A Working Boy

My phone buzzed, pulling me out of my dream.  I glanced at it through squinting eyes.  It was a flight alert telling me that today’s client would be landing on time.

I sat up in bed. It had been a crappy night and it felt like sleep had only just found me. I wasn’t usually troubled by much in life, but I was struggling with how I felt about everything since a cute young coffee waiter had walked into my life a month ago.

I had spent a long time last time thinking about Ethan and I’d come to the inescapable conclusion that I really liked him. Like, really liked him in a serious way. I didn’t understand it, because I had never felt this way about anyone or anything.

Guys in my life were older than me, wealthier than me, and they wanted to use me for sex. I’d built a very comfortable, very happy life that was based on me taking advantage of those facts. And up until now I enjoyed it without equivocation.

Since my first time in the woods, I loved being used for sex. I enjoyed being fucked more than anything and I loved the financial rewards too. I often used to wonder who was using who.

Suddenly I felt guilty that I was seeing clients. Last night I found myself thinking about my retirement plan that before now only Max thought about. Then I wondered what I’d do if Ethan decided I wasn’t good enough for him and that had almost given me a panic attack.

How could one boy turn me into such a walking disaster zone? Even thinking about him as I sat up in bed made me grin like an idiot when all I wanted to do was scowl. I wanted to feel grumpy that he’d turned me upside down, but instead I was getting all dreamy over him.

I told myself I’d worry about it later. I rolled out of bed and went to get showered. Lord Jonty was flying in from the UK especially to see me and I needed to get ready. I liked Lord Jonty. He was one of my first regulars after Stefano changed my life back on that yacht.

Stefano took a long drag on his fat cigar and blew a large smoke ring. He peeked at his cards before returning them, face down. His face was expressionless.

The card game had been a lot of fun so far. The players were keen to lose and yet their competitive nature meant they hated not winning. It was cause for a lot of joking, teasing, and swearing.

I adored being the centre of everyone’s attention. So far I had been bent over the arm of the couch by the first man to lose all his clothes. He had gently slipped his cock inside me then humped me while he squeezed my hips. Then I rode up and down on the second where he sat, his hot kisses on my neck and his bulbous head buried deep inside me.

I couldn’t be bothered to get dressed again, so these guys all had full sight of what they’d win if they lost!

Stefano seemed to approve of my nudity, so I sat on his knee in between servicing his friends, watching the game studiously. His hand never left my bottom, either cupping or caressing my buttocks or idly fingering me while he considered his friends facial expressions. It felt so good. Slutty and submissive and utterly, wonderfully brilliant.

In no time the third guy had to strip off his boxers, much to the amusement of the others. They agreed to break for ten minutes so that glasses could be refreshed. The loser, a guy they called Lord Jonti, took me by the hand and led my out on deck. He turned me around to face him and he kissed me deeply, his tongue fully in my mouth while his hands snaked down my back to grasp my buttocks.

“What do you prefer?” He asked in a well-spoken British accent.

I smiled. “You can do whatever you like!” I said with a little giggle. It was going to be a quick screw whatever. I was keen to see what this British guy had to offer.

He studied me thoughtfully, weighing up his options, his tongue wedged in his cheek as he looked me up and down. He led me to the back of the boat, to the little platform that was almost level with the water. The sea breeze was cooler here and it brought me out in goosebumps before we had even started.

“Hands and knees, I think” he said and I complied immediately, sinking down and sticking my bottom out for him. His would be my fourth dick today, my new record.

To my surprise he got behind me and ate me out, thrusting his tongue inside me. It made me say “ooohh” a lot. He moved quickly, urgently, with firm hands grasping my bottom as he tongued at my hole and licked around my ring. He couldn’t care less that his friends had already been in me this evening. It didn’t bother him or stop him from doing what he wanted.

By the time he pulled away my forehead was resting on the floor and my ass was pushed out as far as I could get it, my body in full submission to the sensations that flooded my little body. Then he crouched behind me and I felt him slide into me from head to hilt in one single movement. I took a deep breath, letting the feeling of being so full wash over me.

I moaned with pleasure. His cock wasn’t the biggest, but it felt just right, like it was a great fit. He fucked it into me, going slowly at first and building up speed as he went until he was like some crazed dog humping me from behind.

I found the position and surroundings were a huge turn-on. It was liked we’d snuck away from a party for a naughty outdoors fuck. I could hear the water lapping around the yacht and distant music from some club on the shore.

