Flipped - Part 2

All characters are 18+ 

The longer I mulled over the encounter I had with Jake, the more I began to doubt it. Yes, it had answered some of my questions about the elusive straight man, but it also posed questions, too.

Was the promise of money simply more appealing to certain people? Was it truly a case that every person had their price, and Jake’s price had just been one thousand dollars? It felt like my research had answered more about money than it had about straight men, so what was I to do?

Well I knew that certain areas of the city were far more affluent than others, so the luxury boardwalks were indeed a better path to take if I truly wanted to find what I was looking for.

It was interesting to me, because initially I had wanted simply to get a straight man into bed using whatever means possible, yet now that I’d accomplished that, I was becoming greedy.

I wanted a straight man to pull down his pants because he wanted to pull them down, not because he was stuck for cash. Of course, the monetary compensation would indeed remain as a bargaining tool, but my theories needed to be tested so a week after I had emptied Jake’s balls in my hotel room, I returned to the sea side city with a new plan.

Au Le Rox was easily the most exquisite restaurant this side of the country. It sat perched above the boardwalk on a mountainside with views that looked otherworldly. Although fine dining had never been my thing, I couldn’t deny the elegent beauty of the place.

Two white columns stood either side of the entrance where I was greeted by two suited gentlemen who offered directions to the seating area in the back. Rich people baffled me. Did one really require a map to enter a restaurant?

It was a Saturday afternoon, and the place was alive with chatter and polite laughter. I wasn’t there for the food of course, and when I watched a straight spined waiter march toward a table with a huge plate containing one tiny square of something that resembled jelly, I was glad of that fact.

“A red wine” I smiled to my very own waitress, before being presented with a menu in French.

“A nice one” I nodded, and although she looked utterly repulsed by my lack of wine knowledge, she returned a short time later with the long stemmed glass.

As I sipped on it, my eyes scanned the large room. It was filled mostly with older men, many of whom had pleasant young women on their hips. There were some families, too, but only a handful of couples, and if I was being honest with myself, none of the men in those couples were quite what I was looking for.

Of course, I could have approached anybody and tried my luck, but the experience with Jake had left me yearning a younger man. As we grow older, we tend to let our gaurd down a bit more. What would have disgusted us in our teens, becomes meaningless as we age, and perhaps stupidly, I wanted a challenge.

It took a while, but eventually I found my target.

He was a dark haired boy and at first I questioned his age until I watched him order a drink and show his ID. He was one of those whom there was no doubt about his sexuality. He had that air of wanting to be inside a woman, and don’t ask me how I knew.

He was sitting with what I can only assume were his parents, and honestly he looked quite bored. His father wore a sharp suit, his mother, an elegant dress, and it appeared that they were grilling him about something or other.

I watched for quite a while. I wanted to gather as much visual information as I could from the handsome young man. It was blatantly obvious that money was no object where he came from. I could see it in his large, dark eyes, he knew nothing but the finest.

Every so often he pulled his phone from the pocket of his expensive pants and secretly messaged someone without his parents knowing. He’d smile at the responses, scramble another message back, then return to the uneventful lunch.

There was no question in my mind that the young man had no shortage of fans. His muscular arms bulged in his white shirt, giving the impression that he was some sort of athlete. A footballer perhaps.

After thirty minutes my target stood up and excused himself to the bathroom, and now it was my time to shine. I followed him inside, but I wasn’t in the business of being a pervert, so my encounter was professional only.

“You must play football, huh?” I asked, situating myself at a urinal a few stops down from him.

He glanced at me for a second and turned back to the task at hand.

“Golf” he told me, and I cocked a brow.

“You don’t look like a golfer” I smiled, “they’re generally not as… Ripped”.

“I work out” he said, and it was clear to tell that the young man wasn’t exactly interested in having a conversation with a total stranger whilst holding his dick.

“I can tell” I nodded, “can I ask you a question?”

There was a brief pause as he shook his cock and stuffed it back into his pants.

“What?”

I had to thread carefully here. Being open and blunt with Jake had seemed like the right approach for him, but this strapping young man appeared a little more reserved.

“The woman you’re texting at the table, have you told your parents about her?”

I was washing my hands now, and caught him staring at me with a look of confusion on his face.

“Um… No” he said, joining me at the next sink over, “my father wouldn’t approve” he added with a sharp scoff.

“Oh?”

“He’s all about money” the young man continued, “and Lisa isn’t from the right part of town if you know what I mean”.

I nodded.

“How did you know I was talking to a girl?” He asked.

“Because you’ve smiled more at your phone than you have at your parents”.

“You would too, if they were your parents” he sighed, drying his hands. “Why do you ask, anyway?”

I turned to face him now, and the sheer beauty of him was now clear to see. There wasn’t a single hair out of place, every inch of him was groomed to absolute perfection.

