Cuckold stories

Miss Erin's Homecoming Pt. 02

by gelir

07/17/2016 23:47 in humiliation


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 fa├žade. 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.

Brock had developed a 'Report Card' for Alex for when he and Erin lent him out to people for their amusement. Such as the time they forced him to work as a gas pump attendee all day, buttplugged and wearing a humiliating sign that said 'I didn't keep my Mistress's car on Full.'

The Report Card included metrics in the rubric like Enthusiasm, Protocol, Speed, Accuracy and Appreciation. Each category was scored out of five, for a possible score of twenty-five. Erin, surprisingly, had come up with a few novel ways of turning a non-perfect score against Alex in the past few weeks. That's how he'd found himself impaled on a dildo in their basement, chained so he was crouching down and writing lines while he was forced to listen to recorded audio of his girlfriend getting pounded by Brock. Each point away from perfect resulted in twenty lines to be written based on the category where he was docked.

Enthusiasm - 4 out of 5. "This worthless slave will be eager to complete any tasks deemed too asinine for a real man." Twenty times.

Protocol - 5 out of 5. Thankfully, Alex was always good at addressing his betters with respect.

Speed - 3 out of 5. "When this slave is slow, he wastes the time of all those superior to him." Forty times.

Accuracy - 4 out of 5. "Those superior to this slave should expect perfect execution of every silly task they assign to him." Twenty times.

Appreciation - 2 out of 5. He had let his requisite smile slip from his face for a moment and actually growled as one of the patrons at the gas station poked his ass with the gas pump. Big mistake. "This slave will show how grateful he is for his lowly station at all times." Sixty times.

A score of 18 out of 25 netted out to 140 lines being written, which took all night impaled on a meaty rubber cock while his girlfriend and bull went out dancing and he listened to the sounds he only got to hear second-hand. A man's powerful pleasure and his girlfriend's gasping acceptance of his dominance. The sounds that Alex didn't get to generate himself anymore - the sounds that existed only for his torment.

The production of the report card snapped Alex into a docile state of mind. He stood up and put on a warm, practiced smile despite the battle raging inside of him. "Yes, Miss Evans," he calmly replied to her threat. "Thank you."

Sandra smirked and pointed to the uniform hanging in the bag. "You have ten minutes to change, little boy."

'Little boy,' Alex thought, 'that's something only Miss Erin calls me.' He shook off the momentary confusion as Sandra left the room and went to unveil his uniform for the evening. It consisted of a crisp, white oxford shirt and accompanying black bowtie, along with black dress pants and polished wingtip shoes. A black leather belt and a white apron completed the standard waiter look, but as Alex removed all of it from the rack, he noticed something else.

A little ziplock bag hung from the hanger, containing a pink, frilly thong and a note. Upon opening the bag, Alex was hit with an immediate waft of his girlfriend's scent, a scent he seemingly became more and more sensitized to the more he was chastised by her. The note was in a girlish hand, and read:

'Hey there, little boy! I can't wait for you to serve Mister Samson and me tonight. Do you remember these panties? These are the ones I was wearing the first time you had sex with me. You were so nervous and cute! Your little cock could barely stay hard, but when we started having sex, you spurted immediately. So funny. Anyway, you're wearing these tonight under your cute uniform. I came in them before sealing them up so you can really feel my juices on your little twig. Enjoy!'

Being alone in the room, Alex permitted himself to groan in frustration as he undressed and slipped the panties on. A tight fit, to be sure, but he was able to squeeze himself into them. As always when Erin forced him to wear panties, the bulge created by his plastic-encased member was unsightly and obvious, but Alex was more focused on the wetness seeping through the slats of his cage. He dutifully dressed in the rest of the uniform, making sure the bowtie was just right around his neck before emerging to face Miss Evans for what was sure to be an enlightening training session.