Best of all, I was totally naked out here and anyone could wander by at any time. That was especially thrilling.

He didn’t last very long, but I guess it was only meant to be a quick screw. He grunted, pulled his cock out and before I could turn and suck him, I felt searing hot droplets pepper my back. He came a lot, and it was hot spunk.

I sighed. Another one down. There were technically another three to go, if Stefano wanted to do me again. That made me excited.

The guy dipped his handkerchief in the sea and wiped his cum off my back. The water felt cold at this time of night and I shivered. He pulled me up onto my feet and pulled me in for a warming hug.

“Quite delicious” he said as he held me close. “I have friends near you, I think. I will make sure they hear about you. They would pay well to spend time with a beautiful boy like you. If you.....?”

I cut him off. “I would like that, thank you” I said politely. I smiled and thanked him with a long, slow wet kiss.

We hurried back to the lounge where we found the others drinking and smoking cigars. The two last men were totally naked and I raised an eyebrow.

“We’ve decided to quit the game” Stefano said to me with a grin. “My friends here can wait no longer. Are you up for.....”

Of the six guys who played strip poker on Stefano’s yacht, only one was still an active client. Stefano passed away about eighteen months after we met, his wonderful big heart giving up on him. Two of the others followed him soon after, and another had a stroke and was being cared for by his family. The fifth didn’t like to travel any more and had ben plagued by poor health. That left Lord Jonty, the English aristocrat. He still liked to jump on a plane and travel to me and he was still able to show me a good time.

Lord Jonty was the only client I didn’t see at my apartment. I always met him at his hotel. I figured if he could fly all the way here, I could get an Uber across town.

His Valet met me in the hotel’s reception and showed me up to the most expensive suite in the place. He let me in, then made himself scarce. He was a handsome guy and I enjoyed flirting with him, seeing if I could get him to flirt a little in return. He was always so professional, but I was sure he was interested. It was all in the eyes.

Jonty was laying on the bed, propped up on a heap of pillows, his bathrobe draped loosely over him. He looked more frail than I’d seen him before. I knew he’d been unwell, but whatever it was must have really taken it out of him. It made me a little sad knowing that these men, the guys who’d made me, were gradually dropping out of my life.

I pulled myself together and went to him, a big smile on my face. I kissed him, a long, hot, wet kiss. Jonty was a great kisser, the kind of guy who really knew what to do with his tongue.

“Kid, it’s great to see you. You always make me feel twenty years younger!”

I giggled. He liked it when I giggled.

We usually chatted for a while before we got down to it, but today I wanted him, to show him I cared and I was still interested. I quickly stripped off everything except the tight white bikini briefs I had selected especially for him, almost girl’s panties but not quite. He raised an eyebrow and watched intently. As I climbed onto the bed and straddled him, kissed him some more, he ran warm hands over my back. I loved his touch.

He let his hands drop to my bottom, sliding my underwear down as he went. He reached out with long fingers and touched my hole, sending a shiver of excitement through my slim body.

“I’ve missed this.” He said.

I shuffled to the side and peeled off the underwear and immediately got to work making his Little Lord hard. He had a nice dick, a good size and shape. I always thought of it as the Goldilocks dick, not too big, not too small. Everything just right. Not many people had a Goldilocks!

As soon as he was hard, I dribbled some saliva into my hands to lube my ring and I positioned myself over him. I sat back, impaling myself. I watched his eyes close briefly as he felt that sensation of my tight passage gripping him. I sat all the way back, letting him fill me to the brim, and then I bounced up and down.

Lord Jonty could go a long while in this position and I wanted to feel fucked by him. He touched my legs with his hands as we screwed, alternating between soft caresses up to my thighs and then gripping parts of me firmly and squeezing.

After long minutes of enjoying his very hard member sliding in and out of my boy pussy he looked me in the eye. “You know what I want” he said.

I nodded, feeling submissive. I slid myself off him, turned away from him, and got on my hands and knees. This is what he really loved, and he wouldn’t last long in this position.

He got up on the bed and crouched behind me. He lined up his cock and fed it into my hole, slowly pushing it into me, slowly moving it up into my rectum. I sighed. It felt so damn good.

He grabbed my hips and started to pump into me, really going for it. I put my head down and arched my back. He was really slamming into me and went for far longer than usual. I got the sense he was about to pull out and come up my back as he usually did, but this time I wanted something else.

“Finish in me…. please” I begged.

