A Working Boy

Max came out of his office, all white teeth, fake tan, and custom fit clothing. He extended his hand and we shook.  

“My favourite client!” He exclaimed. That was his usual opener and I was pretty sure he used it with all his clients. “Come in, come in. Jackie, flat white please for him. I’ll have my usual. Come in… sit down….”

Max was my accountant and financial guru. He’d been looking after my financial affairs for a long time and he was one of the guys who had first planted the seed that I could be better off on my own. We no longer fucked, more’s the pity, as he had gotten himself into a long term relationship with a billionaire’s cute son. That said, it had become customary to run through the numbers before I earned my discount by swallowing his cum.

The numbers made my eyes go wide. We hadn’t done a full review for a while and I was way ahead of where either of us thought I’d be at this time. Max gleefully informed me that I could easily and comfortably retire now if I wanted, with investments and cash reserves far ahead of plan. He winked at me. “You must have been working hard, young man….”

I smiled a genuine big warm smile and I had the good grace to blush a little. I never worked hard and we both knew it, but Max had worked damn hard on my financial position over the years, making the very best of what I had earned and been given.

He handed me an envelope and told me to open it. It was an incredibly ornate wedding invitation and I was sure the lettering was real gold.

“You two finally tying the knot?” I asked.

“He convinced me. Besides, his ass is the only one I liked better than yours.” And he laughed then winked. “Well, maybe the same, not better.”

“I guess no more discounted financial services…?” I said with a mock frown.

Max laughed at that. “Don’t worry my friend. Ahmel knows about our arrangement. Always has. He doesn’t mind you polishing my little man from time to time, as long as I go home and tell him all about it!”

I laughed. I didn’t know Max had kept his boyfriend informed about me, but I was glad he had. I put my empty coffee cup to one side and slid down under the table.

“I think you’re going to be my favourite client!” Max had said gleefully after I had slid under his desk and opened wide to take his cock in my mouth. I’d been sent there by Stefano’s people, through Danny. “The boy needs someone independent to manage his resources and Maxwell will work for alternative forms of payment” his messenger had said.

Max’s dick was big and meaty and hairy. He wasn’t merely well-endowed, he was really big, thick, with a bulbous purple head that bobbed up and down with his pulse. Sucking him was a delight, with so much of it to get my lips and tongue around. If I could take this guy in my ass, it would be the biggest thing I’d ever had inside me. I wasn’t usually a size queen, but I was feeling adventurous and I was desperate to see if this thing would fit.

“There’s a plus one on that invitation, you know…..” Max said as I kelt between his legs and extracted his monster cock from his pants, bringing me back to the here and now. I looked up at him, his dick in my hand and my tongue circling the tip of his little soldier. I hoped my look said “you really wanna do this now….?”

Max leaned back in his chair. “You’re right” he said. “Time to talk later…..” And I slid my mouth down over his purple head until it hit the back of my throat. I sucked and licked and used the tip of my tongue around the head of his penis, just how I knew he liked it. I always knew when Max was close. He would spread his legs a little wider, that was his tell. I let him impale me right down my throat several times and then I felt his monster cock expand with a rush of blood before pumping his delicious salty seed right down my gullet. I swear, there’s no rush like a truly massive cock spewing gunk down your throat. I highly recommend it.

I sucked the drops from his pee hole and crawled back out from under his desk. I sat on his lap and we kissed a little, giving him time to catch his breath and get his head back on our business.

“You’ve been practicing” he said. “That was ohh so good!” And he grinned. “Or maybe it’s that talk of your growing wealth makes you hornier than usual.”

I chuckled at that. It was true, the knowledge that I had amassed quite a sizeable fortune entirely through the use of my own assets always made me horny for more. “You sure you don’t want to stretch me open, stuff that big fat dick in my tight little hole……” I said with a cheeky smile. I missed taking Max’s dick. It was one of life’s challenges.

“You want to stuff that big fat dick in my tight little hole, mister?” I said with a cheeky smile. His eyes had gone wide, sitting there in his office chair with his cock pumped full of blood and standing tall out of his fly.

“Fuck it” he said, and he took hold of me and yanked my jeans down to my ankles without even pausing to unfasten them. He pushed me back onto his desk, laying me down on my back with both legs, tangled in denim and briefs as they were, slung over his left shoulder.

Max had initially been reticent to screw me. He wasn’t sure someone of my age could take him. I often found that a little tongue and throat action could change a guy’s mind about that.

