Cheerboi Origins Pt. 01: Femboy World

Kenzie eased her finger in and out of Ash's boipussy as she grabbed Ash with her other hand wrapping around her waist and pulling her in. Ash was trapped between Ash's lips in front and her exploring finger in back, but all she could do was moan slowly at this remarkably public show of intimacy.

Ash could barely think, barely understand what was going on, barely control her situation as she just surrendered to the feelings.

Then Ash felt something else. She couldn't see but Victoria had surreptitiously handed Kenzie a small item and Kenzie grasped it in her hand as she removed her finger from Ash's hole. Ash's mind slowly cleared at the absence of the invading digit, but her mind was re-focused once again as something else was slipped into her.

Something small but obviously new.

She couldn't have known by the shape nor the size. She hadn't ever known something like this. For Ash has never experienced an anal vibrator before. The perfectly sized 'Vibe' slipped right into his primed hole.

"Oh!" Ash let out. But it was too late to investigate the new intruder.

Ash wasn't sure if he heard it first or felt it first. A gentle humming noise came first perhaps. Or the tingling sensations that filled his rear. Hard to know which came first, but Ash was in new territory. Unexplored territory.

All of a sudden things got slower for Ash. He stopped seeing or thinking or hearing as the vibrations picked up thanks to Victoria's remote control. Ash didn't realize that Kenzie was leading Ash forward, walking this lingerie princess towards the center of the room where a large conference table stood. Someone had placed a step that Kenzie used to lead Ash up it, his heels clicking up the steps.

Ash opened his eyes and realized he was standing on the table. These older men surrounded Ash at their plush seats, their eyes bearing up at this slutty sissified creature above them.

Ash blushed and almost recoiled when Victoria turned up the Vibe settings. The strong vibrations emanated from inside Ash's hole through his inner being. Ash's eyes closed again and a groan came from his lipstick-painted mouth.

The men were beyond themselves with lust. Some of the conservative members of the board forgot that the sensual creature before them was once considered a man. The more open-minded ones didn't care one way or another, they just saw a horny prey, a creature for their pleasure. They took in the sight and marveled in their power...because the weakness in front of them reminded them of their natural position of power of that...sissy.

But Ash was too lost in the sheer euphoria that the Vibe was giving her. The table shook as Ash fell to her knees. She didn't realize it but her hands went to her nipples, tweaking them through her bra. Pleasure...such delightful, sinful, raw pleasure.

Victoria slowed the Vibe down and that pause allowed Ash to catch her breath and open her eyes...to see the men that witnessed her public display of erotica. Embarrassment...that's what Ash thought she would feel. Shame...

But instead shame was replaced with something else...perhaps curiosity at first. These men weren't laughing at her, they did not mock or tease or belittle. No...they were transfixed. All eyes were on Ash because they couldn't keep their eyes off of her. She had their unadulterated attention. Her body did. Ash did. They were lining up for her.

And she was the center of attention. She was their performer. The sheer absurdity of her situation was overwhelming but somehow, just somehow, in this moment it was not debilitating. She should have been paralyzed. Ash, who once dreamed of being the coolest guy at college, who wanted to be 'one of the guys'...was now Ashley, the sexual sissy dynamo being leered at by horny suited powerful men. He was reduced to this new thing. A femboi? A sissy? Something greater?

But Ash didn't have any more time to think. Victoria turned up the Vibe setting again and Ash's insides were turned upside down with radiating bolts of tingling erotic energy.

"Oooooooh!" she moaned. It wasn't just the involuntary moan this time though, it was almost purposeful. It was as though Ash was playing it up, showing these men the erotic situation that she was trapped in. She was performing!

"Yessss." she said. This wasn't forced, this was voluntary. This was Ash communicating to these men that she was in ecstasy and she wanted them to see.

But when Victoria adjusted a setting on the Vibe, it distracted Ash, as new pulses filled her up. She keeled over.

She was lost in these new sensations, she didn't hear Kenzie speak out loud to the men.

"Gentlemen, don't feel so inhibited by the confines of this place of business. We all know how to keep a secret here. Please, feel free to UNLEASH yourselves."

Ash was grinding on the table, her eyes closed, her lithe femboi body making snake-like movements as she enjoyed this feeling of being filled and pleased.