He grunted acknowledgment and fucked for a few more strokes, then slammed into me with a single, forceful thrust. He exploded in me and I felt every ejaculation. I needed that today. I needed to feel used again, especially by Lord Jonty.

The three men who’d already taken their turn with me sat at the bar in the main lounge of the yacht. They poured their own drinks as the staff had made themselves scarce while their boss played his games. Stefano remained in his chair, watching. He had a drink in one hand and a cigar in the other, his feet resting on the table.

The other two approached me from opposite ends of the table like they were stalking me, ready to use me. I stood there naked, a big grin on my face. I covered my dick with my hands and giggled, going coy for them. Then they were on me, sandwiching me between them. One of them took hold of my shoulders and brought me in for a kiss while the other groped my ass. He took a little bottle of lube and fingered a load into me and then he bent me over, tapping my ankles with his foot to make me spread my legs.

Bending over made my head level with the first guy’s groin, so I took his large penis and gobbled it down, sucking and licking and making him hard in my mouth.

The guy behind me thrust forward already, filling me up with his dick. It wasn’t big, but it was fat and it stretched my hole. I moaned around the penis in my mouth.

I loved this. I was on full display, bent over, a cock in my ass and another in my mouth, a grateful audience watching intently. Did life get any better than this?

The guy who was fucking me scratched his nails down my spine and I shivered. The other was playing with my ears. I was rock hard and dribbling precum from my dick. “Do you mind if we swap ends?” The blowjob guy asked politely, his accent American but he was very well spoken.

“Sure” the other guy agreed. He pulled out and they switched ends. “Kid, you okay to suck…..”

I knew what he was going to ask. Yeah, I was super okay with ass-to-mouth. Before he could finish his question I pulled him in and sucked him off, letting him fuck that stubby dick right along my tongue. The other guy gently slid his bigger cock into me. It was a great size and a nice shape and it made me shudder. I pushed back, keen to get more of him inside me. After four cocks today I felt I could take a big one.

Both men touched me as they fucked my holes, hands reaching every conceivable part of me and caressing me, scratching me, feeling me. How I didn’t just shoot my load right there I’ll never know. I felt like I was on the edge the whole time.

I stood being well fucked in that position until my legs started to wobble from muscle fatigue. Eventually they realised their dicks were the only things holding me up, so they manoeuvred me to the table and bent me over it, my chest and stomach resting comfortably on the surface. The big man took hold of my buttocks and spread me open, then he pushed his dick back inside me and fucked like crazy. I was moaning, hardly able to catch a breath, when he pulled out and shot a load right up my spine.

There was no time to recover because stubby dick was inside me immediately. He fucked with a little twist of his hip that I found delightful. As he got closer to his climax he kept taking his dick all the way out, then pushing it into me, creating an amazing sensation around my hole. He went on like that, taking my breath away, leaving me gaping each time he withdrew. Then he pulled out one final time and shot a massive amount of sticky goo over my hole, my buttocks and thighs. I could feel it dripping down my leg as I lay there panting, unable to move after my sixth dick of the day.

As I lay there, exhausted and gaping and a little sore, I grinned to myself. I felt so slutty having taken six guys this evening and I was still hoping that Stefano would want me one last time before bed. Sore or not, I was up for that! Today had been amazing.

One of the men got off his barstool and used napkins to clean me up, after which Stefano called me over to sit on his knee. I did so, allowing him to kiss me, hold me, and run his finger around my hole. It was like going back to daddy after my naughty uncles had played with me.

The men were all complimentary while I lost myself, snuggled into Stefano. They spent a good while talking about me, saying how good I was, how much fun this evening had been and how much they would like to replay this game sometime when they could all get together. I blushed. I adored the attention.

Stefano told them he was going to send me to his accountant friend and that he was interested in pointing higher class clients my way for when I got back home. All the men made promises to come see me again and they all said they had contacts or friends who’d be interested in the services of a discreet young man.

Lord Jonti said. “I have a feeling I’ll be making the trip from London a lot more often!”

Eventually I fell asleep on Stefano, my head on his chest and his arms around me. The men stayed up late into the night with me like that. By the time they had finished drinking and smoking and hanging out, a faint grey glow was rising from the horizon.

Stefano lifted me in his arms and took me to his cabin. I was surprised he was strong enough, but he carried me easily and was stronger than he looked. He lay me down on his huge, comfortable bed. He kissing me. I was hard immediately and he saw that as a sign.