He reached into a drawer and grabbed a tube of lube. It was cold when it touched my hole and I flinched as he fingered it into me, first with his index finger, then two, then three. He moved with urgency, sexual desire and lust driving him on, but he was still gentle and careful. He didn’t speak or look me in the eye, keeping focussed all times on stretching my boy pussy with his fingers and watching the show. For my part, I loved it. I knew this would be a challenge and that made it like my first time all over again. I relaxed and closed my eyes, waiting for the electric sensation of a man’s cock touching my hole. I had butterflies.

Minutes of being fingered went by, my eyes shut and dark but my mind in glorious technicolour. Then the fingers slid out, leaving me stretched open, relaxed and ready. And then his penis was there, big and meaty and ready to take me. It felt huge.

I took a deep breath as he pushed against me. I had been fingered and loosened more than ever and not many people took the trouble, but this guy knew what he had between his hairy legs. I could feel the pressure of his flesh against mine. I could feel the muscles in my anal ring begin to give, to stretch and part as this monster dick kept up the forward pressure. My hole started to sting, stretched so wide as it was. I shuffled on my back, wiggled my hips and breathed deeply. I pushed out to meet him. I tried every trick in the book, but it was slow going. It was hurting too, that wonderful hurt that I craved so much, possibly the only pain I never shied away from. Even so, I wondered if maybe, for the first time, I’d met a dick I couldn’t accommodate.

But then, as my mind actually began to question whether I should throw in the towel, his head literally popped inside me. I gasped. I knew he hadn’t torn me, but that’s what it felt like for a whole minute. Then my sphincter got used to gripping his mighty shaft. I opened my eyes and met his gaze. He was dripping with sweat from the effort and the sexual tension. As our eyes met, he surged forward again and drove that thing up inside me.

My eyes rolled back in my head. My god….. I’d never felt so full, so stretched. It felt like two dicks fucking me.

“So, will there be two of you…..?” Max asked, all innocent. “At the wedding?” He was always trying to set me up, keen to see me in a real relationship. Max was one of the few people who I felt really knew me. We liked each other. I think he knew I got lonely from time to time and he always wanted to make sure I was okay. It had started out as Max following the instructions from our mutual benefactor, but our friendship had quickly become genuine.

“Well......” I said. “Maybe. There’s a guy I like, but I’m not sure. He’s barely in his twenties for Chrissake! Inexperienced and young. But man, is he hot or what? For some reason I seem to really like him. I don’t get it.”

Max guffawed with laughter. “Oh my dear boy you’re priceless!” He said. “Sexually so experienced and yet so naive in the ways of the heart. Listen here, you can’t help who you fall for. It’s that simple. Just make sure he’s not into you for your money.”

I smiled. “Thing is, he’s got more money than me. Or he will have. His father is worth millions.” I told Max how I met Ethan. That raised some eyebrows and he told me off for having sex again with “that reprobate Johnny Ladd”. I told him about our few days together, about telling Ethan what I did for a living. I told him Ethan had confessed he didn’t need to work, that he stood to inherit his father’s fortune. He’d told his father that he didn’t want the business though, that he wanted to go his own way. So, he got himself what he called an ordinary job where he’d meet ordinary people, working as a waiter in a coffee bar.

“I’m meeting him today. We’re going boating on the river and having a picnic.”

Max chuckled. “Very boyfriend-like. A proper date. I’m impressed. You’ll give me his details so I can run a little background…..?” I nodded. I didn’t feel the need, but Max would never let it go if I didn’t allow him to satisfy himself.

“You’ve always been good to me, ever since Stefano introduced us. I appreciate it” I said, and I kissed him on the cheek.

“Oh… enough with you!” Max said dismissively. “I seem to remember you being very good to me over the years.”

I thought back to that first time. He grunted, sweating like crazy and short of breath. “My word, so hot and tight…..” He growled at me.

“Come inside me, please” I begged, and I pulled his face down to mine so I could give him a passionate wet kiss.

“You’ve already been so very good to me” he said. “Are you sure?”

“Don’t hold back Uncle Max” I said in my best little boy voice. “Just fuck me as hard as you can.”

He pounded that thing into me like there would be no tomorrow. I moaned relentlessly. I was so full, so gaping wide, and it felt like my insides had been permanently rearranged. It was a magnificent fuck.

He surged forward. My legs slipped off his shoulder so he pulled me onto my side in a ball on his desk. Gripping my thigh he thrust once more, then twice, and then his dick exploded inside me. I felt every single vein popping, every twitch of his member as it spewed cum into me, painting my insides with hot, thick juices. There must have been bucket loads of it pumping out and I whimpered completely involuntarily.

