Cheerboi Origins Pt. 01: Femboy World

But, I am not that petty. I will help them. I had some good times here. But it comes at a price. Do these trustees who kicked me out think they are righteous, moral, god-fearing men? Alright, let's find out. But I for one know that today, I have come back to fulfill my duty.

And it looks like my special girl has just arrived.

"Long time no see, Tommy. Still making an empire on spent cum?"

I squint my eyes at her, " ha ha Veronica, but yes I am, but on a much grander scale. I hear you got married to some lucky guy - so you must now be called Veronica 'Butler', or maybe Veronica

'Cash', or maybe Veronica 'James'? I can never keep it straight, there's always a new sucker on your arm."

"It's Riggs now, honey. Veronica Riggs." She says proudly

"What, another movie producer?"

"Nope. Just an ordinary man. A good man." She says softly as she caresses her chest.

I fail to hide my surprise at what Veronica is silently conveying, "So you actually settled down, Ms. Riggs. I guess congratulations are in place."

"Thanks, Tommy. I think this is the one. May have to settle down and put another Kappa into this world in a couple of years."

"So someone has finally tamed one of the greatest Kappas, huh? I have heard through the grapevine that the Kappas could never recreate a sorority sister like you were."

"Thanks, Tommy." We share a silent moment of shared comradery. Unknown to those idiots in the other room, Veronica and I ran a slick business operation at Big U. She was president of the Kappas and I had my college fembois. We scouted horny boys and promoted each other. We would share info and communicate on anything new that could make our offers more lucrative. But, when it all fell down, I took the fall and shielded Veronica from any liability. She always told me she owed me one but I never took up her offer. She was one of my few genuine friends. But business always takes precedence. So now I'm calling in that favor. "You're lucky, Tommy. I said once I got knocked up with my husband's kid, I would walk away from my sluttiness. I guess I have one more in me before I stop my birth control." She strips from her coat and reveals a sexy pink bra and sheer pink skirt.

"I always knew you would make a fantastic MILF, Veronica," I say playfully lusting over her.

"I know right," she whips her hair and pushes up her boob. "So am I here to do a little striptease for these old geezers or are we talking 'champagne room' action?"

With perfect timing, Easton's daughter Kenzie Hammerwood walks into the waiting room with our main attraction. I point over to the door, directing her attention there, "you will be showcasing your talents with her."

Kenzie Hammerwood comes walking hand in hand with Ash, they're much-talked about 'sissy'. It is my first time seeing Ash but she is stunning. Definitely similar to my femboys, but with more feminine energy and looks. I've done my fair share of femboy training, but I have to say I'm pretty impressed with what Kenzie has made. At least on the surface. Ash is almost - key word, almost - devoid of clear masculinity. This Ash is on their way to sissy perfection.

"And who may this lovely girl be?" Veronica asks as Kenzie and Ash arrive.

"This is the newest Kappa pledge and first ever Big U. official 'sissy'. May I introduce the lovely Ash." Kenzie says in a cheery Cali girl tone.

"A sissy!" Veronica turns her questioning look towards me, "this has you and Easton written all over it." Veronica has known many of my femboys, but this 'sissy' concept is new to her.

"What can I say? Doesn't Ash here look like what every man craves? That classic femboy appeal but with far more femme. And not just physically, but mentally. A femboy gives lithe sensual beauty with the sex drive of a horny young man. This 'sissy' gives you all that, but with the brain of a verified pornstar. A lot harder to find a true sissy but when you do, there won't be a man in sight who won't pay good money to spend time with her."

There was something I had noticed, my femboys would use 'he' but these sissies seemed to go with 'she' instead. Really said something about how feminine they were and wanted to be.

Veronica examines Ash looking her up and down, "I must admit, you are turning this femboy into a stunner."

"Sissy, not femboy. You'll see the difference, trust me."

"Whatever, Tommy. So what is our task?" Veronica asks getting ready to unleash her last slutty act before motherhood.

"I need the both of you," I look at both Veronica and Ash, "to convince these old men to start an officially sponsored Big U. Sissy program at the Kappa house."

"What, so me and hot little Kenzie here are gonna have ourselves a geriatric orgy with those fuckers in there?." Veronica joked.