He kissed me, sucked me until I came, and then made slow and passionate love to me. His mouth was on mine as he thrust gently into me, playing with my nipples, my ears, my neck, my balls and my buttocks. Wave after wave of incredible sensation washed over me and I allowed myself to get lost in the moment in a way I had never done before. I trusted him completely. It was the nicest, most loving sex I’d had at that point in my life. There was something wonderful about his touch, his passion, the way he seemed to want me to enjoy it as much as he did. He finished inside me and I could feel his dick pulsing and spewing his cum with the energy of a man half his age. We fell asleep together where we had finished, his arm draped over me and our naked bodies still entangled.

“This was our last time, son.” Lord Jonty said to me as he lounged back on the bed. I frowned. I think I already knew it, but hearing that from him made me sad. “I’m too damn old and my health is giving me trouble. Too much drink and smoke, among other vices. I’m not supposed to be flying any more, but I needed to see you one last time.”

“I’m glad you did, but I’d have come to you if you’d told me” I said, and I meant it.

He smiled warmly at me. “I know you would, son. I wanted to have the whole experience, the anticipation while I travel, the waiting for you to arrive. It’s all part of it, you know?” I nodded. I knew.

“I have something for you. I know Stef never gave you as much as he had wanted before he died. That’s true of the others, too, and Carlos can’t do anything since he had that stroke, not with that Power of Attorney in place. Stef aways wanted you to be looked after. I think he was in love with you, you know?”

I nodded. I couldn’t speak. I had a lump in my throat and a tear in my eye thinking about Stefano Valentini and the others. Why did life have to move on so fast? I hated it. I didn’t like change.

“My company acquired a business and, long story short, one of the assets on its books was an apartment block here in the city. It’s small, but it’s the kind of place that will attract well-paid executive types. It’s empty right now, completed just last year but the company never got to move people in before I bought them. I’m not in property. I don’t need an apartment block. So, I have transferred it to you.”

I frowned. A whole apartment block?

Lord Jonty chuckled at my expression. “The apartments aren’t so nice as the one Stef gifted to you. You take it, you get some realtor to rent them out for you. It’s steady income for life and a good asset for your portfolio. The least I could do, son. No more than he would have wanted.”

I took the file that he offered me and I glanced at it. My eyes went wide at the numbers printed in the summary. I went to tell him I couldn’t take it, that it was far too much, but he saw that coming.

“I already sent the paperwork to Max. It’s done. No returns” he chuckled. “Besides, it’s just something less for my kids and grandkids for fight over when I’m dead and buried. They have enough.”

I leaned forward and kissed him, a tear running down my cheek. I felt so grateful, but I was sad that this was my last adventure with Lord Jonty. My last time with the last man from Stefano’s exclusive club. Sure, they’d all recommended wonderful clients and they had all gifted me wonderful things, but sex with these guys was special to me. They had looked after me. They’d gone beyond anything they had needed to do.

And yeah, Stefano had loved me. I knew that. He told me that when he gifted me the apartment. I knew already though. I loved him in my own way, too. He was too great a man not to love.

I stayed there with Lord Jonty. We snuggled on his bed and when I figured enough time had passed I sucked him, got him hard in a way only my mouth could and I rode him slowly, my hands in his and our fingers interlocked until he came in me one final time, our lips together, our tongues exploring each other, our arms hugging each other and holding on for the last time.

He chuckled as he held me. “I haven’t gone for seconds in years” he said. “That’s a send-off I’ll remember.”

I told him I’d always remember it, too. I didn’t want to leave, but he had somewhere to be and eventually his Valet returned to help him get ready. I dressed and left, looking back one last time.

My last day on the yacht was bitter suite. I could have remained there as Stefano Valentini’s sex slave forever, and I would have done if he’d asked. I hadn’t enjoyed a period in my life as much as the two weeks I’d spent with him.

I’d had the privilege of making love with Stefano every single day, sometimes more than once. Plus we’d had the game of strip poker, where I’d taken a record number of dicks and made new friends and contacts for the future. That was pretty awesome and looking back on that evening always excited me.

I think by now the entire crew had seen my naked, witnessed me sucking on Stefano’s cock, or seen him push his dick deep into my ass. He didn’t care one bit, so nor did I.