Just outside his changing room, Sandra struck a more imposing figure than before in her own uniform. It must have been the riding crop in one hand and his report card in the other. She led him out to the dining space. Alex hadn't gotten to eat there since that date with Erin, but seeing it immediately brought back a nostalgic warmth. The deep red walls are decorated by ornate sconces, adorned with unlit candles that, along with the individual candlesticks on each table will be the primary source of light for the patrons of the restaurant.

A stinging slap from the crop on his ass brought him out of his daydream. "Snap out of it, cuckie, and pay attention," Sandra began. "This is the main dining hall, and that," she pointed with the crop to a secluded, small table set deep in the corner of the restaurant, "is where your owners will be sitting tonight." He smiled as he looked over to the table. It was the same one he and Erin had occupied on their first date. That much he had requested, thinking it would at least amuse his Mistress. He just hadn't planned on witnessing her amusement first-hand.

"As soon as we're done here you will leave here to retrieve them," Sandra continued. "When you get here, you will drop them off and go back around to the employee entrance. You'll have to be quick, as they will be waiting to give you their drink orders. And Mister Samson told me that waiting wasn't as big a hobby of his as it is of yours," she cooed with a smirk.

She waited for his dutiful and enthusiastic, "Yes, Miss Evans," before continuing.

"The order of service here is drinks, antipasti, primo, secondo, and dolce," Sandra continued as she took a seat at a table nearby, propping her high-heeled feet up on a chair across from her on the other side of the table. "Our patrons sometimes order a contorno to go with their secondo," she rattled off with years of experience backing her every word. She narrowed her eyes on the inwardly tumultuous but outwardly placid servant in front of her. "You will answer every question your owners have about each course and serve them promptly as soon as their order comes from the kitchen. Any mistake made anywhere along the line will be blamed on you, and you will suffer the repercussions of it."

She produced a menu and wine list from a nearby table, pushing them toward Alex. "You have one hour to memorize every dish that we serve and every type of wine we have in the cellar. In an hour, you'll be serving me the same way you will Miss Erin and Mister Samson. And you'd better be perfect," she teased as she tapped the report card with her pen and his thigh with her crop. "You've got a lot riding on it."

She simply pointed down to the ground next to where she was seated as an indication that Alex's study area would be at her feet. He chimed in with another chipper, "Yes, Miss Evans, thank you," before settling in next to her on his knees and beginning to pour over the provided study guides.

The wine list was nearly impenetrable, the menu fully so. The name of every dish and bottle and their descriptions were written in Italian. Alex only spent five minutes with it before realizing that his attempts to describe Tortelli Mara-Monte as 'tortelli de recotti e spinachi i salsa di calamari e seppie con panna' would get him absolutely nowhere with Brock and Erin. They'd expect deep understanding of the menu, an impossible goal but one he'd need to strive to reach regardless. Alex swallowed his pride and looked up to his cold, taunting teacher, who was currently reading a magazine with her feet propped up on a nearby chair. She hadn't dropped her riding crop yet, and was tapping it in an incessant, methodical tempo on the top of the table in front of her.

"Miss Evans? I apologize, but I don't speak Italian and neither do my," he swallowed, it was still so hard to say it, "owners. I would be of much more comprehensive service to them if I were allowed to study a menu in English, if one were available. I'd be happy to allow them the Italian menu and answer any questions they may have about the dishes, of course. Is there an English menu available that I could study, Miss?" He looked up at her with wide eyes, his voice inquisitive and naive. It belied his natural assertiveness at the negotiating table in his line of work. But he wasn't exactly negotiating from a position of strength, here.

Sandra's lip curled into a smirk as she looked down at the supplicated slaveboy, begging for a menu in English so he could better avoid a vicious punishment from his girlfriend and the man fucking her. And she decided that he would pay for such a privilege. "There is one available, Alex, but you're going to have to make my time in fetching it worth it to me. When I return, I expect you under the table with your hands behind your back."