I chuckle and open up my briefcase and take out two twelve inch black dildos for the girls, "No, no, hun. You both will be showing your skills with these, and her." I nodded over at Ash, who looked so bashful. "The sexiest Kappa in Big U history, the future of the Kappa legacy, and our new Big U. sissy showing us a sample of what they're capable of. Let them see how the 'sissy' stacks up when next to two bonafide bombshells. Watch their brains explode as they realize what a sissy does to their libido."

"You sure Ash is up to the task?" Veronica asks as she is now in a pink lingerie bra and panties. Her bust and plump ass even stirred something inside of me.

Kenzie walks behind Ash and sheds her clothes revealing the same lingerie set and says, "Of course she is. She already proved that to one of our star football players. Haven't you, Ash?"

We all watch as Ash nods her head timidly. Not that I am a little nervous. It is one thing to please a man in private. But, the true sign of a real cock throbber is being a slut for a group of men. Especially men who will not be able to touch.

"The trustees will see you now." A small, but extremely cute pale girl announces peeking through the door.

"Come on girls, time to make some money." Veronica takes the hand of Ash and they head on in. I look towards Kenzie and say, "Show them a real good time, these old men love to see Kappas in action."

"As long as you will never tell my father, daddy." She says as she strips down in her own pink lingerie and trails her finger across my chest.

"Never will babygirl." As I grab her arm and kiss her. Of course I have been fucking Easton's daughter! How else did I know to propose her as the mentor for Big U sissies? I have been Kenzie's Sugar Daddy since she stepped foot on Big U. Although I love my Femboys, I could not resist her DD tits on her thin frame. Only 1 percent of girls can turn a man's head away from a femboy and Kenzie is one of them.

They all cover up with trench coats, putting away their lingerie-clad bodies for the time being.

We walk into the trustee's boardroom and we are greeted by the stern look of twelve geriatric old conservative men and three "young men" who are only sitting there due to some form of nepotism. But, as any good businessman knows, never walk into a negotiation without an ace up your sleeve.

"Good Afternoon Mr. Knudsen and ladies. My name is Clemet Whitelock CEO of Nile Industries and President of this Board. We have heard from the accomplished and esteemed Mr. Hammerwood that you Mr. Knudsen have a proposal for us to bring in a new revenue stream for Big U. The purpose of this meeting is for everyone here to get a better understanding of how you plan to help this institution."

"Thank you, Mr. Whitelock and the rest of the trustees. As you all know my name is Mr. Knudsen, and to my left is Ms. Veronica Riggs an esteemed alumni of Big U. To my right is current Kappa member and president Kenzie Hammerwood, Daughter of Easton Hammerwood. She is one of Big U's brightest students and earned a prestigious internship in New York City last summer. And last but not least is the subject of today's meeting. This little beautiful minx here is Ash. This beautiful boi..." I stumbled, so used to saying 'femboi'.

"A boy? No, this is a crossdressing abomination. We at Big U do not condone this homosexual nature. This is a respected, moral institution, sir." An old voice interrupted me.

Kenzie, Veronica, and my head turn to the disgusting old man talking. He's a 70 year old former evangelical pastor who made his millions by manipulating his followers and many over the country to send him money to "spread the word of god." Despicable man really, but with all southern preachers, they all have their sins.

"It's funny you are so quick to judge my offer. As if we should see how quick to judge all of you church patrons will be about your little trips to Thailand and all of the... "god fearing" things you did there."

The decrepit old man closed his mouth, sunk his eyes and his frail buns sunk back in his chair. "As I was saying," I say as to make the old man hush, "as you all should be aware of, over the last fifteen years," which just so happens to coincide with my explosion, "Big U has been the laughing stock of the athletic conference, academics, and alumni. And none of you men have been doing anything to solve this problem. You just collected your checks sitting on your ass...."

"Excuse me, sir," another but more respectful old man interrupts me, "I just need to know why we should take the advice of a former student who was expelled at Big U."

"Well this former expelled student just so happens to run a burgeoning entertainment empire in Florida and from what I can remember a couple of you are already frequent customers at my establishment. Hello again Mr. Kramer and Mr. Bagshaw."

They tilt their heads to me. One should always come into a negotiation with votes in your pocket.

