Alex watched as his girlfriend clicked up the driveway to their home in her towering platform heels. Their cottage was secluded amongst the trees in northern Oregon, tucked into one of the many wooded areas of this state. The little bits of light peeking through the trees shone off her latex skirt, the same one her boss had forced as part of her uniform. This change of course was unbeknownst to Alex, of course, because it wasn't necessary for him to know anything that happened between Erin and Brock unless they chose to inform him. Or rather, Miss Erin and Mister Samson, as far as he was allowed to address them.
As Alex pulled away from the house for the thirty-minute drive to Bistro Modello, he tried to put the situation out of his head. Without Erin in eyesight or earshot, and especially without her cumming in the passenger seat while taunting his locked-up cock, this was an easier task. He approached a red light, stopped, and closed his eyes in silent thought.
Erin was right, Alex had been a busboy for a time at a restaurant, though it was long before they ever met. It was demeaning work, to be sure, but a suitable first job for a high school student. When he graduated high school, he left that little diner clearly in his rearview mirror. He only mentioned the job to Erin and Brock on one particularly degrading night, where they demanded that he tell them something embarrassing about him that neither of them knew. He immediately drew a blank, but concentration is difficult when you've watching your girlfriend get fucked by a physical specimen of a man while being forced to stand diligently with their drinks on a tray next to the bed.
It should have come as no surprise to him that something that isn't really embarrassing - taking a low-level job as a high school student - would result in tangible humiliation down the road. He felt momentary pride that they weren't making him bus the tables, but that was quickly squashed by reason. As their waiter, he'd have to check on them incessantly, perform perfectly and punctually, and disappear when they wanted him gone. He sighed as the light turned and he drove on.
After high school, Alex went directly into real estate. When the market crashed, he treaded water for a while before getting into the dangerous game of buying foreclosed properties, fixing them up himself and selling them for profit. He became very proficient at flipping houses and built a nice nest egg for himself. His affluence, he now surmised, was the main reason Erin was attracted to him in the first place. His lofty position as an officer at his real estate company meant little to Erin beyond his paycheck, and would obviously mean very little today. He bought and sold properties, transacting millions of dollars in an average week. The only difference these days was that he did it with a plastic prison firmly locked around his cock.
Brock had not only taken control of Erin's attire at her workplace, but he had also, by proxy, instilled a dress code at Alex's. The women were not permitted to wear pants, only skirts that flattered their bodies. He proofread and strictly corrected the memo he had forced Alex to write to this effect, and only after three rounds of edits with a week's chastity sentence added for each round was he allowed to send it to his company. A few employees left, but those that remained were excited by the opportunity to flaunt their assets around the office a bit more. This was, of course, all done in service of making Alex's life at the agency much more arduous and distracting.
Alex finally broke from his daydream as he saw the turn for Bistro Modello in the distance. A quaint little Italian restaurant set just outside of the busy Portland city center, it was the perfect location for a romantic rendezvous with someone you were trying to impress. That's what Alex thought when he first took Erin here, and it still held true for the rustic bistro. Deep red brick and stucco decorate the exterior with vines crawling from the roof down adjacent to the second and first-story windows. The second story is a façade. The interior opens up vertically to the roof, but from the outside it simply looks like a Venetian villa anatopistically juxtaposed against deep evergreen trees of the Pacific Northwest. Alex pulled his girlfriend's car to the front and approached the heavy wooden door, only to be met immediately by what may as well have been an actual wildcat.
She was at least eight inches shorter than he, sported long black hair tied neatly into a single French braid that extended all the way down her back. Her blue eyes pierced through his and her lips pursed. She had a runner's body, fitted into a snug white blouse and knee-length black skirt. Her skirt was snug enough to reveal the bumps of garter straps that connected to stockings, leading down to her sensible, but stylish three-inch black pumps. She also wore a pursed-lipped sneer as she took in Alex. At first glance, Alex would have guessed her at five years older than he. But as she spoke with an edge and annoyance that made him reminisce about Mister Samson's countenance, he began to realize that she was more aged than her well-kept appearance would suggest.
"Alex, right? The submissive waiter boy?" She immediately chided, setting the dynamic for what this relationship would be. This type of edge coming from a female form was new for Alex, and it, just like any stiff breeze these days, made his cock twitch in its little prison. "Staff doesn't park in front. Go around back." And she slammed the heavy wooden door shut.
Alex sighed in frustration. That type of strict, distant dominance was undeniably sexy to him. It was a place that Erin had yet to fully go. Her style was more of a sweet, unassumingly demanding girlfriend. She doled out tasks to Alex seemingly without regard for how intensely they'd frustrate him or how deeply they'd demean him. The only time she got truly mean with him was when he displeased her, and that often resulted in a simple call to Brock to sort things out anyway. And yet, a piece of him deep within craved this utter disregard for his feelings, this assumed feeling superiority.
Dutifully, he pulled his car around to the back lot. The BMW looked completely out of place as he tucked it into a small spot between a dirty, late-90s Chevrolet truck and a beaten-up Ford Escort. As he turned the car off, he noted the dust kicked up in the gravelly parking area and made a mental note to get the car washed before he picked up Br... Mister Samson. Neither he nor Miss Erin would cotton to being transported in anything that wasn't pristine.
He approached the back door and found it locked, of course, and knocked. And waited. Alex's forte coming to the fore once again. He was always waiting for something. It's no wonder he was mockingly tabbed for this particular job. Just as he was about to knock again, the door swung open and the waitress from earlier appeared, then immediately walked away. "Come on, boy, you've got a lot to learn," she tauntingly called over her back.
The kitchen was a tranquil, modern model of cleanliness and order. Everything was just where it should be, awaiting the chef and line cooks for the evening's dinner service. Aromas of cured Italian meats wafted through the kitchen and reminded Alex of just how hungry he was. He'd skipped lunch in order to make sure that the car was perfect for his girlfriend's arrival today. As it sat in the dusty employees' lot, he realized that he'd likely wasted that time and wouldn't get to eat until much later that evening.
Alex was led to a small room with a mirror, and a garment bag hung over the door by his dark-haired, pint-sized powder keg of an instructor. "My name is Sandra, but you may call me Miss Evans. You'll follow all of my instructions to the letter, or else your owners will find out what a bad boy you've been. They gave me this," she said, and he didn't even need to see it to know what it was.