She was in prostatic orgasmic agony. She was about to feel something she had never experienced before in her entire life. And she was about to feel it all publicly, surrounded by men who were ogling her. She had gone from shy guy to femboi sex performer, straight out of an Amsterdam window. But her performance was real, her moans were organic, her movements were natural.

The pulsations built up, stronger and stronger, the vibrations taking over her mind, body and spirit. Ash was getting closer, closer to something. This was better than jerking off, so much better. How had she gone all her life without feeling this wonderful thing? How would she ever go on without feeling it again?

She felt the early signs of an orgasm, but this one was so different than all the ones she had had in her previous life. This one didn't start at her little dicklet, no no. This was deeper inside her. Prostatic, prophetic, primordial. It wasn't like impending release, no it was like an impending explosion. She got closer, and closer, the fireworks in her mind getting bigger and bigger.

Then Ash opened her eyes. That's when, in her inferno of orgasmic buildup, she saw. For while she was writhing in pleasure, these men, these esteemed men, all couldn't help themselves and had whipped out their cocks. Cocks of different sizes, colors, shapes, textures. But all hard, and all for her.

She commanded the room. She was the center of attention. She made men go wild for her.

Ash and Ashley merged.

And it was all too much. The first sissygasm of Ash's life rocked her to the core. She screamed a primal scream. Her body shook uncontrollably, so much that some of the men thought she was having a seizure. It was like watching an exorcism. Perhaps the demons of fake manhood were escaping her.

Her little dicklet leaked and leaked and leaked all over the table.

And Ash collapsed, unconscious.

The door opened and in a sudden outburst, Dirk Diamond stormed into the room wearing a ragged suit and some stylish hangover sunglasses.

"What is up Cocksuck... hey is that girl okay?" Dirk's words of concern pointed toward Ash.

"This girl is the 'girl' I was talking about on your boat, Dirk," I say as I approach him.

"No shit. You weren't kidding Knud..."

One of the big Trustees, having now recovered from his reverie, cuts Dirk off, "Mr. Diamond...oh...it is a great surprise to see you." He springs up from their seat at the sight of Dirk. He was astounded to see Dirk that he forgot about his cum stained suit pants and softening cock jutting out.

"Oh yes, nice to see you old farts. So I'm here because, because..." Dirks wags his hand at me for some help remembering why he is here at the most important meeting of my life while he is hung the hell over.

"The Big U sissy program, Dirk," I whisper to him.

"Yes, of course, the sissies! I am here as a business partner with Mr. Kundsen. Together we are here to establish..." Dirk dares to yawn in the face of these trustees, "The Big U. Sissy Program."

I tap Dirk on the shoulder and whisper, "We already finished the opener an hour ago Dirk."

"No shit, I'm that late?"

"Yes, Dirk. You missed the whole show." I say pointedly.

"Well okay then. I prepared all night while one of your femboys sucked me off. Damn boi had a suction cup for a mouth," Dirk said, adjusting his crotch.

My attention turns back to the trustees, "And you see that men? My femboys could make the best of our alumni like Dirk, late for business meetings and hungover on orgasms. Now imagine what our very own Big U Sissies like Ash could achieve who is way more feminine and much more alluring to powerful men like yourselves. You all did not even touch the girl and I bet your sacks are drained. No boring old wife can make you feel that way. Just imagine how you would feel with an hour with her in all those weird sex rooms you have."

"Yeah, you fucks. I had to kick off all the women on my yacht 'The Cockfighter' for this man's femboys. Now I have a hankering to try one of his 'sissies' if they're anything like his fembois. So you geezers better not disappoint me."

I whisper again to Dirk, "Tell them about your contribution."

"My huh?"

"Contribu... tell them your part, Dirk,"

"The medical assholes?"

"Yes, Dirk."

"As you fucks know, I own a medical establishment that has done work on the most successful actresses in Hollywood. Along with the increased donations to the school, my medical team will be developing pioneering new surgeries and treatments that will allow these former boys to become Sissy goddesses. And all achievements will be contributed to Big U and increasing its reach and status."

"I believe we will have to discuss this amongst ourselves," One of the trustees announced.

"No, No! I am not waking up early again to come back here for you to give a one word answer. Choose now," Dirk says, slamming his hand on the table.

"You see that girl," I point to Ash, "Imagine an entire squad of horny sissies, trained by our hottest sorority, begging to get fucked by the best Big U has to offer. As trustees, you are the biggest of the big. They will be on their knees the moment you call for them.

