Claiming Zander: The First Date

The Arrival

As Zander pulled up to the restaurant, he began to feel butterflies deep in his stomach and a kind of nervous electricity throughout his entire body. The entire hour and half drive had been calm and relaxing with almost no one else on the road, but now, pulling in and the realization hitting him, this was it. Blind dates have always had a tendency to make him anxious but not like this. This was no ordinary blind date.

He had met Ashley on a website for dominant women to meet submissive men a few weeks earlier. It had always been his fantasy to be submissive to a woman he was with. The problem of regular dating was, every woman he’d met and dated his entire life has left him lacking that fulfillment. He had always been the dominant in the relationship. Stumbling across Ashley’s profile, she seemed like an amazing woman he thought, he just might finally be able to be himself around someone for once.

The weeks of talking started off innocently enough, discussing work, family, friends, hobbies, and the like. As they had gotten to know each other they both began to fall into their respective roles. Ashley would give him tasks to completed most days, Zander would completed them as required and send proof. Other days they would video chat with a bit more formality given their stations. In no time at all, Zander was eating out of the palm of her hand and begging to meet in person. Now that the day was here, his nerves gripped him deep down to his core.

Sitting in his truck for a moment, Zander recalled the instructions he was given for their meeting, Ashley’s voice echoing in his head. ‘Get a chastity cage that can be worn discreetly, put it on before you come to the restaurant and bring all the keys with you to the restaurant. Wear a black and red checkered long-sleeved shirt, black jeans, black boots, socks, no coat, and no underwear.’

As he climbed out of his truck, the brisk air and drizzle that came with March in Michigan hit him. It was freezing outside. With a quick deep breath, he hurried to the front door of the restaurant, felling his steel cage getting colder and heavier with every step.

As he walked in, looking around the restaurant was empty except a few people playing pool in the bar, the bartender, and a beautiful woman sitting at the bar. As instructed, he took a knee once he entered by the hostess station and pretended to retie his boot. Suddenly, a pair of legs appeared close to him with calf-length boots running up to a tight pair of skin-tight jeans. However, looking up he couldn’t see much as the woman was so close her thigh blocked his view. Instantly, his c**k strained in his cage causing him to wince as a giggle came from above him.

“Come on Zander, I got here early, I’ve been waiting for you.” It was Ashley standing over him.

As he stood, he realized the beautiful woman he saw at the bar when he came in was in fact her. He had been so nervous this whole time, he barely had time to take in the woman’s face to see her smiling at him.

“Well don’t you look nice?” Ashley chuckled. “I do love how well you follow instructions.” She added as she turned to walk back to their seats at the bar.

Zander followed. He was finally able to take a deep breath and take a moment to look her over in person for the first time. She was wearing dark brown calf-high boots over her skin-tight dark blue jeans with a hint of knit boot-sock peaking out the top. As his eyes traveled up they got hung up on her exquisite rear. Her hips swung ever so slightly side to side as she walked, creating a mesmerizing dance he could hardly take his eyes off. Her burgundy and white with blue pinstriped blue plaid button down, had a small button just at the middle of her lower back that made it rest on her perfectly curved hips with the tail dangling down the middle of her rear accentuating her hips and curves, like a flag showing him the way to her treasures. Her dark brown almost black hair was curled in loose large swoops that swung along her back ever so casually. ‘Wow! The webcam had absolutely not done her justice in the least!’ He thought as they approached their seats

“Thank you.” Zander replied mesmerized by her beauty and having no other words he could think of. “I was hoping you’d like it Ash.”

“Excuse me.” Her face suddenly went a bit stern.

“I’m sorry, did I do something?” Zander’s mind raced with confusion.

“Well since this is our first time in public I’ll let it slide, but it’s no different in public than online. You call me Miss. Remember your place.” She said as she slid her perfect ass onto the seat. Oh how Zander longed to be the stool she was perched upon.

“May I sit Miss?” Zander asked with a half grin.

“You may.” Her smile was automatic and filled her face. As her eyes lit, Zander couldn’t help but feel a sense of pride and his grin became a full smile with excitement and anticipation. He’d wanted to meet her and be in her presence since they first emailed back and forth. This was his dream come true.

“Good to see your manners are back.” She couldn’t help but smile. It was just that easy to completely take control of this situation for her on their first time ever meeting and in only a matter of minutes, they both knew she was the boss, and knowing she was absolutely in control made her wet.

