Cheerboi Origins Pt. 01: Femboy World

He brought me over to his couch and had me sit down, then he sat down opposite me in his Laz-Boy. He looked like some Roman emperor, sitting so casually yet so imperiously. Instead of a toga he just had on that towel wrapped around his waist.

"So you're the surprise from Kenzie, huh? Not bad, not bad. You're cute as hell, that's for sure."

I blushed. Wow, was this the first time someone had complimented me on my attractiveness? No girl had ever done that for me, except for the occasional but condescending 'oh you're adorable Ash'. Now Jax, the star player, was saying I was attractive.

"Th-Thanks" I finally got it, the first word I had said to him.

"Found your voice again? Good. Cute and quiet is fine, but I like to talk to my girls. So tell me, what's your name, pretty?"

I hesitated. "Ash-" I started, then paused before finishing abruptly, "-ley. Ashley, Sir."

Wait? Not only had I just introduced myself with the girl name that Kenzie would sometimes call me, but I had called him Sir. It's like Kenzie's instruction was second-nature to me now. 'Just do what comes naturally' is what she had said, after all.

"Ashley, nice. I like that. Now, tell me Ashley, what did Kenzie send you over here for?"

"To, um...to make sure you were fully relaxed before the big game tomorrow."

"Oh is that so? Well that's mighty nice of her. I have been in need of some relaxation. Big U. has put a lot of pressure on me to perform, you know that? Star player and everything. Doesn't help that I'm pretty much here to save this team. It's on me to get the team to playoffs. Can't say I ain't stressed."

"You must be." I said. "Everyone's counting on you."

"Yes, yes they are." he said, looking away in the distance. "Florida State was different. Stronger team, all of us all-stars. But here, I have my work cut out for me."

He focused back up and looked at me.

"But you know what's interesting about our situation here, Ashley? Kenzie and I, well we've messed around a bit, that's for sure. I've messed around with some of her friends too, those Kappa sorority girls do know how to party. They're as hot as the girls at Florida - just as hot, but definitely wilder. I like that."

I knew that was true. She brought me to the Kappa parties and I couldn't believe the bacchanalian scenes that had transpired in front of my eyes.

"But what's interesting, Ashley, is that she could have sent anyone to me. I could have anyone I wanted on this campus. I do usually like a pre-game messaround to relieve stress. But she sent me you of all people. She could have been here herself. But no, instead it's you Ashley. I wonder why that is."

"I uh...I'm not sure either." this guy had such a strange confidence. He just knew that he was important and strong and authoritative. He didn't seem to need to prove anything.

"Stand up." he said. I did as he said, standing up in front of him in this ridiculous outfit. I steadied myself on these absurd heels.

"Give me a twirl." and I did, spinning around for him.

"Show me your pussy, Ashley." he said, calmly and confidently.

So vulgar, so direct. Did guys like him really talk like this?

"I-I..." I mumbled. Was this moment he realized my secret? Fuck, what had Kenzie gotten me into? Back home, fairies got their asses beat.

"I said show me your pussy, Ashley." he said affirmatively, no doubt or hesitation in his voice. Not menacing, just firm. He wanted something, he got it, That was his reality.

I was frozen. What was I supposed to do? I stared down at the ground in front of him.

Then I remembered Kenzie's words again, 'Do what comes naturally'. And it was clear, I knew how Kenzie talked about my body and what she called everything. The new terminology.

I turned around, my heels clanking on his hardwood floors. I then bent over slightly and flipped up my skirt over my ass. I then pulled aside my thong with my fingers, exposing to this man I just met my bejeweled buttplug-filled asshole and...my boiclitty and jewels.

There it was, my secret was out. Nothing to do now but get my ass beat by this muscleman.

"Yes, interesting indeed. You can sit back down, Ash." he said, reverting to my boi name.

I tidied myself back up and sat back down, my face the color of a ripe strawberry.

"You know, back down in Florida there's this place that me and my friends would visit a lot. An amusement park of sorts. Except there weren't big rides or anything. Well, some 'rides' were had." he joked to himself, chuckling. I didn't understand.

"The park was phenomenal, never left a customer anything but completely satisfied. The first time I went there I was so surprised. Instead of pockmarked acne-faced loser guys working at the park, I only saw hot girls. Young, hot, smiling and inviting girls. It was like I was in heaven. But you know what, Ash? They were special. Can you guess why?"