Of course, Brock had told Sandra about Alex's finely honed oral skills as it pertained to the female form. The only way he was really allowed to be intimate with his girlfriend anymore was with his tongue, and so he'd gotten very proficient with it. There even existed, in the playroom at their house, a flipboard scorecard modified from its original purpose - 'There have been 15 days without an accident.' - to keep tabs on how many times Alex had orally satisfied Erin between his orgasms. The number sat at an even 14 now, but she had been gone for a week. As he settled himself into the required position under the table, Alex deeply hoped that the next number to appear on that sign would be zero.

Alex slide his arms behind his back, clutching his opposite elbows with his hands as Sandra returned with the menus. She set them on the table and scooted her chair forward so that her pussy was just inches away from Alex's face, and he noticed, for the first time, that she had forgone panties. Something about the fact that he was wearing panties and she wasn't thrilled him in a twisted way and made his cock bob against its prison. But then, it didn't take much to do that anymore. She reached down and wrapped her fingers through his hair to pull him forward, not going through the trouble of raising her skirt. Instead, she shrouded him in darkness as she buried him there, coldly admonishing, "You aren't allowed to see it, fucktoy, just do your job and maybe you'll earn these menus to study."

The chastised slave nodded under the material of her skirt and answered with a slightly muffled, but enthusiastic, "Yes, Miss! Thank you," before nudging his nose against her slit. In the complete darkness under her skirt, this was the only way he could scout the territory and see. A nestling of his nose against the top of her slit elicited a moan and a squirm, and the feel of fingers tightening in his hair. He dug a bit deeper, pushing aside a little flap of skin and nuzzling the little nub underneath it.

"Yesss..." came the affirmation from above, and Alex quickly replaced his nose with his tongue, pressing the flat topside of it against Miss Evans' newfound clit. His cock throbbed in his cage, but in this moment, Alex smirked in mischievous glory. For as long as he was allowed down here, in whatever context Sandra allowed, Alex, for a brief moment, had power over the situation. He rolled his tongue over her clit, flicking it with the tip and pressing the underside to it. His chin nuzzled into her slit below, collecting some of the juices from her pussy as they began to roll out. The rubric of his Report Card quickly flashed into his brain.

Enthusiasm and Appreciation. He moaned in response to her, thanking her with a muffled mouth. His words were not designed to be understood, but to simply add to the sensations. His deep voice rumbled against her sensitive skin and made her squeeze her thighs tight around his cheeks. Still, he persisted.
Accuracy. He pulled her clit skillfully against his teeth, nipping at it quickly, which elicited a short shriek and three swats to his ass before a warm, settled, "Goood boy..." His ass stung, but this was a move he knew would generate a positive response from a superior, in the end.

It wasn't long before Sandra was gushing around Alex, and he dutifully lowered his face to keep his nose pressed to her clit and lap up her juices. No waiting for a woman like Miss Evans. His tongue, so precise in the generation of this orgasm just seconds ago, flattened to a spoon to lap up every drop of the output his trainer was giving him. Lest any would get on her skirt, he would certainly be severely punished. He gripped his elbows a little tighter as he worked to extract every drop from her, and stayed with his face buried in her muff until her hand pulled him away. His mouth full, his wide eyes looked up and met her glassy ones.

"You may swallow, little boy," she said with a smirk that finally cracked her cold exterior for the first time, "and I think you've earned these." She tossed the menus on the ground in front of him, slowly stood up, and walked to the bathroom on shaky legs. Alex swallowed his trainer's cum then looked down at the menus. Careful not to release his elbows from his grip, as he had not been given permission to do that, he poured over them, closing his eyes and repeating the name of the dish and its ingredients before moving on to the next. She had only granted him an hour of study time, and he had evaporated nearly half of it in pursuit of a menu he could understand. The wine list he would just have to ignore and hope for the best.

Finally, she emerged from the bathroom and took his menus from him, pointing toward the back.

"Time to go pick up Mister Samson, little boy. Don't be late."


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