Help Wanted

By Happy Endings
published September 26, 2019
Summary

A young man down on his luck decides to answer a job advertisement for a houseboy position.

Help Wanted: Houseboy

Must be:

-Male

-Aged 21-30

-No major commitments

-Reasonably fit, able to do basic household chores

-Willing to learn and adapt to job expectations

-Willing to do sexual favors as part of your job

Benefits:

-$20/hr wage

-Health/Dental insurance

-401(k) matching

-Paid time off, including paid holidays

…Well shit, how could he pass that up?

Jason carried the crumpled advertisement in his hand as he got out of his car at the entry gates of the driveway. He looked past the iron railings and let out a low whistle at the rather nice house beyond. Not quite a mansion, but definitely several bedrooms, plenty of bathrooms, and whatever other kinds of rooms rich folk like to stuff their houses with. He made an effort to smooth his wrinkled rental shirt a bit as he pressed the button on the gate’s intercom.

Before long, a voice came out of the box. Despite the crackling of the sound quality, the voice had a soothing, and almost youthful tone, “May I help you?”

“Uh, yeah, I’m here about the ad? For the houseboy position?” In the back of his mind he couldn’t believe he was about to offer himself to be some old geezer’s trophy boy. Oh well, it would just be until the old man passed away, and by then he’ll have plenty of money from the job. Hell, if he pretended to give enough of a shit, maybe the guy would leave him something extra?

“Oh! Yes yes, come on in! Door’s unlocked, just wait in the hall and I’ll be right down.”

Well…that was easy enough. Jason made his way down the long driveway, passing groves of apple trees just starting to bear fruit. As he gazed around the massive lawn and gardens, he couldn’t help but feel a little discouraged that he would probably have to take care of these. Oh well, what else did he have to do? He was broke, months behind on rent, his deadbeat parents are probably too high to remember who he is, and getting into college was definitely out of the question with his negative bank account.

He carefully opened the large wooden door and made his way inside. Despite the regal outward appearance, the inside was rather modern and comfortable. He figured it would be like some stuffy grandpa’s home, but instead it seemed oddly welcoming. Hell, there was even an alarm speaker that said to the empty hall, “Front door.” There were very few doors; he could see into what looked to be a dining room with adjoining kitchen, stairs leading up to an open hall with signs of bedrooms, a sitting room with a TV and…was that a Wii? If he didn’t know any better, he’d say the man living here was–

“Sorry for the wait!”

Jason’s head whirled around to the staircase, where descending the steps was a man looking no older than 29. He was dressed in a nice dress shirt, open at top of the chest, tucked into some khaki chinos. His hair was wavy and brown, and his green eyes shined with a youthful vigor that matched his expression. He was barefoot, and Jason immediately realized why there was a shoe rack next to the door, neatly organized, and that the wooden entryway eventually gave way to lush white carpet. He blushed and looked around, but stopped when the man waved his hand.

“Oh don’t worry about it, I’ve seen plenty of applicants by now, I’ll need to get a carpet cleaner out here either way. Come in, make yourself comfortable! Can I get you some coffee? Water? A coke?”

Jason opened his mouth to respond that a coke would be nice, but there was just something about the gaze the man was giving him. He quickly realized that this was a test. The words ‘reasonably fit’ lingered in his mind.

“Um…water would be great, thanks.”

The man grinned and nodded, “Great choice! Water it is. Oh, and you can call me Nathan for now. Nathan Giles.” He extended his hand, which Jason took with a slight grip. What did Nathan mean by ‘for now?’

As Nathan went to fetch the water, Jason stepped into the living room. The world seemed to be spinning around him. He had a feeling Nathan was older than he appeared, but what happened to serving some nearly-dead old man with a huge inheritance? Shit, it really was too good to be true.

Still, Jason had to admit the guy had good taste. No stuffy portraits or delicate antiques. No, this house was definitely modern. A big TV, a sizeable game collection, displays and murals of city skylines and famous movie posters. Nathan was somehow able to combine the grandeur of wealth but with a Millennial flair. Maybe this wouldn’t be so bad after all? And Jason had to admit…Nathan was pretty cute. Jason wouldn’t say he was gay, definitely bisexual for sure, but he always imagined himself ending up with a woman.

His inner monologue was interrupted when Nathan returned with two glasses of water. He took a seat diagnoal to where Jason sat and set the water on coasters on the table in front of them. It was definitely a more relaxed atmosphere than the usual interrogation-like interviews normal jobs had.

“So, let’s go over the basic requirements before we get into the questions I have for you,” Nathan started with a smile. “Answer honestly to everything please, don’t get nervous if you don’t fit something 100% or don’t know the answer to a question.”

Jason nodded and took a sip of the water.

“Name?”

“Jason, Jason Hardesty.”

“Age?”

“22, turn 23 in a couple months.”

And so the questions continued, Jason basically having to prove that he fit the criteria. He didn’t have the money for a gym membership, but the odd jobs he would do here and there required some physical labor, so he was in decent enough shape. He didn’t go into detail on his personal life but did mention he was single, not in college, and lived several states away from his relatives.

