Infiltrating The Rich (WT) (Patreon)

Howdy folks! I have a short one for you today, because I'm looking for some feedback. 

This isn't a story exactly, more of an overview of a story. I'm playing with this idea for either a series or a novel, but I'd love your input. Don't worry, I haven't given away much in this sample, just a general idea. Let me know what you think! 

All characters are 18+

It started as a joke. In fact, it started as a bet. Could I, a nobody in the ever changing landscape of high school popularity, somehow infiltrate those who were most popular? The jocks, the cheerleaders, the sports stars and rich kids, the snobs and the bullies, all of those people who made high school a living nightmare. Could a nerdy young man like me, really do it?

I didn't think so, but apparently it was worth a try, and my best friend Glen was my number one supporter.

"They're idiots!" He told me, "all you've got to do is pretend you have money and those dipshits will be all over you!"

I didn't think he was right, but he proved me wrong, and when I went to school the following Monday wearing all of the designer clothes that Glen and I could possible get our hands on, it almost happened naturally.

So here I was, six weeks into the strange joke slash bet that had gone much too far, with my pants around my ankles and the captain of the football team slamming in and out of my asshole with such force that I had to hold onto the star wrestler of the school who was pumping my mouth with his thick cock.

How did I get to this point, you might ask? Well, it was much simpler than I had ever expected.

Trey Summers was the dumbest person I had ever met. Truly, the guy was a complete moron, yet he was somehow a school celebrity because he was six foot five and was made of mostly muscle. He was so dumb, in fact, that when I finally received an invite over to his place for some ridiculous popular people only party, it took only a suggestion for him to fall right into my trap.

Yes, I had gone too far. The aim of the bet was only to see if it could be done. If someone like me could really fit in with people like them, but it had all been too easy. The excitement of the chase lasted less than a few hours, and now I was the one with the power.

"Everyones doing it now" I told Trey as we stood in his bedroom whilst the party raged on downstairs, "it's not even considered gay anymore, it's literally such a normal thing to do".

"You want to suck my dick?" He asked again, scratching his blond head, "like, you... A guy, you want to suck my dick?"

"I don't want to suck it" I lied, because as dumb as Trey was, he was also incredibly handsome, "but I'm willing to suck it, because we're friends now, and that's what friends do, right?"

It was like giving candy to a baby. The dumb brute shrugged his shoulders, kept his look of confusion, but pulled down the front of his pants to reveal a chubby cock which fell out from a bush of pubic hair.

I sat on the edge of his bed and handled his tool carefully. As a virgin, playing with cock wasn't exactly second nature, but Trey simply stared down at me as I fumbled with it and finally took it into my mouth.

"That's not bad" he remarked as he grew in my mouth, "it feels like a chick doing it".

I felt him swell and his cock head become wet as I slurped on his organ. Each wet stroke of my tongue made him produce noises and pre-cum, and I swallowed it down eagerly.

After a while, Trey grunted and squirted ropes of thick cum onto my tongue, and I made sure to swallow every drop and return for the clean up before releasing his pole.

"This stays between us, right?" He asked, and I nodded.

But I was wrong. It didn't stay between us. In fact, it began to spread like fire through the group, and as angry as I was initially, it was the best thing to ever happen to me.

The girls stopped hitting on me, which was fine by me. The only reason they were hitting on me in the first place is because I told them all that my dad sold mansions to rich people, when my dad was in fact, a janitor in some middle school.

Some of the guys stopped showing much interest in me, but not many of them. Somewhat ironically, the same young men who used the word faggot on a daily basis, suddenly became much more interested in me, and I began to receive Snaps in the middle of the night.

What's up? Accompanied by suggestive images of bare legs, flexed biceps, or even the elusive underwear shots.

I'm bored. Anyone coming out? Messages, which had most certainly only been sent to me.

And of course, the accidental dick pic that wasn't meant for you.

Yes, the plan had gone too far, but I wasn't one bit upset about it.

"I think you should stop now" Glen said angrily one day, as I replied back to a photo of Cameron Greyson's sperm pool which he had sent with the caption, I know the maid likes finding these.

"I will" I lied, "I just have one more thing I want to do".

Cameron Greyson wasn't some meat head with more muscle than brain, but he was devilishly good looking and had the attention of every single chick in school. It felt like a challenge, and that's exactly what I viewed it as.

Sure, the prize for winning such a challenge was amazing, but first I had to actually win it.

"We're friends" I told him, as we sat alone in his car, "it's not that weird, it's just what friends do".

"I ain't no fag" he said, eyeing me angrily, "you think I'm a fag or something?"

"No, no" I said, questioning the multiple photographs of his semen, "but what's the harm?"

And that was it. There seems to be some common misconception that flipping straight boys was some difficult, if not impossible feat that is rarely achieved, but the secret sauce is simply getting in at the right time, in the right place, and that is what I'd done.

His cock flopped out from the waistband of his shorts as he slid his chair back, and I wasted no time in wrapping my lips around it. Cameron stayed quiet and simply watched me as I got to work, and even though it took quite a while, eventually he got into it.

"Play with my balls" he moaned, holding the back of my head as I gagged on his meat, "squeeze em'".

I sucked and squeezed, and my own cock leaked into my underwear as I gave head to the straight wrestler. He eventually blew his load deep into my throat, and I had no choice but to swallow it. When we sat back, he pointed his finger at me and once again, I was warned to keep quiet. I did, but he didn't.

It became a game for them. As much as they wanted our sexual escapades to remain secretive, they couldn't help but share their sins, because suddenly I wasn't the nerdy nobody anymore, I was something that other people had had, and that was the key to flipping these popular, rich young men.

It was almost like I was some type of designer shirt. If one person had me, then that meant that I was worth having. And if one person had me, then the next person needed to have me, and so on, so forth until I became the cock sleeve for almost every single fucking guy in the group.

Glen became distant, because I wasn't riding my bike to school with him anymore. I was pulling up in Cole Benson's Ferrari, with a stomach full of his spunk and a grin on my face.

I wasn't spending Friday night's at Glen's place, making prank calls with a bottle of stollen vodka anymore, because I was bent over in Cameron Greyson's bed, getting my ass ploughed and sometimes sharing the pleasure with one of the other handsome young men in the group.

I wasn't doing anything with Glen anymore, because I was doing everything with the popular rich boys, and that is how my life was flipped upside down.