding, but she needed to establish that she was in control.
"Yes, I'm sorry. I lost control, please forgive me," he begged.
Just then, the server showed up with a glass press full of dark rich coffee, and a tall glass of chocolate milk.
"Do you take milk and sugar in your coffee?" the server asked him monotonously.
"Yes, both please." he answered her. He noticed the small jug of real creamer, and the option of raw sugar on the tray and was grateful for the high-quality offerings.
As she set the accoutrements down on the table, she absently asked them, "Do you know what you would like to eat?"
Jim nodded in deferral to Wendy and raised his eyebrows.
She spoke up immediately, "I will have the BLT with an over easy egg on the side, and he'll have the steel cut oatmeal with butter and honey." Her voice was steady and even, and the server glanced up at the role reversal, but said nothing as she wrote down the order. When she walked away, Wendy spoke up.
"I hope you don't mind me ordering for you, but I remember you mentioned that you were a fiber for breakfast kind of guy, so I ran with it," she said flatly.
Jim replied with a rising tone, "I don't mind at all! Why would you think that?" With that, he winked at her and let a grin form across his lips as he said. "Where you lead, I will follow."
"This is going well," she thought to herself. "If he picks everything up this quickly, we are in for some real fun later."
He sensed her approval and decided not to let there be a lag in the conversation. "Do you have any plans for anything specific while you're here? I read there is a spa, 18 holes of golf, and there is always the blackjack table - or do you fancy poker instead." He raised one eyebrow when he said "poker" and drew it out, so it sounded more like "poke her."
She looked at him with a stern mocking smile and replied, "I have some plans, but they don't involve the spa, the greens, or the tables. I was thinking about something more 'off the cuff' and trying to 'harness' some energy in my room upstairs."
Jim immediately understood the double entendre and involuntarily let his lower jaw drop. She saw this expression, and knew that she had picked the right sub.
The server brought their food, and they both ate without saying much - chewing, sipping, and stealing glances to try and get through breakfast as quickly as possible. As Jim was finishing the last sips of his coffee, Wendy reached across the table and grasped both of his forearms, trapping them on the tabletop. She lifted her foot and placed her heel squarely between his legs and against his balls. She looked him directly in the eyes and asked him point-blank, "Are you going to obey my every command, Jim? Are you willing to trust me?"
He returned her whisper with his own, "Yes, mistress. I trust you, and I am willing." His heart skipped a beat, and he felt the hair on his arms stand on end.
She felt his goosebumps, and licked her lips devilishly and said, "Good, now let's go up to my room so you can show me."
She put both feet on the floor, and he practically jumped out of his chair to pull back hers as she stood up. He reached out his hand, and she took it in hers as they turned to walk out.
As they walked through the casino, the bells, dings, and cheers were a cacophony in their ears. It sounded as though the entire place was celebrating for them as they passed.
They reached the elevator just as a couple of well-dressed men were getting off and they slid inside. When the doors closed, they faced each other.
Her voice pierced the silence, "When we arrive at room, there are some things I want you to take off, and things I want you to put on. Listen carefully and obey."
He nodded his head and replied, "Yes, mistress. I listen and obey." His mind was racing - not about what to take off, but about what to put on. He knew she wanted to dominate him, but he had never done anything like this before. The thrill of the unknown was giving him butterflies, and he chastised himself.
They got off the elevator at the top floor, and she opened the door with the flash of a key across the handle. The room was an enormous suite, with a picturesque view of the golf course below and the trees beyond that. It was like something out of an expensive oil painting hanging in a museum.
She broke him from his musings with another command. "I want you to remove everything below your waist but take your time while I watch."
Jim bent down to untie his black wingtips and kicked them off near the bed. He was over six feet tall and exercised regularly, so his toned muscles rippled as he unbuckled his belt and stood on each leg to remove his slacks. He hooked his finger into the tops of his socks to push them off his feet. He stood there with a partial erection in his button-down dress shirt and nothing else.
"That's good, now let me help you get these on." She walked behind him with a set of wrist restraints. "Give me your hands," she told him, and he dutifully put his hands behind his back. He heard the crackle of the Velcro as she loosened the cuffs to slide them over his hands.
Wendy was starting to get turned on while restraining him. She placed the wrist cuffs over his hands and pulled them tight before fastening them. She walked back in front of him and admired her handiwork. He looked positively enticing as his erection continued to grow. It was not the longest or the thickest, but it was definitely something she could work with. She put both hands on his shoulders and pushed him down onto his knees.
