The Naked Assistant (Patreon)

All characters are 18+

Part 1 of 2

I could have gone straight to college after high school ended, but there was something about going from one mind melting form of education directly into another, that just didn't sit right with me.

I'd always been a fan of travelling. My dad was something of an adventurer when we were kids, and he took us to some truly fascinating places around the world, so when the offer to take a year out to travel came up, I jumped at it.

Unfortunately, my family wasn't one of these disgustingly wealthy families, so there were no hidden funds to help me along the way. That meant that if I wanted to do this, I'd have to make it work myself.

I was eighteen at the time, with barely a couple hundred dollars in my account, but my parents offered to pay for my flight to any country in the world as my Christmas present, so I picked Italy.

I wanted to start off somewhere pretty standard so that seemed like a safe bet, and from there, I could plan out the rest of my journey. The only problem was that in order to do that, I needed cash, so before I even got on the plane, I'd spent considerable time looking for work, and although it seemed too good to be true, I found it.

The ad was simple enough. Some rich family required someone to work in their home as something of a personal assistant to their son who apparently ran a business. The money was good, the hours were good, and both accommodation and meals were included. It was a summer job, so three months of this and I'd be set for the entire year, and after two phone calls with the father, everything was sorted.

I'd been to Italy once before as a child, and recalled the beauty of the place. We'd gone to Rome, but when I landed and took a pretty long bus journey through mountains, around lakes and across orchards, I realised that I was in a very different area now.

It was stunning, but certainly secluded, and when I finally reached my new home for the next three months, I audibly gasped.

The huge house was set on acres and acres of land. There were water fountains in the front yard, a large driveway filled with lavish cars, and large Roman pillars holding the breathtaking building up. I was excited when I knocked on the door, but that excitement turned to shock just a moment later.

Angelo, who I had spoken to on the phone, was a fifty-something year old man, and seemingly the reason for the wealth. He was a businessman of some description, and he and his son lived in this gigantic mansion alone. None of that is what shocked me. What shocked me was that when Angelo arrived at the front door to greet me, he did so completely naked and I couldn't help but gawp at his impressive cock.

"I hope you don't mind" the dark skinned man smiled, "we are practicing nudists".

I wasn't sure if I minded or not, but what difference did it make? I'd flown hours and bussed almost as long to get here, so I couldn't exactly turn back now.

I awkwardly shook his hand and faked my best smile as I followed the naked man into the shade of his beautiful house and followed him around for the tour.

"It's just Matteo and I" he told me as he showed me their fucking library. "Though it sometimes feels like I live here alone" he added with a laugh, "he spends so much time working in the office that I hardly get to see him anymore".

Angelo turned to me, and once again, my eyes fell to his large, tanned cock.

"That's why you're here" he smiled, "let me introduce you".

Climbing up the large staircase behind the naked man was an interesting ordeal, but I kept my eyes on the expensive wood until we reached another room. He knocked twice and entered, beckoning me after him.

I don't know why I hadn't expected it. 'We are practicing nudists' should have given it away, but when I stepped into the room and found a very attractive young man of similar age to me, sitting with his legs spread on a chair, and a delicious looking cock and balls resting between them, I almost choked on my own saliva.

"This is Matteo" Angelo told me with a warm grin, "Matteo, this is Andrew".

The naked teenager most certainly looked after himself. He had jet black hair, cut short, his features were striking, with a sharp jawline and a physique to match. Even as he relaxed in the office chair, his abs were visible beneath his bronzed skin. I gulped as he regarded me with his hazel eyes.

"NO!" He snapped, and I jumped slightly, "that is not good enough!"

Angelo turned to me and smiled apologetically. He seemed to smile quite a lot.

It took me a moment to realise that Matteo wasn't actually talking to me, but into an earpiece. When his phone call ended, the young entrepreneur stood up, his cock swinging between his legs, and walked over to me. I did my best to keep my eyes on his.

"You're my new slave, huh?" He asked with a devious smirk, until his father stepped in.

"Personal assistant, Matteo" he said, rather cooly, "please show this one a bit of respect".

"Of course, father" the young man replied, but his expression didn't change, and I began to wonder if this had all been a mistake.

"I'll leave you two boys to it, then" Angelo nodded, and squeezed my shoulder as he left the room.

"You're American, huh?" He asked, seemingly completely unbothered that he was stark naked. I nodded.

"Good" he said, turning and strolling slowly back to his chair, "you can leave your clothes in that cabinet" he continued, pointing to an old looking closet.

My heart began to race slightly as I watched his plump backside tense with each step.

"Uh... Excuse me?"

He looked back at me and shrugged.

"I'm sure my father explained that this is a nudist household" he scoffed, "haven't you noticed?"

He turned his body toward me and pointed directly at his long pole.

"I um... I didn't know until I got here" I gulped.

"And now you know" he replied smugly, "you can undress now".

The teen sat back in his chair and rested his chin on his fist as he stared at me. There was something painfully humiliating about this encounter, but there was also something extremely hot about it, too.

I'd known I was gay for years, I wasn't too bothered by it, either, but having to look at a very attractive, naked young man whilst being unable to hide my interest, wasn't a very exciting premise.

I considered it for a moment as he watched me. What choice did I have, really? I was thousands of miles from home, with only a few dollars to my name and no way of getting anywhere without money. Money which I could only get from this job.

