Cheerboi Origins Pt. 01: Femboy World

"Holy...it worked."

"Fuck yeah it worked, Jimmy. It's done, the deal is signed and executed. Knudson Industries is now the proud owner of Hooters."

I could barely speak, I could barely even think! I fucking did it!

"That's right, I actually just texted Mr. Knudson before you came in. He said this was perfect timing, in fact. I told him that you're the one that got it done. I mean, I took lots of credit myself - share the love, right? After all, I'm the one that brought you up in Knudson Industries."

"So...what does this mean?" I asked, still processing.

"Good question. First off, you're obviously getting a promotion. Second, Mr. Knudson wanted to thank you for your hard work. He values loyalty and hard work around here."

"How?" I asked.

"You know, you haven't asked what we're going to do with Hooters. Aren't you curious?"

"I mean, I assumed what we do with all companies. Load a bunch of debt on them and then sell them off for a huge profit."

"Hahaha, you definitely know our M.O. well. This, however, this is a special acquisition for Mr. Knudson. He wants to do something special with it. In fact, we're transferring management over to the Amusement Park division of the company."

Oh my, the amusement park Division. Only the best of the best work there. I just punch numbers and read memos. But the men who work in that Division get certain perks that are only whispered about. It was basically like a myth about the benefits those guys received. Hell, the park is 60 miles from our office building. Few, if any have seen the park or even afford to go there. But the men who did get a chance to go the park never came back to work. Our supervisors would just say they transferred divisions. We would see the occasional Instagram post from them with them next to a whole host of tantalizing femboys.

And Mr. Knudsen wanted to thank me? He doesn't talk to anyone. No one at my level has seen him. We don't even know what he looks like. There are no pictures of him or anything. Only assumptions about his appearance. We started to think about whether he was actually a person at all or just a code name for some reclusive CEO.

"And you are actually going to be one of the first to try out the new version of Hooters. Expect an invite in the mail in a few weeks once it's re-vamped."

"Wow...this is incredible." I couldn't believe it, i was a fucking big deal in this company now!

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A Reunion of Sorts (POV: Mr. Knudsen)

I hate being upstaged. I hate having rich friends. Even rich acquaintances. This man is making me stand on a private dock waiting for his own private helicopter to meet him on his private yacht.

"Right this way Tommy. Your yacht awaits." There is something blasé about the wind hitting you from the helicopter blades.

And his yacht is in the most perfect water, clear blue and pristine. Take one step onto the yacht and it just scream luxury. Beautiful women all over the boat with the finest luxury stuff.

If he means business I will mean business too.

"Hello, Mr. Diamond."

"Oh fuck off, Tommy! You know I hate when you use last names. That's your 'I mean business' talk. So annoying."

"Fine, Dirk whatever. Let me get straight to the point..."

"Ummm, Tommy. I like to be wined and dined first before you fuck me."

"You haven't changed since college, huh?"

"I see you still haven't graduated college, huh?"

I fucking hate Dirk. But he is one man I respected from college. He was the first millionaire from our class. Super successful and the absolute perfect degenerate to get this new project started.

"Dirk, do you remember that wings and breast event you had back during our junior year?"

"God, how could I forget? That was the one where that broad Amy won. Dude, I bought this superyacht by the way. I call it The Cockfighter. Funny shit huh? But that's not the point. The point is she was the first one to suck my prick on that boat. She still has it, I tell ya."

"Yeah, that's not where I was going. But congrats on that. Do you by any chance remember someone named Daphne?"

"Daphne? Daphne? Daphne? No not really, why?" Dirk says tapping his chin playing like he's attempting to remember.

"Daphne was the flat chest girl you refused to let participate because her tits didn't bounce so I had to convince you to let her join."

"Well, no shit I don't remember her."

"You would remember that she came in second."

"No one remembers second place, Tommy."

"You will start to remember because Daphne was actually, Daniel Myers, from our Econ class that spring semester."

I watch Dirks eyes go wide. As if a couple screws became loose and they're trying to tighten up again. "You mean to tell me... you brought a dude to my fucking wings and breast event? I jacked off to a dude?!?!"

"Yes, Dirk. You jacked off to a dude."

