Claiming Zander: The First Date

Moving the Party

Pulling into the hotel, the parking lot was nearly empty. The parking lamps glowed in the slight drizzle, making the ground look as though there was a sheen of crystals across it. As the lights danced with each raindrop, the two of them parked and Zander walked over toward Ashley’s door.

She hopped out, sliding her bottom down the edge of the seat as Zander reached out to catch her. “Careful Miss, it’s slippery out here today.”

As his hands grabbed her hips to catch her, she smiled, Ashley felt the warmth in her chest grow. ‘Chivalry isn’t dead after all’, she thought.

As she caught her footing and stood in front of Zander, he began to retract his hands, ‘No!’ She thought, holding them onto her hips as she leaned up to kiss him. He didn’t hesitate and leaned in. It was more than a kiss, it was fiery and passionate yet romantic and familiar. Zander wrapped his arms around Ashley’s back, pulling her in tight as she placed her hands on his chest, kissing each other deeper into a state of embrace neither wanted to part.

Ashley pulled back, catching her breath momentarily, “It’s freezing out here, Let’s go inside.” She whispered.

“Lead the way.” Zander pointed with a smile, holding his arm out for her to hold.

Sliding her arm into his, they began to walk across the parking lot, in her comfort and passion, Ashley laid her head down on Zander’s shoulder taking comfort in his gentlemanly nature. ‘This might be the right man after all.’ She couldn’t help but feel drunk with excitement at the idea. 'But can he handle what’s next?’ Her diabolical grin was hard to hide as the hotel doors slid open.

“Welcome! How may I help you?” The front desk manager boasted.

“Checking-in.” Zander replied.

As the men covered all the typical hotel paperwork and got the keys situated, Ashley watched and listened. Getting to see Zander interacting in person finally was a sight she’d been excited for. ‘Such good manners. He sure is handling himself well with that cage and plug. Maybe those should be a more permanent fixture of his wardrobe… How cute would it be to send him to work everyday with a plug and cage, sitting through his day and meetings feeling my touch every time he moves.’ The thought made her chuckle and squeeze his arm. Automatically, Zander’s hand reached for hers and squeezed it back. The gesture made her smile. He was deep in conversation and focused on something else but he hadn’t for a second forgotten the lovely woman standing next to him.

“Enjoy your stay.” The voice popped Ashley out of her daydream.

“Thank you.” Zander replied as he took the keys and handed them to Ashley. He placed his free hand on hers and they walked to the elevator. Just then Zander had a heart-sinking realization. She had left her purse in the car, her purse that had his chastity keys in it. ‘No expectations but to please her.’ He thought to himself, causing him to smile ear to ear as he looked over at her. ‘God she’s amazing!'

Waiting for the elevator seemed to take forever. Both of them were oozing with impatience and could barely keep their hands off each other. And yet something felt odd as well. Neither of them could put their finger on it until the elevator door opened and they climbed inside. It was the tension of new things and things to come. They were both so excited, they couldn’t seem to control themselves.

Zander reached and pressed the top button, 10th floor. As the doors began to close, Ashley turned to him, kissing him deeply while taking off his belt and opening the front of his pants. Reaching inside, she began to massage his bulging trapped c**k inside its cage, making it ache and throb to be set free. Biting Zander’s lip caused him to let out a slight whimper of pain and pleasure at her touch. Zander had to fight every thought he had to prevent himself from diving his hands into her clothes. He knew better and he wasn’t going to make such a mistake so soon. His knees weakened with her every touch and his mind raced to regain control of himself.

“It’s going to be a long night for you, Zander.” She whispered as she massaged his scrotum before she pulled her hand out, patting the front of his pants as she did. “Down boy.” She smiled and laughed.

Zander reached down to close his pants.

“Don’t you dare!” Ashley’s voice was sharp and playful as the elevator came to a stop at their floor.

“Miss Ashley?” His face showed a look of confusion.

Once again, her hands were down his pants but this time was different. She pulled his caged c**k and balls out and let them hang in front of his open fly.

“Let’s go to the room.” She kissed her fingers and pressed them to the leaking head of his hard c**k.

With a gulp of anxiety, Zander followed her out of the elevator and down the hallway to their room. His head darted around looking for security cameras and other people in the hallway, his heart was beating so loudly he was certain Ashley could hear it.

“Calm down.” She had noticed his anxious look. “There’s no one here but us and your shirt covers most of you. Calm down, let go and do as you're told.”