She had been looking forward to this day for weeks. From the first webcam conversation they had, Zander was nothing but polite, respectful, and obedient. She had always wanted such a wonderful man in her life, one she could take and mold, but not only that, one with manners and respect but also a bit of a goofy and fun side. Truth be told, his looks weren’t half bad either. She recalled their first online chat, when she had him strip naked. ‘He was so apprehensive about being naked on camera but without a little prodding, there he stood in all his glory. His shoulders and arms were solid and well carved, his chest larger than she expected and every time she saw it she imagined touching and massaging his pecks and n*****s. His legs were well defined and led up to a nice round perky ass she always imagined giving a few good smacks. On the other side, a well defined V carved down his stomach to point directly at his well-hung cock.’ The thoughts made her shudder with excitement.

“I’ll order us some drinks.” Zander said snapping Ashley out of her daydream as he sat down.

“No need.” She replied, “it’s already been taken care of. I told the bartender that when my date gets here to bring him 2 shots of whiskey, a whiskey and coke, and an old fashioned for me.” Her sly smile reached ear to ear as the bartender walked over and poured their drinks.

Looking at the drinks as they sat in front of him, Zander’s mind went back… ‘This is like the night we video chatted and she made me drink all night. Well, I wouldn’t be here if I didn’t trust her already, plus I can’t say no, she’s the boss, so here we go I guess.’ “Salute.” He cheered with a smile and tossed the first shot back.

It was far stronger than he expected. He was usually a mixed drink or wine guy, not one to shoot whiskey. But the burn in his throat was quickly quenched by the joy on Ashley’s face at his obedience and complete submission, even in this public place.

“Good boy!” She grinned and took a sip of her drink, “Delicious, want a taste?”

Zander knew this was less of an offer and more a command as he took the glass and took a small sip.

“That’s not enough to taste it. Here.” She pushed the glass back to his mouth and held as he took a much larger mouthful.

“It’s good Miss. Thank you for sharing.” He slid the drink back over. Ashley smiled as she began leaning over sliding her hand up Zander’s thigh, grabbing his cage. He let out a large sigh as the cage suddenly became unbearably tight.

“You went with a steel cage is see… Wonderful!” She elated. “Did you bring all the keys”

“Yes. I’m glad you like it Miss.” Zander’s words were short and his breath heavy trying to get the words out. He couldn’t help but watch her hands trace over each bar of the cage and down to the tip. The jean material felt rough but exhilarating on his c**k between the bars as she pressed and massaged the cage. “Good, give them to me.” She reached out her other hand on the top of the bar and waited.

Zander's heart raced as he reached into his pocket slowly. He’d only ever worn a cage on his own, never for anyone else. The excitement of giving her control was undeniable, as was the nervousness in his stomach. ‘Am I actually going to give her all the keys to my chastity cage?’ What if she… His thoughts trailed off as he felt her fingers tracing over the head of his c**k through the bars. He pulled them out and placed them in her waiting palm.

“That’s all of them?”

“Yes Miss Ashley.”

“Good.” Her thumb ran over the keys as her fingers closed around them.

“It better be!” She snapped with an instantly stern look darting at him.

“Uh oh.” Ashley giggled, dropping the keys into her purse still rubbing his c**k. “Someone is excited. You’re making a mess.” Her gaze had adjusted down at the crotch of his pants, to the spot of precum that was now visible on the front of his jeans. She reached with her other hand, took his hand and pulled it between her legs, “I guess that makes two of us.” The fun had gotten her so wet he could feel its through the crotch of her pants, the wet, warm, humidity that was unmistakable.

Feeling her, Zander’s c**k sprang against the cage, bulging to the point he let out a strong sigh of pain.

“Don’t worry, you’ll get to taste it soon enough. Take another shot.” The look of excitement and fun was all over Ashley’s face. Tonight is going to be a night we will never forget. She thought almost out loud.

“Cheers!” Zander clinked glasses with Ashley and tossed the next shot back.

Zander’s face jerked at the shock of the whiskey snapping him back down to reality causing Ashley to laugh so hard she almost fell out of her chair.

“No wine for you tonight.” She barely squeezed out catching her breath. “Don’t worry, I won’t go too hard on you.”

Zander smiled as he caught his breath, the shot still tingling in his throat.

“You’re such a good boy Zander.”

“Thank you Miss Ashley.”