"...No, Sir." I said.

"Because they were 'interesting' just like you. The park was called FemboyWorld. Does that word sound familiar to you?"

I nodded, sometimes Kenzie would call me that.

"A whole park staffed by gorgeous, young, lithe, and welcoming femboys. Some of the guys back home weren't into that. Closed-minded. I've luckily had my eyes opened. When I was recruited here, Kenzie's dad Easton said that I would be able to get similar treatment here. And yet I got nothing these past few months. To be fair, Hammerwood said that Big U. didn't have that kind of talent yet around here. But he said they were working on something. In fact, his eyes lit up when he said the name of the new program. It wasn't femboys, it was something else. Shall I tell you the word he said?"

"Yes, please Sir." I said, my heart was in my throat and I was lightheaded from the tension.

"Sissies." Jax stated. For some reason, I tingled when I heard the word. My whole body got hot.

"And Ash, my dear. It looks like you're the inaugural Big U sissy."

So this was what it was all about? I was part of some financial plan, some recruiting project cooked up by wealthy perverts. Was this what I was prepared for?

"But enough with this chit-chat, Ash. Or should I call you Ashley? I'll think about it, depending on whether you can act like Sissy Ashley or just boring 'Ash'."

He undid the knot on his towel.

"Only one way to find out." He lifted his hips up and whipped the towel off and threw it in the corner of the room.

He sat back down, but now my eyes were filled up not just with his chiseled body but now with his massive dark...cock. The force of his movements gave it momentum, so it teetered left and right like a metronome, the weight of the thing fighting gravity. It was...huge. But it was almost as sculpted as the rest of his body. The dark veins curled around the thing like it was made out of stone. The pink head flared and bulged. His balls were seated in this velvety swollen sac.

My mind couldn't help but look at the thing and think it was beautiful. It was weird, I had seen plenty of cocks in all the porno and hypnos Kenzie had shown me. BBC porn was her favorite so it became my favorite too. The guys all looked ridiculously well-endowed. I thought they were using prosthetics. Not unlike the dildos Kenzie had me play with. But Jax...he was all real. His cock was so fucking real. It had a presence in the room. It had a gravitational pull of its own. A pull that had made my own penis...my sissyclit, come to life and swell, but without making any tent in my thong.

But then I realized my predicament. This wasn't show-and-tell. Jax pulled out his cock for a reason. He wanted something from me.

I had promised Kenzie that the most important thing today was Jax's pleasure. She would be ashamed of me, embarrassed for herself if I came back to her a failure.

She had also told me, 'Do what comes naturally'.

I brushed aside any thought, any opportunity for my brain to say 'Naturally, Ash? Do you really want to admit to yourself that what's coming next is now NATURAL for you?' I had to ignore those thoughts. Kenzie trusted me to act. I wasn't Ash right now, I was Ashley, wasn't I? In fact, I was now Sissy Ashley? Those words made my clit stir.

And more importantly, my body wanted something now.

I slid off the couch and onto my knees, then began crawling towards Jax. He spread his legs apart to give me access, as I crawled slowly into that space he made. My butt wagged seductively behind me. It wasn't a conscious thing, it's just how my body moved now. Or did my mind make me do that subconsciously?

He reached down and fingered my collar, reading it out loud. "Yours." he said. He said it as if it was a natural truth. Like it was the natural and obvious order of things in this world. I was his. He possessed me in this moment. In this position, on my hands and knees before his naked glorious form...it felt undeniable.

But then he did something unexpected. He reached behind my neck and unclasped the collar. Toying with it in his hand he then wrapped it around the base of his cock and snapped it in place. I looked down to see this. His cock which jutted out, measuring maybe 8, 9, 10 inches - I didn't have the experience to eyeball this yet, but it was certainly gargantuan compared to my own - and at the base was the collar dangling there with the word 'YOURS'.

What did he mean by this? Jax leaned back and took his hands off his cock, letting it dangle there again, up at an angle but weighted down. He put his hands behind his head and reclined back and looked down at me, directly in my eyes.

"It's 'yours' now Ash. Yours to do what comes naturally."

There were those words again. Then silence. Nothing but me, this man, and his cock.