Jim was rippling with expectation. Not being able to use his hands only seemed to heighten his other senses. He could smell her musk permeating the room. He could see every freckle as she lifted her dress over her head. He watched every resonating ripple as her breasts bounced, and her nipples tried to dance off her chest. Then, she placed her hairy mound directly in front of his face and grabbed two handfuls of his graying hair.
"I'd like you to lick me and suckle me, Jim. I want you to get me off with your mouth and tongue. I will guide your head, and you will control your tongue. After I have had my first climax of many, we will try something a little more... challenging. Can I trust you to please me, Jim?" she asked as she peered down into his eyes, not breaking their gaze.
His only response, low and needy was, "Yes, mistress." He leaned forward to begin, and she promptly smacked him across the cheek with her palm.
"No! Remember, I control you. Me," she snapped.
He was startled by the contact, but it didn't hurt him physically. He told himself to pay closer attention and be an obedient lover. He slowly opened his mouth and stuck out his tongue.
Wendy ran the fingers of both hands through his hair and swiftly jerked his head forward to plunge his tongue firmly into her slit. The heat of his breath echoed the heat in her loins. The soft sounds of him lapping up her juices caused a low moan to escape her throat. She used her hands to rhythmically move his head back and forth to tongue-fuck herself.
Jim felt the urgency in her grip on his head and started to time his tongue thrashes with her thrusts. He heard her gasp and knew she approved of his actions. Suddenly, Wendy stopped thrusting his head and just held him tightly against her slippery lips. He took it as a sign to focus on her swollen nub and began to work on suckling her clit and flicking it with her tongue. A low, rumbling hum escaped her mouth and she whispered, "Oh my God, yes. That's it - right there. You're going to make me cum, Jim."
Wendy let her head fall forward and took two full handfuls of Jim's hair and clenched it tightly as the spasms started to wrack her body. Her legs suddenly went limp, and she let herself sit fully on Jim's face while he supported her whole body on his face and chest. Her thighs were shaking, and her gasping breaths were ragged and urgent. She was yelling, "Fuck! Oh God Jim. Jesus, yes!"
Jim felt a rush of warmth as she squirted while writhing all over his face. It rolled down his chest and dripped off his balls to the floor. the sensation made his cock jump with stimulation, and he smiled inwardly at her complete satisfaction. He heard her sigh and gently shift her weight back onto her legs as she stood up.
"My God, you have performed very well! You made your mistress squirt all over you; you will be handsomely rewarded for that, Jim. I would like you to stand up now. We need to control that cock of yours. I need it rock hard for me." He saw her turn around and shuffle through her suitcase. She pulled out a cock ring and grabbed his shaft to push it onto him. She pushed it down his shaft and pulled his balls through the loop. Immediately, she could see that it was the perfect tightness. His head started to slowly levitate as the blood rushed in with no way to escape. Wendy leaned forward and whispered in his ear, "I have something else for you, so we don't disturb the neighbors."
Wendy slipped the ball gag over the top of his head, and he opened his mouth willingly to accept his restraint. She ensured that it was tight enough to stay in place and then reached down and picked up a riding crop from under the bed sheets. It had a small triangular leather flap on the end of a slender flexible shaft. She told him, "Turn around for me, Jim. You've been so good, I am going to reward you with a spanking."
Jim hummed behind the gag and turned around, flexing his butt for her. He felt her push him over and he tumbled forward onto the bed. With his arms still restrained, he had no way to catch himself as he flopped onto his chest with his ass hanging off the side of the bed. He felt her use the crop to softly rub across his cheeks as she adjusted her stance just to the side and behind him. He felt a puff of air as she whipped back the crop and then heard a sharp crack as she swung it forward and popped him squarely on one ass cheek. Instantly the pain was sharp, but it quickly faded into a heat that spread out over his backside.
Wendy giggled deliciously as she saw him jump at the contact and watched the red triangle begin appearing on his firm skin. His legs were muscled, and she could see the rippling in his legs as he kept himself on his feet. She drew back for another and aimed for the opposite side. She flicked her wrist and saw the rod bend in slow motion as the tip whipped back and then forward to make contact. There was a satisfying whack as she watched him jump again. She felt her own body heat rise, and her wetness started to drip down her inner thigh.
She continued like that, alternating sides for several more strokes until Jim's ass was fully red and inflamed and she saw him adjust himself on the bed. His erection was full now, and Jim was trying to keep himself comfortable.
Wendy stopped swinging and told him, "Jim, you are not allowed to come until I tell you, okay? I will let you know when you can, and I promise it will be satisfying. Do you understand?"