"Bro... that's wicked." He says as he erupts in laughter. "Oh my god, I beat my meat to a tranny. Hilarious bro."

"That's actually why I invited you here today."

"What? To send me tranny porn?"

"No, asshole. A business opportunity." I hated that word he used. I may make money off the femboys, but I respect what they do for the world.

"Go on."

"I'm thinking about restarting my tutoring service I had in college. But this time, bigger much bigger."

"Wait let me get this straight," I watch him pace the deck as if he was analyzing his next chess move, "you're the one who owns FemboyWorld aren't you?" This motherfucker.

"That's what you got from what I just said?"

"You are, aren't you! God I heard so much about that place. Money that is. You almost had me beat last year. But my Titillating Trips cruise line had you beat. I could not believe a - what do you call it -, 'femboy' almost had my big titty woman beat. You know I was this close to playing dirty with y'all. Shit I almost had you assassinated haha, business-wise I mean."

Knowing Dirk he was actually that close to assassinating me. "Yes I own FemboyWorld. It's not really a secret. You weren't the best at research anyways. And, by the way, I was only 40 million off."

"Haa, you have a nice little business there. So, what do you need me for then?"

"I have an agreement with Easton to build a pipeline of talent at Big U. I need your help with the trustees."

"Big U?" Dirk winces at the words. "After what went down, I don't see you earning their confidence."

"How the hell was I supposed to know that freshman I had working was one of the trustee's grandsons?"

"Just unlucky dude. You would've gotten away with it if he did not get caught stealing test answers in the Dean's office."

"Yeah, that kid was an idiot. Easton was right when he said I should have stuck to the science nerds."

"Every business man has his failures. Except for me, of course!" Dirk laughs in my face, then settles down, "But you were unlucky though. Sorry about that."

"I guess that's why I need you."

"And pray tell what is in it for me if I entertain whatever idea you have."

"I know you invested 400 million in a little science laboratory."

I see Dirk's eyes become sharp and his tone changes to a serious one, "No one was supposed to know about that until Q3 of 2025," No one was supposed to know because he did everything in his power to keep it a secret. If others were to invest, he would lose his large investment share. Luckily for me, one of his head scientists loves to reimagine his high school days at my park. And with that, he loves to spill all the tea about his little laboratory.

"I also know you send up-and-coming actresses there to get work done. One of them has been talked about having the most perfect tits in Hollywood."

"Haha, Tommy you are so funny. You can't blackmail me."

"I'm not here to blackmail you. I'm here to give your laboratory a little test. Can those experimental procedures work on college boys? Imagine that sort of treatment done on Daniel Myers, or should I say, Daphne Myers."

"Wait..." I watch Dirk look up contemplating what's happening. Then his head falls forward with the biggest shit-eating grin on his face. "If my assumption of what you are proposing is true... this could be incredible."

"Just think, Dirk. An army of them. Boys turned into sissies. All from Big U. And with my park turning the nation around about how they feel about femboys, just think if those boys had certain modifications done on them."

"The rich fucks would pay billions for a femboy, or 'sissy' like that."

"And all I need is your help with the trustees. I need you as the point man in the meeting. Use that 'Van Wilder' charm you have to convince them."

"This could be big, dude."

"We have come a long way from your Wings & Breast events."

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A Prime Delivery (POV: Ash)

"This is a big freakin' deal, do you understand that? I need you to understand that."

I looked up and saw Kenzie looking down at me, her tone was so strict.

"Yes, I do. I promise I do."

"Ash, Look me in the eyes and tell me you understand. I don't want you chickening out, I've put too much work into this. You've put too much work into this. Don't let it go to waste."

I nodded, the seriousness of this all coming into focus. "I understand, 100%."

"Good, because my father is a very important man and he said this is extremely important for his reputation and for Big U. If this goes as planned, I'm gonna be set up for life. And I promise we won't forget about all your hard work."

Kenzie Hammerwood was always so...determined. I think that's what drew me to her in the first place. She had lured me in, inviting me to parties, having me sit with her at sports games, even taking me out drinking. I had let her convince me to try on some of her clothes. Then that led to some makeup tutorials. She said that she was into more 'ambiguous' men and said wearing makeup proved that a man was comfortable in his own skin. I let her do it, even though I only saw her date big masculine men who would never put makeup on.