Eventually he was totally spent, the last aftershocks of a mighty orgasm fading away. He pulled his softening dick from me along with a flood of cum. I reached back to touch myself. I was gaping open, sticky and wet, and I was exhausted. I honestly wondered if I’d be able to walk!

Max grabbed a small towel from a side drawer and pressed it to my hole. He took another to wipe himself. He sat heavily back into his office chair. “My boy” he said wearily. “I’m going to make it my life’s work to ensure you’re a very wealthy young man before you’re 21. How does that sound.”

I sat up, keeping the towel under my ass as I was still gaping and leaking. “It sounds cool!” I said. To be honest, retirement sounded boring but being wealthy at 21 sounded pretty neat. Stefano said he’d make sure I was looked after by people I could trust, so I assumed Max would be true to his word. Of course, this was long before I really understood anything about money, just that I needed cash so I could leave home.

I got off Max’s knee. “I’d better go or I’ll be late for Ethan” I said. “It was good to catch up. Seems you’re still on track with your promise” I winked at him.

“Cheek!” He exclaimed with a broad grin. “I’m three years ahead of my promise and you know it. Now go and make like a boyfriend. I’ll see you for dinner in a couple of weeks. Let me know if I need to…er….expand the booking to accommodate two people….?”

I laughed and left. Max was incorrigible.

I got to the place where we were going to rent a rowing boat but Ethan texted me to say he was running twenty minutes late so I sat with a coffee looking out over the water. I loved the way the sun glistened on the surface. It took me back.

I sat with my feet dangling over the stern of Stenafo’s yacht, dipping them into the Mediterranean Sea. The setting sun was creating a light show in the waves that I found mesmerising.

It had been a long and tiring day and I’d been dumbfounded for most of it. I had been collected by Sefano Valentini’s driver. I was taken to the airport where I was met by one of his private secretaries who escorted me all day. She was lovely, delighting in ensuring I was treated like a prince off on an adventure.

Everything was first class, so very different from my day-to-day life. I flirted with the guy in charge of the first class cabin on the flight and watched movies and when we landed at Nice in France, we were taken off the plane first so that we could be taken to the helicopter that was waiting for us. From there we flew direct to the Valentini yacht, a huge boat called “Le College”. I got the joke right away and chuckled as the helicopter landed on deck.

When Stefano arrived soon after. I couldn’t believe how many staff were on this yacht and I smiled when they all lined up to greet him. I wondered if I should line up too, but the secretary waved me away. “This is for the staff” she told me. “You’re a guest.” I felt great hearing that. Very swanky.

Stefano greeted me warmly, like an old friend. I liked that. He showed me around, telling everyone as we went that I was to have absolutely anything I wanted. He showed me to a wonderful cabin that was full of clothes in my size that I loved. I asked him what his expectations were and he put me at my ease immediately. “Let’s just see how we go. This is your cabin, your own space. If ever you want time alone, come here. And if ever you don’t want to do something, you let me know. Is that okay?”

I nodded. That sounded great.

“Now, how do you feel about changing into these for me. I had them bought with you in mind.” He tossed me a pair of skimpy red swimming trunks that made me feel sexy just looking at them. I stripped off quickly, wiggling my bare ass for Stefano as much as I could while I pulled the tight red trunks over my bottom. There was almost nothing of them and I totally loved them. He asked if I would be comfortable wearing them around the pool or on deck if other people were onboard and I nodded vigorously. “Good” he said with a warm smile. “I’m keen to show you off. There are other colours, same style.”

I stepped into Stefano and put my arm around him. He responded by running his hand down my naked back. “I’m all yours” I said to him. “I mean it. That’s kinda my rule. While I’m here, I do anything for you.”

“I’m all yours!” Ethan said as he rushed over to me and sat next to me, out of breath, snapping me out of my daydream.

He was dressed in smart khaki shorts and a black short-sleeved linen shirt with white deck shoes. He was smouldering in his outfit and I wondered once more how this young guy had managed to grab my attention. He was hot. That was undeniable.

We hired a row boat and set off. After some messing about on the river we pulled into the bank in a secluded spot and spread out a blanket for a late lunch. I went to grab the picnic basket, but he took my wrist and pushed me onto my back. He lay down, half on top of me, and kissed me.

“So you gonna tell me why you kept me waiting?” I said with a giggle. “Rude!”

