A Working Boy

I rolled over and was startled awake by the warm, athletic body sprawled next to me in my bed. He looked comfortable, fast asleep and breathing deeply. I wasn’t surprised. He’d been a busy boy last night.

Waking to find someone in my own bed quite literally never happened, not since my sort-of relationship with Johnny came to its natural conclusion. And even Johnny only stayed over once or twice.

I glanced at the clock on my bedside table. 9.24am. I’d slept later than usual... well, maybe “slept” was the wrong word. Turns out my new waiter friend had some stamina.

I was on a free week so I didn’t have any clients to worry about. That was something I did these days to make time for me and give me a break. I would work for three, rest for one. Rinse and repeat.

I got out of bed as quietly as I could, letting my hunky waiter friend sleep, the sheet only just covering his groin. My eyes were drawn to him for one last look before I left the room, his tanned skin, dark hairs on his legs and arms and a cute snail trail up to his navel. A dark mop of hair on his head and a finely chiselled face. He was a seriously cute guy. And hot. And so much younger than my usual distractions.

I padded barefoot and naked into my living room. It already looked like a bright, warm, sunny day. I went out onto my balcony and leaned over the rail, looking out at the glorious blue sky and and the yellow ball slowly rising up into it.

The summer holidays had started, the weather was warm and sunny, and I was horny and greedy for every penny I could earn. I’d had almost six months of Danny finding men to screw me for money through “Ladd Logistics”, six months where I had earned good money and become much more sexually experienced. I had become quite accustomed to getting myself to the little apartment and getting ready. I would think of it as my commute to work and it always made me incredibly horny. I told Danny I didn’t want to know anything about who was coming to see me. I found the surprise was thrilling. They were all older guys, every shape and size, and they all treated me like a little princess before sticking their dicks deep into me. They were so grateful afterwards.

And I loved every single minute of it.

Admittedly, hiding what I was doing from my parents was getting difficult. I wasn’t merely playing out like the other teenagers, I was travelling into town and often getting back quite late given my tender age. They didn’t really care. Their questions about what I was doing were cursory at best. I continually found I had nothing in common with them and I even started to wonder if I was really their child at all. They were deeply religious and conservative, my total opposites. I wanted out of there but I wasn’t quite ready. I didn’t have enough cash yet and I figured I needed another year before I could cut cut ties without being considered too young to be out there on my own.

But the summer break could be my opportunity to fuck all day long, no questions asked. I wanted Danny to find me multiple clients per day while school was out, something he wasn’t sure about. To be fair he was trying to teach me a valuable lesson. I wanted quantity because I just wanted to be fucked again and again and again, whereas he wanted fewer clients who paid more because he was in it for the money. He was also worried that I would “burn out”, something that made me snort with derision very time he said it.

Get tired of mature, experienced men treated me like a princess and screwing me in every possible way? Get real!

Danny was at his desk with Johnny, but before I could have another crack at making my demands Johnny told me about a “talent scout” he’d met. He told me he’d been introduced to a very wealthy guy who might be interested. Told me this guy was a different league for Ladd Logistics. Apparently if he liked me, he might want to take me away to spend time with him through the summer.

They asked if I was interested in an audition for for this man and of course I was. My curiosity overcame my desire to convince Danny to do what I wanted and I took instructions to meet this guy at the city’s most expensive hotel. No grubby apartment for him, apparently.

I told the concierge I’d been sent by Ladd Logistics as instructed. I was whisked into the elevator and escorted to the penthouse suite where I was thoroughly searched by a huge security guy, something I enjoyed immensely. He had me stand with my hands splayed up against the wall, my legs spread and my bottom sticking out while he ran his big, meaty hands all over me. He was firm and probing, enough to make me hard.

A hand trailed down my back, giving me goosebumps. The hunky waiter had awoken and come looking for me.

It turned out that my waiter, Ethan, was 22 years of age and until he stumbled on me and Johnny in the coffee shop toilets, he was a closeted virgin. I got his number that day, he came over than night, and two nights later he’d barely left my apartment and we’d gone at it like sex crazed teenagers.

This behaviour was highly unusual for me. I never let anyone stay over and I wasn’t really interested in relationships, just sex. And he wasn’t an older guy, so really not my type all. And a waiter for fuck’s sake! But he was magnificent between the sheets and his cock did things to me that no-one had ever done. It was sex on another level. I’d come hands-free three times now, something that blew my mind as much as it blew my balls. And for an inexperienced guy he seemed to catch on quickly that I liked the top to take charge.

I liked a guy who learned quickly.

Ethan’s fingers found my ass and he gently pushed, sliding two digits into a hole that still hadn’t recovered fully from last night. I started to stand but he held me in place with the other hand, bent over the railing, taking in the view. It was warm out here and he was gentle and I knew where this was going now that he’d started.