With just a couple of hours to go until the helicopter arrived to take us away, I wanted one last fuck. In fact, I wanted it like I had never wanted anything. I felt sexy and slutty and full of lust. I stripped naked in my cabin and looked at myself in the full length mirror. I looked tanned, no tan lines. I made up my mind and, taking a big breath, I walked out of my cabin and through the passageways on the yacht, out onto the main deck. I passed various crew members, all of whom ignored my nudity. I knew some of them would glance back at my sweet little bottom as I walked past, and that only heightened my desire.

As I walked out on deck, Stefano was standing at the rail next the pool, looking out toward the shoreline. I tugged at his polo shirt and he turned and grinned at me. With his eyes now fixed on me, I turned and walked to the big double sun lounger. It was like a big waterbed out here on deck. I crawled up onto it, placed one of the cushions under my hips, and lay face down. Then, slowly and deliberately, I pushed my bottom up and spread my legs wide. It that didn’t signal what I wanted, nothing did.

I sensed Stefano had walked over. I heard the soft rustle of fabric as he undressed. I sensed crew disappearing, melting away. Then I felt the lounger move as he climbed up behind me.

Then I moaned as he buried his face between my cheeks and began to lap at my hole. He played with my cock too, pulling it out behind me and licking it, licking my balls and then up to my pouting anus. He gripped my bottom and pulled me apart, still licking and sucking at my entrance. I felt his thumbs probing alongside his tongue, the tips dipping into me and pushing the saliva in, lubricating me. Then they were sliding in, pulling my hole open and stretching me as wide as they could, gaping me.

I whimpered. It was wonderful. Every time the breeze blew it cooled my open hole and made me shiver with intense excitement.

When I thought I couldn’t take his thumbs and tongue any more, he lay down on top of me. I felt his hard cock sliding between my cheeks, rubbing and smearing sticky saliva all along my crack. Then his thrusts became more deliberately aimed, the head of his dick pressing on my ring before sliding away. Over and over, teasing the fuck out of me, until finally, just when I thought I’d have to reach back and make him fuck me, his head was right there. It was in exactly the right spot. He knew it too.

He pushed, all his weight behind his erection, but controlled and slow and gentle. His hard member slid through my sphincter, stretching me out until the head popped inside. The shaft followed until the whole thing, from head to balls, was in me.

I sighed. God, I loved that feeling so much. And when you want something really badly, getting it is always so much better. I moaned softly, so happy.

Stefano raised his hips, withdrawing until his cock was almost popping back out of me, then he pushed down again. It took my breath away, and he did it again, and again, and again. I was being skewered over and over. I started to push up, to fuck myself on his cock until we were both in time with one another. I pushed up, he pushed down, and his dick fulled me to the brim before we both pulled away.

We were both sweating, panting. We picked up speed, holding on and on and on. Stefano was doing a masterful job of holding back his orgasm, giving me a screw to remember. Finally he whispered “I must come….” And I responded with an affirmative moan. He pushed down on me so hard, and I pressed my bottom back with all of my strength. Then, deep inside me, the head of his dick expanded and throbbed as Mister Valentini pumped his seed into my bowels.

I whimpered at the intensity of the sensation. He grunted, like an animal. It was a wonderful, manly fuck and I was so proud of him.

He pulled me back by my hips, his cock still lodged deep inside me. He pulled my torso upright and nibbled at my ear and neck and he took my little dick in both hands. He jerked me off until I came, shooting teenage boy juices over the sun lounger.

Stefano laughed. “You’re amazing. I love how you come. I love being inside you when you do, because everything pulses and quivers. It’s lovely.”

I giggled.

“I will see you again soon. I’ll have to. I don’t know how my life was before I could fuck you every day. I will miss you.” He said.

I slid off his pole and turned to hug him and kiss him.

“I’m going to miss you too” I said.

“When you get back home I’ll introduce you a friend of mine. He will look after your money. You can trust him. He will like you, a lot I think. I will make sure he receives the money you have earned.”

I pulled away. “Thank you” I said. “You have done more for me than you ever needed to do.” I meant that, too. I’d have taken his cock for nothing.

“I am doing what I must. You have been a wonderful lover. I hope you will continue to be. And besides…. I like you.”

We both smiled. He smacked my bottom. “Go get ready.” He said softly.

I got up and walked back into the yacht, sneaking one last look over my shoulder before I went inside.

My hole felt warm, stretched, well loved. It was a sensation I treasured. My heart skipped a beat as I looked back at Stefano, kneeling up and watching me, lusting after me, as I walked away.

I gave my ass one final wiggle for him and some of his cum leaked and ran down my thigh.

To be continued...

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