I took a deep breath, and as confidently as I could, began to unbutton my shirt. All I had to do was keep my mind focused on Bertha, our ninety-seven year old neighbour back home. If I could do that, boners weren't going to be a problem.

As I undressed, Matteo watched me eagerly. I wasn't in bad shape by any means, but I certainly wasn't as ripped as him. I pulled my shirt off, folded it and placed it inside the weird cabinet. I kicked my shoes off next, followed by my socks as my cheeks became redder and redder, until finally I slid my shorts down, and stood back up.

"I don't know why people always do this" he scoffed, "do you not know what naked is?"

I don't think anybody had seen me naked since I was a baby. It simply wasn't a normal part of life back home, but I wasn't at home anymore, so with one more deep breath, I hooked my fingers into the waistband of my boxer briefs, and stood naked before my new boss.

"Good" he nodded after a moment of studying my nudity.

Once again, I was less impressive than Matteo and even his father. Hard, my cock reached six inches, but soft, I had nothing to boast about.

"Get me a coffee" he said, and waved in the direction of a coffee machine behind him, "get one for yourself, too, if you want", he added, hammering away on his computer, "but mind you don't burn your little cock", his attention was no longer on me, so he didn't notice me wince.

As I began to follow my orders, I couldn't help but feel degraded. What would my parents think if they knew that I'd been stripped naked and forced to work for a man my own age? Though I guess there was nothing forced about it. I had made the decision to do this, and I'd continue to do it until I made enough money to go elsewhere.

Being naked around Matteo quickly became quite normal. I suppose it helped that he was also naked, but what helped the most was Bertha. The more I looked at him, the more I realised just how fucking hot he was. Sure, he was an asshole, but he was the most attractive asshole I'd ever laid eyes on.

Angelo returned a few hours later to find his son having a Zoom call with one of his friends, and me sweeping up popcorn completely naked as the two of them spoke rapidly in Italian. I knew his friend could see me, Matteo had angled to camera to make it so.

"Speak in English please, Matty" Angelo said sternly, and his son scowled but obeyed.

It felt very strange being naked in front of Angelo, yet the man didn't bat an eyelid. He simply smiled at me once more.

"I'm going for dinner with a friend" he told us, "Andrew, perhaps it's time you got some rest. You're not even supposed to start until tomorrow. Your room is right across the hall".

I glanced at Matteo who sniggered with his friend, and then nodded as I did my best to keep my junk hidden behind the pole of the sweeping brush. The man smiled again and left.

"Hey slave" Matteo smirked, "my friend wants to know why your dick is so small".

I clenched my jaw, but ignored him. There was certainly no way I'd manage three months here, but I'd get my first payment after a week, and that would be enough for a ticket out. I just had to endure the little shit until then.

As I left the room I sighed to myself. A luxurious house with two handsome, naked men and a swimming pool under the sun in Italy should have been a dream, but it was slowly turning into a nightmare.

I found my room where Angelo had left my suitcase, but I was too exhausted to do any unpacking now. The journey had been long, and the couple of hours that I'd spent slaving away for Matteo had felt even longer. I needed to sleep, and that's exactly what I did.

"You're late",

The words seemed to wake me from a coma. My eyes flickered open and stung in the light, and it took me a moment to even realise where I was. I glanced around, groggy and half asleep, until I found Matteo standing at the end of the bed.

"It's nine in the morning" he told me, "you were supposed to start at seven".

I wiped dried drool off my chin and rubbed my eyes.

"Father said to let you sleep in, but if we all slept in, nothing would get done around here, so let's go".

I nodded, though I had barely even heard what he'd said. As I sat up in the bed, my nudity shocked me once more. I'd forgotten to dress, but I guess I was better off getting used to that. What I wasn't used to, however, was the fact that Matteo continued to stare at me, and my morning wood lay exposed against my groin.

"No need to cover it" he smirked, "father's gone golfing, so it's just us two this morning".

I gulped, and now the idea of being alone with the handsome asshole was doing nothing to stem the flow of blood to my cock.

"Before we get started" he continued, his eyes still on my erection, "I should let you know that I have some... Requirements that I need taken care of if you want this to work out for you".

I looked up at him as I tried to put as much distance between his eyes and my hard cock as possible.

"What requirements?" I asked, "your dad said–"

"My dad isn't your boss" he interrupted, "I am, and if you want to be paid, you'll do what I say".

I felt a flash of anger run through me, but in my head I repeated the fact that I only needed to do this for a week.

"I like to cum three times a day" he said nonchalantly, "I don't like jerking off and I don't like cleaning up, so it's up to you to make that work".

I gawped at him, and now my morning wood had turned to morning concrete.

"Isabella liked to suck in the mornings, take it in her ass after lunch, and her pussy at night, but you have one less hole, so I'll let you decide what to do".

I couldn't believe my ears, but I didn't need to. Matteo walked around the edge of the bed and stood inches away from me.

"How about you start with your mouth" he told me, taking his long cock into his fist, "you talk too much anyway".

I felt his hand around the back of my head, and I didn't resist when the handsome young Italian pulled me toward him and pushed his flaccid pole against my lips.

"Kiss it" he told me, "you two are about to become very close"