Before I knew it she had me wearing her clothes, her makeup, and even grew my hair out into a feminine style. It wasn't even a man-bun, but a real feminine bob style. When she jerked me off, I was completely taken. It didn't phase me that she kept name-calling me, telling me how small my dick was. I was just so excited that I was having some form of sex with a girl.

When she had me play with the dildos, then when she played with my ass...

I ran through the events quickly in my mind, from the assplay to the practice dildo blowjobs, to the intense and immense amount of porno she made me watch. Some 'hypnos' she called them. She knew my porno tastes and fed them, morphed them. Before I knew it I was dressed up in lingerie, wearing full makeup, sucking one dildo while riding another, and watching a scene of Riley Reid and Mandingo where Riley's tits and pussy had been pixelated out by some hypno editors.

What happened to me? What was wrong with me? What couldn't I stop.

"Ash, focus!" Kenzie said. I snapped out of my daydream. She stroked my hair as she took a seat next to me.

"It's gonna go great, I just know it. You've been just so strong and brave the past couple months. I'm like, already proud of you."

She could go from stern to tender so quickly. I felt those warm feelings, that kinship with her. I was still attracted to her, but now I had a different sort of relationship. I didn't, like, want to have sex with her. But I, like, wanted her.

"You've taken to the hormones so well! Your body is, like, really coming along!"

"Thank you, Kenzie."

"I mean it, keep going like this and you could get hotter than me!" she laughed. Did she mean that? Wait, is that what I wanted? I was a guy, right? I wasn't gay. I wasn't a trans. I...gosh, this whole sissy thing got my head spinning.

"Okay, so I already told him to expect something special. He's supposed to be resting before the big game, last I checked he had just finished up in the ice baths so he should be back at his dorm room soon."

She started fussing with my hair, pulling out a couple of elastic bands.

"Let me just make this look better. You'll learn more styles as your hair gets longer, but this is just called Two Half-Up Half-Down Pigtails. It's super easy," she said as she quickly re-did my hair as I watched in the mirror in front of me. "All you need are two elastics. You just do mini ponytails on both sides of your head and leave out a few front strands of your hair for that cute, messy look. See? Super cute!" she said.

She was right, it was really cute. I liked the strands of hair framing my face, it made me look angelic. Angelic? Is that what I wanted now?

"Anyways, what was I saying? Oh yeah, Jax should be back at his dorm room now. You're actually in luck with him too, I'm so glad my dad decided he'd be the right one to start with. He's very...open, free, liberated. He transferred from Florida and is, like, super open-minded. I think he's really helped the other guys on the football team widen their views on things. I just know he'll love you."

I had heard about Jax. Big U. had suddenly gotten this big donation to the football team from Kenzie's dad Easton Hammerwood. They then out-of-nowhere got the star wide receiver from Florida State to transfer to Big U. It was kind of unspoken, but they had clearly given him some sort of payout, but the NCAA had no idea how to find any papertrail. People were talking about how this could totally change things for Big U, and make our team something to be proud of again.

And now I was going to meet him. Me. Average me, this kid from a rural town with big dreams of going to Big U and who actually got to go here. I hadn't dreamed of ever spending time with the football players, they were like celebrities here. But now here I was about to meet one.

Did I expect to meet one looking like this and under these circumstances? Definitely not. But still, wasn't it cool that I was getting to hang out with the star player? The guys back home would be so jealous. Though I definitely wouldn't tell them how it all happened.

"Ok, so remember what I said. How are you to behave?"

"Simple, Sassy, Sexy." I stated, as if this was natural for me. It still felt a little weird. Well, really weird.

"Good! And tell me, what's the most important thing today?"

I knew what she had instructed me. But this one took me a second, not to remember but just to come to terms with. But I did come to terms with it, and I did say it.

"His pleasure."

"That's right. Don't look so nervous, Ash. You're gonna do great." She took my hands in hers. "I wouldn't have trusted you with this if I didn't think you were the perfect person. This is a big deal, you are doing something important. Not just for me, not just for my father, but for Big U. And for yourself! You're finally going to be someone of importance. Not just some average boy passing through an unimpressive life. You're going to be a SOMEONE!"