I sat up and brought my hand up and wrapped my hand around the base of his cock. My first cock. The first time I touched another guy's cock. I thought it would feel like when I masturbated myself, but it didn't feel like my own. For one, it felt out-of-body to touch a cock and not feel that hand on my cock, like when I masturbate. I touched a cock and only felt cock in my hands. And more importantly, this thing was huge. Kenzie would sometimes playfully mock me, telling me that a real man's cock was so different than mine, especially as she made me play with dildos.

I understood that now. This thing had a life of its own, an architectural beauty of dick. It was both soft and hard at the same time, but I struggled to grip the whole thing. Unconsciously I started stroking it. Not firmly, just loosely, as if my fingers were little cartographers mapping out every topographic feature of his cock. When I felt him harden more, I gripped it tighter and stroked it firmer. It wasn't complicated. I imagined what I would want done to me and I just...well I did it to him.

My subconscious was screaming 'This is gay!' but my conscious body was just going with the flow. Here I was dressed like a slut and here was this stacked football player with a huge cock that he was letting me play with. 'Letting'? I guess he was giving me permission of a sort. This wasn't even coerced. Kenzie convinced me to do this, but I could have left at any point. Jax had been nothing but a gentleman.

"You know, I was serious with that. It is 'Yours' to play with. Don't hold back." Jax said, looking down at me confidently.

I looked up at him, then back down at his cock and my old choker wrapped around its base. I guess...I guess this was like, my time to explore?

I don't know what got into me. I looked up at Jax and asked, all innocent. "All mine?"

"All yours" he confirmed.

I then stared at his cock in my hands and said to it, "All...mine."

So I explored Tentatively at first, leaning forward to do something I hadn't considered ever doing in my entire life.

I licked his cock. It tasted...actually not bad. Kinda, salty but nothing bad at all. The warmth was actually kinda nice. I licked it again, and again, and again. Like an ice cream cone. I didn't know what I was doing but this felt right. It felt like something he would want.

It's what I remembered pornstars doing. So I did it for him.

It was...wow, it was all sorts of things. Challenging, exciting, calming...it was kind of fun. I could feel all his firmness and ridges and veins on my tongue.

I started jerking his cock with my hands while licking him all over. I stroked faster and faster

"Good girl, oh fuck, good girl." I overheard Jax moan.

That just spurred me to go faster, to lick more. I don't know why but those were like magical words.

I started to taste some salty sweet emissions from his cock, I guess that was the precum. It was kinda nice, like honey, fresh from the source.

"Ash...Oh fuck Ashley keep going like that and I'll - " Jax moaned loudly. My eyes fluttered up and I saw his hand on his forehead, his eyes closed intently. He was almost speechless from this!

I felt...wow I felt POWERFUL. Little Ash making the star wide receiver weak in his knees!

I barely had time to soak in that feeling since Jax grabbed my head with his hands and held it there while he pumped up with this cock.

I was powerless, my hands on his thighs as he pumped his cock over me. It looked so powerful, the veins engorged, the head swollen, his hand pumping faster and faster. Then I saw it kind of spasm...then...

Let me say that Kenzie had made me explore a lot. She even made me try my own cum. I didn't necessarily like it, it was just not my cup of team, per say. It had this sort of slightly salty but kind of nothing taste, not my favorite. Kenzie had fed it to me after she gave me a reward handjob, making me lick it off her fingers.

This...This was different. I hadn't realized that my mouth had been parted involuntarily. But Jax's cock literally FIRED ribbons of cum into my mouth. The first one went straight into my open mouth and down my gullet and I swallowed while trying not to choke. He had let go of his cock in his orgasmic fury and my hand had re-grasped it and automatically started pumping it again. Did I do that on my own? Why?

Shot after shot after shot, the creamy stuff coated the inside of my cheeks. Wait, why was I aiming it intentionally into my mouth?

It was like someone sprayed a can of whipped cream into my mouth until it spilled out. I couldn't keep it all in my mouth. Some of it just started dripping from my lips and dribbling down my chin.

Meanwhile, Jax was groaning and then breathing heavily. He leaned back, his cock popping from my lips.

"That was...Ashley you're a natural." he said, looking down at me as I was busy figuring out what to do with all of his cum in my mouth.

"Go ahead, Ash. Swallowing now won't change what just happened. You just gave me a stellar blowjob. Time to finish the act."