After several minutes of slowly sliding his fingers inside me, fucking me with them and stretching my little sphincter, rubbing the small of my back with his free hand and making satisfied noises at me, he took his hands away and crouched behind me while I bent over. He pressed his mouth between my buttocks and licked and probed my hole, flicking his tongue inside me and lapping around the rim, too. I closed my eyes and whimpered a little. He was damn good at that.

He gave a few final wide-tongued licks before standing and lining up his cock. I took a deep breath. This guy might be younger than anyone who’d ever fucked me, but he gave me a kind of thrill that I wasn’t sure I’d had before. And he’d quickly developed a taste for sex. And a talent for it, too.

“I have a taste for sex” the man said. There was no embarrassment or ego in that statement. He just wanted me to know. “And while I will fuck anything, I prefer young men. Especially when I’m very horny. And I get very horny when I’m relaxing on my Summer.”

I nodded. I didn’t have anything to say to that. Fair enough, I thought. I studied this guy. He wasn’t the oldest client I’d have let screw me, but he was probably in his seventies. He oozed wealth and power and he clearly got his own way every time. For the first time ever, I actually felt a little nervous.

“You’re a little younger than I was expecting. Don’t worry, that’s good, it’s just sweet things like you are….hard to find.”

I blushed a little.

“You understand why you’re here? The expectations I have? Was it made quite clear to you?” He asked, eyeing me like a school teacher. “Because I won’t take what isn’t given freely.”

I suddenly understood. He was worried that I was being coerced or that I was too young to understand what was going on. Well, screw that, I thought. I stood up tall, and turned slowly around for him so he could see all of me. As I faced him again, I kicked off my sneakers and then peeled my t-shirt over my head, revealing my body. He stood unmoving, his facial expression unchanging, watching.

I unbuttoned my jeans and slid them down, pulling them off my legs and kicking them to one side. I stood there for him in a tight pair of blue bikini briefs and white sports socks. His eyes were starting to sparkle and I knew he liked what he saw. I was good at reading people by now.

He took out a little device and pushed a button, and began to speak into it.

“Youthful teenage. Between five six and five eight. Slight build but not skin and bones. Pale skin, unblemished. Bright green eyes, large. Dark brown hair, unstyled. Somewhat feminine facial features. Still boyish though. Broad shoulders. Hairless back and front. Few light hairs, lower legs only.”

He paced slowly around me as I stood there. He’d covered all the bases, so without being asked I slid my briefs down to my ankles and stood again. I caught a slight smile at that. Anticipating what he wanted had pleased him.

Ethan placed me down on the little round table I had out here on the balcony, anticipating that my legs were still tired. He was stronger than he looked. He smiled, pleased with himself, as he watched himself feed his wonderful erection back into my ass. I took a deep breath as he penetrated me. That was the feeling I loved most of all in this world, the sensation of a man’s skin sliding through my opening until it was deep inside me. Surely there was nothing better.

He began to pump hard from the hips, pushing my knees back and apart. This young guy could screw, no question. Why did I find him so attractive…..? I looked up at his face. He was cute, sure, but there was no grey anywhere, just taught young skin, a little stubble now, dark hair, dark eyes, and a strong, athletic body. He took hold of my ankle in one hand and my dick in the other and my eyes rolled back in my head. How did he know to do that……? To take hold of my dick at just the right time….?

He took hold of my dick, which was standing to attention like a good little soldier. “Penis size is acceptable, small to average. Nice small scrotum. Pubic hair is perfect. Small buttocks, also boyish.”

I was starting to breath more heavily, this unusual examination without touching creating waves of sensation through my body. I felt entirely submissive here with this powerful figure. My pulse had started to race. I realised he had paused. His last comment had been about my buttocks. I had a flash of inspiration and I bent over, grabbing my ankles. It felt so damn hot to be showing off my hole to this guy in this way. I hoped he would fuck me after all this.

The was a further pause before a hand reached out to cup my bottom. His fingers trailed lightly along my crack, brushing past my hole in a way that brought me out in goosebumps. He pressed a thumb to the centre of my anus and pulled it to one side, spreading me slightly. Who knew being examined could be so fucking sexy?

“Very pretty bottom. Very pleasing to look at” he said, and his voice had changed. It was quieter, like he was lost in the moment. “Overall a fine specimen. A delightful boy.” And then a click as he switched off the recorder.

“Kneel on the armchair there, and push that out for me” he said giving me a light slap on the bottom. I scrambled to comply. He took the two or three paces to the chair and touched me again.