“I think you’re very handsome” I told him seriously, “and I came in here to see if you’d be interested in coming back to my hotel room, but I can see that you’re interests lie elsewhere”.

I smiled at him, and he stared at me.

“Good luck with the rest of your lunch” I nodded, patting him on his solid arm and walking from the restroom.

As I enjoyed my second glass of wine, I watched him return to his table with a slight blush to his cheeks. He looked around briefly, but quickly immersed himself back into his phone as his parents desperately tried to drag conversation from him.

There was nothing more I could do. I knew that being too forward with him would almost certainly end with me being ejected from the premises, so planting the idea in his head was my only choice.

It was a crude tactic for sure. Simply asking a straight man to come to bed with me was unlikely to work, but perhaps the stress of his situation would make him a little more open to experiencing some relief.

A little while later, the family stood up and the waiter collected the bill. I watched the young man closely, but he seemed completely uninterested, and he walked from the restaurant behind his folks.

Fuck.

The rest of the patrons were simply not what I was looking for. I gulped down the rest of my wine and shook my head. Perhaps I gave myself more credit than I was worth. Jake had lured me into a false sense of confidence, but it appeared that the wealthy straight man was going to be a little more difficult to flip than the cash strapped teen.

I called for the bill and decided to return to my hotel and draft a new plan.

Three hundred and sixty dollars for two glasses of wine. I rolled my eyes, and handed the waitress my card.

“Oh and this is for you, sir” she told me, and placed a business card on the table.

A futile gesture. The idea of returning to this place for anything other than business was cringe worthy, but as she handed me back my card, my eyes trailed it.

Burlington Golf Club.

I flipped it over in my hand and read the back.

Troy followed by a phone number and a smiley face, or a smiley face that was winking. A winky face perhaps.

I stuffed the card into my wallet, smiled widely at the waitress and returned excitedly to my hotel room. Perhaps my plan had worked after all.

The knock was a welcome one. In the hour since I’d messaged Troy, I debated with myself back and forth about whether or not the young man was genuine, and now that he’d walked into the room, I could only assume that I had been correct.

“Do you live here?” He asked, running his finger along the wooden countertop on which sat the small television.

“No, I’m here on business” I told him as he looked around.

“So you just approach young guys in bathrooms?”

The question stung a little.

“You’re the first” I replied, standing near the bed, “are you always this easy?”

Troy’s shoulders jumped a little. He was laughing.

“So are we gonna fuck or what?”

I cocked a brow. That certainly wasn’t the response I had expected from this seemingly straight young man, but perhaps I had been mistaken.

“Are you gay?”

He turned back to me as though I’d offended him and scoffed.

“Fuck no”

“You’re very eager for cock for someone who isn’t”.

“I want to take a photo of you sucking my dick” he shrugged, as though that was normal, “my father will be furious when he sees it”.

The interaction was becoming stranger than I had imagined.

“You’re going to show your father a photograph of a man sucking your dick?”

Troy nodded, and loosened the string on his shorts. He looked better in shorts than he did in expensive pants, but my guess was that he’d look even better without either.

“Why?” I pressed.

The shorts fell down his legs to reveal a pair of loose fitting boxers. They weren’t my favourite style, but it was what he hid underneath that I was after, anyway.

“Then Lisa won’t seem so bad after all” he smiled, fingering his way into his underwear, “he’d rather a stupid son than a gay one”.

“I see”.

It was clear to see that Troy had never known modesty. The fact that he was willing to show his own father an image of what was about to happen, said it all. His cock hung out over his loose sack, and a bush of thick hair sat on top. Jake had been a whisper of a boy compared to this broad golfer, yet the difference in their cocks was stark.

I had expected a long, thick member, yet Troy’s little rod didn’t suit his body. The skin bunched up at the tip, the shaft was barely larger than a thumb, and the helmet was scarcely the size of a grape.

“It gets bigger” he shrugged, noticing my expression, but I didn’t care about his size.

“Perhaps” I said, unzipping my own pants, “but I didn’t ask you here to suck your dick”.

I stepped out of my pants and sat down on the bed. Troy’s eyes followed me.

“I asked you here to suck mine”.

I lay back, allowing my shirt to slide up to reveal my bulging briefs, and I watched Troy become uneasy.

“I’m not gay, man” he said, “I can’t suck your dick”.

“Pity” I yawned, “it would have made a nice photo for daddy”.

The fact that the bargaining tool had become the young man’s father was bizzarre, but rich people were bizzarre. He pondered for a moment, mindlessly tugging on the small prick between his legs as he did. Boys and their cocks, huh?

“Don’t cum in my mouth” he warned me, “and wipe off the wet shit first”.

“The wet shit?” I smiled, “pre-cum?”

He nodded.

I bunched a pillow up under my head and waited. Perhaps he expected me to do more, because he stood there like a lost puppy until I beckoned him toward me.

“Go on” I said, and I could see the awkwardness in his eyes.