It all sounded so promising. She was right too, so far I'd spent so much time at parties, with hot girls, doing drugs and drinking. The crazy shit that I only could have imagined. Somehow my grades didn't suffer. Kenzie had told me she worked something out with my professors so my grades were impeccable and my parents assumed I was hitting the books 24/7. They were so far from the truth.

"Ready?" she asked.

I took a deep breath. There was no going back. I mean, I guess I could have. But then I would have lost all of this. No more parties, no more hot girls, no more being around the action. Back to normalcy, back to boredom, back to anonymity. I didn't want that. I couldn't go back to that.

And who knows, maybe this would...be fun?

I nodded my head. "Ready." I said, sounding confident.

Kenzie helped me up to my feet and wrapped a trench coat around me to cover me up. I looked at the mirror, seeing the feminine face looking back at me. You would have thought I was some pixie girl from a movie, someone who straddled that boy-girl divide in an enticing way. I could barely recognize myself, my delicate features had been highlighted by the makeup and softened by the hormones Kenzie had made me take.

I didn't remember the next half hour. Kenzie had driven me across campus to the dorm nearest the gym. It was the athlete's dorm. We walked through the halls together, with Kenzie waving to all the guys she knew there. Eventually, we made it to the penthouse. There was just a single door there, clearly all this space had been reserved for the new star player.

"Ok, you're on your own from here. Remember everything I taught you. Jax knows he has a surprise from me but doesn't know what it is. Don't be afraid, just do what comes naturally." she instructed.

What comes naturally? Like, run away? I resisted that urge. Do what comes naturally, ok, ok. I nodded, gulping. She walked away, leaving me alone in this hallway. My thoughts ran wild, could I do this? What was going to happen? Do what came naturally? Ok, do what comes naturally.

I knocked on the door.

Fuck no, I have to leave. I can't do this. Dressing up? Sure, that's fine. Makeup? Actors do it, nothing weird about that. All the toys that Kenzie had me play with? It's in the past, it's just kink. But this. This could be a step too far.

But before I could back away, the door opened. In front of me stood Jax himself. This ebony statue of a man. His torso was exposed, he had clearly just come out of the shower and was still shining wet. A towel was wrapped around his waist, which was shaped in that perfect V. His abs glistened. I felt so small and weak in front of him.

It didn't help that I had to look up, his face a good head above mine. I wasn't blessed with height, only 5 feet 6 inches. Even with these heels I was still having to bend my neck back to look him in the eyes. They weren't kidding, athletes are so much bigger in person than on TV.

I was speechless. Luckily he wasn't. I crossed my legs slightly, my right foot over the left, feeling embarrassed.

"Hah, Kenzie said she was sending me a surprise. I thought it was going to be in a box. But you, you sure aren't in a box are you?"

I couldn't get words out, I was blushing. I just wagged my head side to side.

"No, of course not. So, tell me. What's the surprise then?" He said, his eyebrow cocked.

I still couldn't speak. My voice was caught. I was mute. Shit, this was embarrassing. So I just, well, I just acted.

I grabbed my trench coat and pulled it off so that it fell to the floor at my feet. I stood in front of Jax in all my glory.

I didn't see his eyes bug out. He kept his cool, not flinching. His eyebrow was still cocked, but now a small smile started at the corner of his mouth.

I don't know how any man could react so calmly to this. Here he was, just having opened to door to see a stranger who instead of saying anything just drops their trenchcoat to reveal they're wearing a nearly-sheer baby blue croptop, revealing their tummy, with a sheer white-polka-dotted micro-mini frilly skirt that only went down just below the curve of their white thong covered ass, along with thigh-high striped stockings. All that on top of white stripper heels. And if that wasn't enough, a collar around their neck that read, "YOURS"

And he just barely smiled, barely reacted.

"Why don't we get you inside before you catch a cold, sweetheart." he said, gesturing me in. I teetered on my high heels into his dorm room, which was bigger than any I've ever seen. Truly a penthouse suite.

But I was still incredulous. How was he reacting this way? I had made a fool of myself! I'm just glad he didn't notice my tucked-away penis. It was so small now that it easily was hidden even in this tiny thong.