“You are ready at this moment?” He asked. I nodded, looked back over my shoulder and whispered “yes”. Time seemed to slow. Something about this was different, somehow. This wasn’t a quick bunk-up in a filthy apartment, or a crafty fuck in the woods or someone’s office. The surroundings here were plush and rich and my guy was an experienced man who took his time, and he took what he wanted. This guy had staff outside the room waiting for his call and they must all have known what I was there for. There was something in this scenario that heightened every sensation for me. Maybe Danny had been right, maybe less was more after all.

He spent long and sensuous minutes fingering lubrication into me, penetrating me with his thumbs, then using fingers on both hands to pull my anus open. He stretched me, caressed me, touched me everywhere while I melted on the armchair. Then he slowly pushed his dick into me. He screwed me delicately, like I might break. His strokes were long, deep, but gentle. He took his time, exploring everything about me and deciding whether I should be his holiday companion. It took my breath away in all new ways. He reached over and inserted two fingers into my mouth and with the other hand he reached underneath me to play with my dick and balls.

There was somethings sensational about being touched and having fingers explore my mouth while a good sized penis slid in and out of me. I was in ecstasy. In that moment I felt like I was his, bought and paid for, his willing property. I sucked his fingers and pushed back on every stroke.

We came together, synchronised, sweating and out of breath despite the slow and sensuous screw.

I panted, my own cum spattered across my torso and Ethan’s dripping from my scrotum and gaping hole. He’d pulled out and shot over me, something I told him I thought was hot. Like I said, he was a quick study.

He grinned at me, bent over and kissed my cheek, my neck, and then my mouth. I opened wide for him and our tongues did a little electric dance. He was still grinning when he pulled away and I couldn’t help but grin back at him.

“I like morning sex” he said.

“You seem to like morning sex, evening sex, middle of the night sex, and middle of the day sex” I laughed. Not that I was complaining.

“I’m making up for lost time” he said, that sloppy grin fixed in place as he drank in my post-coitus state. He loved to look at me, and I admit I loved being the focus of his attention. His dark eyes sweeping over my body lit a fire in me.

“You’re making up for lost time very quickly!” I said. And then I felt the need to be honest with him before this went any further. It would either end our fun or we’d get past it. I don’t know why, but for the first time I really hoped we’d get past it. He frowned at me, seeing the change in my expression. “Listen” I said. “You might not be so into me after you hear what I do for a living….”

“Why do you do this? Is it a good living?” He asked as we lounged in the hot tub. After our sex, he had brought me here. We had walked naked past some of his staff who simply ignored us and he didn’t seem bothered either. He had lathered me, washed me everywhere, and now we were facing each other over a mountain of bubbles.

I shrugged. “It’s good money that might get me my own place some day. And I like it. I like it a lot.” I said. I wasn’t embarrassed about that. I liked it.

He nodded. “You’re good at it, too. Very good. Tell me, what is in the way of you coming away with me for….let’s say two week.” He asked. He wasn’t stupid. He knew I was on the young side and that two weeks away might cause some problems for me.

“I don’t know.” I answered truthfully. “I need to find a way to do it…. My parents…..” I said, breaking off, not sure where to go with that. I was comfortable telling anyone that I liked to ride around on cock. I was less comfortable taking about my stupidly conservative parents.

He looked thoughtful for a minute. “If I arrange a letter from a European school…..? A student exchange, something like that. It will appear official and will stand up to scrutiny if my people do that.” He was so damn sure of himself. It thrilled me. He wanted me, and he’d have “his people” do whatever to make it happen.

I nodded. “Yes, that would work. They won’t check up if it looks official. They don’t really care what I do.”

He smiled warmly at me and his eyes twinkled. “My people will be in touch through your handler.” He said. I balked at that, just a little. He seemed to notice. “What’s wrong?” He asked.

“Nothing” I said quickly. “It’s just…. Danny…. He’s not my ‘handler’. He just finds people for me, you know?” I don’t know why that irritated me so much.

The man chuckled deep in his chest and looked thoughtful again. “Maybe I can intervene there. If you and I are going to get better acquainted, and we are, I assure you….it would be better if the quality of your….clients was more in my range than in your….business partner’s?”

He had chosen his words extremely carefully and I blushed, grateful and suddenly realising that maybe Danny was my handler after all. I nodded. I didn’t quite know what this man meant, but if he had friends like him, I was in!

“I’m Stefano Valentini” he said. “We will travel in four days. One of my people will be with you at all times so that you’re never alone, for your comfort and your security. We are going to spend two weeks on my yacht off the coast of Monte Carlo. You will need nothing. I will have everything you need. Is that acceptable?”

“Er…yes…. Mister….” He interrupted me.