At that command, Zander’s head spun, ‘She’s right, calm down and do as I’m told. She’s in charge, this night is for her pleasure and to prove I deserve a chance with her. Focus!’ He put himself at ease knowing she would only do what’s good for him and make him a better version of himself, her version. With that thought, a smile crossed his face again.

“Good boy.” She turned around and kissed him quickly at the same moment she smacked his balls dangling outside of his pants. “Don’t question me again.” She placed her finger over his grimaced mouth and spun around to head toward the room.

Zander had finally began to walk normally as they reached the door to their room.

Ashley stopped at the door and turned around to him, “On your knees.” Ashley pointed at the ground in front of her.

Without hesitation, Zander knelt down in front of her, placing both hands on his knees, palms up as a sign of submission.

“Such a well trained boy. I’m glad to see you’ve been doing your homework and practicing for me.”

Zander looked up at Miss Ashley and smiled, but in this position he knew he was only allowed to talk when given a question of command to speak.

Looking down at her creation, she couldn’t help but feel proud of what she’d done. When Zander and her had first started talking online just a month ago he was assertive and always trying to get the last word in, untamed and overly eager to get his fix. Now he was different, he was more calm and patient, he followed directions and only had to be told what to do and what was expected once. He no longer pushed and tried to get his way. ‘I guess ghosting him for a few days when he had misbehaved really did a number on him. At least he’s a quick learner.’ She knew it had as her phone had blown up for those days. First there were messages of frustration for missing her but soon they turned into messages of longing and desperation. From then on he had daily devotionals to her he must perform and tasks to complete. And every day, he did them all without complaint or hesitation. She knew he had completely submitted to her even before they’d ever met tonight. This night was a test of his conviction, truly it was a a test of their compatibility.

Looking up at her, Zander had an overwhelming sense of calm and belonging. He knew down to his core this is exactly where he wanted and needed to be and this was the woman he craved in his life. The joy was clearly visible on his face, washing away any embarrassment he might have at his position, he didn’t care if the world saw.

After a moment taking in her creation, Ashley moved her boot under Zander’s still leaking c**k and began to rub the toe of her boot across the head and opening. A sheen of precum glazed her boot. “Clean it.” She commanded.

Without hesitation, Zander got down on all fours, lowered his face, and licked his mess from her boot cleaning every inch of the top of her foot. The salty taste of himself filled his mouth, a taste that, through the time, training online had become second nature to his s****l desires. Ashley had trained him to never waste a drop of what came from him. The taste made him feel submissive and relaxed. Just doing the task as instructed made him feel like he was where he belonged.

As the taste turned from his saltiness to the taste shifted to that of leather, she lifted her boot, forcing Zander’s chin upward to look her in the face. Seeing her smile made him feel warm all over, filled with a sense of pride for being so obedient. Her eyes glowed down on him with radiance from her excitement to see such a happy submissive in his place.

Turning away, Ashley slid the key in and pushed the door open gesturing for Zander to enter. Not thinking about it, he crawled into the room on all fours, receiving a ‘Good boy’ smack on the ass as he crawled passed his Mistress.

“Get naked.” She commanded, still holding the door wide open.

Zander hesitated, looking out into the hallway. “Miss…” he began to mutter but was cut off.

“Do it now or go back into the hallway and get naked there before returning.” Her kind demeanor was instantly gone and her eyes looked as though they had turned completely cold and dark. ‘If he thinks I’m playing…’ She thought to herself. Just as the thought crossed her mind, Zander stood and began unbuttoning his shirt and sliding his boots off at the same time.

“Good!” But this time it didn’t sound like she was happy or satisfied, more of an annoyed response to his insubordinate delay.

As Zander began to slide his pants off, Ashley walked around the room to inspect the place he had chosen for their first night together. It was nice. The entryway opened up to a dining area with a solid oak table and four sturdy yet plushly covered chairs. She rocked one and found there was no give in them at all. ‘That will do nicely.’ She let herself start to fantasize about tying him to the chair and teasing him to no end until check-out and let out a small chuckle.

After the dining area was a small living room with an oversized tufted couch and chair sitting opposite a large flat screen television with a very large ottoman nestled between them. Along the wall was a desk and chair which looked brand new and untouched by other guests. ‘So many places to tie him up. Teasing him in the chair, cuddling on the couch, or punishing him over the ottoman. So many choices.’ She was starting to feel the wetness between her legs grow again. Walking a bit further around a corner she found a four-poster king-sized bed on risers that set the edge of the bed just at waist high. ‘Perfect! Now that’s a bed we can enjoy!’ She began to feel the same fire as before, building inside her, needing to be let out.