Jim nodded his head confidently, but he was worried about how long he could last. He was already at peak stimulation, and it would not take much to push him over the edge. He willed himself to get it under control and focus on pleasing his mistress. He felt her grab the wrist restraints and pull him to his feet again. She walked over to the in-room fridge/freezer and pulled out a large, frozen buttplug.
"I want you to watch me put this in, Jim. Think about your cock sliding into my ass as I do." She licked the plug, bent over in front of him, and slid the icy head into her ass. She shivered at the cold but delighted at the stretching of her tight hole. Once the plug was in place, she knelt in front of him and started to insert the very tip of her tongue into the hole in the head of his cock.
Jim moaned from behind the gag and closed his eyes. He was going to need to concentrate if he was going to last. He felt her tease his head and run her tongue around the tip before licking up and down the length of his shaft. She cupped his tight sack in her hands and played with his balls as she took the length into her mouth and sucked slowly.
Jim was aching now and had resorted to reciting different portions of literature that he had to memorize for his schooling: selections from Beowulf, Shakespeare, and The Gettysburg address had all been running through his mind. As if she knew what he was thinking, Wendy stopped sucking on his cock, grabbed a bottle of KY she had stashed on the bed, and spread a healthy amount of lube over his rigid member. She bent over on the floor in front of him on her knees and elbows.
Jim watched as she pulled on the flared base, and her puckered hole stretched over the plug until it popped out. Wendy placed her head on the carpet and raised her ass high in the air.
"I need you to fuck my ass now, Jim. Come over here and give me what I need." She wriggled slightly in front of him - beckoning him toward her hips. With no hands to help him, Jim placed the tip at the entrance to her tight, and now very chilled hole and she pushed back to allow him to enter her. The combination of the coldness of her cheeks and ring versus the heat of her insides was a thrilling contrast.
Jim let her set the pace as she rocked back and forth on his cock. She was cooing now, and he saw her reach back and start to massage her lips again, using her fingers to spread them open and push inside her slit.
"I want us to come together. It won't take long, and I want you to pound my ass hard when you do. I need you to do that for me." She maintained control of the thrusting as well as his satisfaction with the tone of her voice. He had no choice but to obey her commands.
Jim started to sway in the rhythm of her hips and relished the sounds of the sloshing and slapping of their bodies together. He could feel her furtive hand movements through her thrusts and felt them speed up little by little. He was thankful that she was getting close because he was losing control. His only focus was on their physical connection and the convergence of their movements. The cock ring had him engorged and flaming hot, and watching himself disappear and reappear at her ass was mesmerizing.
When he thought her hands were moving at supersonic speeds, he heard her shout, "Jim, I'm about to cum! Are you ready to pound my ass? I want you to fuck me as hard as you can!"
Jim exhaled roughly and began to push his hips forward with all his strength, and he heard her shriek in pleasure. She pushed back against him in equal measure and started to moan intermittently.
The waves of orgasm started to break over her and she was lost in the sensation. The heat in her ass was searing as she felt every thrust stretching her wide. The thrumming in her clit was popping and crackling with sparks of fury. Her body was thrashing involuntarily, and all she could hear was the ringing or her orgasm. She was sure that she was shouting but could not truly know.
Jim heard her wail, and that was enough to send him over the edge. He was pushing his cock as deeply as he could, and the smacking of their bodies was loud and raucous. He joined in her exuberant cries and felt his balls tighten as he spilled his seed into her ass. The release was both satisfying and electrifying at the same time. Wave after wave of cum shot through him.
Wendy felt the gush of warmth fill her, and that feeling lifted her again with another gush of her own. She sprayed her orgasm onto the carpet beneath her and let the spasms take control. With her ass full of his cum and her hand covered in her own slickness, she allowed herself to relax and fall forward in exhaustion into the puddle she created. She could smell the confluence of her juices and their sweat mingling. She could feel the dribble of his cum starting to fall down her crack to mix with hers.
Jim kneeled there for a few minutes, panting and watching his cock bounce as the last drops of his semen slid down his shaft. He saw the white dribble slide out of her ass and between her swollen labia. They were both spent for the moment and needed some time to regain their senses.
Wendy broke the silence with these words, "You were VERY good today. You did exactly what I asked, and I am sincerely thankful for it. I am going to take those cuffs off you so we can get cleaned up. I was thinking of a trip to the spa to help us relax and recover before we try something else later. Would you like that?"
He nodded in reply, and she heard a muffled, "Yesh mithtresh," from behind the gag.