"We have a deal," The trustee at the head of the table says. He stands up. His cum stains all over his tie and suit jacket and a flopping soft spent dick. But I expect a donation of at least 2 million dollars from each of our biggest alumni. If you keep the money flowing, this 'sex sissy thing' you have going on will be allowed on campus. But, if any harm comes from this, Big U will deny any involvement and all blame will be put on FBW Enterprises. Is that clear?"

"Crystal clear," I reply. I hold out my hand. The man's cum stained hand reaches out to shake mine. I avoid it by giving him a fist bump.

I pick up Ash and we leave the room. A trail of perky femboys I had waiting outside went into the room to, "clean up" the trustees. Nothing sweetens the deal like an unexpected reward.

Ash started to wake up but only saw or heard glimpses of reality, the post-orgasmic haze washing over her.

She felt warmth, not just on the inside but a sticky warmth on her face, lips, and body.

She heard manly gutteral groans and high-pitched squeal.

She heard Victoria say "Good job, girlie."

But it was all too much. She drifted back to sleep. She didn't wake up until well after Victoria and Kenzie had brought her to the showers and cleaned her up, washing all the spent cum from the men off of her. For they had all been too excited, and all anointed their new sissy plaything with their seed, one by one unloading on her as she trembled in the afterglow of her sissygasm.

Ash just slept, and slept long, not waking up until the afternoon of the next day.

That ticket to Florida was waiting for her...

-------------------------------------------------------------------------------------------------------------------------

HOOTERS: NEW AND IMPROVED (POV: Ash)

I breathed deeply, staring at myself in the mirror ahead of me, bright lightbulbs studying it like it was some Hollywood studio green room.

If you had asked me a year ago what I would be doing during my winter break, I may have said going to Florida to soak up the sun. But I definitely wouldn't have been in Florida like this - dressed up in a Hooters outfit, wearing full makeup and with blonde feminine hair.

I touched up my makeup in the mirror, nervously trying not to over-do it while Kenzie's review of my episode with Jax ran through my head. She gave me so much advice and instructions, I was struggling to keep it all straight.

"Remember to maintain eye contact more, men love to see their cocksucker looking submissive but thankful for the opportunity. Oh, and it's fine to kneel or be on all-fours, but try other positions, especially yoga positions that make the man think you're contorting yourself just to get a go at his cock. They love that. And it's ok to gag, most guys like it - shows them how much you're struggling to please them. But we'll have to get rid of that instinct soon enough - don't do it too much or it'll gross the guy out. They like being dominant but they're not sadists. Oh, and don't forget to clean their dicks when they're done. It's just good sissy etiquette."

She had even more to say about how to behave, how to talk to a guy, how to walk better, how to attract the 'right' kind of attention. This was harder than real class.

And now, two weeks later - two weeks of more laser hair removal, tanning salons, beauty salons, manicures, pedicures, spa treatments, and of course the hormone shots - and now I'm here. I barely remembered the flight or the drive through this amusement park. I remember looking up and seeing the sign 'FBW' at the entrance, wondering what that meant. Lucky for me, Kenzie had allowed me to wear boy clothes for my trip. Even with that instruction, I still ended up wearing these short cotton shorts and a tank top, nothing masculine about them. The driver didn't blink an eye, though his eyes were covered with dark sunglasses and he didn't utter a word the whole drive. At least the sign he held at the airport said 'Ash' and not 'Ashley'. That would have been a lot to handle in public.

I looked at the reflection in the mirror. Staring back at me was what appeared a petite blonde girl in a white Hooters tanktop tucked into (very) short orange shorts, perched on a pair of white tennis sneakers in white tube socks. Her chest was kinda flat, but with two small mounds and pert nipples trying to hide behind the cotton. The Hooters logo had a small adjustment though, with the letters 'FBW' in smaller font in the corner of the 'Hooters' logo. I still didn't know what it meant.

The person in the mirror was, without a doubt, cute. Like, the kind of girl I would have had a crush on. She looked like a tomboy a bit, and the small tits didn't help.

I grabbed the pin from the vanity in front of me and put it on my shirt. It read, "Ashley".

I took a deep breath and sighed. This is me now. How did I end up here?

I didn't have too much time to reflect on that question because the door to this back room opened loudly and the chatter of a crowd filled the air as I realized I had company.

