Pausing to collect his thoughts at the door to the local cafe, he wondered what he had gotten himself into. After years of prowling online fetish forums, he’d finally found an amazing, dominant woman. He’d spent the last three months absolutely glued to his cell phone as his every activity was interrupted by his need to respond to her every text. As their conversations went from sexual to work-related to sexual and all over the place, he’d felt a connection he’d never felt before. In years of trying to find a good fit, well, he finally had found it. The cafe’s door handle felt cold and heavy in his grasp. He couldn’t believe he was about to meet her for the first time.
Jostled out of his inner dialogue, Joshua was surprised to see a tall, blonde woman waiting to enter the cafe – the door to which he was standing in front of. He gave her an embarrassed smile and stepped aside as he opened the heavy door.
She gave him a hurried smile as she walked through the proffered entrance.
He gave himself a final once-over in the distorted view the glass door offered before striding into the cafe. Attempting to look confident (and realizing he was probably failing), he took his place in line behind the tall blonde. Despite his attempts to keep his eyes glued to the menu, he couldn’t help but glance around the cafe. Was she here? He was ten minutes early, but that didn’t mean she wasn’t even earlier.
And yep. Shit. She was already here. He knew his choice to look around the coffeeshop was a poor choice for his nerves when he made eye contact with her. Her eyes met his, and she didn’t look away. Her lips curved into a predatory smirk as she raised an eyebrow at him. The coffeehouse’s branded cup sat next to her open book, and her long, brown hair cascaded down her shoulders. Her thick thighs overflowed the edges of the wooden chair beneath her. Now he felt overdressed in his button-up shirts and dress slacks next to her t-shirt and jeans.
Joshua whipped his head around to find the barista staring at him, the empty two feet in front of him looking like an obvious sign that he hadn’t been paying attention. Well, maybe that’s why she had been smirking at him. He tried to push her from his thoughts as he stepped towards the counter and profusely apologized before making his order.
Unfortunately, with the order out of the way, he’d need to walk towards the pick-up counter – and closer to her table near the corner. Would it be awkward to just wait for the drink without introducing himself? He figured he should say hello first, but he wasn’t really sure he was ready. After a mini argument with himself, Joshua figured he’d have to introduce himself sooner or later. Filling his lungs with a deep breath he didn’t know he needed, he strode over to her table. Despite his appearance clearly within her peripheral vision, the woman’s face was still stuck in her book, her brunette tresses hiding her face from view. Should he speak up? Should he interrupt her? Was it just better to be patient? God, he hated first dates.
Time passed as slow as molasses while he waited, and he felt the nervous goosebumps prickling his forearms. Finally, as his patience was reaching its limit, she slipped a plastic bookmark into her book, gently pressed the book shut, and raised her eyes to meet his own.
His name was a greeting and a statement all in one. Those three syllables held so much hidden meaning that he couldn’t even begin to unpack while he was expected to hold up a conversation. A smile, though. He could do that much.
She returned the smile then raised her hand in a dismissive motion.
“Go pick up your coffee, and then sit down to properly talk.”
He didn’t need to be told twice. He scurried off and was thankful when the coffee was slid across the counter a few mere seconds before he made it there. Slipping aside the cardboard sleeve encasing the steamy cup, he ensured the coffee was meant for him before taking the branded cup back to her table. Back to her.
Placing the cup onto the wooden table, he soon followed suit, and sat before her. His thighs suddenly ached with relief from the shaking he hadn’t realized they’d been doing. Sitting felt like a luxurious pleasure – even if he was far from the relief of this first date going well. Who knew just getting to the table was going to be such a field of potential landmines?
The conversation started with stilted pleasantries. They both were still new to one another, and the conversation didn’t flow comfortably. There was a few awkward pauses here – a few stuttered answers there. As the minutes passed, the conversation slowly started to flow better, and he found himself entranced with her answers. All that mattered was the next words from between her lips – and providing an answer that put a smile or thoughtful expression on her face. Before long, the first-date jitters turned into all the excitement and attraction they’d both felt during their months of texting. What a fucking relief.
“My coffee is empty,” she noted, sadly. Though no command passed through her lips, he saw her expression and her pointed gaze as she lifted the cup towards him.
“Vanilla latte with non-fat milk. Same size.”
While he didn’t quite jump up, Joshua certainly didn’t linger, and soon found himself back up at the front counter with another order. He made sure to keep an eye (and ear) on Cassandra’s whereabouts as he placed the order and then wandered back to the order pick-up spot to await her coffee. He wanted nothing more than to prove his obedience and ensure the fire he was feeling went both ways. All of those intimate texts about their kinks and desires came flooding back to him, and he angled his hips to hide the erection he was sure his brain would be giving him any second now. All those things she loved. All those things she wanted him to do…
The small motion didn’t escape Cassandra’s scrutiny. The novel long forgotten on a corner of the table, she’d been watching her potential submissive carefully. While he appeared to be casually waiting for a drink, she saw the way he rocked on his hips. She noticed as he angled towards the counter, and she especially paid attention as his hand slipped into his pocket to readjust his dress pants.