“Call me Stefano.” He said with a smile.

“Yes, Stefano” I said. “I would like that.”

“Get dressed. My driver will return you. I will make some arrangements to improve your class of customer and I will see you soon.”

“So you’re a high class prostitute?” He asked, frowning, taking it in.

I wasn’t sure that had gone down very well. Ethan’s face had dropped and he looked like I had slapped him.

“Does that mean… I have to pay you…..?” He asked, appearing genuinely confused. I sat up, got off the table, placing my hands on his hips and drawing him closer. I looked up into his dark eyes. He seemed on the verge of tears.

“No, silly!” I said softly. “I called you and got with you because I like you and I wanted to spend time with you. Which is weird because…..” I stopped myself. “Anyway, what matters is that I have enjoyed the past couple of days and you have been a wonderful, attentive lover. I wanted to be honest about what I do. That’s all.”

“But you didn’t want to honest before…..” He said. “Just after?” He seemed to be growing angry and frustrated, but I could see he regretted saying that. Still, I figured this wouldn’t end well. I understood. Not many people wanted to get with a whore. It was the one down side of a brilliant life. Relationship’s were elusive. It could be lonely at times. I’ll admit that.

I looked away, out over the balcony at the sunny, crystal-clear sky. For some unfathomable reason this one was hurting more than usual. I was annoyed with myself, feeling attached to a kid after only a few fucks. I wondered whether I was getting sick or something.

Ethan took hold of my chin between his thumb and forefinger and turned my head, lifting it so that our eyes met.

“Okay” he said, and his mouth started to form a grin again. His eyes lost their sheen and began to sparkle. “I’m over it. I guess it doesn’t really bother me.”

I frowned. “Eh” I said, an automatic reaction. “That was….quick….?”

“Yeah” he said, and shrugged. “I started to get pissed, then I weighed it up, then I decided I don’t mind really. I’ve enjoyed the last couple of days too, you know. And I like you. You’re so my type and I didn’t even know I had a type before now. You make me wanna fuck all the time!”

I burst out laughing. “You HAVE fucked all the time!” I said, tears of laughter running down my face. “But I’m happy that you’re not mad at me. It’s very…. I dunno, mature of you?” I said, not sure if the was the right word but suddenly seeing something. This guy might be young, but he had an old soul.

He smiled and wiped my tears away. “Now tell me what’s weird” he said.

I raised an eyebrow. Good memory, I thought. I couldn’t back out now. “Look….” I said. “All my clients are older guys. I like older men” I shrugged. “Rich, mature guys with very big bank balances and a desire to look after me. That’s my type, old rich daddy types. You are the youngest guy I ever screwed!”

“So it’s weird you like me, because I’m not some wealthy daddy-type?” He said, and again I was impressed with his maturity and insight.

I nodded. “Yeah” I said.

He grinned. “But you do like me…..?” He said, and he winked as he squeezed my bottom.

I grinned back. “Shit… yes, I do.” I admitted.

“Well that’s good” he said. “Because I like you too. And I’m half of what you go for, if that’s any consolation.”

I raised an eyebrow. I didn’t understand.

“I’m rich” he said, and he pulled me in for a deep kiss.

“He’s rich” Danny said. “Like, billionaire rich. I did some digging. He comes from old money, originally French. He’s into shipping and all sorts of stuff.”

I was impressed, but I was still more impressed with the sex than the money. I shrugged. Stefano had been true to his word and arranged everything, even placing a call to my parents to reassure them I would be well taken care of by the people at “the college”.

“Did you know he was going to do this…?” Danny asked, frowning at me.

As well as organising my trip, Stefano’s people had insisted to Danny that I drop all of his clients with immediate effect. A man had come to see Danny to tell him that “the boy is to remain free of clients until he returns from Europe”, after which time “Mister Valentini will ensure he has a venue to work from that befits his station”.

“So, no sex…?” I asked, pouting.

“No, no sex.” He said. He slumped down in his chair. “Now I have to try and convince a full list of regulars to go with one of the others. And none of them will like that because they all want a piece of your ass.”

I felt sorry for Danny and I offered to help compensate him. He’d been good to me so far, and I didn’t want our arrangement to stop.

Danny shook his head and chuckled. “Kid, don’t you worry. I’m not worried about the money. Your new guy has compensated me in a big way….a big way!” He said, his eyes actually going wide as he thought about that. “And he says his talent scout will be pushing new clients your way and suggested some new pricing for you. If he comes through, we’re gonna be fucking rich.”

“So what’s the problem?” I asked, confused.

Danny looked at me and he seemed confused too.  “I don’t know, kid.” He said.  “I guess I’m just sour that I didn’t think of it myself.”

To be continued.

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