“Is it clean?” He asked, grimacing.

“I don’t know” I shrugged, “I haven’t sucked it today”.

My witty humour was lost on the boy. He reached forward, even though everything in his straight little brain told him not to, and grasped the waistband of my briefs.

“You don’t have like, AIDS or anything, do you?”

The crudeness of the straight man never ceased to amaze me. He didn’t even wait for the answer as he pulled them down to reveal my cock.

A decent cock it was. Seven inches hard, large and plump when soft, and protecting a long set of balls which were endlessly full. He stared at it.

“No” I told him, “I don’t have AIDS”.

Troy faced off with my cock for quite a while. The cogs in his brain spun rapidly, as though he just now realised what it was he had agreed to do. His tanned skin had become almost green as the waft of my sweaty junk poured over him.

“In your mouth” I smiled, pushing him, “you’ll feel better for it”.

The muscular golfer squirmed. His face bunched up with a brief look of disgust, and evidently it was the image of his girlfriend which spurred him on.

His touch was rough, as though he was trying to show me how much he didn’t want to do this, yet he was doing it anyway, and I certainly hadn’t forced him to.

He squeezed my cock in his fist, watching the head bulge out from the gap in his hand, and then wanked it like he was throwing dice.

“You don’t have to rip it off” I told him, and he eased up slightly.

“Wipe it” he almost gagged after a minute, and I could see a bead of pre-cum leaking down my erect shaft.

I rolled my eyes, but wiped it away with my hand, and Troy returned to the job.

“You’re going to need to suck it if you want the photo” I laughed, but the young man didn’t appear to be in the mood for jokes.

He took a breath, stopped when he realised my cock musk accompanied his oxygen, and rapidly sucked the head between his lips, before pulling away and gagging violently.

“I can’t” he choked, “that’s fucking nasty!”

“Good job I’m not very sensitive” I smiled, slowly jerking off now that Troy was on the verge of puking.

“No… I don’t mean… I just mean…”

“I’m kidding”

He looked back at it for a moment, before gingerly approaching once more.

“Wipe it again” he told me, and I shook my head.

“Taste it”

He gawped at me as though I’d just asked him to cut off his little tool, which still remained visible.

I took out my phone now, eager to get him back on my cock, and waved it at him.

“Don’t you want a photo for daddy?”

He considered it once more and crawled back onto the bed.

It appeared that he was mentally trying to prepare himself for the hellish ordeal of sucking a cock, but when he finished, he grabbed my boner once more and plunged his head down on it, until he gagged.

I expected more theatrics from the handsome young man, but he remained impaled for a moment, bobbing up and down, slurping and choking as he nursed on my cock.

I could feel the pre-cum pouring from my slit, but Troy was either ignoring it or enjoying it because he continued sucking.

I could only liken the experience to sticking my cock into a meat grinder, though the more he practiced, the less teeth he used, until finally, he slid up and down using only his lips, tongue and throat.

“Better” I mumbled, laying back as Troy gagged.

“Photo!” He growled into my cock.

He looked good in it. His eyes red from choking, his cheeks red from embarassment and his plump bare ass visible in the background. The fact that he planned to send this to his father was absurd, but who was I to judge?

The inexperienced blowjob continued for another twenty minutes until Troy looked utterly exhausted. At one point he rested his head on my tigh and continued to suck using  just the suction in his mouth.

With one last attempt, the fit young man bobbed hard, taking my entire cock into his throat and staring up at me as though his gaze would make me nut. Perhaps it was an interest of his, but it wasn’t his eyes that made me cum.

“I’m going to blow” I told him, expecting him to pull off and let me spill my seed across my stomach, but Troy remained in place.

“I’m going to cum, man” I growled now, wondering if he hadn’t heard me, but again, he didn’t move.

It was too late to warn him a third time. As inexperienced as his mouth was, his throat needed only to pulse, and pulse it did. The muscles contracted against my helmet, coaxing an orgasm out of me, until finally it swarmed and I gasped.

“Fuck!”

He winced as the first explosion of sperm coated the walls of his throat. The swallow wasn’t voluntary, but it happened anyway, and now I was pouring my cum directly into his stomach.

He squirmed, pulling off so that I emptied more of myself into his mouth. The look of disgust on his face became stronger as semen spilled from his lips and down his chin.

Another photo for good measure, of Troy covered in spunk and more of it shooting from my prick and drenching his cheek.

“Ugh!” He snapped, wiping the mess from his face, “that was gross!”.

“Tell your cock that” I smirked breathlessly, pooling cum into my bellybutton as the humiliated golfer looked down at his five inch erection.

“Send me those photos” he mumbled, wiping his face on the bedsheets and scrambling for his clothes, “and don’t message me again after that”.

He almost ran for the door as I lay back with a sigh of relief.

“Straight men” I laughed to myself, and my cock gave one more twitch.