She bristled as a hunched woman destroyed her uninterrupted gaze. Begrudgingly, Cassandra dragged her eyes to meet the sparkling eyes of this older lady.
“I wish my husband would behave like that. That one’s a keeper.” The elderly woman gave her a gum-toothed smile which the dominant woman returned in kind. The subsequent blush that blush that crept up her “husband’s” cheeks gave her a thrill of satisfaction as the elderly woman walked away. I guess he had heard that not-so-discreet display.
She was treated with a few more minutes of peaceful studying of this intriguing man before the barista shouted out her potential submissive’s name, and within a few seconds, he was back at their table – with a noticeable flush on his cheeks. Well, now seemed as good of a time as ever to turn this a bit more….fun.
“You seemed to really like the countertop,” she teased with a smirk.
The room seemed to get smaller around him, and he felt his eyes widen with the blatant and public statement about something he considered so private. Yet he couldn’t deny it. He felt the press of his loose dress pants against his erection, and being so vulnerable was so arousing – and definitely very uncomfortable. He found a pleasurable, private joy in the fact that he found the discomfort pretty hot too. Maybe he was meant to be a submissive.
“That doesn’t sound particularly convincing. Or a good way to address a Mistress.”
His eyes were like small, flying saucers now, and he didn’t think he could get any more surprised. As discreetly as he could manage, he tried to glance around him and see what other patrons were within earshot. As far as he could tell, they had privacy for at least two tables’ length around them. Maybe this corner table had been a strategic choice. The fact that she had been planning to embarrass him in public like this made his cock pulse.
“Yes…Ma’am,” he stuttered out feeling his face running as hot as a thousand suns. Surely everyone could see how flustered he was – even if they couldn’t hear the conversation. The arousal, embarrassment, and new experience was a heady cocktail that was spinning out of control much too fast – and he wasn’t sure he minded.
“Much better,” she said with a smile.
“Now….” She crept a hand across the table to slide over the retrieved coffee, but she allowed her fingers to lightly sweep across his hand as she did it. Drawing the coffee back across the table, she brought it up to her lips, allowing her powerful silence to thicken the air between them. She felt powerful like this – knowing he was hanging on her every word and waiting for the next syllables to fall from her lips. She let the silence settle between them, building the anticipation for her next words before dropping her voice to a softer timber.
“Do you remember when we talked about how much you enjoyed the idea of discreet public play?”
Of course he remembered. She’d brought it up last month while he was attending a get-together for a friend’s job promotion. As he answered her spitfire texts, over and over, he found himself trying to hide behind furniture – and even making excuses for why he was unable to move off the couch. The entire night still stuck out as a giant, erotic tease, and he’d be lying if he said he hadn’t jerked off in the bathroom mid-party when he couldn’t take it anymore. So, yes, of course he remembered.
“Yes,” he stated – and then caught himself. “Yes, ma’am.”
His correction brought a wide smile to his tablemate’s face, and he was glad he’d managed to remember.
“Good boy,” she murmured before tearing her gaze away from his. Reaching behind her, she grasped a purse over the chair’s back and slid it onto the table in front of her. She instantly began rummaging around in the large bag. The submissive did his best to avoid craning his neck to try to see inside that large, secretive bag. He even managed it. A few seconds later, she pulled out a small, black, drawstring bag and placed it on the table as she unceremoniously swung the purse back onto its storage spot.
With a smirk, the small bag was decisively slid across the table towards him.
“So, what do you think that is?”
He took a few moments before sliding his hands to meet hers on top of the little bag. Within seconds, he had a very good idea. Sliding his hands around the satin, he felt the item’s short length. One end was pretty round while the middle part of the object was really small. The other side of this short object was thick all over again. Could it…Could it be a butt plug?
The realization hit him with a new wave of arousal, and he was hard all over again. He was even more aware of the woman’s fingers against his own as the plug slid a little bit closer towards his side of the table.
“You’re going to go the restroom. You will insert it, and bring back the empty bag as proof. I’m not requiring any photos….this time.”
The idea that she’d make him do this again added to the arousing haze overtaking him, and he felt the tiny tremors of his thighs as his nervousness over this daring plan settled into the deepest corners of his mind. Before he lost his nerve, he gripped the bag in his hand, slid it towards himself, and stood, marching off to the unisex restrooms in the opposite corner of the store.
Don’t turn around. Don’t turn around. He cajoled himself to avoid her gaze as he walked away – though he was distinctly aware of every part of her presence. His nerves only relaxed once the heavy wooden door was locked tight behind him – sealing him into the well-lit, spacious bathroom of the coffeeshop.