"My femboys have been turning some of you... "god-fearing" men for years now. I am certain all of you have had a wank at least one of my femboys. But for my newest endeavor, I am looking to give exclusively to Big U. Ash here is the future of Big U and our official sissy."

"A sissy? So this is a boy?" One of them asks bewildered.

"Exactly, Sir. Ash here is not even complete. There is still tons that needs to be done for her to be what I imagine to be a true Big U Sissy. Whether that be from her acceptance of being a sissy, to pleasing men, and choosing to enhance her own body. Even with all that still left, doesn't she just make your cock flinch. Plus I know you all know the famous Dirk Diamond, right?"

All of their heads nod either remembering the stories they heard of Dirk's infamous parties or eye fucking Ash as she nervously and absent-mindedly slides her hand up and down the black dildo she is holding. "Well Dirk is currently in his own negotiations with elite pharmaceutical companies to come on board and enhance our future Big U. sissies."

"That is all well and good, Sir. But, how do these 'Big U sissies', as you call them, exactly help Big U?" One of the newer trustee members asks near the far end of the table.

"As some of you may or may not know, I am the founder and CEO of FBW Industries and the FemboyWorld park in Florida. My Femboys has grossed over 100 million in profit in the first three years and is about to explode with the expansion of the park. What I am offering this school is a piece of the pie. Allow me and the wonderful Kappa sorority to cultivate and mold these failed males like Ash and turn them into money printing machines."

I can see their faces turning around on the idea and they just need a little bit more of a push. "I and these girls by my side believe that sissies like Ash will bring in the best professors and scientists, the finest students around the world, and world class Olympic level athletes to our sports teams. All of that could be ours if you allow us to start our program."

"The logistics just do not make any sense. Turning boys into sissies like her. Our reputation would be ruined, tarnished. A laughing stock of any academic institution. Even prosecution!"

Valid point. But everything has some give and take, even if it means breaking my philosophy of making every man happy. "And that is why the sissies will be exclusive to... what did you call them Veronica?"

"Alpha males, Mr. Knudsen." Veronica says in her sultry voice looking directly at each one of the trustees.

"Yes, alpha males. The exclusive of the exclusive. Our priority should be focused on recruiting the best professors, bringing in the biggest donations from the sports programs, and graduating the finest students to become rich and powerful alumni. I certainly believe these Alpha men will not only be enticed but lust over these bois during their stay at Big U. And if there is one thing I know, men, especially alpha males, love failed males like Ash here. Dominating a boi who was supposed to be a man is truly a feeling like no other. There is no drug like claiming another boi with your cum. Just sheer power raging through you, the ultimate conquest for an alpha male.

I continued, to assure them, "And if there is one thing I know, rich men will always hold a secret close if it is only exclusive and pleasurable to us."

I smile at the sound of affirmation coughs ring through the room. Each man here is a part of their respective secret society of sorts. I guess that's why FemboyWorld was successful from its inception. It gave the average horny, gay or bi-curious man the feeling that they knew something others did not. As if this was their own club that just stumbled upon.

I looked around the room and saw the unmistakable glint of some secret society rings worn by the wealthy men in the room. Most prominent were the Bull & Horns Society signet rings, that elite group of self-named 'Hornsmen'. I had been recruited by them, but my expulsion cut that journey short. But I was a deserving member of their secret group, certainly living up to their reputation for being particularly well-endowed, and I didn't just mean a trust fund endowment. There was more testosterone in that group than in the UFC.

"And if you men don't believe me now, I have a little show for you to show the full power of a cheersissy. My three beautiful girls here - or should I say two girls and one very special 'girl' - will put on a show for you, a sample if you will. I think you may be surprised who you will be most pleased by at the end. And please don't be shy if you find yourselves needing to 'unleash' yourselves. We won't judge you too hard."

I knew I had them in the palm of my hands, now for the final chess move.

"Girls...begin."

Victoria and Kenzie both encourage Ash forward with a gentle nudge. Ash, her feminized boyish figure teeters forward in her impossibly high heels.

Ash could feel all eyes on her, and the eyes of all these older men made her feel so nervous. Even if she was still in normal boy clothes she'd feel the same way. She'd never been around so many influential and powerful men. It was frightening. Add to that this ridiculous outfit and it was an impossibly intimidating feat to just stand there before them.