I nodded dumbfounded. He was right, I had done it. My hesitation slipped away. I let the flavor sap into my tastebuds then swallowed it all. It wasn't bad. In fact, it was definitely much better than mine. It had a richer quality to it, thicker and more...flavorful. But not the rancid taste that I was expecting. It was like a protein smoothie or something. Salty, actually a little sweet. I didn't mind it at all. In fact, it was kind of...rewarding?

Fuck that sounded weird even just to think. But I couldn't ignore that I had just worked my butt off to suck this guy off and now I had something to show for it, his cum.

It made me realize something that Kenzie had told me once. About how girls famously fake orgasms with guys, and the guys have no idea. But guys could never fake an orgasm with a girl, because there was always evidence. The cumshot was the ultimate evidence, like, no denying the orgasm.

"Good girl." he said, watching me swallow.

There it was again, that phrase. I instinctively smiled at him, my pearly white glowing, probably looking silly with rivulets of his cum still drying on my chin.

"I really needed that, I did." Jax said. He didn't offer to help me to my feet, he just left me on my knees in front of him. My choker was still wrapped around his cock too. He unhooked the chain around it and dangled it in front of me.

"Cool if I keep this for myself?"

I nodded, not knowing why he wanted it.

"Sweet. This thing is like a trophy, I'll put it next to my championship ring." he laughed. "Just so you know, you can come back anytime if you want to wear it for me again."

I giggled at that. A trophy, huh? I guess his cum was my trophy. I couldn't show it off like his though. Well, maybe what was left drying on my face?

Fuck what was wrong with my mind.

"Seriously, that was just awesome. Literally, like FBW level good."

FBW? Like that park?

"Always makes me feel like a fuckin king! Ima dominate tomorrow on the field."

He grabbed his phone and started texting. I heard the 'send' sound and then a quick reply sound.

"Kenzie says she's proud of you." He said. "I told her how much I enjoyed her surprise."

I smiled, "Thanks."

He then stood up and helped me up to my feet. His big cock was flaccid but still huge and flapped around. Damn, that's what real men feel, huh?

I was a little lightheaded when I stood up but he caught me. He even put my trenchcoat back on, but not before sneaking a firm grip of my ass.

"Mmmmm" I unconsciously moaned.

"Next time I'll show you what you've been missing out on. But Kenzie probably has some more training to do before you're ready for that."

Hmmm, I guessed at this meaning. Did...did he just offer to fuck me?

"Tomorrow at the game Ima dedicate my first touchdown to you, girlie. I already know I'll be lighter on my feet with that load you took off me." he joked.

I left Jax's place with so many questions in my head. Why did I just enjoy that so much? Was I gay now? Would Jax tell other people about me? Was he planning on...fucking me? What was FBW?

Then I got a text on my phone from Kenzie that I read as I headed out of the building.

"Jax gave you a stellar review! SO proud of you! I think you're ready for the next step. And it just so happens that my dad just texted me...we have a BIG assignment for you. ONCE IN A LIFETIME OPPORTUNITY. Seriously. Check your email."

I opened my email and saw two things.

First was a calendar invite to something called "Trustee meeting with Mr. Knudsen and New Kappa Sorority Mom Ms. Riggs."

Second was an email from American Airlines.

A first-class ticket to Florida.

What was this for?

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The Trustee Meeting and a Debut (POV: Mr. Knudsen)

*Deep breath* So you may be wondering - yes you, you right there! - you may be wondering, "Why? Why does Mr. Knudsen need BigU's help?" Well, I don't. Hammerwood was actually right when he said that my park makes a lot of money. We are on track to make 800 million in profit for this fiscal year and on track to make a billion in the next. I don't need this.

But the one motivator greater than profit is revenge. An old fuck once said, "To exact revenge for yourself is not only a right, it is an absolute duty."

These men, fifteen years ago, kicked me out of this school for basically being an entrepreneur. I had an idea to pick up my poor-ass bootstraps and help myself through college. But, what do these old men do? They kicked me out. All I was doing was providing a service for the other college boys. A tutoring service that is. Sure there were other benefits. But, what was the difference between what I was doing and any of the frats?

So they kick me out. And after they did, I sat back, built my business, and watched Big U deteriorate into what is today. The alumni became weaker with every graduating class, the donations dried up, athletics deteriorated to mediocrity, and academics floundered. And what do they do after all that? They crawl, begging, back to me.