And not just company, beautiful company! Six gorgeous girls strode into the room in a cacophony of noise. They were laughing and chatting and hollering a storm.

"No, you did NOT!" said one redhead.

"I totally did!" replied the brunette, who threw her bag up on the vanity next to me. "I texted him that pic and said that if he admits that I do it better than his wife that I'd show up to his work and do it for him during a meeting!"

"You are insatiable, you know that?" the redhead said, as she put her bag on the vanity on the other side of me. I felt awkward being in the middle of these two gorgeous girls.

"Oh, I'm sorry I didn't mean to take anyone's seat." I said, nervously.

"Don't worry, darling! We all do our outfits and makeup at home." said the redhead. "Can't be seen in public looking all plain and ugly!"

"You know it. Though the commute ends up being slower because I have to wave at every guy that catcalls me." said the brunette.

"So what's your name, sweetheart?" asked the redhead.

"Ash." I mumbled, before realizing I had a tag on my shirt that said otherwise. "I mean, Ashley."

"Oh my god, you're the newbie! I heard that we were getting a newbie joining us today!" said the redhead all excited.

The brunette put her hand on my shoulders. "No way! This one's not like us though, is she? They said something about a 'sissy'."

Shit, this could not have gotten more embarrassing. These hot girls were going to mock me, I knew it. I was glad that Kenzie had taught me how to hide my little dick away so they wouldn't see. Kenzie kept calling it a 'sissyclit', and would insist I make it as discrete as possible all the time.

"Umm, yeah..I am..."

"Great! I'm Joey, by the way." the redhead said.

"Paris." said the brunette.

They pointed at the other three girls, "And that's Kris over there," pointing to the blonde. "And Presley and Dakota over there." I admired the gorgeous girls, all of them petite spinners who looking impeccable in their outfits. Like me, they didn't have much tits-wise but it actually just made them look cuter.

"You girls are beautiful!" I exclaimed.

"Aw thanks, honey! You're not so bad yourself!" Paris said.

"That's so nice," I blushed. "I feel kind of silly in this outfit to be honest."

"Are you kidding? You look so freakin' cute." Joey said, rubbing my back.

"The guys are gonna go ga-ga over you," Paris said, rubbing my back from the other side.

"Stand up for us!" Joey said. I got up and they walked a 360 around me.

"Seriously, that ass. I would have killed for that when I started." Joey said. "It's true what they say, some people are just born to be sissies. No doubt with you."

"Thanks, I guess." I replied. It was a compliment but did I want to be so...natural about all this?

My crop-top rode up a bit, showing my thin tummy. These girls had similarly toned fronts, and shapely hips and asses.

"I'm so impressed you're that good at tucking already! I used to struggle with that so much." Paris said.

"Wait, you two are...?" Could that be true? They were like me???

"Femboys, duh! What, did you think we had pussies or something?" the two of them laughed. "Hey Presley, Dakota, Kris! The newbie thought we were real girls!"

They all laughed and the others came to stand around me. I was turning a bright red at the attention.

"Do I look like some boring woman to you?" Paris said. She pulled her shorts down slightly to reveal a tiny little penis hidden in a thong.

The rest did the same. Before I knew it I was surrounded by four gorgeous femboys exposing their little dicks and Joey who had much bigger dick than the rest but somehow still looked girly and irresistible. They wagged them playfully.

"So we've shown you ours, time for you to show us yours," Dakota said. She was so adorable, probably 5 foot 4 with delicate features, like a China doll.

"Ummm...ok, ok." I said, slowly lowering my shorts down. Out flopped my similarly small dicklet, but mine looked different than theirs.

"Oh my god, it's adorable!" exclaimed Kris. She - he? - reached down and twiddled with my member.

"Wow, they weren't kidding about sissies, you are dedicated!" said Paris. "I don't think I could manage being in a little cage like that for long."

My little dicklet was sealed off in a pink plastic cage. Kenzie had put it on me after my episode with Jax. When she told me about this Florida trip she said that I had to behave and she couldn't have me reverting to old ways, and that this cage would help. I was hesitant, obviously. A chastity cage? That was a level of BDSM that was beyond what I wanted to do. But when Kenzie put it on me it wasn't that uncomfortable. And I kinda got used to it. I learned how to tuck it away easily. I learned how to go to the bathroom easily - now that I sat down on the toilet this was actually easier. After a week or so I just forgot all about this new device on me.