His hands in a deathgrip over the frigid porcelain of the sink, he studied his reflection. He was sweaty, and his arm was visibly shaking. Choosing to slide this butt plug in felt like the first real step in his kink journey. He’d fantasized about this journey for years, but fantasies and reality didn’t always mesh up so well. Was he ready for this? Was he ready to finally act out all of those fantasies that had always been so safe in the confines of his mind?
No, he wasn’t really sure, and it terrified the hell out of him, but one step at a time. Inserting a plug didn’t seem that hard, and he was in the safety of a coffeeshop. He’d never get to try any of it if he didn’t put himself out there. He was going to do it.
Emptying the bag on the sink, he was happy to see that she’d included a travel-sized bottle of lube. Was she this thorough about everything?
After using the toilet and thoroughly washing his hands, he set about inserting the plug. He’d done this more than a few times with his stockpile of toys in the privacy of his own home – but never in a coffeeshop bathroom and never at the command of a beautiful woman who was waiting on the other side of this door. The situation compounded itself in his brain causing his cock to throb in a way that was all-encompassing. There was no resisting the urge to stroke himself a few times, but conscious of the woman waiting for him, he was forced to tear his grip away.
Rubbing the rigid length of his cock had fueled this erotic blaze even further – but it also had helped relax his body. Covering the plug in lube, it inserted easily. Months of play with anal toys had clearly paid off, and she had been conscious of the plug’s size before casually requiring his compliance in a coffeeshop. Slid in to the hilt, the plug didn’t stretch him, but there was certainly no way he was going to forget its presence. Plucking up some paper towels, he mopped up the excess lube from his skin, and he readjusted his clothes. With a final washing of his hands, he left the restroom.
Every single step was a new experience. He felt the luscious pleasure of the plug sliding against his sensitive skin with every step. Was he walking funny? Was his erection too obvious? Did everyone know what was going on? He was suddenly very conscious of the near-empty satin bag he was holding in his hand. Focusing on placing one foot in front of the other, the walk back to her table seemed almost like a cross-country journey, and the relief he felt when he slid back into his chair was almost palpable.
Greeted with a raised eyebrow, the submissive man quickly placed the satin bag on the table. With a few quick pats of the bag, that assertive smirk of hers came back, and the satin bag was taken, once again, out of his sight.
She then launched into a series of questions. More like an interview than a conversation, he found that she kept supplying the next topic of conversation after the previous one had finished. It hardly left any time for him to contemplate the sensations filling up his entire lower body. The dominant woman’s lips occasionally took a break with a sip of coffee, but the questioning was relentless.
Despite the odd conversation style, Joshua found himself entirely engaged. She led the conversation – just like she had led his decision to slide a plug into himself in the middle of a crowded coffeeshop. He just hoped that his feeble answers were enough to keep her attention. With the constant throbbing in his ass and his cock, he wasn’t sure how well he was holding up his side of the conversation. It was a constant battle not to grind against the chair for more sensation – or to see if his dress pants could provide any relief to the constant pressure of his cock. All he knew was that he wanted more of this, and he had a feeling this “conversation” was her way of determining if he was worth it.
Finally, she paused her barrage of questions and just looked at him. Despite the nerves that were buzzing around at a zillion miles an hour, he didn’t dare interrupt her hungry gaze. The silence between them became almost too heavy to hold as he waited for those next syllables to pass through her lips. He was all-too-aware of the throbbing of his cheeks against the wooden seat beneath him, and there was no resisting the urge to subtly shift his hips against the chair to feel the plug respond within his body.
“Do you want more?” she purred, keeping his gaze. He lost the eye contact battle as she slid her tongue over her lower lip, capturing every second of his attention. Prey. He felt like prey, and she was attempting to hunt him like a lion who hadn’t had a dinner for weeks.
“There isn’t much more we can do here. But I’m heading to my car, and here is my address.” The dominant woman slid a business card across the coffeeshop table – reminding him of the sensuous promise the butt plug had delivered only minutes before.
“I’m heading out. If you show up wearing that plug today, we can talk about more play. If you’re too nervous to jump into something so suddenly but would love more dates, that’s okay too. Just don’t show up today, and feel free to shoot me a text message, and we can continue chatting. But today, I’m just in an awfully excited mood, and I’m really desiring a beautiful man like yourself to torture. So if you’re game, I’m game.”
With that, Cassandra stood and took the two steps to reach the other side of the table. With her breasts almost at eye-level, it took all of his self-control to look up into her demanding eyes.
“The choice is yours, Joshua. No pressure either way. I’m interested in going as slowly or as quickly as you’d like. A woman just has urges sometimes.”
She kept his gaze as she whispered out these words. Ending her statement with a wink, Joshua’s gaze followed the brunette as she walked out the coffeeshop door. He fingered the sturdy business card in his fingers: her full name, address, and phone number. He pulled out his phone to ensure those digits matched the ones saved in his phone, and sure enough, they were a perfect match. Every part of his lower body was aware of his frantic heartbeat – thanks to that butt plug she had effectively slid up his butt. He certainly wanted more, but…was he ready for more?