He kissed me again and I melted into his arms, the heat of the sun on us as we made out. The guy could really kiss, on top of his other attributes.

He pulled away and looked me in the eyes. “After having spent some time with you like we did, I thought it was about time I came clean to mom and dad. I’m late because I was meeting them for a late breakfast. I came out to them.”

I had a sudden pang of guilt. Had he done that for me? He kissed me some more, running his hand under my t-shirt so he could touch my body. His hands were warm, smooth, and his touch was electric. I asked him how it went, nervous to hear.

“It was fine. They said they have known for a long time. Dad wanted to know if that’s why I didn’t want to take over his company and we had that conversation too, long overdue. We cleared the air and it was good” He rolled off me and propped himself up on his elbow, a broad and impish grin spreading across his face.

“And…….” I asked, now worried.

“And I told them I was seeing someone. Don’t worry, I told them it was early days and that you might not be as interested as I am.” He paused theatrically before adding “And I told them you slept with older guys for money.” His grin turned into laughter at the rare look of shock on my face.

“Wh…..” I couldn’t speak. I was confused, and that wasn’t like me. I wasn’t sure why I cared, but something inside me seemed to be telling me that I did. What was this boy doing to me….? And I kept coming back to the question, if he was seeing me, did that mean I was seeing him….?

“It’s okay. Dad was impressed that you were almost able to retire off it. Money impresses him and it turns out he’s way more open-minded that I thought. Mom just said she supposed it was a sign of the times. I think she’s just happy that Dad and me are speaking again.”

I laughed and pulled him in. He kissed my mouth, then my chin, then my neck, moving down my body until he pulled my shorts down and kissed me some more, the sun shining down on me as he took my cock in his mouth. Being sucked in the sunshine is quite delightful.

Stefano pushed me back on the sun lounger and peeled the bright red swimming trunks off me, leaving me naked in the sunshine. The staff around the pool area seemed to melt away as their boss pushed my knees apart and kissed down my torso to my cock.

After only a few days I was used to him taking me whenever he wanted, no matter who was around or where on the boat we were. So far he’d fucked me on a bar stool as I leaned forward over the bar, in the main lounge on a fluffy rug that tickled my balls, and this was the second time out here by the pool. We’d fucked in his cabin, too, of course. Stefano was a virile man and a very generous lover. Sex with him had been brilliant and I was thoroughly enjoying being here with him.

He pulled me down the sun lounger and taking both my ankles, he spread my legs as far as they would go. “You put it in” he said. I reached down and took his dick in my hand and fed it into my waiting hole. I closed my eyes and took a deep breath as he gently slid himself all the way in.

“I love how much you enjoy taking cock.” He said, smiling at me and rocking gently back and forth. “And I adore watching it slipping inside you. I feel very privileged.”

I loved the way he spoke. Most men treated me well, but this guy was on another level. He was kind and caring and despite paying for this, he always spoke like I was doing him a favour.

“I can’t believe I’m even here. I’m having such a fantastic time! And I can’t believe you manage to get it up so often! You’re a naughty daddy.” I said with a grin.

He kissed me, letting go my legs so they were free to wrap around his torso. “I have some friends coming out here tomorrow for a game of poker. Are you up for me introducing a couple of my friends to you? You don’t have to, but it might get interesting.”

I sniggered and pulled him in with my legs, taking in the sensation of his dick sliding further inside me. “Do you mean interesting….or INTERESTING….?” I asked with a giggle.

“Oh, the second one!” He said and he flexed his hips several times in a row, really fucking me.

I ran my fingers through his grey chest hair. “I’m up for anything Mister Valentino” I said. I could tell he loved being called that when he was fucking me. It turned him on completely. He took hold of me in his surprisingly strong arms and fucked into me hard and fast. For an older guy he could really move. I was breathing heavily in no time.

I was breathing heavily on the bank of the river. Ethan could make a living sucking dick, about that there could be no doubt. I tried to push him away because I was close already, but he took hold of my wrists and held my arms away from my body and continued to bob up and down.

“Ohhhhhhhh” I moaned. I arched my back up off the blanket, but he pushed me back. That was it. There was no turning back now. He was sliding his mouth up and down my cock, pushing it into his cheek with his tongue and still managing to suck at the same time. It was too slow, too sensuous, making me feel every second. Now, finally, it was too much. I cried out and came in his mouth.

He continued to suck and he swallowed every drop, using the tip of his tongue to lick the last tiny droplets from the end of my dick. I was panting, hot and sweaty.