Kenzie helped her along. "Gentlemen, Ash here is a little shy. And why wouldn't she be? That's the thing with sissies, they feel so out of place amongst powerful men like yourselves. They were never meant to be amongst you when they were pretending to be boys. But with the femboy treatment, they start to understand what they're meant to do when surrounded by real men."

Kenzie nudged Ash again, "Isn't that right, Ash? There's a natural tendency amongst sissies when they find themselves in rooms of Alpha men. They just need to show their subservient position in life." Kenzie had not-so-subtly emphasized the word 'show' and Ash began to understand.

"Come on, Ash. Don't disappoint us." Kenzie whispered into Ash's ear, to make it plain.

"Yes, Kenzie." Ash whispered back.

That's when she untied the knot on her trench coat. Kenzie and Victoria stood to her side and with their hands glided the coat off Ash's shoulders.

Ash stood before this room of older men wearing just the set of pink frilly lingerie. Fake breastforms made her bra fill out, and her sissyclit was tucked neatly away. To their eyes she was this feminine but-somehow-mysteriously-boyish figure, a sight to behold in the pink lingerie set with garters and high heels. Like a treat being presented just for their enjoyment.

Victoria and Kenzie followed suit and dropped their coats as well, revealing their bodacious bodies in matching lingerie as Ash's. Yet all eyes in the room were fixated on this strange and alluring creature, this version of a femboy, a sissy, something more, something altogether new and tempting.

Three gorgeous figures stood at the head of the table, decked out in fine lingerie, their bodies slowly gyrating. The men in the room could hardly believe their eyes. The younger men were familiar with Femboi World but themselves never went, no thanks to the strict code of conduct that Big U had imposed. The older men were captivated, not used to such displays.

"Like what you see, gentlemen?" Victoria asked rhetorically. It was obvious they did. Zippers were being tested as boners sprung up across the room.

"There's no shame, you ought to be aroused by this...weak, effeminate thing. These delicate features, the flawless smooth young body, those eyes that invite you in."

Victoria and Kenzie rubbed their hands all over Ash's body now, causing Ash to close her eyes and roll her body more.

"Just look at this round and supple ass..." Kenzie said, bringing Ash in profile to the men at the table.

Victoria joined in, kneading a toned buttcheek, "It's as if it was made for you...for you to enjoy." She spanked Ash suddenly, causing Ash to let out a girlish squeal. A man audibly groaned in the back.

"It's not complicated. This body was meant to give pleasure." Victoria said. "Pleasure to powerful men who know how to tame it."

Kenzie then pulled Ash's panties aside, and Ash's shrunken sissyclit was let free. It didn't spring forth or dangle...it was just sort of stuck-on there. Like a decoration, like misletoe above a door. It served no purpose but to signal something to the world.

The older men were so conflicted when they saw it. Their minds told them this was wrong, this was against their core beliefs. But their bodies told them something else. It told them that their primal desires could not be denied. It told them that they should feed those manly instincts that society had suppressed...

To conquer, to dominate, to ravage. The sight of a sissy made them remember their purpose as Alphas.

"Don't look away, take in this embarrassment." Kenzie said.

"It wasn't meant to please women, how could it!?" she laughed maniacally. Ash blushed at her insulting words, but didn't say a thing. Perhaps it was settling in that this was the truth.

"It's meant to confirm her femininity." Victoria said, flicking the tiny thing. Ash winced.

"For this is not what Ash uses anymore, this is not a sexual organ." Victoria continued. And Kenzie picked up where she left off, standing up and tapping a ring-covered finger against Ash's lipstick-coated lips.

"This is her sex organ." Kenzie said, as Ash instinctively opened her mouth and wrapped her tongue around Kenzie's digit.

Victoria then pulled the panties out from between Ash's buttcheeks, pushing it to the side. Kenzie then removed her wet finger from Ash's mouth and dropped it there to tease Ash's asshole.

"And this is her sex organ." Kenzie said, before slowly inserting it into the target.

Ash froze up at the invasion. Kenzie noticed this and knew what she had to do, quickly smashing her own lips against Ash's.

They remained locked in a passionate kiss, causing Ash's body to loosen up, and the men in the room now just had to grab their own cocks through their clothes at the riveting sight of this feminine beauty.