As she walked back over to Zander, she found him exactly where she had left him. After undressing, he hadn’t moved an inch except to fold his arms behind his back as she’d trained him. Noticing his compliance to her ungiven command made her walk to him a bit more seductively. Moving her hips from side to side with each step, knowing how many times Zander had expressed his amazement at her curves and body, she had to torment him with every step. She could see his cage twitching up and and down as his c**k bulged against its steel prison, unable to stand to greet her.

As she walked over, she began to fantasize about taking him to the bed, throwing him down and uncaging him. Slowly teasing his c**k, kissing and licking all over it as her hands wandered his body. Then stripping herself down ever so seductively as he watched, not allowing him to help or touch her. Until finally climbing onto of him and feeling his swollen head rubbing against her engorged c**t, sliding across getting her closer and closer. Then in one motion, taking him in, his c**k fill her as she began to ride him. She would start slowly to tease herself and feel him grow even more. Until her excitement had reached a point she knew she couldn’t come back from until gradually riding him harder and hard, faster and faster to her own orgasm with no regard for his pleasure.

“Mmmmmm…” a slight groan slipped from her lips as she got closer to her evening’s toy.

“That looks so tight.” She giggled coming out of her fantasy as she leaned in and wiped the precum from the tip and slowly slid it into her mouth.

Zander’s mouth opened wide with passion and yearning for her, “It’s very tight Miss Ashley.” He whimpered.

“Excellent!” Giddiness engulfed her face.

Walking around to his back, she began to inspect his entire body. Her hands roamed about him like someone with a new toy, wanting to intimately know every inch. Her light touch gliding down his defined back, passed his shoulder blades made his body shudder. The hair on his body began to stand with anticipation for her hands as they strode about and down onto his perky ass.

SMACK!

Her hand cracked across his ass to ensure he was still paying attention. The wince he let out ensured he was. With a smile she reached down lower under his ass with both hands, one grabbing his balls and pulling them back toward her while the other massaged the large plug buried in him. Zander leaned forward catching himself as he began to moan uncontrollably.

“Did I find your spot..?” Her voice trailed off as she herself began to breathe heavier and heavier in her excitement.

“God, yes, Miss Ashley. Mmmmmm…” he could barely speak the words before she pressed harder and deeper into him and pulled tighter and further than before. The mixture of pleasure and pain was intoxicating and his body began to grind toward her uncontrollably.

Her massage was intoxicating, she began to massage faster and faster while grinding her pelvis against his firm ass. She could feel her panties weren’t able to soak up all of her wetness as her hands ravaged his body. She pulsed forward into him, then bent him over laying her head on his back, sinking her teeth deeply into his flesh. She couldn’t help but mark him as hers. She wanted him and she was claiming him.

Taking a deep breath, Ashley released his balls and slowed her hand massaging the plug. Wrapping her free hand around his body, she stood him back upright and bit him a second time. This time harder, she wanted him marked for weeks. The moan Zander let out was followed by his hand on her head pushing her into him as if to say thank you for marking him, he wanted to be hers and needed the feeling. At that, she raked her finger nails down his side and released her mouth, “Did I say you could touch me?!”

“N-n-no Miss Ashley. I-i-i’m sorry. I could’t help it.” He stammered.

In a single jolt, Ashley spun him around and smacked him across the face leaving a hand print on his cheek and Zander seeing stars for a moment.

“Don’t let passion cloud your judgement, you know the rules and you know your place, right?” Her tone commanded an answer.

“Yes Miss Ashley. I’m sorry. I’ll be better.” He was shocked by her demeanor. She was clearly displeased with his actions but at the same time very pleased by his enthusiasm. The confusion in his eyes said everything to her.

“I’m not mad, it’s wonderful how much you want me. But disappointing you forget your place. There will be times when I want you to take me, but they will be rare and you will learn to know what leads up to that. Until then, you are mine! And you will behave accordingly. Am I clear?” She spoke to him as if she were speaking to a bad pet, educating them on what they did wrong and what they need to fix. Zander knew this was the only warning he was going to get and it was only happening because it was their first time together.

“I understand Miss Ashley. I am yours. I am at your command and mercy. I am for you to use. You are not for me to use but for me to obey.” He recited this mantra as if rehearsed for days, in part because he had dreamed of this connection with a woman his whole life and she, Miss Ashley, was the one woman to whom he truly felt he could connect and submit. All his dreams were standing before him.

“Good boy. Now come over here.” Ashley began to walk toward the couch, swaying her mesmerizing hips with each step.