He giggled. “Mmmmmm that was tasty” he said, working his way back up my body to kiss me. “I figured it was time I did that for you. You’ve done it for me enough times!”

I hugged him tightly. It wasn’t often someone swallowed my load. Only the best people in my life had done that.

I lay back on the sun lounger, Stefano fucking me hard until he came. Then he made his way to my dick and sucked me as I lay panting. As he licked and sucked my cock, he fingered my sticky, gaping hole, pushing the cum that had leaked out back inside me.

I went to push his head off me, not sure it was good customer service to cum in my client’s mouth, but he swatted my hands away. I came quickly, pumping my juices like only a teenage boy can. He lapped them up and swallowed the lot.

“Sweet and sour” he said with a smile. “I love the taste of your cum”.

I giggled.

He lay down next to me on the lounger. We were both naked and I was starting to leak again, but that didn’t stop him waving for a drink to be brought over to him. I giggled again. This guy was shameless and I was beginning to realise that he loved it, delighted in his people seeing him with me, his prize boy. It felt great that he liked me enough to want to show me off. I had to admit, most customers before Stefano wanted a secret adventure, something that no-one must ever get to hear about. I found I enjoyed being on display, knowing he could turn me over and screw me any time.

“You gonna turn me over and screw me?” I asked with a cheeky grin

“You want to? I figured I’d just suck you off….?” Ethan said.

“You going off me already…?” I asked, fake-pouting.

He raised an eyebrow and forcefully rolled me over. He quickly stripped me of my shorts and underwear and buried his head in my ass. The sensation of his tongue right there so soon after I had cum took my breath away. He wasn’t there long. He stripped off his bottoms, lay down on top of me and forced his cock inside me. He was rough, but I sensed he was constantly checking that I was okay with it. And I was. This guy had now fucked me just about every way possible and I loved a rough screw once in a while.

He used his legs to force mine apart and he pumped me full of cock. I moaned, and I took it. It didn’t take long before he thrust one final time, a huge and forceful surge forward. I felt him expand and fill me up with hot, salty goo.

He rolled off me immediately to lay on his back, panting. “Nope” he said.

I was confused. “Nope…what…?” I asked.

“Nope, I don’t seem to have gone off you.” He said with the huge grin. I pinched him and we play-fought, rolling over each other and giggling. He caught me, pulled me close, one arm hugging me and the other hand grabbing my bare ass. He slid a delicate finger into me and I stopped struggling.

“That’s cheating.” I said.

“I hadn’t realised there were rules” he said with a snort.

“Here are the rules” Stefano said to the five men sitting around the table. They were all older, all wealthy, all handsome. It made my heart skip a beat. I’d do any of them, which was good because form what Stefano had told me, I might be about to.

“Strip poker with a difference.” He said. “The first person to get naked has to satisfy my boy, but you lose any money you have in the pot. I call this one Swingers and Roundabouts” he chuckled to himself at his joke. “When each pot is cleared, it’s off the table. The pot goes to my boy, because we’re starting an investment fund for him. Any objections.”

Each man looked me over with open appreciation. There were swift nods and “aye’s” of agreement. One of the men leaned forward, his eyes on me the whole time even though he was addressing Stefano. “You have outdone yourself Stef.” He said. “Exquisite….. simply exquisite”.

I blushed. This was going to be fun night. All seven of us, together.

“So, are we together?” Ethan said out of nowhere.

I blushed furiously. That had caught me off completely off-guard. He grinned at me knowingly.

“B….but….. the thing is……” I started. I had never been so torn. I’d never been this far into a relationship with anyone. But equally, I wasn’t ready to give up my lifestyle after a few days of screwing around with someone who wasn’t even my type!

Well, maybe he was my type. I didn’t know any more!

He put a finger on my lips. “I’m not suggesting anything. I know what you do - “ he shrugged “- and I don’t give a fuck.” There was a long pause, his finger on my lips, my face red, him grinning. “But I fancy you completely and I want you to be my boyfriend.”

“Even though I……”

“Yep” he said, cutting me off and being too damn simplistic about it.

“But I’ll be slee…..”

“Sleeping with other guys?” He interrupted me again. “I believe that’s central to your work.” His grin was broad and he wasn’t going to take ‘no’ for an answer.

And every cell in my body was screaming at me to say yes.

“Okay then” I said with a shrug. Hell, if he didn’t mind, why should I?

To be continued. 

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