“And, of course, you understand the ah…implications, let’s say, of being a gay man’s houseboy?” Nathan winked.

Jason nodded, “Yep, sure am.”

Jason caught Nathan’s expression falter a bit, oddly enough. Was it something he said? Wasn’t that what Nathan wanted to hear? “Stand up for me, please.” Nathan gave an upwards motion for Jason to stand, which he obliged.

“Hmmm,” Nathan remained seated, bending this way and that with a perceptive gaze. Jason figured he was checking out his body and sucked in his stomach a bit. He tensed his muscles for good measure. Every little bit helped, right?

“While my houseboy you’ll have to conform to certain rules, including speech and manner of dress. I can tell by your outfit that you don’t have anything nicer than…well, that?”

Jason winced at the jab. No, of course he didn’t! Did this guy seriously expect someone like him to be able to afford a suit?

“Guess not. No worries. But it does put you in a disadvantageous position, Jason. I’d have to provide you with clothing, correct your posture, wait for you to tone up, change your speech…that requires a significant amount of effort, y’know. Why should I hire you?” The stare Nathan gave him was piercing and calculating. Jason felt his stomach lurch at the sight of it. Despite being so young, this man somehow managed to command an almost militaristic amount of respect. Despite being probably the same height, and with Nathan sitting down, Jason felt unbelievably small.

Jason sighed, looking downward. “I don’t know. I just know I don’t have any other options.” Oh well, maybe that construction company was still hiring?

Nathan didn’t say anything for a moment, hardly even moved. Then, a smile crept on his lips, “Why don’t we try this…you have a trial period of one month to prove yourself. You’ll sleep here in the bedroom I have prepared and start the job first thing in the morning. You’ll have the advertised pay and benefits, but if I don’t see commitment to the job in one month’s time, you’re out. And I’ll have free reign to do whatever it took to get you to where I need you to be. Agreed?”

Jason lit up, “Wait, seriously? Holy shit, that’d be great, thank you!”

Nathan stood up and extended his hand to shake once again, “I hope you do a good job, I’d be most pleased if you managed to make the improvements I require. Take the rest of the day to prepare your belongings. Donate your old clothes, wear what you’re wearing back here. You won’t be needing them anymore.”

~~

Jason had what was probably the best sleep in his life. The spare bedroom was air conditioned, cozy, and the bed was plush and comfortable. He could definitely get used to this! He woke up to the alarm blaring at him on the bedside table, and he rubbed his eyes. Nathan told him he would be entering Jason’s room to get the ball rolling, and right on cue the bedroom door opened and Nathan strolled inside.

“Hope you slept well! Get up, let’s get you sorted out.”

Jason got out of the bed and stood next to Nathan, who promptly flipped a switch. Immediately a TV hanging on the wall turned on and revealed a spiral. Jason’s eyes were drawn, and confusion spread across his face. What was this about? Nathan didn’t mention anything like this. Oh geez, was this guy into freaky shit? He really shouldn’t have accepted the offer without asking what kind of things Nathan was into.

After what felt like a minute, the screen turned off. Immediately he felt a stiffness…everywhere. He looked over at a nearby mirror by the closet and gasped.

Nathan did the explaining for his disbelieving eyes, “Good, you’re awake again. Let me explain what you’re looking at, in case you’re still groggy. First, I caged your cock. The sexual tension will make sure you stick to the agreement, otherwise it’s not getting released for a veeeery long time. Next, the shirt. Standard dress shirt, but modified a bit. Around the cuffs are zip ties, to make sure those sleeves stay nice and smooth. It’s also been tucked into reinforced briefs to make sure it stays tucked into those nice pants I got you. And don’t even think about trying to take those off, that belt is locked in with the padlock you see by your crotch. Don’t worry, you’ll still be given bathroom breaks, though don’t forget to take the plug out when you go. The tightness you feel around your calves is the garters keeping your socks up, and those dress shoes are tied with the strongest knot there is. Not locked, of course, but I doubt you’ll be able to do much bending, given the back brace. I mean, let’s be honest, you didn’t honestly think I’d let you be a houseboy with such poor posture did you? The collar, you’ll notice, is tight but not so tight that you cannot breathe. If you get claustrophobic, I will of course adjust it, but the tie is also zip-tied and will remain tight against your throat. As for your hair, I did away with that gross man-bun. Short and neat is how you’ll style it from now on; complete with comb lines. Finished off with a freshly-tailored blazer, fitted just right, and locked on the inside to make sure everything stays together. And lastly…well, you should be feeling the effects right about now. Don’t worry, it’s not poisonous or deadly, but it’ll help make sure that rather crude mouth of yours at least appears polite.”

I could feel my heart rate racing even faster as my lips started to curl seemingly on their own until my mouth was fixed into a big, placid grin. I looked over at Nathan’s smile, once charming, now slightly more mischievous. “Remember, boy, you agreed to this.”

To be continued

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